Solubility in Supercritical Carbon Dioxide

CAT4240—PRELIMS —2/11/2006—SRIDHAR—XML MODEL C – pp. 1–48 CAT4240—PRELIMS —2/11/2006—SRIDHAR—XML MODEL C – pp. 1–48 ...

Author: Gupta R.B. | Shim J.-J.

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CAT4240—PRELIMS —2/11/2006—SRIDHAR—XML MODEL C – pp. 1–48

CAT4240—PRELIMS —2/11/2006—SRIDHAR—XML MODEL C – pp. 1–48

CAT4240—PRELIMS —2/11/2006—SRIDHAR—XML MODEL C – pp. 1–48

Preface Since Cagniard de la Tour discovered the special phenomenon of supercritical ﬂuid in 1822 and Hannay and Hogarth observed its solvent power in 1879, various aspects of supercritical ﬂuids have received signiﬁcant attention. Major advancements in the technology aspects of supercritical ﬂuids have occurred, especially over the last 25 years, in the extraction of petrochemicals, foods, pharmaceuticals, fragrances, ﬂavors, nutraceuticals, and pesticides; polymerization and biological reactions, and various organic and inorganic chemical reactions; cleaning of semiconductors and precision machinery; aerogel manufacturing; textile dyeing and dry cleaning; metal de-binding; and manufacturing of micro- and nano-particles. Commercial applications include coffee and tea decaffeination, nicotine removal from tobacco, extraction of fragrances and ﬂavors, plant wastewater treatment, dry cleaning, and residuum oil extraction. The scope of supercritical ﬂuid technology is expanding into a variety of areas including chemistry, biology, food science, environmental science, military, cosmetics, textile engineering, metallurgical engineering, semiconductor industry, and polymer industry. Supercritical ﬂuids exhibit liquid-like solvent properties and gas-like transport properties. The combination of these properties makes supercritical ﬂuids suitable for the various applications mentioned above. Carbon dioxide is the supercritical ﬂuid of choice due to its mild critical temperature, nontoxicity, nonﬂammability, and low cost. Carbon dioxide becomes a supercritical ﬂuid when it is heated above 31.18C and simultaneously compressed above 73.8 bar. The environmentally benign nature of carbon dioxide comes from its very stable molecular bonds, which in turn do not provide high polarity. In fact, a carbon dioxide molecule has only a weak quadrupole moment, due to minor charge separation on oxygen and carbon atoms. Hence, the molecular interaction with most polar and heavy substances of interest is minor, providing only a weak solvent power. If needed, a small amount of cosolvent (also termed as entrainer or modiﬁer) is added to enhance polarity and afﬁnity with solutes. In many applications, however, the design limitation is the solubility of the substance in supercritical carbon dioxide. Therefore, the solubility data are essential both for the initial feasibility study and ﬁnal process design. This book provides a compilation of solubility data in supercritical carbon dioxide for various liquids, solids, polymers, foods, drugs, nutraceuticals, pesticides, dyes, metal complexes, etc. The data were compiled from various research articles, reports, and theses. A reasonable effort was made to ensure that all published data are compiled in this book. However, there may be some research papers that are not tracked in literature searches, especially those written in nonEnglish languages. The solubility data are arranged in alphabetical order of the compound name for easy access, and the data are provided in both tabular and graphical format for better understanding and easier comparison of the solubility behavior of these compounds. At the end of each table, compound synonym(s) and the reference for the original data are provided. Although the source articles provide data in various units, this book uses a uniform unit of mole fraction solubility, or weight fraction solubility if the molecular weight is not known, both in the order of 106 (i.e., parts per million). This book provides only actual experimental solubility data, and does not contain any empirical or theoretical correlations or predictions, except for a brief discussion of modeling in the Introduction. Collecting over 1200 data tables and compiling them accurately into the present format was an intensive effort. The authors appreciate the assistance of several people at Yeungnam University and Auburn University, including Sang Min Paek, Yeong-Ju Kim, Hyo-jung Kim, Mee Hwa Kim, Jong-Won Kim, Da Young Baek, Auburn Hudgins, Suhaila Rowe, Christy Hea, Haley Brooks, Bhaven Sayania, Dmitri Varlamov, Charles Angels, Jerald Dumas, and Katherine Wilbank. We greatly appreciate Dr. Dirk Tuma, University of Kaiserslautern, Germany, for his comprehensive review of tables and graphs and suggestions on synonyms. We are grateful to Peter Livant,

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Department of Chemistry, Auburn University, and Choon Sup Ra, Department of Chemistry, Yeungnam University, for their suggestions in selecting synonyms for chemical complexes. We also appreciate the efforts of researchers who responded to our inquiries to verify their published data. JJS appreciates partial ﬁnancial support by the Yeungnam University research grants in 2004. Finally, support from our families—Deepti, Pranjal, and Rohan Gupta, and Mee-Hee, So-Youn, and Joseph Shim—was key to the completion of this book.

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Authors Ram B. Gupta is professor of chemical engineering at Auburn University, Alabama. He has published numerous research papers, holds several patents on supercritical ﬂuid technology, and is the recipient of the James A. Shannon Director’s Award (1998) from the National Institutes of Health (1998), Young Faculty Career Enhancement Award (1997) from Alabama NSF-EPSCoR, Junior and Senior Research Awards (1998, 2002) from the Auburn Alumni Engineering Council, and Science and Engineering Award (2002–2004) from DuPont. He serves on the editorial/advisory boards of Nanomedicine: Nanotechnology, Biology and Medicine, the Journal of Biomedical Nanotechnology, and Industrial & Engineering Chemistry Research. In addition, he is consultant to various companies on supercritical ﬂuid technology. He received the B.E. degree (1987) from the Indian Institute of Technology, Roorkee, India, the M.S. degree (1989) from the University of Calgary, Canada, and the Ph.D. degree (1993) from the University of Texas at Austin, all in chemical engineering. Jae-Jin Shim is professor of chemical engineering at Yeungnam University, Korea (Republic of). He received his B.S. degree (1980) from Seoul National University, South Korea, M.S. degree (1982) from the Korea Advanced Institute of Science and Technology (KAIST), and Ph.D. degree (1990) from the University of Texas at Austin, all in chemical engineering. He has served as the chairman of the School of Chemical Engineering and Technology and as the associate dean of engineering for academic affairs at Yeungnam University. He also has served on the numerous government committees in Korea for research and education program evaluations. He serves as the editor of Clean Technology published by the Korean Society of Clean Technology and the director of the Institute of Clean Technology at Yeungnam University and is a member of American Institute of Chemical Engineers and the Korean Institute of Chemical Engineers. He has extensively published research papers on the phase equilibria of supercritical ﬂuid-polymer systems, supercritical ﬂuid chromatography, solubility of solid dyes in supercritical carbon dioxide and cosolvent-laden supercritical ﬂuids and their sorption in polymers and textiles, and polymerizations and chemical reactions in supercritical ﬂuids.

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Abbreviations SOLUBILITY M S W w y

Molar solubility (moles solute/liter of CO2) Mass solubility per volume of CO2 (g solute/liter of CO2) Mass solubility per mass of CO2 (g solute/kg CO2) Mass fraction solubility (g solute/g ﬂuid mixture) Mole fraction solubility (mole solute/mole ﬂuid mixture)

MOLECULAR WEIGHT Mn Mw MW FW

Number average molecular weight of a polymer Weight average molecular weight of a polymer Molecular weight of a chemical compound Formula weight of a chemical complex

NOMENCLATURE (C)(K)-block-coDE Lmoprac-ranR S tertZ

Clockwise rotation of the plane of polarized light Counterclockwise rotation of the plane of polarized light Block copolymer Random copolymer Dextrorotatory Entgegen (trans-conﬁguration) Levorotatory Meta isomer Ortho isomer Para isomer Racemic mixture Random copolymer Clockwise conﬁguration according to Cahn-Ingold-Prelog notation Counterclockwise conﬁguration according to Cahn-Ingold-Prelog notation Tertiary Zusammen (cis-conﬁguration)

OTHER L Nl P T x

Liter Volume in liter of ﬂuid at normal condition (273.15 K and 1.013 bar) Pressure (bar) Temperature (K) Mole fraction in liquid phase

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Table of Contents Introduction......................................................................................................................................1 Chapter 1

Solubility Data A ......................................................................................................19

Chapter 2

Solubility Data B........................................................................................................75

Chapter 3

Solubility Data C......................................................................................................151

Chapter 4

Solubility Data D ....................................................................................................271

Chapter 5

Solubility Data E......................................................................................................335

Chapter 6

Solubility Data F ......................................................................................................351

Chapter 7

Solubility Data G ....................................................................................................381

Chapter 8

Solubility Data H ....................................................................................................387

Chapter 9

Solubility Data I ......................................................................................................451

Chapter 10

Solubility Data J ....................................................................................................455

Chapter 11

Solubility Data K ..................................................................................................457

Chapter 12

Solubility Data L....................................................................................................461

Chapter 13

Solubility Data M ..................................................................................................477

Chapter 14

Solubility Data N ..................................................................................................513

Chapter 15

Solubility Data O ..................................................................................................569

Chapter 16

Solubility Data P ....................................................................................................587

Chapter 17

Solubility Data Q ..................................................................................................695

Chapter 18

Solubility Data R....................................................................................................699

Chapter 19

Solubility Data S ....................................................................................................707

Chapter 20

Solubility Data T....................................................................................................735

Chapter 21

Solubility Data U ..................................................................................................809

Chapter 22

Solubility Data V ..................................................................................................815

Chapter 23

Solubility Data W ..................................................................................................825

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Chapter 24

Solubility Data X ..................................................................................................829

Chapter 25

Solubility Data Y ..................................................................................................831

Chapter 26

Solubility Data Z....................................................................................................833

Appendix A

Density Data of Carbon Dioxide ..........................................................................835

Appendix B

List of Solutes by Molecular Formula..................................................................855

Index..............................................................................................................................................891

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List of Solutes Solute Acenaphthene 4-Acetamidophenyl acetate Acetaminophen Acetic acid Acetone Acetonitrile 17a-Acetoxy-6-dehydro-6methylprogesterone 17a-Acetoxy-6a-methylprogesterone 21-Acetoxy-17a-hydroxypregn-4-ene3,11,20-trione 4 0 -Acetoxyacetanilide p-Acetoxyacetanilide 2-Acetoxybenzoic acid Acetylsalicylic acid Acridine Adamantane Aesculetin Albumin Alizarin 4-Allyl-2-methoxyphenol Ametryne 1-Amino-2-ethylanthraquinone 1-Amino-4,5-dihydroxy-8(phenylamino)anthraquinone 1-Amino-2,3-dimethylanthraquinone 1-Amino-2,4-dimethylanthraquinone 1-Amino-4-hydroxy-2phenoxyanthraquinone 1-Amino-2-methylanthraquinone (S)-2-Amino-3-phenylpropanonic acid (S)-2-Amino-4-methylpentanoic acid (2S)-2-Amino-3-(1H-indol-3-yl)propanoic acid 4-Amino-4 0 -[bis(2-hydroxyethyl)amino]azobenzene 4-Amino-4 0 -nitroazobenzene 2-Aminoacetic acid 2-Aminobenzoic acid 4-Aminobenzoic acid ethyl ester 2-Aminoﬂuorene 1-((4-aminophenyl)azo)-2-naphthol 5-(4-aminophenylazo)-2-hydroxybenzoic acid sodium salt

Formula

MW

Data Table No.

C12H10 C10H11O3 C8H9NO2 C2H4O2 C3H6O C2H3N C24H32O4

154.21 193.20 151.16 60.05 58.08 41.05 384.51

A-1–A-3 A-11, A-12 A-4–A-6 A-7 A-8, A-9 A-10 M-6

C24H34O4 C23H30O6

386.52 402.48

M-4 C-191

C10H11NO3 C10H11NO3 C9H8O4 C9H8O4 C13H9N C10H16 C9H6O4 N/A C14H8O4 C10H12O2 C9H17N5S C16H13NO2 C20H14N2O4

193.20 193.20 180.16 180.16 179.22 136.23 178.14 N/A 240.22 164.20 227.33 251.28 346.34

A-11, A-12 A-11, A-12 A-13, A-72, A-73 A-13, A-72, A-73 A-14–A-18 A-19, A-20 A-21 A-22 C-156 E-28 A-23, A-24 A-30 C-106

C16H13NO2 C16H13NO2 C20H13NO4

251.28 251.28 331.33

A-28 A-29 C-113, C-130–C-135

C15H11NO2 C9H11NO2 C6H13NO2 C11H12N2O2

237.25 165.19 131.17 204.23

A-32, C-116, C-117 P-80 L-8 T-105

C16H20N4O2

300.36

C-89

C12H10N4O2 C2H5NO2 C7H7NO2 C9H11NO2 C13H11N C16H13N3O C13H10N3NaO3

242.24 75.07 137.14 165.19 181.23 263.30 279.23

C-113–C-115 G-8 A-25–A-27 B-11, B-12 A-31 A-33 C-157

(continued)

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Solute 2-Aminopyrazine Anguidin 1-Anilino-4,5-dihydroxy-8nitroanthraquinone 4-Anilino-3-nitrobenzenesulfonanilide p-Anisaldehyde m-Anisamide p-Anisamide Aniseed essential Oil o-Anisic acid m-Anisic acid p-Anisic acid Anisole Anthracene

9,10-Anthracenedione Anthranilic acid Anthraquinone 9,10-Anthraquinone Aquafen Arachidic acid Arachidonic acid ethyl ester Arachidyl alcohol Aroclor 1254 Arsenic tris[bis(triﬂuoroethyl)dithiocarbamate] Artemisinin Ascorbic acid L-Ascorbic acid 6-hexadecanoate Ascorbic acid 6-palmitate Ascorbyl palmitate Aspirin Atratone Atrazine Atropine 9-Azaanthracene 9-Azaﬂuorene Azobenzene Barium bis(hexaﬂuoroacetylacetonate) Beclomethasone-17,21-dipropionate Beef shank fat Behenic acid Behenyl behenate Benzaldehyde Benzeneacetic acid Benzenecarbonitrile 1,2-Benzenediol 1,3-Benzenediol 1,4-Benzenediol

Formula

MW

C4H5N3 C19H26O7 C20H12N2O6

95.10 366.41 376.32

C18H15N3O4S C8H8O2 C8H9O2N C8H9O2N N/A C8H8O3 C8H8O3 C8H8O3 C7H8O C14H10

369.39 136.15 151.16 151.16 N/A 1152.15 152.15 152.15 108.14 178.23

Data Table No. A-34 D-11 C-99

C14H8O2 C7H7NO2 C14H8O2 C14H8O2 C12H14Cl2FNO4S C20H40O2 C22H36O2 C20H42O N/A C15H12AsF18N3S6

208.21 137.14 208.21 208.21 358.21 312.53 332.52 298.55 326.50 N/A

C-148 A-35 M-17 M-18 A-36 M-19 M-20 A-37, M-21 A-38, A-39 A-18, A-27, A-40–A-63, F-40, N-49, P-65, P-66 A-64, A-65 A-25, A-26 A-64, A-65 A-64, A-65 F-32 E-4 A-66 A-67, E-5 A-68 M-15

C15H22O5 C6H8O6 C22H38O7 C22H38O7 C22H38O7 C9H8O4 C9H17N5O C8H14ClN5 C17H23NO3 C13H9N C12H9N C12H10N2 C10H2BaF12O4 C28H37ClO7 N/A C22H44O2 C44H88O2 C7H6O C8H8O2 C7H5N C6H6O2 C6H6O2 C6H6O2

282.33 176.12 414.53 414.53 414.53 180.16 211.26 215.68 289.37 179.22 167.21 182.22 551.43 521.04 N/A 340.58 649.17 106.12 136.15 103.12 110.11 110.11 110.11

A-69 A-70 A-71 A-71 A-71 A-72–A-74 A-75 A-76–A-78 A-79 A-14–A-17 C-22, C-23 A-80, A-81 B-1 B-2 B-3 B-4–B-7 B-8 B-9, B-10 P-79 B-28 D-50, P-138, P-139 D-50, R-3 D-50, H-34–H-38 (continued)

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Solute

Formula

MW

Data Table No.

Benzenemethanol Benzenepropanol 3-(2-Benzimidazolyl)-7-(diethylamino)coumarin Benzo[def]phenanthrene Benzo[ghi]perylene Benzo[j,k]ﬂuorene Benzocaine Benzoic acid

C7H8O C9H12O C20H19N3O2

108.14 136.19 333.38

B-30, B-31 P-81 C-150

C16H10 C22H12 C16H10 C9H11NO2 C7H6O2

202.25 276.33 202.25 165.19 122.12

Benzoic aldehyde Benzoin Benzonitrile 1,12-Benzoperylene 1,2-Benzophenanthrene 9,10-Benzophenanthrene 2HK1-Benzopyran-2-one 2,3-Benzopyrrole 2,3-Benzoquinoline 1,4-Benzoquinone p-Benzoquinone 2-Benzoylacetophenone m-Benzoylhydratropic acid 2-(3-Benzoylphenyl)propionic acid Benzyl alcohol Benzyl benzene N-Benzyloxycarbonyl-DL-aspartic acid N-Benzyloxycarbonyl-DL-proline N-Benzyloxycarbonyl-DL-valine Benzylpenicillin Betamethasone Betamethasone-17,21-dipropionate BHC g-BHC Bibenzyl Biphenyl

C7H6O C14H12O2 C7H5N C22H12 C18H12 C18H12 C9H6O2 C8H7N C13H9N C6H4O2 C6H4O2 C15H12O2 C16H14O3 C16H14O3 C7H8O C13H12 C12H13NO6 C13H15NO4 C13H17NO4 C16H18N2O4S C22H29FO5 C28H37FO7 C6Cl6 C6H6Cl6 C14H14 C12H10

106.12 212.24 103.12 276.33 228.29 228.29 146.14 117.15 179.22 108.09 108.09 224.25 254.28 254.28 108.14 168.23 267.24 249.26 251.28 334.39 392.46 504.59 284.80 290.83 182.26 154.21

1,1 0 -Biphenyl Bis(h5-cyclopentadienyl)iron Bis(diisopropyldithiocarbamato)lead Bis(diisopropyldithiocarbamato)palladium Bis(2,6-dimethylheptane-3,5-dionato)copper Bis(5,5-dimethylhexane2,4-dionato)copper Bis(2-ethylhexyl) phosphate Bis(2-ethylhexyl) phthalate Bis(1,1,1,5,5,5-hexaﬂuoro2,4-pentanedionato)barium

C12H10 C10H10Fe C14H28N2PbS4 C14H28N2PdS4

154.21 186.03 559.83 459.07

P-129–P-137 B-29 F-33–F-35 B-11, B-12 B-13–B-26, D-8, N-24, P-67 B-9 B-27 B-28 B-29 C-85–C-88 T-92, T-93 C-200, C-201 I-3 A-14–A-17 Q-2, Q-3 Q-2, Q-3 D-19 K-1–K-3 K-1–K-3 B-30, B-31 D-89 C-24 C-25 C-26 P-19 B-32 B-33 H-8–H-10 L-23 B-34 B-35–B-38, N-25, N-26 B-36, B-38 F-2–F-5 L-6 P-4

C18H30CuO4

373.98

C-178

C16H26CuO4

345.93

C-179

C16H35O4P C24H38O4 C10H2BaF12O4

322.42 390.56 551.43

D-41 D-84 B-1

(continued)

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Solute Bis(1,1,1,5,5,5-hexaﬂuoro2,4-pentanedionato)cobalt Bis(1,1,1,6,6,6-hexaﬂuoro pentane2,4-dionato)copper hydrate Bis(1,1,1,6,6,6-hexaﬂuoro pentane2,4-dionato)copper Bis(8-methylnonyl) hydrogen phosphate Bis(methylthioglycolato)palladium Bis(2,4-pentanedionato)cobalt Bis(2,4-pentanedionato)copper Bis(2,4-pentanedionato)copper dihydrate Bis(2,4-pentanedionato)lithium Bis(2,4-pentanedionato)manganese dihydrate Bis(2,4-pentanedionato)palladium Bis(2,4-pentanedionato)platinum Bis(2,4-pentanedionato)zinc Bis(2,2,6,6-tetramethyl-3,5heptanedionato)palladium Bis(2,2,6,6-tetramethylheptane-3,5dionato)copper Bis(1,1,1-triﬂuoropentane-2,4-dionato)copper Bis[4,4,4-triﬂuoro-1-(2-thienyl)1,3-butanedionato]copper Bis(4,4,4-triﬂuoro-1-phenylbutane-1,3dionato)copper Bis(2,2,7-trimethyloctane-3,5dionato)copper 1,1-Bis(4-chlorophenyl)-2,2,2trichloroethane 1,4-Bis(allyloxy)anthraquinone 1,4-Bis(butylamino)anthraquinone 1,4-Bis(dodecylamino)anthraquinone 1,4-Bis(ethylamino)anthraquinone 1,4-Bis(hexadecylamino)anthraquinone 1,4-Bis(isopropylamino)anthraquinone 1,4-Bis(methylamino)anthraquinone 1,4-Bis(octadecylamino)anthraquinone 1,4-Bis(octylamino)anthraquinone 1,4-Bis(pentylamino)anthraquinone 1,4-Bis(prop-2 0 -enyloxy)anthraquinone 1,4-Bis(propylamino)anthraquinone 1,8-Bis(prop-2 0 -enyloxy)anthraquinone 2,4-Bis(isopropylamino)-6-methylthio1,3,5-triazine N-[5-[Bis[2-(acetyloxy)ethyl]amino]-2-[(2bromo-4,6-initrophenyl) azo]-4ethoxyphenyl]acetamide

Formula

MW

Data Table No.

C10H2CoF12O4

473.03

C-167

C10H2CuF12O4$ xH2O C10H2CuF12O4

495.67

C-181, C-182

477.65

C-180

C20H43O4P C6H10O4PdS2 C10H14CoO4 C10H14CuO4 C10H14CoO4$2H2O C5H7LiO2 C10H14MnO4$2H2O

378.53 316.69 257.15 261.76 293.18 106.05 289.19

D-57 P-2 C-166 C-173–C-176 C-177 L-27 M-2

C10H14O4Pd C10H14O4Pt C10H14O4Zn C22H38O4Pd

304.64 393.29 263.60 472.94

P-1 P-90 Z-1 P-3

C22H38CuO4

430.09

C-183, C-184

C10H8CuF6O4

369.71

C-186

C16H8CuF6O4S2

505.89

C-185

C20H12CuF6O4

493.85

C-187

C22H38CuO4

430.09

C-188

C14H9Cl5

354.49

B-56

C20H16O4 C22H26N2O2 C38H58N2O2 C18H18N2O2 C46H74N2O2 C20H22N2O2 C16H14N2O2 C50H82N2O2 C30H42N2O2 C24H30N2O2 C20H16O4 C20H22N2O2 C20H16O4 C10H19N5S

320.34 350.46 574.88 294.35 687.09 322.41 266.30 743.21 462.67 378.51 320.34 322.41 320.34 241.36

B-53, B-54 B-40, B-41, C-161 B-42 B-43 B-44 B-45, C-107 B-46, C-92, C-93 B-47 B-48–B-51 B-52 B-53 B-55 B-54 P-116, P-117

C24H27BrN6O10

639.42

C-100–C-102

(continued)

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Solute N-[5-[Bis[2-(acetyloxy)ethyl]amino]-2-[(2bromo-4,6-initrophenyl) azo]-4methoxyphenyl]acetamide N-[5-[Bis[2-(acetyloxy)ethyl] amino]-2[(2,4-initrophenyl)azo] phenyl]acetamide N-[5-[Bis[2-(acetyloxy)ethyl] amino]-2[(2-chloro-4-nitrophenyl)azo] phenyl]propanamide N,N 0 -Bis(4,6-di-tertbutylsalicylidene)ethylenediamine N,N 0 -Bis(salicylidene)-1,2ethanediamine Bisacodyl Bismuth tris(diehtyldithiocarbamate) Bismuth tris[bis(triﬂuoroethyl)dithiocarbamate] Bisphenol A-type epoxy resin Bitumen Bitumen Cut 1 Bitumen Cut 2 Bitumen Cut 3 Blackcurrant seed oil Black pepper essential oil rac-Boc-Piperazine (S)-Boc-Piperazine 2-Bornanone Brassylic Acid Bromobenzene 4-(6-Bromo-2,4-dinitrophenylazo)-3acetylamino-6-methoxy-Nbis(acetoxyethyl)aniline N-[2-[(2-Bromo-4,6-dinitrophenyl)azo]5-(diethylamino)-4-methoxy phenyl]acetamide 1-Butanol n-Butanol (S)-tert-Butyl 3-(tert-butylcarbamoyl)piperazine-1-carboxylate Butyl acetate Butyl alcohol Butyl 2,5-dichlorobenzoate 1-Butyl-3-methylimidazolium hexaﬂuorophosphate 1-Butyl-3-methylimidazolium tetraﬂuoroborate 2-tert-Butylphenol tert-Butyl-salen p-tert-Butylcalix[4]arene p-tert-Butylcalix[6]arene

Formula

MW

Data Table No.

C23H25BrN6O10

625.38

C-102–C-103

C22H24N6O9

516.46

C-144

C23H26ClN5O7

519.93

C-140

C32H48N2O2

492.74

B-81

C16H16N2O2

268.31

S-1

C22H19NO4 C15H30BiN3S6 C15H12F18BiN3S6

361.39 N/A N/A

B-39 M-12, M-13 M-12, M-13

N/A N/A N/A N/A N/A N/A N/A C14H27N3O3 C14H27N3O3 C10H16O C13H24O4 C6H5Br C23H25BrN6O10

N/A N/A 201.00 304.00 572.00 N/A N/A 285.39 285.39 152.23 244.33 157.01 625.38

P-102 B-57, B-58 B-59 B-60 B-61 B-62 B-63 B-65 B-64 C-13 B-66 B-67 C-103, C-104

C19H21BrN6O6

509.31

C-110

C4H10O C4H10O C14H27N3O3

74.12 74.12 285.39

B-69 B-68–B-70 B-64

C6H12O2 C4H10O C11H12Cl2O2 C8H15N2 $ F6P

116.16 74.12 247.12 284.18

B-71, B-72 B-68, B-69 B-76 B-77, B-78

C8H15N2 $ BF4

226.02

B-79

C10H14O C32H48N2O2 C44H56O4 C66H84O6

150.22 492.74 648.94 973.40

B-80 B-81 B-73 B-74 (continued)

CAT4240—PRELIMS —2/11/2006—SRIDHAR—XML MODEL C – pp. 1–48

Solute p-tert-Butylcalix[8]arene C. I. Disperse Black 9 C. I. Disperse Blue 3 C. I. Disperse Blue 14 C. I. Disperse Blue 27 C. I. Disperse Blue 60 C. I. Disperse Blue 60S C. I. Disperse Blue 77 C. I. Disperse Blue 79 C. I. Disperse Blue 79:1 C. I. Disperse Blue 99 C. I. Disperse Blue 102 C. I. Disperse Blue 118 C. I. Disperse Blue 134 C. I. Disperse Blue 165:1 C. I. Disperse Blue 291 C. I. Disperse Blue 354 C. I. Disperse Brown 22 C. I. Disperse Orange 1 C. I. Disperse Orange 3 C. I. Disperse Orange 11 C. I. Disperse Orange 13 C. I. Disperse Orange 25 C. I. Disperse Orange 30 C. I. Disperse Orange 33 C. I. Disperse Red 1 C. I. Disperse Red 9 C. I. Disperse Red 11 C. I. Disperse Red 13 C. I. Disperse Red 30 C. I. Disperse Red 60 C. I. Disperse Red 82 C. I. Disperse Red 137 C. I. Disperse Red 152 C. I. Disperse Red 153 C. I. Disperse Red 167 C. I. Disperse Red 324 C. I. Disperse Red W-4BS C. I. Disperse Violet 91 C. I. Disperse Yellow 7 C. I. Disperse Yellow 16 C. I. Disperse Yellow 42 C. I. Disperse Yellow 54 C. I. Disperse Yellow 82 C. I. Disperse Yellow 86 C. I. Disperse Yellow 108 C. I. Disperse Yellow 119 C. I. Food Orange 5 C. I. Modiﬁed Yellow 119 C. I. Mordant Brown

Formula C88H112O8 C16H20N4O2 C17H16N2O3 C16H14N2O2 C22H16N2O7 C20H17N3O5 N/A C20H12N2O6 C24H27BrN6O10 C23H25BrN6O10 C20H17N3O5 C15H19N5O4S C20H14N2O4 C20H22N2O2 C19H19N7O5 C19H21BrN6O6 C31H37N3O2S N/A N/A C12H10N4O2 C15H11NO2 C22H16N4O C17H17N5O2 C19H17Cl2N5O4 N/A C16H18N4O3 C15H11NO2 C15H12N2O3 C16H17ClN4O3 C16H17ClN4O4 C20H13NO4 C21H21N5O6 N/A C19H17Cl2N5S C18H15N5SCl2 C23H26ClN5O7 N/A N/A C22H24N6O9 C19H16N4O C16H14N4O C18H15N3O4S C18H11NO3 C20H19N3O2 C16H19N3O5S N/A C15H13O4N5 C40H56 C15H12ClN5O4 C10H7NO2

MW 1297.87 300.36 296.32 266.30 420.37 379.37 379.00 376.32 639.42 625.38 379.37 365.41 346.34 322.40 425.40 509.31 515.71 399.00 N/A 242.24 237.26 352.39 323.35 450.27 N/A 314.35 237.25 268.27 348.79 364.78 331.33 439.43 430.00 418.34 404.32 519.93 426.00 469.00 516.46 316.36 278.31 369.39 289.28 333.38 365.40 429.00 327.30 536.87 361.74 173.17

Data Table No. B-75 C-89 C-90, C-91 B-46, C-92, C-93 C-94 C-95–C-97 C-98 C-99 C-100–C-102 C-103–C-104 C-95–C-97 C-105 C-106 B-45, C-107, C-108 C-109 C-110 C-111 C-112 C-113 C-113–C-115 A-32, C-116, C-117 C-118 C-113, C-119 C-113, C-120, C-121 C-122 C-123–C-125 C-126 C-127 C-128 C-129 C-113, C-130–C-135 C-136 C-137 C-138 C-139 C-140 C-141, C-142 C-143 C-144 C-145, C-146 C-108, C-147 C-148 C-149 C-150 C-151 C-152 C-153 C-29–C-40 C-154 C-155 (continued)

CAT4240—PRELIMS —2/11/2006—SRIDHAR—XML MODEL C – pp. 1–48

Solute

Formula

MW

Data Table No.

C. I. Mordant Red 11 C. I. Mordant Yellow 12 C. I. Pigment Red 1 C. I. Solvent Blue 14 C. I. Solvent Blue 35 C. I. Solvent Blue 105 C. I. Solvent Brown 1 C. I. Solvent Orange 86 C. I. Solvent Yellow 7 C. I. Solvent Yellow 114 Cafesterol Cafestol Caffeic acid Caffeine Calciferol Calix[4]arene Calix[4]arene-25,26,27,28-tetrol Camphor Canola oil Capric alcohol Caproic acid 6-Caprolactam Capsaicin Carbamazepine Carbamazepine Polymorph I Carbamazepine Polymorph III Carbazole

C14H8O4 C13H10N3NaO3 C16H11N3O3 C24H30N2O2 C22H26N2O2 C18H18N2O2 C16H14N4 C14H8O4 C12H10N2O C18H11NO3 C20H28O3 C20H28O3 C9H8O4 C8H10N4O2 C28H44O C28H24O4 C28H24O4 C10H16O N/A C10H22O C6H12O2 C10H19NO C18H27NO3 C15H12N2O C15H12N2O C15H12N2O C12H9N

240.22 279.23 293.28 378.51 350.46 294.35 262.31 240.21 198.22 289.28 316.43 316.43 180.16 194.19 396.65 424.49 424.49 152.23 N/A 158.28 116.16 169.27 305.41 236.27 236.27 236.27 167.21

N-Carbobenzoxy aspartic acid N-Carbobenzoxyproline N-Carbobenzoxyvaline 4-Carbomethoxy phenol Carbonyl(h5-cyclopentadienyl)(triphenylphosphine)cobalt Carbonyl-p-cyclopentadienyl(triphenylphosphine)cobalt Carbonyl-p-cyclopentadienyl(tris(4-trimethylsilylphenyl) phosphine)cobalt Carbonyldiiodo(h5-Cyclopentadienyl)cobalt Carbonyldiiodo(h5-Trimethylsilyl cyclopentadienyl)cobalt 2-Carboxyaniline 2-Carboxypyrazine 3-Carboxypyridine

C12H13NO6 C13H15NO4 C13H17NO4 C8H8O3 C24H20CoOP

267.24 249.26 251.28 152.15 413.31

C-156 C-157 P-18 B-52 B-40, B-41, C-161 B-43 C-162 D-44, D-45 H-48, H-49 C-149 C-1 C-1 C-2 C-3–C-11 V-7, V-8 C-12 C-12 C-13 C-14 D-9 H-26, H-27 C-15 C-16–C-18 C-19, C-20 C-21 C-21 A-61, A-63, C-22, C-23, P-68 C-24 C-25 C-26 M-53 C-27

C24H20CoOP

413.31

C-27

C33H45CoOPSi3

630.87

C-28

C6H5CoI2O

405.85

C-213

C9H13CoI2OSi

477.82

C-214

C7H7NO2 C5H4N2O2 C6H5NO2

137.14 124.10 123.11

C40H56 C40H56 C10H14O

536.87 536.87 150.22

A-25, A-26 P-128 N-67, N-68, N-69, N-70, N-71 C-29–C-40 C-29–C-40 C-41

b-Carotene b,b-Carotene Carvacrol

(continued)

CAT4240—PRELIMS —2/11/2006—SRIDHAR—XML MODEL C – pp. 1–48

Solute L-Carvone (R)-(K)-Carvone Castor oil Catechaldehyde Catechin (C)-Catechin Catechol Ce(thd)4 Ce(tod)4 Cerium tetrakis(2,2,6,6-tetramethyl-3,5heptanedionate) Cerium tetrakis(2,2,7-trimethyl-3,5octanedionate) Cetyl alcohol Cetyl behenate Chloramphenicol Chlorobenzene Chloro(h5-cyclopentadienyl)dioxomolybdenum Chloro(h5-Trimethylsilylcyclopentadienyl)dioxomolybdenum 2-Chlorobiphenyl 4-Chlorobiphenyl 4-Chlorophenol p-Chlorophenol 2-Chloro-4,6-bis(ethylamino)-1,3,5triazine 2-Chloro-4,6-bis(isopropylamino)1,3,5-triazine 2-Chloro-4-ethylamino-6isopropylamino-1,3,5-triazine 2-Chloro-1-methylbenzene 2-Chloro-1,3-pyrimidine 5-(4-Chloro-2-nitrophenylazo)3-cyano-1-ethyl-6-hydroxy4-methyl-1H-pyridin-2-one 6-Chloro-1,2a-methylene-6-dehydro-17ahydroxyprogesterone acetate 7-Chloro-1-methyl-5-phenyl-3H1,4-benzodiazepin-2(1H)-one 7-Chloro-2 0 ,4,6-trimethoxy-6 0 methylspiro[benzofuran-2(3H),1 0 [2]cyclohexene]-3,4 0 -dione 9a-Chloro-16b-methylprednisolone 17,21dipropionate 2,2 0 -[[4-[(2-Chloro-4-nitrophenyl)azo]phenyl]imino]bisethanol 1-(4-Chlorophenyl)-4,4-dimethyl3-(1,2,4-triazol-1-ylmethyl)pentan-3-ol Chlorophyllian pigments

Formula

MW

Data Table No.

C10H14O C10H14O N/A C7H6O3 C15H14O6 C15H14O6 C6H6O2 C44H76CeO8 C44H76CeO8 C44H76CeO8

150.22 150.22 N/A 138.12 290.27 290.27 110.11 873.20 873.20 873.20

C-42 C-42 C-43 P-126 C-44 C-44 P-138, P-139 C-45 C-46 C-45

C44H76CeO8

873.20

C-46

C16H34O C38H76O2 C11H12Cl2N2O5 C6H5Cl C5H5ClMoO2

242.44 565.01 323.13 112.56 228.48

C-47–C-51 P-14 C-52 C-53 C-213

C8H13Cl2MoO2Si

336.91

C-214

C12H9Cl C12H9Cl C6H5ClO C6H5ClO C7H12ClN5

188.66 188.66 128.56 128.56 201.66

C-54–C-56 C-57–C-59 C-61 C-61 S-4

C9H16ClN5

229.71

P-121

C8H14ClN5

215.68

A-76, A-77, A-78

C7H7Cl C4H3ClN2 C15H12ClN5O4

126.58 114.53 361.74

C-60 C-63 C-154

C24H29ClO4

416.94

C-216

C16H13ClN2O

284.74

D-13

C17H17ClO6

352.77

G-10

C28H37ClO7

521.04

B-2

C16H17ClN4O4

364.78

C-129

C16H22ClN3O

307.82

T-3

N/A

N/A

C-62 (continued)

CAT4240—PRELIMS —2/11/2006—SRIDHAR—XML MODEL C – pp. 1–48

Solute 2-Chloropyrimidine Chlorothalonil Cholecalciferol Cholest-5-en-3b-ol Cholesterol Cholesterol acetate Cholesterol benzoate Cholesterol butanoate Cholesterol butyrate Cholesteryl acetate Cholesteryl benzoate Cholesteryl butyrate Chromium cis-tris(1,1,1-triﬂuoroacetylacetonate) Chromium trans-tris(1,1,1triﬂuoroacetylacetonate) Chromium tris(acetylacetonate) Chromium tris(3-bromoacetylacetonate) Chromium tris(hexaﬂuoroacetylacetonate) Chromium tris(2,2,6,6-tetramethylheptane3,5-dionate) Chrysene Cineole 1,8-Cineole trans-Cinnamic acid Citral Clove buds extract Co(acac)2 Co(acac)3 Co(hfa)2 Cobalt bis(acetylacetonate) Cobalt bis(hexaﬂuoroacetylacetonate) Cobalt tris(acetylacetonate) Cobalt tris(diethyldithiocarbamate) Cobalt tris[bis(triﬂuoroethyl)dithiocarbamate] Cocoa Butter Codeine Coenzyme Q10 Copper bis(acetylacetonate) Copper bis(acetylacetonate) dihydrate Copper bis[bis(triﬂuoroethyl)dithiocarbamate] Copper bis(dibutyldithiocarbamate) Copper bis(diethyldithiocarbamate) Copper bis(dihexyldithiocarbamate) Copper bis(dipentyldithiocarbamate) Copper bis(dipropyldithiocarbamate) Copper bis(hexaﬂuoroacetylacetonate)

Formula

MW

Data Table No.

C4H3ClN2 C8Cl4N2 C27H44O C27H46O C27H46O C29H48O2 C34H50O2 C31H52O2 C31H52O2 C29H48O2 C34H50O2 C31H52O2 C15H12CrF9O6

114.53 265.91 384.64 386.65 386.65 428.69 490.76 456.74 456.74 428.69 490.76 456.74 511.24

C-63 T-15 V-9, V-10 C-64–C-74 C-64–C-74, C-79,P-113 C-75 C-76, C-77 C-78 C-78 C-75 C-76, C-77 C-78 C-83

C15H12CrF9O6

511.24

C-84

C15H21CrO6 C15H18Br3CrO6 C15H3CrF18O6

349.32 586.01 N/A

C-80, M-13 C-81 M-13

C33H57CrO6

601.81

C-82

C18H12 C10H18O C10H18O C9H8O2 C10H16O N/A C10H14CoO4 C15H21CoO6 C10H2CoF12O4 C10H14CoO4 C10H2CoF12O4 C15H21CoO6 C15H30CoN3S6 C15H12CoF18N3S6

228.29 154.25 154.25 148.16 152.23 N/A 257.15 356.26 473.03 257.15 473.03 356.26 N/A N/A

C-85–C-88 C-158, C-159 C-158, C-159 C-160 C-163, C-164, L-19 C-165 C-166 C-168 C-167 C-166 C-167 C-168 M-12, M-13 M-12, M-13, M-15

N/A C18H21NO3 C59H90O4 C10H14CuO4 C10H14CoO4$2H2O C10H8CuF12N2S4

N/A 299.36 863.34 261.76 293.18 575.95

C18H36CuN2S4 C10H20CuN2S4 C26H52CuN2S4 C22H44CuN2S4 C14H28CuN2S4 C10H2CoF12O4

472.28 360.07 584.50 528.39 416.18 N/A

C-169, C-170 C-171 C-172 C-173–C-176 C-177 C-189, M-12, M-13, M-15 C-189 C-189, M-12, M-13 C-189 C-189 C-189 M-13 (continued)

CAT4240—PRELIMS —2/11/2006—SRIDHAR—XML MODEL C – pp. 1–48

Solute Copper bis(thenoyltriﬂuoroacetonate) Copper bis(2,6-dimethylheptane3,5-dionate) Copper bis(5,5-dimethylhexane2,4-dionate) Copper bis(1,1,1,6,6,6-hexaﬂuoroacetylacetonate) Copper bis(1,1,1,6,6,6-hexaﬂuoroacetylacetonate) hydrate Copper bis(2,2,6,6-tetramethylheptane3,5-dionate) Copper bis(1,1,1-triﬂuoroacetylacetonate) Copper bis(1,1,1-triﬂuoro-4-phenylbutane2,4-dionate) Copper bis(2,2,7-trimethyloctane3,5-dionate) Copper pyrrolidinedithiocarbamate Copper(II) hydrogen arsenate Cortisol Cortisone 21-acetate Cortisone acetate 2-Coumaric acid 3-Coumaric acid 4-Coumaric acid o-Coumaric acid m-Coumaric acid p-Coumaric acid Coumarin Cr(acac)3 Cr(acac-Br)3 cis-Cr(tfa)3 trans-Cr(tfa)3 Cr(thd)3 4-Cresol p-Cresol Cu(acac)2 Cu(dibm)2 Cu(dmhd)2 Cu(hfa)2 Cu(hfa)2$H2O Cu(tfa)2 Cu(tfbzm)2 Cu(thd)2 Cu(tod)2 Cupuacu seed fat Cyanobenzene N-[2-[(2-Cyano-4,6-dinitrophenyl)azo]5-(diethylamino)phenyl] acetamide

Formula

MW

Data Table No.

C16H8CuF6O4S2 C18H30CuO4

505.89 373.98

C-185 C-178

C16H26CuO4

345.93

C-179

C10H2CuF12O4

477.65

C-180

C10H2CuF12O4$ H2O C22H38CuO4

495.67

C-181, C-182

430.09

C-183, C-184

C10H8CuF6O4

369.71

C-186

C20H12CuF6O4

493.85

C-187

C22H38CuO4

430.09

C-188

C10H16CuN2S4 AsHCuO4 C21H30O5 C23H30O6 C23H30O6 C9H8O3 C9H8O3 C9H8O3 C9H8O3 C9H8O3 C9H8O3 C9H6O2 C15H21CrO6 C15H18Br3CrO6 C15H12CrF9O6 C15H12CrF9O6 C33H57CrO6 C7H8O C7H8O C10H14CuO4 C18H30CuO4 C16H26CuO4 C10H2CuF12O4 C10H2CuF12O4$ H2O C10H8CuF6O4 C20H12CuF6O4 C22H38CuO4 C22H38CuO4 N/A C7H5N C19H19N7O5

356.04 203.47 362.46 402.48 402.48 164.16 164.16 164.16 164.16 164.16 164.16 146.14 349.32 586.01 511.24 511.24 601.81 108.14 108.14 261.76 373.98 345.93 477.65 495.67

C-189 C-190 H-33 C-191 C-191 C-192, C-193 C-194, C-195 C-196–C-199 C-192, C-193 C-194, C-195 C-196–C-199 C-200, C-201 C-80 C-81 C-83 C-84 C-82 C-202 C-202 C-173–C-176 C-178 C-179 C-180 C-181, C-182

369.71 493.85 430.09 430.09 N/A 103.12 425.40

C-186 C-187 C-183, C-184 C-188 C-203 B-28 C-109

(continued)

CAT4240—PRELIMS —2/11/2006—SRIDHAR—XML MODEL C – pp. 1–48

Solute 4-[N-(2-Cyanoethyl)-N-ethylamino]4 0 -nitroazobenzene 2-Cyanonaphthalene 1-Cyanooctadecane b-Cyclodextrin heneicosaacetate a-Cyclodextrin octadecaacetate g-Cyclodextrin tetracosaacetate 1,5,9-Cyclododecatriene Cyclododecene Cyclohexanol Cyclohexanone Carbonyl(h5-cyclopentadienyl) [tris(4trimethylsilylphenyl)phosphine] cobalt Cyclopentadienylmanganese tricarbonyl Cyclotrimethylenetrinitramine Cyproterone acetate 2,4-D Danthron DDT 4,4 0 -DDT Decahydro-3,5,1,7-[1,2,3,4]butanetetraylnaphthalene Decahydronaphthalene Decalin (all-E)K2-(3,7,11,15,19,23, 27,31, 35,39-Decamethyl-2,6,10,14,18,22, 26,30, 34,38-tetracontadecaenyl)-5,6dimethoxy-3-methyl-p-benzo quinone Decamethylene glycol Decane 1,10-Decanediol 1-Decanol Decyl 2,5-dichlorobenzoate Decyl alcohol 9,10-Deepithio-9,10didehydroacanthifolicin 1,2-Dehydrocortisone 1,2-Dehydrohydrocortisone 3-[(6-Deoxy-a-L-mannopyranosyl)oxy]1,8-dihydroxy-6-methyl anthaquinone Dextrose [3,5-Di(triﬂuoromethyl)phenyl]dibenzo16-crown-5-oxyacetic acid Diacetoxyscirpenol Diadamantane Diamantane 1,4-Diamino-2-methoxyanthraquinone 2,6-Diamino-3-phenylazopyridine

Formula

MW

C17H17N5O2

323.35

C11H7N C19H37N C84H112O56 C72H96O48 C96H128O64 C12H18 C12H22 C6H10O C6H12O C33H45CoOPSi3

153.18 279.50 2017.75 1729.50 2306.03 162.27 166.30 98.14 100.16 630.87

Data Table No. C-113, C-119 C-204 N-87 C-206 C-205 C-207 C-209 C-208 C-210 C-211 C-28

C8H5MnO3 C3H6N6O6 C24H29ClO4 C8H6Cl2O3 C14H8O4 C14H9Cl5 C14H9Cl5 C14H20

204.06 222.12 416.94 221.04 240.21 354.49 354.49 188.31

C-212 C-215 C-216, M-5 D-32–D-35, P-43 D-46–D-48 B-56, D-1 B-56 D-12

C10H18 C10H18 C59H90O4

138.25 138.25 863.34

D-2 D-2 C-172

C10H22O2 C10H22 C10H22O2 C10H22O C17H24Cl2O2 C10H22O C44H68O13

174.28 142.28 174.28 158.28 331.28 158.28 805.00

D-7 D-3–D-6 D-7, D-8 D-9 D-10 D-9 O-20

C21H26O5 C21H28O5 C21H20O9

358.43 360.44 416.38

P-110 P-109 F-44

C6H12O6 C29H26F6O8

180.16 616.51

G-4, G-5 L-2

C19H26O7 C14H20 C14H20 C15H12N2O3 C11H11N5

366.41 188.31 188.31 268.27 213.24

D-11 D-12 D-12 C-127 P-74 (continued)

CAT4240—PRELIMS —2/11/2006—SRIDHAR—XML MODEL C – pp. 1–48

Solute 1,4-Diaminoanthraquinone, N,N 0 -mixed 2-hydroxyethyl and methyl derivatives 1,4-Diamino-N-(3-methoxypropyl)anthraquinone-2,3-dicarboximide 9,10-Diazaanthracene 4,5-Diazaphenanthrene Diazepam 5H-Dibenz[b,f]azepine-5-carboxamide Dibenz[de,kl]anthracene 1,2,3,4-Dibenznaphthalene Dibenzo-16-crown-5-oxyacetic acid Dibenzo-24-Crown-8 Dibenzo-27-Crown-9 Dibenzo-30-Crown-10 Dibenzofuran Dibenzopyrazine Dibenzopyrrole Dibenzothiophene Dibenzoylmethane Dicaprylyl ether 3,4-Dichloraniline 2,2 0 -Dichloro-1,1 0 -biphenyl 4,4 0 -Dichloro-1,1 0 -biphenyl 2,4-Dichloro-1-naphthalenol 2,4-Dichloro-1-naphthol 3-[[4-[[5,6(or 6,7)-Dichloro-2benzothiazolyl]azo]phenyl]ethylamino] propanenitrile 3-[[4-[[5,6(or 6,7)-Dichloro-2benzothiazolyl]azo]-3-methylphenyl]ethylamino]propanenitrile 4-[(2,6-Dichloro-4-nitrophenyl)azo]-N(cyanoethyl)-N-(acetoxyethyl) aniline 3,4-Dichlorobenzenamine 1,2-Dichlorobenzene 2,5-Dichlorobenzoic acid 3,3,4,4,5,5, 6,6,7,7,8,8,8-tridecaﬂuorooctyl ester 2,5-Dichlorobenzoic acid butyl ester 2,5-Dichlorobenzoic acid n-propyl ester 2,2 0 -Dichlorobiphenyl 4,4 0 -Dichlorobiphenyl Dichlorobis(triphenylphosphine)nickel(II) Dichlorobis(h5-cyclopentadienyl)titanium Dichlorobis(h5-cyclopentadienyl)zirconium Dichlorobis[h5-(trimethylsilyl)cyclopentadienyl]zirconium

Formula

MW

Data Table No.

C17H16N2O3

296.32

C-90, C-91

C20H17N3O5

379.37

C-95–C-97

C12H8N2 C12H8N2 C16H13ClN2O C15H12N2O C20H12 C18H12 C21H24O8 C24H32O8 C26H36O9 C28H40O10 C12H8O C12H8N2 C12H9N C12H8S C15H12O2 C16H34O C6H5Cl2N C12H8Cl2 C12H8Cl2 C10H6Cl2O C10H6Cl2O C18H15N5SCl2

180.21 180.21 284.74 236.27 252.31 228.29 404.42 448.51 492.56 536.61 168.19 180.21 167.21 184.26 224.25 242.44 162.02 223.10 223.10 213.06 213.06 404.32

P-73 P-72 D-13 C-19–C-21 P-40–P-42 T-92, T-93 L-2 D-14 D-15 D-16 D-17 P-73 C-22, C-23 D-18 D-19 D-83 P-43 D-22–D-24 D-25–D-28 D-30 D-30 C-139

C19H17Cl2N5S

418.34

C-138

C19H17Cl2N5O4

450.27

C-113, C-120, C-121

C6H5Cl2N C6H4Cl2 C15H7Cl2F13O2

162.02 147.00 537.10

P-43 D-21 T-61

C11H12Cl2O2 C10H10Cl2O2 C12H8Cl2 C12H8Cl2 C36H30Cl2NiP2

247.12 233.09 223.10 223.10 654.20

B-76 P-123 D-22–D-24 D-25–D-28 D-29

C10H10Cl2Ti

249.00

T-43

C10H10Cl2Zr

292.32

C-213

C16H26Cl2Si2Zr

434.00

C-214

(continued)

CAT4240—PRELIMS —2/11/2006—SRIDHAR—XML MODEL C – pp. 1–48

Solute 4,4 0 -Dichlorodiphenyltrichloroethane 2,2-Dichloro-N-((1R,2R)-1,3-dihydroxy1-(4-nitrophenyl)propan-2-yl)acetamide 2,2-Dichloro-N-[(1S,2R)1-(ﬂuoromethyl)-2-hydroxy-2[4-(methyl sulfonyl)phenyl]ethyl]acetamide 2,2-Dichloro-N-[2-hydroxy1-(hydroxymethyl)-2-[4-(methylsulfonyl) phenyl]ethyl]acetamide 2,4-Dichlorophenol 2,4-Dichlorophenoxy acetic acid 2,4-Dichlorophenoxy ethanoic acid 2-[4-(2,4-Dichlorophenoxy)phenoxy]propanoic acid 3-(3,4-Dichlorophenyl)1-methoxy-1-methylurea 1-[2-(2,4-Dichlorophenyl)-2[(2,4-dichlorophenyl)methoxy]ethyl]1H-imidazole Diclofenac Sodium Diclofop Diclofopmethyl Didodecanoyl glycerol Didodecylamine Didodecylphosphine Didodecylsulfane Didodecylthioether Diethyl 1,2-benzenedicarboxylate Diethyl methyl carbinol Diethyl phthalate Diethylamine diethyldithiocarbamate 2-(Diethylamino)-2 0 ,6 0 -acetoxylidide 2-(Diethylamino)-N-(2,6-dimethylphenyl)acetamide 2-(Diethylamino)ethyl-4-aminobenzoate N,N 0 -Diethylcarbanilide N,N-Diethyl-N,N 0 -diphenylurea N,N-Diethyldithiocarbamic acid diethylamine salt 3(6),3 0 (6 0 )-Diﬂuorodibenzo-16-crown5-oxyacetic acid Dihexyl(diethylcarbamoyl)methylphosphonate Dihexyl-(N,N-diethylcarbamoyl)methylphosphonate

Formula

MW

Data Table No.

C14H9Cl5

354.49

D-1

C11H12Cl2N2O5

323.13

C-52

C12H14Cl2FNO4S

358.21

F-32

C12H15Cl2NO5S

356.22

T-39

C6H4Cl2O C8H6Cl2O3 C8H6Cl2O3 C15H12Cl2O4

163.00 221.04 221.04 327.16

D-31 D-32–D-35, P-43 D-32–D-35 P-43

C9H10Cl2N2O2

249.09

P-43

C18H14Cl4N2O

416.12

M-55

C14H11Cl2NO2$Na C15H12Cl2O4 C16H14Cl2O4 C27H52O5 C24H51N C24H51P C24H50S C24H50S C12H14O4 C6H14O C12H14O4 C5H11NS2$C4H11N

318.13 327.16 341.19 456.70 353.67 370.64 370.72 370.72 222.24 102.17 222.24 222.41

D-36 P-43 P-43 D-58 D-37 D-38 D-39 D-39 D-42 M-51 D-42 D-40

C14H22N2O C14H22N2O

234.34 234.34

L-9 L-9

C13H20N2O2 C17H20N2O C17H20N2O C5H11NS2$C4H11N

236.31 268.35 268.35 222.41

P-111 E-16 E-16 D-40

C21H22F2O8

440.40

L-2

C18H38NO4P

363.47

D-43

C18H38NO4P

363.47

D-43

(continued)

CAT4240—PRELIMS —2/11/2006—SRIDHAR—XML MODEL C – pp. 1–48

Solute N,N-Dihexyl-1-hexanamine [2-[[4-(Dihexylamino)-2-methylphenyl] methylene]-1,1-dioxidobenzo[b]thien3(2H)-ylidene] propanedinitrile 1,2-Dihydroacenaphthylene 1,4-Dihydro-2,6-dimethyl-4-(3nitrophenyl)-3,5-pyridine dicarboxylic acid 2-methoxyethyl 1-methylethyl ester 1,4-Dihydro-2,6-dimethyl-4(3-nitrophenyl)-3,5-pyridinedicarboxylic acid ethyl methyl ester [2R[2R*(4R*,8R*)]]-3,4-Dihydro-2,8dimethyl-2-(4,8,12-trimethyl tridecyl)2H-benzopyran-6-ol 3,7-Dihydro-3,7-dimethyl-1H-purine2,6-dione 3,4-Dihydro-5-methoxy-1(2H)naphthalenone 3,4-Dihydro-6-methoxy-1(2H)naphthalenone 3,4-Dihydro-7-methoxy-1(2H)naphthalenone (2R)-3,4-Dihydro-2,5,7,8-tetramethyl-2[(4R,8R)-4,8,12-trimethyl tridecyl]2H-1-benzopyran-6-ol 1,8-Dihydroxyanthracen-9(10H)-one 1,2-Dihydroxyanthraquinone 1,4-Dihydroxyanthraquinone 1,8-Dihydroxyanthraquinone 1,8-Dihydroxyanthrone 1,8-Dihydroxy-9-anthrone 3,4-Dihydroxybenzaldehyde 1,3-Dihydroxybenzene o-Dihydroxybenzene m-Dihydroxybenzene p-Dihydroxybenzene 3,4-Dihydroxybenzeneacrylic acid 2,5-Dihydroxybenzoic acid 3,4-Dihydroxybenzoic acid 1,8-Dihydroxy-2,7-bis (prop-1 0 -enyl)anthraquinone 3,4-Dihydroxycinnamic acid 6,7-Dihydroxycoumarin 7,8-Dihydroxyﬂavone 1,8-Dihydroxy-4-(pK2-hydroxyethylanilino)-5-nitroanthraquinone 1,4-Dihydroxy-3-methyl-9Hthioxanthen-9-one 1,4-Dihydroxy-3-methylthioxanthone

Formula

MW

Data Table No.

C18H39N C31H37N3O2S

269.51 515.71

T-66 C-111

C12H10 C21H26N2O7

154.21 418.44

A-1, A-2 N-74

C18H20N2O6

360.36

N-75

C27H46O2

402.65

T-49, T-50

C7H8N4O2

180.16

T-30–T-34

C11H12O2

176.21

M-28

C11H12O2

176.21

M-29

C11H12O2

176.21

M-30

C29H50O2

430.71

T-44–T-48

C14H10O3 C14H8O4 C14H8O4 C14H8O4 C14H10O3 C14H10O3 C7H6O3 C6H6O2 C6H6O2 C6H6O2 C6H6O2 C9H8O4 C7H6O4 C7H6O4 C20H16O4

226.23 240.22 240.21 240.21 226.23 226.23 138.12 110.11 110.11 110.11 110.11 180.16 154.12 154.12 320.34

D-49 C-156 D-44, D-45 D-46–D-48 D-49 D-49 P-126 R-3 D-50 D-50 D-50 C-2 G-2 P-127 D-51

C9H8O4 C9H6O4 C15H10O4 C22H16N2O7

180.16 178.14 254.24 420.37

C-2 A-21 D-52 C-94

C14H10O3S

258.29

D-53

C14H10O3S

258.29

D-53 (continued)

CAT4240—PRELIMS —2/11/2006—SRIDHAR—XML MODEL C – pp. 1–48

Solute 7,8-Dihydroxy-2-phenyl-4-benzopyrone 17,21-Dihydroxy-1,4-pregnadiene3,11,20-trione 1,8- Dihydroxy-2-(prop-2 0 -enyl)anthracen-9-one 1,8- Dihydroxy-2-(prop-2 0 -enyl)anthrone 1,6-Dihydroxyxanthen-9-one 1,6-Dihydroxyxanthone Diiodomethyl p-tolyl sulfone Diisodecyl phosphoric acid Dilaurin Dilaurylamine Dilaurylphosphine 1,2-Dimethoxybenzene 1,4-Dimethoxybenzene 2,4-Dimethoxy-6-sulfonylamido1,3-diazine 2,6-Dimethoxy-4-sulfanilamidopyrimidine Dimethyl 2H-1-benzopyran2,3-dicarboxylate Dimethyl 6-bromo-2HK1-benzopyran2,3-dicarboxylate Dimethyl 6-bromo-2H-chromene2,3-dicarboxylate Dimethyl 3H-benzo[f]chromene2,3-dicarboxylate Dimethyl 2H-chromene2,3-dicarboxylate Dimethyl 3H-naphtho[2,1-b]pyran2,3-dicarboxylate 3,7-Dimethyl-1,6-octadien-3-ol 3,7-Dimethyl-2,6-octadienal N1-(4,6-Dimethyl-2-pyrimidinyl)sulfanilamide 2,8-Dimethyl-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine (all-E)K3,7-Dimethyl-9(2,6,6-trimethyl-1-cyclohexen-1-yl)2,4,6,8-nonatetraen-1-ol 4-Dimethylaminoazobenzene p-Dimethylaminoazobenzene 5-[3-(Dimethylamino)propyl]-10,11dihydro-5H-dibenz[b,f]azepine hydrochloride 2,5-Dimethylaniline 2,5-Dimethylbenzenamine 2-(1,1-Dimethylethyl)phenol 2,3-Dimethylhexane N,N-Dimethylindoaniline

Formula

MW

Data Table No.

C15H10O4 C21H26O5

254.24 358.43

D-52 P-110

C17H14O3

266.30

D-54

C17H14O3 C13H8O4 C13H8O4 C8H8I2O2S C20H43O4P C27H52O5 C24H51N C24H51P C8H10O2 C8H10O2 C12H14N4O4S

266.30 228.20 228.20 422.02 378.53 456.70 353.67 370.64 138.16 138.16 310.33

D-54 D-55 D-55 D-56 D-57 D-58 D-37 D-38 D-59 D-60 S-39, S-40

C12H14N4O4S

310.33

S-39, S-40

C13H12O5

284.23

D-64

C13H11BrO5

327.13

D-65

C13H11BrO5

327.13

D-65

C17H14O5

298.29

D-76

C13H12O5

284.23

D-64

C17H14O5

298.29

D-76

C10H18O C10H16O C12H14N4O2S

154.25 152.23 278.33

L-21, L-22 C-163, C-164, L-19 S-42, S-43

C17H18N2

250.34

T-104

C20H30O

286.45

R-5

C14H15N3 C14H15N3 C19H24N2HCl

225.29 225.29 316.87

D-61, D-62 D-61, D-62 I-1

C8H11N C8H11N C10H14O C8H18 C14H14N2O

121.18 121.18 150.22 114.23 226.27

D-63 D-63 B-80 D-66 P-77, P-78 (continued)

CAT4240—PRELIMS —2/11/2006—SRIDHAR—XML MODEL C – pp. 1–48

Solute

Formula

MW

Data Table No.

2,3-Dimethylnaphthalene

C12H12

156.22

2,6-Dimethylnaphthalene

C12H12

156.22

2,7-Dimethylnaphthalene 2,5-Dimethylphenol 2,6-Dimethylphenol 3,4-Dimethylphenol 1,3-Dimethylxanthine 3,7-Dimethylxanthine Di-n-dodecylamine 2,4-Dinitrophenol 2,5-Dinitrophenol Dinonyl 1,2-benzenedicarboxylate Dinonyl phthalate Dioctyl ether Dioctyl phthalate Diolein 1,3-Diphenyl-1,3-propanedione 5,5-Diphenyl-2,4-imidazolidinedione Diphenylamine N,N-Diphenylbenzenamine 1,3-Diphenylbenzene Diphenyldiazene Diphenylene oxide Diphenylene sulﬁde 1,2-Diphenylethane 5,5-Diphenylhydantoin Diphenylmethane Di-tert-butyl 3H-benzo[f]chromene2,3-dicarboxylate Di-tert-butyl 3H-naphtho[2,1-b]pyran2,3-dicarboxylate DMDT Docosahexaenoic acid ethyl ester (all-Z)-4,7,10,13,16,19-Docosahexaenoic acid ethyl ester Docosane Docosanoic acid Docosyl docosanoate 6,7,9,10,12,13,20,21,23,24, 26,27-Dodecahydrodibenz[b,n] [1,4,7,10,13,16,19,22]octaoxacyclotetracosin Dodecane Dodecanoic acid Dodecyl 3,4,5-trihydroxybenzoate Dodecyl gallate (S)-2-(Dodecylthio)-N-(4-hydroxy-2,3,5trimethylphenyl)-2-phenyl acetamide

C12H12 C8H10O C8H10O C8H10O C7H8N4O2 C7H8N4O2 C24H51N C6H4N2O5 C6H4N2O5 C26H42O4 C26H42O4 C16H34O C24H38O4 C39H72O5 C15H12O2 C15H12N2O2 C12H11N C18H15N C18H14 C12H10N2 C12H8O C12H8S C14H14 C15H12N2O2 C13H12 C23H26O5

156.22 122.16 122.16 122.16 180.16 180.16 353.67 184.11 184.11 418.61 418.61 242.44 390.56 620.99 224.25 252.27 169.22 245.32 230.30 182.22 168.19 184.26 182.26 252.27 168.23 382.46

D-67–D-69, N-27, P-69 D-69–D-74, N-28, P-70 D-74, D-75 X-1 X-2 X-3 T-35–T-38 T-30–T-34 D-37 D-77 D-78 D-79–D-82 D-79–D-82 D-83 D-84 D-85 D-19 P-82 D-86–D-88 T-91 T-6 A-80, A-81 D-17 D-18 B-34 P-82 D-89, N-29 D-20

C23H26O5

382.46

D-20

C16H15Cl3O2 C24H36O2 C24H36O2

345.65 356.54 356.54

M-22 D-90, D-91 D-90, D-91

C22H46 C22H44O2 C44H88O2 C24H32O8

310.60 340.58 649.17 448.51

D-92 B-4–B-7 B-8 D-14

C12H26 C12H24O2 C19H30O5 C19H30O5 C29H43NO2S

170.33 200.32 338.44 338.44 469.72

D-93 L-4, L-5 D-94 D-94 E-1

(continued)

CAT4240—PRELIMS —2/11/2006—SRIDHAR—XML MODEL C – pp. 1–48

Solute Dotriacontane Eﬂucimibe Eicosane Eicosanoic acid 1-Eicosanol Eicosapentaenoic acid ethyl ester (all Z)-5,8,11,14,17-Eicosapentaenoic acid ethyl ester (all Z)-5,8,11,14-Eicosatetraenoic acid ethyl ester Eicosatrienoic acid ethyl ester Emodin Endrin Epicatechin Epicatechol 1,8-Epoxy-p-menthane 12,13-Epoxytrichothec-9-ene-3a,4b, 15-triol 4,15-diacetate Ergocalciferol (3b,22E)-Ergosta-5,7,22-trien-3-ol Ergosterol Erythromycin Esculetin Estra-1,3,5(10)-triene-3,17-diol b-Estradiol 1,2-Ethanediol 4-(4-Ethoxyanilino)-N,N-dimethyl3-nitrobenzenesulfonamide Ethyl 4-aminobenzoate Ethyl 4-hydroxybenzoate Ethyl arachidonate Ethyl centralite Ethyl docosahexaenoate Ethyl eicosapentaenoate Ethyl hexadecanoate Ethyl myristate Ethyl octadecanoate Ethyl oleate Ethyl palmitate Ethyl stearate 3-[Ethyl[3-methyl-4-[(5-nitro-2-thiazolyl)azo]phenyl]amino]-1,2-propanediol 2-Ethyl-1-hexanol 2-Ethyl-1-hydroxyanthracen-9(10H)-one 1-Ethyl-6-hydroxy-4-methyl-5-(2-nitrophenylazo)-2-oxo-1,2-dihydropyridine-3-carbonitrile 2-Ethylamino-4-isopropylamino6-methoxy-s-triazine

Formula

MW

Data Table No.

C32H66 C29H43NO2S C20H42 C20H40O2 C20H42O C22H34O2 C22H34O2

450.87 469.72 282.55 312.53 298.55 330.50 330.50

D-95–D-98 E-1 E-2, E-3 E-4 A-67, E-5 E-6 E-6

C22H36O2

332.52

A-66

C22H38O2 C15H10O5 C12H8Cl6O C15H14O6 C15H14O6 C10H18O C19H26O7

334.54 270.24 380.91 290.27 290.27 154.25 366.41

E-7 E-8 E-9 E-10 E-10 C-158, C-159 D-11

C28H44O C28H44O C28H44O C37H67NO13 C9H6O4 C18H24O2 C18H24O2 C2H6O2 C16H19N3O5S

396.65 396.65 396.65 733.93 178.14 272.38 272.38 62.07 365.40

V-7, V-8 E-11, E-12 E-11, E-12, S-34 E-13 A-21 E-14, E-15 E-14, E-15 E-17 C-151

C9H11NO2 C9H10O3 C22H36O2 C17H20N2O C24H36O2 C22H34O2 C18H36O2 C16H32O2 C20H40O2 C20H38O2 C18H36O2 C20H40O2 C15H19N5O4S

165.19 166.17 332.52 268.35 356.54 330.50 284.48 256.42 312.53 310.51 284.48 312.53 365.41

B-11, B-12 H-76 A-66 E-16 D-90, D-91 E-6 E-24, E-25 E-21 E-26 E-22, E-23 E-24, E-25 E-26 C-105

C8H18O C16H14O2 C15H13O4N5

130.23 238.28 327.30

E-18, E-20 H-81 C-153

C9H17N5O

211.26

A-75

(continued)

CAT4240—PRELIMS —2/11/2006—SRIDHAR—XML MODEL C – pp. 1–48

Solute 2-Ethylamino-4-isopropylamino6-methylthio-1,3,5-triazine a-Ethylcaproic acid Ethylene glycol a,a 0 -Ethylenedinitrilodi-o-cresol 2,2 0 -(Ethylenedioxy)diethanol 2-Ethylhexanoic Acid Di-(2-ethylhexyl)phosphoric acid N-Ethyl-N-(2-hydroxyethyl)4-[(p-nitrophenyl)azo]aniline Eucalyptus leaves extract Eugenol Ewe’s milk fat Fat Brown RR Fe(acac)3 Fe(thd)3 Fe(tod)3 Fenchone Ferrocene Ferulic acid Fish liver oil (Cod) Fish liver oil (Deep Sea Shark) Fish liver oil (Orange Roughy Fish) Fish liver oil (Spiny Dogﬁsh) Fish oil (Sand Eel) Fish oil ethyl esters (EE-1) Fish oil ethyl esters (EE-2) Fish oil ethyl esters (EE-3) Fish oil ethyl esters (EE-4) Fish oil ethyl esters (EE-5) Fish oil ethyl esters (EE-6) Fish oil ethyl esters (EE-7) Fish oil ethyl esters (EE-8) Fish oil ethyl esters (EE-9) Fish oil ethyl esters (EE-10) Fish oil ethyl esters (EE-11) Fish oil ethyl esters (EE-12) Fish oil ethyl esters (EE-13) Fish oil fatty acid ethyl ester Fish oil fatty acid ethyl ester, Omega 3 Concentrate Fish oil fatty acid ethyl ester, Original FAEE Fish oil fatty acid ethyl ester, Urea Fractionated Flavon-3-ol Flavone Florfenicol Fluoranthene 9-Fluorenone

Formula

MW

Data Table No.

C9H17N5S

227.33

A-23, A-24

C8H16O2 C2H6O2 C16H16N2O2 C6H14O4 C8H16O2 C16H35O4P C16H18N4O3

144.21 62.07 268.31 150.17 144.21 322.42 314.35

E-19 E-17 S-1 T-63, T-64 E-19, E-20 D-41 C-123–C-125

N/A C10H12O2 N/A C16H14N4 C15H21FeO6 C33H57FeO6 C33H57FeO6 C10H16O C10H10Fe C10H10O4 N/A N/A N/A N/A N/A N/A N/A N/A N/A N/A N/A N/A N/A N/A N/A N/A N/A N/A N/A N/A

N/A 164.20 N/A 262.31 353.17 605.65 605.65 152.23 186.03 194.18 N/A N/A N/A N/A N/A N/A N/A N/A N/A N/A N/A N/A N/A N/A N/A N/A N/A N/A N/A N/A

E-27 E-28 E-30 C-162 I-4, I-5 I-6 I-7 F-1 F-2–F-5 F-6–F-8 F-9, F-10 F-13 F-11 F-12, F-13 F-14 F-15 F-16 F-17 F-18 F-19 F-20 F-21 F-22 F-23 F-24 F-25 F-26 F-27 F-28 F-28

N/A

N/A

F-28

N/A

N/A

F-28, F-29

C15H10O3 C15H10O2 C12H14Cl2FNO4S C16H10 C13H8O

238.24 222.24 358.21 202.25 180.20

H-82 F-30, F-31 F-32 A-3, F-33–F-35 F-41 (continued)

CAT4240—PRELIMS —2/11/2006—SRIDHAR—XML MODEL C – pp. 1–48

Solute Fluoren-2-amine Fluoren-9-one Fluorene 9a-Fluoro-16b-methylprednisolone 5-Fluoro-2,4-pyrimidinedione 5-Fluorouracil 2-Fluoro-a-methyl-4-biphenylacetic acid Flurbiprofen 1-Formyl-2-naphthol Frangulin A D-Fructose D-(K)-Fructose Fungal oil b-D-Galactopyranose pentaacetate b-D-Galactose pentaacetate Gallic acid 3,5-dimethyl ether Gallic acid dodecyl ester Gallic acid methyl ester Gallic acid propyl ester Gallium tris(acetylacetonate) Gentisic acid Ginger rhizomes extract D-Glucopyranose pentaacetate D-Glucose D-(C)-Glucose D-Glucose pentaacetate Glycerin Glycerin monolaurate Glycerin monooleate Glycerin tributyrate Glycerin tridecanoate Glycerin tridodexanoate Glycerin trihexanoate Glycerin trilinoleate Glycerin trimyristate Glycerin trioctanoate Glycerin trioleate Glycerin tripalmitate Glycerin tristearate Glycerol Glycerol dilaurate Glycerol dioeate Glycerol monododecanoate Glycerol monooleate Glycerol tributanoate Glycerol tricaprate Glycerol tricaproate Glycerol tricaprylate Glycerol trihexadecanoate Glycerol trilaurate

Formula

MW

C13H11N C13H8O C13H10 C22H29FO5 C4H3FN2O2 C4H3FN2O2 C15H13FO2 C15H13FO2 C11H8O2 C21H20O9 C6H12O6 C6H12O6 N/A C16H22O11 C16H22O11 C9H10O5 C19H30O5 C8H8O5 C10H12O5 C15H21GaO6 C7H6O4 N/A C16H22O11 C6H12O6 C6H12O6 C16H22O11 C3H8O3 C15H30O4 C21H40O4 C15H26O6 C33H62O6 C39H74O6 C21H38O6 C57H98O6 C45H86O6 C27H50O6 C57H104O6 C51H98O6 C57H110O6 C3H8O3 C27H52O5 C39H72O5 C15H30O4 C21H40O4 C15H26O6 C33H62O6 C21H38O6 C27H50O6 C51H98O6 C39H74O6

181.23 180.20 166.22 392.46 130.08 130.08 244.26 244.26 172.18 416.38 180.16 180.16 N/A 390.34 390.34 198.17 338.44 184.15 212.20 367.05 154.12 N/A 390.34 180.16 180.16 390.34 92.09 274.40 356.55 302.36 554.84 639.00 386.52 879.38 723.16 470.68 885.43 807.32 891.48 92.09 456.70 620.99 274.40 356.55 302.36 554.84 386.52 470.68 807.32 639.00

Data Table No. A-31 F-41 F-27, F-36–F-40 B-32 F-42 F-42 F-43 F-43 H-89 F-44 F-45 F-45 F-46 P-21 P-21 S-46 D-94 M-39 P-124 G-1 G-2 G-3 P-22 G-4, G-5 G-4, G-5 P-22 G-6, G-7 M-62 M-63, M-64 T-53, T-54 T-55 T-69, T-70 T-56 T-74 T-75 T-57 T-82–T-86 T-87–T-90 T-102 G-6, G-7 D-58 D-85 M-62 M-63, M-64 T-53, T-54 T-55 T-56 T-57 T-87–T-90 T-69, T-70 (continued)

CAT4240—PRELIMS —2/11/2006—SRIDHAR—XML MODEL C – pp. 1–48

Solute Glycerol trilinoleate Glycerol trioctadecanoate Glycerol trioleate Glycerol tritetradecanoate Glycine Grape seed oil Griseofulvin Heneicosane 2,2 0 ,3,4,4 0 ,5,5 0 -Heptachlorobiphenyl Heptacosane Heptadecane Heptadecyl methyl ketone Hexabromocyclododecane Hexacarbonylmolybdenum 1,2,3,4,10,10-Hexachloro-6,7-epoxy1,4,4a,5,6,7,8,8a-octahydro-endo1,4-endo-5,8-dimethanonaphthalene Hexachlorobenzene 2,2 0 ,3,3 0 ,4,4 0 -Hexachlorobiphenyl 2,2 0 ,4,4 0 ,5,5 0 -Hexachlorobiphenyl g-1,2,3,4,5,6-Hexachlorocyclohexane Hexachloroethane Hexacosane 6,7,9,10,12,13,15,16,23,24,26,27, 29,30,32,33-Hexadecahydro dibenzo[b,q][1,4,7,10,13,16,19, 22,25,28]decaoxacyclotriacontin Hexadecane Hexadecanoic acid 1-Hexadecanol Hexadecyl docosanoate N-Hexadecyl-7-nitro-4-benzofurazanamine 4-(Hexadecylamino)-7-nitrobenz-2-oxa1,3-diazole (all E)-2,6,10,15,19,23-Hexamethyl2,6,10,14,18,22-tetracosahexaene Hexamethylbenzene 2,6,10,15,19,23-Hexamethyltetracosane Hexanoic Acid 1-Hexanoic Acid 1-Hexanol 3-Hexanol Hexatriacontane n-Hexyl alcohol Hydrocortisone Hydroquinone Hydroquinone dimethyl ether 4 0 -Hydroxyacetanilide 4-Hydroxy-1,2-dimethylbenzene (G)-2-Hydroxy-1,2-diphenylethanone

Formula

MW

Data Table No.

C57H98O6 C57H110O6 C57H104O6 C45H86O6 C2H5NO2 N/A C17H17ClO6 C21H44 C12H3Cl7 C27H56 C17H36 C19H38O C12H18Br6 C6MoO6 C12H8Cl6O

879.38 891.48 885.43 723.16 75.07 N/A 352.77 296.58 395.32 380.73 240.47 282.50 641.73 264.00 380.91

T-74 T-102 T-82–T-86 T-75 G-8 G-9 G-10 H-1 H-2–H-4 H-5 H-6 N-88 H-7 M-58 E-9

C6Cl6 C12H4Cl6 C12H4Cl6 C6H6Cl6 C2Cl6 C26H54 C28H40O10

284.78 360.88 360.88 290.83 236.74 366.71 536.61

H-8–H-10 H-11, H-12 H-13–H-15 L-23 H-16 H-17, H-18 D-16

C16H34 C16H32O2 C16H34O C38H76O2 C22H36N4O3 C22H36N4O3

226.44 256.42 242.44 565.01 404.55 404.55

H-19–H-21 P-6–P-13 C-47–C-51 P-14 H-22 H-22

C30H50

410.72

S-13, S-14

C12H18 C30H62 C6H12O2 C6H12O2 C6H14O C6H14O C36H74 C6H14O C21H30O5 C6H6O2 C8H10O2 C8H9NO2 C8H10O C14H12O2

162.27 422.81 116.16 116.16 102.17 102.17 506.97 102.17 362.46 110.11 138.16 151.16 122.16 212.24

B-26, H-23–H-25 S-7–S-12 H-26, H-27 H-26, H-27 H-28 H-29 H-30–H-32 H-28 H-33 D-50, H-34–H-39 D-60 A-4–A-6 X-3 B-27 (continued)

CAT4240—PRELIMS —2/11/2006—SRIDHAR—XML MODEL C – pp. 1–48

Solute 4-hydroxy-1,3-dimethylanthracen10(9H)-one 18b-Hydroxy-11,17a-dimethoxy-3b,20ayohimban-16b-carboxylic acid methyl ester 3,4,5-trimethoxybenzoate 1-Hydroxy-2-(1-butoxymethyl)anthraquinone 1-Hydroxy-2-(1-propoxymethyl)anthraquinone 1-Hydroxy-2-(ethoxymethyl)anthraquinone 1-Hydroxy-2-(isobutoxymethyl)anthraquinone 1-Hydroxy-2-(methoxymethyl)anthraquinone 1-Hydroxy-2,4-dimethylanthrone 1-Hydroxy-2-ethylanthrone 1-Hydroxy-2-methylanthracen9(10H)-one 1-Hydroxy-2-methylanthraquinone 1-Hydroxy-2-methylanthrone 4-Hydroxy-2-methyl-N-2-pyridinyl2HK1,2-benzothiazine-3-carboxamide 1,1-dioxide 2-Hydroxy-1-naphthaldehyde 2-Hydroxy-2-phenylacetic acid (G)-2-Hydroxy-2-phenylacetophenone 3-Hydroxy-2-phenylchromone 2-(3-Hydroxy-2-quinolyl)1,3-indanedione 4-Hydroxy-3,5-dimethoxybenzoic acid 4-Hydroxy-3-methoxybenzaldehyde 4-Hydroxy-3-methoxybenzoic acid 4-Hydroxy-3-methoxycinnamic acid 3-(4-Hydroxy-3-methoxyphenyl)acrylic acid 1-Hydroxy-3-methyl-9H-xanthen-9-one 1-Hydroxy-3-methylthioxanthen-9-one 1-Hydroxy-3-methylthioxanthone 1-Hydroxy-3-methylxanthone 1-Hydroxy-4-(prop-2-enyloxy)anthraquinone 7-Hydroxy-4-methyl-2H-chromen-2-one 7-Hydroxy-4-methylcoumarin 1-Hydroxy-8-(prop-2-enyloxy)anthraquinone 1-Hydroxy-9H-thioxanthen-9-one 1-Hydroxy-9H-xanthen-9-one 17b-Hydroxyandrost-4-en-3-one 2-Hydroxyanisole

Formula

MW

Data Table No.

C16H14O2

238.28

H-80

C33H40N2O9

608.68

R-2

C19H18O4

310.34

H-41

C18H16O4

293.23

H-47

C17H14O4

282.29

H-42

C19H18O4

310.34

H-43

C16H12O4

268.26

H-44

C16H14O2 C16H14O2 C15H12O2

238.28 238.28 224.25

H-80 H-81 H-85

C15H10O3 C15H12O2 C15H13N3O4S

238.25 224.25 331.35

H-84 H-85 P-89

C11H8O2 C8H8O3 C14H12O2 C15H10O3 C18H11NO3

172.18 152.15 212.24 238.24 289.28

H-89 M-1 B-27 H-82 C-149

C9H10O5 C8H8O3 C8H8O4 C10H10O4 C10H10O4

198.17 152.15 168.15 194.18 194.18

S-46 V-3 V-1, V-2 F-6–F-8 F-6–F-8

C14H10O3 C14H10O2S C14H10O2S C14H10O3 C17H12O4

226.23 242.29 242.29 226.23 280.27

H-88 H-87 H-87 H-88 H-45

C10H8O3 C10H8O3 C17H12O4

176.17 176.17 280.27

H-86 H-86 H-46

C13H8O2S C13H8O3 C19H28O2 C7H8O2

228.27 212.20 288.42 124.14

H-92 H-93 T-7, T-8 M-26 (continued)

CAT4240—PRELIMS —2/11/2006—SRIDHAR—XML MODEL C – pp. 1–48

Solute

Formula

MW

Data Table No.

1-Hydroxyanthraquinone p-Hydroxyazobenzene a-Hydroxybenzeneacetic acid 2-Hydroxybenzoic acid 3-Hydroxybenzoic acid 4-Hydroxybenzoic acid o-Hydroxybenzoic acid m-Hydroxybenzoic acid

C14H8O3 C12H10N2O C8H8O3 C7H6O3 C7H6O3 C7H6O3 C7H6O3 C7H6O3

224.21 198.22 152.15 138.12 138.12 138.12 138.12 138.12

p-Hydroxybenzoic acid

C7H6O3

138.12

4-Hydroxybenzoic acid ethyl ester 2-Hydroxybenzoic acid methyl ester 4-Hydroxybenzoic acid propyl ester (G)-2-Hydroxycaproic acid 4-Hydroxychromen-2-one 7-Hydroxychromen-2-one 2-Hydroxycinnamic acid 3-Hydroxycinnamic acid 4-Hydroxycinnamic acid 4-Hydroxycoumarin 7-Hydroxycoumarin 3-Hydroxyﬂavone 2-Hydroxyhexanoic acid N-(4-Hydroxyphenyl)acetamide 2-Hydroxypropanoic acid 4-Hydroxypyrimidine 8-Hydroxyquinoline 5-Hydroxysalicylic acid 1-Hydroxythioxanthone 1-Hydroxyxanthone Imipramine hydrochloride Indium tris(acetylacetonate) 1H-Indole Indole Iodoform Ionic liquid [bmim][BF4] Ionic liquid [bmim][PF6] Iron bis(cyclopentadienide) Iron tris(acetylacetonate) Iron tris(2,2,6,6-tetramethyl-3,5heptanedionate) Iron tris(2,2,7-trimethyl-3,5-octanedionate) 1,3-Isobenzofurandione (4S)-4-Isopropenyl-1-methyl1-cyclohexene 4-Isopropenyl-1-methyl-1-cyclohexene 5-Isopropyl-2-methylphenol 1-(Isopropylamino)-3-(1-naphthyloxy)2-propanol

C9H10O3 C8H8O3 C10H12O3 C6H12O3 C9H6O3 C9H6O3 C9H8O3 C9H8O3 C9H8O3 C9H6O3 C9H6O3 C15H10O3 C6H12O3 C8H9NO2 C4H6O3 C4H4N2O C9H7NO C7H6O4 C13H8O2S C13H8O3 C19H24N2HCl C15H21InO6 C8H7N C8H7N CHI3 C8H15N2$BF4 C8H15N2$F6P C10H10Fe C15H21FeO6 C33H57FeO6

166.17 152.15 180.20 132.16 162.14 162.14 164.16 164.16 164.16 162.14 162.14 238.24 132.16 151.16 90.08 96.09 145.16 154.12 228.27 212.20 316.87 412.15 117.15 117.15 393.73 226.02 284.18 186.03 353.17 605.65

H-40 H-48, H-49 M-1 H-50–H-62 H-68–H-72 H-73–H-75 H-50–H-66 H-63, H-64, H-66–H-72 H-65–H-67, H-73–H-75 H-76 M-52 P-125 H-83 H-77 H-78, C-79 C-192, C-193 C-194, C-195 C-196–C-199 H-77 H-78, H-79 H-82 H-83 A-4–A-6 L-1 H-90 H-91 G-2 H-92 H-93 I-1 I-2 I-3 I-3 T-68 B-79 B-77, B-78 F-2–F-5 I-4, I-5 I-6

C33H57FeO6 C8H4O3 C10H16

605.65 148.12 136.23

I-7 P-83 L-17

C10H16 C10H14O C16H21NO2

136.23 150.22 259.35

L-10–L-16, L-18 C-41 P-122

(continued)

CAT4240—PRELIMS —2/11/2006—SRIDHAR—XML MODEL C – pp. 1–48

Solute 4,4 0 -Isopropylidenebis[2,6-dibromophenol] 5-Isopropyl-o-cresol Jojoba bean oil Jojoba wax Ketoprofen Krytox dithiol Krytox picolyl amine Lactic acid Lariat ether carboxylic acid, non-ﬂuorinated Lariat ether carboxylic acid, ﬂuorinecontaining Lariat ether carboxylic acid, ringﬂuorinated Lasalocid sodium salt Lauric acid Lead bis(diisopropyldithiocarbamate) Lecithin S20 L-Leucine D-(K)-Levulose Li(acac) Lidocaine Limonene L-Limonene Linalool Lindane Linoleic Acid Linuron Lipids Lithium acetylacetonate L-Phenylalanine Mandelic acid Manganese tris(acetylacetonate) Manganese bis(acetylacetonate) dihydrate Medroxyprogesterone acetate Megestrol acetate Menadione p-Mentha-1,8-diene (S)-(K)-p-Mentha-1,8-diene (R)-(K)-p-Mentha-6,8-dien-2-one Menthol 2-Mercaptopyrimidine Mercury bis(dibutyldithiocarbamate) Mercury bis(diethyldithiocarbamate) Mercury bis(dihexyldithiocarbamate) Mercury bis(dipentyldithiocarbamate) Mercury bis(dipropyldithiocarbamate) Mercury bis[bis(triﬂuoroethyl)dithiocarbamate]

Formula

MW

Data Table No.

C15H12Br4O2

543.87

T-10

C10H14O N/A N/A C16H14O3 N/A N/A C4H6O3 C21H24O8 C29H26F6O8

150.22 N/A N/A 254.28 N/A N/A 90.08 404.42 616.51

C-41 J-1 J-1 K-1–K-3 K-4 K-5 L-1 L-2 L-2

C21H22F2O8

440.40

L-2

C34H53NaO8 C12H24O2 C14H28N2PbS4 N/A C6H13NO2 C6H12O6 C5H7LiO2 C14H22N2O C10H16 C10H16 C10H18O C6H6Cl6 C18H32O2 C9H10Cl2N2O2 N/A C5H7LiO2 C9H11NO2 C8H8O3 C15H21MnO6 C10H14MnO4$2H2O

612.78 200.32 559.83 N/A 131.17 180.16 106.05 234.34 136.23 136.23 154.25 290.83 280.45 249.09 N/A 106.05 165.19 152.15 352.27 289.19

L-3 L-4, L-5 L-6 L-7 L-8 F-45 L-27 L-9 L-10–L-20 L-17 L-20–L-22 L-23 L-24, L-25 P-43 L-26 L-27 P-80 M-1 M-3 M-2

C24H34O4 C24H32O4 C11H8O2 C10H16 C10H16 C10H14O C10H20O C4H4N2S C18H36HgN2S4 C10H20HgN2S4 C26H52HgN2S4 C22H44HgN2S4 C14H28HgN2S4 C10H8F12HgN2S4

386.52 384.51 172.18 136.23 136.23 150.22 156.27 112.15 609.33 497.11 721.54 665.43 553.22 713.00

M-4, M-5 M-6 V-12, V-13 L-10–L-16 L-17 C-42 M-7–M-9 M-10 M-11 M-11, M-13 M-11 M-11 M-11 M-11, M-13, M-15

(continued)

CAT4240—PRELIMS —2/11/2006—SRIDHAR—XML MODEL C – pp. 1–48

Solute Mercury pyrrolidinedithiocarbamate Methimazole 5-Methoxy-1H-indole 5-Methoxy-1-tetralone 6-Methoxy-1-tetralone 7-Methoxy-1-tetralone 7-Methoxy-2H-1-benzopyran-2-one (S)-2-(6-Methoxy-2-naphthyl)propionic acid 2-Methoxy-4-(2-propenyl)phenol 2-Methoxy-4,6-bis(isopropylamino)1,3,5-triazine 2-Methoxyanisole 4-Methoxyanisole 4-Methoxybenzaldehyde 3-Methoxybenzamide 4-Methoxybenzamide Methoxybenzene 2-Methoxybenzoic acid 3-Methoxybenzoic acid 4-Methoxybenzoic acid Methoxychlor 5-Methoxyindole 2-Methoxynapthalene 2-Methoxynitrobenzene 2-Methoxyphenol o-Methoxyphenylacetic acid m-Methoxyphenylacetic acid p-Methoxyphenylacetic acid Methyl 2-[4-(2,4-dichlorophenoxy)phenoxy]propanoate Methyl cyanide Methyl gallate Methyl 2-hydroxybenzoate Methyl 4-hydroxybenzoate Methyl 2-nitrobenzoate Methyl 3-nitrobenzoate Methyl 4-nitrobenzoate Methyl o-nitrobenzoate Methyl m-nitrobenzoate Methyl p-nitrobenzoate Methyl oleate Methyl phenyl ether Methyl salicylate 2-Methyl-1,4-naphthoquinone 3-Methyl-1-phenyl-4-(phenylazo)pyrazol-5-ol 5-Methyl-2-(1-methylethyl)cyclohexanol 5-Methyl-2-(1-methylethyl)phenol

Formula

MW

Data Table No.

C10H16HgN2S4 C4H6N2S C9H9NO C11H12O2 C11H12O2 C11H12O2 C10H8O3 C14H14O3

493.08 114.17 147.17 176.21 176.21 176.21 176.17 230.26

M-11 M-16 M-24 M-28, M-32 M-29, M-31 M-30–M-32 M-23 N-55–N-62

C10H12O2 C10H19N5O

164.20 225.29

E-28 P-115

C8H10O2 C8H10O2 C8H8O2 C8H9O2N C8H9O2N C7H8O C8H8O3 C8H8O3 C8H8O3 C16H15Cl3O2 C9H9NO C11H10O C7H7NO3 C7H8O2 C9H10O3 C9H10O3 C9H10O3 C16H14Cl2O4

138.16 138.16 136.15 151.16 151.16 108.14 152.15 152.15 152.15 345.65 147.17 158.20 153.14 124.14 166.17 166.17 166.17 341.19

D-59 D-60 A-35 M-17 M-18 A-38, A-39 M-19 M-20 A-37, M-21 M-22, P-43 M-24 M-25 N-76 M-26 M-27 M-27 M-27 P-43

C2H3N C8H8O5 C8H8O3 C8H8O3 C8H7NO4 C8H7NO4 C8H7NO4 C8H7NO4 C8H7NO4 C8H7NO4 C21H36O2 C7H8O C8H8O3 C11H8O2 C16H14N4O

41.05 184.15 152.15 152.15 181.15 181.15 181.15 181.15 181.15 181.15 296.49 108.14 152.15 172.18 278.31

A-10 M-39 M-52 M-53 M-43 M-44 M-45 M-43, M-46, M-47 M-44, M-46 M-45, M-47 M-48–M-50 A-38 M-52 V-12, V-13 C-147

C10H20O

156.27

M-7–M-9

C10H14O

150.22

T-42 (continued)

CAT4240—PRELIMS —2/11/2006—SRIDHAR—XML MODEL C – pp. 1–48

Solute 6-Methyl-2HK1-benzopyran-2-one 7-Methyl-2H-1-benzopyran-2-one Methyl-2-naphthyl ether N-(4-Methyl-2-pyrimidyl)sulfanilamide 1-Methyl-3-nitrobenzene 3-Methyl-3-pentanol 2-Methyl-4-[[4-(phenylazo)phenyl]azo]phenol 1-Methyl-4-imidazoline-2-thione 2-Methyl-5-nitro-1H-imidazole1-ethanol benzoate 4-methyl-6-(5-chloro-2-pyridinyl)-6,7dihydro-7-oxo-5H-pyrrolo[3,4-b]pyrazin-5-yl ester 1-(Methylamino)anthraquinone 2-Methylanthracene 2-Methylbenzoic acid 3-Methylbenzoic acid 4-Methylbenzoic acid 24-Methylcholesta-5,7,22-trien-3b-ol 6-Methylcoumarin 7-Methylcoumarin 2,2 0 -Methylenebiphenyl 1,1 0 ,1 00 -Methylidynetrisbenzene 1-Methylimidazole-2-thiol 3-Methylindole 4-Methyl-L-norvaline Methylmorphine 1-Methylnaphthalene 2-Methylnaphthalene (E)-8-Methyl-N-vanillyl-6-nonenamide 7-Methoxycoumarin Methylparaben 4-Methylphenol (4S)-4-Methylsalinomycin sadium salt Methylumbelliferone 4-Methylumbelliferone Metronidazole benzoate Miconazole Milk fat triglyceride Milk thistle seed oil Mn(acac).22H2O Mn(acac)3 Molybdenum hexacarbonyl Monensin sodium salt Monocrotaline Monolaurin Monoolein Myristic acid

Formula

MW

Data Table No.

C10H8O2 C10H8O2 C11H10O C11H12N4O2S C7H7NO2 C6H14O C19H16N4O

160.17 160.17 158.20 264.30 137.14 102.17 316.36

M-37 M-38 M-25 S-41 N-82 M-51 C-145, C-146

C4H6N2S C13H13N3O4

114.17 275.26

M-16 M-54

C17H17ClN6O3

388.81

Z-3

C15H11NO2 C15H12 C8H8O2 C8H8O2 C8H8O2 C28H44O C10H8O2 C10H8O2 C13H10 C19H16 C4H6N2S C9H9N C6H13NO2 C18H21NO3 C11H10

237.25 192.26 136.16 136.16 136.16 396.65 160.17 160.17 166.22 244.33 114.17 131.17 131.17 299.36 142.20

C11H10 C18H27NO3 C10H8O3 C8H8O3 C7H8O C43H71NaO11 C10H8O3 C10H8O3 C13H13N3O4 C18H14Cl4N2O N/A N/A C10H14MnO4$2H2O C15H21MnO6 C6MoO6 C36H61NaO11 C16H23NO6 C15H30O4 C21H40O4 C14H28O2

142.20 305.41 176.17 152.15 108.14 787.02 176.17 176.17 275.26 416.12 N/A N/A 289.19 352.27 264.00 692.86 325.36 274.40 356.55 228.37

C-126 M-33, N-78 M-34 M-35 M-36 E-11, E-12 M-37 M-38 F-27, F-36–F-39 T-94, T-95 M-16 S-5 L-8 C-171 A-39, B-10, M-40, M-42 N-30, M-40–M-42 C-16–C-18 M-23 M-53 C-202 N-63 M-23 H-86 M-54 M-55 M-56 M-57 M-2 M-3 M-58 M-59 M-60, M-61 M-62 M-63, M-64 M-65–M-67 (continued)

CAT4240—PRELIMS —2/11/2006—SRIDHAR—XML MODEL C – pp. 1–48

Solute Myristic acid ethyl ester Naphthalene 1,4-Naphthalenedione 2-Naphthalenenitrile 1-Naphthalenol 2-Naphthalenol 4-(1-Naphthalenylazo)-1,3-benzenediamine 1-Naphthol 2-Naphthol a-Naphthol b-Naphthol 2-Naphthonitrile 1,4-Naphthoquinone p-Naphthoquinone Naproxen (C)-Naproxen (C)-(S)-Naproxen Narasin sodium salt NBD Nickel bis[bis(triﬂuoroethyl)dithiocarbamate] Nickel bis(diethyldithiocarbamate) Nickel bis(hexaﬂuoroacetylacetonate) Nickel Complex Nicotinic acid Nifedipine Nimesulide Nimodipine Nitrendipine 2-Nitroanisole 9-Nitroanthracene 2-Nitrobenzoic acid methyl ester 3-Nitrobenzoic acid methyl ester 4-Nitrobenzoic acid methyl ester 4-Nitro-2-chloro-4 0 -[ethyl(2-hydroxyethyl)amino]azobenzene 3-Nitro-6-[4-[N,N-di(acetoxyethyl)amino]phenyl]azobenzonitrile 2-Nitrodiphenylamine 2-Nitro-N-phenylaniline 3-Nitrophenol 4-Nitrophenol m-Nitrophenol p-Nitrophenol 4-Nitro-2-phenoxymethanesulfonanilide 4-(2-Nitrophenyl)-2,6-dimethyl-3,5dicarbomethoxy-1,4- dihydropyridine 4-(4-Nitrophenylazo)aniline 1-(4-Nitrophenylazo)-2-naphthol

Formula

MW

Data Table No.

C16H32O2 C10H8 C10H6O2 C11H7N C10H8O C10H8O C16H14N4

256.42 128.17 158.15 153.18 144.17 144.17 262.31

E-21 N-1–N-35, P-71 N-52–N-54 C-204 N-36, N-37 N-39–N-48 C-162

C10H8O C10H8O C10H8O C10H8O C11H7N C10H6O2 C10H6O2 C14H14O3 C14H14O3 C14H14O3 C43H71NaO11 C22H36N4O3 C10H8F12N2NiS4

144.17 144.17 144.17 144.17 153.18 158.15 158.15 230.26 230.26 230.26 787.02 404.55 N/A

N-36, N-37 N-39–N-48 N-36–N-38 N-38–N-51 C-204 N-52–N-54 N-52–N-54 N-55–N-62 N-55–N-62 N-55–N-62 N-63 H-22 M-12, M-13, M-15

C10H20N2NiS4 C10H2F12NiO4 C22H22N4Ni C6H5NO2 C17H18N2O6 C13H12N2O5S C21H26N2O7 C18H20N2O6 C7H7NO3 C14H9NO2 C8H7NO4 C8H7NO4 C8H7NO4 C16H17ClN4O3

N/A N/A 401.15 123.11 346.33 308.31 418.44 360.36 153.14 223.23 181.15 181.15 181.15 348.79

M-12, M-13 M-13 N-64–N-66 N-67–N-71 N-72 N-73 N-74 N-75 N-76 N-77, N-78 M-43 M-44 M-45 C-128

C21H21N5O6

439.43

C-136

C12H10N2O2 C12H10N2O2 C6H5NO3 C6H5NO3 C6H5NO3 C6H5NO3 C13H12N2O5S C17H18N2O6

214.22 214.22 139.11 139.11 139.11 139.11 308.31 346.33

N-79 N-79 N-80 N-81 N-80 N-81 N-73 N-72

C12H10N4O2 C16H11N3O3

242.24 293.28

C-114, C-115 P-18 (continued)

CAT4240—PRELIMS —2/11/2006—SRIDHAR—XML MODEL C – pp. 1–48

Solute 2-Nitroso-1-naphthol 3-Nitrotoluene Nonacosane Nonadecane Nonadecanenitrile 2-Nonadecanone 1-Nonanol Nonyl alcohol 4-(N-Phenylamino)-4 0 -nitroazobenzene Octacosane (Z,Z)-9,12-Octadecadienoic acid Octadecane 1-Octadecanethiol Octadecanoic acid 1-Octadecanol (Z)-9-Octadecenoic acid (Z)-9-Octadecenoic acid ethyl ester (Z)-9-Octadecenoic acid methyl ester n-Octadecyl alcohol Octadecyl cyanide Octadecylmercaptan (3R,5aS,6R,8aS,9R,12S,12aR)Octahydro-3,6,9-trimethyl-3,12epoxy-12H-pyrano[4,3-j]-1,2benzodioxepin-10(3H)-one Octane n-Octane Octyl 2,5-dichlorobenzoate Octyl ether Octyl pentaethylene glycol ether Octyl(phenyl)(N,N-diisobutyl carbamoyl)methylphosphine oxide Octylpentaglycol Okadaic acid Oleic acid Oleic acid ethyl ester Oleic acid methyl ester Olive oil Orange peel oil Oxacyclododecan-2-one Oxacyclohexadecan-2-one 17b-(1-oxopropoxy)-androst-4-en-3-one Paclitaxel Palladium bis(acetylacetonate) Palladium bis(dibutyldithiocarbamate) Palladium bis(diethyldithiocarbamate) Palladium bis(diisobutyldithiocarbamate) Palladium bis(diisopropyldithiocarbamate)

Formula

MW

Data Table No.

C10H7NO2 C7H7NO2 C29H60 C19H40 C19H37N C19H38O C9H20O C9H20O N/A C28H58 C25H32O2 C18H38 C18H38S C18H36O2 C18H38O C18H34O2 C20H38O2 C21H36O2 C18H38O C19H37N C18H38S C15H22O5

173.17 137.14 408.79 268.53 279.50 282.50 144.25 144.25 N/A 394.76 280.45 254.49 268.56 284.48 270.49 282.46 310.51 296.49 270.49 279.50 268.56 282.33

C-155 N-82 N-83, N-84 N-85, N-86 N-87 N-88 N-89 N-89 C-113 O-1–O-9 L-24, L-25 O-10, O-11 O-16 S-15–S-29 O-12–O-15, S-30–S-32 O-21–O-26 E-22, E-23 M-48–M-50 O-12–O-15, S-30–S-32 N-87 O-16 A-69

C8H18 C8H18 C15H20Cl2O2 C16H34O C18H38O6 C24H42NO2P

114.23 114.23 303.23 242.44 350.49 407.57

O-17 B-70, O-17 O-18 D-83 P-36 O-19

C18H38O6 C44H68O13 C18H34O2 C20H38O2 C21H36O2 N/A N/A C11H20O2 C15H28O2 C22H32O3 C47H51NO14 C10H14O4Pd C18H36N2PdS4

350.49 805.00 282.46 310.51 296.49 N/A N/A 184.28 240.38 344.49 853.91 304.64 N/A

P-36 O-20 O-21–O-27 E-22, E-23 M-48–M-50 O-27 O-28 U-2 P-35 T-9 T-1, T-2 P-1 M-14

C10H20N2PdS4 C18H36N2PdS4 C14H28N2PdS4

N/A N/A 459.07

M-14 M-14 M-14, P-4

(continued)

CAT4240—PRELIMS —2/11/2006—SRIDHAR—XML MODEL C – pp. 1–48

Solute

Formula

MW

Data Table No.

Palladium bis(dioctyldithiocarbamate) Palladium bis(dipentyldithiocarbamate) Palladium bis(methylthioglycolate) Palladium bis(2,2,6,6-tetramethyl3,5-heptanedionate) Palladium diimine $ BArF complex Palm kernel oil Palm oil Palmitic acid Palmitic acid ethyl ester Palmityl alcohol Palmityl behenate Para red PCB 15 PCB 70 PCB 77 PCB 128 PCB 153 PCB 180 PCB 1254 Pd(acac)2 Pd(MTG)2 Pd(thd)2 PEG Penicillin G Penicillin V 1,2,3,4,6-Pentaacetyl-D-galactose 1,2,3,4,6-Pentaacetyl-D-glucose 2,2 0 ,4,5,5 0 -Pentachlorobiphenyl Pentachlorophenol Pentacosane Pentadecaﬂuorooctyl 2,5-dichlorobenzoate 1-Pentadecanol Pentadecanolactone 15-Pentadecanolide Pentaethylene glycol n-octyl ether Pentaﬂuorobutyl 2,5-dichlorobenzoate Pentaﬂuoropropyl 2,5-dichlorobenzoate 3,3 0 ,4 0 ,5,7-Pentahydroxyﬂavone Perchlorobenzene Perchloroethane Perylene a-Perylene Pesticides Phenanthrene

C34H68N2PdS4 C22H44N2PdS4 C6H10O4PdS2 C22H38O4Pd

N/A N/A 316.69 472.94

M-14 M-14 P-2 P-3

N/A N/A N/A C16H32O2 C18H36O2 C16H34O C38H76O2 C16H11N3O3 C12H8Cl2 C12H6Cl4 C12H6Cl4 C12H4Cl6 C12H4Cl6 C12H3Cl7 N/A C10H14O4Pd C6H10O4PdS2 C22H38O4Pd N/A C16H18N2O4S C16H18N2O5S C16H22O11 C16H22O11 C12H5Cl5 C6HCl5O C25H52 C15H5Cl2F15O2 C15H33O C15H28O2 C15H28O2 C18H38O6 C11H7Cl2F5O2 C10H5Cl2F5O2 C15H10O7 C6Cl6 C2Cl6 C20H12 C20H12 N/A C14H10

N/A N/A N/A 256.42 284.48 242.44 565.01 293.28 223.10 291.99 291.99 360.88 360.88 395.32 326.50 304.64 316.69 472.94 N/A 334.39 350.39 390.34 390.34 326.43 266.34 352.68 573.09 229.42 240.38 240.38 350.49 337.07 323.04 302.24 284.80 236.74 252.31 252.31 N/A 178.23

1,10-Phenanthroline Phenazine Phenazopyridine Phenol

C12H8N2 C12H8N2 C11H11N5 C6H6O

180.21 180.21 213.24 94.11

P-5 P-15, P-16 P-17 P-6–P-13 E-24, E-25 C-47–C-51 P-14 P-18 D-25–D-28 T-11 T-12–T-14 H-11, H-12 H-13–H-15 H-2–H-4 A-68 P-1 P-2 P-3 P-102 P-19 P-20 P-21 P-22 P-23–P-25 P-26–P-30 P-31, P-32 P-33 P-34 P-35 P-35 P-36 P-37 P-38 P-39, Q-1 H-8–H-10 H-16 P-40–P-42 P-40–P-42 P-43 A-62, A-63, N-31–N-33, N-50, N-51, P-44–P-71 P-72 P-73 P-74 N-34, P-75, P-76 (continued)

CAT4240—PRELIMS —2/11/2006—SRIDHAR—XML MODEL C – pp. 1–48

Solute Phenol Blue Phenoxymethylpenicillin 3-Phenyl-1-propanol (E)-3-Phenyl-2-propenoic acid 2-Phenyl-4-chromone Phenylacetic Acid transK3-Phenylacrylic acid 3-Phenyl-L-alanine N-Phenylaniline 4-(Phenylazo)phenol 4-[4-(Phenylazo)-1-naphthylazo]phenol N-Phenylbenzenamine Phenylethanoic acid Phenytoin Phosphoric acid tributyl ester Phosphoric acid triphenyl ester 1,3-Phthalandione Phthalic acid diethyl ester Phthalic anhydride Phylloquinone Phytomenadione Picric acid 2-Pinene a-Pinene cis-2-Pinen-4-ol 1-Piperazinecarboxylic acid Piroxicam Platinum(II) acetylacetonate Platinum bis(acetylacetonate) PMMA Poly(1,1-dihydroperﬂuorooctyl acrylate) Poly(ethyl vinyl ether) Poly(ethylene glycol) dimethylether Poly(ethylene glycol) diol Poly(ethylene glycol) monomethylether Poly(ethylene glycol-block-propylene glycol) Poly(ethylene glycol-ran-propylene glycol) Poly(FOEMA-co-PPGMA) Poly(methyl methacrylate) Poly(oxyalkylene) alkylphenyl ether Poly(propylene glycol) diol Poly(propylene glycol) monobutylether Poly(propylene glycol) monomethylether Poly(styrene) Poly(tetraﬂuoroethylene-co-vinyl acetate) Poly(vinyl butyral) Poly(b-hydroxybutyrate) Polyethylene glycol Prednisolone

Formula

MW

Data Table No.

C14H14N2O C16H18N2O5S C9H12O C9H8O2 C15H10O2 C8H8O2 C9H8O2 C9H11NO2 C12H11N C12H10N2O C22H16N4O C12H11N C8H8O2 C15H12N2O2 C12H27O4P C18H15O4P C8H4O3 C12H14O4 C8H4O3 C31H46O2 C31H46O2 C6H3N3O7 C10H16 C10H16 C10H16O C17H17ClN6O3 C15H13N3O4S C10H14O4Pt C10H14O4Pt N/A N/A N/A N/A N/A N/A N/A

226.27 350.39 136.19 148.16 222.24 136.15 148.16 165.19 169.22 198.22 352.39 169.22 136.15 252.27 266.31 326.28 148.12 222.24 148.12 450.70 450.70 229.10 136.23 136.23 152.23 388.81 331.35 393.29 393.29 90000–120000 1 x 106 1500 500 200–600 350–1000 N/A

P-77, P-78 P-20 P-81 C-160 F-30, F-31 P-79 C-160 P-80 D-86–D-88 H-48, H-49 C-118 D-86–D-88 P-79 P-82 T-52 T-96 P-83 D-42 P-83 V-11 V-11 P-84 P-85–P-88 P-85–P-88 V-5 Z-3 P-89 P-90 P-90 P-102 P-91 P-99 P-95 P-96 P-97 P-94

N/A N/A N/A N/A N/A N/A N/A N/A N/A N/A N/A N/A C21H28O5

970–1700 N/A 540,000 N/A 400–2000 1,000 1000, 1200 N/A 140000–166000 N/A 800,000 1000–7500 360.44

P-98 P-100 P-103 P-102 P-104 P-105 P-106 P-102 P-107 P-108 P-101 P-92, P-93 P-109 (continued)

CAT4240—PRELIMS —2/11/2006—SRIDHAR—XML MODEL C – pp. 1–48

Solute Prednisone Pregn-4-ene-3,20-dione Procaine Progesterone Prometone Prometryne 1,2-Propanediol 1,2,3-Propanetriol 1-Propanol 2-Propanol Propazine Propranolol Propyl 2,5-dichlorobenzoate Propyl 4-hydroxybenzoate Propyl gallate Propylene glycol Protocatechualdehyde Protocatechuic acid PS-b-(PMMA-co-PGMA) Pyrazinamine Pyrazine-2-carboxylic acid 2-Pyrazinoic acid Pyrene 3-Pyridinecarboxylic acid 4,4 0 -(2-Pyridylmethylene)bisphenol diacetate 4(1H)-Pyrimidinone Pyrimidine-2-thiol 2,4-pyrimidinedione 2-Pyrimidinethione 4-Pyrimidone Pyrocatechol Quercetin Quinizarin 8-Quinolinol Quinone p-Quinone Rape seed oil RDX Reserpine Resorcinol Resveratrol (E)-Resveratrol Retinol all-trans-Retinol Retinol hexadecanoate all-trans-Retinol palmitate Rh(MTG)3 Rhodium tris(dibutyldithiocarbamate) Rhodium tris(diethyldithiocarbamate)

Formula

MW

Data Table No.

C21H26O5 C21H30O2 C13H20N2O2 C21H30O2 C10H19N5O C10H19N5S C3H8O2 C3H8O3 C3H8O C3H8O C9H16ClN5 C16H21NO2 C10H10Cl2O2 C10H12O3 C10H12O5 C3H8O2 C7H6O3 C7H6O4 N/A C4H5N3 C5H4N2O2 C5H4N2O2 C16H10 C6H5NO2 C22H19NO4

358.43 314.46 236.31 314.46 225.29 241.36 76.09 92.09 60.10 60.10 229.71 259.35 233.09 180.20 212.20 76.09 138.12 154.12 N/A 95.10 124.10 124.10 202.25 123.11 361.39

P-110 P-112 P-111 P-112–P-114 P-115 P-116, P-117 P-118 G-6, G-7 P-119 P-120 P-121 P-112 P-123 P-125 P-124 P-118 P-126 P-127 P-102 A-34 P-128 P-128 P-129–P-137 N-67–N-71 B-39

C4H4N2O C4H4N2S C4H4N2O2 C4H4N2S C4H4N2O C6H6O2 C15H10O7 C14H8O4 C9H7NO C6H4O2 C6H4O2 C16H34 C3H6N6O6 C33H40N2O9 C6H6O2 C14H12O3 C14H12O3 C20H30O C20H30O C36H60O2 C36H60O2 C9H15O6RhS3 C27H54N3RhS6 C15H30N3RhS6

96.09 112.15 112.09 112.15 96.09 110.11 302.24 240.21 145.16 108.09 108.09 226.44 222.12 608.68 110.11 228.24 228.24 286.45 286.45 524.87 524.87 418.31 N/A N/A

H-90 M-10 U-3 M-10 H-90 D-50, P-138, P-139 P-39, Q-1 D-44, D-45 H-91 H-39, Q-2, Q-3 H-39, Q-2, Q-3 R-1 C-215 R-2 D-50, R-3 R-4 R-4 R-5 R-5 V-6 V-6 R-7 M-14 M-14 (continued)

CAT4240—PRELIMS —2/11/2006—SRIDHAR—XML MODEL C – pp. 1–48

Solute Rhodium tris(dihexyldithiocarbamate) Rhodium tris(diisobutyldithiocarbamate) Rhodium tris(diisopropyldithiocarbamate) Rhodium tris(dioctyldithiocarbamate) Rhodium tris(methylthioglycolate) Rhodium tris(2,2,6,6-tetramethyl3,5-heptanedionate) Rosemary oil Saccharose Salen Salicylic acid Salinomycin sodium salt Shale oil Simazine Skatole Sodium 2-(2,6-dichloroanilino)phenyl acetate Sodium bis(triﬂuoroethyl)dithiocarbamate Sodium diethyldithiocarbamate Soybean oil Squalane Squalene Stearic acid Stearic acid ethyl ester 1-Stearyl alcohol Stearyl alcohol Stearyl mercaptan (3b,22E)-Stigmasta-5,22-dien-3-ol Stigmasterol 3,4 0 ,5-Stilbenetriol Sucrose (C)-Sucrose Sudan Blue II Sulfadimethoxine Sulfamerazine Sulfamethazine 2-(Sulfanilylamino)thiazole Sulfathiazole Surfactant Ls-36 Surfactant Ls-45 Surfactant Ls-54 Syringic acid Taxol Tb(thd)3 Tb(tod)3 Tebuconazole Terbium tris(2,2,6,6-tetramethyl3,5-heptanedionate)

Formula

MW

Data Table No.

C39H78N3RhS6 C27H54N3RhS6 C21H42N3RhS6 C51H102N3RhS6 C9H15O6RhS3 C33H57O6Rh

N/A N/A 631.87 N/A 418.31 652.72

M-14 M-14 M-14, R-6 M-14 R-7 R-8

N/A C12H22O11 C16H16N2O2 C7H6O3 C42H69NaO11 N/A C7H12ClN5 C9H9N C14H10Cl2NNaO2$ 4H2O C5H4F6NNaS2

N/A 342.30 268.31 138.12 772.99 N/A 201.66 131.17 390.21

R-9 S-35 S-1 A-74, H-50–H-62 S-2 S-3 S-4 S-5 D-36

N/A

M-12, M-13

C5H10NNaS2 N/A C30H62 C30H50 C18H36O2 C20H41O2 C18H38O C18H38O C18H38S C29H48O C29H48O C14H12O3 C12H22O11 C12H22O11 C22H26N2O2 C12H14N4O4S C11H12N4O2S C12H14N4O2S C9H9N3O2S2 C9H9N3O2S2 C36H74O10 C35H72O10 C34H74O10 C9H10O5 C47H51NO14 C33H57O6Tb C33H57O6Tb C16H22ClN3O C33H57O6Tb

N/A N/A 422.81 410.72 284.48 312.53 270.49 270.49 268.56 412.69 412.69 228.24 342.30 342.30 350.45 310.33 264.30 278.33 255.32 255.32 666.98 652.95 638.92 198.17 853.91 708.74 708.74 307.82 708.74

M-12, M-13 S-6 S-7–S-12 S-13, S-14 S-16–S-29 E-26 O-12–O-15 S-30–S-32 O-16 S-33, S-34 S-33, S-34 R-4 S-35 S-35 C-161 S-39, S-40 S-41 S-42, S-43 S-44, S-45 S-44, S-45 S-36 S-37 S-38 S-46 T-1, T-2 T-4 T-5 T-3 T-4

(continued)

CAT4240—PRELIMS —2/11/2006—SRIDHAR—XML MODEL C – pp. 1–48

Solute Terbium tris(2,2,7-trimethyl3,5-octanedionate) m-Terphenyl Testosterone Testosterone-17-propionate 2,2 0 ,6,6 0 -Tetrabromobisphenol A Tetrabromobisphenol-A 2,4,5,6-Tetrachloro-1,3-benzenedicarbonitrile 2,3 0 ,4 0 ,5-Tetrachlorobiphenyl 3,3 0 ,4,4 0 -Tetrachlorobiphenyl Tetrachloroisophthalonitrile 2,3,4,5-Tetrachlorophenol Tetracosane 6,7,9,10,12,13,15,16,23,24,26, 27,29,30-Tetradecahydrodibenzo [b,n] [1,4,7,10,13,16,19,22,25]nonaoxacycloheptacosin Tetradecanoic acid Tetradecanoic acid ethyl ester Tetraethylene glycol lauryl ether Tetraethylene glycol monododecyl ether 1,2,3,4-Tetrahydro-1-naphthol 1,2,3,4-Tetrahydronaphthalene (K)-(2R,3R)-5,7,3 0 ,4 0 -Tetrahydroxyﬂavan-3-ol (C)-(2R,3S)-5,7,3 0 ,4 0 -Tetrahydroxyﬂavan-3-ol Tetrakis(2,2,6,6-tetramethyl-3,5heptanedionato)cerium Tetrakis(2,2,7-trimethyl-3,5octanedionato)cerium 5,10,15,20-Tetrakis(3,5-bis(triﬂuoromethyl)phenyl)porphyrin 5,10,15,20-Tetrakis(pentaﬂuorophenyl)porphine 5,10,15,20-Tetrakis(pentaﬂuorophenyl)porphyrin Tetralin a-Tetralol (5,7,12,14-Tetramethyl-2,3:9,10-dibenzo[b,i][1,4,8,11]tetra azacyclo tetradecine)nickel (II). Theobromine Theophylline 9-Thiaﬂuorene Thiamphenicol N1-(2-Thiazolyl)sulfanilamide 2-(Thiocyanomethylthio)benzothiazole

Formula

MW

Data Table No.

C33H57O6Tb

708.74

T-5

C18H14 C19H28O2 C22H32O3 C15H12Br4O2 C15H12Br4O2 C8Cl4N2

230.30 288.42 344.49 543.87 543.87 265.91

T-6 C-79, P-114, T-7, T-8 T-9 T-10 T-10 T-15

C12H6Cl4 C12H6Cl4 C8Cl4N2 C6H2Cl4O C24H50 C26H36O9

291.99 291.99 265.91 231.89 338.65 492.56

T-11 T-12–T-14 T-15 T-16 T-17–T-22 D-15

C14H28O2 C16H32O2 C20H42O5 C20H42O5 C10H12O C10H12 C15H14O6

228.37 256.42 362.54 362.54 148.20 132.20 290.27

M-65–M-67 E-21 T-29 T-29 T-27, T-28 T-25, T-26 E-10

C15H14O6

290.27

C-44

C44H76CeO8

873.20

C-45

C44H76CeO8

873.20

C-46

C52H22F24N4

1158.73

T-23

C44H10F20N4

974.55

T-24

C44H10F20N4

974.55

T-24

C10H12 C10H12O C22H22N4Ni

132.20 148.20 401.15

T-25, T-26 T-27, T-28 N-64–N-66

C7H8N4O2 C7H8N4O2 C12H8S C12H15Cl2NO5S C9H9N3O2S2 C9H6N2S3

180.16 180.16 184.26 356.22 255.32 238.36

T-30–T-34 T-35–T-38 D-18 T-39 S-44, S-45 T-40 (continued)

CAT4240—PRELIMS —2/11/2006—SRIDHAR—XML MODEL C – pp. 1–48

Solute 2-(Thiocyanatomethylthio) benzo[d]thiazole Thioxanthen-9-one Thioxanthone 9-Thioxanthone Thymol Titanocene dichloride TNT a-Tocopherol DL-a-Tocopherol d-Tocopherol D-d-Tocopherol p-Tolyl diiodomethyl sulfone 2,3,6-Triacetyl-a-cyclodextrin 2,3,6-Triacetyl-b-cyclodextrin 2,3,6-Triacetyl-g-cyclodextrin Triacontane Tributanoin Tributyl Phosphate Tributyrin Tricaprin Tricaproin Tricaprylin Tricaprylylamine Tricarbonyl(h5-cyclopentadienyl)manganese 1,1,1-Trichloro-2,2-bis(4-chlorophenyl)ethane 1,1,1-Trichloro-2,2-bis(4-methoxyphenyl)ethane 2,4 0 ,5-Trichlorobiphenyl Tricyclo[3.3.1.13,7]decane Tridecaﬂuorooctyl 2,5-dichlorobenzoate Tridecanedioic acid Tridecanoin 1-Tridecanol Tridecyl alcohol Tridodecanoin Triethyl phosphate Triethylene glycol Triglycerides Triglycol Trihexanoin Trihexylamine 3,4,5-Trihydroxybenzoic acid methyl ester 3,4,5-Trihydroxybenzoic acid propyl ester 1,3,8-Trihydroxy-6-methylanthraquinone

Formula C9H6N2S3 C13H8OS C13H8OS C13H8OS C10H14O C10H10Cl2Ti C7H5N3O6 C29H50O2 C29H50O2 C27H46O2 C27H46O2 C8H8I2O2S C72H96O48 C84H112O56 C96H128O64 C30H62 C15H26O6 C12H27O4P C15H26O6 C33H62O6 C21H38O6 C27H50O6 C24H51N C8H5MnO3

MW 238.36

Data Table No. T-40

212.27 212.27 212.27 150.22 249.00 227.13 430.71 430.71 402.65 402.65 422.02 1729.50 2017.75 2306.03 422.81 302.36 266.31 302.36 554.84 386.52 470.68 353.67 204.06

T-41 T-41 T-41 T-42 T-43 T-77, T-78 T-44–T-48 T-44–T-48 T-49, T-50 T-49, T-50 D-56 C-205 C-206 C-207 T-51 T-53, T-54 T-52, U-4 T-53, T-54 T-55 T-56 T-57 T-79 C-212

C14H9Cl5

354.49

B-56, D-1

C16H15Cl3O2

345.65

M-22, P-43

C12H7Cl3 C10H16 C15H7Cl2F13O2 C13H24O4 C33H62O6 C13H28O C13H28O C39H74O6 C6H15O4P C6H14O4 N/A C6H14O4 C21H38O6 C18H39N C8H8O5

257.54 136.23 537.10 244.33 554.84 200.36 200.36 639.00 182.15 150.17 N/A 150.17 386.52 269.51 184.15

T-58–T-60 A-19, A-20 T-61 B-66 T-55 T-62 T-62 T-69, T-70 U-4 T-63, T-64 T-65 T-63, T-64 T-56 T-66 M-39

C10H12O5

212.20

P-124

C15H10O5

270.24

E-8

(continued)

CAT4240—PRELIMS —2/11/2006—SRIDHAR—XML MODEL C – pp. 1–48

Solute

Formula

MW

Data Table No.

11b,17a,21-Trihydroxypregn-4-ene3,20-dione 11b,17,21-Trihydroxy-1,4-pregnadiene3,20-dione 3,4 0 ,5-Trihydroxy-trans-stilbene 1,5,6-Trihydroxyxanthen-9-one 1,5,6-Trihydroxyxanthone Triiodomethane Trilaurin Trilinolein 1,3,7-Trimethyl-2,6-dioxopurine 1,3,3-Trimethyl-2-norbornanone 1,7,7-Trimethylbicyclo[2,2,1]heptan2-one 2,6,6-Trimethylbicyclo[3.1.1]hept-2-ene 1,3,3-Trimethylnorcamphor 1,3,7-Trimethylxanthine Trimyristin

C21H30O5

362.46

H-33

C21H28O5

360.44

P-109

C14H12O3 C13H8O5 C13H8O5 CHI3 C39H74O6 C57H98O6 C8H10N4O2 C10H16O C10H16O

228.24 244.20 244.20 393.73 639.00 879.38 194.19 152.23 152.23

R-4 T-67 T-67 T-68 T-69–T-73 T-74 C-3–C-11 F-1 C-13

C10H16 C10H16O C8H10N4O2 C45H86O6

136.23 152.23 194.19 723.16

1,3,5-Trinitrohexahydro-s-triazine 2,4,6-Trinitrophenol Trinitrotoluene 2,4,6-Trinitrotoluene Tri-n-octylamine Tri-n-octylphosphine Tri-n-octylphosphine oxide Trioctanoin Trioctylamine Trioctylphosphine Trioctylphosphine oxide Triolein Tripalmitin

C3H6N6O6 C6H3N3O7 C7H5N3O6 C7H5N3O6 C24H51N C24H51P C24H51OP C27H50O6 C24H51N C24H51P C24H51OP C57H104O6 C51H98O6

222.12 229.10 227.13 227.13 353.67 370.64 386.63 470.68 353.67 370.64 386.63 885.43 807.32

Triphenylamine Triphenylene Triphenylmethane Triphenylphosphate Triphenylphosphine Triphenylphosphorous Tris(acetylacetonato)yttrium Tris(3-bromopentane-2,4-dionato)chromium Tris(diisopropyldithiocarbamato)rhodium Tris(4-ﬂuorophenyl)phosphine Tris(p-ﬂuorophenyl)phosphine Tris(1,1,1,5,5,5-hexaﬂuoro-2,4pentanedionato)yttrium Tris(methylthioglycolato)rhodium Tris(pentaﬂuorophenyl)phosphine

C18H15N C18H12 C19H16 C18H15O4P C18H15P C18H15P C15H21O6Y C15H18Br3CrO6

245.32 228.29 244.33 326.28 262.29 262.29 386.23 586.01

P-85–P-88 F-1 C-3–C-11 T-71, T-72, T-75, T-76 C-215 P-84 T-77, T-78 T-77, T-78 T-79 T-80 T-81 T-57 T-79 T-80 T-81, U-4 T-82–T-86 T-72, T-73, T-76, T-87–T-90 T-91 A-3, T-92, T-93 T-94, T-95 T-96 T-97, T-98 T-97, T-98 Y-1 C-81

C21H42N3RhS6

631.87

R-6

C18H12F3P C18H12F3P C15H3F18O6Y

316.26 316.26 746.09

T-99 T-99 Y-2

C9H15O6RhS3 C18F15P

418.31 532.14

R-7 T-100 (continued)

CAT4240—PRELIMS —2/11/2006—SRIDHAR—XML MODEL C – pp. 1–48

Solute Tris(pentane-2,4-dionato)chromium Tris(2,4-pentanedionato)cobalt Tris(2,4-pentanedionato)gallium Tris(2,4-pentanedionato)indium Tris(2,4-pentanedionato)iron Tris(2,4-pentanedionato)manganese Tris(2,4-pentanedionato)yttrium Tris(2,2,6,6-tetramethyl-3,5heptanedionato)iron Tris(2,2,6,6-tetramethyl-3,5heptanedionato)rhodium Tris(2,2,6,6-tetramethyl-3,5heptanedionato)terbium Tris(2,2,6,6-tetramethylheptane-3,5dionato)chromium Tris(p-triﬂuoromethylphenyl)phosphine cis-Tris(1,1,1-triﬂuoropentane2,4-dionato)chromium trans-Tris(1,1,1-triﬂuoropentane2,4-dionato)chromium Tris(2,2,7-trimethyl-3,5-octanedionato)iron Tris(2,2,7-trimethyl-3,5octanedionato)terbium Tristearin Tritriacontane Troeger’s base Tropine tropate L-Tryptophan Turmeric oil Ubiquinone Q10 1-Undecanol 11-Undecanolactone Undecanolide Undecyl alcohol Uracil Uranyl bis(thenoyltriﬂuoroacetonate) $ Phosphate Complexes Uranyl bis(triﬂuoroacetylacetonate) $ Pyridine Complex Uranyl dinitrate $ Tributyl phosphate Complex Uranyl thenoyltriﬂuoroacetylacetonate $ Tributyl phosphate complex Vanillic acid Vanillin Vegetable oil from Buriti fruit cis-Verbenol Vitamin A Vitamin A Palmitate

Formula

MW

C15H21CrO6 C15H21CoO6 C15H21GaO6 C15H21InO6 C15H21FeO6 C15H21MnO6 C15H21O6Y C33H57FeO6

349.32 356.26 367.05 412.15 353.17 352.27 386.23 605.65

C-80 C-168 G-1 I-2 I-4, I-5 M-3 Y-1 I-6

C33H57O6Rh

652.72

R-8

C33H57O6Tb

708.74

T-4

C33H57CrO6

601.81

C-82

C21H12F9P C15H12CrF9O6

466.29 511.24

T-101 C-83

C15H12CrF9O6

511.24

C-84

C33H57FeO6 C33H57O6Tb

605.65 708.74

I-7 T-5

C57H110O6 C33H68 C17H18N2 C17H23NO3 C11H12N2O2 N/A C59H90O4 C11H24O C11H20O2 C11H20O2 C11H24O C4H4N2O2 UO2(C8H4F3O2S)2$X UO2(C5H4F3O2)2$ C5H5N UO2(NO3)2$ 2(C12H27O4P) UO2$(C10H6F3O3S)2$ 2(C12H27O4P) C8H8O4 C8H8O3 N/A C10H16O C20H30O C36H60O2

891.48 464.90 250.34 289.37 204.23 N/A 863.34 172.31 184.28 184.28 172.31 112.09 736.40

T-102 T-103 T-104 A-79 T-105 T-106 C-172 U-1 U-2 U-2 U-1 U-3 U-4

655.29

U-5

926.67

U-6, U-7

1329.09

168.15 152.15 N/A 152.23 286.45 524.87

Data Table No.

U-8

V-1, V-2 V-3 V-4 V-5 R-5 V-6 (continued)

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Solute Vitamin C Vitamin D2 Vitamin D3 Vitamin E Vitamin K1 Vitamin K3 Water Wax Wool wax 2,5-Xylenol 2,6-Xylenol 3,4-Xylenol 2,5-Xylidine D-Xylose (C)-Xylose Yttrium tris(acetylacetonate) Yttrium tris(hexaﬂuoroacetylacetonate) Yttrium(III) hexaﬂuoroacetylacetonate Zinc bis(acetylacetonate) Zinc bis(2,4-pentanedionate) Zinc bis(triﬂuoroethyl)dithiocarbamate Zinc dibutyldithiocarbamate Zinc diethyldithiocarbamate Zinc dihexyldithiocarbamate Zinc dipentyldithiocarbamate Zinc dipropyldithiocarbamate Zinc dithiocarbamate complexes Zinc pyrrolidinedithiocarbamate Zopiclone

Formula

MW

C6H8O6 C28H44O C27H44O C29H50O2 C31H46O2 C11H8O2 H2 O N/A N/A C8H10O C8H10O C8H10O C8H11N C5H10O5 C5H10O5 C15H21O6Y C15H3F18O6Y C15H3F18O6Y C10H14O4Zn C10H14O4Zn N/A N/A N/A N/A N/A N/A N/A N/A C17H17ClN6O3

176.12 396.65 384.64 430.71 450.70 172.18 18.02 N/A N/A 122.16 122.16 122.16 121.18 150.13 150.13 386.23 746.09 746.09 263.60 263.60 N/A N/A N/A N/A N/A N/A N/A N/A 388.81

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Data Table No. A-70 V-7, V-8 V-9, V-10 T-44–T-48 V-11 V-12, V-13 W-1–W-4 W-5 W-6 X-1, N-35 X-2 X-3 D-63 X-4 X-4 Y-1 Y-2 Y-2 Z-1 Z-1 Z-2 Z-2 Z-2 Z-2 Z-2 Z-2 Z-2 Z-2 Z-3

Introduction

CONTENTS Supercritical Carbon Dioxide.......................................................................................................... 2 Solubility in Supercritical Carbon Dioxide .................................................................................... 3 Measurement of Solubility in Supercritical Carbon Dioxide ......................................................... 5 Static Methods .......................................................................................................................... 5 Analytical Method............................................................................................................. 5 Synthetic Method .............................................................................................................. 6 Gravimetric Method .......................................................................................................... 7 Dynamic Method ...................................................................................................................... 9 Modeling of Solubility in Supercritical Carbon Dioxide ...............................................................11 Modeling with Equation of States ...........................................................................................11 Simple Density Correlation of Solubility Data .......................................................................13 Guide to Tables and Graphs............................................................................................................15 Arrangement of Tables and Graphs .........................................................................................16 Synonyms .................................................................................................................................16 Carbon Dioxide Density...........................................................................................................16 References........................................................................................................................................16

Fluids become supercritical when they are compressed beyond their critical pressures (Pc) and simultaneously heated beyond their critical temperatures (Tc). Supercritical ﬂuids cannot be liqueﬁed even with extreme compression. However, one may increase pressure to change the density of a ﬂuid continuously from a gas-like state to a liquid-like state. Near the critical region, small changes in pressure can give rise to large changes in density (Figure 1) and Appendix A). In addition to density, diffusivity of the supercritical ﬂuids is much higher than that of liquid solvents, and can be easily varied. For typical conditions, diffusivity in supercritical ﬂuids is of the order of 10K3 cm2/s as compared with 10K1 cm2/s for gases and 10K5 cm2/s for liquids. Typical viscosity of supercritical ﬂuids is of the order of 10K4 g/cm-s, which is about 100-fold lower than that of liquids. The combination of high diffusivity and low viscosity provides rapid equilibration and micropore penetration of the ﬂuid. Various recent books explain the supercritical ﬂuid technology in depth (McHugh and Krukonis 1994; Taylor 1996; McHardy and Sawan 1998; Kiran et al. 2000; Mukhopadhyay 2000; Williams and Clifford 2000; Aria et al. 2002; York et al. 2004; Gupta and Johnston 2006). Supercritical ﬂuid technology has emerged as an important technique for various applications, including production of controlled drug delivery systems, powder processing, pollution prevention and remediation, methods for spray paint and coatings, crystallization processes, bioseparations, food processing, polymerizations, chemical reactions, cleaning of semiconductors and precision machinery, dyeing and dry cleaning of textiles, metal de-binding, and a variety of extractions. 1

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1 0.9

33 C 35 C 40 C 50 C

Density (gm/ml)

0.8 0.7

70 C

0.6 0.5

100 C

0.4 0.3 0.2 0.1 0

0

50

100 150 Pressure (bar)

200

FIGURE 1 Carbon dioxide-density dependence with pressure and temperature. For density data, see Appendix A.

In many industrial applications, supercritical ﬂuids are poised to replace the conventional solvents, mainly due to the quality and purity of the ﬁnal products and environmental beneﬁts. There are various supercritical ﬂuids available, as listed in Table 1.

TABLE 1 Critical Constants and Safety Data for Selected Supercritical Fluids Tc (K)

Pc (bar)

Ethylene Triﬂuoromethane (ﬂuoroform) Chlorotriﬂuoromethane (freon 13) Ethane Carbon dioxide Dinitrogen monoxide (laughing gas)

282.4 299.1 301.8 305.4 304.1 309.6

50.4 48.2 38.8 48.8 73.8 72.4

Sulfur hexaﬂuoride Chlorodiﬂuoromethane (HCFC 142b) Propane Ammonia Dimethyl ether (wood ether) Trichloroﬂuoromethane (freon 11, R 11) Isopropanol Cyclohexane Toluene Water

318.7 410.2 369.8 405.4 400.0 471.2 508.3 553.8 591.8 647.3

37.6 40.5 42.5 113.0 52.4 44.1 47.6 40.7 41.0 221.2

Supercritical Fluid

Safety Hazard Flammable gas

Flammable gas Not combustible but enhances combustion of other substances Combustible under speciﬁc conditions Extremely ﬂammable Flammable and toxic Extremely ﬂammable Highly ﬂammable Highly ﬂammable Highly ﬂammable

SUPERCRITICAL CARBON DIOXIDE Out of the ﬂuids listed in Table 1, carbon dioxide is the supercritical ﬂuid of choice because it is nonﬂammable, nontoxic, inexpensive, and has near-ambient critical temperature. Hence, much of

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the attention in supercritical ﬂuid technology has been given to carbon dioxide-based processes. Carbon dioxide (OaCaO) is a nonpolar molecule, with a small polarity due to the presence of a quadrupole moment. Supercritical carbon dioxide can be described as hydrophobic solvent with polarity comparable to that of n-hexane. Hence, nonpolar or light molecules easily dissolve in supercritical CO2, whereas the polar or heavy molecules (e.g., polymers, disperse dyes, aliphatic fatty acids and their esters, aromatic acids, proteins, ﬁsh oils, metal complexes, etc.) have very poor solubilities. Some light organic compounds, either polar or nonpolar (e.g., acetone, methanol, ethanol, toluene, hexane, menthol, etc.), are used as cosolvents (also often called entrainers or modiﬁers) to enhance the solvating power and polarity of carbon dioxide. Supercritical carbon dioxide has been industrially used in a variety of processes, including coffee decaffeination, tea decaffeination, and extraction of fatty acids from spent barley, pyrethrum, hops, spices, ﬂavors, fragrances, corn oil, and color from red peppers. Other applications include polymerization, polymer fractionation, particle formation for pharmaceutical and military use, textile dyeing, and cleaning of machine and electronic parts.

SOLUBILITY IN SUPERCRITICAL CARBON DIOXIDE Solubility is the most important criterion affecting the efﬁcacy of most of the supercritical ﬂuid processes. For example, solubility can have a direct impact on the rate, yield, design, and economy of the process. Depending on the process of interest, either a high solubility or extremely low solubility may be desired. For example, high solubility is required in supercritical extraction processes. On the other hand, low solubility is required for CO2/organic solvent mixtures used in the supercritical antisolvent precipitation processes to manufacture particles (Chattopadhyay and Gupta 2001; 2002; Thote and Gupta 2005; Gupta and Kompella, 2006). Here the solubility affects yield, cost, and, most importantly, the size and morphology of the product. In the precipitation processes, nucleation is a strong function of supersaturation, which, in turn, depends on solubility. Solubility can have a remarkable effect on precipitation kinetics. For example, in the case of acetaminophen (Shekunov 1999), at 80 bar and 358 K, low solubility (w10K8 mole fraction) results in high supersaturation, high nucleation, and fast crystal growth, producing 1-–3-mm size particles. Whereas, at 250 bar and 353 K, high solubility (w10K5 mole fraction) results in low supersaturation and produces millimeter-sized acicular crystals in low yield. Similarly, in rapid expansion of supercritical solution to produce particles, solubility plays a key role (Thakur and Gupta 2005). The variation in solvent strength of a supercritical ﬂuid from gas-like to liquid-like values may be described qualitatively in terms of the density parameter, r, or the solubility parameter, d (square root of the cohesive energy density) calculated as (Williams et al. 2004): d2 Z

DE v

T

z

vE vv

T

ZT

vP vT

v

KP

(1)

where E is the internal energy, and v is the molar volume. Molar volume or density of supercritical ﬂuids is highly pressure/temperature dependent and can be varied from gas-like to liquid-like values, as shown in Figure 1. Similar characteristics are observed for plots of other density-dependent variables, such as enthalpy, entropy, viscosity, and diffusivity, versus pressure. The d for gaseous carbon dioxide is essentially zero; whereas, the value for liquid carbon dioxide is like that of a hydrocarbon (Figure 2). At 308C, there is a large increase in d upon condensation from vapor to liquid. Above the critical temperature, it is possible to tune the solubility parameter continuously over a wide range, with either a small isothermal pressure change or a small isobaric temperature change. This ability to tune the solvent strength of a supercritical ﬂuid is its unique feature, and it can be used to extract and then recover selected products. Note that density and d are more direct measures of the solvent strength of a supercritical ﬂuid than pressure. Solubility improves as the difference between solubility parameter of solute and supercritical CO2 decreases.

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25 25 20 δ(MPA)1/2

20

Liquid

15

15

10

Supercritical fluid

10

5

5

0

0

Gas

250

300 T (K

)

350

400

450 0

10

20

40

30

P

50

) Pa

(M

FIGURE 2 Solubility parameter of CO2. (From Williams, L. L., Rubin, J. B., and Edwards, H. W., Ind. Eng. Chem. Res., 4316, 4967–4972, 2004. With permission.)

A common feature of solubility data for single solutes dissolved in a supercritical ﬂuid is the existence of what has been termed crossover pressure (Chimowitz and Pennisi 1986). This is a pressure around which isotherms at various near-critical temperatures tend to converge. Figure 3 shows this behavior for phenanthrene solubility in carbon dioxide. Below the crossover pressure, an isobaric increase in temperature causes a solubility decrease, so that the solute is retrograde. 4500 313 K 323 K 333 K

y × 106

3000

1500

0 0

100

200 P (bar)

300

400

FIGURE 3 Mole fraction solubility (y) of phenanthrene in supercritical carbon dioxide versus pressure. (From Anitescu, G. and Tavlarides, L. L., J. Supercrit. Fluids, 10(3), 175–189, 1997.). Three isothermal lines cross at the “crossover pressure” of 165 bar.

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Above the crossover pressure, the opposite effect occurs. This behavior can be understood by considering two opposing effects of temperature on solubility (Chimowitz 2005). The vapor pressure of the solid solute always increases with temperature, while the density (or solvent power) of supercritical carbon dioxide decreases. Below the crossover pressure where the compressibility is larger, the density effect dominates, and the solubility decreases with increasing temperature. At pressures above the crossover pressure, the vapor-pressure effect dominates; hence solubility increases with temperature.

MEASUREMENT OF SOLUBILITY IN SUPERCRITICAL CARBON DIOXIDE Solubility is typically deﬁned as mole fraction (y2) or weight fraction (w2) of solute in the supercritical ﬂuid, which is in equilibrium with the bulk solute. The early solubility measurements were done in near-critical liquid carbon dioxide (61.3 bar, 298 K) by Francis (1954), in which he visually determined solubility of 261 organic compounds. A compilation of temperature and pressure ranges and the measurement method employed is provided by Bartle et al. (1991) for solubility of low volatile compounds in supercritical CO2 published until 1989. Since then, various methods to measure solubility in supercritical ﬂuids have been reviewed in the literature (Brunner 1994; McHugh and Krukonis 1994; Dohrn and Brunner 1995; Schneider 1998; Bristow et al. 2001; Christov and Dohrn 2002; Galia et al. 2002; Aim and Fermeglia 2003; Pauchon et al. 2004; Knox 2005). These methods can be divided into two major categories: static and dynamic.

STATIC METHODS In these methods, the solute is allowed to be in static contact for a long time with the supercritical ﬂuid in order to reach equilibrium. Depending on sampling and the type of high-pressure vessel used, there are three variations: analytical, synthetic, and gravimetric. Analytical Method In this method, a constant volume equilibrium vessel is used in which a compound is equilibrated with a known amount of supercritical ﬂuid. A small sample of the ﬂuid phase is removed and analyzed for concentration of the solute. For illustration, the basic apparatus of Sung and Shim (1999) is shown in Figure 4, and a more advanced apparatus of Bristow et al. (2001) is shown in Figure 5. The sample vessel is ﬁlled with the solute, and then vacuum is applied to remove air. Known amounts of cosolvent (if needed) and carbon dioxide are then pumped into the system. The ﬂuid is allowed to contact solute by a recirculation pump to signiﬁcantly reduce the equilibration time. Typically, a magnetic pump is used, as it has a small inside volume. Once equilibrium is reached, a small volume of sample is withdrawn, using a sample loop attached to the switching valve. The sample can be sent directly to high-pressure liquid chromatography for online analysis or collected for off-line analyses using other techniques. Solubility of solute, y2, in mole fractions is calculated as y2 Z

n2 n2 z n1 C n2 Vr1 C n2

(2)

where n1 and n2 are the moles of carbon dioxide and solute collected from the sample loop, respectively. For dilute solute concentrations, moles of carbon dioxide are approximated as the product of sample volume (V) and pure CO2 molar density (r1), as shown in Equation 2. When using a cosolvent, Equation 2 is modiﬁed so that n1 represents the sum of CO 2 and cosolvent moles.

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Solubility in Supercritical Carbon Dioxide

To vent

VP P

P

Solvent flush 6 1

3 2 Equilibrium cell

CO2 Pressure generator

Glass wool Dye

Dye reservoir

4 Magnetic pump

5

Glass wool filter

Constant temperature bath

Solvent trap

FIGURE 4 Basic apparatus for solubility measurements using a static/analytical method. VP is vacuum pump and connection for solvent ﬂush, 1–6 are valves, and P comprises pressure gauges. Operation steps: (a) evacuate the entire apparatus with all valves open except for valves 1 and 5; (b) isolate the apparatus by closing valve 6; (c) deliver CO2 from the cylinder to the apparatus at a desired pressure by operating pressure generator and opening valve 1; (d) close valve 1 and circulate CO2 using magnetic pump for about 2 hours to reach equilibrium; (e) close valves 3 and 4 to isolate the CO2C solute ﬂuid mixture; (f) open valve 5 to release the ﬂuid mixture into the solvent trap; (g) ﬂow solvent to ﬂush the solute deposited onto the walls; and (h) analyze the solution in the trap for solute concentration. (From Sung, H.-D. and Shim, J.-J., J. Chem. Eng. Data, 44(5), 985–989, 1999.)

Synthetic Method A variable volume view cell (Figure 6) is used for adjusting operating conditions. Typically, the vessel is equipped with a sapphire window for visual observations. A ﬁxed amount of solute is dissolved into a known amount of supercritical ﬂuid. Conditions are then adjusted to gradually reduce the solubility of the mixture and cause precipitation. The beginning of the precipitation, that is, the cloud point, is recorded as a measure of solubility condition. For measuring cloud point, a physical property can be used whose ﬁrst derivative with respect to the modulated variables undergoes a sharp change when the phase transition occurs. For a given solute/ﬂuid loading, many solubility points can be measured by varying temperature and pressure independently. This method does not require sample collection or its analysis. Solubility is calculated as y2 Z

n2 n 1 C n2

(3)

where n1 and n2 are the moles of carbon dioxide and solute taken in the variable-volume view cell, respectively. The synthetic method is very convenient for determining binary-phase equilibria and phase boundaries in multicomponent mixtures. The measurements can be performed in a relatively short time. Another interesting feature of this method is the low mass of the solute required to investigate a wide range of composition. Synthetic methods cannot be used for solutes that have the same

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Sample loop vent

Oven Pressure transducer

SW1 V3

Mobile phase reservoir

Sample loop Magnetic recirculation pump

HPLC pump

SW2

Sample vessel

Sample collection V4

V2 V1 V5 Check valves

Co-solvent Heat pump exchangers

CO2 pump

SW3 CO2 bottle

BPR Solvent-CO2 equilibration vent

Mixing chamber

Solvent reservoir

Vacuum pump

FIGURE 5 Apparatus for solubility measurements using a static/analytical method. V symbols represent valves to turn ﬂows on or off, and SW represents switching valves to divert ﬂows. (From Bristow, S., Shekunov, B. Y., and York, P., Ind. Eng. Chem. Res., 40(7), 1732–1739, 2001, reproduced with permission from the American Chemical Society.)

refractive index as CO2. Accuracy of the visual cloud point determination increased with the difference in the two refractive indices. For opaque systems or for solutes with near-CO2 refractive indices, alternate nonvisual techniques have been proposed such as the use of transmitted x-ray (Abedi et al. 1999) for determining phase transition. Gravimetric Method In this method, solute is kept in a small vial inside the pressure vessel containing supercritical ﬂuid (Sherman et al. 2000; Galia et al. 2002). The lid of the vial is such that the dissolved molecular solute can easily permeate through it, but the solute particles cannot (Figure 7). In a typical experiment, a solute of known amount is placed in a vial and the vessel is ﬁlled with a ﬂuid.

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T

P

5

1 4

2

11

8 9

10

7 6

3

FIGURE 6 Variable-volume view cell for use in the static/synthetic method of solubility measurement. Components follow: variable volume cell (1), screw pump (2), magnetic stirrer (3), magnetic bar (4), upper sampling line (5), lower sampling line (6), sapphire window (7), thermostated bath (8), light source (9), video camera (10), and monitor (11). (From Crampton, C., Charbit, G., and Neau, E., J. Supercrit. Fluids, 16(1), 11–20, 1999, reproduced with permission from Elsevier.)

Then, the ﬂuid reaches the vial, dissolves the solute, and brings it out. Over time, the bulk of the ﬂuid reaches the same equilibrium concentration as the ﬂuid inside the vial. The vessel is then solely depressurized, and the mass of remaining solute in the vial is gravimetrically measured. The solubility of the solute is then calculated as y2 Z

Dn2 Dn2 z Dn1 C Dn2 r1 DV C Dn2

(4)

where Dn2 is the initial minus ﬁnal moles of solute in the vial, Dn1 is the total moles of CO2 minus that in the vial, DV is the vessel minus vial volume, and r1 is the molar density of CO2. Although the method is relatively simple, it can be effectively used only for solids that exhibit solubility greater than 10K3 mole fraction, that do not melt under the experimental conditions, and that absorb a negligible amount of carbon dioxide. The modiﬁcation by Galia et al. (2002) extends this method to the solids with solubility of the order of 10K5 mole fraction. However, the drawback Pressure transducer CO2 intake

CO2 outlet

PT

Sapphire window

Thermowell

Filter paper External Perforated stir bar disc

Teflon tape 5 mL vial Internal stir bar

FIGURE 7 Pressure vessel for use in static/gravimetric method. (From Sherman, G., Shenoy, S., Weiss, R. A., and Erkey, C., Ind. Eng. Chem. Res., 39(3), 846–848, 2000, reproduced with permission from the American Chemical Society.)

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of the need of excessive time required to obtain equilibrium persists. This method has not been widely adopted due to low accuracy. In the static methods, inaccuracies may arise due to leaks from a large number of valves and ﬁttings. Hence, care must be taken to ensure a leak-proof apparatus. In addition, errors may also arise from the multiple samplings, especially when data at multiple pressures and temperatures are collected from a single solute/carbon dioxide loading. Withdrawing a large sample from the equilibration cell can cause a considerable pressure drop, which disturbs the phase equilibrium signiﬁcantly. In-line analysis can overcome the problem due to sample withdrawals. Ultraviolet, visible, and near-infrared spectroscopies have been successfully used for this in-line analysis of solute concentration (Haarhaus et al. 1995; Tuma and Schneider 1999; Wagner et al. 1999). A sectional drawing of a spectroscopic high-pressure cell of Wagner et al. (1999) is shown in Figure 8.

DYNAMIC METHOD In this method, the vessel is ﬁlled with a solute, and a supercritical ﬂuid continuously ﬂows through the vessel. Mild ﬂow rate is used so that the outlet stream is assumed to reach equilibrium, which is then analyzed for the solute concentration by chromatographic, spectroscopic, gravimetric, dielectric, and other techniques. The apparatus used by Bristow et al. (2001) is shown in Figure 9. Here, solute is ﬁlled in the sample vessel. Continuous ﬂows of supercritical ﬂuid or a ﬂuid mixture with cosolvent are maintained. For on-line analysis, such as using UV detector, the ﬂuid mixture is bypassed directly to the analyzer for baseline correction, and then the ﬂuid is allowed to pass through the sample vessel. For off-line analysis, the sample is collected in the solvent or cold trap for a given period of time (t), and then analyzed for solute amount. Solubility is calculated as y2 Z

n2 n2 Z n 1 C n2 Q 1 r1 t C n2

(5)

where n1 and n2 are the moles of carbon dioxide and solute collected in time t, respectively, Q1 is volumetric ﬂow rate of carbon dioxide, and r1 is molar density of carbon dioxide, both at the same conditions (typically, back-pressure regulator exit conditions). Beneﬁts of dynamic methods can be summarized as follows: † † † † †

The apparatus can be assembled from easily available parts. The sampling procedure is simple. A large amount of data can be obtained in a short time. In addition to equilibrium, fractionation data can be obtained. Carbon dioxide ﬂow measurement can be done with a simple gas ﬂow meter at the exit. Shortcomings of the dynamic methods include:

† A major factor that affects the dynamic method is the mass-transfer rate between ﬂuid and solute. There is always a possibility that the solute concentration has not reached its equilibrium value. Hence, experiments should be done by further increasing the residence time of the ﬂuid, to ascertain that the equilibrium has been reached. The mass transfer rate can change over time if the supercritical carbon dioxide causes agglomeration of the solute particles, or the overall particle surface area is reduced by dissolution of small particles in early experimental runs. To improve mass transfer by having a high surface area, the solute is typically coated onto silica beads (e.g., 300 mm diameter) before being loaded into the sample vessel. † Heavy solutes can clog the exit restrictor or metering valve that may cause solute hold-up, resulting in a lower amount of solute collected in the trap than the equilibrium amount. In fact, most nonreproducible solubilities may be attributed to erratic ﬂow due to a plugged restrictor.

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Nonmagnetic wire High-pressure connector

Bridgman piston

Cylinder screw Flange Teflon o-ring Pressure ring

Piston head Teflon sealing

High-pressure cell

Piston base

Piston support

Steel cap Sapphire window

Teflon ring

S N

Stirrer Magnet

Conical steel insert

Support for stirrer

Window screw

100 mm FIGURE 8 Sectional drawing of the spectroscopic high-pressure cell. (From Wagner, B., Nishioka, M., Tuma, D., Maiwald, M., and Schneider, G. M., J. Supercrit. Fluids, 16(2), 157–165, 1999. With permission.)

† Entrainment of solute droplets or solid ﬁne particles can occur at high ﬂow rates, resulting in more solute collection in the trap than the equilibrium amount. † At high pressures, if the density of supercritical carbon dioxide is higher than the solute, the solute can ﬂoat and be pushed out of the column, resulting in much higher solute collection in the trap compared to the equilibrium amount. † When solute mixtures are used, care must be taken so as not to deplete one of the components. † If the solute phase undergoes phase transition, it can remain undetected unless a sapphire solute vessel is used.

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Introduction

11

Vent Mass flow meter Oven

BPR SW2

UV detector

Solvent trap

Heat exchangers

Sample vessel

Solvent pump

CO2 pump

SW1

CO2 bottle Solvent reservoir

FIGURE 9 Apparatus for the determination of solubility using a dynamic method. BPR, back pressure regulator to maintain constant pressure in system; SW, switching valves to divert ﬂows. (From Bristow, S., Shekunov, B. Y., and York, P., Ind. Eng. Chem. Res., 40(7), 1732–1739, 2001, reproduced with permission from the American Chemical Society.)

MODELING OF SOLUBILITY IN SUPECRITICAL CARBON DIOXIDE MODELING WITH EQUATION OF STATES The solubility increases with increase in pressure at a ﬁxed temperature, owing to enhanced solvation due to greater attractive forces between the solute and carbon dioxide. A fundamental relationship for phase equilibrium (Prausnitz et al. 1999) can be used to relate fugacities of the solute in the solid and ﬂuid phases as follows: f2s Z f2v

(6)

where f with superscript s stands for solid phase and v, for the supercritical ﬂuid phase. For the supercritical ﬂuid phase, fugacity is written as a function of solute mole fraction (y2) and fugacity coefﬁcient (f2): f2v Z y2 f2 P

(7)

When the solid phase is considered a pure phase, fugacity in the solid phase can be written as 0 1 ðP s B v2 C f2s Z Ps2 fs2 exp@ dPA (8) RT Ps2

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Solubility in Supercritical Carbon Dioxide

where T is temperature, P is pressure, vs2 is the molar volume of the solid solute, Ps2 is vapor pressure of the solid, and R is gas constant (8.314 J/molK). Due to the low vapor pressures, the values of fs2 can be taken unity for most solutes that do not have a strong tendency of association. In addition, due to the incompressibility of the solids, values of vs2 can be assumed to be pressure independent. Hence, the solubility of a solid solute (y2) in CO2 ﬂuid can be written as y2 Z

Ps2 1 vs ðPKPs2 Þ exp 2 P f2 RT

(9)

vs ðPKPs Þ

where f12 exp 2 RT 2 is termed as the enhancement factor and P2s/P is the solubility in the ideal gas. The most important term in the above equation is f2, which can be far from unity and thus responsible for enhancement factor of as high as 1000 or even higher. The fugacity of the solute in ﬂuid phase (f2) can be calculated from (Prausnitz et al. 1999): ðv RT ln f2 Z N

vP vn2

T;v;n1

K

RT Pv dvKRT ln v RT

(10)

where n2 is the number of moles of solute, n1 is the number of moles of CO2, and v is the molar volume of the mixture. A suitable equation of state can be used to perform the integration and evaluate v. A popular equation of state is the one developed by Peng and Robinson (1976) using interaction parameters a and b: PZ

RT a K vKb vðv C bÞ C bðvKbÞ

(11)

From Equation 11, the equation to evaluate fugacity coefﬁcient f2 is derived as ln f2 Z

b2 b

Pv PðvKbÞ K1 Kln RT RT pﬃﬃﬃﬃﬃﬃﬃﬃﬃ 2ðy1 a1 a2 ð1Kk12 Þ C y2 a2 Þ b2 a v C 2:414b K ln K pﬃﬃﬃ a b vK0:414b 2 2bRT

(12)

where b2 and a2 are size and energy parameters for pure component 2. Similarly, for component 1, they are given as b1 Z 0:07780 RTc1 Pc1 RTc2 a2 Z 0:45724 Pc2

2

a1 Z 0:45724

2

RTc1 ; Pc1

b2 Z 0:07780

RTc2 Pc2

(13)

h pﬃﬃﬃﬃﬃﬃﬃﬃﬃﬃﬃ i2 1 C ð0:37464 C 1:54226u1 K0:26992u21 Þð1K T=Tc1 Þ

(14)

h pﬃﬃﬃﬃﬃﬃﬃﬃﬃﬃﬃ i2 1 C ð0:37464 C 1:54226u2 K0:26992u22 Þð1K T=Tc2 Þ

(15)

Mixture, size, and energy parameters can be evaluated using van der Waals one-ﬂuid mixing rules and usual combining rules with binary parameters, as in pﬃﬃﬃﬃﬃﬃﬃﬃﬃ a Z y21 a1 C 2y1 y2 a1 a2 ð1Kk12 Þ C y22 a2 ; b Z y21 b1 C y1 y2 ðb1 C b2 Þð1Kc12 Þ C y22 b2 (16) where c12 and k12 are adjustable parameters due to solute-CO2 interactions that are not accounted for. For evaluation of parameters, various nonquadratic mixing rules are also available (Prausnitz et

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Introduction

13

313.15 K 333.15 K 363.15 K 393.15 K PR EOS

y2 × 106

100

10 10

20 Pressure (Mpa)

30

FIGURE 10 The solubility of C. I. Disperse Orange 30 dye in supercritical carbon dioxide as a function of pressure. Lines are calculated with Peng-Robinson equation of state (Equation 12). (From Baek, J.-K., Kim, S., Lee, G.-S., and Shim, J.-J., Korean J. Chem. Eng., 21(1), 230–235, 2004.)

al. 1999; Sandler 1994). One example for the solubility of a dispersed dye calculated by using the above equation is shown in Figure 10 (Baek et al. 2004).

SIMPLE DENSITY CORRELATION OF SOLUBILITY DATA Solubility increases with pressure at a constant temperature. As mentioned earlier, solubility behavior appears complex. For example, solubility isotherms intersect each other as shown in Figure 11. However, the complexity disappears when log-scale solubility isotherms are plotted ¨ zcan et al. versus density (Kumar and Johnston 1988; Bartle et al. 1991; Shim and Johnston 1991; O ¨ zcan et al. (1997) derived an 1997; Mendez-Santiago and Teja 1999). Bartle et al. (1991) and O empirical equation for poor-solubility solutes correlating a modiﬁed enhancement factor (yP/Pref) with ﬂuid density, together with a term to correct the effect of temperature. Fat’hi et al. (1998) Mendez-Santiago and Teja (1999) derived a semiempirical equation from the theory of Chrastil (1982) and Levelt Sengers (1991), respectively, to correlate the logarithm of solute concentration with ﬂuid density. Kumar and Johnston (1988) derived the semilog and the log–log relationship between solubility and density that can explain the near-linear behavior. Sung and Shim (1999) modiﬁed Kumar and ¨ zcan Johnston’s equations into simpler forms that are similar to those of Fat’hi et al. (1998) and O et al. (1997): ln y Z A C B=T C Cr1

(17)

ln y Z A 0 C B 0 =T C C 0 ln r1

(18)

where y is the mole fraction solubility, T is the absolute temperature (K), r1 is the molar density of ﬂuid (mol/L), and A, B, C, A 0 , B 0 , and C 0 are constants speciﬁc to the given solute. Using above relationship, Sung and Shim (1999) obtained linear, parallel-solubility isotherms from the semilog plots (Figure 12). Kumar and Johnston (1988) showed that the ratio of the solute’s partial molar volume in the supercritical ﬂuid and the isothermal compressibility of the ﬂuid (k) is not a constant but a function of temperature, making the constant C 0 a function of T. Therefore, the constant A 0 in

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14

Solubility in Supercritical Carbon Dioxide 150 313.15 K 333.15 K 363.15 K 393.15 K

100 y x 106

423.15 K

50

0 50

150

250

350

P (bar)

FIGURE 11 Complex behavior of solubility of C. I. Disperse Red 60 dye versus pressure. Lines are best ﬁts. (From Sung, H.-D. and Shim, J.-J., J. Chem. Eng. Data, 44(5), 985–989, 1999.)

Equation 19 may be expressed as a function of temperature, resulting in the following equation: ln y Z a C b=T C ðc C d=TÞln r1

(19)

where a, b, c and d are constants. The solubility isotherms in the log–log plot are linear but the slopes decrease with temperature as shown in Figure 13. The semilog relationship with three

313.15 K 333.15 K 363.15 K 393.15 K Eq 17

y × 106

100

10

0

5

10 15 Density (mol/L)

20

FIGURE 12 Linear behavior of solubility of C. I. Disperse Orange 30 dye (in logarithm scale) versus density. Lines are those correlated with Equation 17. (From Baek, J.-K., Kim, S., Lee, G.-S., and Shim, J.-J., Korean J. Chem. Eng., 21(1), 230–235, 2004.)

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Introduction

15

y2 × 106

100

313.15 K 333.15 K 363.15 K 393.15 K 423.15K Eq 19

10

1 10.0 Density (mol/L) FIGURE 13 Solubility isotherms of C. I. Disperse Red 60 dye with varying slopes with temperature in supercritical carbon dioxide. Lines are correlated with Equation 19. (From Sung, H.-D. and Shim, J.-J., J. Chem. Eng. Data, 44(5), 985–989, 1999.)

constants is obviously simpler than the log–log relationship with four constants. However, either equation can be used to predict solubility of the sparingly soluble solutes at densities between 3 and 20 mol/L without a large error. Although the exact density for extremum depends on the type of solutes, a solubility minimum generally occurs at a density lower than 3 mol/L and a maximum above 15 mol/L. This interesting behavior has been analyzed by Kurnik and Reid (1981) and veriﬁed experimentally by Swaid et al. (1985), Swidersky et al. (1996), and Kraska et al. (2002). In addition to the two general modeling approaches discussed above, there are numerous efforts published in the literature that are not discussed here. Variations have come about due to the use of different equations of state, by accounting for speciﬁc interactions, and by using molecular modeling. This book provides a compilation of the published data on solubility in supercritical carbon dioxide. Data are presented in both tabular and graphical formats. Extrapolation of the data can be performed using the above correlations, that is, the model parameters can be regressed to the available data and then a prediction is made for extended conditions. In the graphs, smooth lines connecting data points are drawn as visual aids; these lines are not results of any model correlations.

GUIDE TO TABLES AND GRAPHS This compilation includes published data from the early 1960s to 2004. The data are presented here in the form of 1217 tables, covering 783 different compounds. Any misprinted solubility data have been identiﬁed by drawing them or by comparing with the graphs in the same source or with those in other sources. In the case of inconsistent data, we contacted original authors for conﬁrmation of the data. When conﬁrmation was not received, we corrected the data using ﬁgures and/or tables in the same source or from the author’s other publications. When the data in the source article are presented only in graphical form, especially in a logarithmic plot with a small span, we contacted authors to obtain the original numerical data. If the original data were not received, we extracted the data from the graphs by digitizing them using a drawing program. Furthermore, any inaccuracy in the names, molecular formula, and molecular weight in the sources was checked

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Solubility in Supercritical Carbon Dioxide

with SciFinder Scholar (from Chemical Abstract Services) and various other sources. For metal complexes, complex formulas and formula weights (FW) are provided. Instead of SI units, we selected more popular units such as bar, grams per kilogram, and moles per liter for pressure, mass and molar solubilities, and density of ﬂuid, respectively. However, temperature is provided in K. Although solubility data are reported in various forms such as y, w, M, S, or W (see Abbreviations listing for details). In this book, solubility data are presented as mole fraction solubility, y ! 106, for easy comparison of the solubilities. Therefore, the molar or mass solubility, including M, S, or W, were converted to y with known MW or FW of the compound. For materials such as polymers or mixtures whose molecular weights are not known, the solubility (M, S, or W) in the source was converted to the mass fraction solubility, w!106.

ARRANGEMENT OF TABLES AND GRAPHS The tables are arranged alphabetically by compound name. When multiple tables are available for the same compounds, the tables for solubility in pure CO2 appear ﬁrst, followed by those in cosolvent-modiﬁed CO2. The tables for pure CO2 are arranged in the order of the ﬁrst author’s name, while the tables for the cosolvent-modiﬁed CO2 are arranged by the name of the cosolvents. Each table consists of three to ﬁve columns, including those for temperature (T), pressure (P), the name and amount of cosolvent (if any), the molar solubility (M) or mass solubility (S or W) (if any), and the mole fraction solubility (y) or mass fraction solubility (w). When temperatures are the same, subsequent temperature values are omitted in each row block, as it is the same as the temperature at the top row of the block. The data in graphical form are provided as a visual aid and placed on the right side of corresponding tables. Here, mole fraction solubility or weight fraction solubility is plotted versus pressure. When possible, smooth curves through the data points are shown as a visual aid. The number of signiﬁcant ﬁgures for the solubility data has been kept to less than four, considering experimental uncertainty.

SYNONYMS Chemical compounds typically have several different names. In this book, synonyms have been added to each compound for the convenience of readers with diverse backgrounds. These compound synonyms were chosen from SciFinder Scholar, and by referring to CrossFire, ChemDraw, the Aldrich catalogue, and chemistry faculty members for difﬁcult names.

CARBON DIOXIDE DENSITY The density data of carbon dioxide was obtained from the National Institute of Standards and Technology website for thermophysical properties (http://webbook.nist.gov/chemistry, July 2005). For CO2, this source employs Span and Wagner (1996) for the calculation of PVT properties. For the convenience of readers, pure CO2 density, covering both one phase and two phases, is provided in Appendix A (Table A.1–Table A.3 and Figure A.1) for temperatures in the range from the triple point 216.59 (the trible point of CO2) to 1073.15 K, and pressures in the range of 1 to 2000 bar.

REFERENCES Abedi, S. J., Cai, H.-Y., Seyfaie, S., and Shaw, J. M., Fluid Phase Equilib., 158-160, 775–781, 1999. Aim, K. and Fermeglia, M., Solubility of solids and liquids in supercritical ﬂuids, In The Experimental Determination of Solubilities, Hefter, G. T. and Tomkins, R. P. T., Eds., Wiley Sons, Chichester, West Sussex, England; Hoboken, NJ, pp. 493–555, 2003. Anitescu, G. and Tavlarides, L. L., J. Supercrit. Fluids, 10(3), 175–189, 1997. Baek, J.-K., Kim, S., Lee, G.-S., and Shim, J.-J., Korean J. Chem. Eng., 21(1), 230–235, 2004. Bartle, K. D., Clifford, A. A., Jafar, S. A., and Shilstone, G. F., J. Phys. Chem. Ref. Data, 20(4), 13–56, 1991.

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Introduction

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Bristow, S., Shekunov, B. Y., and York, P., Ind. Eng. Chem. Res., 40(7), 1732–1739, 2001. Brunner, G., Gas extraction, In An Introduction to Fundamentals of Supercritical Fluids and the Application to Separation Process, Baumgertel, H., Franck, E. U., and Grunbein, W., Eds., New York, p. 117, 1994. Chattopadhyay, P. and Gupta, R. B., Ind. Eng. Chem. Res., 40(16), 3530–3539, 2001. Chattopadhyay, P. and Gupta, R. B., AIChE J, 48, 235–244, 2002. Chattopadhyay, P. and Gupta, R. B., Int. J. Pharm., 228(1–2), 19–31, 2001. Chimowitz, E. Z., Introduction to Critical Phenomena in Fluids, Oxford University Press, Oxford, 2005. Chimowitz, E. H. and Pennisi, K. J., AIChE J, 32(10), 1665–1676, 1986. Chrastil, J. Phys. Chem., 86, 3016–3021, 1982. Christov, M. and Dohrn, R., Fluid Phase Equilib., 202(1), 153–218, 2002. Crampton, C., Charbit, G., and Neau, E., J. Supercrit. Fluids, 16(1), 11–20, 1999. Dohrn, R. and Brunner, G., Fluid Phase Equilib., 106(1–2), 213–282, 1995. Fat’hi, M. R., Yamini, Y., Sharghi, H., and Shamsipur, M. J., Chem. Eng. Data, 43, 400–402, 1998. Francis, A. W., J. Phys. Chem., 58, 1099, 1954. Galia, A., Argentino, A., Scialdone, O., and Filardo, G., J. Supercrit. Fluids, 24(1), 7–17, 2002. Gupta, R. B. and Johnston, K. P., Supercritical ﬂuid separation Perry’s Chemical Engineers’ Handbook, McGraw Hill, New York, 2006. Gupta, R. B. and Kompella, U. B., Nanoparticle Technology for Drug Delivery, Taylor and Francis, New York, pp. 53–84, 2006. Haarhaus, U., Swidersky, P., and Schneider, G. M., J. Supercrit. Fluids, 8(2), 100–106, 1995. Kiran, E., Debenedetti, P. G., and Peters, C. J., Supercritical Fluids: Fundamentals and Applications, Kluwer Academic Publishers, Boston, 2000. Knox, D. E., Pure App. Chem., 77(3), 513–530, 2005. Kraska, T., Leonhard, K. O., Tuma, D., and Schneider, G. M., J. Supercrit. Fluids, 23(3), 209–224, 2002. Kumar, S. K. and Johnston, K. P., J. Supercrit. Fluids, 1(1), 15–22, 1988. Kurnik, R. T. and Reid, R. C., AIChE J, 27(5), 861–863, 1981. Levelt Sengers, J. M. H., In Supercritical Fluid Technology: Reviews in Modern Theory and Technology, Bruno, T. J. and Ely, J. F., Eds., CRC Press, Boca Raton, FL, pp. 1–56, 1991. McHardy, J. and Sawan, S. P., Supercritical Fluid Cleaning: Fundamentals, Technology, and Applications, Noyes Publications, Westwood, NJ, 1998. McHugh, M. and Krukonis, V., Supercritical Fluid Extraction, 2nd ed., Butterworth-Heinemann, Boston, 1994. Mendez-Santiago, J. and Teja, A. S., Fluid Phase Equilib., 158-160, 501–510, 1999. Mukhopadhyay, M., Natural Extracts Using Supercritical Carbon Dioxide, CRC Press, Boca Raton, FL, 2000. ¨ zcan, A. S., Clifford, A. A., Bartle, K. D., and Lewis, D. M., J. Chem. Eng. Data, 42, 590–592, 1997. O Pauchon, V., Cisse, Z., Chavret, M., and Jose, J., J. Supercrit. Fluids, 32(1–3), 115–121, 2004. Peng, D.-Y. and Robinson, D. B., Ind. Eng. Chem. Res., 15(1), 59–64, 1976. Prausnitz, J. M., Lichtenthaler, R. N., and de Azevedo, E. D., Molecular Thermodynamics of Fluid-Phase Equilibria, 3rd ed., Prentice-Hall, Upper Saddle River, NJ, 1999. Sandler, S. I., Models for Thermodynamic and Phase Equilibria Calculations, Marcel Dekker, New York, 1994. Schneider, G. M., J. Supercrit. Fluids, 13(1–3), 5–14, 1998. Shekunov, B. Yu, Hanna, M., and York, P., J. Cryst. Growth, 198–199, 1999. See also p. 1345. Sherman, G., Shenoy, S., Weiss, R. A., and Erkey, C., Ind. Eng. Chem. Res., 39(3), 846–848, 2000. Shim, J.-J. and Johnston, K. P., J. Phys. Chem., 95, 353–360, 1991. Span, R. and Wagner, W., J. Phys. Chem. Ref. Data, 25(6), 1509–1596, 1996. Sung, H.-D. and Shim, J.-J., J. Chem. Eng. Data, 44(5), 985–989, 1999. Swaid, I., Nickel, D., and Schneider, G. M., Fluid Phase Equil., 21, 95–112, 1985. Swidersky, P., Tuma, D., and Schneider, G. M., J. Supercrit. Fluids 9, 12–18, 1996. Taylor, L. T., Supercritical Fluid Extraction, Wiley, New York, 1996. Thakur, R. and Gupta, R. B., Ind. Eng. Chem. Res., 44(19), 7380–7387, 2005. Thote, A. and Gupta, R. B., Nanomed.: Nanotechnol. Biol. and Med., 1(1), 85–90, 2005. Tuma, D. and Schneider, G. M., Fluid Phase Equilib., 158-160, 743–757, 1999. Wagner, B., Nishioka, M., Tuma, D., Maiwald, M., and Schneider, G. M., J. Supercrit. Fluids, 16(2), 157–165, 1999.

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Williams, J. R. and Clifford, A. A., Supercritical Fluid Methods and Protocols, Humana Press, Totowa, NJ, 2000. Williams, L. L., Rubin, J. B., and Edwards, H. W., Ind. Eng. Chem. Res., 4316, 4967–4972, 2004. York, P., Kompella, U. B., and Shekunov, B., Supercritical Fluid Technology for Drug Product Development, Marcel Dekker, New York, 2004.

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1

Solubility Data A

Acenaphthene (C12H10; MW=154.21)

[A-1]

106

313.15 K 323.15 K 333.15 K 343.15 K 353.15 K 373.15 K

2000

y x 106

yx T (K) P (bar) 313.15 75 29.4 80 56.1 85 127.0 323.15 75 27.9 80 41.2 85 73.7 90 111.0 100 334.0 333.15 75 38.1 80 50.7 85 69.1 90 94.2 100 234.0 343.15 75 56.6 80 77.5 85 114.0 90 134.0 353.15 75 91.8 80 110.0 85 146.0 90 164.0 373.15 75 170.0 80 190.0 85 233.0 90 248.0 100 413.0 150 2370.0 Synonym: 1,2-Dihydroacenaphthylene Source: Lou, X.; Janssen, H.-G.; Cramers, C. A. J. Chromatogr. A (1997),785(1-2), 57-64.

1000

0 50

100 P (bar)

150

19

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20

Solubility in Supercritical Carbon Dioxide

Acenaphthene (C12H10; MW=154.21)

[A-2]

106

308.15 K 318.15 K 328.15 K 338.15 K 348.15 K

y x 106

yx T (K) P (bar) 308.15 121.6 2006 152.0 2122 182.4 2393 212.8 2622 243.2 2693 273.6 2745 304.0 2818 334.4 3112 354.6 3105 318.15 121.6 1833 152.0 2560 182.4 2877 212.8 3424 15000 243.2 3657 273.6 3661 304.0 4193 334.4 4286 354.6 4390 10000 328.15 121.6 2106 152.0 2902 182.4 3541 212.8 4015 243.2 4451 5000 273.6 4601 304.0 4830 334.4 5536 354.6 5943 338.15 121.6 1369 0 152.0 3083 182.4 4712 100 212.8 5982 243.2 7110 273.6 8123 304.0 8680 334.4 9146 354.6 9410 348.15 121.6 1277 152.0 3029 182.4 5381 212.8 7818 243.2 9905 273.6 11781 304.0 13112 334.4 13947 354.6 13995 Synonym: 1,2-Dihydroacenaphthylene Source: Yamini, Y.; Bahramifar, N., J. Chem. Eng. Data (2000), 45(1), 53-56.

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200 300 P (bar)

400

Solubility Data A

21

Acenaphthene (1) + Fluoranthene (2) + Triphenylene (3) Mixture y2 x

y3 x

15 18 24 25 28 34 38 41 43 13 21 27 39 45 49 51 58 63 4 23 54 74 102 117 116 116 124 N/A 2 25 39 34 27 84 96 121

10000 y x 106

y1 x

308 121.6 2395 316 152.0 2622 368 182.4 2984 438 212.8 3079 495 243.2 3283 536 273.6 3517 582 304.0 3704 636 334.4 3902 663 354.6 3991 674 318 121.6 2507 284 152.0 3126 423 182.4 3811 532 212.8 4290 637 243.2 4614 729 273.6 4781 776 304.0 5284 912 334.4 5460 948 354.6 5702 1016 328 121.6 2445 160 152.0 3608 301 182.4 5081 505 212.8 6180 666 243.2 7069 850 273.6 8042 1010 304.0 7667 1096 334.4 8567 1214 354.6 8880 1299 338 121.6 1492 52 152.0 3440 208 182.4 4769 693 212.8 6297 995 243.2 7143 966 273.6 8343 1068 304.0 9898 1334 334.4 5172 1523 354.6 4737 1573 Source: Yamini,Y.; Bahramifar,N. J. Chem. Eng. Data (2000), 45(6), 1129-1132.

[A-3]

106 308 K 318 K 328 K 338 K

5000 Acenaphthene

0 100

200

300

400

P (bar)

1500 y x 106

P (bar)

106

1000

308 K 318 K 328 K 338 K

500 Fluoranthene

0 100

200

300

400

P (bar) 150

y x 106

T (K)

106

100

308 K 318 K 328 K 338 K

50

0 100

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Triphenylene

200 300 P (bar)

400

22

Solubility in Supercritical Carbon Dioxide

Acetaminophen (C8H9NO2; MW=151.16)

313

353

P (bar) 100 125 175 210 250 100 125 175 210 250 80 100 150 200 250 80 100 125 150 225

(mol%)

0 0 0 0 0 0.85 0.85 0.85 0.85 0.85 0 0 0 0 0 0.85 0.85 0.85 0.85 0.85

[A-4]

y2) x 106 0.370 0.650 1.080 1.370 1.780 1.310 1.770 2.840 3.330 4.320 0.072 0.180 1.360 4.070 8.140 0.022 0.098 0.760 2.910 8.890

10 CO2, 313 K CO2, 353 K EtOH, 313 K EtOH, 353 K

y x 106

T (K)

Ethanol1)

5

0 0

100

200

300

P (bar)

1: Cosolvent in CO2. 2: Measured by off-line dynamic method. Synonyms: N-(4-Hydroxyphenyl)acetamide; 4'-Hydroxyacetanilide Source: Bristow, S.; Shekunov, B. Y.; York, P. Ind. Eng. Chem. Res. (2001), 40(7), 1732-1739.

Acetaminophen (C8H9NO2; MW=151.16)

[A-5]

Ethanol1) y2) x 106 (mol %) 4 313 250 0.00 0.079 0.42 0.280 0.84 0.540 1.66 1.120 2 2.47 1.330 3.26 1.520 4.03 2.550 4.78 3.350 0 1: Cosolvent in CO2. 0 2: In the original article the solubility is written in "mol" but the primary author confirmed it "mole fraction". Synonyms: N-(4-Hydroxyphenyl)acetamide; 4'-Hydroxyacetanilide Source: Bristow, S.; Shekunov, B. Y.; York, P. Ind. Eng. Chem. Res. (2001), 40(7), 1732-1739. P(bar)

y x 106

T(K)

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2

4

Ethanol (mol%)

6

Solubility Data A

23

Acetaminophen (C8H9NO2, MW=151.16) 313 353

P (bar) 90 150 90 150

yx

14

6 9 2 11

y x 106

T (K)

[A-6]

106

Synonyms: N-(4Hydroxyphenyl)acetamide; 4'Hydroxyacetanilide Source: Shekunov, B. Y.; Bristow, S.; Chow, A. H. L.; Cranswick, L.; Grant, D. J. W.; York, P. Cryst. Growth Des. (2003), 3(4), 603-610.

313 K 353 K

7

0 50

100

150

P (bar)

Acetic acid (C2H4O2 ; MW=60.05)

[A-7]

106

60000 313.2 K 333.2 K 353.2 K

40000 y x 106

yx T (K) P (bar) 313.2 11 11100 21 6600 31 5800 41 6100 51 4800 61 6900 333.2 31 12600 41 11900 51 12000 61 13500 71 14400 81 18100 91 25200 353.2 21 31600 36 24200 51 23800 66 24900 81 28800 96 36300 111 52000 Source: Bamberger, A.; Sieder, G.; Maurer, G. J. Supercrit. Fluids (2000), 17(2), 97-110.

20000

0 0

CAT4240—CHAPTER 1—31/10/2006—18:14—MUGUNTHAN—XML MODEL C – pp. 19–73

50 P (bar)

100

24

Solubility in Supercritical Carbon Dioxide

Acetone (C3H6O; MW=58.08) T (K) P (bar)

102

Mx (mol/L)

[A-8]

y1) x 106

3890 50 1 11800 60 4 17700 70 8 23600 80 15 100 64 44600 1: Calculated from M. Source: Fedotov, A. N.; Simonov, A. P.; Popov, V. K.; Bagratashvili, V. N. J. Phys. Chem. B (1997),101(15), 29292932.

y x 106

313

25000

0 40

70 P (bar)

Acetone (C3H6O; MW=58.08)

100

[A-9]

y x 106

303 K 323 K 332.9 K

100000

y x 106

T(K) P(bar) 303 10.5 36500 20.5 22500 30.5 16300 40.5 13400 41.0 13100 41.0 13300 50.6 11500 51.0 11400 55.0 10300 323 10.5 76600 21.0 46700 25.5 39500 31.0 35600 40.5 30100 41.0 30300 51.0 27400 56.1 26600 61.0 26200 70.8 26800 71.0 26500 332.9 10.5 108700 20.5 64500 21.0 64700 30.5 48700 36.0 45000 40.5 41900 50.6 38300 51.0 38000 60.6 36500 61.0 36500 71.0 37000 81.0 39000 Source: Bamberger, A.; Maurer, G. J. Chem. Thermodyn. (2000), 32(5), 685-700.

50000

0 0

CAT4240—CHAPTER 1—31/10/2006—18:14—MUGUNTHAN—XML MODEL C – pp. 19–73

30

60 P (bar)

90

Solubility Data A

25

Acetonitrile (C2H3N; MW=41.05) Mx (mol/L)

[A-10] 50000

y1) x 106

313

50 1 3890 6650 70 3 9450 80 6 15200 90 17 34100 100 49 110 73 46900 1: Calculated from M. Synonym: Methyl cyanide Source: Fedotov, A. N.; Simonov, A. P.; Popov, V. K.; Bagratashvili, V. N. J. Phys. Chem. B (1997),101(15), 29292932.

y x 106

T (K) P (bar)

102

25000

0 40

80

120

P (bar)

p-Acetoxyacetanilide (C10H11NO3; MW=193.20) P (bar)

308.15

328.15

348.15

100 140 160 180 200 100 120 140 160 180 200 120 140 160 180 200

yx

7.9 21.0 24.2 26.5 28.4 3.6 10.9 34.3 48.2 58.3 64.4 7.7 16.5 49.7 71.2 82.7

[A-11] 90 308.15 K 328.15 K 348.15 K

60 y x 106

T (K)

106

30

0 50

Synonyms: 4-Acetamidophenyl acetate; 4'-Acetoxyacetanilide Source: Jouyban, A.; Rehman, M.; Shekunov, B. Y.; Chan, H.-K.; Clark, B. J.; York, P. J. Pharmac. Sci. (2002), 91(5), 1287-1295.

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100

150 P (bar)

200

26

Solubility in Supercritical Carbon Dioxide

p-Acetoxyacetanilide (C10H11NO3; MW=193.20) 106

yx T (K) P (bar) 313 90 13 150 67 353 90 25 150 120 Synonyms: 4-Acetamidophenyl acetate; 4'-Acetoxyacetanilide Source: Shekunov, B. Y.; Bristow, S.; Chow, A. H. L.; Cranswick, L.; Grant, D. J. W.; York, P. Cryst. Growth Des. (2003), 3(4), 603-610.

[A-12]

y x 106

140 313 K 353 K

70

0 50

100

150

200

P (bar)

Acetylsalicylic acid (C9H8O4; MW=180.16)

[A-13]

106

yx T (K) P (bar) 313 100 83 150 164 200 260 250 290 323 100 70 150 250 200 336 250 361 Synonyms: 2-Acetoxybenzoic acid; Aspirin Source: Bettini, R.; Rossi, A.; Levezzini,E.; Frigo, E.; Pasquali, I.; Giordano, F. J. Therm. Anal. Cal. (2003), 73(2), 487-497.

y x 106

400

200 313 K 323 K

0 50

150

250

P (bar)

Acridine (C13H9N; MW=179.22) T (K) P1) (bar)

[A-14]

Methanol2)

y x 106

y1) x 106 4000 (mol %) CO2 323 95.8 0 15 MeOH 3000 116.2 0 130 144.2 0 184 172.3 0 265 2000 241.2 0 528 309.4 0 879 1000 411.7 0 1013 96.5 96 5 117.0 251 5 0 143.5 5 1087 50 150 250 171.5 5 1631 242.0 5 2866 P (bar) 413.9 5 3403 1: Obtained by digitizing the graph in the original article. 2: Cosolvent in CO2. Synonyms: 9-Azaanthracene; 2,3-Benzoquinoline Source: Van Alsten, J. G.; Eckert, C. A. Preprints of Papers - Am. Chem. Soc., Div. Fuel Chem. (1985), 30(3), 13-15.

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350

450

Solubility Data A

27

Acridine (C13H9N; MW=179.22) T (K)

Cosolvent (mol%)

y x 106

120 150 150 200 280 350

0.0 585 0.0 743 4000 0.0 751 0.0 775 0.0 1090 3000 0.0 1260 Acetone 120 3.5 1250 120 3.5 1250 2000 200 3.5 1800 200 3.5 1920 250 3.5 1970 1000 300 3.5 2050 350 3.5 2210 Methanol 0 120 3.5 2400 150 3.5 2770 0 250 3.5 3110 250 3.5 2900 300 3.5 3240 300 3.5 3050 350 3.5 3040 350 3.5 3100 Synonyms: 9-Azaanthracene; 2,3-Benzoquinoline Source: Dobbs, J. M.; Wong, J. M.; Lahiere, R. J.; Johnston, K. P. Ind. Eng. Chem. Res. (1987), 26(1), 56-65.

CO2 Acetone MeOH

y x 106

308.2

P (bar)

[A-15]

100

Acridine (C13H9N; MW=179.22) T (K) 323

P (bar) 94.1 104.4 118.2 132.0 138.9 145.8 173.3 242.3 345.7 104.4 118.2 145.8 207.8 276.7 345.7

1)

Cosolvent (mol %) Methanol 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 2.5 2.5 2.5 2.5 2.5 2.5

y x 106 22 99 207 498 1100 830 1570 2490 5170 563 162 385 1560 4150 6530

CAT4240—CHAPTER 1—31/10/2006—18:14—MUGUNTHAN—XML MODEL C – pp. 19–73

200

300

400

P (bar)

[A-16]

28

Solubility in Supercritical Carbon Dioxide

3.9 854 3.9 1380 3.9 2110 3.9 3290 3.9 4310 3.9 7030 2.5 124 10000 2.5 480 2.5 1130 2.5 1950 2.5 2280 7500 2.5 2970 2.5 5980 2.5 9810 Acetone 5000 323 104.4 1.0 93 111.3 1.0 185 118.2 1.0 224 132.0 1.0 305 2500 145.8 1.0 571 173.3 1.0 1360 242.3 1.0 2260 345.7 1.0 4000 0 104.4 2.5 232 50 118.2 2.5 649 145.8 2.5 1100 166.0 2.5 1240 207.8 2.5 2550 276.7 2.5 2430 345.7 2.5 3770 380.2 2.5 4090 1: Cosolvent in CO2 on a solute-free basis. Synonyms: 9-Azaanthracene 2,3-Benzoquinoline Source: Van Alsten, J. G.; Eckert, C. A. J. Chem. Eng. Data (1993), 38(4), 605-610.

323 K, 1.0% MeOH 323 K, 2.5% MeOH 323 K, 3.9% MeOH 323 K, 1.0% Acet 323 K, 2.5% Acet 343 K, 2.5% MeOH

y x 10

6

104.4 118.2 132.0 173.3 242.3 345.7 343 118.2 145.8 173.3 207.8 242.3 276.7 311.2 414.6

Acridine (C13H9N; MW=179.22)

P (bar)

[A-17]

3000

308.2 K 318.2 K 328.2 K 343.2 K

6

206 330 638 907 1060 1250 118 247 326 681 1130 1510 1550 1730

350

4000

y x 106

y x 10

T (K) P (bar) 308.25 102.5 122.2 151.6 200.0 270.3 350.4 318.15 101.8 110.6 122.8 152.2 200.0 270.1 279.4 352.2

200

2000

1000

0 100

CAT4240—CHAPTER 1—31/10/2006—18:14—MUGUNTHAN—XML MODEL C – pp. 19–73

200

300 P (bar)

400

Solubility Data A

29

328.25

101.6 40 110.6 96 122.5 194 151.0 617 201.1 1165 279.6 1940 355.7 2270 343.15 111.2 60 130.1 196 160.7 615 199.7 1200 251.4 1950 300.1 2850 364.1 3660 Synonyms: 9-Azaanthracene; 2,3-Benzoquinoline Source: Schmitt, W. J.; Reid, R. C. J. Chem. Eng. Data (1986), 31(2), 204-212.

Acridine(1) + Anthracene(2) Mixture T (K)

P (bar)

1)

Methanol (mol %)

y1 x 106

[A-18] y2 x 106

Acridine Anthracene

6

323

y x 10

104.4 1.0 136 19.9 138.9 1.0 845 155 207.8 1.0 2080 181 276.7 1.0 5380 461 345.7 1.0 8620 741 1: Cosolvent in CO2 on a solute-free basis. Source: Van Alsten, J. G.; Eckert, C. A. J. Chem. Eng. Data (1993), 38(4), 605-610.

10000

5000

0 50

150

250

350

P (bar) Adamantane (C10H16; MW=136.23) T (K) P (bar) 343.0 135.0 145.0 160.0 170.0 175.0 190.0 210.0 290.5 330.0 400.0 500.0 660.0

S (g/L) 3.23 5.44 8.40 10.30 10.95 12.83 14.90 21.38 24.00 25.57 27.10 26.93

1)

y x 10

6

2393 3590 4883 5631 5835 6422 7014 8756 9433 9526 9564 8958

CAT4240—CHAPTER 1—31/10/2006—18:14—MUGUNTHAN—XML MODEL C – pp. 19–73

[A-19]

30

382.0

402.0

157.0 160.0 165.0 175.0 185.0 190.0 200.0 200.0 210.0 210.0 228.0 228.0 290.0 320.0 360.0 400.0 500.0 600.0 750.0 185.0 185.0 194.0 194.0 195.0 195.0 200.0 210.0 210.0 210.0 228.0 228.0 246.0 246.0 277.0 279.0 304.0 326.0 330.5 354.0 357.5 370.0 401.0 440.0 540.0 540.0 550.0 650.0 660.0 750.0 850.0 172.0 185.0

5.18 5.88 6.52 8.20 10.16 11.74 13.74 13.76 16.30 15.82 19.46 20.03 27.74 31.87 35.18 37.53 41.47 42.74 42.29 9.19 9.62 11.21 11.88 11.76 11.12 12.81 15.42 15.85 15.60 20.49 20.21 25.05 24.89 32.54 32.22 38.10 41.58 42.76 45.75 45.34 48.80 51.27 56.11 61.82 61.35 63.15 64.55 65.53 63.97 63.53 8.35 10.78

4131 4563 4848 5646 6546 7342 8153 8164 9241 8971 10320 10620 12700 13930 14650 15050 15510 15220 14280 7276 7614 8375 8871 8730 8259 9232 10520 10810 10640 12840 12670 14640 14550 17320 17060 19040 19940 20340 20980 20700 21890 22170 23320 23860 23690 24220 23540 23790 22440 21600 8495 10020

40000

343.0 K 362.5 K 382.0 K 402.0 K

30000

y x 106

362.5

Solubility in Supercritical Carbon Dioxide

20000

10000

0 0

CAT4240—CHAPTER 1—31/10/2006—18:14—MUGUNTHAN—XML MODEL C – pp. 19–73

300

600 P (bar)

900

Solubility Data A

31

211.0 18.66 14820 218.0 19.13 14660 218.0 18.27 14010 225.0 22.40 16570 225.0 22.00 16280 228.0 22.02 16070 240.0 25.79 17840 259.5 31.82 20390 332.0 51.96 27290 475.0 82.26 35310 600.0 94.48 36910 1: Calculated from S. Synonym: Tricyclo[3.3.1.13,7]decane Source: Swaid, I.; Nickel, D.; Schneider, G. M. Fluid Phase Equil. (1985), 21, 95-112.

Adamantane (C10H16; MW=136.23) y x 10

8000 6

413 885 2330 4390 6400

y x 10

T (K) P (bar) 333 77.0 101.7 125.9 166.5 200.6

[A-20]

6

4000

Synonym: Tricyclo[3.3.1.13,7]decane Source: Smith, V. S.; Teja, A. S.; J. Chem. Eng. Data (1996), 41(4), 923-925.

0 50

150 P (bar)

Aesculetin (C9H6O4; MW=178.14)

[A-21] 0.6

1.82 2.76 4.02 4.18

0.228 0.345 0.502 0.522

y x 10

500 1000 1500 2000

6

T (K) P1) (bar) S1) (μg/Nl2)) y3) x 106 313.15

250

1: Obtained by digitizing the graph in the original article. 2: Nl means "Normliter" which is one liter at 273.15 K and 1 atm. 3: Calculated from S. Synonyms: 6,7-Dihydroxycoumarin; Esculetin Source: Stahl, E.; Schilz, W.; Schutz, E.; Willing, E. Angew. Chem. Int. Ed. (1978), 17, 731-738.

0.4

0.2 0

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1000 P (bar)

2000

32

Solubility in Supercritical Carbon Dioxide

Albumin

[A-22]

313

180

11.0 20.0 38.3 43.6

w x 106

90

50 30 20 20

6

60 w x 10

Cosolvent T (K) P (bar) (wt%) Acetone 313 180 7.0 14.5 25.9 28.5 Ethanol 313 180 7.0 15.0 24.4 31.5 CH 2 Cl 2

30 10 10 10

30

Acetone Ethanol CH2Cl2

0

40 60 80 50

0

20

40

60

Cosolvent (wt%)

Source: Domingo,C.,Vega, A Fanovich, M. A., Elvira, C., Subra, P., J. Appl. Polym. Sci . (2003), 90(13), 3652-3659.

Ametryne (C9H17N5S; MW=227.33) 189 244 200 209 216 209 251 266 266 297 315 150 282 437 526 765 854 1059 1262 1326 1185 1156 869

1500 313.15 K 333.15 K 353.15 K

1000 6

y x 10

[A-23]

6

y x 10

T (K) P (bar) 313.15 107.1 125.9 142.5 156.7 177.3 196.8 216.2 218.4 243.9 285.2 295.1 333.15 111.0 121.7 135.3 145.0 151.8 164.3 187.2 223.0 263.2 299.2 302.1 304.9

1)

500

0 0

100

CAT4240—CHAPTER 1—31/10/2006—18:14—MUGUNTHAN—XML MODEL C – pp. 19–73

200 P (bar)

300

400

Solubility Data A

33

353.15 100.8 47 119.2 76 145.8 116 151.2 225 151.8 314 179.9 780 216.7 1188 252.2 1297 274.9 1197 289.9 966 290.2 926 291.9 854 825 293.9 1: Obtained by digitizing the graph in the original article. Synonym: 2-Ethylamino-4-isopropylamino-6-methylthio-1,3,5-triazine Source: Knez, Z.; Rizner-Hras, A.; Kokot, K.; Bauman, D. Fluid Phase Equil. (1998), 152(1), 95-108.

Ametryne (C9H17N5S; MW=227.33)

6

2000

y x 10

1) 1,2) 3) 6 T (K) P (bar) S (g/L) y x 10 313.15 0.04 27 80 85 0.11 60 90 0.41 158 95 0.93 306 100 1.46 446 110 2.26 636 120 2.85 766 150 4.50 1110 180 6.32 1490 1830 210 8.05 1: Obtained by digitizing the original graph in the original article.

[A-24]

1000

0 50

100

2: The data may have a large reading error as the source graph is small. 3: Calculated from S. Synonym: 2-Ethylamino-4-isopropylamino-6-methylthio-1,3,5-triazine Source: Rodrigues, S.V.; Nepomuceno, D.; Martins, L. V.; Baumann, W. Fresenius' J. Anal. Chem. (1998), 360(1), 58-61.

CAT4240—CHAPTER 1—31/10/2006—18:14—MUGUNTHAN—XML MODEL C – pp. 19–73

150 P (bar)

200

250

34

Solubility in Supercritical Carbon Dioxide

[A-25]

2-Aminobenzoic acid (C7H7NO2; MW=137.14) T(K)

P(bar)

y x 106

120 150 200 250 300 350

0.0 80 0.0 99 1200 0.0 113 0.0 127 0.0 135 0.0 161 Acetone 800 90 3.5 160 120 3.5 250 150 3.5 270 180 3.5 290 400 250 3.5 390 300 3.5 450 Methanol 90 3.5 480 0 120 3.5 600 0 150 3.5 690 200 3.5 820 250 3.5 910 300 3.5 960 Synonyms: Anthranilic acid; 2-Carboxyaniline Source: Dobbs, J. M.; Wong, J. M.; Lahiere, R. J.; Johnston, K. P. Ind. Eng. Chem. Res. (1987), 26(1), 56-65.

CO2 Acetone Methanol

y x 10

6

308.15

Cosolvent (mol%)

100

200

300

P (bar)

2-Aminobenzoic acid (C7H7NO2; MW=137.14) T (K)

1)

P (bar) Menthol

400

[A-26]

6

y x 10

313.1

Pure CO2, 313.13K Pure CO2, 323.13K w/Menthol, 313.13K w/Menthol, 323.13K

6000

y x 10

6

96 0 13 129 0 25 163 0 32 196 0 38 323.1 96 0 5 130 0 24 163 0 31 197 0 42 237 0 56 313.1 129 saturated 440 163 saturated 1051 196 saturated 3131 323.1 96 saturated 19 163 saturated 1363 197 saturated 3416 237 saturated 6641 1: Cosolvent that is fully saturated in CO2. Synonyms: Anthranilic acid; 2-Carboxyaniline Source: Thakur, R., PhD Dissertation, Auburn University, Auburn, Alabama, 2006.

4000

2000

0 50

CAT4240—CHAPTER 1—31/10/2006—18:15—MUGUNTHAN—XML MODEL C – pp. 19–73

150 P (bar)

250

Solubility Data A

35

[A-27]

2-Aminobenzoic acid (1) + Anthracene (2) Mixture1) 2)

1200

6

P (bar)

800

y x 10

Methanol y1 x 106 y2 x 106 (mol%) 308.2 120 0.0 90 47 150 0.0 95 60 200 0.0 110 71 300 0.0 150 82 350 0.0 170 84 120 3.5 630 66 120 3.5 580 65 150 3.5 670 75 200 3.5 770 82 300 3.5 980 88 350 3.5 1060 92 1: The solubility was measured from a mixture of solids 1 and 2 of 50:50 wt%. 2: Cosolvent in CO2. Source: Dobbs, J. M.; Johnston, K. P. Ind. Eng. Chem. Res. (1987), 26(7), 1476-1482. T (K)

(1) CO2 (1) MeOH (2) CO2 (2) MeOH

400

0 100

200 300 P (bar)

1-Amino-2,3-dimethylanthraquinone (C16H13NO2; MW=251.28) y x 10

54.3 53.4 63.7 69.8 74.0 80.2 88.2 99.9 100.7 41.7 56.1 72.7 84.6 100.5 109.9 119.4 132.6 140.6 39.8 50.1 72.0 92.7 108.6 134.5 147.4 162.3 185.8

300

6

S (g/L) 0.24 0.25 0.31 0.35 0.38 0.42 0.47 0.54 0.55 0.16 0.24 0.33 0.40 0.49 0.55 0.61 0.69 0.74 0.12 0.19 0.30 0.41 0.50 0.64 0.72 0.81 0.94

[A-28]

6

y x 10

T (K) P (bar) 308 122 152 182 213 243 274 304 334 355 318 122 152 182 213 243 274 304 334 355 328 122 152 182 213 243 274 304 334 355

1)

400

308 K 318 K 328 K 338 K 348 K

200

100

0 100

CAT4240—CHAPTER 1—31/10/2006—18:15—MUGUNTHAN—XML MODEL C – pp. 19–73

200

300 P (bar)

400

36

Solubility in Supercritical Carbon Dioxide

338

348

122 152 182 213 243 274 304 334 355 122 152 182 213 243 274 304 334 355

0.08 0.17 0.29 0.43 0.58 0.68 0.88 1.01 1.10 0.08 0.13 0.26 0.43 0.60 0.75 1.03 1.24 1.42

34.9 52.4 77.1 105.1 134.2 151.0 189.2 211.5 226.6 42.3 47.7 77.8 114.7 149.1 176.7 233.4 272.1 305.7

1: The mole fraction solubility data were published wrong and thus were recalculated from S in the original article. Source: Shamsipur, M.; Karami, A. R.; Yamini, Y.; Sharghi, H. J. Chem. Eng. Data (2003), 48(1), 71-74.

1-Amino-2,4-dimethylanthraquinone (C16H13NO2; MW=251.28) y1) x 106 2.0 2.6 3.7 5.0 5.7 5.9 6.6 6.5 7.0 2.1 3.8 5.0 6.1 6.7 7.8 9.4 9.7 0.6 3.5 5.4 7.2 8.9 9.7 11.3 12.0

30

20

308 K 328 K 338 K 348 K 358 K

6

S (g/L) 0.009 0.012 0.018 0.025 0.029 0.031 0.035 0.035 0.038 0.008 0.016 0.022 0.028 0.032 0.038 0.047 0.049 0.002 0.013 0.022 0.031 0.040 0.045 0.054 0.058

y x 10

T (K) P (bar) 308 122 152 182 213 243 274 304 334 355 328 152 182 213 243 274 304 334 355 338 152 182 213 243 274 304 334 355

[A-29]

10

0 100

CAT4240—CHAPTER 1—31/10/2006—18:15—MUGUNTHAN—XML MODEL C – pp. 19–73

200

300 P (bar)

400

Solubility Data A

348

358

37

213 243 274 304 334 355 182 213 243 274 304 334 355

0.014 0.041 0.070 0.091 0.109 0.121 0.008 0.029 0.056 0.073 0.093 0.106 0.109

3.7 10.2 16.5 20.6 23.9 26.1 2.4 7.7 13.9 17.2 21.1 23.3 23.5

1: The mole fraction solubility data were published wrong and thus were recalculated from S in the original source. Source: Shamsipur, M.; Karami, A. R.; Yamini, Y.; Sharghi, H. J. Chem. Eng. Data (2003), 48(1), 71-74.

1-Amino-2-ethylanthraquinone (C16H13NO2; MW=251.28)

328

y x 10

0.07 0.10

15.8 21.5

0.12 0.16 0.17 0.19 0.19 0.21 0.21 0.05 0.09 0.12 0.15 0.18 0.19 0.21 0.22 0.23 0.03 0.07 0.11 0.16 0.21 0.25 0.28 0.30 0.31

25.5 31.5 33.5 35.6 36.1 38.2 39.1 12.9 20.3 27.5 32.0 36.3 38.3 40.3 43.1 44.1 8.9 17.9 27.5 37.4 44.8 52.2 57.0 60.3 60.7

90 308 K 318 K 328 K 338 K 348 K

60 6

318

182 213 243 274 304 334 355 122 152 182 213 243 274 304 334 355 122 152 182 213 243 274 304 334 355

S (g/L)

[A-30]

6

y x 10

T (K) P (bar) 308 122 152

1)

30

0 100

200

CAT4240—CHAPTER 1—31/10/2006—18:15—MUGUNTHAN—XML MODEL C – pp. 19–73

300 P (bar)

400

38

Solubility in Supercritical Carbon Dioxide

338

122 0.01 2.6 152 0.05 17.1 182 0.11 29.7 213 0.17 40.7 243 0.22 50.0 274 0.26 57.6 304 0.24 51.0 334 0.21 43.7 355 N/A 43.6 348 122 0.00 1.3 152 0.04 13.5 182 0.10 30.9 213 0.17 44.6 243 0.24 59.9 274 0.29 69.8 304 0.34 77.8 1: The solubility S at 338 K and 355 bar is missing in the source. Source: Shamsipur, M.; Karami, A. R.; Yamini, Y.; Sharghi, H. J. Chem. Eng. Data (2003), 48(1), 71-74.

[A-31]

2-Aminofluorene (C13H11N; MW=181.23) 6

900 318.2 K 328.2 K 343.2 K 6

600 y x 10

y x 10 T (K) P (bar) 318.15 116.0 17 139.5 40 181.0 95 270.0 170 364.0 292 328.15 116.0 15 139.5 47 181.0 94 270.0 319 364.0 507 343.15 116.5 12 140.0 40 181.0 158 272.0 405 364.0 801 Synonym: Fluoren-2-amine Source: Schmitt, W. J.; Reid, R. C. J. Chem. Eng. Data (1986), 31(2), 204212.

300

0 100

CAT4240—CHAPTER 1—31/10/2006—18:15—MUGUNTHAN—XML MODEL C – pp. 19–73

200

300 P (bar)

400

Solubility Data A

39

1-Amino-2-methylanthraquinone (C15H11NO2; MW=237.25)

[A-32]

6

308 K 318 K 328 K 338 K 348 K

y x 10

6

y x 10 T (K) P (bar) S (g/L) 308 122 0.08 19.0 152 0.11 24.5 182 0.14 30.8 213 0.18 38.4 243 0.20 41.7 274 0.22 45.0 304 0.23 46.2 334 0.25 48.1 355 0.28 55.1 318 122 0.05 14.8 152 0.09 23.0 182 0.13 30.6 120 213 0.18 39.9 243 0.22 47.2 274 0.23 49.3 304 0.26 53.8 334 0.28 56.2 80 355 0.30 61.2 328 122 0.02 8.0 152 0.06 17.6 182 0.11 27.6 213 0.16 38.7 40 243 0.22 49.7 274 0.26 58.3 304 0.36 79.3 334 0.41 86.8 355 0.43 90.7 0 338 122 0.01 4.6 100 152 0.04 12.8 182 0.09 24.9 213 0.14 37.4 243 0.20 49.9 274 0.26 60.4 304 0.29 66.8 348 122 0.01 4.8 152 0.04 15.6 182 0.10 30.5 213 0.15 43.3 243 0.21 54.9 274 0.33 83.1 304 0.40 95.2 334 0.44 101.4 355 0.48 109.6 Synonym: C.I. Disperse Orange 11 Source: Shamsipur, M.; Karami, A. R.; Yamini, Y.; Sharghi, H. J. Chem. Eng. Data (2003), 48(1), 71-74.

200

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300 P (bar)

400

40

Solubility in Supercritical Carbon Dioxide

1-((4-Aminophenyl)azo)-2-naphthol (C16H13N3O; MW=263.30)

[A-33]

6

y x 10 T (K) P (bar) 353.15 200 12.8 250 32.4 300 57.6 350 87.8 373.15 200 9.5 250 33.1 300 70.3 350 116.0 Source: Oezcan, A. S.; Clifford, A. A.; Bartle, K. D.; Lewis, D. M. J. Chem. Eng. Data (1997), 42(3), 590-592.

y x 10

6

150 100

353.15 K 373.15 K

50 0 150

250

350

P (bar)

2-Aminopyrazine (C4H5N3; MW=95.10) y x 106

308.15 76.1 126 89.1 870 114.0 1310 139.0 1498 168.6 1763 177.8 1804 Synonym: Pyrazinamine Source: Nakatani, T.; Tohdo, T.; Ohgaki, K.; Katayama, T. J. Chem. Eng. Data (1991), 36(3), 314-316.

[A-34]

2000 6

P (bar)

y x 10

T (K)

1000 0 50

100

150

p-Anisaldehyde (C8H8O2; MW=136.15)

137

200 300 700 2000 5500 8400 11900 400 600 2000 4400 8200

15000

6

y x 10

[A-35]

6

y x 10

T (K) P (bar) 323 55 72 80 90 100 106 115 373 55 69 90 104 125

1)

200

P (bar)

323 K 373 K

10000

5000

0 50

14000

1: The value of y at 323 K and 115 bar was mistyped in the source table (y x 106 = 3000) and thus was corrected based on the distribution coefficient K (=y/x) values listed in the same table. Synonym: 4-Methoxybenzaldehyde Source: Mukhopadhyay, M.; De, S. K. J. Chem. Eng. Data (1995), 40(4), 909-913.

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100 P (bar)

150

Solubility Data A

41

[A-36]

Aniseed1) Essential Oil W (g/kg CO2)

30000

w2) x 106

303.15

80 11.0 10900 100 27.7 27000 140 14.3 14100 180 18.2 17900 1: The botanical name of aniseed is Pimpinella anusum L. 2: Calculated from W. Source: Rodrigues, V. M.; Rosa, P. T. V.; Marques, M. O. M.; Petenate, A. J.; Meireles, M. A. A. J. Agric. Food Chem. (2003), 51(6), 1518-23.

6

P (bar)

w x 10

T (K)

15000

0 50

100

150

200

P (bar)

p-Anisic acid (C8H8O3; MW=152.15)

[A-37]

6

150

323 K 343 K 373 K

100 y x 10

6

y x 10 T (K) P (bar) 323 55 4.61 71 5.78 80 7.35 100 9.21 110 9.64 343 55 3.57 75 4.58 100 10.20 120 21.02 140 32.00 373 50 2.87 75 3.65 92 5.56 112 22.67 130 59.03 151 137.30 Synonym: 4-Methoxybenzoic acid Source: Mukhopadhyay, M.; De, S. K. J. Chem. Eng. Data (1995), 40(4), 909913.

50

0 40

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80

120 P (bar)

160

42

Solubility in Supercritical Carbon Dioxide

Anisole (C7H8O; MW=108.14) T (K)

P (bar)

[A-38]

6

y x 10 56.9 1800 56.9 1800 61.6 1800 61.6 1800 66.6 2600 66.6 2500 71.6 2800 71.6 3000 71.6 2900 71.6 2600 50000 76.3 4200 76.3 5100 353.1 56.9 5300 40000 56.9 5300 76.3 6700 76.3 6700 30000 95.9 9100 115.6 14700 115.6 14900 20000 135.4 34100 135.4 33400 135.4 34000 10000 393.2 61.6 15700 61.6 16300 76.3 16000 0 76.3 16500 50 76.3 16100 95.9 18100 95.9 17900 115.6 21600 115.6 20600 135.4 27600 135.4 27900 154.9 37700 154.9 38500 164.7 46600 164.7 46600 164.7 46500 Synonyms: Methoxybenzene; Methyl phenyl ether Source: Walther, D.; Maurer, G. J. Chem. Eng. Data (1993), 38, 247-249. 313.2

y x 10

6

313.2 K 353.1 K 393.2 K

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100 P (bar)

150

Solubility Data A

43

Anisole (1) (C7H8O; MW=108.14) + 1-Methylnaphthalene (2) Mixture

372.6

Methanol (wt%)

35.8 75.5 118.5 157.8 193.0 230.2 373.2 34.8 75.5 118.5 157.5 194.7 230.2 1: Cosolvent in CO2.

0 0 0 0 0 0 1.98 0.21 0.39 0.61 1.34 2.38

y1 x 106 1300 1100 1700 2500 3700 5000 18900 34100 30800 28700 27200 23900

y2 x 106 3900 2700 4700 5600 12000 21700 4400 1000 1500 2600 3900 5200

[A-39]

40000

30000 6

P (bar)

y x 10

T (K)

1)

20000 1 (Pure CO2) 1 (w/ MeOH) 2 (Pure CO2) 2 (w/ MeOH)

10000

0 0

Synonym of (1): Methoxybenzene Source: Reilly, J.; Kim, C.; Clark, A.; Donohue, M. Fluid Phase Equil. (1992), 73(1-2), 81-107.

100 P (bar)

[A-40]

Anthracene (C14H10; MW=178.23) 6

y x 10

200

150

313 K 323 K 333 K

6

27 30 35 38 41 43 45 48 50 52 54 57 58 61 63 65 66 68 70 71 73 75 77 72 82 84 87

y x 10

T (K) P (bar) 313 118.1 124.3 131.5 138.0 144.9 152.0 158.5 165.8 172.9 179.1 186.0 192.9 199.8 206.7 213.9 221.5 227.4 234.3 241.2 248.0 254.9 261.8 268.7 279.0 289.6 300.1 310.3

200

100

50

0 100

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200

300 P (bar)

44

Solubility in Supercritical Carbon Dioxide

320.5 327.8 337.4 323 121.8 125.3 129.3 134.4 140.0 146.8 154.3 162.0 172.6 183.1 193.2 203.5 213.0 223.9 234.0 245.0 255.1 265.5 276.6 285.7 292.8 300.1 306.3 306.6 314.9 323.8 334.5 344.1 350.0 333 132.2 138.4 145.2 151.7 159.2 165.6 171.8 179.9 185.7 193.1 199.9 206.9 214.3 220.3 227.4 234.1 240.8 248.3 254.7

89 90 92 22 25 31 35 42 48 54 60 67 75 81 87 93 97 102 107 111 116 121 124 126 128 130 131 133 136 139 142 145 22 30 43 57 68 78 85 92 97 103 107 112 117 121 124 128 132 135 139

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Solubility Data A

45

262.4 143 270.5 147 279.6 152 289.7 156 300.3 160 310.3 165 320.9 170 329.0 173 336.6 177 346.6 180 355.9 183 Source: Anitescu, G.; Tavlarides, L. L. J. Supercrit. Fluids (1997), 10(3), 175-189.

Anthracene (C14H10; MW=178.23) T (K)

P (bar)

[A-41]

6

y x 10

6

y x 10

100 42.6 134 55.8 168 66.4 202 73.5 236 82.8 270 91.9 304 97.2 338 104.0 Source: Ashraf-Khorassani, M.; Combs, M. T.; Taylor, L. T.; Schweighardt, F. K.; Mathias, P. S. J. Chem. Eng. Data (1997), 42(3), 636-640.

140

313.15

70

0 0

100

200 P (bar)

Anthracene (C14H10; MW=178.23)

400

[A-42]

6

T (K) P (bar) y x 10 91 308.2 4 111 7 139 27 191 46 238 63 284 71 1: Calculated from temperature and density in the source graph. 2: Obtained by digitizing the graph in the original article. The data may have a large reading error as the original graph is small. Source: Burk, R.; Kruus, P. Can. J. Chem. Eng. (1992), 70(2), 1403-1407.

80

6

2)

y x 10

1)

300

40

0 50

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150 P (bar)

250

46

Solubility in Supercritical Carbon Dioxide

Anthracene (C14H10; MW=178.23)

[A-43]

6

160

y x 10

6

y x 10 T (K) P (bar) 323.15 92.6 3.1 103.0 3.3 124.8 32.5 133.4 46.7 140.3 55.0 143.3 54.5 161.2 81.2 173.5 92.6 176.5 98.8 199.4 109.0 206.1 110.4 239.6 125.4 256.3 133.6 264.4 135.2 292.6 146.7 Source: Coutsikos, P.; Magoulas, K.; Tassios, D. J. Chem. Eng. Data (1995), 40(4), 953-958.

80

0 50

150

250

Anthracene (C14H10; MW=178.23) T (K) 323.15

(bar)

y2)

x

[A-44]

106

88 6 100 30 161 60 212 95 260 130 316 150 357 180 1: Calculated from temperature and density in the source graph. 2: Obtained by digitizing the graph in the original article. Source: Ekart, M. P.; Bennett, K. L.; Ekart, S. M.; Gurdial, G. S.; Liotta, C. L.; Eckert, C. A. AIChE J. (1993), 39(2), 235-248.

200 y x 106

P1)

100

0 50

Anthracene (C14H10; MW=178.23) T (K) 313

P (bar) 80 135 210 280 340 410 470

3

M x 10 (mol/L) 0.051 0.914 1.500 1.810 2.030 2.210 2.310

350

P (bar)

y x 106 8.1 53.3 77.7 88.5 96.0 101.0 103.0

CAT4240—CHAPTER 1—31/10/2006—18:15—MUGUNTHAN—XML MODEL C – pp. 19–73

150

250

350

P (bar)

[A-45]

Solubility Data A

47

323

313 K 323 K 333 K

6

200 y x 10

83.4 0.029 5.3 115 0.471 37.7 175 1.420 83.3 245 2.220 118.0 310 2.640 122.0 380 2.970 143.0 445 3.200 149.0 470 3.250 150.0 333 83.4 0.016 3.3 88.3 0.035 6.8 145 0.842 63.3 210 2.200 131.0 280 3.030 163.0 345 3.730 191.0 415 4.200 205.0 470 4.760 227.0 Source: Hampson, J. W. J. Chem. Eng. Data (1996), 41(1), 97-100.

100

0 0

200 P (bar)

400

Anthracene (C14H10; MW=178.23)

[A-46]

6

6

100 y x 10

y x 10 T (K) P (bar) 308.2 102 13.1 121 37.7 141 53.5 161 72.1 181 83.8 Source: Goodarznia, I.; Esmaeilzadeh, F. J. Chem. Eng. Data (2002), 47(2), 333-338.

50 0 100

150

200

P (bar)

Anthracene (C14H10; MW=178.23)

323.15

104.3 138.8 276.7 414.5 90.6 104.4 118.1 138.8 173.3 207.7 276.7 345.6 380.1 414.5

y x 106 29.2 51.5 69.4 79.5 3.5 4.0 16.1 49.6 89.3 109.0 140.0 154.0 161.0 172.0

400 303.15 K 323.15 K 343.15 K

300 6

303.15

P (bar)

y x 10

T (K)

[A-47]

200

100

0 50

150

250 P (bar)

CAT4240—CHAPTER 1—31/10/2006—18:15—MUGUNTHAN—XML MODEL C – pp. 19–73

350

450

48

Solubility in Supercritical Carbon Dioxide

343.15

118.1 14.2 129.2 22.2 138.8 35.8 152.6 63.0 173.3 70.6 207.7 168.0 276.7 248.0 345.6 309.0 414.5 349.0 Source: Johnston, K. P.; Ziger, D. H.; Eckert, C. A. Ind. Eng. Chem. Fund. (1982), 21(3), 191-197.

Anthracene (C14H10; MW=178.23)

318

104.2 138.7 172.4 206.7 276.7 104.2 138.7 172.4 206.7 242.0 276.7

y x 106 16.8 50.8 80.1 91.4 92.3 8.9 55.6 89.0 101.0 109.0 112.0

120

6

308

P (bar)

y x 10

T (K)

[A-48]

80

40

308 K 318 K

0 100

Source: Kosal, E.; Holder, G. D. J. Chem. Eng. Data (1987), 32(2), 148-150.

200 P (bar)

Anthracene (C14H10; MW=178.23)

[A-49]

6

80 y x 10

y x 106 T (K) P (bar) 100 313.1 30.1 110 31.2 125 37.6 135 39.6 150 41.8 175 48.7 58.9 200 Source: Kwiatkowski, J.; Lisicki, Z.; Majewski, W. Ber. Bunsenges. Phys. Chem. (1984), 88(9), 865-869.

300

40 0 50

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150 P (bar)

250

Solubility Data A

49

Anthracene (C14H10; MW=178.23)

[A-50]

y x 106

120

80

6

41.6 50.8 69.6 75.9 78.3 20.5 53.9 74.5 85.1 94.0 13.8 57.3 80.7 102.0 113.0

y x 10

T (K) P (bar) 308.1 100 150 200 250 300 318.1 100 150 200 250 300 328.1 100 150 200 250 300

40

308.1 K 318.1 K 328.1 K

0 50

150

250

350

P (bar)

Source: Li, Q.; Zhang, Z.; Zhong, C.; Liu, Y.; Zhou, Q. Fluid Phase Equil. (2003), 207(1-2), 183-192.

Anthracene (C14H10; MW=178.23)

[A-51]

106

1500

313.15 K 323.15 K 333.15 K 343.15 K 373.15 K 423.15 K

1000

y x 106

yx T (K) P (bar) 313.15 80 2.4 100 15.4 150 49.8 200 59.2 300 82.3 350 85.3 323.15 80 1.7 100 4.5 150 46.2 200 74.3 300 116.0 350 133.0 333.15 100 2.5 200 91.9 300 159.0 343.15 200 106.0 300 212.0 373.15 100 7.3 150 39.7 200 134.0 300 432.0 350 576.0 423.15 100 71.6 200 403.0 300 1260.0 Source: Lou, X.; Janssen, H.-G.; Cramers, C. A. J. Chromatogr. A (1997),785 (1-2), 57-64.

500

0 0

100

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200 P (bar)

300

400

50

Solubility in Supercritical Carbon Dioxide

[A-52]

Anthracene (C14H10; MW=178.23) 106

8000

6000 y x 106

yx T (K) P (bar) 323.15 150 26 200 31 250 69 300 107 350 132 400 145 348.15 200 66 250 155 300 247 350 311 400 374 373.15 150 26 200 70 250 224 300 375 350 486 400 653 398.15 150 285 200 176 250 404 300 752 350 1090 400 1330 423.15 150 139 200 376 250 834 300 1450 350 2010 400 2280 448.15 150 313 200 572 250 1210 300 1910 350 2750 400 3450 473.15 150 705 200 1680 250 2960 300 4340 350 5840 400 7280 Source: Miller, D. J.; Hawthorne, S. B. Anal. Chem. (1995), 67(2), 273-279.

4000

323.15 K 348.15 K 373.15 K 398.15 K 423.15 K 448.15 K 473.15 K

2000

0 100

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200

300 P (bar)

400

Solubility Data A

51

[A-53]

Anthracene (C14H10; MW=178.23) 106

y x 106

yx T (K) P (bar) 313 70.8 0.49 100 75.3 0.87 81.6 1.66 82.6 1.96 85.4 4.20 50 87.4 7.39 88.2 7.06 92.0 8.72 106.9 26.70 0 111.1 26.50 50 124.6 48.60 144.1 53.60 167.0 65.10 208.8 89.80 Source: Ngo, T. T.; Bush, D.; Eckert, C. A.; Liotta, C. L. AIChE J. (2001), 47(11), 2566-2572.

Anthracene (C14H10; MW=178.23) T (K) 293.15

298.15

303.15

308.15

313.15

P (bar) 69.5 122.0 158.0 334.0 500.0 93.9 152.0 196.4 378.6 119.7 180.4 237.5 422.2 605.0 144.3 212.4 268.3 471.7 80.4 100.0 168.4 249.0 298.8 513.1 726.8

M x 106 (mol/L) 203 326 343 392 611 255 421 433 463 377 538 578 597 991 458 697 724 776 26 249 609 889 918 1050 1430

150

250

P (bar)

[A-54]

y1) x 106 11.1 16.3 16.6 17.3 25.6 13.9 21.1 20.9 20.4 20.5 27.0 27.8 26.4 41.6 24.9 35.0 34.9 34.2 4.0 17.3 33.2 44.4 44.4 46.4 59.8

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52

323.15

325.65 328.15

330.65 333.15

338.15

340.65 343.15

345.65 348.15

353.15

84.4 194.6 273.4 564.4 89.0 143.9 215.0 380.0 620.0 836.3 319.6 394.0 94.7 244.7 335.0 412.0 890.9 350.6 99.8 168.8 275.1 363.2 450.0 701.4 946.8 106.5 180.3 294.7 397.4 483.8 748.3 999.1 413.1 113.7 194.8 318.2 431.2 517.8 789.0 1053.2 444.6 118.4 216.7 344.6 460.4 555.5 839.5 1105.4 124.0 232.3 372.1

52 767 1140 1310 59 406 983 1720 1990 2220 1770 1830 74 1230 1840 2030 2670 2100 97 617 1530 2350 2540 2780 3210 112 788 1910 2830 3090 3480 3900 3110 133 977 2390 3500 3750 4180 4750 3880 164 1230 2950 4170 4570 4970 5710 223 1540 3580

8.2 41.7 57.3 57.8 9.3 26.0 53.9 82.7 87.5 92.9 89.1 88.1 11.3 67.0 92.6 97.8 111.7 105.7 14.6 40.9 83.0 118.6 122.2 122.6 134.2 16.3 53.0 104.2 142.5 148.8 153.4 163.1 156.6 18.6 66.1 130.7 176.0 180.7 184.5 198.6 195.4 23.0 81.7 161.2 210.0 219.9 219.1 238.7 31.1 102.5 195.3

493.2

4970

250.1

313 K 323 K 333 K 343 K 353 K 363 K

400

300 y x 106

318.15

Solubility in Supercritical Carbon Dioxide

200

100

0 0

CAT4240—CHAPTER 1—31/10/2006—18:15—MUGUNTHAN—XML MODEL C – pp. 19–73

500 P (bar)

1000

Solubility Data A

358.15

363.15

53

586.3

5590

269.5

887.3

5940

261.7

1156.5

6770

283.1

129.0

289

40.3

247.3

1840

122.8

394.3

4360

238.5

524.1

6210

312.6

627.2

6640

319.5

930.3

7120

313.8

132.6

344

48.8

267.0

2370

157.1

416.7

5440

298.3

557.9

7360

370.1

666.7

7890

379.0

975.7 8410 370.6 137.0 444 63.2 272.2 2950 200.1 444.0 6840 374.4 588.4 8830 444.1 1020.5 9930 437.6 1: Calculated from M. Source: Zerda, T. W.; Wiegand, B.; Jonas, J. J. Chem. Eng. Data (1986), 31(3), 274-277. 368.15

Anthracene (C14H10; MW=178.23) T (K) 313

P (bar) 108 115 120 131 145 153 161 171 180 190 200 210 219 231 239 250

[A-55]

Ethane1) (mol%)

y x 106

5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5

24 27 32 37 43 47 50 53 58 62 66 70 73 77 80 84

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54

Solubility in Supercritical Carbon Dioxide

333

5 5 5 5 5 5 5 5 5 5 5 5 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 5 5 5 5 5 5 5 5 5

87 91 94 96 98 101 103 105 107 110 112 115 26 31 35 38 47 50 54 60 63 68 72 76 80 85 90 94 98 103 107 110 114 112 120 123 126 128 130 133 7 16 28 50 69 81 87 97 106

250 313 K, 5% C2H6 313 K, 10% C2H6 333 K, 5% C2H6 333 K, 10% C2H6

200

y x 106

313

261 270 280 287 295 302 310 317 325 334 342 350 107 114 121 129 143 152 160 172 179 190 200 207 217 227 238 248 258 269 279 289 300 307 316 325 333 338 346 350 110 121 130 144 155 165 172 181 191

150 100 50 0 0

100

CAT4240—CHAPTER 1—31/10/2006—18:15—MUGUNTHAN—XML MODEL C – pp. 19–73

200 P (bar)

300

400

Solubility Data A

200 5 113 210 5 120 217 5 125 226 5 132 235 5 138 242 5 143 251 5 149 260 5 155 268 5 160 275 5 164 285 5 168 294 5 174 302 5 177 310 5 181 317 5 185 325 5 188 335 5 193 343 5 196 350 5 199 333 120 10 19 125 10 28 131 10 37 137 10 45 145 10 60 154 10 74 160 10 83 172 10 97 179 10 103 186 10 109 194 10 117 208 10 127 217 10 134 227 10 142 232 10 148 249 10 157 258 10 163 273 10 173 282 10 179 294 10 186 304 10 192 309 10 194 312 10 196 318 10 198 323 10 202 335 10 208 345 10 212 350 10 215 1: Cosolvent in CO2. Source : Anitescu, G.; Tavlarides, L. L. J. Supercrit. Fluids (1997),11(1,2), 37-51.

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55

56

Solubility in Supercritical Carbon Dioxide

Anthracene (C14H10; MW=178.23) T (K) 313

313

P (bar) 120 125 132 138 146 155 166 176 187 197 206 217 227 236 248 261 268 289 293 300 300 310 317 328 338 345 350 366 107 112 118 124 131 138 145 152 159 165 176 186 197 207

Propane1) (mol%) 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 10 10 10 10 10 10 10 10 10 10 10 10 10 10

[A-56] y x 106 33 36 38 42 45 49 54 59 63 67 71 75 78 83 87 92 95 102 103 106 105 109 112 115 118 121 123 125 33 37 43 47 52 57 61 65 70 73 81 86 93 98

CAT4240—CHAPTER 1—31/10/2006—18:15—MUGUNTHAN—XML MODEL C – pp. 19–73

Solubility Data A

333

333

10 10 10 10 10 10 10 10 10 10 10 10 10 10 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 10 10 10 10 10

104 108 114 118 123 127 132 136 140 144 148 151 154 157 13 19 24 34 54 59 71 83 93 99 107 113 119 125 130 136 140 145 150 154 158 162 166 170 175 180 189 194 199 213 15 17 33 37 42

250

313 K, 5% C3H8 313 K, 10% C3H8 333 K, 5% C3H8 333 K, 10% C3H8

200

y x 106

217 227 238 249 259 269 279 290 300 311 321 331 340 351 116 121 127 135 143 147 152 159 165 171 179 185 193 200 207 214 221 228 235 241 248 255 262 268 276 284 300 310 320 350 116 118 121 124 127

57

150 100 50 0 0

100

CAT4240—CHAPTER 1—31/10/2006—18:15—MUGUNTHAN—XML MODEL C – pp. 19–73

200 P (bar)

300

400

58

Solubility in Supercritical Carbon Dioxide

131 135 139 144 149 159 167 176 187 197 207 217 228 238 248 259 269 280 290 300 310 320 330 339 350

50 58 67 77 87 103 113 125 136 146 155 163 173 180 187 194 199 206 211 215 221 227 233 238 242

10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10

1: Cosolvent in CO2. Source: Anitescu, G. ; Tavlarides, L. L. J. Supercrit. Fluids (1997),11(1,2), 37-51.

Anthracene (C14H10; MW=178.23) T (K) 313

P (bar) 115 122 129 138 146 155 166 176 186 197 207 215

[A-57]

Butane1) (mol%)

y x 106

5 5 5 5 5 5 5 5 5 5 5 5

33 36 38 44 47 52 57 62 66 70 74 78

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Solubility Data A

333

125 131 138 145 152 159 165 172 179 186 193 207 221 234 248 262 276 289 301 312 328 340 350 110 116 121 128 135 143 152 164 174 185

5 5 5 5 5 5 5 5 5 5 5 5 5 5 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 5 5 5 5 5 5 5 5 5 5

83 88 94 97 99 105 108 112 115 117 121 123 126 129 39 43 49 56 59 65 70 75 79 83 87 92 96 102 109 117 124 132 137 143 148 152 156 162 166 169 12 16 21 30 43 63 78 98 110 123

300

313 K, 5% C4H10 313 K, 10% C4H10 333 K, 5% C4H10 333 K, 10% C4H10

200 y x 106

313

228 242 255 262 269 283 290 300 308 316 325 334 342 350 105 110 117

59

100

0 0

100

CAT4240—CHAPTER 1—31/10/2006—18:15—MUGUNTHAN—XML MODEL C – pp. 19–73

200 P (bar)

300

400

60

Solubility in Supercritical Carbon Dioxide

197 5 134 211 5 147 221 5 155 230 5 161 241 5 168 333 252 5 176 263 5 183 272 5 188 283 5 196 292 5 200 300 5 204 310 5 208 322 5 213 332 5 217 341 5 221 350 5 223 333 115 10 34 121 10 45 128 10 60 135 10 73 141 10 85 148 10 100 156 10 112 165 10 125 176 10 138 186 10 149 197 10 160 207 10 172 217 10 180 228 10 190 240 10 199 252 10 208 262 10 213 271 10 221 283 10 231 293 10 239 303 10 243 315 10 254 325 10 259 333 10 263 341 10 266 350 10 270 1: Cosolvent in CO2. Source: Anitescu, G. ; Tavlarides, L. L. J. Supercrit. Fluids (1997),11(1,2), 37-51.

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Solubility Data A

61

[A-58]

Anthracene (C14H10; MW=178.23)

313

333

333

P (bar) 138 152 166 179 193 210 222 235 249 264 280 295 307 137 150 168 179 191 203 219 235 249 265 278 291 300 139 151 161 174 190 206 224 232 241 258 277 294 307

(mol%)

5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 10 10 10 10 10 10 10 10 10 10 10 10 10

y x 106 70 83 91 97 104 109 113 119 123 127 132 135 138 47 69 100 118 140 156 175 192 205 220 230 238 244 144 160 177 197 215 232 253 261 269 283 295 304 310

400

300 y x 106

T (K)

Methanol1)

313 K, 5% MeOH 333 K, 5% MeOH 333 K, 10% MeOH

200

100

0 100

1: Cosolvent in CO2. Source: Anitescu, G.; Tavlarides, L. L. J. Supercrit. Fluids (1997),11(1,2), 37-51.

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200 P (bar)

300

62

Solubility in Supercritical Carbon Dioxide

[A-59]

Anthracene (C14H10; MW=178.23) T (K)

P (bar)

Methanol1) (mol%)

y x 106

Pure CO2 MeOH

308.15

y x 106

120 0.0 50 150 0.0 61 200 0.0 70 200 0.0 69 300 0.0 78 350 0.0 80 120 3.5 69 120 3.5 64 200 3.5 87 300 3.5 95 350 3.5 104 1: Cosolvent in CO2. Source: Dobbs, J. M.; Johnston, K. P. Ind. Eng. Chem. Res. (1987), 26(7), 1476-1482.

120

80

40 0

100

200

300

P (bar)

[A-60]

Anthracene (C14H10; MW=178.23)

318.1

328.1

308.1

318.1

100 150 200 250 300 100 150 200 250 300 100 150 200 250 300 100 150 200 250 300 100 150 200 250 300

Cosolvent1) (mol%) Acetone 4.0 4.0 4.0 4.0 4.0 4.0 4.0 4.0 4.0 4.0 4.0 4.0 4.0 4.0 4.0 Ethanol 4.0 4.0 4.0 4.0 4.0 4.0 4.0 4.0 4.0 4.0

140

y x 106 66.6 76.8 85.9 91.6 95.6 55.7 93.9 103.0 112.0 119.0 36.8 86.8 106.0 128.0 135.0 85.1 99.2 109.0 116.0 125.0 77.8 99.3 115.0 127.0 137.0

100 y x 106

308.1

P (bar)

Acetone

60

308.1 K 318.1 K 328.1 K

20 50

150

250

350

P (bar) 160

y x 106

T (K)

400

120 Ethanol

80

308.1 K 318.1 K 328.1 K

40 50

150

250 P (bar)

CAT4240—CHAPTER 1—31/10/2006—18:15—MUGUNTHAN—XML MODEL C – pp. 19–73

350

Solubility Data A

63

100 4.0 52.2 150 4.0 98.8 200 4.0 127.0 250 4.0 144.0 300 4.0 154.0 200 Cyclohexane 308.1 100 4.0 92.2 150 4.0 111.0 200 4.0 130.0 150 250 4.0 142.0 300 4.0 151.0 318.1 100 4.0 75.4 150 4.0 109.0 100 200 4.0 133.0 250 4.0 150.0 300 4.0 158.0 50 328.1 100 4.0 56.0 150 4.0 111.0 50 200 4.0 143.0 250 4.0 164.0 300 4.0 178.0 1: Cosolvent in CO2. Source: Li, Q.; Zhang, Z.; Zhong, C.; Liu, Y.; Zhou, Q. Fluid Phase Equil. (2003), 207(1-2), 183-192.

y x 106

328.1

Cyclohexane 308.1 K 318.1 K 328.1 K

150

250

[A-61]

Anthracene (1) + Carbazole (2) Mixture 313.1

P (bar) 100 125 150 175 200

y2 x 106

42.6 51.5 64.4 69.5 75.4

16.0 16.2 18.0 18.8 24.0

100 y x 106

T (K)

y1 x 106

Anth Carb

50 0

Source: Kwiatkowski, J.; Lisicki, Z.; Majewski, W. Ber. Bunsenges. Phys. Chem. (1984), 88(9), 865-869.

50

150

313.1

P (bar) 100 125 150 175 200

y1 x

33.8 48.5 66.4 64.2 70.2

y2 x

106 505 749 939 1090 1180

Source: Kwiatkowski, J.; Lisicki, Z.; Majewski, W. Ber. Bunsenges. Phys. Chem. (1984), 88(9), 865-869.

[A-62] 1500

y x 106

T (K)

250

P (bar)

Anthracene (1) + Phenanthrene (2) Mixture 106

350

P (bar)

750

Anth Phen

0 50

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150 P (bar)

250

64

Solubility in Supercritical Carbon Dioxide

[A-63]

Anthracene (1) + Phenanthrene (2) + Carbazole (3) Mixture1) T (K)

P (bar)

y1 x 106

y2 x 106

y3 x 106

1000

y x 106

111 35.53 775.7 12.22 131 65.34 882.8 21.02 161 74.95 1167.4 23.08 181 110.9 1196.1 28.25 201 116.5 1437.7 28.52 1: The initial composition of 1, 2 and 3 in the solute mixture was 40:40:20(%). Source: Goodarznia, I.; Esmaeilzadeh, F. J. Chem. Eng. Data (2002), 47(2), 333-338.

1500

308.2

Anth Phen Carb

500

0

100

150

200

P (bar)

9,10-Anthraquinone (C14H8O2; MW=208.22) 2000 308.2 K 318.2 K 333.2 K

y x 106

y x 106 T (K) P (bar) 308.2 152 482 203 590 253 664 318.2 152 681 203 917 253 1080 333.2 152 771 203 1420 253 1790 Synonyms: Anthraquinone; 9,10-Anthracenedione Source: Mishima, K.; Matsuyama, K.; Ishikawa, H.; Hayashi, K-I.; Maeda, S. Fluid Phase Equil. (2002), 194-197, 895-904. Special Note: These data do not agree with the subsequent table.

[A-64]

1000

0 130

9,10-Anthraquinone (C14H8O2; MW=208.22) T (K) P (bar) 308.15 84.1 95.6 116.4 158.8 199.1 239.2 260.3 298.2

y x 106 1.88 4.71 10.36 27.71 34.07 40.83 44.55 51.39

CAT4240—CHAPTER 1—31/10/2006—18:15—MUGUNTHAN—XML MODEL C – pp. 19–73

170

210

250

P (bar)

[A-65]

Solubility Data A

65

90 308.15 K 318.15 K

318.15

89.6 0.88 107.7 3.53 125.6 10.32 141.4 16.48 187.1 39.03 219.5 50.96 233.9 56.13 262.1 59.38 306.3 73.99 Synonyms: Anthraquinone; 9,10-Anthracenedione Source: Coutsikos, P.; Magoulas, K.; Tassios, D. J. Chem. Eng. Data (1997), 42(3), 463-466.

y x 106

60

30

0 50

150

250

Arachidonic acid ethyl ester (C22H36O2; MW = 332.52)

[A-66]

8000 y x 106

T (K) P (bar) y1) x 106 313 89.0 380 98.9 1900 119.6 3300 139.5 6000 159.4 7500 1: Obtained by digitizing the graph in the original article. Synonyms: Ethyl arachidonate; (all -Z )5,8,11,14-Eicosatetraenoic acid ethyl ester Source: Liong, K.; Foster, N.; Ting, S. Ind. Eng. Chem. Res. (1992), 31(1), 400-404.

4000

0 50

100

150

200

P (bar)

Arachidyl alcohol (C20H42O; MW=298.55)

[A-67] 300 y x 106

y x 106 T (K) P (bar) 308.15 89 70.5 98 97.9 118 152.0 148 198.0 178 221.0 207 246.0 237 257.0 Synonym: 1-Eicosanol Source: Iwai, Y.; Koga, Y.; Maruyama, H.; Arai, Y. J. Chem. Eng. Data (1993), 38(4), 506-508.

350

P (bar)

150

0 0

100

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200 P (bar)

300

66

Solubility in Supercritical Carbon Dioxide

Aroclor 12541)

[A-68] 106

yx T (K) P (bar) 313 101 5900 323 114 7500 1: The average molecular weight of the Aroclor 1254 mixture is 326.5. Synonym: PCB1254 Source: Dooley, K. M.; Ghonasgi, D.; Knopf, F. C.; Gambrell, R. P. Environ. Progr. (1990), 9(4), 197-203.

Artemisinin (C15H22O5; MW=282.33) y x 106 663 903 1139 1346 1629 1734 1864 1982 2125 342 768 1060 1337 1587 1799 1983 2120 2226 99 502 810 1242 1591 1893 2169 2375 2519 98 307 642 990

3000 310.1 K 318.1 K 328.1 K 338.1 K

2000 y x 106

T (K) P (bar) 310.1 100 120 140 160 180 200 220 240 270 318.1 100 120 140 160 180 200 220 240 260 328.1 100 120 140 160 180 200 220 240 260 338.1 101 120 140 160

[A-69]

1000

0 50

CAT4240—CHAPTER 1—31/10/2006—18:15—MUGUNTHAN—XML MODEL C – pp. 19–73

150 P (bar)

250

Solubility Data A

180 200 220 240 260

67

1437 1868 2238 2501 2659

Synonym: (3R,5aS,6R,8aS,9R,12S,12aR)Octahydro-3,6,9-trimethyl-3,12-epoxy-12Hpyrano[4,3-j]-1,2-benzodioxepin-10(3H)-one Source: Xing, H.; Yang, Y.; Su, B.; Huang, M.; Ren, Q. J. Chem. Eng. Data (2003), 48(2), 330-332.

Ascorbic acid (C6H8O6; MW=176.12) 40 y x 106

y x 106 T (K) P (bar) 313.1 130 18.5 150 23.9 170 28.0 200 31.9 Synonym: Vitamin C Source: Cortesi, A.; Kikic, I.; Alessi, P.; Turtoi, G.; Garnier, S. J. Supercrit. Fluids (1999), 14(2), 139-144.

[A-70]

20 0 100

150 P (bar)

Ascorbyl palmitate (C22H38O7; MW=414.53)

[A-71]

106

8 y x 106

yx T (K) P (bar) 308.1 130 2.10 150 2.86 170 3.94 200 5.15 313.1 130 1.57 150 2.88 170 4.24 200 5.81 Synonyms: Ascorbic acid 6-palmitate; L-Ascorbic acid 6-hexadecanoate

200

4

308.1 K 313.1 K

0 100

Source: Cortesi, A.; Kikic, I.; Alessi, P.; Turtoi, G.;

Garnier, S. J. Supercrit. Fluids(1999), 14(2), 139-144.

CAT4240—CHAPTER 1—31/10/2006—18:15—MUGUNTHAN—XML MODEL C – pp. 19–73

150 P (bar)

200

68

Solubility in Supercritical Carbon Dioxide

Aspirin (C9H8O4; MW=180.16)

[A-72]

106

w x 106

wx T (K) P (bar) 300 318 60 1.2 83 6.3 103 37.1 150 121 94.0 138 141.0 172 236.0 0 221 241.0 50 228 260.0 Synonyms: 2-Acetoxybenzoic acid; Acetylsalicylic acid Source: Tavana, A.; Randolph, A. D. AIChE Symp. Ser. (1991), 87 (284, Part. Des. Cryst.), 5-15.

150 P (bar)

Aspirin (C9H8O4; MW=180.16)

308.15

318.15

328.15

318.15

120 150 172 185 200 215 230 250 120 150 172 185 200 215 230 250 120 150 172 185 200 215 230 250 100 120 150 172 200

(mol%) 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 3.0 3.0 3.0 3.0 3.0

y x 106 89 112 122 129 133 142 145 151 72 139 175 195 212 228 234 258 63 137 182 234 277 286 303 347 218 337 428 525 615

900

CO2, 308 K CO2, 318 K CO2, 328 K Acet, 318 K Acet, 328 K

600

yx

P (bar)

[A-73]

106

T (K)

Acetone1)

250

300

0 50

CAT4240—CHAPTER 1—31/10/2006—18:15—MUGUNTHAN—XML MODEL C – pp. 19–73

150 P (bar)

250

Solubility Data A

69

3.0 100 113 3.0 120 321 3.0 150 498 3.0 172 612 200 757 3.0 1: Cosolvent in CO2. Synonyms: 2-Acetoxybenzoic acid; Acetylsalicylic acid Source: Huang, Z.; Lu, W. D.; Kawi, S.; Chiew, Y. C. J. Chem. Eng. Data (2004), 49(5), 1323-1327. 328.15

Aspirin (1) + Salicylic acid (2) Mixture T (K)

P (bar)

y1 x 106

[A-74]

y2 x 106

y x 106

83 121 269 103 210 389 121 250 440 138 284 480 172 272 438 207 314 508 231 275 479 245 318 495 Source: Tavana, A.; Randolph, A. D. AIChE Symp. Ser. (1991), 87 (284, Part. Des. Cryst.), 5-15.

600

318

300 Aspirin Salicylic acid

0 50

150

250

P (bar)

Atratone (C9H17N5O; MW=211.26)

[A-75]

y x 106

T (K) P1) (bar) S1,2) (g/L) y3) x 106 4000 313.15 80 0.01 8 85 0.15 86 90 0.40 168 95 1.36 483 2000 100 1.85 608 110 3.16 958 120 3.98 1150 0 150 7.00 1860 180 10.00 2530 50 210 13.00 3170 1: Obtained by digitizing the original graph in the original article. 2: The data may have a large reading error as the source graph is small. 3: Calculated from S. Synonym: 2-Ethylamino-4-isopropylamino-6-methoxy-s-triazine Source: Rodrigues, S. V.; Nepomuceno, D.; Martins, L. V.; Baumann, W. -61.Fresenius' J. Anal. Chem. (1998), 360(1), 58-61.

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150 P (bar)

250

70

Solubility in Supercritical Carbon Dioxide

Atrazine (C8H14ClN5; MW=215.68) P1)

T (K) 313.15

(bar)

S1,2)

(g/L)

y3)

x

[A-76]

106

140

y x 106

80 0.003 2.1 85 0.010 5.6 90 0.031 12.7 70 100 0.084 27.0 120 0.156 44.3 150 0.272 71.0 0 180 0.369 91.6 50 210 0.479 115.0 1: Obtained by digitizing the original graph in the original article. 2: The data may have a large reading error as the source graph is small. 3: Calculated from S. Synonym: 2-Chloro-4-ethylamino-6-isopropylamino-s-triazine Source: Rodrigues, S. V.; Nepomuceno, D.; Martins, L.V.; Baumann, W. Fresenius' J. Anal. Chem. (1998), 360(1), 58-61.

150

250

P (bar)

Atrazine (C8H14ClN5; MW=215.68) T (K) P (bar)

[A-77]

y x 106

313

313 K 373 K 413 K

y x 106

150 14 6000 200 23 250 55 300 78 350 104 4000 400 122 450 141 373 150 12 200 101 250 202 2000 300 426 350 661 400 976 450 1340 413 150 57 0 200 267 0 250 750 300 1920 350 3450 400 4920 Synonym: 2-Chloro-4-ethylamino-6isopropylamino-s-triazine Source: Miller, D. J.; Hawthrone, S. B.; Clifford, A. A. J. Supercrit. Fluids(1997), 10(1), 57-63.

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200

400 P (bar)

600

Solubility Data A

71

Atrazine (C8H14ClN5 ; MW=215.68) y1)

[A-78]

106

313.15 K 333.15 K 353.15 K

y x 10

6

x T (K) P (bar) 313.15 113.3 24 116.8 30 130.1 33 136.0 39 144.1 27 159.2 41 174.2 49 180.1 68 193.9 73 201.5 70 216.6 72 219.6 69 300 229.4 67 271.2 72 278.1 71 289.6 73 305.4 87 200 333.15 128.9 19 146.4 43 165.0 65 184.7 97 216.6 115 100 229.4 114 261.8 132 282.2 144 293.3 146 0 303.6 124 353.15 100.5 4 50 109.9 7 111.0 11 123.2 16 135.4 28 145.9 45 155.1 59 165.0 87 174.2 115 183.6 118 195.1 145 207.9 162 216.0 183 225.8 200 239.8 235 264.8 277 286.2 316 299.5 309 304 307.1 1: Obtained by digitizing the graph in the original article. Synonym: 2-Chloro-4-ethylamino-6-isopropylamino-s-triazine Source: Knez, Z.; R izner-Hras, A.; K okot, K .; Bauman, D. Fluid Phase Equil. (1998), 152(1), 95-108.

150

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250 P (bar)

350

72

Solubility in Supercritical Carbon Dioxide

Atropine (C17H23NO3, MW=289.37) (g/L) 0.32 0.47 0.53 0.58 0.80 0.81 0.92 0.87 0.75 0.52 0.87 1.09 1.37 1.96 2.28 3.72 2.70 3.19 0.60 0.74 1.07 1.25 2.30 2.75 2.91 3.53 3.75 0.30 0.63 1.37 2.13 3.24 4.25 4.59 5.39 5.51 0.20 0.56 1.70 2.86 4.21 5.38 6.69 7.99 8.92

y1)

x

[A-79]

106 60 90 90 100 140 140 150 140 120 120 180 210 250 350 400 630 450 530 190 170 220 250 430 500 520 620 650 100 170 320 450 650 820 860 980 990 90 180 440 670 910 1100 1320 1520 1670

1800

1200

308 K 318 K 328 K 338 K 348 K

y x 106

T (K) P (bar) 308 122 152 182 213 243 274 304 334 355 318 122 152 182 213 243 274 304 334 355 328 122 152 182 213 243 274 304 334 355 338 122 152 182 213 243 274 304 334 355 348 122 152 182 213 243 274 304 334 355

S1)

600

0 100

1: The solubility at 348 K and 122 bar must have been misprinted and thus was re-calculated from S in the source table. Synonym: Tropine tropate Source: Yamini, Y.; Hassan, J.; Haghgo, S. J. Chem. Eng. Data (2001), 46(2), 451-455.

CAT4240—CHAPTER 1—31/10/2006—18:15—MUGUNTHAN—XML MODEL C – pp. 19–73

200

300 P (bar)

400

Solubility Data A

73

Azobenzene (C12H10N2; MW=182.22)

[A-80]

106

12000

y x 106

yx T (K) P (bar) 91 308.2 3640 101 4060 152 5040 203 5540 253 5980 318.2 91 2990 101 5130 152 8240 203 9260 253 9840 Synonym: Diphenyldiazene Source: Maeda, S.; Mishima, K.; Matsuyama, K.; Baba, M.; Hirabaru, T.; Ishikawa, H.; Hayashi, K.-I. J. Chem. Eng. Data (2001), 46(3), 647-650.

8000

4000

308.2 K 318.2 K

0 50

150 P (bar)

Azobenzene (C12H10N2; MW=182.22)

[A-81]

6

16000 y x 106

y x 10 T (K) P (bar) 333.2 101 2250 152 7600 203 12300 253 13600 Synonym: Diphenyldiazene Source: Mishima, K.; Matsuyama, K.; Ishikawa, H.; Hayashi, K-I.; Maeda, S. Fluid Phase Equil. (2002), 194-197, 895-904.

250

8000 0

50

CAT4240—CHAPTER 1—31/10/2006—18:15—MUGUNTHAN—XML MODEL C – pp. 19–73

150 P (bar)

250

2

Solubility Data B

Barium bis(hexafluoroacetylacetonate) (C10H2BaF12O4; FW = 551.43) 300 y x 106

y x 106 T (K) P (bar) 423.15 120 79 170 220 220 240 443.15 120 13 170 86 220 160 Synonym: Bis(1,1,1,5,5,5-hexafluoro2,4-pentanedionato)barium Source: M'Hamdi, R.; Bocquet, J.; Chhor, K.; Pommier, C. J. Supercrit. Fluids (1992), 5(1), 55-59.

423 K 443 K

150

0 100

150

200

x

[B-2]

106

1.46 4.00 22.70 25.30 28.20 43.20 80.00 86.40 86.40 0.19 0.50 2.30 4.68 8.88 10.90 26.20 30.00 33.90 49.00

90 308.15 K 328.15 K 373.15 K

y x 106

T (K) P (bar) 308.15 82.4 99.0 113.8 129.4 146.1 160.8 196.1 210.8 226.5 328.15 82.4 99.0 113.8 129.4 146.1 160.8 177.5 196.1 210.8 226.5

250

P (bar)

Beclomethasone-17, 21-dipropionate (C28H37ClO7; MW=521.04) y1)

[B-1]

60

30

0 50

150

250

P (bar)

75

CAT4240—CHAPTER 2—31/10/2006—18:27—MUGUNTHAN—XML MODEL C – pp. 75–149

76

Solubility in Supercritical Carbon Dioxide

373.15

99.0 0.12 113.8 0.55 129.4 0.80 146.1 3.21 160.8 6.01 177.5 8.95 196.1 10.10 210.8 12.50 226.5 30.90 1: The solubilities at 129.4 and 146.1 bar at 373.15 K were misprinted in the journal and thus corrected with the authors' consent. Synonym: 9a -Chloro-16b-methylprednisolone 17,21-dipropionate Source: Dean, J. R.; Kane, M.; Khundker, S.; Dowle, C.; Tranter, R. L.; Jones, P. Analyst (1995), 120(8), 21532157.

Beef shank fat P (bar)

y x 106 (wt%) 308 89.3 7.0 240000 96.0 7.0 260000 109.3 7.0 330000 128.0 7.0 360000 142.7 7.0 385000 158.7 7.0 660000 308 96.0 8.0 270000 102.7 8.0 310000 110.7 8.0 390000 126.7 8.0 390000 140.0 8.0 440000 153.3 8.0 610000 1: Cosolvent in CO2. Source: Acosta, G. M.; Smith, R. L. Jr.; Walsh, J. E.; Boni, K. A. J. Food Sci. (1995), 60(5), 983-987.

7 wt% 8 wt%

600000 y x 106

T (K)

[B-3] Propane1)

400000

200000 80

.

CAT4240—CHAPTER 2—31/10/2006—18:28—MUGUNTHAN—XML MODEL C – pp. 75–149

120 P (bar)

160

Solubility Data B

77

Behenic acid (C22H44O2; MW=340.58) x T(K) P(bar) S (g/L) 313.15 101.3 0.43 121.6 0.65 152.0 0.73 253.3 0.83 333.15 81.1 0.05 101.3 0.12 121.6 0.30 152.0 0.49 202.7 0.72 1: Calculated from S. Synonym: Docosanoic acid Source: Chrastil, J. J. Phys. Chem. (1982), 86(15), 3016-3021.

[B-4]

106 87 116 120 121 33 52 86 103 127

150

y x 106

y1)

100 50

313.15 K 333.15 K

0 50

100

150

200

250

P (bar)

Behenic acid (C22H44O2; MW=340.58)

308.15

P(bar) 80

85

95

110

135

160

(mol%) 0.00 1.41 2.14 3.09 3.48 0.00 1.41 2.37 2.93 0.00 1.21 2.00 2.50 2.51 3.36 0.00 1.35 2.06 2.89 0.00 1.26 1.96 3.15 0.00 1.27 1.73 1.93 3.00

[B-5]

y x 106 6.8 20.0 45.9 55.6 64.7 9.1 28.0 61.9 71.3 10.7 27.8 44.7 75.4 77.0 83.7 12.3 36.9 58.1 97.5 13.2 36.5 63.7 108.0 13.8 50.2 60.0 93.2 131.0

150 80 bar 85 bar 95 bar 110 bar 135 bar 160 bar

100 y x 106

T(K)

Ethanol1)

308.15 K

50

0 0

0

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2 Ethanol (mol%)

3

4

78

Solubility in Supercritical Carbon Dioxide

80

95

115

125

135

160

0 1.80 3.40 5.47 0 1.64 3.42 5.65 0 1.34 3.06 4.06 0 2.60 4.52 5.94 0 2.76 4.41 6.67 0 1.31 3.15 4.46 4.74

5.8 23.4 76.3 142.0 10.5 25.6 116.0 307.0 18.4 36.2 132.0 195.0 24.4 115.0 286.0 499.0 29.2 186.0 406.0 829.0 35.1 84.2 284.0 516.0 547.0

900 80 bar 95 bar 115 bar 125 bar 135 bar 160 bar

600 y x 106

318.15

318.15 K

300

0 0

2

4

6

Ethanol (mol%)

1: Cosolvent in CO2. Synonym: Docosanoic acid Source: Guan, B.; Liu, Z.; Han, B.; Yan, H. J. Supercrit. Fluids (1999), 14(3), 213-218.

Behenic acid (C22H44O2; MW=340.58)

308.15

P(bar) 80

85

95

110

[B-6]

y x 106 6.8 7.9 13.2 18.2 9.1 11.2 12.6 16.6 20.9 10.7 13.5 19.1 25.1 26.3 12.3 15.8 21.9 31.6

80 bar 308.15 K 85 bar 95 bar 110 bar 135 bar 160 bar

40

30 y x 106

T (K)

n -Octane1) (mol%) 0.00 1.03 2.14 3.04 0.00 1.04 1.94 2.08 2.85 0.00 1.03 2.06 3.06 3.24 0.00 1.11 2.16 3.01

20

10

0 0

1 2 n -Octane (mol %)

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3

Solubility Data B

160

318.15

90

95

110

125

135

160

0.00 1.15 2.05 2.89 3.06 0.00 0.96 1.98 2.75 0.00 1.24 2.57 4.77 0.00 0.98 1.10 2.88 6.34 0.00 1.12 3.02 6.66 0.00 1.63 2.09 6.00 0.00 1.09 2.93 6.20 0.00 1.07 3.00 5.85

13.2 18.2 24.0 34.7 34.9 13.8 20.9 25.1 40.7 5.8 9.4 20.8 91.1 10.5 18.6 19.5 41.7 263.0 18.4 35.9 69.0 271.0 24.4 64.7 67.0 282.0 29.2 54.5 92.0 278.0 35.1 65.1 122.0 307.0

90 bar 95 bar 318.15 K 110 bar 125 bar 135 bar 160 bar

300

y x 106

135

79

200

100

0 0

2 4 n -Octane (mol %)

6

1: Cosolvent in CO2. Synonym: Docosanoic acid Source: Guan, B.; Liu, Z.; Han, B.; Yan, H. J. Chem. Eng. Data (1999), 44(6), 1204-1206.

Behenic acid (C22H44O2; MW=340.58) T (K)

nP (bar) Pentane1) (mol%)

318.15

90

0.00 2.06 3.33 5.17

y x 106 5.9 12.0 26.3 41.0

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[B-7]

80

Solubility in Supercritical Carbon Dioxide

110

135

160

328.15

90

95

100

110

135

160

10.5 22.4 39.8 42.2 126. 21.4 43.7 44.7 18.2 32.4 45.7 77.6 29.5 53.7 56.1 79.4 35.5 64.6 85.1 112.0 3.2 10.5 21.4 60.3 6.3 19.5 43.3 63.1 10.2 35.5 63.1 81.3 16.3 68.7 104.0 138.0 61.7 231.0 251.0 275.0 112.0 251.0 355.0 398.0

120 90 bar 318.15 K 95 bar 100 bar 110 bar 135 bar 160 bar

80 y x 106

100

0.00 2.94 4.05 5.03 0.00 1.89 4.08 5.08 0.00 2.92 3.81 5.64 0.00 2.69 3.61 4.57 0.00 2.68 3.36 4.87 0.00 4.07 5.36 7.50 0.00 3.08 6.07 7.16 0.00 4.34 5.17 6.15 0.00 3.74 5.19 5.54 0.00 3.77 4.73 5.59 0.00 3.53 4.13 5.59

40

0 0

2

4

6

n -Pentane (mol %)

90 bar 95 bar 100 bar 110 bar 135 bar 160 bar

400

300 y x 106

95

328.15 K

200

100

0 0

2 4 6 n -Pentane (mol %)

1: Cosolvent in CO2. Synonym: Docosanoic acid Source: Guan, B.; Liu, Z.; Han, B.; Yan, H. J. Chem. Eng. Data (1999), 44(6), 1204-1206.

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8

Solubility Data B

81

Behenyl behenate (C44H88O2; MW=649.17) y1) x 106 T(K) P(bar) S (g/L) 313.15 101.3 0.204 21.5 121.6 0.310 66.6 152.0 0.400 79.4 202.7 0.501 92.5 333.15 121.6 0.242 83.5 152.0 0.719 182.0 202.7 1.210 258.0 331.0 253.3 1.680 1: Calculated from S. Synonym: Docosyl docosanoate Source: Chrastil, J. J. Phys. Chem. (1982), 86(15), 3016-3021.

[B-8] 400

y x 106

313.15 K 333.15 K

200

0 50

150

250

P (bar)

[B-9]

Benzaldehyde (C7H6O; MW=106.12) y x 106 700 700 800 900 800 1400 1400 2200 2300 1200 2100 1700 2200 4000 9500 20700 1500 1500 2700 7700 15200 27100 2100 3100 2800 3600 3600 7300 6700 13900 20100 20900 42200 74700

80000 313.2 K 333.2 K 353.2 K 373.2 K 393.2 K

60000 y x 106

T (K) P (bar) 313.2 61.0 66.0 66.0 71.0 71.1 76.1 76.1 81.1 81.1 333.2 61.5 71.7 81.8 91.9 102.1 112.2 117.3 353.2 61.5 81.8 102.1 122.5 142.6 152.7 373.2 61.5 81.8 81.8 102.1 102.1 122.5 122.5 142.6 162.8 162.8 183.0 203.2

40000

20000

0 50

100

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150 P (bar)

200

250

82

393.2

Solubility in Supercritical Carbon Dioxide

61.7 81.8 102.1 122.4 141.2 162.8 183.0 203.2 223.4

6000 7900 7800 7100 12200 21000 30900 46300 70400

Synonym: Benzoic aldehyde Source: Walther, D.; Maurer, G. Ber. Bunsenges. Phys. Chem. (1992), 96(8), 981-988.

Benzaldehyde (1) + 1-Methylnaphthalene (2) Mixture P (bar)

(wt%)

y1 x 106

372.6

0 500 34.1 0 700 74.4 0 900 115.4 0 1600 157.8 0 3000 195.0 0 4900 232.9 373.2 35.2 0.27 51300 0.24 30900 75.1 0.31 26900 117.8 0.55 25900 158.2 1.27 21700 193.6 219.1 1.98 18900 1: Cosolvent in CO2. Source: Reilly, J.; Kim, C.; Clark, A.; Donohue, M. Fluid Phase Equil. (1992), 73(1-2), 81-107.

60000

y2 x 106 4500 2300 3000 4900 15000 21600 500 600 900 1700 3000 4400

[B-10] BA, CO2 BA, w/ MeOH MN, CO2 MN, w/ MeOH

40000 y x 106

T (K)

Methanol1)

20000

0 0

Benzocaine (C9H11NO2; MW=165.19) T (K) P (bar) 308 122 152 182 213 243 274 304 355 318 122 152 182 213

S (g/L) 2.98 3.27 4.10 4.56 4.96 5.64 6.26 7.18 2.63 3.39 4.55 5.62

yx

106 1030 1060 1280 1380 1470 1640 1760 2000 1060 1240 1530 1810

CAT4240—CHAPTER 2—31/10/2006—18:28—MUGUNTHAN—XML MODEL C – pp. 75–149

80

160 P (bar)

240

[B-11]

Solubility Data B

83

12000

y x 106

243 5.83 1820 274 6.69 2030 304 7.64 2280 355 7.78 2250 328 122 1.61 830 152 3.31 1340 182 5.15 1890 213 7.27 2510 243 8.50 2830 274 10.84 3460 304 11.56 3600 355 12.99 3900 338 122 0.58 390 152 2.68 1270 182 2.67 2300 213 8.39 3130 243 12.12 4260 274 16.61 5600 304 19.74 6440 355 25.06 7820 348 122 0.33 270 152 1.73 960 182 4.47 2030 213 8.10 3300 243 13.06 4930 274 20.61 7370 304 25.28 8650 355 37.35 12120 Synonyms: 4-Aminobenzoic acid ethyl ester; Ethyl 4-aminobenzoate Source: Garmroodi, A.; Hassan, J.; Yamini, Y. J. Chem. Eng. Data (2004), 49(3), 709-712.

8000

308 K 318 K 328 K 338 K 348 K

4000

0 100

200

Benzocaine (C9H11NO2; MW=165.19) T (K) P (bar) 298 84 95 109 125 153 176 211 225 248

y x 106 46.5 74.7 101.0 114.0 128.0 135.0 173.0 191.0 209.0

CAT4240—CHAPTER 2—31/10/2006—18:28—MUGUNTHAN—XML MODEL C – pp. 75–149

300

400

P (bar)

[B-12]

84

Solubility in Supercritical Carbon Dioxide

308

298 K 308 K 318 K

200 150 y x 106

88 17.9 99 21.2 105 28.0 114 30.9 124 34.3 149 52.5 175 73.6 208 80.7 224 121.0 251 163.0 318 99 24.0 104 17.5 110 23.5 114 25.2 124 30.5 150 43.6 172 44.6 199 55.5 225 82.6 250 119.0 Synonyms: 4-Aminobenzoic acid ethyl ester; Ethyl 4-aminobenzoate Source: Weinstein,R. D.;Muske, K. R.; Moriarty, J.; Schmidt, E. K. J. Chem. Eng. Data (2004), 49(3), 547-552.

100 50 0 0

100

200

300

P (bar)

Benzoic acid (C7H6O2; MW=122.12)

[B-13]

y x 106

y x 106 T (K) P (bar) 5000 318 90 144 100 432 115 1000 2500 116 868 137 1320 148 1990 0 150 1730 174 2700 50 200 3110 205 3340 210 3410 230 4310 Source: Galia, A.; Argentino, A.; Scialdone, O.; Filardo, G. J. Supercrit. Fluids (2002), 24(1), 7-17.

CAT4240—CHAPTER 2—31/10/2006—18:28—MUGUNTHAN—XML MODEL C – pp. 75–149

150 P (bar)

250

Solubility Data B

85

[B-14]

Benzoic acid (C7H6O2; MW=122.12) 12000

y x 106

y x 106 T(K) P(bar) 318 120 1140 160 2370 200 3180 240 4210 280 4380 328 120 490 160 2270 200 3860 240 5160 280 7340 338 120 320 160 1720 200 4100 240 6950 9830 280 Source: Kurnik, R. T.; Holla, S. J.; Reid, R. C. J. Chem. Eng. Data (1981), 26(1), 47-51.

8000

318 K 328 K 338 K

4000 0 100

200 P (bar)

[B-15]

Benzoic acid (C7H6O2; MW=122.12) 106

6000

y x 106

yx T(K) P(bar) 318.15 120 987 160 2110 200 2650 220 3290 240 3510 270 3750 328.15 160 1920 200 3190 220 4030 240 4310 270 4640 Source: Lee, L.-s.; Huang, J.-f.; Zhu, O.- x. J. Chem. Eng. Data (2001), 46(5), 1156-1159.

4000

318.15 K 328.15 K

2000

0 100

Benzoic acid (C7H6O2; MW=122.12) T (K) P (bar) 308.25 101.0 113.0 120.0 151.0 160.0 240.0 280.0 282.3 363.8

300

y x 106 800 1030 1380 1740 2370 3100 3310 2930 3150

CAT4240—CHAPTER 2—31/10/2006—18:28—MUGUNTHAN—XML MODEL C – pp. 75–149

200

300

P (bar)

[B-16]

86

Solubility in Supercritical Carbon Dioxide

318.25

15000

10000

308.2 K 318.2 K 328.2 K 343.2 K

y x 106

101.0 260 105.0 493 113.0 561 120.0 1150 151.0 1980 160.0 2380 200.0 3180 240.0 4210 280.0 4390 282.3 4010 302.5 4444 363.1 4870 328.25 101.0 140 105.0 220 111.0 300 120.0 490 126.0 750 151.2 1940 160.0 2270 200.4 3830 240.0 5160 281.0 5680 302.5 6380 363.3 7170 343.25 101.0 122 111.0 222 126.0 550 151.2 1540 200.9 5000 281.0 9020 364.1 12800 Source: Schmitt, W. J.; Reid, R. C. J. Chem. Eng. Data (1986), 31(2), 204212.

5000

0 100

200

300 P (bar)

Benzoic acid (C7H6O2; MW=122.12)

[B-17]

P1)

800 y x 106

(bar) S1) (mg/Nl2)) y3) x 106 80 0.140 25.5 85 0.470 85.7 90 1.570 286.0 100 3.360 613.0 1: Obtained by digitizing the graph in the original article. 2: "Nl" means "Normliter," which is one liter at 273.15 K and 1 atm. 3: Calculated from S. Source: Stahl, E.; Schilz, W. Talanta (1979), 26, 675-679. T(K) 313.15

400

400

0

70

CAT4240—CHAPTER 2—31/10/2006—18:28—MUGUNTHAN—XML MODEL C – pp. 75–149

80

90 100 P (bar)

110

Solubility Data B

87

Benzoic acid (C7H6O2; MW= 122.12)

308.15

P(bar) 120 160 200 240 280 100 120 120 150 200 250 330 90 100 120 120 150 200 250 250 350 350 100 150 250 300 300

Cosolvent (mol%) 0.0 0.0 0.0 0.0 0.0 Acetone 3.5 3.5 3.5 3.5 3.5 3.5 3.5 Methanol 3.5 3.5 3.5 3.5 3.5 3.5 3.5 3.5 3.5 3.5 Octane 3.5 3.5 3.5 3.5 3.5

y x 106 1250 2190 2530 2810 3030 3340 3830 3980 4490 5370 5920 6400 5330 6010 7430 7180 8770 10100 10600 10900 11200 11900

15000 CO2 Acetone MeOH Octane

10000 y x 106

T(K)

[B-18]

5000

0 50

150

250

350

P (bar)

2900 4310 5550 6070 5820

Source: Dobbs, J. M.; Wong, J. M.; Lahiere, R. J.; Johnston, K. P. Ind. Eng. Chem. Res. (1987), 26(1), 56-65. [B-19]

Benzoic acid (C7H6O2; MW= 122.12)

318.15

328.15

P(bar)

120 150 150 200 200 120 150 200

Cosolvent (mol%) Methanol (3.5%) 3.5 3.5 3.5 3.5 3.5 3.5 3.5 3.5

y x 106

6900 9300 9400 11200 11400 5830 9490 13600

15000 y x 106

T(K)

318.15 K 328.15 K

10000

5000 100

Source: Dobbs, J. M.; Johnston, K. P. Ind. Eng. Chem. Res. (1987), 26(7), 1476-1482.

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150 P (bar)

200

88

Solubility in Supercritical Carbon Dioxide

Benzoic acid (C7H6O2; MW=122.12)

[B-20]

308.15 K 318.15 K 328.15 K

y x 106

EA + T (K) P (bar) EtOH1) y x 106 (mol%) 9000 308.15 80 2.0 714 110 2.0 1191 130 2.0 2022 170 2.0 3173 6000 200 2.0 3822 230 2.0 4532 318.15 80 2.0 203 110 2.0 823 130 2.0 1677 3000 170 2.0 3875 200 2.0 4991 230 2.0 5558 328.15 80 2.0 102 0 110 2.0 692 130 2.0 1417 50 170 2.0 4696 200 2.0 7418 230 2.0 8656 1: Mixed cosolvent in supercritical CO2 (ethyl acetate and ethanol) with molar ratio of 1:1. Source: Jin, J.; Zhong, C.; Zhang, Z.; Li, Y. Fluid Phase Equil. (2004), 226, 9-13.

150 P (bar)

[B-21]

Benzoic acid Cosolvent y x 106 (mol%) 80 0.0 70 110 0.0 339 130 0.0 637 170 0.0 2448 200 0.0 3698 230 0.0 4233 Ethyl Actetate 80 2.0 121 110 2.0 642 130 2.0 1073 170 2.0 3335 200 2.0 4254 230 2.0 4896 Ethanol 80 2.0 366 110 2.0 3934 130 2.0 8092 170 2.0 13594 200 2.0 15305 230 2.0 16821

P (bar)

328.15

18000 Pure CO2 Ethyl Actetate Ethanol

12000 y x 106

T (K)

250

6000

0 50

1: Cosolvent in supercritical CO2. Source: Jin, J.; Zhong, C.; Zhang, Z.; Li, Y. Fluid Phase Equil. (2004), 226, 9-13.

CAT4240—CHAPTER 2—31/10/2006—18:28—MUGUNTHAN—XML MODEL C – pp. 75–149

150 P (bar)

250

Solubility Data B

89

[B-22]

Benzoic acid (C7H6O2; MW=122.12) P (bar)

308.15 137.8 138.1 172.4 172.4 239.8 241.2 287.1 287.4

(mol%) 1.10 1.10 1.10 1.10 1.10 1.10 1.10 1.10

y x 106 7740 7770 9230 8930 9870 9830 10300 10400

12000 y x 106

T (K)

TBP1)

9000

6000 100

200

1:Tri-n-butyl phosphate as a cosolvent in CO2 on a solute-free basis. Source: Lemert, R. M.; Johnston, K. P. Ind. Eng. Chem. Res. (1991), 30(6), 1222-1231.

300

P (bar)

[B-23]

Benzoic acid (C7H6O2; MW=122.12) Cosolvent y x 106 (mol%) Benzene 328.15 200.0 3.0 9020 3.0 7020 7.6 16400 7.9 14400 Acetone 202.0 6410 3.5 202.0 17800 9.3 Cyclohexane 202.0 5180 3.0 202.0 11200 6.5 Methylene Chloride 202.0 12400 5.4 12.7 202.0 18800 Source: Schmitt, W. J.; Reid, R. C. Fluid Phase Equil. (1986), 32(1), 77-99.

20000

P (bar)

15000 y x 106

T (K)

10000

P = ~ 200 bar Benzene Acetone Cyclohexane CH2Cl2

5000 0 0

5

10

Cosolvent (mol%)

CAT4240—CHAPTER 2—31/10/2006—18:28—MUGUNTHAN—XML MODEL C – pp. 75–149

15

90

Solubility in Supercritical Carbon Dioxide

Benzoic acid (C7H6O2; MW=122.12) Ethane1) y x 106 (mol%) 328.15 116.0 6.2 380 140.0 6.2 1340 199.5 6.2 3810 274.0 6.2 5840 364.0 6.2 7240 343.35 116.0 6.2 290 140.0 6.2 990 199.5 6.2 4680 274.0 6.2 9320 364.0 6.2 12600 1: Cosolvent in CO2. Source: Schmitt, W. J.; Reid, R. C. Fluid Phase Equil. (1986), 32(1), 77-99.

14000

P (bar)

328 K 343 K

y x 106

T (K)

[B-24]

7000

0 100

200

300 P (bar)

[B-25]

Benzoic acid (C7H6O2; MW=122.12)

318 120.5 160.5 200.6 241.6 281.6 121.5 153.7 201.6 262.1 321.7 103.9 121.5 150.8 204.5 262.1 323.6 102.0 119.5 151.8 203.5 261.1 321.7

Cosolvent2) (mol%) 0 0 0 0 0 Acetone 3.7 3.7 3.7 3.7 3.7 Ethanol 3.7 3.7 3.7 3.7 3.7 3.7 n-Hexane 3.7 3.7 3.7 3.7 3.7 3.7

y1) x 106 1920 2920 3580 4360 4540 4200 5300 5810 6290 6940 6350 7150 8050 8700 10000 10200

12000

8000 y x 106

T(K) P1) (bar)

400

4000

2530 3140 3880 4320 5500 6020

Pure CO2 Acetone Ethanol n-Hexane

0 50

150

1: Obtained by digitizing the graph in the original article. 2: Cosolvent in CO2 on a solute-free basis. Source: Zhang, J.; Zhu, M.; Yu, E.; Zhang, Z. Chinese J. Chem. Eng. (1993), 1(4), 239-246.

CAT4240—CHAPTER 2—31/10/2006—18:28—MUGUNTHAN—XML MODEL C – pp. 75–149

250 P (bar)

350

Solubility Data B

91

[B-26]

Benzoic acid (1) + Hexamethylbenzene (2) Mixture1) Methanol2) y1 x 106 y2 x 106 (mol%) 308.15 100 0.0 1510 1110 120 0.0 1730 1380 150 0.0 2370 1610 200 0.0 2880 1830 250 0.0 3570 2080 350 0.0 3980 2150 120 3.5 7900 2250 150 3.5 8380 2480 200 3.5 11200 2930 250 3.5 12400 2820 350 3.5 13400 2850 1: The solubility was measured from a mixture of solids 1 and 2 of 50:50 wt%. 2: Cosolvent in CO2. Source: Dobbs, J. M.; Johnston, K. P. Ind. Eng. Chem. Res. (1987), 26(7), 1476-1482.

15000

P(bar)

y x 106

T(K)

10000

(1) CO2 (1) MeOH (2) CO2 (2) MeOH

5000

0 50

150

250 P (bar)

[B-27]

Benzoin (C14H12O2; MW=212.24) 450

300

308.15 K 318.15 K 328.15 K

y x 106

y × 106 T (K) P (bar) 308.15 121.6 120 134.7 148 154.0 188 175.4 201 204.4 223 236.1 257 318.15 111.3 53 135.4 127 152.7 192 189.9 240 198.8 283 218.1 302 241.9 333 328.15 114.8 41 142.3 141 168.5 228 196.1 312 219.5 360 244.3 410 Synonyms: (±)-2-Hydroxy-2-phenylacetophenone; (±)-2-Hydroxy-1,2-diphenylethanone Source: Cheng, K.-W.; Tang, M.; Chen, Y.-P. Fluid Phase Equil. (2002), 201(1), 79-96.

350

150

0 100

CAT4240—CHAPTER 2—31/10/2006—18:28—MUGUNTHAN—XML MODEL C – pp. 75–149

150

200 P (bar)

250

92

Solubility in Supercritical Carbon Dioxide

Benzonitrile (C7H5N; MW=103.12)

[B-28]

y x 106

T (K) P (bar) y x 106 313.2 60.9 800 65.9 800 65.9 700 70.9 1300 70.9 1200 75.9 1400 80.9 2800 80.9 3000 353.2 60.9 1900 80.9 2300 80.9 2200 100.9 3500 100.9 3700 120.9 6900 120.9 7200 140.9 13900 160.8 37000 160.8 35600 393.2 64.9 6200 80.9 6600 100.9 7700 100.9 7600 120.9 9400 120.9 9400 140.9 12200 140.9 12000 140.9 11600 160.9 16300 160.9 16500 160.9 15800 180.9 22400 180.9 23600 Synonyms: Benzenecarbonitrile; Cyanobenzene Source: Walther, D.; Maurer, G. J. Chem. Eng. Data (1993), 38, 247-249.

40000 313.2 K 353.2 K 393.2 K

30000

20000

10000

0 50

100

Benzo[ghi]perylene (C22H12; MW=276.33) T (K) P (bar) 313 250 300 350 400 373 150 200 250 300 350 400 450

yx

106 0.18 0.27 0.31 0.33 0.15 0.43 1.60 2.70 4.00 4.80 5.40

CAT4240—CHAPTER 2—31/10/2006—18:28—MUGUNTHAN—XML MODEL C – pp. 75–149

150

200

P (bar)

[B-29]

Solubility Data B

93

100 1.70 150 2.50 200 6.80 250 16.00 300 37.00 350 57.00 400 87.00 450 108.00 523 100 2.90 150 9.70 200 29.30 250 63.30 300 123.00 350 231.00 400 326.00 450 455.00 Synonym: 1,12-Benzoperylene Source: Miller,D. J.;Hawthorne,S. B.;Clifford, A. A.; Zhu, S. J. Chem. Eng. Data (1996), 41(4), 779-786.

y x 106

423

500 313 K 373 K 423 K 523 K

400 300 200 100 0 0

100

200

300

400

P (bar)

Benzyl alcohol (C7H8O; MW=108.14) yx

[B-30]

106

409 286 268 277 291 349 763 1920 4850 10600 6710 3510 2680 2360 2110 2290 3470 4830 7290 14500 40700 29500 23600 19900 17200

50000 333.15 K 393.15 K 453.15 K

40000 y x 106

T (K) P (bar) 333.15 10 20 30 40 50 60 90 120 150 190 393.15 10 20 30 40 50 60 90 120 150 190 453.15 10 20 30 40 50

500

30000 20000 10000 0 0

50

CAT4240—CHAPTER 2—31/10/2006—18:28—MUGUNTHAN—XML MODEL C – pp. 75–149

100 P (bar)

150

200

94

Solubility in Supercritical Carbon Dioxide

60 16200 90 15500 120 16100 150 17100 190 20500 Synonym: Benzenemethanol Source: C hen,J.-T.;Lee,M.-J. Fluid Phase Equil.(1997), 130(1-2), 231-241.

Benzyl alcohol (C7H8O; MW=108.14) 300 300 600 500 700 600 700 2700 2800 7600 8300 11000 11300 11500 11600 13600 13500 900 900 800 1200 2600 5200 5000 8700 9000 2500 2400 3200 2900 3700 3800 4600 4500 6100

18000 313.2 K 353.2 K 393.1 K

12000 6

yx

y x 10

T (K) P (bar) 313.2 60.9 60.9 80.9 80.9 80.9 80.9 80.9 90.9 90.9 100.9 100.9 120.9 120.9 120.9 120.9 140.9 140.9 353.2 60.9 80.9 80.9 100.9 120.9 140.9 140.9 160.8 160.8 393.1 60.9 60.9 80.9 80.9 100.9 100.9 120.9 120.9 140.9

[B-31]

106

6000

0 50

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100

150 P (bar)

200

Solubility Data B

95

140.9 5500 160.8 7900 180.8 11400 180.8 11400 200.8 15900 200.8 16000 Synonym: Benzenemethanol Source: Walther, D.; Maurer, G. J. Chem. Eng. Data (1993), 38, 247-249.

Betamethasone (C22H29FO5; MW=392.46)

[B-32]

106

0.4 308.15 K 328.15 K

0.3 y x 106

yx T (K) P (bar) 308.15 82.4 0.013 99.0 0.037 113.8 0.077 129.4 0.121 146.1 0.149 160.8 0.228 177.5 0.267 196.1 0.331 210.8 0.345 226.5 0.363 328.15 82.4 0.001 99.0 0.004 113.8 0.025 129.4 0.036 146.1 0.047 160.8 0.077 177.5 0.083 196.1 0.112 210.8 0.121 226.5 0.128 Synonym: 9a-Fluoro-16b-methylprednisolone Source: Dean, J. R.; Kane, M.; Khundker, S.; Dowle, C.; Tranter, R. L.; Jones, P. Analyst (1995), 120(8), 21532157.

0.2

0.1

0.0 50

Betamethasone 17, 21-dipropionate (C28H37FO7; MW=504.59) T (K) P (bar) 308.15 82.4 99.0 113.8 129.4 146.1 160.8 177.5 196.1 210.8 226.5

yx

106

0.56 2.72 3.48 6.39 21.90 23.90 46.60 53.00 60.60 67.20

CAT4240—CHAPTER 2—31/10/2006—18:28—MUGUNTHAN—XML MODEL C – pp. 75–149

150

250

P (bar)

[B-33]

96

Solubility in Supercritical Carbon Dioxide

328.15 113.8 0.21 129.4 1.70 146.1 4.62 160.8 13.80 177.5 18.80 196.1 26.20 210.8 58.40 226.5 70.30 373.15 129.4 0.85 146.1 3.11 160.8 8.99 177.5 11.90 196.1 21.20 210.8 55.50 226.5 61.90 Source: Dean, J. R.; Kane, M.; Khundker, S.; Dowle, C.; Tranter, R. L.; Jones, P. Analyst (1995), 120(8), 21532157.

80 308.15 K 328.15 K

y x 106

60

373.15 K

40

20

0 50

100

150

200

P (bar)

[B-34]

Bibenzyl (C14H14; MW=182.26) P (bar)

y x 106 308.15 84.7 7100 93.0 9500 103.7 12200 124.3 17300 136.1 20500 168.5 26100 189.0 30100 223.3 39500 276.0 49800 328.15 93.9 1000 107.3 2300 125.8 5400 146.1 11000 174.9 20600 186.8 22600 221.7 34500 Synonym: 1,2-Diphenylethane Source: Chung, S. T.; Shing, K. S. Fluid Phase Equil. (1992), 81, 321-341.

60000

y x 106

T (K)

250

308.15 K 328.15 K

40000 20000 0 0

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100

200 P (bar)

300

Solubility Data B

97

[B-35]

Biphenyl (C12H10; MW=154.21) T (K) P (bar) yx 308.15 79.9 4600 94.1 6100 111.4 8000 132.0 10100 164.0 12300 213.6 13900 271.2 15200 328.15 98.3 800 110.3 2700 133.7 10500 176.9 21000 208.0 24800 269.4 41100 Source: Chung, S. T.; Shing, K. S. Fluid Phase Equil. (1992), 81, 321-341. 106

308.15 K 328.15 K

y x 106

40000

20000

0 0

100

200 P (bar

[B-36]

Biphenyl (C12H10; MW=154.21) y x 106 10430 10770 12960 14310 15360 15460 15860 15410 15560 19590 22100 24150 25610 27380 27510 27220 17820 26890 31240 36050 37640 37950 37650 36050 4474 10310 14810 18290

200000

150000 y x 106

T (K) P (bar) 308.8 106.0 127.9 167.3 204.4 242.3 301.2 358.1 441.2 314.8 153.5 181.3 209.5 238.8 268.1 330.1 379.5 448.4 322.7 155.6 204.6 239.1 296.6 337.0 379.5 422.5 475.2 328.2 110.6 132.6 153.7 167.3

300

308.8 K 314.8 K 322.7 K 328.2 K 330.5 K

100000

50000

0 100

CAT4240—CHAPTER 2—31/10/2006—18:28—MUGUNTHAN—XML MODEL C – pp. 75–149

300 P (bar)

500

98

Solubility in Supercritical Carbon Dioxide

208.6 24780 231.6 32510 252.6 35160 296.6 43980 334.7 56150 386.7 68620 412.9 79180 443.9 97750 470.0 110540 482.8 126690 490.4 181650 330.5 361.5 63650 402.2 75630 430.4 92080 Synonym: 1,1'-Biphenyl Source: MCHugh, M.; Paulaitis, M. E. J. Chem. Eng. Data (1980), 25(4), 326329.

[B-37]

Biphenyl (C12H10; MW=154.21) yx

426 312 333 316 326 1285 1124 984 657 496 470 351 303 482 2069 1205 664 511 471 4364 4385 2485 1372 992 679 570

80 bar 85 bar 90 bar 95 bar 105 bar

6000

y x 106

P (bar) T (K) 80.0 313.75 318.35 323.15 328.25 333.25 85.0 313.16 313.36 313.45 315.45 318.05 318.25 323.25 328.35 333.15 90.0 315.75 317.85 322.85 327.85 332.65 95.0 315.35 315.45 318.05 321.05 323.15 328.15 333.15

106

4000

2000

0 310

320

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330 T (K)

340

Solubility Data B

99

105.0 313.05 6282 316.75 5901 318.45 5391 322.85 2978 327.95 1670 332.85 1174 Source: Zhao, S.; Wang, R.; Yang, G. J. Supercrit. Fluids (1995), 8(1), 15-19.

[B-38]

Biphenyl (C12H10; MW=154.21) Cosolvent2) y1) x 106 (mol%) 308 101 0 8970 119 0 10400 147 0 11300 198 0 13100 259 0 14500 322 0 14900 313 101 0 6840 30000 119 0 8730 149 0 11100 198 0 14100 258 0 16100 313 Acetone 20000 100 3.7 14000 120 3.7 15600 150 3.7 18700 200 3.7 22200 Ethanol 10000 100 3.7 11100 120 3.7 12300 150 3.7 16000 200 3.7 19000 260 3.7 21200 0 320 3.7 21900 50 Hexane 308 120 3.7 12800 150 3.7 15200 200 3.7 16400 260 3.7 18600 320 3.7 19600 313 100 3.7 14900 120 3.7 17000 150 3.7 19500 200 3.7 24300 260 3.7 25400 1: Obtained by digitizing the graph in the original article. 2: Cosolvent in CO2 on a solute-free basis. Synonym: 1,1'-Biphenyl Source: Zhang, J.; Zhu, M.; Yu, E.; Zhang, Z. Chinese J. Chem. Eng. (1993), 1(4), 239-246.

y x 106

T(K) P1) (bar)

CO2, 308 K CO2, 313 K Acetone,313 K Ethanol, 313 K Hexane, 308 K Hexane, 313 K

150

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250 P (bar)

350

100

Solubility in Supercritical Carbon Dioxide

[B-39]

Bisacodyl (C22H19NO4; MW=361.39) T (K)

P (bar)

S (g/L)

yx

106

308

308 K 318 K 328 K 338 K 348 K

y x 106

122 0.23 36 152 0.37 52 182 0.50 71 213 0.59 81 243 0.74 100 274 0.80 106 304 0.92 120 355 1.09 139 600 318 122 0.17 27 152 0.27 44 182 0.46 71 213 0.60 89 243 0.79 113 400 274 1.00 139 304 1.16 158 355 1.53 203 328 122 0.09 22 152 0.19 37 200 182 0.38 63 213 0.62 98 243 0.96 145 274 1.30 190 304 1.59 227 0 355 2.15 297 100 338 122 0.03 9 152 0.11 23 182 0.31 58 213 0.56 96 243 1.11 179 274 1.62 251 304 2.06 309 355 3.09 443 348 152 0.07 19 182 0.26 54 213 0.70 130 243 1.18 205 274 1.72 282 304 2.58 406 355 3.88 583 Synonym: 4,4'-(2-Pyridylmethylene)bisphenol diacetate Source: Asghari-Khiavi, M.; Yamini, Y. J. Chem. Eng. Data (2003), 48(1), 61-65.

200

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300 P (bar)

400

Solubility Data B

101

[B-40]

1,4-Bis(butylamino)anthraquinone (C22H26N2O2; MW=350.46)

310.1

320.0

P (bar)

M x 106 (mol/L)

y1) x 106

84.2 87.2 89.0 89.7 91.6 95.0 97.3 99.7 104.8 109.9 115.3 120.1 125.9 130.4 135.4 136.1 140.2 145.4 150.7 155.7 161.0 166.5 171.3 176.5 182.6 94.8 99.8 100.0 102.7 105.0 107.0 110.4 112.9 115.2 120.3 124.9 125.4 131.3 133.5 135.8 140.0 145.0 145.3 149.5 150.8

2.2 13.4 21.9 25.5 34.7 48.8 57.9 73.7 93.8 114.5 135.2 153.6 175.8 192.2 210.5 212.7 226.2 244.4 262.2 277.4 293.6 309.6 322.6 336.1 350.8 1.2 4.7 4.2 9.2 14.9 20.7 33.7 44.3 54.7 78.1 102.7 105.5 135.7 158.9 158.3 182.7 206.3 222.9 227.0 253.5

0.19 1.01 1.58 1.82 2.40 3.25 3.77 4.72 5.83 6.95 8.03 8.99 10.12 10.94 11.84 11.95 12.60 13.48 14.33 15.04 15.79 16.52 17.10 17.70 18.34 0.14 0.46 0.41 0.82 1.25 1.67 2.57 3.28 3.95 5.39 6.87 7.04 8.77 10.17 10.03 11.39 12.64 13.64 13.72 15.26

310.1 K 320.0 K 330.1 K 340.1 K

20

15 y x 106

T (K)

10

5

0 50

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100

150 P (bar)

200

102

Solubility in Supercritical Carbon Dioxide

330.1

340.1

155.6 160.5 165.1 170.7 104.0 109.1 114.0 119.1 122.4 125.0 129.7 133.3 136.7 140.5 141.0 142.5 145.9 149.6 154.6 155.4 159.8 160.1 164.6 165.6 169.7 170.8 175.7 119.7 124.4 129.9 134.9 139.2 145.3 150.7 155.8 161.0 166.0 171.6 176.2 178.0

278.4 304.3 325.2 350.5 1.1 2.8 6.3 13.8 20.9 28.5 47.6 63.7 81.1 102.6 104.8 115.2 137.3 159.9 195.1 202.8 230.6 237.5 263.2 278.8 294.7 314.6 347.7 4.2 7.4 14.1 23.6 35.2 59.0 86.3 120.5 156.9 198.3 246.8 288.5 311.4

16.55 17.87 18.90 20.13 0.14 0.32 0.64 1.28 1.84 2.41 3.81 4.92 6.08 7.48 7.61 8.28 9.67 11.03 13.14 13.61 15.20 15.63 17.04 17.98 18.75 19.95 21.73 0.50 0.82 1.43 2.25 3.18 5.01 7.00 9.40 11.84 14.55 17.61 20.17 21.61

1: Calculated from M. Synonym: C. I. Solvent Blue 35 Source: Kautz, C. B. Sc. D. Thesis, University of Bochum, Bochum, Germany, 1996.

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Solubility Data B

103 [B-41]

1,4-Bis(butylamino)anthraquinone (C22H26N2O2; MW=350.46) P (bar)

305.0

76.1 76.6 81.1 88.2 99.1 110.0 110.1 119.6 129.4 140.0 140.4 149.4 160.7 170.4 180.4 190.6 86.2 91.1 97.8 108.0 118.1 127.5 137.0 147.0 151.7 161.7 171.3 180.8 190.8 92.6 94.4 98.2 103.8 104.0 109.6 114.6 120.0 120.1 131.0 140.0 150.0 161.0 171.4

310.0

315.0

M x 106 (mol/L) 15.7 18.3 35.9 55.6 82.6 108.8 108.8 129.7 150.7 173.3 174.2 191.7 214.1 238.9 257.9 280.9 15.1 32.9 55.5 87.1 118.4 146.3 171.6 199.9 217.9 242.7 274.0 305.6 337.6 6.4 11.0 22.8 42.9 42.6 63.4 81.0 101.5 101.6 140.6 174.0 209.1 253.1 297.8

y1) x 106 1.15 1.31 2.35 3.43 4.84 6.16 6.16 7.18 8.18 9.25 9.29 10.09 11.10 12.25 13.09 14.12 1.19 2.29 3.60 5.32 6.97 8.38 9.62 10.99 11.89 13.04 14.53 16.01 17.49 0.59 0.94 1.75 3.02 3.00 4.24 5.24 6.38 6.39 8.47 10.21 11.97 14.17 16.38

30

305 K 310 K 315 K 320 K 330 K 340 K

20 y x 106

T (K)

10

0 50

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100

150 P (bar)

200

104

320.0

330.0

340.0

Solubility in Supercritical Carbon Dioxide

180.4 189.4 99.6 105.0 109.5 109.6 115.5 121.5 131.0 141.4 145.5 151.0 161.1 161.9 171.8 181.9 188.7

337.7 375.6 5.9 17.4 31.9 32.0 53.7 77.2 118.0 163.6 182.1 206.2 258.4 262.7 319.1 377.7 416.4

18.33 20.14 0.58 1.47 2.47 2.47 3.86 5.28 7.64 10.15 11.14 12.41 15.15 15.38 18.29 21.25 23.17

113.3 118.6 123.5 129.3 136.2 141.5 150.5 156.4 161.4 171.4 180.6 185.9 119.7 125.5 130.2 135.4 140.5 146.0 152.0 152.0 159.9 170.0 180.9 188.6

7.1 15.4 27.2 46.4 75.5 102.9 151.9 187.6 218.7 298.2 381.2 428.6 4.9 9.9 16.6 27.4 42.7 64.1 91.5 95.7 142.8 217.9 332.8 427.1

0.74 1.44 2.35 3.73 5.68 7.45 10.43 12.54 14.32 18.88 23.51 26.08 0.58 1.07 1.68 2.59 3.81 5.41 7.34 7.68 10.85 15.67 22.83 28.52

1: Calculated from M. Synonym: C. I. Solvent Blue 35 Source: Tuma, D.; Wagner, B.; Schneider, G. M. Fluid Phase Equil. (2001), 182, 133-143. (Another source: Wagner, B. Sc.D. Thesis, University of Bochum, Bochum, Germany, 1998.)

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Solubility Data B

105

[B-42]

1,4-Bis(dodecylamino)anthraquinone (C38H58N2O2; MW=574.88) P (bar)

310.0

100 120 140 160 200 250 300 140 150 160 170 180 200 220 240 260 280 120 130 130 140 140 140 150 150 160 170 170 180 180 190 190 190 200 200 210 220

320.0

330.0

340.0

135 140 145 150 160

Mx y1) x 106 (mol/L) 6.5 0.42 10.9 0.63 15.4 0.86 19.3 1.04 27.2 1.40 50.5 2.48 64.7 3.08 16.9 1.05 22.1 1.33 28.2 1.66 32.8 1.89 37.6 2.12 48.5 2.65 61.2 3.26 67.0 3.50 76.5 3.92 95.0 4.80 1.3 0.12 4.2 0.34 4.5 0.36 9.2 0.68 9.4 0.69 9.4 0.69 16.9 1.17 16.7 1.15 26.0 1.71 37.2 2.37 35.5 2.26 48.8 3.02 47.8 2.95 62.4 3.76 61.4 3.70 59.6 3.59 78.0 4.60 75.5 4.45 87.4 5.07 108.2 6.17 2.7 4.5 6.9 9.6 19.9

310 K 320 K 330 K 340 K

6 y x 106

T (K)

106

4

2

0 50

150

0.25 0.40 0.59 0.79 1.51

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250 P (bar)

350

106

Solubility in Supercritical Carbon Dioxide

170 180 190 200

34.2 54.1 77.2 101.3

2.46 3.72 5.13 6.53

1: Calculated from M. Source: Swidersky, P.; Tuma, D.; Schneider, G. M. J. Supercrit. Fluids (1996), 9, 12-18. (Another source: Swidersky, P. Sc.D. Thesis, University of Bochum, Bochum, Germany, 1994.)

1,4-Bis(ethylamino)anthraquinone (C18H18N2O2; MW=294.35) M x 106 (mol/L)

T (K)

P (bar)

299.3

77.2 87.8 97.9 107.4 117.5 128.1 137.2 147.1 157.0 167.4 177.0 186.9

8.6 11.6 14.1 16.3 18.6 20.8 22.9 24.8 26.9 28.9 30.8 32.6

0.50 0.65 0.77 0.87 0.98 1.08 1.17 1.26 1.35 1.44 1.51 1.59

305.0

76.9 77.0 88.1 98.1 107.9 117.1 126.3 135.2 145.5 155.2 166.0 175.3 185.6 185.6 86.6 96.1 108.0 116.7

3.8 3.5 8.6 11.7 14.9 17.5 20.6 23.0 26.9 28.9 31.7 34.2 37.0 37.4 2.7 7.3 12.2 15.7

0.27 0.25 0.53 0.69 0.85 0.98 1.13 1.24 1.42 1.51 1.63 1.74 1.87 1.89 0.20 0.48 0.75 0.93

310.0

y1) x 106

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[B-43]

Solubility Data B

320.0

325.0

330.0

127.0 137.4 142.0 145.1 146.9 155.0 165.9 175.8 181.4 185.4 97.6 107.4 117.0 127.5 137.0 147.7 157.4 167.2 177.4 186.6 107.4 116.1 127.2 136.9 145.9 146.0 156.9 166.8 176.4 185.9 107.0 117.1 127.2 137.9 147.4 157.0 167.3 177.4 187.5

19.5 23.4 25.5 26.9 27.3 29.8 33.5 37.1 39.4 40.3 3.3 8.0 12.6 17.5 21.9 27.0 31.1 35.5 39.9 43.9 3.6 7.6 13.3 18.4 23.8 24.0 29.6 34.8 40.1 45.2 1.0 4.2 9.1 15.2 21.2 27.4 34.0 40.6 47.2

1.12 1.31 1.42 1.48 1.50 1.62 1.79 1.95 2.06 2.10 0.25 0.54 0.80 1.07 1.30 1.55 1.76 1.97 2.17 2.36 0.28 0.54 0.88 1.16 1.46 1.46 1.75 2.01 2.28 2.53 0.10 0.34 0.66 1.03 1.37 1.71 2.06 2.41 2.74

118.0 128.3 136.0

2.1 6.0 10.0

0.20 0.49 0.76

3 299.3 K 305.0 K 310.0 K 315.0 K 320.0 K 325.0 K 330.0 K 335.0 K 340.0 K 346.0 K

2 y x 106

315.0

107

1

0 50

100

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150 P (bar)

200

108

Solubility in Supercritical Carbon Dioxide

335.0

340.0

346.0

146.1 154.5 154.8 165.9 176.3 186.8 117.5 127.9 137.0 147.5 157.5 166.9 177.1 187.3 126.5 135.9 146.5 157.3 166.0 176.9 186.3

16.3 22.5 22.5 30.3 38.4 46.8 1.0 3.3 6.9 13.0 20.0 27.4 36.1 44.9 1.7 4.2 9.2 16.1 23.1 32.7 42.2

1.14 1.52 1.51 1.95 2.40 2.84 0.11 0.30 0.57 0.99 1.43 1.87 2.37 2.86 0.18 0.39 0.78 1.24 1.69 2.28 2.84

126.0 135.9 145.6 156.2 166.5 176.9 186.9

1.1 2.7 5.9 11.1 18.6 27.9 38.1

0.14 0.29 0.56 0.96 1.48 2.10 2.74

1: Calculated from M. Synonym: C. I. Solvent Blue 105 Source: Tuma, D.; Wagner, B.; Schneider, G. M. Fluid Phase Equil. (2001), 182, 133-143. (Another source: Wagner, B. Sc.D. Thesis, University of Bochum, Bochum, Germany, 1998.)

1,4-Bis(hexadecylamino)anthraquinone (C46H74N2O2; MW=687.09) T (K)

P (bar)

320.0

200 300 400 500 800 900 1000

106

Mx (mol/L)

4.8 10.0 14.1 15.6 18.1 17.5 15.9

y1) x 106 0.26 0.50 0.66 0.71 0.76 0.72 0.64

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[B-44]

Solubility Data B

330.0

12.9 12.5 9.9 8.9 8.6 8.4 1.9 4.9 9.5 13.6 17.2 20.3 22.0 23.4 24.0 24.3 23.6 20.1 19.0 17.6 13.7 12.5 11.7 6.9 17.4 24.0 33.0 37.4 38.7 42.8 46.0 48.9 50.9 51.7 51.9 49.2 46.4 37.6 34.8 29.0 26.6

0.51 0.48 0.38 0.33 0.32 0.31 0.12 0.28 0.50 0.69 0.82 0.90 0.95 0.99 1.00 0.99 0.95 0.80 0.74 0.68 0.52 0.47 0.43 0.41 0.95 1.25 1.66 1.82 1.89 2.00 2.07 2.14 2.18 2.17 2.13 1.99 1.85 1.46 1.34 1.11 1.00

4 320 K 325 K 330 K 340 K

3

y x 106

325.0

1200 1300 1500 1600 1700 1800 150 200 250 300 400 600 700 800 900 1000 1100 1200 1300 1400 1600 1700 1800 200 250 300 350 400 400 500 600 700 800 900 1000 1100 1200 1400 1500 1600 1700

109

2

1

0 0

500

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1000 P (bar)

1500

2000

110

Solubility in Supercritical Carbon Dioxide

340.0

200 225 250 275 300 325

11.8 20.1 28.2 39.5 52.4 65.8

0.76 1.23 1.65 2.23 2.87 3.52

1: Calculated from M. Source: Swidersky, P.; Tuma, D.; Schneider, G. M. J. Supercrit. Fluids (1996), 9, 12-18. (Another source: Swidersky, P. Sc.D. Thesis, University of Bochum, Bochum, Germany, 1994.)

1,4-Bis(isopropylamino)anthraquinone (C20H22N2O2; MW=322.41) P (bar)

305.0

79.1 88.6 102.6 113.6 123.9 138.4 153.3 163.4 177.1 83.6 86.1 92.7 101.1 101.6 111.0 117.6 125.9 131.7 142.0 142.2 152.4 161.7 168.3 91.6 95.3 100.1 110.3 121.0 131.0 140.5 150.5 160.9 165.7

310.0

315.0

Mx (mol/L)

55.0 102.6 157.5 196.8 227.0 279.8 332.1 366.5 407.3 9.9 27.9 70.3 113.1 118.2 163.7 192.6 225.7 253.8 301.0 302.5 347.5 390.2 417.7 9.3 25.8 52.8 110.2 169.5 219.1 270.8 327.5 384.5 409.4

[B-45]

y1) x 106 3.71 6.32 9.11 11.04 12.45 14.96 17.39 18.95 20.75 0.92 2.20 4.79 7.17 7.48 9.89 11.36 12.99 14.40 16.71 16.79 18.94 20.96 22.23 0.90 2.14 3.92 7.33 10.61 13.20 15.86 18.73 21.54 22.74

30

305 K 310 K 315 K 320 K 330 K 340 K

20 y x 106

T (K)

106

10

0 50

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100

150 P (bar)

200

Solubility Data B

111

320.0

6.1 97.1 0.65 19.8 102.1 1.79 64.7 111.1 4.89 123.8 121.0 8.50 196.2 133.0 12.58 252.1 142.0 15.60 327.8 153.3 19.60 407.8 164.2 23.75 330.0 108.5 5.7 0.66 17.6 115.5 1.75 37.3 121.2 3.34 53.6 125.0 4.54 102.3 133.9 7.86 148.2 140.5 10.80 158.0 142.0 11.40 231.1 151.9 15.77 325.1 162.2 21.23 412.2 171.0 26.13 340.0 118.8 7.7 0.93 17.2 125.0 1.88 35.7 132.5 3.51 68.8 140.5 6.14 131.8 151.0 10.65 229.6 162.9 17.14 173.5 24.74 349.8 1: Calculated from M. Synonym: C. I. Disperse Blue 134 Source: Tuma, D.; Wagner, B.; Schneider, G. M. Phys. Chem. Chem. Phys. (2002), 4, 968-973. (Another source: Tuma, D.; Wagner, B.; Schneider, G. M. Fluid Phase Equil. (2001), 182, 133-143.)

1,4-Bis(methylamino)anthraquinone (C16H14N2O2; MW=266.30) T (K) P (bar) 299.0

67.9 68.6 78.7 79.1 88.5 88.6 98.4 108.5 118.0 128.0

106

Mx (mol/L) 6.5 6.4 9.6 9.8 12.1 12.0 14.3 16.6 18.6 20.6

y1) x 106 0.40 0.39 0.55 0.56 0.67 0.67 0.78 0.88 0.97 1.07

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[B-46]

112

310.0

315.0

138.0 148.3 158.0 167.9 178.0 187.4 76.2 76.6 88.3 97.7 108.3 117.7 127.5 137.5 137.6 145.5 156.0 167.2 177.9 187.3 88.0 97.6 107.6 117.6 125.5 126.6 136.0 146.5 147.0 156.5 166.9 175.8 175.9 177.8 180.0 186.9 188.0 98.1 108.0 117.6 127.5 138.1 148.4 156.7 167.5 177.2 187.2

22.6 24.5 26.5 28.5 30.3 32.1 3.0 3.0 8.4 11.5 14.8 17.6 20.3 23.0 23.0 24.9 27.9 30.5 33.2 35.6 3.6 7.9 12.0 15.6 18.5 18.7 21.9 25.4 25.9 29.0 32.5 34.9 35.5 36.0 35.3 38.7 39.1 3.4 8.0 12.3 16.6 21.1 25.5 29.3 33.6 37.4 41.4

1.15 1.24 1.33 1.41 1.49 1.56 0.22 0.21 0.52 0.68 0.84 0.98 1.11 1.23 1.23 1.32 1.45 1.57 1.69 1.80 0.27 0.52 0.73 0.92 1.06 1.07 1.23 1.40 1.43 1.57 1.73 1.84 1.87 1.89 1.85 2.01 2.03 0.26 0.54 0.78 1.01 1.24 1.47 1.65 1.86 2.04 2.22

3

299 K 305 K 310 K 315 K 320 K 325 K 330 K 335 K 340 K 345 K

2 y x 106

305.0

Solubility in Supercritical Carbon Dioxide

1

0 50

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100

150 P (bar)

200

Solubility Data B

320.0

325.0

330.0

335.0

340.0

107.2 117.6 127.9 137.2 137.8 147.0 157.4 164.9 167.0 167.0 168.3 168.4 177.1 185.6 117.4 128.0 137.5 147.2 157.0 167.2 176.4 187.9 117.0 127.4 137.5 146.9 156.9 157.1 167.2 167.2 176.8 187.4 127.7 137.5 147.4 156.6 167.8 177.4 188.1 127.0 137.1 147.0 156.5 167.0 177.3 186.9

113

3.6 8.3 13.2 17.8 18.2 22.6 27.8 31.2 32.5 32.5 32.8 33.0 37.5 42.2 4.2 9.1 13.9 19.5 25.2 31.0 36.4 43.1 1.9 5.4 10.3 15.7 21.9 22.2 28.5 28.8 35.4 42.8 3.1 6.8 11.8 17.6 25.1 32.3 40.6 1.9 4.5 8.6 14.2 21.4 29.5 37.7

0.29 0.58 0.87 1.12 1.14 1.38 1.64 1.81 1.88 1.88 1.89 1.90 2.13 2.36 0.34 0.66 0.95 1.26 1.57 1.88 2.16 2.50 0.18 0.45 0.77 1.10 1.46 1.48 1.83 1.85 2.21 2.60 0.29 0.56 0.89 1.26 1.71 2.12 2.58 0.20 0.41 0.72 1.10 1.56 2.05 2.53

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114

Solubility in Supercritical Carbon Dioxide

345.0

3.0 137.9 0.30 6.3 147.7 0.58 11.0 157.1 0.92 17.7 167.7 1.38 25.6 177.7 1.89 187.9 2.44 34.5 1: Calculated from M. Synonym: C. I. Disperse Blue 14 Source: Kautz, C. B.; Wagner, B.; Schneider, G. M. J. Supercrit. Fluids (1998), 13, 43-47.

1,4-Bis(octadecylamino)anthraquinone (C50H82N2O2; MW=743.21)

340.0

200 250 300 400 500 600 700 800 900 1000 1200 1400 1600 1800 200 250 300 400 500 600 700 800 900 920 920 1000 1200 1400 1600 1800

y1,2) x 106 0.01 0.09 0.14 0.23 0.29 0.31 0.29 0.26 0.22 0.17 0.10 0.07 0.04 0.04 0.04 0.19 0.42 0.87 1.22 1.30 1.30 1.20 0.91 0.87 0.88 0.70 0.47 0.34 0.30 0.29

5 330 K 340 K 345 K 350 K 360 K 380 K 400 K

4

6

330.0

M x 106 (mol/L) 0.2 1.7 2.7 4.8 6.3 6.8 6.6 6.0 5.3 4.1 2.5 1.7 1.1 1.1 0.6 3.3 7.6 17.2 25.3 28.0 28.9 27.5 21.2 20.4 20.7 16.7 11.5 8.7 7.8 7.7

y x 10

T (K) P (bar)

[B-47]

3 2 1 0 0

500

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1000 P (bar)

1500

2000

Solubility Data B

345.0

350.0

360.0

380.0

400.0

200 225 250 300 350 400 500 500 600 700 700 800 900 1000 1200 1400 1600 1800 200 250 300 350 400 637 907 1200 1600 1800 170 185 200 225 250 250 275 300 350 200 200 225 225 250 250 275 275 280 280 300 180 200 220 240

115

1.5 3.4 7.0 13.2 22.0 31.3 42.8 42.8 49.5 49.5 50.1 48.3 41.3 28.8 21.4 16.7 12.9 11.4 0.9 8.6 24.0 43.1 57.4 85.0 83.1 65.0 30.2 17.7 0.1 1.1 3.0 10.3 23.0 23.1 36.6 46.2 64.3 1.2 1.7 4.6 6.0 13.4 15.7 31.1 35.5 40.9 41.7 60.4 0.5 0.9 2.4 5.6

0.10 0.22 0.42 0.74 1.18 1.62 2.09 2.09 2.32 2.25 2.27 2.14 1.78 1.22 0.88 0.67 0.50 0.43 0.06 0.54 1.39 2.36 3.02 3.99 3.62 2.69 1.18 0.68 0.01 0.09 0.24 0.74 1.55 1.55 2.34 2.83 3.70 0.12 0.17 0.40 0.52 1.05 1.23 2.27 2.60 2.95 3.01 4.18 0.07 0.10 0.25 0.53

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116

Solubility in Supercritical Carbon Dioxide

8.2 250 0.75 12.5 260 1.10 24.8 280 2.04 300 3.30 42.2 1: Calculated from M. 2: The solubility values (shown as "x") at 637 and 907 bar at 350 K were obtained from Fig. 2 in the source article, which were calculated using an equation of state. Source: Kraska, T.; Jurtzik, J.; Tuma, D.; Schneider, G. M. Russ. J. Phys. Chem. 77, Suppl. 1 , (2003), S51-S57.

1,4-Bis(octylamino)anthraquinone (C30H42N2O2; MW=462.67)

310.1

90.4 90.4 95.4 95.5 100.1 100.3 100.3 105.7 110.6 115.0 116.0 116.0 120.6 125.9 130.7 135.6 140.7 146.0 150.8 155.7 160.1 164.4 169.6 174.8 180.2 185.1 190.3 195.8

6

M x 10 (mol/L) 7.9 8.1 16.4 16.2 25.5 24.1 24.6 33.0 40.2 47.4 51.0 51.4 57.1 65.8 77.0 86.0 95.3 104.6 113.4 122.2 129.6 137.7 146.8 155.7 165.5 174.1 183.0 192.4

2)

[B-48]

6

y x 10

0.56 0.57 1.09 1.08 1.63 1.54 1.57 2.04 2.44 2.82 3.03 3.05 3.34 3.79 4.38 4.84 5.31 5.77 6.20 6.63 6.98 7.37 7.81 8.22 8.68 9.08 9.49 9.92

20 310.1 K 320.0 K 329.9 K 340.1 K

15

y x 106

T (K) P (bar)

1)

10

5

0 50

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100

150 P (bar)

200

Solubility Data B

320.0

329.9

340.1

100.1 105.4 110.9 115.1 120.6 124.7 130.1 135.5 139.2 140.2 145.2 150.2 160.2 164.8 169.5 169.9 174.5 179.5 185.3 191.9 199.8 106.0 110.0 115.1 120.9 126.6 132.0 136.9 139.1 144.8 150.1 155.6 159.3 165.4 171.3 176.3 180.9 185.0 190.1 115.7 116.2 121.2 121.2 126.2 127.0 130.2 130.7 134.8 135.2 139.3 141.1

117

1.6 6.2 15.1 20.4 31.1 41.4 55.0 69.8 79.8 84.3 99.8 115.6 148.9 164.7 180.6 182.8 199.2 216.4 237.1 260.0 286.3 0.6 1.0 2.9 7.3 15.7 25.0 37.3 44.2 63.3 85.1 109.7 127.2 159.4 192.7 221.6 248.6 272.2 300.9 0.6 0.6 1.1 1.3 2.4 2.5 4.1 4.3 7.1 7.6 11.0 14.4

0.15 0.52 1.15 1.47 2.14 2.77 3.58 4.43 4.99 5.25 6.11 6.97 8.75 9.58 10.40 10.52 11.36 12.23 13.27 14.40 15.67 0.07 0.11 0.29 0.65 1.30 1.95 2.79 3.25 4.48 5.85 7.35 8.39 10.28 12.19 13.81 15.31 16.59 18.12 0.08 0.08 0.13 0.15 0.26 0.27 0.42 0.43 0.68 0.72 1.00 1.28

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118

Solubility in Supercritical Carbon Dioxide

145.9 22.4 1.90 151.1 32.9 2.66 151.3 34.7 2.80 156.3 49.3 3.84 161.9 70.9 5.33 166.6 91.1 6.67 172.3 117.5 8.37 177.2 143.9 10.03 181.9 173.3 11.86 188.2 215.6 14.43 194.8 261.1 17.11 1: Solubility measured using a column packed with Kieselguhr. 2: Calculated from M. Source: Kautz, C. B. Sc.D. Thesis, University of Bochum, Bochum, Germany, 1996.

1,4-Bis(octylamino)anthraquinone (C30H42N2O2; MW=462.67)

320.0

85.3 91.2 95.9 101.1 101.3 106.4 110.8 116.1 117.1 121.1 126.5 132.0 136.8 137.2 142.0 146.9 152.3 157.4 161.8 167.0 167.1 173.1 173.4 177.9 182.9 188.2 193.5 101.1 104.7 110.4 116.2 121.1 124.4

M x 10 (mol/L) 0.9 8.8 16.1 23.4 24.7 32.8 40.1 49.4 50.5 58.1 67.3 77.3 85.6 85.1 94.9 103.9 114.1 123.1 131.4 140.5 140.6 151.9 151.6 159.9 168.8 178.1 187.9 1.5 3.7 11.0 21.5 32.0 39.3

2)

[B-49]

6

y x 10

0.08 0.62 1.07 1.49 1.58 2.03 2.43 2.94 2.99 3.40 3.88 4.40 4.82 4.78 5.28 5.73 6.23 6.67 7.07 7.51 7.51 8.05 8.03 8.42 8.84 9.27 9.72 0.14 0.31 0.84 1.54 2.20 2.64

20 310.3 K 320.0 K 330.0 K 340.1 K

15 6

310.3

6

y x 10

T (K) P (bar)

1)

10

5

0 50

100

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150 P (bar)

200

Solubility Data B

330.0

340.1

125.3 129.7 135.0 140.5 145.3 145.4 150.3 155.8 161.4 166.3 171.6 176.5 181.3 186.8 191.1 110.0 114.4 115.3 120.5 121.0 124.9 124.9 125.9 130.1 130.7 134.9 135.6 139.6 140.5 145.9 150.7 155.7 161.1 161.7 165.5 170.5 176.2 180.8 186.5 120.5 126.6 126.9 131.4 136.1 141.4 146.7 151.5 151.9 156.5 161.1 166.1 171.1

119

42.9 54.5 69.6 87.1 102.1 100.8 117.4 136.0 155.5 172.8 191.8 209.4 226.8 246.0 261.1 0.7 1.6 2.0 5.5 6.0 10.1 10.2 11.9 18.6 20.7 30.1 31.7 44.4 46.0 65.5 85.5 108.6 143.3 144.6 164.6 192.4 225.2 252.3 286.1 0.7 2.0 2.0 3.9 7.5 13.5 22.4 31.9 34.6 46.8 63.1 84.6 109.3

2.86 3.55 4.42 5.42 6.25 6.17 7.08 8.08 9.11 10.02 11.00 11.90 12.78 13.73 14.48 0.08 0.16 0.20 0.50 0.54 0.86 0.87 1.00 1.48 1.64 2.29 2.40 3.26 3.35 4.61 5.87 7.28 9.40 9.46 10.62 12.21 14.06 15.55 17.39 0.08 0.21 0.21 0.39 0.70 1.19 1.88 2.57 2.78 3.64 4.77 6.21 7.83

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120

Solubility in Supercritical Carbon Dioxide

176.4 139.0 9.72 181.6 170.2 11.66 188.7 218.0 14.57 196.4 273.6 17.85 196.8 275.1 17.93 1: Solubility measured using a column packed with Chromosorb G-AW. 2: Calculated from M. Source: Kautz, C. B. Sc.D. Thesis, University of Bochum, Bochum, Germany, 1996.

1,4-Bis(octylamino)anthraquinone (C30H42N2O2; MW=462.67)

298.4

80 84 89 90 94 100 106 112 118 125 131 137 148 155 162 168 174 180 186 192 200 78 81 85 89 94 100 105 110 115 117 120 125 127 135 142 148 154

M x 10 (mol/L) 23.4 24.6 25.9 30.6 33.4 35.2 36.7 38.2 39.3 41.1 42.9 44.2 48.4 50.5 52.0 53.5 55.1 56.3 58.4 60.3 61.3 29.4 31.5 32.6 33.9 36.1 38.3 40.4 43.3 46.7 48.3 49.6 51.6 53.1 56.7 60.6 63.9 66.8

2)

[B-50]

6

y x 10

1.25 1.30 1.36 1.60 1.74 1.82 1.87 1.94 1.98 2.05 2.13 2.18 2.36 2.45 2.51 2.57 2.64 2.68 2.77 2.85 2.88 1.73 1.78 1.82 1.88 1.97 2.07 2.16 2.29 2.45 2.52 2.59 2.67 2.74 2.90 3.07 3.22 3.34

9 293.6 K 298.4 K 303.2 K 306.9 K 308.7 K 310.1 K 314.2 K 315.7 K 324.7 K

6 6

293.6

6

y x 10

T (K) P (bar)

1)

3

0 50

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100

150 P (bar)

200

Solubility Data B

303.2

306.9

72 77 79 80 83 87 90 91 92 95 97 100 103 105 107 109 110 112 115 120 125 128 131 134 82 85 89 93 93 97 97 100 103 106 109 110 112 113 115 116 118 119 121 123 125 126 128 128 129 132 135 138

121

4.5 12.3 15.6 20.2 22.4 25.3 29.4 29.7 31.0 33.2 34.8 37.4 44.8 44.0 47.6 49.2 48.5 51.6 52.0 56.9 61.6 64.6 67.3 69.8 11.1 14.6 20.0 25.3 25.3 30.1 30.2 34.1 38.2 42.3 46.2 51.7 50.6 53.9 54.6 56.6 58.5 59.6 62.4 66.5 67.1 69.3 71.3 71.4 72.6 77.1 80.8 83.6

0.54 0.79 0.99 1.26 1.37 1.52 1.74 1.75 1.82 1.92 2.00 2.13 2.53 2.47 2.66 2.74 2.69 2.85 2.85 3.09 3.32 3.46 3.59 3.71 0.79 0.98 1.28 1.58 1.58 1.84 1.84 2.05 2.27 2.49 2.69 3.00 2.92 3.10 3.12 3.23 3.32 3.37 3.51 3.72 3.74 3.85 3.95 3.96 4.02 4.24 4.42 4.54

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122

308.7

310.1

Solubility in Supercritical Carbon Dioxide

138 138 141 144 147 150 153 156 159 163 166 170 170 72 84 88 93 97 100 103 105 107 110 113 113 115 118 121 124 126 88 91 92 93 94 95 95 96 98 100 103 106 110 113 116 119 122 125 128

84.1 84.7 88.0 91.7 95.4 98.5 102.3 106.0 110.2 119.0 122.3 127.4 127.7 0.0 4.6 11.2 18.3 25.1 30.2 35.4 38.4 41.3 48.0 51.8 50.2 55.0 60.9 65.1 71.0 74.4 5.9 7.1 11.6 13.3 15.5 15.6 15.6 17.8 20.5 24.5 29.4 35.1 41.0 47.9 53.3 59.4 64.3 70.7 75.4

4.57 4.61 4.76 4.94 5.11 5.26 5.43 5.61 5.81 6.24 6.39 6.62 6.64 0.00 0.35 0.77 1.20 1.59 1.88 2.17 2.33 2.49 2.85 3.05 2.95 3.22 3.53 3.74 4.05 4.22 0.44 0.50 0.80 0.90 1.04 1.04 1.04 1.18 1.33 1.57 1.85 2.17 2.49 2.88 3.16 3.49 3.75 4.08 4.32

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Solubility Data B

314.2

315.7

89 89 93 96 99 101 104 107 109 110 112 113 113 115 116 118 119 121 122 124 125 128 131 134 138 142 145 145 148 150 85 89 95 100 105 108 110 111 113 114 115 116 117 118 119 120 121 121 121 122 124 126

123

1.2 1.2 5.5 9.0 14.3 18.2 23.8 29.8 33.8 39.4 40.0 43.3 43.3 45.4 49.1 51.5 55.7 58.7 61.3 65.0 67.7 73.8 80.5 86.9 96.1 106.7 116.2 115.9 122.5 127.9 1.0 1.4 6.4 12.3 21.4 27.9 30.3 34.0 37.3 40.4 44.8 45.3 46.0 50.0 51.0 55.0 60.2 56.5 55.5 59.0 63.5 67.9

0.13 0.13 0.46 0.70 1.05 1.30 1.64 2.00 2.23 2.58 2.58 2.78 2.78 2.89 3.10 3.23 3.48 3.63 3.77 3.97 4.12 4.44 4.80 5.14 5.62 6.17 6.67 6.66 6.99 7.27 0.15 0.16 0.56 0.95 1.52 1.93 2.05 2.29 2.47 2.66 2.93 2.95 2.98 3.21 3.26 3.50 3.81 3.58 3.51 3.72 3.97 4.21

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124

Solubility in Supercritical Carbon Dioxide

324.7

93 0.4 0.06 96 0.5 0.06 99 0.7 0.08 102 1.2 0.13 105 2.3 0.24 108 3.5 0.34 111 6.5 0.58 113 9.4 0.81 115 12.8 1.07 117 16.3 1.32 118 18.1 1.45 118 17.9 1.43 120 22.2 1.73 122 26.7 2.03 124 31.6 2.36 125 35.1 2.59 126 36.9 2.70 128 42.7 3.07 129 45.4 3.24 130 48.6 3.45 131 51.9 3.65 132 54.5 3.81 134 61.3 4.23 137 71.1 4.82 140 82.0 5.47 143 92.6 6.09 145 103.9 6.77 145 102.9 6.71 147 107.9 6.97 150 121.9 7.79 152 133.8 8.49 1: Measured with two different UV/Vis spectrometers. 2: Calculated from M. Source: Tuma, D.; Schneider, G. M. J. Supercrit. Fluids (1998), 13, 37-42.

1,4-Bis(octylamino)anthraquinone (C30H42N2O2; MW=462.67) T (K) P (bar) 285.9

60 70 80 85 90 100 110 115 125 130 130

1)

6

M x 10 (mol/L) 13.1 14.5 16.7 17.2 19.1 20.9 22.1 22.6 24.3 24.7 25.1

2)

6

y x 10

0.67 0.73 0.83 0.85 0.94 1.02 1.07 1.08 1.16 1.17 1.19

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[B-51]

Solubility Data B

288.8

291.0

1.29 1.34 1.49 1.44 1.46 1.58 1.59 1.64 1.64 1.71 1.72 1.79 1.86 1.91 2.04 2.06 2.10 2.12 2.14 2.15 2.17 2.17 2.18 2.18 2.18 2.18 1.28 1.36 1.43 1.56 1.62 1.66 1.71 1.77 1.83 1.89 1.95 2.03 2.15 2.23 2.27 2.32 2.48 2.71 1.00 1.12 1.26 1.38 1.51 1.56

12

285.9 K 288.8 K 291.0 K 296.0 K 303.2 K

8 6

27.6 28.9 32.4 31.6 31.9 34.9 35.0 36.5 36.6 38.5 38.7 40.7 42.6 44.3 47.8 48.9 50.4 51.6 52.6 53.4 54.2 54.8 55.4 55.8 56.3 56.8 25.4 27.7 29.3 32.5 33.9 35.2 36.4 37.9 39.5 40.7 42.5 44.6 47.8 49.8 51.1 52.7 56.9 62.8 19.0 21.6 24.6 27.4 30.3 31.7

y x 10

150 160 175 190 190 200 200 225 225 250 250 275 300 325 360 400 450 500 550 600 650 700 750 800 850 900 90 110 117 135 145 155 165 175 185 185 200 220 240 260 280 300 325 350 70 80 90 100 110 120

125

4

0 0

400

CAT4240—CHAPTER 2—31/10/2006—18:28—MUGUNTHAN—XML MODEL C – pp. 75–149

800 P (bar)

1200

126

296.0

Solubility in Supercritical Carbon Dioxide

125 130 140 155 170 185 200 215 230 250 270 290 310 330 350 375 400 425 450 475 500 500 500 530 570 620 670 720 770 820 85 90 97 97 105 111 115 117 117 120 123 125 129 130 135 138 138 140 145

34.3 33.8 36.1 40.3 43.1 46.4 49.4 52.3 55.0 59.5 61.8 64.5 67.1 69.6 72.0 75.6 77.1 78.6 80.2 81.7 83.0 80.8 81.3 84.4 84.2 85.6 86.8 88.1 89.0 90.0 30.2 30.7 32.9 33.3 37.1 40.1 45.0 43.2 43.4 46.6 46.2 47.5 48.9 49.3 51.6 52.7 52.9 53.6 55.3

1.68 1.65 1.75 1.93 2.04 2.17 2.30 2.41 2.51 2.69 2.77 2.87 2.96 3.05 3.13 3.26 3.30 3.34 3.39 3.43 3.46 3.37 3.39 3.49 3.46 3.48 3.49 3.52 3.52 3.54 1.64 1.65 1.74 1.76 1.94 2.07 2.31 2.22 2.22 2.38 2.35 2.41 2.47 2.49 2.59 2.64 2.65 2.68 2.75

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Solubility Data B

303.2

150 155 160 167 175 180 185 193 200 207 215 222 230 237 245 253 260 268 275 283 290 298 305 315 325 79 83 87 91 95 99 103 107 111 115 120 130 135 140 145 150 155 160 165 170 175 175 185 195 200 205

127

57.5 59.4 61.8 66.0 68.8 70.6 72.6 74.9 77.9 80.7 83.4 85.9 90.5 91.9 93.6 96.5 99.0 101.2 102.8 104.6 106.6 111.1 112.4 114.7 118.0 14.0 18.1 22.6 26.6 30.6 35.4 40.0 44.0 47.0 50.8 55.7 66.0 69.1 72.5 76.2 82.9 85.6 89.8 94.6 97.5 100.1 97.5 104.8 112.6 122.8 121.8

2.84 2.93 3.03 3.21 3.33 3.41 3.49 3.58 3.71 3.82 3.93 4.03 4.23 4.27 4.33 4.45 4.55 4.63 4.69 4.76 4.83 5.01 5.06 5.14 5.27 0.88 1.11 1.35 1.56 1.77 2.02 2.26 2.46 2.60 2.79 3.03 3.52 3.66 3.81 3.98 4.30 4.41 4.61 4.82 4.95 5.05 4.92 5.24 5.58 6.06 5.99

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128

Solubility in Supercritical Carbon Dioxide

220 131.8 6.41 230 138.5 6.69 260 150.5 7.13 290 165.9 7.73 320 181.3 8.33 350 196.5 8.91 390 210.1 9.38 430 221.8 9.77 470 234.7 10.20 510 242.9 10.44 550 251.8 10.71 600 262.0 11.01 650 266.6 11.08 700 271.0 11.15 750 277.5 11.31 800 280.6 11.34 850 283.1 11.34 900 285.1 11.33 950 284.6 11.23 1000 288.8 11.31 1100 292.3 11.30 1: Measured with three different UV/Vis spectrometers. 2: Calculated from M. Source: Tuma, D.; Schneider, G. M. J. Supercrit. Fluids (1998), 13, 37-42.

1,4-Bis(pentylamino)anthraquinone (C24H30N2O2; MW=378.51) T (K) P (bar) 299.0

305.0

65.6 66.6 77.6 87.2 97.6 107.2 116.9 127.2 137.4 147.0 157.8 167.4 177.4 187.4 77.5 87.0 96.1 96.3 107.0 117.5 127.2 137.0 147.2

6

M x 10 (mol/L) 41.6 46.7 76.4 100.8 125.1 146.4 168.1 189.5 211.3 230.4 244.3 264.1 285.3 303.1 24.4 65.6 99.1 98.0 133.9 167.1 196.7 225.1 248.3

1)

6

y x 10

2.63 2.91 4.42 5.64 6.82 7.83 8.84 9.82 10.81 11.66 12.22 13.09 14.02 14.77 1.71 4.08 5.87 5.81 7.65 9.29 10.72 12.07 13.11

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[B-52]

Solubility Data B

320.0

330.0

250.0 279.8 310.1 340.4 371.0 7.6 10.2 16.7 19.0 22.4 24.2 45.2 67.4 71.1 89.0 101.3 129.7 149.3 168.4 187.7 207.8 231.5 247.5 269.7 301.0 315.1 334.4 359.4 380.9 402.8 418.4 439.2 11.7 25.4 45.8 64.3 69.8 95.7 123.9 150.5 181.4 240.3 299.7 299.8 373.8 405.9 439.1 4.6 11.1 23.6 39.8

13.19 14.58 15.98 17.35 18.71 0.65 0.84 1.30 1.47 1.68 1.81 3.10 4.40 4.62 5.61 6.27 7.80 8.82 9.82 10.80 11.80 12.98 13.71 14.82 16.35 17.03 17.95 19.15 20.16 21.18 21.87 22.83 1.05 2.05 3.42 4.60 4.95 6.52 8.18 9.69 11.44 14.63 17.76 17.76 21.62 23.26 24.93 0.49 1.08 2.09 3.29

30

299 K 305 K 310 K 320 K 330 K 340 K

20 y x 106

310.0

147.4 157.0 166.4 176.4 186.9 84.5 85.1 86.4 86.5 87.5 87.6 92.1 97.1 97.6 102.3 105.5 112.0 117.1 121.2 126.0 131.1 137.1 143.0 147.5 154.4 157.5 162.4 167.7 172.4 177.9 182.8 187.5 102.6 107.0 112.0 115.9 116.9 122.1 127.0 132.0 136.9 147.0 156.8 156.9 167.2 171.9 176.9 111.5 116.6 122.0 126.9

129

10

0 50

100

CAT4240—CHAPTER 2—31/10/2006—18:28—MUGUNTHAN—XML MODEL C – pp. 75–149

P (bar)

150

200

130

Solubility in Supercritical Carbon Dioxide

61.1 131.7 4.79 88.7 137.0 6.64 120.8 142.2 8.70 152.8 147.0 10.69 188.1 151.7 12.84 222.8 156.5 14.88 262.3 162.3 17.12 301.8 166.4 19.42 344.3 170.5 21.86 402.3 176.5 25.09 438.1 180.4 27.03 340.0 122.0 4.6 0.53 8.5 126.1 0.91 27.9 136.4 2.61 64.2 146.1 5.41 127.1 156.9 9.84 121.3 157.9 9.34 198.1 166.4 14.50 286.8 176.3 20.05 373.9 183.9 25.37 186.9 27.83 414.4 1: Calculated from M. Synonym: C. I. Solvent Blue 14 Source: Tuma, D.; Wagner, B.; Schneider, G. M. Fluid Phase Equil. (2001), 182, 133-143. (Another Source: Wagner, B. Sc.D. Thesis, University of Bochum, Bochum, Germany, 1998.)

1,4-Bis(prop-2'-enyloxy)anthraquinone1) (C20H16O4; MW=320.34) T (K) P (bar) 308.15 121.6 162.1 202.7 243.2 283.7 324.2 364.8

S (g/L) 0.37 0.52 0.66 0.84 0.98 1.05 1.17

y2) x 106 66 87 105 129 145 153 167

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[B-53]

Solubility Data B

131

29 48 69 90 107 130 144 159 29 60 85 124 161 190 220 8 76 117 128 158 200 2 39 100 116 138 140

0.14 0.27 0.41 0.56 0.69 0.86 0.97 1.09 0.11 0.30 0.47 0.73 0.98 1.20 1.42 0.02 0.33 0.59 0.70 0.92 1.20 0.01 0.15 0.46 0.59 0.75 0.80

250

200

150

308 K 318 K 328 K 338 K 348 K

y x 106

318.15 121.6 162.1 202.7 243.2 283.7 324.2 364.8 405.3 328.15 121.6 162.1 202.7 243.2 283.7 324.2 364.8 338.15 121.6 162.1 202.7 243.2 283.7 324.2 348.15 121.6 162.1 202.7 243.2 283.7 324.2

100

50

0 100

200

300 P (bar)

400

1: In the source table the compound was named 1,8Bis(prop-2'-enyloxy)anthraquinone, but it must be 1,4Bis(prop-2'-enyloxy)anthraquinone as the authors synthesized it from 1,4-Dihydroxyanthraquinone. Figure 1 in the source also shows this 1,4- form. 2: Some of the y values did not agree with S and thus were re-calculated based on S (The corrected values are in italics). Synonym: 1,4-Bis(allyloxy)anthraquinone Source: Fat'hi, M. R.; Yamini, Y.; Sharghi, H.; Shamsipur, M. J. Chem. Eng. Data (1998), 43(3), 400-402.

1, 8-Bis(prop-2'-enyloxy)anthraquinone (C20H16O4; MW=320.34) T(K) P(bar) 318.15 122 162 203 243 284 324 365

S

(g/m3) 18 24 27 36 42 46 49

yx

106 3.7 4.3 4.5 5.8 6.5 7.0 7.3

CAT4240—CHAPTER 2—31/10/2006—18:28—MUGUNTHAN—XML MODEL C – pp. 75–149

[B-54]

132

338.15

348.15

162 203 243 284 324 365 405 122 162 203 284 324 365 405 122 162 203 243 284 324 365 405

40 49 53 57 63 77 83 12 40 77 96 122 148 161 12 32 94 148 199 266 287 328

8.0 8.9 9.0 9.3 10.0 11.9 12.5 4.2 9.1 15.1 16.6 20.2 23.8 25.2 5.0 8.5 20.3 28.9 36.3 46.3 48.1 53.3

60

40 y x 106

328.15

Solubility in Supercritical Carbon Dioxide

318 K 328 K 338 K 348 K

20

0 100

200

300 P (bar)

400

1: The y values in the original article did not agree with S values (one order of magnitude larger than those expected) and thus were re-calculated based on S. Synonym: 1,8-Bis(allyloxy)anthraquinone Source: Fat'hi, M. R.; Yamini, Y.; Sharghi, H.; Shamsipur, M. Talanta (1999), 48(4), 951-957.

1,4-Bis(propylamino)anthraquinone (C20H22N2O2; MW=322.41) T (K) P (bar) 305.0

310.0

78.7 90.0 100.9 109.5 124.1 140.0 154.4 170.0 187.9 84.1 89.5 95.6 100.0 114.9 115.0 123.1 129.7 140.6 150.9 150.9

M x 106 (mol/L) 31.5 69.1 98.0 122.6 157.8 192.4 223.7 255.9 288.9 8.7 37.5 59.1 83.4 138.8 139.3 173.8 191.7 226.9 246.6 245.9

y1) x 106 2.14 4.22 5.71 6.95 8.65 10.27 11.69 13.13 14.56 0.77 2.68 3.91 5.33 8.26 8.28 10.08 10.93 12.63 13.48 13.44

CAT4240—CHAPTER 2—31/10/2006—18:28—MUGUNTHAN—XML MODEL C – pp. 75–149

[B-55]

Solubility Data B

320.0

330.0

289.0 288.7 306.1 304.1 328.3 346.2 6.0 12.9 21.4 42.7 69.7 109.3 107.8 147.6 183.3 221.0 257.1 289.4 290.3 319.1 344.1 10.7 22.3 42.0 63.3 87.1 131.3 176.4 224.1 269.2 309.7 340.6 351.0 7.9 15.0 30.3 49.7 61.1 76.4 108.2 156.5 216.7 278.3 331.7 355.0

15.54 15.42 16.25 16.14 17.20 17.95 0.57 1.09 1.69 3.06 4.66 6.88 6.79 8.93 10.76 12.67 14.44 15.98 16.03 17.34 18.45 0.98 1.85 3.19 4.55 6.00 8.50 10.98 13.49 15.81 17.80 19.25 19.72 0.82 1.42 2.62 4.01 4.82 5.81 7.85 10.78 14.25 17.67 20.47 21.39

25 305 K 310 K 315 K 320 K 330 K 340 K

20 15

y x 106

315.0

161.0 165.4 170.4 170.5 180.9 189.9 92.1 94.6 97.0 102.6 109.5 119.6 119.8 129.5 139.5 149.6 159.5 169.4 169.5 179.8 189.4 101.6 105.4 111.0 115.5 120.5 131.0 140.5 150.9 160.5 170.5 179.4 182.9 113.4 118.0 123.5 129.0 131.1 135.1 141.1 150.0 160.4 170.5 180.3 190.3

133

10 5 0 50

100

CAT4240—CHAPTER 2—31/10/2006—18:28—MUGUNTHAN—XML MODEL C – pp. 75–149

P (bar)

150

200

134

Solubility in Supercritical Carbon Dioxide

340.0

3.8 119.0 0.45 9.4 124.1 1.04 15.9 129.5 1.62 42.0 139.5 3.79 76.0 147.6 6.32 73.9 147.7 6.14 89.0 150.4 7.23 90.2 150.5 7.33 147.4 160.7 11.15 211.8 169.9 15.23 212.8 170.2 15.29 291.8 180.8 20.03 189.8 23.43 352.4 1: Calculated from M. Source: Wagner , B.; Kautz, C.B.; Schneider, G. M. Fluid Phase Equil. (1999), 158-160, 707-712.

1,1-Bis(4-chlorophenyl)-2,2,2-trichloroethane1 (C14H95Cl; MW=354.49) Water2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 saturated saturated saturated saturated saturated saturated

y3) x 106 178 304 414 515 593 662 41 200 365 533 655 817 12 98 265 489 704 899 194 328 429 544 622 667

1200

800 y x 106

T (K) P (bar) 313.1 104.4 125.1 145.8 166.5 187.2 207.9 323.1 104.4 125.1 145.8 166.5 187.2 207.9 333.1 104.4 125.1 145.8 166.5 187.2 207.9 313.1 104.4 125.1 145.8 166.5 187.2 207.9

[B-56]

CO2 313.1 K CO2 323.1 K CO2 333.1 K Water 313.1 K Water 323.1 K Water 333.1 K

400

0 100

CAT4240—CHAPTER 2—31/10/2006—18:29—MUGUNTHAN—XML MODEL C – pp. 75–149

150 P (bar)

200

Solubility Data B

135

323.1

104.4 saturated 50 125.1 saturated 233 145.8 saturated 421 166.5 saturated 617 187.2 saturated 725 207.9 saturated 875 333.1 104.4 saturated 14 125.1 saturated 116 145.8 saturated 312 545 166.5 saturated 187.2 saturated 763 207.9 saturated 984 1: Used as a pesticide. 2: Cosolvent in CO2. 3: Obtained by digitizing the graph in the original article. Synonyms: DDT; 4,4'-DDT; 1,1,1-Trichloro-2,2bis(4-chlorophenyl)ethane Source: Macnaughton, S. J.; Foster, N. R. Ind. Eng. Chem. Res. (1994), 33(11), 2757-2763.

Bitumen1)

[B-57] 106

25000 20000

w x 106

T (K) P (bar) w x 323.35 40.1 390 79.9 580 119.9 8800 160.1 19000 373.35 40.0 1000 80.0 810 120.0 1400 160.4 4400 473.75 40.1 10300 80.0 10400 119.9 11600 160.4 14300 523.15 40.0 21600 80.0 21900 119.9 22500 1: Cold Lake bitumen from Esso Resources Canada. Source: Yu, J. M.; Huang, S. H.; Radosz, M. Fluid Phase Equil. (1989), 53, 429-438.

323.4 K 373.4 K 473.8 K 523.2 K

15000 10000 5000 0 0

CAT4240—CHAPTER 2—31/10/2006—18:29—MUGUNTHAN—XML MODEL C – pp. 75–149

100 P (bar)

200

136

Solubility in Supercritical Carbon Dioxide

Bitumen1)

[B-58] 30000

w x 106

T (K) P (bar) w x 106 318.15 72.1 1200 85.5 2530 97.4 7210 111.8 14800 124.3 19900 139.0 25200 328.15 73.6 1300 85.1 1950 97.1 2900 112.5 7120 122.5 12000 139.1 21200 1: Volatile components were extracted from Peace River bitumen (Canada). Source: Han, B.; Peng, D. Y.; Fu, C. T.; Vilcsak, G. Can. J. Chem. Eng.(1992), 70(6), 1164-1171.

318.2 K 328.2 K

20000

10000

0 50

100 P (bar)

Bitumen Cut 11) (MW=201) 323.5

373.4

473.7

523.2

P (bar) 40.1 79.9 120.1 161.1 40.0 79.9 119.9 160.8 40.1 79.9 119.9 160.4 40.1 80.0 119.9

wx

[B-59]

106

1940 2540 49300 123000 3130 4300 8150 20500 41400 35600 39800 51200 107000 85000 88400

150000

323.5 K 373.4 K 473.7 K 523.2 K

100000 w x 106

T (K)

150

50000

0

0

1: One of the five fractions obtained from distillation of Cold Lake bitumen made by Esso Resources Canada. Source: Huang, S. H.; Radosz, M. Fluid Phase Equil. (1990), 60(1-2), 81-98.

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100 P (bar)

200

Solubility Data B

137

Bitumen Cut 21) (MW=304) w x 106 1100 970 7700 21000 880 650 1100 3200 7700 6200 7000 11000 25000 20000 22400

30000

w x 106

T (K) P (bar) 323.3 40.0 80.3 120.3 161.2 373.3 40.0 80.5 120.5 161.2 473.5 40.4 79.8 119.6 161.2 523.4 39.9 80.4 120.2

[B-60]

20000 323.3 K 373.3 K 473.5 K 523.4 K

10000

0

0

100 P (bar)

200

1: One of the five fractions obtained from distillation of Cold Lake bitumen made by Esso Resources Canada. Source: Huang, S. H.; Radosz, M. Fluid Phase Equil. (1990), 60(1-2), 81-98.

Bitumen Cut 31) (MW=572) wx

200 100 300 1000 100 100 100 200 100 200 300 600 500 700 1000

1200 323.3 K 373.3 K 473.7 K 523.2 K

800 w x 106

T (K) P (bar) 323.3 40.1 79.9 119.9 161.1 373.3 40.1 80.0 119.9 160.4 473.7 40.1 80.0 119.9 160.4 523.2 40.0 79.9 119.9

[B-61]

106

400

0

0

1: One of the five fractions obtained from distillation of Cold Lake bitumen made by Esso Resources Canada. Source: Huang, S. H.; Radosz, M. Fluid Phase Equil. (1990), 60(1-2), 81-98.

CAT4240—CHAPTER 2—31/10/2006—18:29—MUGUNTHAN—XML MODEL C – pp. 75–149

100 P (bar)

200

138

Solubility in Supercritical Carbon Dioxide

Blackcurrant1) seed oil W (g/kg) 0.51 1.33 3.02 5.46 6.49 0.59 2.38 4.86 6.74 0.87 1.46 3.92 5.90

x

106

510 1330 3010 5430 6450 590 2370 4840 6700 870 1460 3910 5870

8000 6000 w x 106

T (K) P (bar) 313.15 120 150 200 250 280 323.15 150 200 250 280 333.15 180 200 250 280

[B-62] w2)

4000

313 K 323 K 333 K

2000 0 100

1: Tibes nigrum obtained from Czech Republic. 2: Calculated from W. Source: Sovova, H.; Zarevucka, M.; Vacek, M.; Stransky, K. J. Supercrit. Fluids (2001), 20(1), 15-28.

150

200 P (bar)

Black pepper1) essential oil T (K)

P (bar)

W (g/kg CO2)

w1) x 106

300

[B-63] 150000 303 K 313 K 323 K

303.15

w x 106

150 89.0 81700 200 112.9 101400 300 144.4 126200 313.15 150 93.2 85300 200 104.4 94500 300 136.5 120100 323.15 150 85.8 79000 200 99.5 90500 300 125.5 111500 1: Piper nigrum L. produced in Brazil. 2: Calculated from W. Source: Ferreira, S. R. S.; Nikolov, Z. L.; Doraiswamy, L. K.; Meireles, M. A. A.; Petenate, A. J. J. Supercrit. Fluids (1999), 14(3), 235-245.

250

100000

50000 100

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200 P (bar)

300

Solubility Data B

139

(S)-Boc-Piperazine (C14H27N3O3; FW=285.39) y x 10

6000

6

1370 2440 2930 2320 2810 2310 2540 2250 1140 2850 4000 5090 5720 178 241 946 1180 2460 3670 4810 6520

y x 10

T (K) P (bar) 308.2 90.1 109 138 155 167 184 195 205 318.2 106 125 143 182 202 328.2 103 108 123 129 143 164 182 201

[B-64]

6

308.2 K 318.2 K 328.2 K

4000

2000

0

50

100

150 P (bar)

200

Synonym: (S)-tert-butyl 3-(tertbutylcarbamoyl)piperazine-1-carboxylate Source: Uchida, H.; Usui, I.; Fuchita, A.; Matsuoka, M. J. Chem. Eng. Data (2004), 49(6), 1560-1564.

rac-Boc-Piperazine1) (C14H27N3O3; MW=285.39)

[B-65]

y x 106

308.2 K 318.2 K 328.2 K

y x 106

T (K) P (bar) 308.21 03 124 600 114 191 135 173 152 212 171 238 200 223 400 318.2 102 67 105 98 125 249 145 313 200 165 298 187 351 204 460 328.2 104 42 124 104 0 145 300 100 165 348 184 539 204 590 1: An equimolar mixture of (S)- and (R)-Boc-Piperazines. Source: Uchida, H.; Usui, I.; Fuchita, A.; Matsuoka, M. J. Chem. Eng. Data (2004), 49(6), 1560-1564.

CAT4240—CHAPTER 2—31/10/2006—18:29—MUGUNTHAN—XML MODEL C – pp. 75–149

150 P (bar)

200

140

Solubility in Supercritical Carbon Dioxide

Brassylic acid (C13H24O4; MW=244.33)

[B-66]

y x 106 T (K) P (bar) 328.2 150.5 27.6 364.0 127.0 343.2 150.5 23.2 364.0 221.0 Synonym: Tridecanedioic acid Source: Schmitt, W. J.; Reid, R. C. Chem. Eng. Comm. (1988), 64, 155176.

y x 106

250 328.2 K 343.2 K

125

0 100

200

P (bar)

300

[B-67]

Bromobenzene (C6H5Br; MW=157.01) y x 106

50000 313.2 K

40000 6

1900 2600 2500 3300 2900 3500 3800 5400 5500 5400 6700 9000 9400 15600 15900 38400 40400 14600 14800 15100 15200 17200 17300 21900 21100 20300 27900 26900 35400 36400

y x 10

T (K) P (bar) 313.2 62.9 66.9 66.9 70.9 70.9 75.6 75.9 353.1 60.6 60.5 60.5 80.9 100.9 100.9 120.8 120.8 140.8 141.8 393.2 60.4 60.9 80.9 80.9 100.9 100.9 120.9 120.9 120.9 140.9 140.9 160.8 160.8

400

353.1 K 393.2 K

30000 20000 10000 0

50

90

Source: Walther, D.; Maurer, G. Ber. Bunsenges. Phys. Chem. (1992), 96(8), 981-988.

CAT4240—CHAPTER 2—31/10/2006—18:29—MUGUNTHAN—XML MODEL C – pp. 75–149

P (bar)

130

170

Solubility Data B

141

n-Butanol (C4H10O; MW=74.12) T(K)

P(bar)

[B-68]

y x 106 6

y x 10

345 144000 552 174000 690 144000 Synonym: Butyl alcohol Source: Eissier, R.; Friedrich, J. P. J. Am. Oil Chem. Soc. (1988), 65(5), 764-767.

200000

325.15

100000 300

500 P (bar)

700

n-Butanol (C4H10O; MW=74.12) [B-69]

313.15 K 383.15 K

y x 10

6

T (K) P (bar) y x 106 313.15 28.4 3000 42.1 1000 200000 55.2 3000 69.6 6000 78.8 12000 150000 80.3 12000 88.9 32000 89.3 33000 100000 383.15 20.3 95000 32.5 75000 50000 50.2 63000 70.2 58000 90.7 54000 0 99.7 52000 0 120.4 51000 142.0 52000 153.6 65000 154.0 88000 165.0 168000 Synonyms: 1-Butanol; Butyl alcohol Source: King, M. B.; Alderson, D. A.; Fallah, F. H.; Kassim, D. M.; Sheldon, J. R.; Mahmud, R. S. in Chapter 2, Chemical Engineering at Supercritical Fluid Conditions, Paulaitis, M. E.; Penninger, J. M. L.; Gray, Jr., R. D.; Davidson, P. (Eds.) Ann Arbor Science, 1983, pp.31-80.

50

CAT4240—CHAPTER 2—31/10/2006—18:29—MUGUNTHAN—XML MODEL C – pp. 75–149

100 P (bar)

150

200

142

Solubility in Supercritical Carbon Dioxide

n-Butanol(1) + n-Octane(2) Mixture y1 X 10 Y1 383.15 40.2 71.7 99.0 130.3 140.6 Y1 41.8 70.7 102.1 129.4

y2 X 10

0.35 0 23400 22050 23800 41820

69000 41600 40950 46200 81180

0.55 0 36960 36480 33280

75000 29040 27520 30720

100000 But, Y1=0.35 But, Y1=0.55 But, Y1=0.75 Oct, Y1=0.35 Oct, Y1=0.55 Oct, Y1=0.75

75000 6

P (bar)

[B-70]

6

y x 10

T (K)

6

50000

25000

Y1 0.75 47.9 0 80000 0 72.6 49500 16500 20 106.7 49500 16500 138.4 48640 15360 Y1: Mole fraction of n -Butanol on a CO2-free basis. Source: King, M. B.; Alderson, D. A.; Fallah, F. H.; Kassim, D. M.; Sheldon, J. R.; Mahmud, R. S. in Chapter 2, Chemical Engineering at Supercritical Fluid Conditions, Paulaitis, M. E.; Penninger, J. M. L.; Gray, Jr., R. D.; Davidson, P. (Eds.) Ann Arbor Science, 1983, pp. 31-80.

60

100 P (bar)

140

Butyl acetate (C6H12O2; MW=116.16) 6

[B-71] 313 K 323 K

y x 10

6

y x 10 T (K) P (bar) 30000 313 80 3500 85 11100 90 13500 100 14400 120 10000 20000 130 16600 140 19600 160 17900 180 22400 10000 323 80 3400 85 4300 90 7200 100 15400 0 120 11100 50 140 12300 160 17000 180 19500 Source: Ghaziaskar, H. S.; Nikravesh, M. Fluid Phase Equil. (2003), 206(1-2), 215-221.

100

CAT4240—CHAPTER 2—31/10/2006—18:29—MUGUNTHAN—XML MODEL C – pp. 75–149

P (bar)

150

200

Solubility Data B

143

Butyl acetate (C6H12O2; MW=116.16) y x 10

10000 11300 21400 32200

Source: Ghaziaskar, H. S.; Nikravesh, M. Fluid Phase Equil. (2003), 206(1-2), 215-221.

40000 y x 106

P (bar) T (K) 123 313 323 333 353

[B-72]

6

20000

0 300

320

T (K)

p-tert-Butylcalix[4]arene (C44H56O4; MW=648.94)

[B-73]

313.1 K 323.1 K 333.0 K

y x 10

6

P (bar)

360

6

M x 10 y1) x 106 (mol/L) 0.245 313.1 110 3.84 1.2 0.358 124 5.94 0.452 138 7.80 0.523 152 9.39 0.589 165 10.70 0.660 179 12.30 0.8 0.737 192 13.90 0.828 210 16.00 0.139 323.1 111 1.64 0.246 126 3.47 0.361 137 5.50 0.4 0.517 151 8.34 0.660 166 11.10 0.759 178 13.10 0.903 194 16.00 1.025 206 18.40 0.0 0.171 333.0 111 1.44 50 0.199 124 2.13 0.263 140 3.40 0.339 151 4.77 0.509 165 7.63 0.619 179 9.70 0.776 192 12.70 207 16.40 0.975 1: Calculated from M. Source: Graham, B. F.; Lagalante, A. F.; Bruno, T. J.; Harrowfield, J. M.; Trengove, R. D. Fluid Phase Equil. (1998), 150-151, 829-838. T (K)

340

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150 P (bar)

250

144

Solubility in Supercritical Carbon Dioxide

p-tert-Butylcalix[6]arene (C66H84O6; MW=973.40)

323.1

333.0

109 122 136 150 167 179 190 208 110 125 137 151 163 178 192 205 111 124 138 150 164 178 193 206

M x 106 (mol/L) 1.64 2.05 2.33 2.59 2.90 3.14 3.34 3.57 1.05 1.23 1.46 1.72 2.09 2.44 2.79 3.12 0.53 0.70 0.85 1.03 1.23 1.46 1.67 1.82

y1) x 106 0.105 0.124 0.135 0.146 0.158 0.169 0.177 0.185 0.091 0.087 0.096 0.107 0.126 0.141 0.157 0.174 0.063 0.065 0.067 0.074 0.082 0.093 0.102 0.108

0.20

0.15 6

313.1

P (bar)

y x 10

T (K)

[B-74]

0.10

313.1 K 323.1 K 333.0 K

0.05

0.00

50

150 P (bar)

250

1: Calculated from M. Source: Graham, B. F.; Lagalante, A. F.; Bruno, T. J.; Harrowfield, J. M.; Trengove, R. D. Fluid Phase Equil. (1998), 150-151, 829-838.

p-tert-Butylcalix[8]arene (C88H112O8; MW=1297.87)

323.05

112 124 138 151 165 179 192 206 111 124 141 151 166 179 192 206

M x 10 (mol/L) 0.58 0.70 0.85 1.04 1.26 1.46 1.61 1.76 0.92 1.06 1.28 1.45 1.63 1.83 2.07 2.25

y1) x 106 0.037 0.042 0.049 0.059 0.069 0.078 0.085 0.091 0.078 0.077 0.083 0.090 0.098 0.106 0.117 0.125

0.15 313.05 K 323.05 K 332.95 K

0.10 6

313.05

P (bar)

[B-75]

y x 10

T (K)

6

0.05

0.00

50

100

CAT4240—CHAPTER 2—31/10/2006—18:29—MUGUNTHAN—XML MODEL C – pp. 75–149

150 P (bar)

200

250

Solubility Data B

145

0.057 111 0.48 0.060 125 0.66 0.074 137 0.95 0.082 151 1.14 0.090 164 1.35 0.097 179 1.52 0.102 192 1.66 206 1.85 0.110 1: Calculated from M. Source: Graham, B. F.; Lagalante, A. F.; Bruno, T. J.; Harrowfield, J. M.; Trengove, R. D. Fluid Phase Equil. (1998), 150-151, 829-838. 332.95

[B-76]

Butyl 2,5-dichlorobenzoate (C11H12Cl2O2; MW=247.12) y x 106 2900 2900 2900 2900 2900 2900 4300 4300 4300 4300 4300 4300 17500 17500 17500 17500 17500 35000 35000 35000 35000 35000

250

P (bar)

T (K) P (bar) 307.75 92.2 312.75 102.8 319.95 118.6 334.05 145.0 358.45 186.4 379.95 210.6 307.65 82.3 313.15 94.6 323.05 122.4 338.75 157.7 354.25 197.7 374.75 224.9 298.65 101.2 315.95 154.2 327.75 189.5 342.55 221.4 358.75 253.9 294.25 100.5 306.95 137.4 328.25 193.3 346.15 234.5 362.35 266.6

y=0.0029 y=0.0043 y=0.0175 y=0.0350 y=0.0442 y=0.0621

150

50 250

300

CAT4240—CHAPTER 2—31/10/2006—18:29—MUGUNTHAN—XML MODEL C – pp. 75–149

T (K)

350

400

146

Solubility in Supercritical Carbon Dioxide

127.2 44200 165.5 44200 211.9 44200 272.4 44200 121.0 62100 151.5 62100 167.2 62100 184.1 62100 227.3 62100 276.8 62100 Synonym: 2,5-Dichlorobenzoic acid butyl ester Source: Shen, Z.; McHugh, M. A.; Loot, K, M.: Wright, M. E. Fluid Phase Equil.(2004), 216(1), 1-12. 297.95 311.95 331.75 361.05 297.05 308.25 314.65 320.35 338.15 363.45

1-Butyl-3-methylimidazolium hexafluorophosphate (C8H15N2 · F6P; FW=284.18) P (bar)

313

150

313

120

150

328

150

313

150

Cosolvent (mol%) Acetone 9.3 15.4 23.6 Ethanol 0.0 8.5 11.3 16.5 25.4 30.5 0.0 8.3 17.3 24.4 26.9 29.8 0.0 11.5 17.3 24.4 29.1 n-Hexane 6.1 10.0 17.0 28.8

y x 106 4.5 148.0 586.0 0.2 6.3 15.0 50.7 219.0 370.0 0.3 9.5 66.2 236.0 313.0 453.0 0.1 14.4 89.1 245.0 387.0

600

y x 106

T (K)

[B-77]

Acetn, 150 bar EtOH, 120 bar EtOH, 150 bar n-Hex,150 bar

400

200

0

0

0.44 0.55 0.57 1.38

Synonym: Ionic liquid [bmim][PF6] Source: Wu, W.; Zhang, J.; Han, B.; Chen, J.; Liu, Z.; Jiang, T.; He, J.; Li, W. Chem. Comm. (2003), (12), 1412-1413.

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10 20 Cosolvent (mol %)

30

Solubility Data B

147

1-Butyl-3-methylimidazolium hexafluorophosphate (C8H15N2 · F6P; FW=284.18)

[B-78]

T (K)

Cosolvent P (bar) (mol%)

y x 106

Acetonitrile 0.0 0.3 10.0 90.0 15.0 700.0 12000 20.0 1536.0 25.0 11930.0 Methanol 313.15 150 10.0 9.5 15.0 36.3 8000 20.0 129.5 24.0 423.0 Ethanol + n-Hexane 313.15 150 9.8 0.2 4000 20.0 29.7 26.0 38.9 29.0 45.1 Acetone + n-Hexane 313.15 150 9.7 0.7 0 15.0 6.4 0 19.8 62.1 25.0 123.0 Ethanol + Acetone 313.15 150 9.9 12.1 15.0 72.7 20.0 273.0 Synonym: Ionic liquid [bmim][PF6] Source: Wu, W.; Li, W.; Han, B.; Jiang, T.; Shen, D.; Zhang, Z.; Sun, D.; Wang, B. J. Chem. Eng. Data (2004), 49(6), 1597-1601. 150

y x 106

313.15

Acetonitrile Methanol Ethanol + n-Hexane Acetone + n-Hexane Ethanol + Acetone

1-Butyl-3-methylimidazolium tetrafluoroborate (C8H15N2·BF4; FW=226.02) P (bar)

313.15

150

Ethanol1) (mol%) 0 10 15 20 25 30

y x 106 0.9 1.7 812.0 2050.0 5210.0 8590.0

[B-79]

10000 y x 106

T (K)

30

10 20 Cosolvent (mol%)

5000

1: Cosolvent in CO2. Synonym: Ionic liquid [bmim][BF4] Source: Wu, W.; Li, W.; Han, B.; Jiang, T.; Shen, D.; Zhang, Z.; Sun, D.; Wang, B. J. Chem. Eng. Data (2004), 49(6), 1597-1601.

0

0

10 20 Ethanol (mol%)

CAT4240—CHAPTER 2—31/10/2006—18:29—MUGUNTHAN—XML MODEL C – pp. 75–149

30

148

Solubility in Supercritical Carbon Dioxide

2-tert-Butylphenol (C10H14O; MW=150.22) 353.2

373.2

393.1

P (bar) 60.9 60.9 80.9 80.9 80.9 80.9 100.9 100.9 100.9 120.9 120.9 140.8 140.8 160.8 160.8 180.8 180.8 60.9 60.9 80.9 80.9 80.9 100.9 100.9 120.9 120.9 120.9 140.9 140.9 160.8 160.8 180.8 180.8 180.8 200.9 200.9 200.9 60.9 60.9 80.9 80.9 100.9 100.9 100.9 100.9 120.9 120.9

y x 106 600 800 600 600 800 600 1400 1200 1300 3300 3400 7000 7000 16100 16500 34800 34000 1100 900 1200 1300 1400 2000 2000 2400 2200 2700 4600 4600 10100 9900 15500 15700 16200 28500 27500 28100 2200 2100 2200 2300 2800 2700 3000 3000 4300 4300

40000 353.2 K 373.2 K 393.1 K

30000 y x 106

T (K)

[B-80]

20000

10000

0 50

100

CAT4240—CHAPTER 2—31/10/2006—18:29—MUGUNTHAN—XML MODEL C – pp. 75–149

150 P (bar)

200

Solubility Data B

149

140.9 160.8 160.8 180.8 180.8 200.8 200.8

5900 8900 8800 13000 12800 20400 19800

200.8

20000

Synonym: 2-(1,1-Dimethylethyl)phenol Source: Walther, D.; Maurer, G. J. Chem. Eng. Data (1993), 38, 247-249.

tert-Butyl-salen1) (C32H48N2O2; MW=492.74) 1500

1000

y x 106

T (K) P2) (bar) y2) x 106 294.15 70.1 170 102.0 300 141.6 430 182.8 520 203.8 580 304.1 620 334.15 142.4 150 182.1 770 202.3 1100 304.1 1390

[B-81]

294.15 K 334.15 K

500

0

1: The name of this compound, N,N'0 Bis(3,5-di-tert-butylsalicylidene) ethylenediamine, in the source was corrected to the synonym below, based on the diagram in the source article. 2: Obtained by digitizing the graph in the original article. Synonym: N,N '-Bis(4,6-di-tert-butylsalicylidene)ethylenediamine Source: Koh, S.; Jeon, B.; Kim, H.; Park, K.; Kim, H. Bull. Korean Chem. Soc. (2004), 25(4), 471-474.

100

CAT4240—CHAPTER 2—31/10/2006—18:29—MUGUNTHAN—XML MODEL C – pp. 75–149

200 P (bar)

300

3

Solubility Data C

Cafestol (C20H28O3; MW=316.43)

[C-1]

106

x T(K) P(bar) S (g/L) 313.15 101.33 0.060 13.0 121.59 0.170 32.6 151.99 0.310 54.9 202.65 0.500 82.4 253.31 0.700 110.2 333.15 101.33 0.001 0.5 121.59 0.010 3.1 151.99 0.110 24.9 202.65 0.350 66.7 253.31 0.640 112.4 353.15 101.33 0.000 0.0 121.59 0.002 0.9 151.99 0.020 6.3 202.65 0.170 39.2 92.3 253.31 0.460 1: Calculated from S. Synonym: Cafesterol Source: Chrastil, J. J. Phys. Chem. (1982), 86(15), 3016-3021.

120 313.15 K 333.15 K 353.15 K

80 y x 106

y1)

40

0 50

Caffeic acid (C9H8O4; MW=180.16) T (K) P (bar) 313 150 200 250 300 350 400 450 500

150

250

P (bar)

[C-2]

106

yx 0.0008 0.0020 0.0052 0.0092 0.0118 0.0133 0.0154 0.0182

151

CAT4240—CHAPTER 3—1/11/2006—17:27—SRIDHAR—XML MODEL C – pp. 151–270

152

Solubility in Supercritical Carbon Dioxide

333

150 200 250 300 350 400 450 500 150 200 250 300 350 400 450 500

0.0011 0.0042 0.0118 0.0189 0.0231 0.0270 0.0298 0.0324 0.0032 0.0106 0.0182 0.0265 0.0333 0.0393 0.0436 0.0472

313 K 323 K 333 K

0.04 y x 106

323

0.02

0.00 0

200

Synonyms: 3,4-Dihydroxycinnamic acid; 3,4-Dihydroxybenzeneacrylic acid Source: Murga, R.; Sanz, M.T.; Beltran,S.; Cabezas, J. L. -J. Supercrit. Fluids (2003), 27(3), 239-245.

400 P (bar)

Caffeine (C8H10N4O2; MW=194.19) T (K)

P (bar)

104

Mx (mol/L)

600

[C-3] 400

y x 106

y x 106

313.15 100.0 9 63 103.4 12 78 200 137.9 23 140 150.0 26 150 172.4 35 190 0 206.8 48 250 300.0 71 370 50 Synonyms: 1,3,7-Trimethyl-2,6dioxopurine; 1,3,7-Trimethylxanthine Source : Burgos-Solorzano, G. I.; Brennecke, J. F.;Stadtherr, M. A. Fluid Phase Equil. (2004), 220(1), 57-69.

150

250

350

P (bar)

[C-4] Caffeine (C8H10N4O2; MW=194.19) P1) M2) x 105 (bar) (mol/L) 3.24 323 91.9 14.98 103.8 43.44 115.7 117.59 141.9 0.49 333 61.7 4.27 105.4 19.18 120.2 62.18 139.2 186.45 172.2 0.81 343 93.3 6.49 115.9

T (K)

y3) x 106 4.3 14.6 34.4 78.0 1.6 5.6 18.9 49.3 123.6 1.6 8.6

CAT4240—CHAPTER 3—1/11/2006—17:27—SRIDHAR—XML MODEL C – pp. 151–270 .

Solubility Data C

373

383

393

403

413

423 433

25.03 89.68 1.28 10.03 40.34 140.15 0.32 0.35 2.25 13.90 14.21 64.07 0.64 0.66 3.69 23.10 95.32 1.09 1.26 5.81 37.30 147.18 1.63 1.77 10.36 10.99 56.79 3.24 4.12 16.92 83.93 6.31 25.74 127.70

24.8 71.1 2.5 13.3 40.0 111.1 1.2 1.1 4.5 18.4 18.8 63.6 2.1 2.2 7.3 30.6 94.6 4.2 3.6 11.5 49.6 146.3 5.8 5.4 21.8 20.5 75.1 10.7 13.6 33.6 111.2 20.8 51.1 169.2

90.7 141.8 94.3 147.5

10.83 39.06 16.81 59.89

35.9 77.4 55.7 119.0

150 323 K 343 K 363 K 383 K 403 K 423 K

100 6

363

136.7 160.4 97.5 127.2 152.8 185.7 71.6 71.6 104.6 138.2 138.2 170.0 75.6 75.6 111.3 148.6 186.2 80.0 80.0 118.1 160.0 201.9 82.1 82.1 123.8 123.8 170.9 84.7 84.7 130.0 180.0 87.5 135.6 191.1

y x 10

353

153

50

0 50

1: Calculated from density and temperature by using Wagner equation of state. 2: Obtained by using log (c/c0) values and the equation for log c0 in the source. 3: Calculated from M. Synonyms: 1,3,7-Trimethyl-2,6dioxopurine; 1,3,7-Trimethylxanthine Source: Ebeling, H.; Franck, E. U. Ber. Bunsenges. Phys. Chem. (1984), 88(9), 862-865.

CAT4240—CHAPTER 3—1/11/2006—17:27—SRIDHAR—XML MODEL C – pp. 151–270

100

150 P (bar)

200

154

Solubility in Supercritical Carbon Dioxide

Caffeine (C8H10N4O2; MW=194.19)

[C-5]

106

313 K 333 K 353 K

y x 106

yx T (K) P (bar) 295 313 199 329 219 387 239 401 259 1100 428 279 458 299 485 319 544 349 800 304 333 199 369 219 444 239 512 259 587 279 500 607 299 625 319 722 349 283 353 199 200 385 219 150 476 239 537 259 643 279 804 299 933 319 349 1130 Synonyms: 1,3,7-Trimethyl-2,6-dioxopurine; 1,3,7Trimethylxanthine Source: Johannsen, M.; Brunner, G. Fluid Phase Equil.(1994), 95, 215-226.

Caffeine (C8H10N4O2; MW=194.19) T (K) P (bar) 313.15 95 148 198 243 298 333.15 106 112 148 200 225 242 265 298

y x 106 15.1 131.0 197.0 278.0 360.0 2.7 4.4 50.5 180.0 268.0 306.0 377.0 414.0

CAT4240—CHAPTER 3—1/11/2006—17:27—SRIDHAR—XML MODEL C – pp. 151–270

250

350

P (bar)

[C-6]

Solubility Data C

155

600 353.15

313.15 K 333.15 K 353.15 K 368.15 K

400 y x 106

105 1.9 148 27.7 198 151.0 236 282.0 268 401.0 298 482.0 368.15 80 0.5 150 21.8 198 125.0 238 280.0 266 463.0 298 515.0 Synonyms: 1,3,7-Trimethyl-2,6-dioxopurine; 1,3,7-Trimethylxanthine Source: Li, S.; Varadarajan, G. S.; Hartland, S. Fluid Phase Equil. (1991), 68, 263-280.

200

0 50

150

250

350

P (bar) Caffeine (C8H10N4O2; MW=194.19)

[C-7]

313.2 K 323.2 K 343.2 K

y x 10

6

W1) (g/kg) y2)x 106 T (K) P1) (bar) 313.2 138.6 0.69 157 152.2 0.89 201 500 166.3 1.09 248 179.3 1.21 273 192.8 1.29 292 400 206.9 1.36 308 220.5 1.54 349 234.0 1.72 389 300 323.2 138.1 0.56 127 152.2 0.76 171 165.7 0.99 224 179.3 1.15 261 200 192.8 1.32 298 206.4 1.51 342 220.5 1.66 377 100 233.5 1.81 410 343.2 138.1 0.25 56 152.2 0.39 88 0 165.7 0.63 143 100 178.7 0.87 197 192.8 1.38 312 206.9 1.66 377 220.5 1.88 426 233.5 2.03 460 1: Obtained by digitizing the graph in the original article. 2: Calculated from W. Synonyms: 1,3,7-Trimethyl-2,6-dioxopurine; 1,3,7Trimethylxanthine Source: Saldana,M.D.A.; Mohamed, R.S.;Baer, M. G.; Mazzafera, P. J. Agric. Food. Chem. (1999), 47, 38043808.

CAT4240—CHAPTER 3—1/11/2006—17:27—SRIDHAR—XML MODEL C – pp. 151–270

150

200 P (bar)

250

156

Solubility in Supercritical Carbon Dioxide

Caffeine (C8H10N4O2; MW=194.19) T (K) P1) (bar)

W1) (g/kg CO2)

[C-8]

y2) x 106

200

95.6 0.23 53 101.5 0.28 64 105.1 0.26 60 102.3 0.31 70 100 112.1 0.33 75 114.1 0.43 99 122.2 0.41 94 131.5 0.46 104 133.5 0.52 118 0 134.9 0.50 114 80 134.0 0.54 122 137.1 0.52 118 176.0 0.78 177 178.0 0.72 163 1: Obtained by digitizing the graph in the original article. 2: Calculated from W. Synonyms: 1,3,7-Trimethyl-2,6-dioxopurine; 1,3,7Trimethylxanthine Source: Skerget, M.; Knez, Z.V. Slovenskega Kemijskega Drustva (1991), 38(3), 413-426.

y x 106

323.15

120

160

Caffeine (C8H10N4O2; MW=194.19)

294.15 55.4 64.4 70.2 80.8 100.0 120.2 149.7 308.15 68.3 74.7 79.5 89.1 99.4 149.4 200.0 313.15 78.5 84.6 88.1 99.7 118.9 149.0

0.01 0.53 0.56 0.62 0.73 0.77 0.86 0.02 0.04 0.21 0.45 0.62 1.03 1.31 1.03 1.06 1.18 1.43 1.81 1.17

[C-9]

y3) x 106 1 60 64 71 84 89 99 2 5 24 52 71 118 150 3 7 20 50 93 134

200 294.15 K 308.15 K 313.15 K 333.15 K

150 y x 106

S1) 1) T(K) P (bar) (mg/Nl2))

200

P (bar)

100 50 0 0

CAT4240—CHAPTER 3—1/11/2006—17:27—SRIDHAR—XML MODEL C – pp. 151–270

50

100 150 P (bar)

200

Solubility Data C

157

199.7 1.50 172 333.15 89.1 0.02 2 109.6 0.09 10 129.8 0.26 30 149.7 0.56 65 169.6 0.81 93 146 200.3 1.28 1: Obtained by digitizing the graph in the original article. 2: "Nl" means "Normliter," which is one liter at 273.15 K and 1 atm. 3: Calculated from S. Synonyms: 1,3,7-Trimethyl-2,6-dioxopurine; 1,3,7Trimethylxanthine Source: Stahl, E.; Schilz, W.Talanta(1979), 26, 675-679.

Caffeine (C8H10N4O2; MW=194.19)

[C-10]

106

313 K 323 K 333 K 343 K 353 K 363 K

y x 106

yx T (K) P (bar) 313 86.9 10.5 90 94.1 17.1 323 81.3 0.9 93.5 3.9 116.6 12.2 142.2 24.3 60 333 86.6 1.3 107.9 5.6 134.3 19.8 157.0 35.6 343 93.6 1.9 30 119.4 8.6 147.0 29.4 175.4 52.6 353 99.9 2.9 128.4 12.0 0 159.6 50.3 50 190.0 71.3 363 106.1 4.7 175.1 66.6 215.9 83.2 Synonyms: 1,3,7-Trimethyl-2,6-dioxopurine; 1,3,7Trimethylxanthine Source: Tzvetkova, E., Doctoral Thesis, Siegen University, Siegen, Germany, 2001.

100

CAT4240—CHAPTER 3—1/11/2006—17:27—SRIDHAR—XML MODEL C – pp. 151–270

150 P (bar)

200

250

158

Solubility in Supercritical Carbon Dioxide

Caffeine (C8H10N4O2; MW=194.19) P (bar)

(wt%)

W (g/kg solv)

[C-11] 4000

y2) x 106

313

219 0.0 1.5 340 218 4.2 5.4 1200 218 5.2 5.8 1290 218 5.2 5.9 1310 218 7.0 8.8 1940 218 7.1 8.5 1870 218 10.5 13.4 2910 218 10.8 16.3 3540 1: Cosolvent in CO2 on a solute-free basis. 2: Calculated from W. Synonyms: 1,3,7-Trimethyl-2,6-dioxopurine; 1,3,7Trimethylxanthine Source: Johannsen, M.; Brunner, G. J. Chem. Eng. Data (1995), 40(2), 431-434.

y x 106

T (K)

Methanol1)

2000

0 0

4

P (bar)

313.05

323.05

333.95

113 124 138 151 165 179 192 206 110 124 138 151 165 179 192 206 112 124 138 152 165 180 192 208

Mx (mol/L) 6.38 8.30 10.20 12.50 14.80 17.10 19.50 21.80 4.69 6.88 9.32 11.70 14.30 17.20 20.00 22.80 1.81 3.32 5.15 7.47 9.97 13.00 16.00 19.60

[C-12]

y1) x 106 0.401 0.500 0.591 0.696 0.814 0.918 1.034 1.129 0.397 0.488 0.612 0.725 0.851 0.996 1.129 1.270 0.210 0.304 0.405 0.530 0.665 0.829 0.978 1.166

1.5 313.05 K 323.05 K 332.95 K

1 y x 106

T (K)

12

Methanol (wt%)

Calix[4]arene (C28H24O4; MW=424.49) 106

8

0.5

0 50

1: Calculated from M. Synonym: Calix[4]arene-25,26,27,28-tetrol Source: Graham, B. F.; Lagalante, A. F.; Bruno, T. J.; Harrowfield, J. M.; Trengove, R. D. Fluid Phase Equil. (1998), 150-151 829-838.

CAT4240—CHAPTER 3—1/11/2006—17:27—SRIDHAR—XML MODEL C – pp. 151–270

150 P (bar)

250

Solubility Data C

159

[C-13]

Camphor (C10H16O; MW=152.23) 106

313 K 323 K 333 K

y x 106

yx T (K) P (bar) 313 76.3 863 79.3 1040 79.7 1460 81.7 1660 83.1 1670 84.2 2470 84.6 15900 85.0 19200 88.1 27800 40000 104.3 32800 126.1 38600 323 75.5 1090 81.4 1140 30000 88.2 1630 90.0 2420 92.2 3470 94.3 3840 20000 95.4 4560 96.6 4840 97.7 5400 101.2 28500 10000 102.0 26200 103.5 30100 108.8 32500 116.6 34000 0 333 75.1 990 70 80.9 970 86.3 1520 92.2 2430 98.0 3600 101.9 4970 106.7 5870 109.4 6730 112.3 9930 113.5 16400 114.3 18700 116.1 23000 117.8 32100 125.0 36000 Synonyms: 2-Bornanone; 1,7,7-Trimethylbicyclo [2,2,1]heptan-2-one Source: Akgun, M.; Akgun, N. A.; Dincer, S. J. Supercrit. Fluids (1999), 15(2), 117-125.

CAT4240—CHAPTER 3—1/11/2006—17:27—SRIDHAR—XML MODEL C – pp. 151–270

100 P (bar)

130

160

Solubility in Supercritical Carbon Dioxide

[C-14]

Canola oil1) T (K)

P2) (bar)

W2) (g/kg CO2)

w3) x 106

12000

101 0.88 880 203 4.88 4860 305 8.02 7960 364 8.66 8590 8000 313.15 100 0.09 90 202 3.05 3040 305 8.02 7960 363 10.88 10760 4000 328.15 100 0.09 90 201 1.95 1950 304 7.32 7270 364 11.37 11240 0 343.15 101 0.09 90 100 203 1.04 1040 303 5.91 5880 363 10.88 10760 1: One type of rapeseed oil extracted from a cultivar of Brassica napus that grows in Canada. 2: Obtained by digitizing the graph in the original article. 3: Calculated from W. Source: Fattori, M.; Bulley, N. R.; Meisen, A. J. Am. Oil Chem. Soc. (1988), 65(6), 968-974.

w x 106

298.15

298.15 K 313.15 K 328.15 K 343.15 K

200

300 P (bar)

[C-15]

6-Caprolactam (C10H19NO; MW=169.27) yx

20100 22500 25200 28300 35800 40200 42200 39900 45400 43500 48800 58200 58300 73300 22100 29200 32700 40200 50400 48000 58200

80000 307 K 314 K 324 K

60000 y x 106

T (K) P (bar) 307 101 108 114 124 134 142 145 149 151 152 154 154 168 173 314 138 149 156 169 179 180 191

106

400

40000

20000 50

CAT4240—CHAPTER 3—1/11/2006—17:27—SRIDHAR—XML MODEL C – pp. 151–270

150 P (bar)

250

Solubility Data C

161

196 54600 208 73300 324 141 21500 154 22100 172 29200 172 32700 200 42200 201 48000 203 40200 217 50400 227 54600 Source : Laitinen, A.; Jaentti, M. J. Chem. Eng. Data (1996), 41(6), 1418-1420.

Capsaicin (C18H27NO3; MW=305.41) T (K)

P (bar) M (mol/m3)

[C-16]

y1) x 106

308

600 308 K 318 K 328 K

400

y x 106

129.0 1.78 100 138.9 2.00 110 152.9 2.29 123 170.0 2.61 137 194.9 3.07 156 219.9 3.46 172 249.9 3.91 190 318 120.0 1.93 128 128.9 2.29 145 138.9 2.86 174 152.9 3.46 203 170.0 4.22 239 194.9 5.60 304 219.9 7.05 372 249.9 8.68 444 328 120.0 1.41 121 128.9 1.80 138 138.9 2.19 156 152.9 3.02 199 170.0 3.91 243 194.9 6.31 370 219.9 7.96 448 249.9 9.38 508 1: Calculated from M. Synonym: (E )-8-Methyl-N-vanillyl-6-nonenamide Source: Hansen, B. N. ; Harvey, A. H. ; Coelho, J. A. P. ; Palavra, A. M. F. ; Bruno, T. J. J. Chem. Eng. Data (2001), 46(5), 1054-1058.

200

0 100

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150

200 P (bar)

250

162

Solubility in Supercritical Carbon Dioxide

Capsaicin (C18H27NO3; MW=305.41) T (K) P (bar) 298.2 76 97 123 157 160 165 217 222 285 290 290 319 313.2 76 76 107 147 191 194 196 228 228 264 269 275 337 340 348 333.2 92 107 110 141 170 173 175 175 201 201 201 246 249 251 251 251 262 264 269 272 275 309

[C-17]

1)

y x 106 59 76 84 105 97 110 118 114 118 122 127 131 34 46 105 101 152 164 173 160 173 181 207 207 198 219 219 55 84 122 131 236 299 194 232 240 245 249 211 194 207 228 245 202 215 194 219 232 261

400 298.2 K 313.2 K 333.2 K

300 y x 106

1)

200

100

0 0

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100

200 P (bar)

300

400

Solubility Data C

163

311 245 311 270 361 283 363 274 374 295 392 308 395 316 400 291 1: Obtained by digitizing the graph in the original article. Synonym: (E )-8-Methyl-N-vanillyl-6-nonenamide Source: Knez, Z.; Steiner, R. J. Supercrit. Fluids (1992), 5(4), 251-255.

[C-18]

Capsaicin (C18H27NO3; MW=305.41)

y x 106

Mass T (K) P1) (bar) ratio2) (b- y1,3) x 106 car/cap) 1:1 18.8 298.15 107 142 1:1 19.6 166 1:1 18.1 185 1:1 23.3 80 218 1:1 35.4 260 1:1 31.6 101 2:1 27.8 130 2:1 27.1 60 158 2:1 27.8 201 2:1 28.6 234 2:1 27.8 276 2:1 25.6 40 1:1 41.4 99 313.15 140 1:1 61.0 172 1:1 54.9 198 1:1 76.0 20 232 1:1 24.1 252 1:1 24.1 264 1:1 26.3 0 272 1:1 24.1 304 1:1 28.6 0 312 1:1 33.9 99 2:1 22.6 128 2:1 29.4 165 2:1 32.4 204 2:1 39.1 228 2:1 30.1 272 2:1 31.6 302 2:1 41.4 1: Obtained by digitizing the graph in the original article. 2. The mass ratio of b -carotene and capsaicin in the feed. 3: Solubility of capsaicin was measured from the binary mixture of b -carotene and capsaicin. Synonym: (E)-8-Methyl-N-vanillyl-6-nonenamide Source : Skerget, M.; Knez, Z. J. Agric. Food Chem. (1997), 45(6), 2066-2069.

298.15 K , 1:1 298.15 K , 2:1 313.15 K , 1:1 313.15 K , 2:1

100

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200 P (bar)

300

400

164

Solubility in Supercritical Carbon Dioxide

Carbamazepine (C15H12N2O; MW=236.27) 1)

1)

T (K) P (bar) y x

[C-19]

106

60 y x 106

Anhydrate 313.15 100 1.4 199 9.0 350 11.4 Hydrate (C15H12N2O 2H2O) 313.15

100 10.2 199 33.3 3494 3.2 1:Obtained by digitizing the graph in the original article. Synonym: 5H-Dibenz[b,f]azepine-5-carboxamide Source: Bettini, R.; Bertolini, G.; Frigo, E.; Rossi, A.; Casini, I.; Pasquali, I.; Giordano, F. J. Therm. Anal. Cal. (2004), 77(2), 625-638.

Anhydrate Hydrate

40 20 0 50

150

250 P (bar)

Carbamazepine (C15H12N2O; MW=236.27) S (g/L) 0.05 0.06 0.07 0.07 0.08 0.02 0.03 0.05 0.07 0.08 0.09 0.11 0.12 0.14 0.01 0.02 0.04 0.05 0.08 0.11 0.13 0.16 0.17 0.01 0.03 0.07 0.10 0.14 0.20

yx

[C-20]

106 11 13 14 15 16 6 8 11 15 17 20 22 24 28 3 7 10 13 19 24 28 33 36 4 10 19 26 34 45

100 308 K 318 K 328 K 338 K 348 K

y x 106

T (K) P (bar) 308 243 274 304 334 355 318 122 152 182 213 243 274 304 334 355 328 122 152 182 213 243 274 304 334 355 338 152 182 213 243 274 304

350

50

0 100

CAT4240—CHAPTER 3—1/11/2006—17:27—SRIDHAR—XML MODEL C – pp. 151–270

200

300 P (bar)

400

Solubility Data C

165

334 355 152 182 213 243 274 304 334 355

0.25 55 0.32 71 348 0.06 24 0.06 20 0.06 17 0.10 27 0.17 42 0.23 56 0.32 75 0.41 94 Synonym: 5H-Dibenz[b,f]azepine-5-carboxamide Source: Yamini, Y. ; Hassan, J. ; Haghgo, S. J. Chem. Eng. Data (2001), 46(2), 451-455.

Carbamazepine polymorph I (1) + polymorph III (2) Mixture (C15H12N2O; MW=236.2) T (K)

P (bar)

y11)x 106

y21) x 106

[C-21]

30

100 1.5 1.3 125 5.1 4.8 150 10.0 7.9 175 9.5 N/A 200 8.0 10.6 20 225 11.5 N/A 250 12.5 8.6 300 8.0 10.7 350 9.0 11.5 10 328.15 110 0.8 0.8 125 2.0 2.4 150 5.0 5.9 200 10.0 8.7 250 12.5 12.5 0 300 17.5 11.5 50 350 29.0 13.8 1: Obtained by digitizing the graph in the original article. Synonym: 5H-Dibenz[b,f]azepine-5-carboxamide Source: Bettini, R.; Bonassi, L.; Castoro, V.; Rossi, A.; Zema, L.; Gazzaniga, A.; Giordano, F. Europ. J. Pharm. Sci. (2001), 13(3), 281-286.

Form I - 313 K Form I - 328 K Form III - 313 K Form III - 328 K

y x 106

313.15

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150

250 P (bar)

350

166

Solubility in Supercritical Carbon Dioxide

Carbazole (C12H9N; MW=167.21)

[C-22]

106

30 y x 106

yx T (K) P (bar) 308.2 103 14.3 121 16.2 161 17.9 181 22.9 201 27.6 Synonyms: 9-Azafluorene; Dibenzopyrrole Source: Goodarznia, I.; Esmaeilzadeh, F. J. Chem. Eng. Data (2002), 47(2), 333-338.

20

10 100

150

200

P (bar)

Carbazole (C12H9N; MW=167.21) yx

12.0 14.2 14.8 15.4 19.0 18.9 19.8

20 y x 106

T (K) P (bar) 100 313.1 110 125 135 150 175 200

[C-23]

106

15

10 50

Synonyms: 9-Azafluorene; Dibenzopyrrole Source: Kwiatkowski, J.; Lisicki, Z.; Majewski, W. Ber. Bunsenges. Phys. Chem. (1984), 88(9), 865-869.

150

250

P (bar)

N-Carbobenzoxy aspartic acid (C12H13NO6; MW=267.24) T (K)

P1)

(bar)

y1)

x

106

200 70 220 81 240 103 260 120 323.15 200 80 220 184 240 289 260 385 343.15 200 123 220 260 240 367 259 471 1: Obtained by digitizing the graph in the original article. Synonym: N-Benzyloxycarbonyl-DL-aspartic acid Source: Vedaraman, N.; Brunner, G.; Srinivasa Kannan, C.; Ramabrahmam, B. V.; Rao, P. G. J. Supercrit. Fluids (2004), 30(2), 119-125.

y x 106

313.15

[C-24]

600

400

313.15 K 323.15 K 343.15 K

200

0 190

210

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230 P (bar)

250

270

Solubility Data C

167

N-Carbobenzoxyproline (C13H15NO4; MW=249.26) P1) (bar)

y1)

[C-25]

106

x 180 104 600 200 129 220 225 240 381 400 260 500 323.15 180 192 200 225 200 220 340 240 490 260 579 0 333.15 200 298 220 385 150 240 508 260 623 1: Obtained by digitizing the graph in the original article. Synonyms: N-Benzyloxycarbonyl-DL-proline Source: Vedaraman, N.; Brunner, G.; Srinivasa Kannan, C.; Ramabrahmam, B. V.; Rao, P. G. J. Supercrit. Fluids (2004), 30(2), 119-125.

313.15 K 323.15 K 333.15 K

y x 106

T (K) 313.15

200

250

P (bar)

N-Carbobenzoxyvaline (C13H17NO4; MW=251.28)

313.15 K 323.15 K 333.15 K

y x 106

T (K) P1) (bar) y1) x 106 300 313.15 200 67 220 91 240 113 260 135 200 280 156 323.15 200 82 220 119 240 151 100 260 186 280 209 333.15 200 122 0 220 164 240 204 150 260 250 280 281 1: Obtained by digitizing the graph in the original article. Synonym: N-Benzyloxycarbonyl-DL-valine Source: Vedaraman, N.; Brunner, G.; Srinivasa Kannan, C.; Ramabrahmam, B. V.; Rao, P. G. J. Supercrit. Fluids (2004), 30(2), 119-125.

[C-26]

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200

250 P (bar)

300

168

Solubility in Supercritical Carbon Dioxide

[C-27]

Carbonyl-p-cyclopentadienyl(triphenylphosphine)cobalt (C24H20CoOP; FW=413.31) 26

1) 6 P (bar) S (g/L CO2) y x 10

313.15

160 178 188 205

0.159 0.183 0.188 0.199

21.2 23.8 24.1 25.0

y x 106

T (K)

23

1: Calculated from S. Synonym:Carbonyl(h5-cyclopentadienyl) (triphenylphosphine)cobalt Source: Montilla, F.; Galindo, A.; Rosa, V.; Aviles, T. Dalton Trans. (2004), (16), 2588-2592.

20 150

180

210

P (bar)

Carbonyl-p-cyclopentadienyl(tris(4-trimethylsilylphenyl)phosphine)cobalt (C33H45CoOPSi3; FW=630.87)

53

1) 6 P (bar) S (g/L CO2) y x 10

313.15

166 188 204

0.595 0.621 0.610

51.6 52.2 50.4

1: Calculated from S. Synonym: Carbonyl(h5-cyclopentadienyl) [tris(4-trimethylsilylphenyl)phosphine] cobalt Source: Montilla, F.; Galindo, A.; Rosa, V.; Aviles, T. Dalton Trans. (2004), (16), 2588-2592.

y x 106

T (K)

50 150

180

210

P (bar)

[C-29]

b -Carotene (C40H56; MW=536.87) P (bar) W (mg/kg)

y1) x 106

313 300 1.9 0.16 323 300 3.8 0.31 333 300 8.0 0.66 1: Calculated from W. Synonyms: b,b -Carotene; C. I. Food Orange 5 Source: Cocero, M. J.; Gonzalez, S.; Perez, S.; Alonso, E. J. Supercrit. Fluids (2000), 19(1), 39-44.

0.8 y x 106

T (K)

[C-28]

0.4

0.0 310

CAT4240—CHAPTER 3—1/11/2006—17:27—SRIDHAR—XML MODEL C – pp. 151–270

330

320 T (K)

340

Solubility Data C

169

b -Carotene (C40H56; Mw=536.87)

[C-30]

106

Mx y1) x 106 (mol/m3) 313.15 68.3 6 0.0013 136.7 140 0.0081 205.9 572 0.0297 274.4 1050 0.0515 342.9 1600 0.0755 343.15 61.8 229 0.0825 125.8 2090 0.2411 194.2 19600 1.3279 332.9 42600 2.2982 1: Calculated from M. Synonyms: b,b -Carotene; C. I. Food Orange 5 Source: Hansen, B. N.; Harvey, A. H.; Coelho, J. A. P.; Palavra, A. M. F.; Bruno, T. J. J. Chem. Eng. Data (2001), 46(5), 1054-1058. P(bar)

y x 106

T(K)

3 313 K 343 K

2 1 0 0

100

200

300

P (bar)

[C-31]

b -Carotene (C40H56; MW=536.87)

313

333

353

P (bar) 200 220 240 260 280 300 320 350 200 220 240 260 280 300 320 350 200 220 240 260 280 300 320

W1) x102 (g/kg) 0.11 0.12 0.13 0.16 0.17 0.19 0.29 0.34 0.34 0.43 0.64 0.72 1.05 1.26 1.46 1.44 0.42 1.07 1.17 2.05 2.45 2.64 3.95

y x 106 0.09 0.10 0.11 0.13 0.14 0.16 0.24 0.28 0.28 0.35 0.52 0.59 0.86 1.03 1.19 1.18 0.35 0.88 0.96 1.68 2.01 2.17 3.24

3

y x 106

T (K)

400

313 K 333 K 353 K

2

1

0 150

1: The order of magnitude 102 is missing in the source table, and thus was estimated based on Figure 8 in the source. Synonyms: b,b -Carotene; C. I. Food Orange 5 Source: Johannsen, M. ; Brunner, G. J. Chem. Eng. Data (1997), 42(1), 106-111.

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250 P (bar)

350

170

Solubility in Supercritical Carbon Dioxide

b -Carotene (C40H56; MW=536.87)

[C-32]

106

Mx y1) x 106 (mol/L) 0.009 307.6 80 0.11 0.027 85 0.39 0.074 100 1.21 0.077 150 1.43 0.113 200 2.23 0.122 250 2.50 0.5 0.189 350 4.10 0.202 400 4.47 0.209 500 4.79 0.4 0.218 600 5.14 0.197 700 4.73 0.197 800 4.83 0.166 900 4.14 0.3 0.168 1000 4.25 0.131 1100 3.37 0.132 1200 3.44 0.2 0.138 1300 3.62 0.117 1400 3.11 0.109 1600 2.96 0.1 0.110 1800 3.03 0.006 322.9 102 0.06 0.017 110 0.20 0.0 0.024 115 0.31 0 0.033 120 0.45 0.109 150 1.75 0.160 200 2.87 0.233 250 4.44 0.234 250 4.45 0.282 300 5.59 0.381 350 7.80 0.437 400 9.20 0.448 450 9.63 0.423 500 9.26 0.456 550 10.17 600 9.85 0.435 1: Calculated from S. Synonyms: b,b -Carotene; C. I. Food Orange 5 Source: Kraska, T.; Leonhard, K. O.; Tuma, D.; Schneider, G. M. J. Supercrit. Fluids (2002), 23(3), 209-224. P (bar)

307.6 K 322.9 K

y x 106

T (K)

500

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1000 P (bar)

1500

2000

Solubility Data C

171

[C-33]

b -Carotene (C40H56; MW=536.87) 6

313 K 323 K 333 K

y x 106

y x 10 T (K) P (bar) 313 120 0.030 150 0.062 176 0.094 0.6 201 0.130 226 0.159 249 0.199 276 0.210 0.4 323 120 0.013 150 0.062 202 0.219 225 0.342 249 0.420 0.2 276 0.484 299 0.518 333 121 0.002 151 0.039 0 176 0.138 100 201 0.271 224 0.373 250 0.518 274 0.627 Synonyms: b,b -Carotene; C. I. Food Orange 5 Source: Mendes, R. L.; Nobre, B. P.; Coelho, J. P.; Palavra, A. F. J. Supercrit. Fluids (1999), 16(2), 99-106.

200

300

P (bar)

[C-34]

b-Carotene1) (C40H56; MW=536.87) 60 cis trans

y x 106

y3) x 106 T (K) P2) (bar) S2) (g/L) cis- b -carotene 0.0001 0.02 313.1 90 0.0029 0.38 100 0.0820 8.59 150 0.2100 20.50 198 0.5500 51.20 250 0.6200 55.80 298 trans-b-carotene 0.00 88 0.0000 0.10 100 0.0008 2.09 150 0.0200 5.55 200 0.0570 19.50 250 0.2100 298 0.2400 21.60

40

20

0 50

1: Solubility was measured from a natural mixture of cis-b-carotene and trans-b-carotene that were extracted from microalga Dunaliella salina. 2: Obtained by digitizing the graph in the original article. 3: Calculated from S. Synonyms: b,b-Carotene; C. I. Food Orange 5 Source: Mendes, R. L.; Nobre, B. P.; Cardoso, M. T.; Pereira, A. P.; Palavra, A. F. Inorg. Chim. Acta (2003), 356, 328-334.

CAT4240—CHAPTER 3—1/11/2006—17:28—SRIDHAR—XML MODEL C – pp. 151–270

150

250 P (bar)

350

172

Solubility in Supercritical Carbon Dioxide

[C-35]

b -Carotene (C40H56; MW=536.87) 6

0.6 298.15 K 313.15 K

0.4 6

y x 10 T (K) P (bar) S (g/L) 298.15 97.5 0.0018 0.181 126.5 0.0017 0.163 141.5 0.0024 0.226 150.0 0.0017 0.159 174.7 0.0020 0.183 198.0 0.0020 0.179 210.0 0.0015 0.133 230.0 0.0018 0.158 250.0 0.0024 0.208 257.8 0.0024 0.208 281.0 0.0015 0.128 298.0 0.0023 0.195 313.15 99.3 0.0006 0.080 109.3 0.0015 0.182 128.0 0.0018 0.200 145.0 0.0032 0.340 158.0 0.0031 0.321 178.0 0.0036 0.361 197.5 0.0041 0.401 211.0 0.0044 0.424 232.5 0.0045 0.425 257.0 0.0049 0.454 277.0 0.0051 0.466 308.5 0.0055 0.493 1: Calculated from S. Synonyms: b,b-Carotene; C. I. Food Orange 5 Source: Skerget, M.; Knez, Z.; Habulin, M. Fluid Phase Equil. (1995), 109(1), 131-138.

y x 10

1)

0.2

0.0 0

100

200

[C-36]

330

y x 10

0.015 0.022 0.051 0.094 0.135 0.148 0.155 0.041 0.110 0.220 0.270 0.309 0.401 0.091 0.165 0.224 0.260 0.385

2 310 K 320 K 330 K 340 K

y x 10

320

97 101 120 147 175 207 233 121 134 154 171 200 241 143 164 183 188 211

6

6

310

P (bar)

400

P (bar)

b -Carotene (C40H56; MW=536.87) T (K)

300

1

0 50

CAT4240—CHAPTER 3—1/11/2006—17:28—SRIDHAR—XML MODEL C – pp. 151–270

150 P (bar)

250

Solubility Data C

173

213 0.438 233 0.510 340 143 0.170 164 0.410 176 0.510 200 0.740 220 1.20 241 1.50 260 1.70 Synonyms: b,b-Carotene; C. I. Food Orange 5 Source: S ubra, P .; Castellani, S .; Ksibi, H.; Garrabos, Y. Fluid Phase Equil. (1997),131(1-2), 269-286.

[C-37]

b -Carotene (C40H56; MW=536.87) T (K)

P (bar)

0 0.009 0 0.022 0 0.066 0 0.102 333.15 0 0.043 0 0.072 0 0.095 0 0.152 0 0.272 343.15 0 0.195 0 0.333 0 0.623 0 1.00 0 1.25 0 1.91 0 2.54 Ethanol 223 1 0.96 249 1 1.95 316 1 2.52 374 1 3.75 Methylene chloride 234 1 1.28 247 1 1.33 312 1 2.17 370 1 2.77 Methanol 180 1 0.398 268 1 0.962 330 1 1.56 3.06 373 1 Synonyms: b,b-Carotene; C. I. Food Orange 5 Source: Cygnarowicz, M. L.; Maxwell, R. J.; Seider, W. D. Fluid Phase Equil. (1990), 59(1), 57-71.

4

3

CO2 313 K CO2 333 K CO2 343 K EtOH 343 K MeCl 343 K MeOH 343 K

6

275 314 384 415 236 273 309 348 373 212 249 287 328 358 400 439

y x 106

y x 10

313.15

Cosolvent (wt%)

2

1

0 100

200

CAT4240—CHAPTER 3—1/11/2006—17:28—SRIDHAR—XML MODEL C – pp. 151–270

300 P (bar)

400

500

174

Solubility in Supercritical Carbon Dioxide

[C-38]

b-Carotene (C40H56; MW=536.87)

313.2

P (bar)

(wt%)

120 150 200 250 280 323.2 150 200 250 280 333.2 150 200 250 280 313.2 150 150 200 200 250 250 280 323.2 150 200 250 280 280 333.2 150 200 250 250 280 280 1: Cosolvent in CO2.

0 0 0 0 0 0 0 0 0 0 0 0 0 2.12 2.37 0.42 0.76 0.44 0.67 0.30 2.07 0.92 0.65 0.38 1.30 1.92 1.48 0.64 0.64 0.55 1.00

y x 106 0.032 0.066 0.134 0.205 0.213 0.063 0.181 0.305 0.369 0.047 0.228 0.451 0.580 0.495 0.495 0.407 0.532 0.524 0.672 0.525 0.462 0.658 0.828 0.82 1.13 0.462 0.918 1.07 1.16 1.27 1.40

1.6

1.2

y x 106

T (K)

Ethanol1)

CO2 313.2 K CO2 323.2 K CO2 333.2 K EtOH 313.2 K EtOH 323.2 K EtOH 333.2 K

0.8

0.4

0 100

Synonyms: b,b-Carotene; C. I. Food Orange 5 Source: Sovova, H.; Stateva, R. P.; Galushko, A. A. J. Supercrit. Fluids (2001), 21(3), 195-203.

CAT4240—CHAPTER 3—1/11/2006—17:28—SRIDHAR—XML MODEL C – pp. 151–270

200 P (bar)

300

Solubility Data C

175

[C-39]

b-Carotene (C40H56; MW=536.87) T (K)

P (bar)

Oil1)

Veg (wt%)

y2) x 106

0.8

200 0.31 0.228 313.2 K 220 0.39 0.241 323.2 K 230 0.43 0.260 333.2 K 250 0.53 0.260 0.6 280 0.67 0.337 323.2 190 0.19 0.263 200 0.23 0.241 220 0.32 0.376 0.4 250 0.48 0.422 280 0.66 0.512 283 0.67 0.520 333.2 200 0.15 0.333 220 0.24 0.384 0.2 250 0.39 0.503 150 200 250 260 0.46 0.694 P (bar) 280 0.59 0.732 283 0.61 0.747 1: Vegetable oil that was used as a cosolvent in CO2. 2: Some solubility data were obtained by averaging the original data at the same condition. Synonyms: b,b-Carotene; C. I. Food Orange 5 Source: Sovova, H.; Stateva, R. P.; Galushko, A. A. J. Supercrit. Fluids (2001), 21(3), 195-203.

y x 106

313.2

[C-40]

b -Carotene (C40H56; MW=536.87)

6

0.6

y x 10

Mass T (K) P1) (bar) ratio2) (b - y1,3) x 106 car/cap) 298.15 106 1:1 0.30 143 1:1 0.31 168 1:1 0.31 186 1:1 0.29 219 1:1 0.24 261 1:1 0.27 161 2:1 0.29 204 2:1 0.29 277 2:1 0.24 313.15 100 1:1 0.06 100 1:1 0.20 142 1:1 0.42 174 1:1 0.41 200 1:1 0.56 235 1:1 0.40 254 1:1 0.58 266 1:1 0.43 273 1:1 0.54

300

0.4

0.2

298.15 K , 1:1 298.15 K , 2:1 313.15 K , 1:1 313.15 K , 2:1

0.0 0

100

CAT4240—CHAPTER 3—1/11/2006—17:28—SRIDHAR—XML MODEL C – pp. 151–270

200 P (bar)

300

400

176

Solubility in Supercritical Carbon Dioxide

306 1:1 0.43 314 1:1 0.46 130 2:1 0.29 165 2:1 0.51 205 2:1 0.60 233 2:1 0.51 274 2:1 0.45 305 2:1 0.58 1: Obtained by digitizing the graph in the original article. 2. The mass ratio of b -carotene and capsaicin in the feed. 3: Solubility of b -carotene was measured from the binary mixture of b -carotene and capsaicin. Synonyms: b,b-Carotene; C. I. Food Orange 5 Source: Skerget, M.; Knez, Z. J. Agric. Food Chem. (1997), 45(6), 2066-2069.

Carvacrol (C10H14O; MW=150.22) 1)

[C-41]

6

y x 10 H2 O 313 92 sat'd 2000 104 sat'd 13000 60000 152 sat'd 21000 154 sat'd 20000 156 sat'd 22000 204 sat'd 35000 205 sat'd 33000 30000 208 sat'd 28000 212 sat'd 32000 268 sat'd 42000 280 sat'd 40000 300 sat'd 52000 0 302 sat'd 54000 0 304 sat'd 48000 305 sat'd 55000 308 sat'd 50000 1: Cosolvent water saturated in CO2. Synonyms: 5-Isopropyl-2-methylphenol; 5-Isopropyl-o-cresol Source: Leeke, G.; Gaspar, F.; Santos, R. Ind. Eng. Chem. Res. (2002), 41(8), 2033-2039. P (bar)

y x 10

6

T (K)

100

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200 P (bar)

300

400

Solubility Data C

P (bar)

312.15 62.1 68.9 75.8 79.3 82.7 86.2 322.15 62.1 68.9 75.8 82.7 89.6 93.1 96.5

[C-42]

6

y x 10 90 136 331 400 1411 17046 92 150 198 349 409 757 1571

100000 312.15 K 322.15 K

10000 6

T (K)

(C10H14O; MW=150.22)

y x 10

L -Carvone

177

1000 100 10 60

80 P (bar)

Synonym: (R)-(−)-Carvone; (R)-(−)-pMentha-6,8-dien-2-one Source: Kim, K. H.; Hong, J. Fluid Phase Equil. (1999), 164(1), 107-115. (The numerical data were directly obtained from the authors.)

Castor oil1)

[C-43] 6

y x 10

1: Cold pressed vegetable oil selling at a pharmacy. Source: Eissler, R.; Friedrich, J. P. J. Am. Oil Chem. Soc. (1988), 65(5), 764-767.

1500 6

320 1120 1100

y x 10

T (K) P (bar) 345.15 344.7 551.6 689.5

100

750

0 300

500 P (bar)

CAT4240—CHAPTER 3—1/11/2006—17:28—SRIDHAR—XML MODEL C – pp. 151–270

700

178

Solubility in Supercritical Carbon Dioxide

Catechin (C15H14O6; MW=290.27)

[C-44]

1)

Ethanol y x 106 (mol %) 4000 313 90 5 36 100 5 37 110 5 107 3000 120 5 222 130 5 439 80 10 144 90 10 150 2000 100 10 222 110 10 553 80 15 275 90 15 343 1000 100 15 543 110 15 1073 80 20 601 90 20 899 0 100 20 2169 70 80 25 968 90 25 3206 80 1509 30 1 : Cosolvent in CO2. Synonyms: (+)-Catechin; (+)-(2R,3S )-5,7,3',4'-Tetrahydroxyflavan-3-ol Source: Berna, A.; Chafer, A.; Monton, J. B.; Subirats, S. J. Supercrit. Fluids (2001), 20(2), 157-162. P (bar)

5 mol% 10 mol% 15 mol% 20 mol% 25 mol% 30 mol%

y x 10

6

T (K)

100

130

P (bar)

[C-45]

Cerium tetrakis(2,2,6,6-tetramethyl-3,5-heptanedionate) (C44H76CeO8; FW=873.20)

323

101.2 123.8 144.2 164.9 185.0 214.4 241.3 270.8 298.7 326.8 350.9 117.7 124.0 141.8 162.1 182.9 203.1 230.3 259.4 285.6

y x 106 50 100 140 170 200 230 250 260 270 280 290 60 80 140 200 250 300 340 380 410

313 K 323 K 333 K

600

6

313

P (bar)

y x 10

T (K)

400

200

0 50

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150

250 P (bar)

350

Solubility Data C

333

316.8 347.5 133.1 152.9 176.2 196.8 222.7 252.9 278.8 306.0 345.9

179

440 450 50 110 230 320 420 500 550 590 620

Synonym: Ce(thd)4; Tetrakis(2,2,6,6-tetramethyl-3,5heptanedionato)cerium Source: Andersen, W. C.; Sievers, R. E.; Lagalante, A. F.; Bruno, T. J. J. Chem. Eng. Data (2001), 46(5), 1045-1049.

Cerium tetrakis(2,2,7-trimethyl-3,5-octanedionate) (C44H76CeO8; FW=873.20) 9000

6

y x 10 1530 1870 2780 3950 4070 1630 2000 3090 4630 6220 7840 1670 2990 4220 6080

313 K 323 K 333 K

6000

y x 10

T (K) P (bar) 313 98.0 104.3 121.9 145.3 169.3 323 125.4 128.2 148.4 178.9 199.9 243.0 333 145.4 168.2 186.0 214.6

[C-46]

6

3000

0 50

Synonyms: Ce(tod)4; Tetrakis(2,2,7trimethyl-3,5-octanedionato)cerium Source: Andersen, W. C.; Sievers, R. E.; Lagalante, A. F.; Bruno, T. J. J. Chem. Eng. Data (2001), 46(5), 1045-1049.

150 P (bar)

Cetyl alcohol (C16H34O; MW=242.44)

[C-47]

6

4000 y x 106

y x 10 T (K) P (bar) 308.15 89 1010 109 1640 128 2090 158 2490 187 2700 218 2870 Synonyms: 1-Hexadecanol; Palmityl alcohol Source: Iwai, Y.; Fukuda, T.; Koga, Y.; Arai, Y. J. Chem. Eng. Data (1991), 36(4), 430-432.

250

2000

0 50

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150 P (bar)

250

180

Solubility in Supercritical Carbon Dioxide

Cetyl alcohol (C16H34O; MW=242.44)

99

197

Ethanol (mol%)

0.00 0.40 1.15 1.45 0.00 0.26 0.30 0.35 0.94 1.02 1.03 1.79 2.06 2.95 3.20 3.41 3.43

y x 106 133 143 224 274 275 290 323 292 364 384 370 508 492 640 672 611 590

900 99 bar 197 bar

600 6

308.2

P (bar)

[C-48]

y x 10

T (K)

1)

300

0 0

1

2

3

4

Ethanol (mol%)

1: Cosolvent in CO2. Synonyms: 1-Hexadecanol; Palmityl alcohol Source: Koga, Y.; Iwai, Y.; Hata, Y.; Yamamoto, M.; Arai, Y. Fluid Phase Equil. (1996), 125, 115-128.

[C-49]

Cetyl alcohol (C16H34O; MW=242.44) 106

30000

20000

318 K 328 K 338 K

y x 106

yx T (K) P (bar) 318 152.1 4370 161.8 4860 197.1 6970 221.0 8040 292.5 11300 309.5 12400 415.1 15300 328 141.8 2670 192.6 6210 220.3 8260 301.1 18100 415.9 25300 338 147.1 1900 169.8 3520 195.7 6070 223.2 8980 287.0 15500 373.0 28100 Synonyms: 1-Hexadecanol; Palmityl alcohol Source: Kramer, A.; Thodos, G. J. Chem. Eng. Data (1988), 33(3), 230-234.

10000

0 100

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200

300 P (bar)

400

Solubility Data C

181

Cetyl alcohol (C16H34O; MW=242.44)

[C-50]

106

10000 308 K 318 K 323 K 328 K

7500 y x 106

yx T (K) P (bar) 250 308 50.0 380 68.8 1460 92.0 2100 113.8 2900 134.0 3200 153.8 3700 165.5 4300 175.0 4950 203.7 340 318 50.0 400 69.6 1060 85.5 2410 113.4 3600 133.0 4650 153.8 5710 174.8 7430 201.3 350 323 52.7 400 70.0 410 85.5 1460 112.7 3430 133.8 4600 154.4 6640 174.8 8730 200.6 380 328 52.2 320 69.0 350 88.4 930 111.7 2690 133.1 3930 154.4 6120 182.4 203.0 9060 Synonyms: 1-Hexadecanol; Palmityl alcohol Source: Yau, J.; Tsai, F. J. Chem. Eng. Data (1992), 37(3), 285-287.

5000

2500

0 0

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100 P (bar)

200

182

Solubility in Supercritical Carbon Dioxide

Cetyl alcohol (C16H34O; MW=242.44) P (bar)

yx 106 (mol%) 308.2 99 0.00 133 0.19 148 1.19 238 1.20 243 1.79 324 2.30 379 2.89 461 3.11 491 3.24 576 4.04 650 197 0.00 275 0.98 381 1.03 366 2.67 620 2.74 593 3.99 892 4.07 803 4.08 808 1: Cosolvent in CO2. Synonyms: 1-Hexadecanol; Palmityl alcohol Source: Koga, Y.; Iwai, Y.; Hata, Y.; Yamamoto, M.; Arai, Y. Fluid Phase Equil.(1996), 125, 115-128.

99 bar 197 bar

900

y x 106

T (K)

[C-51]

Octane1)

600

300

0 0

4

2 Octane (mol%)

Chloramphenicol (C11H12Cl2N2O5; MW=323.13)

[C-52]

106

y x 106

yx T (K) P (bar) 313.15 141 5.40 174 7.49 209 8.66 256 9.73 272 9.72 318 10.6 356 11.4 388 11.9 433 13.2 461 12.7 333.15 140 1.44 167 5.62 203 8.43 235 10.8 269 12.9 301 14.8 343 16.4 391 18.1 430 19.5 463 20.7 Synonym: 2,2-Dichloro-N-((1R,2R)-1,3-dihydroxy-1(4-nitrophenyl)propan-2-yl)acetamide Source: Li, S.; Maxwell, R. J.; Shadwell, R. J. Fluid Phase Equil.(2002), 198(1), 67-80.

25 313.15 K 333.15 K

20 15 10 5 0 0

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200

400 P (bar)

600

Solubility Data C

183

Chlorobenzene (C6H5 Cl; MW=112.56)

[C-53]

106

y x 106

yx T (K) P (bar) 313.2 60.9 4800 60.9 4900 60.9 5000 65.4 3900 70.9 5400 75.9 6200 75.4 6600 353.2 60.9 14200 79.9 11700 100.9 17200 101.3 16700 101.4 16900 120.9 28500 130.9 50100 131.4 50900 393.1 61.1 27100 80.9 27000 80.9 27100 100.9 30700 100.9 30000 120.9 35200 120.9 36300 140.9 45900 140.9 45100 160.8 67200 161.1 66900 Source: Walther, D.; Maurer, G. Ber. Bunsenges. Phys. Chem. (1992), 96(8), 981-988.

80000 313.2 K 353.2 K

60000

393.1 K

40000

20000

0 50

90

130 P (bar)

2-Chlorobiphenyl (C12H9Cl; MW=188.66) P (bar) 100 110 120 130 140 150 160 170 180 190 200 220 240 260 280 300 323 100 110 120

y x 106 1150 1510 1810 2000 2210 2400 2580 2710 2830 2920 3070 3160 3260 3380 3550 3710 344 682 1110

[C-54] 5000 313 K 323 K 333 K

4000

y x 106

T (K) 313

170

3000 2000 1000 0

50

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150

P (bar)

250

350

184

Solubility in Supercritical Carbon Dioxide

130 1500 140 1820 150 2090 160 2330 170 2540 180 2770 190 2910 200 3060 220 3380 240 3660 260 3980 280 4180 300 4330 333 100 243 110 346 120 574 130 859 140 1180 150 1520 160 1850 170 2140 180 2380 190 2630 200 2910 220 3340 240 3750 260 4130 280 4420 300 4790 Source: Anitescu, G.; Tavlarides, L. L. J. Supercrit. Fluids (1999), 14(3), 197-211.

2-Chlorobiphenyl (C12H9Cl; MW=188.66) T (K)

P (bar)

313

100 110 120 130 140 150 160 170 180 190 200 220 240 260

n-Butane1) (mol%) 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0

y x 106 1420 1860 2170 2370 2600 2790 2970 3090 3210 3310 3430 3570 3670 3800

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[C-55]

Solubility Data C

185

323

333

5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0

3910 4020 513 948 1450 1900 2260 2550 2810 3030 3270 3420 3590 3910 4190 4490 4700 4900 401 567 869 1230 1620 2020 2410 2930 3000 3280 3580 4060 4490 4910 5240 5610

6000 313 K 323 K 333 K

4000 y x 106

280 300 100 110 120 130 140 150 160 170 180 190 200 220 240 260 280 300 100 110 120 130 140 150 160 170 180 190 200 220 240 260 280 300

2000

0 50

150

250

350

P (bar)

1: Cosolventin CO2. Source: Anitescu, G.; Tavlarides, L. L. J. Supercrit. Fluids (1999), 14(3), 197-211.

2-Chlorobiphenyl (C12H9Cl; MW=188.66) T (K)

P (bar)

313

100 110 120 130 140 150 160 170 180 190

Methanol1) (mol%) 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0

yx 106 1360 1770 2060 2310 2540 2720 2900 3030 3140 3210

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[C-56]

186

Solubility in Supercritical Carbon Dioxide

313 K 323 K 333 K

y x 106

200 5.0 3320 220 5.0 3440 240 5.0 3550 260 5.0 3660 6000 280 5.0 3790 300 5.0 3900 323 100 5.0 485 110 5.0 925 120 5.0 1400 4000 130 5.0 1820 140 5.0 2140 150 5.0 2430 160 5.0 2680 170 5.0 2910 2000 180 5.0 3120 190 5.0 3290 200 5.0 3430 220 5.0 3750 240 5.0 4040 260 5.0 4300 0 280 5.0 4520 50 300 5.0 4720 333 100 5.0 346 110 5.0 526 120 5.0 825 130 5.0 1180 140 5.0 1590 150 5.0 1970 160 5.0 2330 170 5.0 2640 180 5.0 2910 190 5.0 3180 200 5.0 3460 220 5.0 3930 240 5.0 4350 260 5.0 4730 280 5.0 5070 300 5.0 5410 1: Cosolvent in CO2. Source: Anitescu, G.; Tavlarides, L. L. J. Supercrit. Fluids (1999), 14(3), 197-211.

4-Chlorobiphenyl (C12H9Cl; MW=188.66) T (K) P (bar) 313 100 110 120 130 140 150 160

y x 106 1600 2320 3010 3480 4020 4470 4980

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150

P (bar)

250

350

[C-57]

Solubility Data C

187

313 K 323 K 333 K

y x 106

170 5350 180 5570 190 6030 200 6480 16000 220 6820 240 7200 260 7810 280 8260 12000 300 8860 323 100 357 110 899 120 1730 8000 130 2630 140 3440 150 4150 4000 160 4860 170 5460 180 6320 190 6670 0 200 7220 50 220 8190 240 9180 260 10400 280 11100 300 11900 333 100 267 110 442 120 859 130 1460 140 2240 150 3170 160 4170 170 5080 180 5830 190 6730 200 7750 220 9400 240 10800 260 12700 280 13900 300 15400 Source: Anitescu, G.; Tavlarides, L. L. J. Supercrit. Fluids (1999), 14(3), 197-211. 4-Chlorobiphenyl (C12H9Cl; MW=188.66) T (K) 313

P (bar) 100 110 120

n-Butane1) (mol%) 5.0 5.0 5.0

y x 106 2190 3100 3930

CAT4240—CHAPTER 3—1/11/2006—17:28—SRIDHAR—XML MODEL C – pp. 151–270

150

250

350

P (bar)

[C-58]

188

Solubility in Supercritical Carbon Dioxide

313 K 323 K 333 K

y x 106

130 5.0 4500 140 5.0 5130 150 5.0 5680 160 5.0 6270 20000 170 5.0 6710 180 5.0 7070 190 5.0 7550 200 5.0 7960 15000 220 5.0 8510 240 5.0 9030 260 5.0 9580 280 5.0 10000 10000 300 5.0 10500 323 100 5.0 671 110 5.0 1420 5000 120 5.0 2380 130 5.0 3390 140 5.0 4280 150 5.0 5070 0 160 5.0 5850 50 170 5.0 6520 180 5.0 7290 190 5.0 7880 200 5.0 8550 220 5.0 9660 240 5.0 10800 260 5.0 12000 280 5.0 13100 300 5.0 14100 333 100 5.0 470 110 5.0 751 120 5.0 1340 130 5.0 2050 140 5.0 2900 150 5.0 3890 160 5.0 4980 170 5.0 5930 180 5.0 6770 190 5.0 7750 200 5.0 8870 220 5.0 10800 240 5.0 12700 260 5.0 14500 280 5.0 16000 300 5.0 17400 1: Cosolventin CO2. Source: Anitescu, G.; Tavlarides, L. L. J. Supercrit. Fluids (1999), 14(3), 197-211.

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150

250 P (bar)

350

Solubility Data C

189

4-Chlorobiphenyl (C12H9Cl; MW=188.66) P (bar)

313

100 110 120 130 140 150 160 170 180 190 200 220 240 260 280 300 100 110 120 130 140 150 160 170 180 190 200 220 240 260 280 300 100 110 120 130 140 150 160 170 180 190 200 220

323

333

(mol%)

5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0

[C-59]

y x 106 2070 2920 3750 4310 4900 5420 5910 6290 6640 7000 7300 7720 8140 8630 9090 9670 535 1250 2290 3310 4200 4940 5800 6430 7150 7760 8280 9480 10500 11600 12600 13500 435 681 1250 1980 2830 3800 4800 5790 6610 7600 8710 10500

20000 313 K 323 K 333 K

15000 y x 106

T (K)

Methanol1)

10000

5000

0 50

CAT4240—CHAPTER 3—1/11/2006—17:28—SRIDHAR—XML MODEL C – pp. 151–270

150

P (bar)

250

350

190

Solubility in Supercritical Carbon Dioxide

240 5.0 12400 260 5.0 14100 280 5.0 15600 300 5.0 16900 1: Cosolvent in CO2. Source: Anitescu, G.; Tavlarides, L. L. J. Supercrit. Fluids (1999), 14(3), 197-211.

2-Chloro-1-methylbenzene (C7H7Cl; MW=126.58)

[C-60]

y x 106 1800 1800 1900 1900 2100 2200 3400 5000 4800 5800 5700 8800 8400 16100 15500 16400 16000 31700 32400 14000 13900 15300 14600 15100 16300 17000 21200 18900 26900 27300 27300 38100 38400 46700 47200 46400

50000 313.2 K 353.1 K

40000

y x 106

T (K) P (bar) 313.2 60.9 60.9 65.9 65.9 70.9 70.9 75.9 353.1 60.9 60.9 80.9 80.9 100.9 100.9 120.9 120.9 120.9 120.9 135.9 135.9 393.2 60.9 60.9 80.9 80.9 80.9 100.9 100.9 120.9 120.9 140.9 140.9 140.9 160.8 160.8 170.8 170.9 170.9

393.2 K

30000 20000 10000 0 50

Source: Walther, D.; Maurer, G. Ber. Bunsenges. Phys. Chem. (1992), 96(8), 981-988.

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100 P (bar)

150

Solubility Data C

191

p-Chlorophenol (C6H5ClO; MW=128.56)

[C-61]

106

y x 106

yx T (K) P (bar) 40000 309.2 81.0 5960 90.3 9730 101.2 10990 111.2 13030 20000 121.7 14060 131.3 15830 142.9 17480 152.9 20310 0 169.9 20470 0 203.3 27890 239.8 32890 Synonym: 4-Chlorophenol Source: Van Leer, R. A.; Paulaitis, M. E. J. Chem. Eng. Data (1980), 25(3), 257-259.

100

200 P (bar)

Chlorophyllian pigments1) T (K) P2) (bar) 307.7

120 150 200

S2)

103

x (g/L) 7.4 17.2 30.6

300

[C-62]

w3) x 106 9.5 20.9 35.2

1: Extracted from marine alga(Dilophus Spiralis). 2: Obtained by digitizing the graph in the original article. 3: Calculated from S. Source: Subra, P.; Tufeu, R. J. Supercrit. Fluids (1990), 3(1), 20-22.

2-Chloropyrimidine (C4H3ClN2; MW=114.53)

[C-63]

106

y x 106

yx T (K) P (bar) 308.15 63.2 913 20000 71.5 1260 79.8 3610 84.4 5400 10000 92.3 9700 95.5 10950 99.7 11840 125.1 15570 0 141.5 17550 50 159.3 18830 177.8 19870 Synonym: 2-Chloro-1,3-pyrimidine Katayama, T. J. Chem. Eng. Data (1991), 36(3), 314-316. Source: Nakatani, T.; Tondo, T.; Ohgaki, K.;

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100

150 P (bar)

200

192

Solubility in Supercritical Carbon Dioxide

Cholesterol (C27H46O; MW=386.65) T(K)

P(bar)

S (g/L)

y1)

x

[C-64]

106

313.15 K 333.15 K

300 y x 106

81.1 0.000 0.0 101.3 0.078 13.8 55.0 121.6 0.350 138.0 152.0 0.950 317.0 202.7 2.350 333.15 101.3 0.000 0.0 121.6 0.006 1.5 152.0 0.280 52.0 202.7 2.360 368.0 353.15 121.6 0.000 0.0 152.0 0.025 6.5 204.0 202.7 1.080 1: Calculated from S. Synonym: Cholest-5-en-3b-ol Source: Chrastil, J. J. Phys. Chem. (1982), 86(15), 3016-3021.

400

313.15

353.15 K

200 100 0 50

100

150 P (bar)

Cholesterol (C27H46O; MW=386.65)

[C-65]

150 313.15 K 318.15 K 323.15 K 333.15 K

100 y x 106

y x 106 T (K) P (bar) 313.15 100 12.9 130 34.6 160 49.0 190 68.5 220 79.1 250 93.7 318.15 100 6.5 120 24.0 140 37.2 160 57.6 180 70.9 210 79.2 240 94.0 323.15 100 2.3 130 25.3 160 50.0 190 73.0 220 97.0 250 124.0 333.15 130 10.6 160 43.0 190 80.0 220 112.0 250 145.0 Synonym: Cholest-5-en-3b-ol Source: Huang, Z.; Kawi, S.; Chiew, Y. C. J. Supercrit. Fluids (2004), 30(1), 25-39.

200

50

0 50

CAT4240—CHAPTER 3—1/11/2006—17:28—SRIDHAR—XML MODEL C – pp. 151–270

150 P (bar)

250

Solubility Data C

193

Cholesterol (C27H46O; MW=386.65)

[C-66]

106

150 313.15 K 323.15 K 333.15 K

100 y x 106

yx T (K) P (bar) 313.15 100 12.9 130 34.6 160 49.0 190 68.5 220 79.1 250 93.7 323.15 100 2.3 130 25.3 160 50.0 190 73.0 220 97.0 250 124.0 333.15 130 10.6 160 43.0 190 80.0 220 112.0 250 145.0 Synonym: Cholest-5-en-3b-ol Source: Yun, S. L. J.; Liong, K. K.; Gurdial, G. S.; Foster, N. R.Ind. Eng. Chem. Res. (1991), 30(11), 2476-2482.

50

0 50

150 P (bar)

Cholesterol (C27H46O; MW=386.65)

313.15

113 135 178 237

313.15

103 135 175 207 242

313.15

92 135 175 207 237

313.15

102 135

0.0 0.0 0.0 0.0 Acetone 3.0 3.0 3.0 3.0 3.0 Methanol 3.0 3.0 3.0 3.0 3.0 Water 3.0 3.0

[C-67]

y1) x 106 38 94 100 130 63 81 250 380 500 130 250 380 500 560 0 8

600 Pure CO2 Acetone Methanol Water

400 y x 106

T (K)

Cosolvent P (bar) (wt%)

250

200

0 50

CAT4240—CHAPTER 3—1/11/2006—17:28—SRIDHAR—XML MODEL C – pp. 151–270

150 P (bar)

250

194

Solubility in Supercritical Carbon Dioxide

165 3.0 20 230 3.0 50 1: Obtained by digitizing the graph in the original article. Some data may have large reading errors of more than 10% as the original graph is in a semi-log scale with a small span. Synonym: Cholest-5-en-3b-ol Source: Noh, M. J.; Kim, T. G.; Hong, I. K.; Yoo, K.P.Korean J. Chem. Eng. (1995), 12(1), 48-55.

Cholesterol (C27H46O; MW=386.65)

308.15

123.6 153.9 182.7 203.0 253.6 257.6 278.9 100.8 123.2 154.2 183.3 203.6 254.3 277.1 101.0 121.8 152.0 204.4 254.0 304.1 354.3

313.15

104.6 121.5 153.2 184.9 203.9 253.8 277.6 100.9 122.7 152.0 184.5

0.0 0.0 0.0 0.0 0.0 0.0 0.0 Acetone 3.5 3.5 3.5 3.5 3.5 3.5 3.5 Ethanol 3.5 3.5 3.5 3.5 3.5 3.5 3.5 Methanol 3.5 3.5 3.5 3.5 3.5 3.5 3.5 0.0 0.0 0.0 0.0

[C-68]

y x 106 13.9 26.1 30.7 41.5 51.9 52.5 55.5 67.0 79.2 101.0 146.0 159.0 224.0 283.0 34.4 52.8 65.4 96.5 109.0 128.0 148.0 94.4 120.0 193.0 238.0 275.0 355.0 427.0 70.8 86.9 97.4 126.0

500

CO2, 308.2 K CO2, 313.2 K CO2, 333.2 K Acet, 308.2 K EtOH, 308.2 K MeOH, 308.2 K

400

y x 106

T (K)

Cosolvent P (bar) (mol%)

300 200 100 0 0

100

CAT4240—CHAPTER 3—1/11/2006—17:28—SRIDHAR—XML MODEL C – pp. 151–270

200 P (bar)

300

400

Solubility Data C

195

203.5 154.0 0.0 252.7 0.0 192.0 276.0 0.0 250.0 333.15 101.0 0.0 29.1 121.5 0.0 59.7 151.5 0.0 90.0 182.2 0.0 136.0 203.4 0.0 200.0 253.6 0.0 324.0 273.3 0.0 380.0 Synonym: Cholest-5-en-3-ol Source: Wong, J. M.; Johnston, K. P. Biotech. Progr. (1986), 2(1), 29-39.

[C-69]

Cholesterol (C27H46O; MW=386.65) P (bar)

y x 106 37.6 61.8 84.6 106.0 123.0 136.0 156.0 40.0 76.2 112.0 142.0 172.0 212.0 57.2 99.4 152.0 199.0 255.0 113.0 195.0 251.0 306.0 377.0

400 318 K (3.5%) 328 K (3.5%) 338 K (3.5%) 338 K (6.0%)

y x 106

Acetone1) (mol %) 318 100 3.5 120 3.5 140 3.5 160 3.5 180 3.5 200 3.5 220 3.5 328 120 3.5 140 3.5 160 3.5 180 3.5 200 3.5 220 3.5 338 140 3.5 160 3.5 180 3.5 200 3.5 220 3.5 140 6.0 160 6.0 180 6.0 200 6.0 220 6.0 1: Cosolvent in CO2. T (K)

200

0 50

Synonym: Cholest-5-en-3b-ol Source: Foster, N. R.; Singh, H.; Yun, S. L. J.; Tomasko, D. L.; Macnaughton, S. J. Ind. Eng. Chem. Res. (1993), 32(11), 2849-2853.

CAT4240—CHAPTER 3—1/11/2006—17:28—SRIDHAR—XML MODEL C – pp. 151–270

150 P (bar)

250

196

Solubility in Supercritical Carbon Dioxide

Cholesterol (C27H46O; MW=386.65)

313

[C-70]

w x 106 850 1300 1300 1800

2000 y x 106

Cosolvent T (K) P (bar) (wt%) Acetone 313 180 9.4 14.5 Ethanol 313 180 9.3 14.3 CH2 Cl2

1500 Acetone Ethanol CH2Cl2

1000 500

180

12.4 970 22.0 1740 Synonym: Cholest-5-en-3b-ol Fanovich, M. A., Elvira, C., Subra, P., J. Appl. Polym. Sci., 90(13), 3652-3659, (2003). Source: Domingo, C., Vega, A.,

0

10

20

Cosolvent (wt%)

Cholesterol (C27H46O; MW=386.65)

[C-71]

Acetone, 318.15 K Acetone, 328.15 K Methanol, 318.15 K Methanol, 328.15 K

200 y x 106

Cosolvent T (K) P (bar) y x 106 (mol%) Acetone 3.0 318.15 100 37.3 3.0 120 60.8 3.0 140 82.6 3.0 160 101.0 3.0 180 116.0 3.0 210 141.0 3.0 240 154.0 3.0 328.15 120 40.5 3.0 140 77.1 3.0 160 106.0 3.0 180 124.0 3.0 210 175.0 240 218.0 3.0 Methanol 3.0 318.15 100 25.3 3.0 120 59.2 3.0 140 82.0 3.0 160 96.1 3.0 180 117.0 3.0 210 135.0 3.0 240 160.0 3.0 328.15 120 24.9 3.0 140 59.5 3.0 160 95.7 3.0 180 113.0 3.0 210 147.0 240 175.0 3.0 Synonym: Cholest-5-en-3b-ol Source: Huang, Z.; Kawi, S.; Chiew, Y. C. J. Supercrit. Fluids (2004), 30(1), 25-39.

30

100

0 50

CAT4240—CHAPTER 3—1/11/2006—17:28—SRIDHAR—XML MODEL C – pp. 151–270

150 P (bar)

250

Solubility Data C

197

Cholesterol (C27H46O; MW=386.65) T (K)

P (bar)

[C-72]

Ethane1)

y x 106

y x 106

y x 106 (mol %) 308.1 85 50.0 8.0 100 50.0 20.0 120 50.0 40.4 140 50.0 63.7 160 50.0 89.0 190 50.0 128.0 220 50.0 164.0 318.1 100 50.0 11.1 120 50.0 30.0 130 50.0 43.7 140 50.0 57.1 160 50.0 90.1 190 50.0 145.0 220 50.0 198.0 338.1 85 50.0 12.5 100 50.0 38.2 120 50.0 97.9 140 50.0 173.0 160 50.0 266.0 190 50.0 403.0 328.1 85 3.5 23.9 100 3.5 54.8 120 3.5 107.0 140 3.5 167.0 160 3.5 230.0 190 3.5 334.0 100 14.0 31.9 120 14.0 70.1 140 14.0 130.0 160 14.0 190.0 190 14.0 295.0 220 14.0 398.0 120 50.0 18.6 140 50.0 44.9 160 50.0 86.1 190 50.0 161.0 220 50.0 241.0 120 96.5 7.4 140 96.5 21.9 160 96.5 46.3 190 96.5 80.1 220 96.5 118.0 1: Cosolvent in CO2 on a solute-free basis. Synonym: Cholest-5-en-3b-ol Source: Singh, H.; Yun, S. L. J.; Macnaughton, S. J.; Tomasko, D. L.; Foster, N. R. Ind. Eng. Chem. Res. (1993), 32(11), 2841-2848.

308.1 K 318.1 K 328.1 K 338.1 K

400

Ethane 50%

200

0 50

150 P (bar)

250

120 bar 140 bar 160 bar 190 bar 220 bar

400

328.1

200

0 0

20

CAT4240—CHAPTER 3—1/11/2006—17:28—SRIDHAR—XML MODEL C – pp. 151–270

40

60

Ethane (mol %)

80

100

198

Solubility in Supercritical Carbon Dioxide

Cholesterol (C27H46O; MW=386.65) T (K)

P (bar)

Hexane1) (mol %)

[C-73]

y x 106

318

318 K (3.5%) 328 K (3.5%) 338 K (3.5%) 338 K (6.0%)

400

y x 106

90 3.5 18.5 110 3.5 59.8 130 3.5 84.7 150 3.5 105.0 170 3.5 131.0 200 3.5 176.0 328 110 3.5 34.4 130 3.5 80.2 150 3.5 116.0 170 3.5 142.0 200 3.5 193.0 338 110 3.5 12.1 130 3.5 51.7 150 3.5 107.0 170 3.5 151.0 200 3.5 194.0 140 6.0 144.0 160 6.0 228.0 180 6.0 330.0 200 6.0 418.0 220 6.0 483.0 1: Cosolvent in CO2. Synonym: Cholest-5-en-3b-ol Source: Foster, N. R.; Singh, H.; Yun, S. L. J.; Tomasko, D. L.; Macnaughton, S. J. Ind. Eng. Chem. Res. (1993), 32(11), 2849-2853.

200

0 40

120 P (bar)

Cholesterol (C27H46O; MW=386.65) T (K)

P (bar)

N2O1) (vol %)

[C-74]

y x 106

300

328.2

y x 106

102.5 0.0 6.1 123.4 0.0 43.8 155.1 0.0 90.0 187.8 0.0 131.2 206.9 0.0 167.8 254.8 0.0 218.1 275.7 0.0 276.7 333.2 104.0 0.0 19.9 185.8 0.0 143.3 252.7 0.0 293.4 108.9 10.0 20.2 123.4 10.0 47.6 183.7 10.0 184.3 204.9 10.0 231.8 250.5 10.0 288.5 1. Cosolvent in CO2. Synonym: Cholest-5-en-3b-ol Source: Kosal, E.; Lee, C. H.; Holder, G. D. J. Supercrit. Fluids (1992), 5(3), 169-179.

200

CO2 328.2 K CO2 333.2 K w/N2O 333.2 K

200

100

0 50

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150 P (bar)

250

Solubility Data C

199

Cholesterol acetate (C29H48O2; MW=428.69)

[C-75]

106

1200 308.15 K 318.15 K 328.15 K

800 y x 106

yx T (K) P (bar) 308.15 91 79.2 100 118.0 120 186.0 140 257.0 160 337.0 180 427.0 210 455.0 240 527.0 318.15 90 4.4 100 29.9 110 75.5 120 120.0 140 207.0 160 385.0 180 477.0 210 633.0 240 819.0 328.15 110 16.2 120 50.1 140 176.0 160 358.0 180 546.0 190 692.0 210 1040.0 Synonym: Cholesteryl acetate Source: Huang, Z.; Kawi, S.; Chiew, Y. C. J. Supercrit. Fluids (2004), 30(1), 25-39.

400

0 50

150 P (bar)

Cholesterol benzoate (C34H50O2; MW=490.76)

[C-76]

60 308.15 K 318.15 K 328.15 K

40 y x 106

T (K) P (bar) 308.15 120 140 160 180 210 240 270 318.15 130 160 180 210 240 270 328.15 140 160 180 210 240

y x 106 7.2 7.5 11.7 18.0 18.4 19.8 25.1 6.3 15.1 20.0 24.7 31.5 36.2 5.3 12.6 20.5 28.3 42.3

250

20

0 100

CAT4240—CHAPTER 3—1/11/2006—17:28—SRIDHAR—XML MODEL C – pp. 151–270

200 P (bar)

300

200

Solubility in Supercritical Carbon Dioxide

255 43.9 270 52.8 Synonym: Cholesteryl benzoate Source: Huang, Z.; Kawi, S.; Chiew, Y. C. J. Supercrit. Fluids (2004), 30(1), 25-39.

Cholesterol benzoate(C34H50O2; MW=490.76)

Acetone 3.0 16.4 3.0 26.8 3.0 30.6 3.0 39.5 3.0 48.3 3.0 54.0 3.0 328.15 11.9 3.0 25.8 3.0 33.1 3.0 46.9 3.0 59.6 72.0 3.0 Methanol 3.0 318.15 130 15.3 3.0 160 25.0 3.0 180 31.3 3.0 39.8 210 3.0 50.1 240 3.0 270 55.3 3.0 328.15 140 13.8 3.0 160 22.4 3.0 180 29.8 3.0 210 42.5 3.0 240 57.2 270 61.1 3.0 Synonym: Cholesteryl benzoate Source: Huang, Z.; Kawi, S.; Chiew, Y. C. J. Supercrit. Fluids (2004), 30(1), 25-39. 318.15

130 160 180 210 240 270 130 160 180 210 240 270

[C-77]

y x 106

90

y x 106

T (K)

Cosolvent P (bar) (mol%)

60

Acetone 318.15 K Acetone 328.15 K Methanol 318.15 K Methanol 328.15 K

30

0 100

CAT4240—CHAPTER 3—1/11/2006—17:28—SRIDHAR—XML MODEL C – pp. 151–270

200 P (bar)

300

Solubility Data C

201

Cholesterol butyrate (C31H52O2; MW=456.74) yx

107 216 359 432 460 570 581 22 146 258 378 498 672 836 39 145 285 415 605 893

1000 308.15 K 318.15 K 328.15 K

750 y x 106

T (K) P (bar) 308.15 100 120 140 160 180 210 240 318.15 100 120 140 160 180 210 240 328.15 120 140 160 180 210 240

[C-78]

106

500

250

0 50

150

250

P (bar)

Synonyms: Cholesterol butanoate; Cholesteryl butyrate Source: Huang, Z.; Kawi, S.; Chiew, Y. C. J. Supercrit. Fluids (2004), 30(1), 25-39.

Cholesterol (1) + Testosterone (2)Mixture1) 328.2

333.2

P (bar)

y1 x

y2 x

106

122.3 156.6 176.7 210.9 225.0 244.4

54.8 99.9 143.3 177.9 220.3 255.5

4.5 27.2 38.4 80.2 84.2 95.7

158.0 173.7 211.9 227.1 243.9

96.9 138.4 189.1 231.3 266.2

13.6 42.3 86.1 99.7 100.7

[C-79] 300

y x 106

T (K)

106

200

Chol 328.2 K Chol 333.2 K Test 328.2 K Test 333.2 K

100

0 100

1: Solubility of each component was measured from the mixture. Source: Kosal, E.; Lee, C. H.; Holder, G. D. J. Supercrit. Fluids(1992), 5(3), 169-179.

CAT4240—CHAPTER 3—1/11/2006—17:28—SRIDHAR—XML MODEL C – pp. 151–270

150 P (bar)

200

250

202

Solubility in Supercritical Carbon Dioxide

Chromium tris(acetylacetonate) (C15H21Cr6O; MW=349.32) yx

200

17.2 60.7 90.9 112.7 132.5 150.3 170.4 190.9

y x 106

T (K) P (bar) 313.15 103.4 137.9 172.4 206.8 241.3 275.8 310.3 344.7

[C-80]

106

100 0 50

Synonyms: Cr(acac)3; Tris(pentane2,4-dionato)chromium Source: Lagalante,A.F.;Hansen,B.N.;Bruno,T. J.; Sievers, R. E. Inorg. Chem. (1995), 34(23), 57815785.

150

250

Chromium tris(3-bromoacetylacetonate) (C15H18Br3Cr6O; FW=586.01) y x 106

[C-81]

16

5.0 7.5 10.0 12.8 14.7

y x 106

T (K) P (bar) 313.15 103.4 137.9 172.4 206.8 241.3

350

P (bar)

10

Synonyms: Cr(acac-Br)3; Tris(3bromopentane-2,4-dionato)chromium Source: Lagalante, A. F.; Hansen, B. N.; Bruno, T. J.; Sievers, R. E.Inorg. Chem.(1995), 34(23), 5781-5785.

4 50

150

250

P (bar)

Chromium tris(2,2,6,6-tetramethylheptane-3,5-dionate) (C33H57Cr6O; FW=601.81) y x 106 4000 3720 4210 4490 4970 5740 6050

Synonyms: Cr(thd)3; Tris(2,2,6,6tetramethylheptane-3,5dionato)chromium Source: Lagalante, A. F.; Hansen, B. N.; Bruno, T. J.; Sievers, R. E.Inorg. Chem.(1995), 34(23), 5781-5785.

[C-82]

7000 y x 106

T (K) P (bar) 313.15 103.4 137.9 172.4 206.8 241.3 275.8 310.3

5000

3000 50

CAT4240—CHAPTER 3—1/11/2006—17:29—SRIDHAR—XML MODEL C – pp. 151–270

150

250 P (bar)

350

Solubility Data C

203

Chromiumcis-tris(1,1,1-trifluoroacetylacetonate) (C15H12CrF9O6; FW=511.24) yx

673 878 1139 1359 1422 1601 1707 1908

[C-83]

2000 y x 106

T (K) P (bar) 313.15 103.4 137.9 172.4 206.8 241.3 275.8 310.3 344.7

106

1200

400

Synonyms: cis-Cr(tfa)3;cis-Tris(1,1,1trifluoropentane-2,4-dionato)chromium Source: Lagalante, A.F.; Hansen, B.N.; Bruno,T. J.; Sievers, R. E. Inorg. Chem. (1995), 34(23), 5781-5785.

50

150

250

350

P (bar)

Chromiumtrans-tris(1,1,1-trifluoroacetylacetonate) (C15H12CrF9O6; FW=511.24) [C-84]

y x 106

y x 106 T (K) P (bar) 3000 313.15 103.4 1479 137.9 1691 172.4 1773 2000 206.8 1974 241.3 2224 275.8 2506 310.3 2638 1000 344.7 2721 50 Synonyms: trans-Cr(tfa)3; transTris(1,1,1-trifluoropentane-2,4-dionato)chromium Source: Lagalante, A. F.; Hansen, B. N.; Bruno, T. J.; Sievers, R. E. Inorg. Chem. (1995), 34(23), 5781-5785.

150

250 P (bar)

Chrysene (C18H12; MW=228.29)

350

[C-85]

106

y x 106

yx T (K) P (bar) 10 308.15 84 0.73 96 2.03 100 2.44 111 3.24 5 125 4.00 140 4.93 160 5.70 0 182 6.63 0 199 7.35 221 7.82 251 8.84 Synonym: 1,2-Benzophenanthrene Source: Barna,L.; Blanchard, J.M.; Rauzy, E.; Berro, C. J. Chem. Eng. Data (1996), 41(6), 1466-1469.

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100

200 P (bar)

300

204

Solubility in Supercritical Carbon Dioxide

Chrysene (C18H12; MW=228.29) (K) 308.2

P2)

(bar) 91 111 191 238 284

y1)

x

[C-86]

106 0.01 0.06 0.20 0.70 8.50

12 y x 106

T1)

308.2 K 0.80 g/ml

8 4

r = constant (0.80 g/ml) 303 113 1.54 314 170 5.40 323 211 7.61 334 267 6.79 345 322 12.0

0 50

150

250

350

P (bar)

1: Temperature (for constant density data) and solubility were obtained by digitizing the graph in the original article. May have large reading error as the source graph is small. 2: Calculated from temperature and density in the source graph (constant temperature data only). Synonym: 1,2-Benzophenanthrene Source: Burk, R.; Kruus, P.Can. J. Chem. Eng. (1992), 70(2), 1403-1407.

Chrysene (C18H12; MW=228.29)

[C-87]

106

150 313.15 K 323.15 K 343.15 K 373.15 K 393.15 K 423.15 K

100 y x 106

yx T (K) P (bar) 313.15 80 0.40 100 0.45 150 3.96 200 4.83 300 7.55 350 8.00 323.15 80 0.20 100 0.27 150 3.47 200 6.19 300 10.9 350 11.9 343.15 200 8.26 300 21.40 373.15 80 0.42 100 0.77 150 3.67 200 10.8 300 47.2 350 61.3 393.15 200 15.4 300 75.7 423.15 200 28.5 300 148.0 Synonym: 1,2-Benzophenanthrene Source: Lou, X.; Janssen, H.-G.; Cramers, C. A. J. Chromatogr. A (1997),785(1-2), 57-64.

50

0 0

CAT4240—CHAPTER 3—1/11/2006—17:29—SRIDHAR—XML MODEL C – pp. 151–270

100

200 P (bar)

300

400

Solubility Data C

205

Chrysene (C18H12; MW=228.29)

[C-88]

106

313 K 373 K 423 K 473 K 523 K

y x 106

yx T (K) P (bar) 313 250 2.2 300 2.7 350 3.3 400 4.1 450 4.6 373 200 6.0 250 12 4000 300 21 350 27 400 30 3000 450 33 423 200 7.0 250 17 300 35 2000 350 63 400 100 450 150 473 100 6.0 1000 150 25 200 54 250 110 0 300 220 350 410 0 400 650 450 1160 523 100 75 150 230 200 380 250 770 300 1460 350 2290 400 3100 450 3610 Synonym: 1,2-Benzophenanthrene Source: Miller, D.J.; Hawthorne, S.B.; Clifford, A. A.; Zhu, S. J. Chem. Eng. Data (1996), 41(4), 779-786.

200

400 P (bar)

C. I. Disperse Black 9 (C16H20N4O2; MW=300.36) 106

[C-89] 20

y x 106

yx T (K) P (bar) 323.15 202.6 14.0 303.9 15.3 354.6 2.4 373.15 202.6 4.7 303.9 11.8 354.6 5.5 Synonym: 4-Amino-4'-[bis(2hydroxyethyl)amino]azobenzene Source: Draper, S. L.; Montero, G. A.; Smith, B.; Beck, K. Dyes Pigm. (2000), 45(3), 177-183.

600

10

0 150

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323.15 K 373.15 K

250 P (bar)

350

206

Solubility in Supercritical Carbon Dioxide

C. I. Disperse Blue 31) (C17H16N2O3; MW=296.32) 106

40 323.15 K 373.15 K

y x 106

yx T (K) P (bar) 323.15 202.6 4.7 303.9 12.5 354.6 9.6 373.15 202.6 4.1 303.9 25.0 354.6 36.3 1: Mixture with unknown proportion of 2hydroxyethyl and methyl derivatives. synonym: 1,4-Diaminoanthraquinone, N,N '-mixed 2-hydroxyethyl and methyl derivatives Source: Draper, S. L.; Montero, G. A.; Smith, B.; Beck, K. Dyes Pigm. (2000), 45(3), 177-183.

[C-90]

20

0 150

250 P (bar)

C. I. Disperse Blue 31) (C17H16N2O3; MW=296.32)

350

[C-91]

106

323.7 K 353.7 K 383.7 K 413.7 K

y x 106

T (K) P (bar) y x 323.7 105.1 6.1 157.8 10.1 216.1 16.1 261.7 15.8 60 301.5 14.3 353.7 106.5 0.7 158.7 20.0 216.8 35.8 40 245.8 36.2 275.9 30.1 318.1 41.9 383.7 106.2 0.8 20 140.3 8.9 181.8 19.9 226.5 23.3 0 266.0 28.2 318.1 38.2 50 413.7 106.8 0.7 142.1 3.0 187.2 13.6 227.2 27.6 283.7 42.8 63.6 329.8 1: Mixture with unknown proportion of 2-hydroxyethyl and methyl derivatives. Synonym: 1,4-Diaminoanthraquinone, N,N'-mixed 2 hydroxyethyl and methyl derivatives Source: Lee, J.W.; Park, M.W.; Bae, H.K. Fluid Phase Equil.(2000), 173(2), 277-284.

CAT4240—CHAPTER 3—1/11/2006—17:29—SRIDHAR—XML MODEL C – pp. 151–270

150

250 P (bar)

350

Solubility Data C

207

C. I. Disperse Blue 14 (C16H14N2O2; MW=266.30) 106

8 313.15 K 353.15 K 393.15 K

6 y x 106

yx T (K) P (bar) 0.23 313.15 100 0.80 150 1.34 200 1.82 250 0.08 353.15 100 0.46 150 2.11 200 3.22 250 0.35 393.15 100 1.01 150 3.16 200 250 7.72 Synonym: 1,4-Bis(methylamino)anthraquinone Source: Joung, S. N.; Yoo, K.-P. J. Chem. Eng. Data (1998), 43(1), 9-12.

[C-92]

4 2 0 50

150

250

P (bar)

C. I. Disperse Blue 14 (C16H14N2O2; MW=266.29)

[C-93]

6 313 K 333 K 353 K

4

y x 106

T (K) P1) (bar) y1) x 106 100 0.84 313 151 1.15 200 1.26 249 1.68 300 2.94 351 3.52 102 0.46 333 151 0.54 200 1.41 249 2.52 300 3.75 351 4.24 102 0.54 353 151 1.41 200 1.91 251 3.21 300 4.36 351 5.39 1: Obtained by digitizing the graph in the original article. Synonym: 1,4-Bis(methylamino)anthraquinone Source: Gordillo, M. D.; Pereyra, C.; Martinez de la Ossa, E. J. J. Supercrit. Fluids (2003), 27(1), 31-37.

2

0 50

CAT4240—CHAPTER 3—1/11/2006—17:29—SRIDHAR—XML MODEL C – pp. 151–270

150

250 P (bar)

350

208

Solubility in Supercritical Carbon Dioxide

C. I. Disperse Blue 27 (C22H16N2O7; MW=420.37) 106

16 y x 106

yx T (K) P (bar) 323.15 202.6 8.19 303.9 7.95 354.6 12.40 373.15 202.6 0.17 303.9 3.06 354.6 4.51 Synonym: 1,8-Dihydroxy-4-(p -2hydroxyethylanilino)-5nitroanthraquinone Source: Draper, S. L.; Montero, G. A.; Smith, B.; Beck, K. Dyes Pigm. (2000), 45(3), 177-183.

[C-94]

323.15 K 373.15 K

8

0 150

250

350

P (bar)

C. I. Disperse Blue 60 (C20H17N3O5; MW=379.37) P(bar)

y×

1.04 1.33 1.67 1.76 2.09 2.27 2.30 1.38 1.54 1.91 2.39 2.75 2.77 3.39 3.65 1.74 2.18 3.34 3.93 4.57 6.94 7.53 1.75 2.93 3.37 3.69 4.48 4.21 7.65

40

30 y x 106

T(K)

313.15 167.8 195.6 240.3 249.4 272.2 324.1 328.8 333.15 183.6 190.9 213.3 219.7 242.1 243.9 280.4 308.4 363.15 204.1 221.8 252.5 264.3 279.6 318.9 326.6 393.15 194.1 216.0 224.0 232.9 239.0 241.4 280.0

[C-95]

106

313.15 K 333.15 K 363.15 K 393.15 K 423.15 K

20

10

0 100

CAT4240—CHAPTER 3—1/11/2006—17:29—SRIDHAR—XML MODEL C – pp. 151–270

200 P (bar)

300

Solubility Data C

209

282.4 301.2 310.7 326.2 337.6 423.15 150.8 167.0 202.1 230.7 247.3 249.6 251.7 273.9 297.7 319.5 342.0

7.64 10.48 11.48 14.03 16.39 2.46 3.66 5.88 8.14 10.10 10.69 11.08 15.70 21.33 29.04 38.67

Synonyms: C. I. Disperse Blue 99; 1,4-Diamino-N(3-methoxypropyl)anthraquinone-2,3-dicarboximide Source: Sung, H.-D.; Shim, J.-J. J. Chem. Eng. Data (1999), 44(5), 985-989.

[C-96]

C. I. Disperse Blue 60 (C20H17N3O5; MW=379.37)

313.15

333.15

313.15

333.15

P (bar) 253 253 253 253 253 253 253 253 253 253 253 253 253 253 253 253

Cosolvent (mol %) Ethanol 0.00 2.86 5.55 9.57 0.00 2.80 5.19 9.40 Acetone 0.00 2.86 5.29 9.57 0.00 2.92 5.39 9.77

y x 106 1.80 2.07 2.85 4.62 2.86 3.64 5.20 9.43

12 313.15 K (EtOH) 333.15 K (EtOH) 313.15 K (Acetone) 333.15 K (Acetone)

8 y x 106

T (K)

1.80 2.18 2.82 3.29 2.86 3.73 4.76 8.84

4

0 0

Synonyms: C. I. Disperse Blue 99; 1,4-Diamino-N (3-methoxypropyl)anthraquinone-2,3-dicarboximide Source: Kim, C.-H.; Sung, H. D.; Lee, K.-H.; Bae, H.K.; Shim, J.-J.Theories and Applications of Chem. Eng.(1999), 5(2), 2969-2972.

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5 Cosolvent (mol%)

10

210

Solubility in Supercritical Carbon Dioxide

C. I. Disperse Blue 60 (C20H17N3O5; MW=379.37) P (bar)

313.15 209.0 231.0 274.7 312.2 333.15 202.2 238.7 276.5 308.1 324.5 313.15 213.7 237.7 280.0 281.3 314.0 333.15 204.6 224.8 240.5 273.6 310.8

Cosolvent (mol %) Ethanol 4.3 4.3 4.3 4.3 4.3 4.3 4.3 4.3 4.3 Acetone 4.3 4.3 4.3 4.3 4.3 4.3 4.3 4.3 4.3

y x 106 2.34 2.59 2.95 3.55 3.28 4.04 5.32 6.38 7.21

9

6

313.15 K (EtOH) 333.15 K (EtOH) 313.15 K (Acetone) 333.15 K (Acetone)

y x 106

T (K)

[C-97]

3

2.01 2.27 2.58 2.69 3.25 3.60 3.61 4.30 5.08 5.68

0 150

250

350

P (bar)

Synonyms: C. I. Disperse Blue 99; 1,4-Diamino-N(3-methoxypropyl)anthraquinone-2,3-dicarboximide Source: Kim, C.-H.; Sung, H. D.; Lee, K.-H.; Bae, H.K.; Shim, J.-J.Theories and Applications of Chem. Eng.(1999), 5(2), 2969-2972.

C. I. Disperse Blue 60S1) (MW=379)

[C-98]

106

3 y x 106

yx T (K) P (bar) 323.15 202.6 0.41 303.9 0.93 373.15 202.6 0.31 303.9 2.35 1: The molecular formula is not known for this compound. Source: Draper, S. L.; Montero, G. A.; Smith, B.; Beck, K. Dyes Pigm. (2000), 45(3), 177-183.

2

323.15 K 373.15 K

1 0 150

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250 P (bar)

350

Solubility Data C

211

C. I. Disperse Blue 77 (C20H12N2O6; MW=376.32) P (bar)

yx

323.15 202.6 53.8 303.9 129.0 405.2 232.0 373.15 202.6 15.0 303.9 87.3 405.2 227.0 Synonym: 1-Anilino-4,5-dihydroxy-8nitroanthraquinone Source: Draper, S. L.; Montero, G. A.; Smith, B.; Beck, K. Dyes Pigm. (2000), 45(3), 177-183.

[C-99]

300

y x 106

T (K)

106

323.15 K 373.15 K

200 100 0 150

250

350 P (bar)

C. I. Disperse Blue 79 (C24H27BrN6O10; MW=639.42) 0.52 1.73 3.65 7.11 13.60 18.30 23.60 0.54 1.36 3.30 8.88 16.90 29.50 36.30 0.54 1.44 3.50 17.90 28.40 49.90

60 353.2 K 373.2 K 393.2 K

40 yx

yx

[C-100]

106

106

T (K) P (bar) 353.2 180 200 220 240 260 280 300 373.2 180 200 220 240 260 280 300 393.2 180 200 220 260 280 300

450

20

0 150

Synonym: N-[5-[Bis[2-(acetyloxy)ethyl] amino]-2-[(2-bromo4,6-dinitrophenyl)azo]-4-ethoxyphenyl]acetamide Source: Ferri, A.; Banchero, M.; Manna, L.; Sicardi,S. J. Supercrit. Fluids (2004), 30(1), 41-49.

CAT4240—CHAPTER 3—1/11/2006—17:29—SRIDHAR—XML MODEL C – pp. 151–270

200

250 P (bar)

300

212

Solubility in Supercritical Carbon Dioxide

C. I. Disperse Blue 79 (C24H27BrN6O10; MW=639.42) yx

0.34 1.09 2.04 4.38 5.67 0.18 0.49 1.41 4.64 7.52 0.01 0.01 0.70 3.38 9.19

[C-101]

10 323.7 K 353.7 K 383.7 K

y x106

T (K) P (bar) 323.7 101.9 148.1 198.9 253.9 301.3 353.7 99.2 149.2 196.7 253.9 304.7 383.7 99.9 152.7 202.0 255.3 305.1

106

5

0 50

150

250

350

P (bar)

Synonym: N-[5-[Bis[2-(acetyloxy)ethyl] amino]-2-[(2-bromo4,6-dinitrophenyl)azo]-4-ethoxyphenyl]acetamide Source: Lee, J. W.; Park, M. W.; Bae, H. K. Fluid Phase Equil.(2000), 173(2), 277-284.

C. I. Disperse Blue 79 (C24H27BrN6O10; MW=639.42) 0.06 0.67 5.52 22.30 0.06 0.59 4.75 24.40 0.03 0.77 5.52 21.70

[C-102]

30

20

353.2 K 373.2 K 393.2 K

y x 106

T (K) P (bar) 353.2 150 200 250 300 373.2 150 200 250 300 393.2 150 200 250 300

y x 106

Synonym: N-[5-[Bis[2-(acetyloxy)ethyl] amino]-2-[(2-bromo-4,6-dinitrophenyl) azo]-4-ethoxyphenyl]acetamide Source: Lin, H.-m.; Liu, C.-Y.; Cheng, C.-H.; Chen, Y.-T.; Lee, M.-J. J. Supercrit. Fluids (2001), 21(1), 1-9.

10

0 100

CAT4240—CHAPTER 3—1/11/2006—17:29—SRIDHAR—XML MODEL C – pp. 151–270

200 P (bar)

300

Solubility Data C

213

C. I. Disperse Blue 79:1 (C23H25BrN6O10; MW=625.38) 106

30 353.2 K 373.2 K 393.2 K

20 y x 106

T (K) P (bar) y x 353.2 150 0.33 200 3.24 250 11.40 300 25.00 373.2 150 0.15 200 1.71 250 6.97 300 20.70 393.2 150 0.10 200 0.94 250 4.89 300 17.90 Synonym: N-[5-[Bis[2-(acetyloxy)ethyl] amino]-2-[(2-bromo-4,6-dinitrophenyl) azo]-4-methoxyphenyl]acetamide Source: Lin, H.-m.; Ho, C.-C.; Lee, M.-J. J. Supercrit. Fluids(2004), 32(1-3), 105-114.

[C-103]

10

0 100

200

C. I. Disperse Blue 79:1 (C23H25BrN6O10; MW=625.38) y x 106 18.7 22.5 47.5 12.4 104.0 41.9

[C-104]

120 323.15 K 373.15 K

y x 106

T (K) P (bar) 323.15 202.6 303.9 354.6 373.15 202.6 303.9 354.6

300

P (bar)

60

Synonym: N-[5-[Bis[2-(acetyloxy)ethyl] amino]-2-[(2-bromo-4,6-dinitrophenyl) azo]-4-methoxyphenyl]acetamide Source: Draper, S. L.; Montero, G. A.; Smith, B.; Beck, K. Dyes Pigm. (2000), 45(3), 177-183.

0 150

250

350

P (bar)

C. I. Disperse Blue 102 (C15H19SN5O4; MW=365.411) )

[C-105]

106

2 y x 106

yx T (K) P (bar) 323.15 202.6 0.37 303.9 0.52 373.15 202.6 1.90 303.9 1.90 1: This is the MW in SciFinder, while that in the source article is 353. Synonym: 3-[Ethyl[3-methyl-4-[C5-nitro2-thiazolyl)azo]phenyl]amino]-1,2-propanediol Source: Draper, S. L.; Montero, G. A.; Smith, B.; Beck, K. Dyes Pigm. (2000), 45(3), 177-183.

1

323.15 K 373.15 K

0 150

CAT4240—CHAPTER 3—1/11/2006—17:29—SRIDHAR—XML MODEL C – pp. 151–270

250 P (bar)

350

214

Solubility in Supercritical Carbon Dioxide

C. I. Disperse Blue 118 (C20H14N2O4; MW=346.34) 106

9 y x 106

yx T (K) P (bar) 323.15 202.6 0.84 303.9 2.45 405.2 3.41 373.15 202.6 0.36 303.9 3.55 405.2 7.57 Synonym: 1-Amino-4,5-dihydroxy-8(phenylamino)anthraquinone Source: Draper, S. L.; Montero, G. A.; Smith, B.; Beck, K. Dyes Pigm. (2000), 45(3), 177-183.

[C-106]

323.15 K 373.15 K

6 3 0 150

250

350

450

P (bar)

C. I. Disperse Blue 134 (C20H22N2O2; MW=322.40)

[C-107]

106

323.15 K 353.15 K 383.15 K

150

y x 106

yx T (K) P (bar) 323.15 100 1.2 120 11.1 150 29.6 200 56.5 250 87.4 353.15 100 0.3 120 1.4 150 9.8 200 67.7 250 130.8 383.15 100 0.6 120 1.7 150 7.4 200 45.7 250 153.6 Synonym: 1,4-Bis(isopropylamino)anthraquinone Source: Tamura, K.; Shinoda, T. Fluid Phase Equil.(2004), 219(1), 25-32.

100

50

0 50

150

250

P (bar)

C. I. Disperse Blue 134 (1) + C. I. Disperse Yellow 16 (2) Mixture T (K)

P (bar)

y1 x 106

y2 x 106

300

383.15

Blue 134 Yellow 16

y x 106

100 0.57 1.83 120 1.76 4.83 150 6.62 14.95 200 50.91 86.52 250 164.60 264.9 Source: Tamura, K.; Shinoda, T. Fluid Phase Equil.(2004), 219(1), 25-32.

[C-108]

150

0 50

100

150

200

P (bar)

CAT4240—CHAPTER 3—1/11/2006—17:29—SRIDHAR—XML MODEL C – pp. 151–270

250

Solubility Data C

215

C. I. Disperse Blue 165:1 (C19H19N7O5; MW=425.40)

y x 106

yx T (K) P (bar) 323.15 202.6 0.25 303.9 0.65 373.15 202.6 0.14 303.9 1.19 Synonym: N-[2-[(2-Cyano-4,6-dinitrophenyl) azo]-5-(diethylamino)phenyl]acetamide Source: Draper, S. L.; Montero, G. A.; Smith, B.; Beck, K. Dyes Pigm. (2000) 45(3), 177-183.

[C-109]

1.4

106

323.15 K 373.15 K

0.7

0.0 150

250 P (bar)

C. I. Disperse Blue 291 (C19H21BrN6O6; MW=509.31) P (bar)

313.15 128.1 154.9 180.1 221.6 261.3 289.5 326.4 333.15 151.2 167.7 176.3 213.6 255.8 269.9 318.2 363.15 149.2 152.6 167.7 195.8 206.8 243.6 271.3 293.2 313.7 393.15 126.4 147.2 164.9 214.2 222.8

[C-110]

y x 106 1.24 2.03 2.75 3.52 4.44 5.14 5.62 1.71 2.23 2.99 4.22 6.59 7.66 10.49 1.25 1.62 2.25 3.83 4.97 8.69 10.59 14.79 19.67 1.92 2.72 4.19 8.11 10.35

60

40

313.15 K 333.15 K 363.15 K 393.15 K

y x 106

T (K)

350

20

0 100

CAT4240—CHAPTER 3—1/11/2006—17:29—SRIDHAR—XML MODEL C – pp. 151–270

200 P (bar)

300

216

Solubility in Supercritical Carbon Dioxide

256.2 290.7 326.9 342.1

18.23 28.49 45.66 52.51 Synonym: N-[2-[(2-Bromo-4,6-dinitrophenyl)azo]-5(diethylamino)-4-methoxyphenyl]acetamide Source: Shim, J.-J.; Baek, J.-K.; Sung, H.-D.; Lee, K.-H.; Choi, J.-H. Proceedings of the 6th Conference on Supercritical Fluids and Their Applications, Maiori, Italy, (Sep. 12, 2001), 565-570. (Data from Baek's thesis).

C. I. Disperse Blue 354 (C31H37SN3O2; MW=515.71) 0.02 0.63 3.16 10.03 17.77 27.84 0.01 0.32 5.28 20.36 44.48 0.01 0.08 1.80 12.61 40.95

323.15 K 353.15 K 383.15 K

40 y x 106

T (K) P (bar) 323.15 100 120 150 200 250 300 353.15 120 150 200 250 300 383.15 120 150 200 250 300

[C-111]

y x 106

20

0 50

Synonym: [2-[[4-(Dihexylamino)-2-methylphenyl] methylene]-1,1-dioxidobenzo[b]thien-3(2H )-ylidene] propanedinitrile Source: Shinoda, T.; Tamura, K. J. Chem. Eng. Data (2003), 48(4), 869-873.

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150

250 P (bar)

350

Solubility Data C

217

C. I. Disperse Brown 221) (MW=399)

[C-112]

106

60

y x 106

yx T (K) P (bar) 323.15 202.6 15.9 303.9 11.7 354.6 15.4 373.15 202.6 18.8 303.9 57.0 354.6 36.6 1: The molecular formula is not known for this material. Source: Draper, S. L.; Montero, G. A.; Smith, B.; Beck, K. Dyes Pigm. (2000), 45(3), 177-183.

40

323.15 K 373.15 K

20 0 100

200

300 P (bar)

C. I. Disperse Dyes Dye Index Number

Name of the compounds

400

T (K)

[C-113] 6 P (bar) y x 10

C. I. Disperse Blue 79:11)

2-(Acetylamino)-4-(N,N-bis(acetoxyethyl) 353.15 amino)-5-ethoxy-2',4',6'-trinitroazobenzene

200

1.13

C. I. Disperse Orange 1

4-(N-Phenylamino)-4'-nitroazobenzene

353.15

200

2.91

4-Amino-4'-nitroazobenzene 4-[N-(2-Cyanoethyl)-N-ethylamino]-4'nitroazobenzene

353.15

200

3.99

353.15

200

1.31

353.15

200

5.70

353.15

200

3.76

C. I. Disperse Orange 3 C. I. Disperse Orange 25 C. I. Disperse Orange 30 C. I. Disperse Red 60

4-[(2,6-Dichloro-4-nitrophenyl)azo]-N(cyanoethyl)-N-(acetoxyethyl)aniline 1-Amino-4-hydroxy-2phenoxyanthraquinone

1: Though, in the source, the compound was named "C.I. Disperse Blue 79:1,"it must be a different material because, in the SciFinder, C. I. Disperse Blue 79:1 is shown to be 4-(6-Bromo-2,4-dinitrophenylazo)-3-acetylamino-6-methoxy-N-bis(acetoxyethyl)aniline. Source: Oezcan, A. S.; Clifford, A. A.; Bartle, K. D.; Lewis, D. M. J. Chem. Eng. Data (1997), 42(3), 590-592.

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218

Solubility in Supercritical Carbon Dioxide

C. I. Disperse Orange 3 (C12H10N4O2; MW=242.24)

[C-114]

106

353.2 K 373.2 K 393.2 K

y x 106

yx T (K) P (bar) 20 353.2 160 1.59 180 3.24 200 5.11 15 220 8.31 240 9.86 260 13.40 280 15.50 10 373.2 160 1.45 180 3.09 200 6.00 5 220 9.56 240 14.00 393.2 160 1.63 0 180 3.27 150 200 4.95 220 10.90 240 17.40 Synonyms: 4-(4-Nitrophenylazo)aniline; 4-Amino-4'nitroazobenzene Source: Ferri, A.; Banchero, M.; Manna, L.; Sicardi, S. J. Supercrit. Fluids (2004), 30(1), 41-49.

200

250 P (bar)

C. I. Disperse Orange 3 (C12H10N4O2; MW=242.24) T (K) P (bar) 323.7 101.3 149.8 205.8 247.5 305.0 353.7 103.3 154.2 203.9 247.8 304.7 383.7 103.4 150.4 198.5 250.6 301.6 413.7 103.7 148.1 203.0 251.3 310.6

yx

300

[C-115]

106 323.7 K 353.7 K 383.7 K 413.7 K

y x 106

1.52 6.98 90 13.66 20.76 16.34 0.09 2.56 60 9.92 18.22 27.52 0.13 30 4.24 10.69 19.11 32.24 0.45 0 4.40 50 10.86 20.78 92.44 Synonyms: 4-(4-Nitrophenylazo)aniline; 4-Amino-4'nitroazobenzene Source: Lee, J. W.; Min, J. M.; Bae, H. K. J. Chem . Eng. Data (1999), 44(4), 684-687.

CAT4240—CHAPTER 3—1/11/2006—17:29—SRIDHAR—XML MODEL C – pp. 151–270

150

250 P (bar)

350

Solubility Data C

219

C. I. Disperse Orange 11(C15H11NO2; MW=237.26) 106

6 y x 106

T (K) P (bar) y × 333.15 132 1.71 152 2.39 172 3.21 193 4.16 353.15 132 0.93 152 1.73 172 3.00 193 4.88 Synonym: 1-Amino-2-methylanthraquinone Source: Guzel, B.; Akgerman, A. J. Chem. Eng. Data (1999), 44(1), 83-85.

[C-116]

333.15 K 353.15 K

3

0 120

160 P (bar)

C. I. Disperse Orange 11 (C15H11NO2; MW=237.26) 106

[C-117]

40 313.15 K 353.15 K 393.15 K

30 y x 106

yx T (K) P (bar) 1.08 313.15 100 3.19 150 7.02 200 8.20 250 0.36 353.15 100 2.46 150 8.71 200 18.14 250 1.17 393.15 100 4.81 150 13.44 200 250 36.03 Synonym: 1-Amino-2-methylanthraquinone Source: Joung, S. N.; Yoo, K.-P. J. Chem. Eng. Data (1998), 43(1), 9-12.

200

20 10 0 50

CAT4240—CHAPTER 3—1/11/2006—17:29—SRIDHAR—XML MODEL C – pp. 151–270

150 P (bar)

250

220

Solubility in Supercritical Carbon Dioxide

C. I. Disperse Orange 13 (C22H16ON4; MW=352.39) T (K)

P (bar)

305

77 80 87 110 140 200 300 400 500 110 120 120 130 140 140 150 160 160 170 170 185 185 200 200 150 160 170 180 190 200 210

M x 106 (mol/L) 1.3 1.8 2.7 5.5 8.1 13.7 21.7 29.5 35.3 1.8 3.0 3.4 5.6 8.7 9.0 13.0 15.1 14.9 20.3 20.2 25.1 25.3 33.0 33.6 1.6 2.9 4.8 7.8 11.2 17.6 24.9

220

32.5

2.61

75

2.2

0.87

120

2.4

0.55

150

3.4

0.59

180

5.7

0.80

200

10.5

1.30

220

20.9

2.32

240

34.9

3.53

240

34.7

3.51

370

410

y1) x 106 0.09 0.12 0.17 0.31 0.43 0.68 1.01 1.32 1.53 0.20 0.27 0.31 0.45 0.64 0.66 0.90 0.99 0.98 1.29 1.28 1.53 1.54 1.95 1.98 0.20 0.34 0.51 0.78 1.04 1.55 2.09

4 305 K 330 K 370 K 410 K

3 y x 106

330

[C-118]

2

1

0 0

1: Calculated from M. Synonym: 4-[4-(Phenylazo)-1-naphthylazo]phenol Sources: Haarhaus, U.; Swidersky, P.; Schneider, G. M. J. Supercrit. Fluids (1995), 8, 100-106. Another source (: Haarhaus, U., Sc.D. Thesis, University of Bochum, Bochum, Germany, 1992.)

CAT4240—CHAPTER 3—1/11/2006—17:29—SRIDHAR—XML MODEL C – pp. 151–270

200 P (bar)

400

Solubility Data C

221

C. I. Disperse Orange 25 (C17H17N5O2; MW=323.35) yx

0.013 0.191 0.660 1.556 2.705 3.991 0.002 0.014 0.187 1.662 4.360 8.062 0.009 0.029 0.176 1.661 6.413 17.090

[C-119]

18 323.15 K 353.15 K 383.15 K

12 y x 106

T (K) P (bar) 323.15 100 120 150 200 250 300 353.15 100 120 150 200 250 300 383.15 100 120 150 200 250 300

106

6

0 50

150

250

350

P (bar)

Synonym: 4-[N-(2-Cyanoethyl)-N-ethylamino]-4'nitroazobenzene Source: Shinoda, T.; Tamura, K. J. Chem. Eng. Data (2003), 48(4), 869-873.

C. I. Disperse Orange 30 (C19H17Cl2N5O4; MW=450.27) yx

8.01 9.57 12.24 14.59 17.58 21.56 23.44 25.90 26.05 9.51 11.40 11.68 15.38 16.45 19.02 26.12 30.01 34.06 35.11 39.11 42.25

90

60

313.15 K 333.15 K 363.15 K 393.15 K

y x 106

T (K) P (bar) 313.15 114.6 132.8 172.7 206.1 227.3 270.5 294.0 308.0 310.9 333.15 135.7 152.7 158.0 178.5 184.4 201.2 237.0 250.9 274.5 277.2 295.1 312.0

[C-120]

106

30

0 100

.

CAT4240—CHAPTER 3—1/11/2006—17:29—SRIDHAR—XML MODEL C – pp. 151–270

200 P (bar)

300

222

Solubility in Supercritical Carbon Dioxide

363.15 130.3 145.8 159.5 160.3 180.3 190.6 212.3 226.1 266.4 285.6 290.5 310.8 321.0 393.15 112.8 136.8 161.5 166.9

9.09 11.20 13.34 14.02 17.54 20.34 23.81 28.89 38.98 45.20 49.78 53.63 58.03 9.56 13.85 17.45 19.32

171.3

20.50

212.8

30.01

242.5

39.56

262.0

50.48

281.3 302.5 325.7

62.74 72.56 84.32

Synonym: 4-[(2,6-Dichloro-4-nitrophenyl)azo]-N(cyanoethyl)-N-(acetoxyethyl)aniline Source: Baek, J.-K.; Kim, S.; Lee, G.-S.; Shim, J.-J. Korean J. Chem. Eng. (2004), 21(1), 230-235.

C. I. Disperse Orange 30 (C19H17Cl2N5O4; MW=450.28) 106

80 323.15 K 373.15 K

y x 106

yx T (K) P (bar) 323.15 202.6 6.38 303.9 30.40 354.6 72.50 373.15 202.6 1.75 303.9 17.90 354.6 37.00 Synonym: 4-[(2,6-Dichloro-4nitrophenyl)azo]-N-(cyanoethyl)-N(acetoxyethyl)aniline Source: Draper, S. L.; Montero, G. A.; Smith, B.; Beck, K. Dyes Pigm. (2000), 45(3), 177-183.

[C-121]

40

0 150

CAT4240—CHAPTER 3—1/11/2006—17:29—SRIDHAR—XML MODEL C – pp. 151–270

250 P (bar)

350

Solubility Data C

223

C. I. Disperse Orange 331) P2)

T (K) 323.15

(bar)

y2)

x

[C-122]

106

323.15 K 353.15 K 373.15 K 398.15 K 408.15 K 418.15 K

y x 106

98 0.00 124 1.86 149 5.58 174 8.97 203 13.37 232 17.43 255 18.62 30 353.15 108 0.00 123 0.00 148 0.85 173 4.06 197 9.14 226 22.85 20 251 28.60 373.15 100 0.00 149 0.00 174 0.00 199 5.42 10 224 11.68 249 22.68 98 398.15 0.00 122 0.00 149 0.17 0 170 1.86 50 196 3.89 224 9.48 250 17.09 408.15 147 0.17 171 1.86 195 4.74 219 10.49 251 17.09 418.15 149 0.34 170 1.86 201 5.25 222 9.31 20.14 250 1: The molecular structure of this compound is not known. 2: Obtained by digitizing the graph in the original article. Source: Tabata, I.; Lyu, J.; Cho, S.; Tominaga, T.; Hori, T. Coloration Tech. (2001), 117(6), 346-351.

CAT4240—CHAPTER 3—1/11/2006—17:29—SRIDHAR—XML MODEL C – pp. 151–270

150 P (bar)

250

224

Solubility in Supercritical Carbon Dioxide

C. I. Disperse Red 1 (C16H18N4O3; MW=314.35)

[C-123]

106

yx T (K) P (bar) 0.08 313.15 100 0.34 150 0.64 200 0.83 250 0.05 353.15 100 0.21 150 1.43 200 3.18 250 0.24 393.15 100 1.02 150 5.18 200 250 16.19 Synonym: N-Ethyl-N-(2-hydroxyethyl)4-[(p-nitrophenyl)azo]aniline Source: Joung, S. N.; Yoo, K.-P. J. Chem. Eng. Data (1998), 43(1), 9-12.

20 313.15 K 353.15 K 393.15 K

y x 106

15 10 5 0 50

150 P (bar)

C. I. Disperse Red 1 (C16H18N4O3; MW=314.35)

250

[C-124]

106

y x 106

yx T (K) P (bar) 0.02 323.15 100 0.16 120 0.64 150 1.58 200 2.85 250 4.81 300 0.01 353.15 100 0.05 120 0.39 150 2.61 200 7.26 250 11.10 300 0.02 383.15 100 0.11 120 0.49 150 3.84 200 12.30 250 300 30.86 Synonym: N-Ethyl-N-(2-hydroxyethyl)-4-[(pnitrophenyl)azo]aniline Source: Shinoda, T.; Tamura, K.Fluid Phase Equil. (2003), 213(1-2), 115-123.

323.15 K 353.15 K

30

383.15 K

20

10

0 50

CAT4240—CHAPTER 3—1/11/2006—17:29—SRIDHAR—XML MODEL C – pp. 151–270

150

250 P (bar)

350

Solubility Data C

225

C. I. Disperse Red 1 (C16H18N4O3; MW=314.35) T (K) 313

P1)

(bar)

y1)

x

[C-125]

106

y x 106

82 0.05 83 0.07 84 0.09 85 0.12 15 86 0.19 87 0.25 88 0.35 89 0.44 10 91 0.72 92 0.95 93 1.20 5 96 1.40 99 1.90 102 2.30 107 2.90 0 115 3.80 50 121 4.70 128 5.50 130 5.90 141 7.10 158 9.10 172 10.00 205 12.00 267 12.00 1: Obtained by digitizing the graph in the original article. Synonym: N-Ethyl-N-(2-hydroxyethyl)-4-[(pnitrophenyl)azo]aniline Source: West, B. L.; Kazarian, S. G.; Vincent, M. F.; Brantley, N. H.; Eckert, C. A. J. App. Polym. Sci. (1998), 69(5), 911-919.

150 P (bar)

C. I. Disperse Red 9 (C15H11NO2; MW=237.25) yx T (K) P (bar) 1.66 313.15 100 5.96 150 10.09 200 15.58 250 0.38 353.15 100 1.39 150 19.61 200 35.00 250 2.80 393.15 100 5.65 150 35.46 200 250 95.16 Synonym: 1-(Methylamino)anthraquinone Source: Joung, S. N.; Yoo, K.-P. J. Chem. Eng. Data (1998), 43(1), 9-12.

[C-126]

100 313.15 K 353.15 K 393.15 K

75 y x 106

106

250

50 25 0 0

CAT4240—CHAPTER 3—1/11/2006—17:29—SRIDHAR—XML MODEL C – pp. 151–270

100

200 P (bar)

300

226

Solubility in Supercritical Carbon Dioxide

C. I. Disperse Red 11 (C15H12N2O3; MW=268.27)

300

310

320

330

P (bar) 100 200 250 350 450 550 650 750 850 950 1100 1200 1400 100 200 350 400 500 600 800 1000 1200 250 300 350 400 450 500 600 700 800 160 170 180 190 250 300 400 450 500 550 600

M x 106 (mol/L) 3.4 7.2 9.7 13.1 16.1 21.1 22.7 24.9 27.5 31.3 33.1 35.2 39.4 2.7 8.6 16.2 18.8 24.0 28.4 38.2 47.0 54.8 13.3 16.5 21.0 25.1 29.3 33.7 42.1 47.9 55.2 4.7 5.7 7.0 7.7 14.3 20.7 27.9 34.5 42.5 48.6 59.3

y1) x 106 0.19 0.35 0.46 0.59 0.70 0.89 0.94 1.01 1.09 1.23 1.27 1.34 1.47 0.17 0.44 0.75 0.86 1.05 1.21 1.57 1.86 2.12 0.69 0.82 1.01 1.18 1.35 1.52 1.85 2.05 2.31 0.31 0.36 0.43 0.46 0.78 1.08 1.36 1.64 1.98 2.22 2.67

300 K 310 K 320 K 330 K 340 K

3

y x 106

T (K)

[C-127]

2

1

0 0

CAT4240—CHAPTER 3—1/11/2006—17:29—SRIDHAR—XML MODEL C – pp. 151–270

500

1000 P (bar)

1500

Solubility Data C

340

227

71.8 8.2 13.8 16.4 26.3 35.9 45.5 56.2 64.6

700 200 235 250 300 350 400 450 500

3.14 0.53 0.82 0.96 1.44 1.88 2.30 2.77 3.11

1: Calculated from M. Synonym: 1,4-Diamino-2-methoxyanthraquinone Sources: Swidersky, P.; Tuma, D.; Schneider, G. M. J. Supercrit. Fluids (1996), 9, 12-18. (Another source: Haarhaus, U., Sc.D. Thesis, University of Bochum, Bochum, Germany, 1992.)

C. I. Disperse Red 13 (C16H17ClN4O3; MW=348.79) yx

0.04 0.58 2.06 5.26 7.94 11.94 0.01 0.07 0.75 7.02 14.01 25.50 0.05 0.13 0.72 5.42 22.43 47.31

323.15 K 353.15 K 383.15 K

40 y x 106

T (K) P (bar) 323.15 100 120 150 200 250 300 353.15 100 120 150 200 250 300 383.15 100 120 150 200 250 300

[C-128]

106

20

0 50

Synonym: 4-Nitro-2-chloro-4'-[ethyl(2-hydroxyethyl) amino]azobenzene Source: Shinoda, T.; Tamura, K. Fluid Phase Equil. (2003), 213(1-2), 115-123.

CAT4240—CHAPTER 3—1/11/2006—17:29—SRIDHAR—XML MODEL C – pp. 151–270

150

250 P (bar)

350

228

Solubility in Supercritical Carbon Dioxide

C. I. Disperse Red 30 (C16H17ClN4O4; MW=364.78) 106

50 y x 106

yx T (K) P (bar) 323.15 202.6 43.40 303.9 7.88 354.6 4.25 373.15 202.6 16.40 303.9 20.40 354.6 30.30 Synonym: 2,2'-[[4-[(2-Chloro-4nitrophenyl)azo]phenyl]imino]bisethanol Source: Draper, S. L.; Montero, G. A.; Smith, B.; Beck, K. Dyes Pigm. (2000), 45(3), 177-183.

[C-129] 323.15 K 373.15 K

25

0 150

250

350

P (bar)

C. I. Disperse Red 60 (C20H13NO4; MW=331.33)

303.1

P (bar) 72 96 106 116 126 136 146 156 166 176 196 221 248 291 336 394 448 506 566 616 676 746 816 896 976

M x 106 (mol/L) 7.44 31.76 39.50 47.18 54.66 62.39 70.48 78.20 85.24 93.32 108.35 127.01 146.41 174.89 205.02 240.72 271.55 301.33 329.86 352.44 378.66 401.34 416.42 438.05 448.29

y1) x 106 0.45 1.83 2.21 2.58 2.94 3.30 3.67 4.03 4.34 4.70 5.36 6.17 6.98 8.14 9.35 10.73 11.88 12.97 13.97 14.76 15.65 16.36 16.77 17.42 17.62

30 303.1 K 314.8 K 322.5 K 332.7 K

20 y x 106

T (K)

[C-130]

10

0 0

250

CAT4240—CHAPTER 3—1/11/2006—17:29—SRIDHAR—XML MODEL C – pp. 151–270

500 P (bar)

750

1000

Solubility Data C

314.8

322.5

332.7

229

90 120 126 142 158 168 182 191 206 228 251 286 316 346 376 410 446 482 522 566 606 660 726 800 156 171 181 196 208 222 242 274 300

0.80 28.25 37.51 54.33 65.98 82.67 88.55 106.68 114.91 135.99 157.94 191.49 213.71 243.36 265.35 290.51 317.82 341.97 375.32 398.63 421.23 442.49 468.55 494.39 60.21 78.11 93.01 113.79 131.79 151.52 182.29 228.92 271.60

0.08 1.77 2.29 3.16 3.71 4.57 4.79 5.70 6.03 6.98 7.95 9.40 10.29 11.53 12.40 13.37 14.43 15.33 16.61 17.41 18.20 18.87 19.69 20.46 3.67 4.59 5.35 6.38 7.26 8.19 9.64 11.75 13.67

320

298.40

14.81

339

328.04

16.09

360

357.81

17.34

398

409.80

19.48

440

460.55

21.48

488

514.57

23.55

550

554.45

24.85

286

280.90

15.03

296

295.18

15.65

330

328.90

16.95

368

360.46

18.10

CAT4240—CHAPTER 3—1/11/2006—17:29—SRIDHAR—XML MODEL C – pp. 151–270

230

Solubility in Supercritical Carbon Dioxide

402 456 500 566 646 746

390.52 425.14 451.56 488.40 517.22 549.06

19.22 20.36 21.22 22.40 23.13 23.92

1: Calculated from M. Synonym: 1-Amino-4-hydroxy-2-phenoxyanthraquinone Sources: Kraska, T.; Leonhard, K. O.; Tuma, D.; Schneider, G. M.Fluid Phase Equil. (2002), 194-197, 469482. (The numerical data are from Tuma, D. Sc.D. Thesis, University of Bochum, Bochum, Germany, 1999.)

C. I. Disperse Red 60 (C20H13NO4; MW=331.33)

y x 106

y x 106 2.11 7.56 12.66 16.68 21.25 0.78 5.17 9.81 20.21 29.53 0.23 2.19 9.78 19.17 29.94 0.14 1.72 7.07 18.68 37.51 Synonym: 1-Amino-4-hydroxy-2phenoxyanthraquinone Source: Lee, J. W.; Min, J. M.; Bae, H. K. J. Chem . Eng. Data (1999), 44(4), 684-687. T (K) P (bar) 323.7 102.9 155.3 200.3 251.3 305.7 353.7 101.5 153.6 204.7 252.3 305.6 383.7 101.5 153.8 205.8 254.7 300.3 413.7 101.5 156.5 208.6 252.3 301.8

[C-131]

40 323.7 K 353.7 K 383.7 K 413.7 K

30

20

10

0 50

CAT4240—CHAPTER 3—1/11/2006—17:29—SRIDHAR—XML MODEL C – pp. 151–270

150

250 P (bar)

350

Solubility Data C

231

C. I. Disperse Red 60 (C20H13NO4; MW=331.33)

423.15

y×

1.61 1.92 2.55 3.28 5.46 7.41 9.59 12.39 14.13 0.82 1.66 4.14 6.47 9.80 13.91 17.79 20.52 0.72 2.64 5.92 4.96 8.93 7.20 14.35 15.04 27.79 36.09 41.38 2.33 6.95 13.58 22.75 32.30 38.02 42.08 68.98 68.03

335.4

72.47

114.4

2.03

136.9

4.40

167.0

7.15

200.9

15.40

258.9

49.78

291.7

85.03

150 313.15 K 333.15 K 363.15 K 393.15 K 423.15 K

100 y x 106

T (K) P (bar) 313.15 98.5 104.1 113.4 119.9 159.5 188.1 242.3 275.1 328.3 333.15 122.0 126.2 158.3 180.5 210.5 248.8 283.1 307.1 363.15 121.0 149.2 181.1 183.6 200.6 201.8 230.8 242.9 279.9 309.6 322.8 393.15 145.5 181.8 214.8 246.6 264.5 272.9 285.5 323.0 328.4

[C-132]

106

50

0 50

322.3 129.90 Synonym: 1-Amino-4-hydroxy-2-phenoxyanthraquinone Source: Sung, H.-D.; Shim, J.-J. J. Chem. Eng. Data (1999), 44(5), 985-989.

CAT4240—CHAPTER 3—1/11/2006—17:29—SRIDHAR—XML MODEL C – pp. 151–270

150

P (bar)

250

350

232

Solubility in Supercritical Carbon Dioxide

C. I. Disperse Red 60 (C20H13NO4; MW=331.33) T (K) 323.15

P1)

(bar)

y1)

x

106

[C-133]

9

75.9 0.00 97.4 0.94 149.0 2.87 6 203.2 4.03 255.1 5.75 353.15 96.1 0.50 147.6 2.71 3 197.1 4.97 244.3 6.80 398.15 71.4 0.28 0 98.0 0.94 144.6 2.71 50 196.4 4.86 8.45 244.5 1: Obtained by digitizing the graph in the original article. Synonym: 1-Amino-4-hydroxy-2-phenoxyanthraquinone

y x 106

323.15 K 353.15 K 398.15 K

150

250

P (bar)

Source: Tabata, I.; Lyu, J.; Cho, S.; Tominaga, T.; Hori, T. Coloration Tech. (2001), 117(6), 346-351.

C. I. Disperse Red 60 (C20H13NO4; MW=331.33) Mx y1) x 106 (mol/L) 310.4 83 0.68 0.07 85 2.40 0.21 9 91 10.70 0.76 95 14.21 0.96 100 19.69 1.27 6 110 30.82 1.88 120 41.55 2.44 130 49.83 2.85 3 135 57.44 3.25 140 59.95 3.35 145 68.01 3.77 0 150 73.10 4.01 50 155 78.68 4.28 160 85.01 4.59 170 95.96 5.11 180 106.68 5.61 190 117.79 6.12 200 130.37 6.70 210 143.92 7.33 1: Calculated from M. Synonym: 1-Amino-4-hydroxy-2-phenoxyanthraquinone Sources: Tuma, D.; Wagner, B.; Schneider, G. M. Fluid Phase Equil. (2001), 182, 133-143. P (bar)

y x 106

T (K)

[C-134]

106

100

CAT4240—CHAPTER 3—1/11/2006—17:30—SRIDHAR—XML MODEL C – pp. 151–270

150 P (bar)

200

250

Solubility Data C

233

C. I. Disperse Red 60 (C20H13NO4; MW=331.33) T (K)

P (bar)

Cosolvent1) (mol%)

[C-135]

60

y x 106

Acetone 333.15 K Ethanol 313.15 K Ethanol 333.15 K

40

y x 106

Acetone 333.15 141.5 4.3 13.46 186.8 4.3 25.11 250.1 4.3 35.47 326.0 4.3 50.85 253.2 0.0 16.00 253.2 4.3 35.47 253.2 4.8 39.74 253.2 9.2 80.33 Ethanol 313.15 148.4 4.3 11.05 174.7 4.3 14.93 231.1 4.3 19.82 306.0 4.3 27.78 253.2 0.0 11.44 253.2 2.4 16.58 253.2 4.6 22.84 253.2 8.9 36.66 333.15 135.4 4.3 9.08 203.5 4.3 22.71 225.4 4.3 28.86 291.3 4.3 38.83 337.4 4.3 50.44 253.2 0.0 16.00 253.2 2.2 22.88 253.2 4.4 31.30 253.2 8.4 69.49 1: Cosolvent in CO2 on a solvent-free basis. Synonym: 1-Amino-4-hydroxy-2phenoxyanthraquinone Source: Muthukumaran, P.; Gupta, R. B.; Sung, HD.; Shim, J.-J.; Bae, H.-K.Korean J. Chem. Eng. (1999), 16(1), 111-117.

4.3 mol%

20

0 100

200

300

P (bar 90 Acetone 333.15 K Ethanol 313.15 K Ethanol 333.15 K

60

y x 106

253.2 bar

30

0 0

CAT4240—CHAPTER 3—1/11/2006—17:30—SRIDHAR—XML MODEL C – pp. 151–270

5 Cosolvent (mol%)

10

234

Solubility in Supercritical Carbon Dioxide

[C-136]

C. I. Disperse Red 82 (C21H21N5O6; MW=439.43) y x

0.64 10.80 34.40 42.20 0.19 4.03 16.60 29.60 0.17 1.60 11.40 23.80

50

y x 106

T (K) P (bar) 353.2 150 200 250 300 373.2 150 200 250 300 393.2 150 200 250 300

106

353.2 K 373.2 K 393.2 K

25

0 100

200

300

P (bar)

Synonym: 3-Nitro-6-[4-[N,N-di(acetoxyethyl)amino] phenyl]azobenzonitrile Source: Lin, H.-m.; Ho, C.-C.; Lee, M.-J. J. Supercrit. Fluids(2004), 32(1-3), 105-114.

C. I. Disperse Red 1371) (MW=430)

[C-137]

106

20 y x 106

yx T (K) P (bar) 323.15 202.6 11.00 303.9 2.69 354.6 2.08 373.15 202.6 2.75 303.9 10.70 354.6 7.42 1: The molecular formula is not known for this material. Source: Draper, S. L.; Montero, G. A.; Smith, B.; Beck, K. Dyes Pigm. (2000), 45(3), 177-183.

323.15 K 373.15 K

10

0 150

CAT4240—CHAPTER 3—1/11/2006—17:30—SRIDHAR—XML MODEL C – pp. 151–270

250 P (bar)

350

Solubility Data C

235

C. I. Disperse Red 152 (C19H17Cl2N5S; MW=418.34) T (K)

P (bar)

1.84 2.17 2.49 3.15 3.78 3.91 4.16 4.59 1.78 2.28 3.11 3.45 4.85 5.29 5.40 5.79 2.19 2.31 2.65 3.45 4.55 4.98 5.99 6.98 7.70 9.85 4.05 4.29 4.55 5.64 6.97 7.18 9.20 10.09 13.86 18.60 20.33 Synonym: 3-[[4-[[5,6(or 6,7)-Dichloro-2benzothiazolyl] azo]-3-methylphenyl] ethylamino]propanenitrile Source: Shim, J.-J.; Baek, J.-K.; Sung, H.-D.; Lee, K.-H.; Choi, J.-H. Proceedings of the 6th Conference on Supercritical Fluids and Their Applications, Maiori, Italy, (Sep. 12, 2001), 565-570. (Data from Baek's thesis)

y x 106

333.15 142.4 155.0 167.5 191.6 231.0 270.5 290.6 316.8 363.15 147.9 166.5 190.4 205.5 235.7 259.0 270.7 304.5 393.15 132.3 138.0 151.0 176.3 187.5 204.5 223.3 255.6 268.9 318.1 423.15 125.1 128.5 143.0 150.6 174.0 176.8 206.5 223.4 255.3 306.8 329.2

yx

[C-138]

106

20

333.15 K 363.15 K 393.15 K 423.15 K

10

0 100

CAT4240—CHAPTER 3—1/11/2006—17:30—SRIDHAR—XML MODEL C – pp. 151–270

200 P (bar)

300

236

Solubility in Supercritical Carbon Dioxide

C. I. Disperse Red 153 (C18H15Cl2N5S; MW=404.32)

[C-139]

106

yx T (K) P (bar) 5.0 353.2 150 0.03 200 0.30 250 1.31 300 2.58 2.5 393.2 150 0.04 200 0.27 250 1.21 0.0 300 3.81 Synonym: 3-[[4-[[5,6(or 6,7)-Dichloro-2100 benzothiazolyl]azo]phenyl]ethylamino] propanenitrile Source: Lin, H.-m.; Liu, C.-Y.; Cheng, C-H.; Chen, Y.-T.; Lee, M.-J. J. Supercrit. Fluids (2001), 21(1), 1-9.

y x 106

353.2 K 393.2 K

200 P (bar)

C. I. Disperse Red 167 (C23H26ClN5O7; MW=519.931)) P (bar)

323.15 202.6 303.9 405.2 373.15 202.6 303.9 405.2

yx

4.63 13.30 22.20 0.97 11.40 34.00

[C-140]

40 y x 106

T (K)

106

323.15 K 373.15 K

20

1: This is the MW in SciFinder, while that in the source article is 506. Synonym: N-[5-[Bis[2-(acetyloxy)ethyl] amino]-2-[(2-chloro-4-nitrophenyl)azo] phenyl]propanamide Source: Draper, S. L.; Montero, G. A.; Smith, B.; Beck, K. Dyes Pigm. (2000), 45(3), 177-183.

0 150

250

350

450

P (bar)

C. I. Disperse Red 324 (MW=4261))

[C-141]

106

6 y x 106

yx T (K) P (bar) 323.15 202.6 1.41 303.9 2.60 373.15 202.6 0.47 303.9 4.42 1: The molecular formula is not known for this material. Source: Draper, S. L.; Montero, G. A.; Smith, B.; Beck, K. Dyes Pigm. (2000), 45(3), 177-183.

300

323.15 K 373.15 K

3

0 150

CAT4240—CHAPTER 3—1/11/2006—17:30—SRIDHAR—XML MODEL C – pp. 151–270

250 P (bar)

350

Solubility Data C

237

C. I. Disperse Red 3241) (MW=426)

[C-142]

9 353.2 K 373.2 K 393.2 K

6

y x 106

y x 106 T (K) P (bar) 353.2 180 0.44 200 0.94 220 1.24 240 1.86 260 3.20 280 3.72 300 4.65 373.2 180 0.48 200 1.00 220 1.86 240 3.20 260 4.23 280 4.75 300 5.78 393.2 180 0.29 200 0.68 220 1.34 240 2.58 260 4.44 280 5.16 300 7.85 1: The information on the molecular structure is not available for this material. Source: Ferri, A.; Banchero, M.; Manna, L.; Sicardi, S. J. Supercrit. Fluids (2004), 30(1), 41-49.

3

0 150

200

250 P (bar)

C. I. Disperse Red W-4BS1) (MW=469)

[C-143]

106

20 323.15 K 373.15 K

y x 106

yx T (K) P (bar) 323.15 202.6 1.96 303.9 16.10 354.6 5.73 373.15 202.6 0.58 303.9 5.05 354.6 15.40 1: The molecular formula is not known for this material. Source: Draper, S. L.; Montero, G. A.; Smith, B.; Beck, K. Dyes Pigm. (2000), 45(3), 177-183.

300

10

0 150

CAT4240—CHAPTER 3—1/11/2006—17:30—SRIDHAR—XML MODEL C – pp. 151–270

250 P (bar)

350

238

Solubility in Supercritical Carbon Dioxide

C. I. Disperse Violet 91 (C22H24N6O9; MW=516.46) yx

1.20 5.85 9.24 0.33 5.99 21.00

323.15 K 373.15 K

20 y x 106

T (K) P (bar) 323.15 202.6 303.9 405.2 373.15 202.6 303.9 405.2

[C-144]

106

10

Synonym: N-[5-[Bis[2-(acetyloxy)ethyl] amino]-2-[(2,4-dinitrophenyl)azo]phenyl] acetamide Source: Draper, S. L.; Montero, G. A.; Smith, B.; Beck, K. Dyes Pigm. (2000), 45(3), 177-183.

0 150

250

350 P (bar)

C. I. Disperse Yellow 7 (C19H16N4O; MW=316.36) y × 106 1.68 2.07 2.48 2.92 1.32 1.90 2.62 3.48

[C-145] 4

y x 106

T (K) P (bar) 333.15 132 152 172 193 353.15 132 152 172 193

2 333.15 K 353.15 K

0 120

Synonym: 2-Methyl-4-[[4-(phenylazo) phenyl]azo]phenol Source: Guzel, B.; Akgerman, A. J. Chem. Eng. Data (1999), 44(1), 83-85.

160

200

P (bar)

C. I. Disperse Yellow 7 (C19H16N4O; MW=316.36)

[C-146]

y x 106 0.399 0.936 2.971 4.075 0.121 0.333 4.706 9.644 0.479 1.335 8.840 20.190

313.15 K 353.15 K 393.15 K

20 y x 106

T (K) P (bar) 313.15 100 150 200 250 353.15 100 150 200 250 393.15 100 150 200 250

450

10

0 50

Synonym: 2-Methyl-4-[[4-(phenylazo) phenyl]azo]phenol Source: Joung, S. N.; Yoo, K.-P. J. Chem. Eng. Data (1998), 43(1), 9-12.

CAT4240—CHAPTER 3—1/11/2006—17:30—SRIDHAR—XML MODEL C – pp. 151–270

150 P (bar)

250

Solubility Data C

239

C. I. Disperse Yellow 16 (C16H14N4O; MW=278.31) yx

2.2 21.1 54.5 96.1 136.5 0.9 3.3 20.9 99.9 220.3 2.1 5.4 17.8 96.2 269.4

[C-147]

300

y x 106

T (K) P (bar) 323.15 100 120 150 200 250 353.15 100 120 150 200 250 383.15 100 120 150 200 250

106

323.15 K 353.15 K 383.15 K

200

100

0 50

150

250

P (bar)

Synonym: 3-Methyl-1-phenyl-4-(phenylazo)-pyrazol-5-ol Source: Tamura, K.; Shinoda, T. Fluid Phase Equil.(2004), 219(1), 25-32.

C. I. Disperse Yellow 42 (C18H15N3O4S; MW=369.39) 20 y x 106

y x 106 T (K) P (bar) 323.15 202.6 16 373.15 303.9 19 Synonym: 4-Anilino-3nitrobenzenesulfonanilide Source: Draper, S. L.; Montero, G. A.; Smith, B.; Beck, K. Dyes Pigm. (2000), 45(3), 177-183.

[C-148]

323.15 K 373.15 K

15 150

250 P (bar)

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350

240

Solubility in Supercritical Carbon Dioxide

[C-149]

C. I. Disperse Yellow 54 (C18H11NO3; MW=289.28) 106

y x 106

yx T (K) P (bar) 333.15 132.0 2.79 137.7 3.51 151.0 3.84 162.8 4.17 192.0 4.73 228.5 5.35 242.3 5.64 279.2 6.05 328.5 6.95 363.15 129.2 2.48 147.2 3.55 160.0 4.17 167.3 4.48 188.8 5.21 197.2 5.58 204.4 6.12 239.6 7.60 274.2 9.12 333.0 11.28 393.15 144.9 5.19 158.9 6.29 161.3 6.67 168.1 7.02 182.0 7.69 204.3 8.96 231.0 10.79 275.3 13.54 308.0 16.80 343.3 20.39 423.15 145.0 8.51 169.0 9.87 185.2 11.92 203.6 13.82 217.3 16.41 235.4 17.88 267.8 22.35 306.8 26.50 343.1 32.58 Synonyms: 2-(3-Hydroxy-2-quinolyl)-1,3indanedione; C. I. Solvent Yellow 114 Source: Shim, J.-J.; Baek, J.-K.; Sung, H.-D.; Lee, K.-H.; Choi, J.-H. Proceedings of the 6th Conference on Supercritical Fluids and Their Applications, Maiori, Italy, (Sep. 12, 2001), 565-570. (Data from Baek's thesis).

30

333.15 K 363.15 K 393.15 K 423.15 K

20

10

0 100

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200 P (bar)

300

Solubility Data C

241

C. I. Disperse Yellow 82 (C20H19N3O2; MW=333.38) yx

0.60 1.66 2.38 0.79 2.41 4.14

353.15 K 373.15 K

4 y x 106

T (K) P (bar) 353.15 200 250 300 373.15 200 250 300

[C-150]

106

Synonym: 3-(2-Benzimidazolyl)-7(diethylamino)coumarin Source: Oezcan, A. S.; Clifford, A. A.; Bartle, K. D.; Lewis, D. M. J. Chem. Eng. Data (1997), 42(3), 590-592.

2

0 150

250 P (bar)

C. I. Disperse Yellow 86 (C16H19N3O5S; MW=365.40)

[C-151]

120 y x 106

y x 106 T (K) P (bar) 323.15 202.6 79.2 303.9 90.4 373.15 202.6 24.3 303.9 106.0 Synonym: 4-(4-Ethoxyanilino)-N,Ndimethyl-3-nitrobenzenesulfonamide Source: Draper, S. L.; Montero, G. A.; Smith, B.; Beck, K. Dyes Pigm. (2000), 45(3), 177-183.

60

323.15 K 373.15 K

0 150

250

yx

[C-152]

106

323.15 202.6 8.37 303.9 3.70 354.6 8.12 373.15 202.6 1.06 303.9 3.35 354.6 38.40 1: The molecular formula is not known for this material. Source: Draper, S. L.; Montero, G. A.; Smith, B.; Beck, K. Dyes Pigm. (2000), 45(3), 177-183.

50 y x 106

P (bar)

350

P (bar)

C. I. Disperse Yellow 1081) (MW=429) T (K)

350

323.15 K 373.15 K

25

0 150

CAT4240—CHAPTER 3—1/11/2006—17:30—SRIDHAR—XML MODEL C – pp. 151–270

250 P (bar)

350

242

Solubility in Supercritical Carbon Dioxide

C. I. Disperse Yellow 119 (C15H13O4N5; MW=327.30)

[C-153]

106

y x 106

yx T (K) P (bar) 353.2 150 0.07 200 0.45 250 1.36 300 2.39 373.2 150 0.07 200 0.49 250 1.53 300 3.29 393.2 150 0.09 200 0.62 250 2.58 300 6.31 Synonym: 1-Ethyl-6-hydroxy-4-methyl-5(2-nitro-phenylazo)-2-oxo-1,2-dihydropyridine-3-carbonitrile Source: Lin, H. m.; Liu, C. Y.; Cheng, C. H.; Chen,Y.-T. ; Lee, M.-J. J. Supercrit. Fluids (2001), 21(1), 1-9.

6

353.2 K 373.2 K 393.2 K

4 2 0 100

200

C. I. Modified Yellow 119 (C15H12ClN5O4; MW=361.74) y x

0.10 1.44 3.99 7.53 0.06 0.87 3.60 9.92 0.04 0.35 3.31 10.70

[C-154]

12

y x 106

T (K) P (bar) 353.2 150 200 250 300 373.2 150 200 250 300 393.2 150 200 250 300

106

300

P (bar)

8

353.2 K 373.2 K 393.2 K

4

0 100

Synonym: 5-(4-Chloro-2nitrophenylazo)-3-cyano-1-ethyl-6hydroxy-4-methyl-1H-pyridin-2-one Source: Lin, H.-m.; Ho, C.-C.; Lee, M.-J. J. Supercrit. Fluids (2004), 32(1-3), 105-114.

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200 P (bar)

300

Solubility Data C

243

C. I. Mordant Brown (C10H7NO2; MW=173.17) y×

220 317 423 480 129 256 416 515 Synonym: 2-Nitroso-1-naphthol Source: Guzel, B.; Akgerman, A. J. Chem. Eng. Data (1999), 44(1), 83-85.

[C-155]

600

y x 106

T (K) P (bar) 333.15 132 155 175 195 353.15 134 154 176 195

106

300 333.15 K 353.15 K

0 120

160 P (bar)

200

C. I. Mordant Red 11 (C14H8O4; MW=240.22) y×

8

2.66 3.91 5.19 6.28 1.76 3.16 5.16 6.56

yx

106

T (K) P (bar) 333.15 132 155 176 189 353.15 133 154 175 192

[C-156]

106

Synonyms: 1,2-Dihydroxyanthraquinone; Alizarin Source: Guzel, B.; Akgerman, A. J. Chem. Eng. Data (1999), 44(1), 83-85.

4 333.15 K 353.15 K

0 120

150

180

C. I. Mordant Yellow 12 (C13H10N3NaO3; FW=279.23) y×

0.32 0.35 0.44 0.49 0.17 0.26 0.37 0.51

Synonym: 5-(4-aminophenylazo)-2hydroxybenzoic acid sodium salt Source: Guzel, B.; Akgerman, A. J. Chem. Eng. Data (1999), 44(1), 83-85.

[C-157]

0.8 y x 106

T (K) P (bar) 333.15 132 154 175 198 353.15 133 154 175 189

106

210

P (bar)

333.15 K 353.15 K

0.4

0 120

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150

180 P (bar)

210

244

Solubility in Supercritical Carbon Dioxide

Cineole (C10H18O; MW=154.25 ) T (K) P1) (bar) S1,2)(g/L)

[C-158]

y3) x 106

7850 80 0.051 12000 100 0.078 17400 150 0.114 24200 250 0.160 2320 333.15 80 0.015 6320 100 0.041 12300 150 0.080 250 0.106 16200 1: Obtained by digitizing the graph in the original article. 2: Solubility is based on 1 liter of CO2 at 293.15 K and 1 atm. 3: Calculated from S. Synonyms: 1,8-Cineole; 1,8-Epoxy-p-menthane Source: Francisco, J. C.; Sivik, B. J. Supercrit. Fluids(2002), 23(1), 11-19.

y x 106

313.15

30000 313 K 333 K

20000 10000 0 50

150 P (bar)

[C-159]

Cineole (C10H18O; MW=154.25) Ethane1) y x 106 (mol %) 303.2 66.0 23.2 7000 68.0 23.2 14000 69.0 23.2 18000 318.2 80.0 0.0 5000 84.0 0.0 5000 86.0 0.0 9000 88.0 0.0 8000 89.5 0.0 18000 90.0 0.0 30000 90.0 0.0 21000 323.2 77.5 0.0 6000 80.0 0.0 5000 84.0 0.0 5000 88.0 0.0 5000 92.0 0.0 4000 94.0 0.0 4000 96.0 0.0 12000 98.0 0.0 23000 1: Cosolvent in CO2. Synonyms: 1,8-Cineole; 1,8-Epoxy-p-menthane Source: Matos, H. A.; de Azevedo, E. G.; Simoes, P. C.; Carrondo, M. T.; da Ponte, N. M.Fluid Phase Equil.(1989), 52, 357-364. P (bar)

y x 106

T (K)

250

40000 w/Eth 303.2 K CO2 318.2 K CO2 323.2 K

30000

20000

10000

0 60

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80 P (bar)

100

Solubility Data C

245

trans-Cinnamic acid (C9H8O2; MW=148.16)

313.15

80 85 90 100 120 150 200

(mg/Nl2)) 0.020 0.067 0.157 0.397 0.700 1.010 1.420

[C-160]

y3) x 106 3.0 10.1 23.6 59.7 105.0 152.0 213.0

200 y x 106

P1) (bar)

T(K)

S1)

100

1: Obtained by digitizing the graph in the original article. 2: "Nl" means "Normliter," which is one liter at 273.15 K and 1 atm. 3: Calculated from S. Synonyms: (E)-3-Phenyl-2-propenoic acid; trans-3Phenylacrylic acid Source: Stahl, E.; Schilz, W.Talanta(1979), 26, 675-679.

0 50

100

150 P (bar)

C. I. Solvent Blue 35 (C22H26N2O2; MW=350.45) T (K) 323.15

353.15

373.15

398.15

408.15

418.15

(bar)

75.9 84.8 100.8 135.3 180.5 231.9 50.6 127.3 176.0 225.8 32.4 107.8 170.9 219.2 14.6 87.7 153.3 209.1 85.5 147.3 204.3 0.0 76.5 138.7 195.5

y1) x

[C-161]

106

0.00 1.02 2.54 9.32 26.61 40.51 0.00 4.13 31.68 69.34 0.00 3.21 28.47 70.71 0.00 2.30 27.09 75.31 2.30 22.50 65.66 0.00 1.84 21.12 61.07

80 323.15 K 353.15 K 373.15 K 398.15 K 408.15 K 418.15 K

60 y x 106

P1)

200

40

20

0 0

1: Obtained by digitizing the graph in the original article. Synonyms: 1,4-Bis(butylamino)anthraquinone; Sudan Blue II Source: Tabata, I.; Lyu, J.; Cho, S.; Tominaga, T.; Hori, T.Coloration Tech. (2001), 117(6), 346-351.

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100 P (bar)

200

246

Solubility in Supercritical Carbon Dioxide

C. I. Solvent Brown 1 (C16H14N4; MW=262.31) 353.2

373.2

393.2

P (bar) 204 220 240 283 304 181 201 221 244 260 280 300 221 240 260 280 300

yx

2.83 4.57 6.92 11.80 13.70 1.29 2.45 4.52 7.28 9.80 13.80 16.80 3.86 5.70 8.89 15.80 20.80

20

y x 106

T (K)

[C-162]

106 353.2 K 373.2 K 393.2 K

10

0 150

200

250

300

P (bar)

Synonyms: 4-(1-Naphthalenylazo)-1,3benzenediamine; Fat Brown RR Source: Ferri, A.; Banchero, M.; Manna, L.; Sicardi, S. J. Supercrit. Fluids (2004), 32(1-3), 27-35.

Citral (C10H16O; MW=152.23) y1)

[C-163] 106

x wx T (K) P(bar) 315 47.0 200 58 60.0 300 87 70.0 500 145 76.5 800 231 80.0 1300 376 86.5 7200 2090 87.5 5900 1710 90.0 7600 2210 91.1 8600 2500 95.8 34800 10300 1: Calculated from w. Synonym: 3,7-Dimethyl-2,6-octadienal Source: Benvenuti, F.; Gironi, F. J. Chem. Eng. Data (2001), 46(4), 795-799.

12000 y x 106

106

6000

0 40

Citral (C10H16O; MW=152.23) T(K) 308.2

P(bar) 30.0 40.0 50.0 60.0 70.0

y x 106 30 40 60 80 190

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60

80

100

P (bar)

[C-164]

Solubility Data C

247

308.2 K 315.0 K 323.2 K

y x 106

75.0 340 100000 77.5 9560 80.0 21600 315.0 30.0 40 10000 40.0 50 50.0 70 60.0 90 70.0 190 1000 80.0 380 85.0 520 87.5 590 88.8 7930 100 90.0 12900 100.0 22300 323.2 30.0 70 40.0 80 10 50.0 100 0 60.0 120 70.0 180 80.0 220 90.0 280 100.0 540 105.0 4500 16100 110.0 Synonym: 3,7-Dimethyl-2,6-octadienal Source: Di Giacomo, G.; Brandiani, V.; Del Re, G.; Mucciante, V. Fluid Phase Equil. (1989), 52. 405-411.

50

Clove ( Eugenia caryophillus1) ) buds extract T (K)

P (bar)

W (g/kg)

w2)x

106

[C-165]

220000

283.15 288.15

w x 106

66.7 258 205000 66.0 220 180000 66.7 234 190000 70.0 230 187000 72.0 238 192000 80.0 244 196000 100.0 277 217000 298.15 100.0 267 211000 308.15 100.0 230 187000 1: A Brazilian tree. 2: Calculated from W. Source: Rodrigues,V.M.;Sousa,E.M.B. D.; Monteiro, A. R.; Chiavone-Filho, O.; Marques, M. O. M.; Meireles, M. A.A. J. Supercrit. Fluids (2002), 22(1), 21-36.

100

P (bar)

283.15 K 288.15 K 298.15 K 308.15 K

200000

180000 60

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80 P (bar)

100

248

Solubility in Supercritical Carbon Dioxide

Cobalt bis (acetylacetonate) (C10H14CoO4; FW=257.15) y x 106 (wt%) 333.15 101 0 0.0026 203 0 0.0156 304 0 0.0334 405 0 0.0404 293.15 405 0 0.0041 333.15 405 0 0.0115 373.15 405 0 0.0404 373.15 405 10 0.0690 1: Cosolvent in CO2. Synonyms: Bis(2,4pentanedionato)cobalt; Co(acac)2 Source: Ozel, M. Z.; Bartle, K. D.; Clifford, A. A.; Burford, M. D. Anal. Chim. Acta (2000), 417(2), 177-184.

[C-166]

0.05 y x 106

P (bar)

0.00 0

200 P (bar)

400

0.10 y x 106

T (K)

Methanol1)

0 wt% MeOH 10 wt% MeOH

0.05 0.00 250

300

350

400

T (K)

Cobalt bis(hexafluoroacetylacetonate) (C10H2CoF12O4; FW=473.03)

[C-167]

0.8 y x 106

Methanol1) T (K) P (bar) y x 106 (wt%) 373.15 405 0 0.270 10 0.585 1: Cosolvent in CO2. Synonyms: Co(hfa)2; Bis(1,1,1,5,5,5hexafluoro-2,4-pentanedionato)cobalt Source: Ozel, M. Z.; Bartle, K. D.; Clifford, A. A.; Burford, M. D. Anal. Chim. Acta (2000), 417(2), 177-184.

0.4 0 0

5 Methanol (wt%)

Cobalt tris(acetylacetonate) (C15H21CoO6; FW=356.26) 333

(bar) 98 196 294

S1)

(mg/L) 0.045 0.106 0.582

y2)

x

106

0.0196 0.0182 0.0869

1: Obtained by digitizing from the original article. 2. Calculated from S. Synonyms: Co(acac)3; Tris(2,4pentanedionato)cobalt Source: Saito, N.; Ikushima, Y.; Goto, T. Bull. Chem. Soc. Japan (1990), 63(5), 1532-1534.

[C-168]

0.1 y x 106

T (K)

P1)

10

0 50

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150

250 P (bar)

350

Solubility Data C

249

Cocoa Butter1)

[C-169]

w x 106

T (K) P2) (bar) w3) x 106 8000 313.15 96 400 148 1900 198 3450 245 4950 4000 290 7500 333.15 150 750 198 1500 248 2950 0 295 6300 50 1: Extract of cocoa bean (Theobroma cacao). 2: Calculated from density and temperature data. 3: Obtained by digitizing the graph in the original article. Source: Li, S.; Hartland, S. J. Supercrit. Fluids (1992), 5(1), 7-12.

313.15 K 333.15 K

150

250 P (bar)

Cocoa Butter1) T (K) P2) (bar)

350

[C-170] Ethanol3)

w x 106

w4) x 106 600000 (wt%) 333.15 59 20~25 5300 81 20~25 26300 100 20~25 242100 300000 149 20~25 452600 150 20~25 505300 201 20~25 447400 201 20~25 494700 0 251 20~25 457900 50 250 20~25 484200 300 20~25 473700 300 20~25 505300 1: Extract of cocoa bean (Theobroma cacao). 2: Calculated from density and temperature data. 3: Cosolvent in CO2 on a solute-free basis. 4: Obtained by digitizing the graph in the original article. Source: Li, S.; Hartland, S. J. Supercrit. Fluids (1992), 5(1), 7-12.

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150 P (bar)

250

250

Solubility in Supercritical Carbon Dioxide

Codeine (C18H21NO3; MW=299.36) S (g/L) 0.53 0.69 1.05 1.13 1.45 1.56 1.87 1.96 2.40 0.28 0.62 1.08 1.43 1.67 2.00 2.09 2.44 2.65 0.29 0.65 1.15 1.54 1.85 2.45 2.71 3.03 3.53 0.44 0.48 0.92 1.36 2.17 2.73 3.25 3.78 4.85 0.10 0.30 0.78 1.51 2.75 3.66 4.71 5.22 7.97

yx

100 120 180 190 240 250 300 300 370 60 120 200 250 290 340 340 390 420 80 150 230 290 340 430 470 510 590 160 120 210 280 420 510 590 670 840 40 90 200 340 580 730 900 960 1230

308 K 318 K 328 K 338 K 348 K

1200

800 y x 106

T (K) P (bar) 308 122 152 182 213 243 274 304 334 355 318 122 152 182 213 243 274 304 334 355 328 122 152 182 213 243 274 304 334 355 338 122 152 182 213 243 274 304 334 355 348 122 152 182 213 243 274 304 334 355

[C-171]

106

400

0 100

Synonym: Methylmorphine Source: Yamini, Y.; Hassan, J.; Haghgo, S. J. Chem. Eng. Data (2001), 46(2), 451-455.

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200

300 P (bar)

400

Solubility Data C

251

Coenzyme Q10 (C59H90O4; MW=863.34) S (g/L) 0.24 0.48 0.88 1.15 1.25 1.79 0.14 0.43 0.69 1.10 1.97 0.0 0.10 0.18 0.37 0.74 1.56

yx

15.7 29.9 52.1 65.1 69.7 99.1 9.90 27.8 42.4 66.2 112.9 00 7.4 13.0 25.1 46.2 95.6

120 305 K 313 K 323 K

80 y x 106

T (K) P (bar) 305 116 141 178 222 229 259 313 121 158 184 211 262 323 121 142 158 181 217 253

[C-172]

106

40

0 50

150 P (bar)

250

Synonym: Ubiquinone 10; (all-E)-2(3,7,11,15,19,23, 27,31,35,39-Decamethyl2,6,10,14,18,22,26,30,34,38-tetracontadecaenyl)-5,6dimethoxy-3-methyl-p-benzoquinone Source: Matias, A. A.; Nunes, A. V. M.; Casimiro, T.; Duarte, C. M. M. J. Supercrit. Fluids (2004), 28(2-3), 201-206.

Copper bis(acetylacetonate) (C10H14CuO4; FW=261.76) yx

3.04 10.80

Synonyms: Bis(2,4-pentane dionato)copper; Cu(acac)2 Source: Guigard, S. E.; Hayward, G. L.; Zytner, R. G.; Stiver, W. H. Fluid Phase Equil. (2001), 187-188, 233-246.

[C-173]

14 y x 106

T(K) P (bar) 318.0 100.0 312.8 103.4

106

318.0 K 312.8 K

7 0

95

100 P (bar)

[C-174]

Copper bis(acetylacetonate) (C10H14CuO4; FW=261.76) y x 106 7.5 13.0 16.1 18.5 20.1 21.2 22.3 23.1

30 y x 106

T (K) P (bar) 313.15 103.4 137.9 172.4 206.8 241.3 275.8 310.3 344.7

105

15

0 50

Synonyms: Bis(2,4-pentanedionato)copper; Cu(acac)2 Source: Lagalante, A. F.; Hansen, B. N.; Bruno, T. J.; Sievers, R. E. Inorg. Chem. (1995), 34(23), 5781-5785.

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150

250 P (bar)

350

252

Solubility in Supercritical Carbon Dioxide

Copper bis(acetylacetonate) (C10H14CuO4; FW=261.76) yx

[C-175]

200

6.2 47.5 72.5 25.0 110.0 155.0

y x 106

T (K) P (bar) 423.15 120 170 220 443.15 120 170 220

106

423 K 443 K

100

Synonyms: Bis(2,4-pentane dionato)copper; Cu(acac)2 Source: M'Hamdi, R.; Bocquet, J.; Chhor, K.; Pommier, C. J. Supercrit. Fluids (1992), 5(1), 55-9.

0 100

150

200

Copper bis(acetylacetonate) (C10H14CuO4; FW=261.76) T (K)

P1)

(bar)

S1)

(mg/L)

y2)

x

106

[C-176]

20

333

y x 106

98 0.011 1.0 196 0.103 9.4 294 0.207 18.9 1: Obtained by digitizing the graph in the original article. S is expressed in mg/liter of gas at atmospheric pressure. 2. Calculated from S, assuming that the gas volume is based on room temperature (20˚C). Synonym: Bis(2,4-pentane dionato)copper; Cu(acac)2 Source: Saito, N.; Ikushima, Y.; Goto, T. Bull. Chem. Soc. Japan (1990), 63(5), 1532-1534.

10

0 50

150

250

333

(bar) 98 196 294

(mg/L) 0.0094 0.0790 0.1610

y3)

x

106

0.77 6.45 13.14

1: The weight of dihydrate is included. 2: Obtained by digitizing the graph in the original article. S is expressed in mg/liter of gas at atmospheric pressure.

[C-177]

16 y x 106

T (K)

S2)

350

P (bar)

Copper bis(acetylacetonate) dihydrate (C10H14CoO4·2H2O; FW=293.181)) P2)

250

P (bar)

2. Calculated from S, assuming that the gas volume is based on room temperature (20˚C). Synonym: Bis(2,4-pentanedionato)copper dihydrate Source: Saito, N.; Ikushima, Y.; Goto, T. Bull. Chem. Soc. Japan (1990), 63(5), 1532-1534.

8

0 50

CAT4240—CHAPTER 3—1/11/2006—17:30—SRIDHAR—XML MODEL C – pp. 151–270

150

250 P (bar)

350

Solubility Data C

253

Copper bis(2,6-dimethylheptane-3,5-dionate) (C18H30CuO4; FW=373.98) P (bar)

313.15 103.4 137.9 172.4 206.8 241.3 275.8 310.3 344.7

yx

91.7 272.6 386.0 461.9 561.3 730.5 794.2 884.1

[C-178]

1000 y x 106

T (K)

106

500

0 50

Synonyms: Bis(2,6-dimethylheptane3,5-dionato)copper; Cu(dibm)2 J.; Sievers, R. E. Inorg. Chem. (1995), 34(23), 5781-5785. Source : Lagalante, A. F.; Hansen, B. N.; Bruno, T. J.; Sievers, R. E. Inorg. Chem. (1995), 34(23), 5781-5785.

150

250 P (bar)

350

Copper bis(5,5-dimethylhexane-2,4-dionate)1) (C16H26CuO4; FW=345.93) yx

37.0 154.0 205.1 260.4 321.1 340.1 362.1

[C-179]

400 y x 106

T (K) P (bar) 313.15 137.9 172.4 206.8 241.3 275.8 310.3 344.7

106

200 0 100

1: In the source article the compound is named Bis(1,1-dimethylhexane-3,5dionato)copper(II), which is not a correct name. Synonyms: Bis(5,5-dimethylhexane-2,4dionato)copper; Cu(dmhd)2

200

300

400

P (bar)

Copper bis(1,1,1,6,6,6-hexafluoroacetylacetonate) (C10H2CuF12O4; FW=477.65) [C-180]

y x 106 2251 3211 3535 3820 4497 5027 5699

Synonyms: Bis(1,1,1,6,6,6-hexafluoro pentane-2,4-dionato)copper; Cu(hfa)2 Source: Lagalante, A. F.; Hansen, B. N.; Bruno, T. J.; Sievers, R. E. Inorg. Chem. (1995), 34(23), 5781-5785.

7000 y x 106

T (K) P (bar) 313.15 103.4 137.9 172.4 206.8 241.3 275.8 310.3

4000

1000 50

CAT4240—CHAPTER 3—1/11/2006—17:30—SRIDHAR—XML MODEL C – pp. 151–270

150

250 P (bar)

350

254

Solubility in Supercritical Carbon Dioxide

[C-181]

Copper bis(1,1,1,6,6,6-hexafluoroacetylacetonate)hydrate (C10H2CuF12O4H2O; FW=495.67) 10000 y x 106

M x 102 y1) x 106 (mol/L) 313 70 1.0 2190 90 3.0 2610 100 11.0 7550 110 13.0 8240 1: Calculated from M. Synonyms: Bis(1,1,1,6,6,6-hexafluoro pentane-2,4-dionato)copper hydrate; Cu(hfa)2 H2O Source: Fedotov, A. N.; Simonov, A. P.; Popov, V. K.; Bagratashvili, V. N. J. Phys. Chem. B (1997),101(15), 2929-2932. T (K) P (bar)

5000

0 50

70

90

110

P (bar)

[C-182]

Copper bis(1,1,1,6,6,6-hexafluoroacetylacetonate)hydrate (C10H2CuF12O4H2O; FW=495.67) y x 106 1520 1741 2063 2417 2610 2913 3320 4140

5000 y x 106

T (K) P (bar) 313.15 103.4 137.9 172.4 206.8 241.3 275.8 310.3 344.7

3000

1000

Synonyms: Bis(1,1,1,6,6,6-hexafluoro pentane-2,4-dionato)copper hydrate; Cu(hfa)2 H2O Source: Lagalante, A. F.; Hansen, B.N. Bruno,T.J.; Sievers, R. E. Inorg. Chem. (1995), 34(23), 5781- 5785.

50

150

250

61.7 303.5 446.9 582.4 627.4 679.7 716.4 741.5

[C-183]

800 y x 106

yx

106

350

P (bar)

Copper bis(2,2,6,6-tetramethylheptane-3,5-dionate) (C22H38CuO4; FW=430.09) T (K) P (bar) 313.15 103.4 137.9 172.4 206.8 241.3 275.8 310.3 344.7

130

400 0 50

Synonym: Bis(2,2,6,6-tetramethyl heptane-3,5-dionato)copper; Cu(thd)2 Source: Lagalante, A. F.; Hansen, B. N.; Bruno, T.J.; Sievers, R. E. Inorg. Chem. (1995), 34(23), 5781-5785.

CAT4240—CHAPTER 3—1/11/2006—17:30—SRIDHAR—XML MODEL C – pp. 151–270

150

250 P (bar)

350

Solubility Data C

255

Copper bis(2,2,6,6-tetramethylheptane-3,5-dionate) (C22H38CuO4; FW=430.09) Mx 5000 y1) x 106 (mol/L) 313.15 100 89 141 130 289 388 2500 150 778 994 200 1110 1317 250 1560 1768 300 3780 4131 0 3780 3933 400 0 1: Obtained by digitizing the graph in the original article. Synonym: Bis(2,2,6,6-tetramethyl heptane-3,5-dionato)copper; Cu(thd)2 Source: Wenclawiak, B. W.; Wolf, A.; Wilnewski, S. in: Supercritical Fluids as Solvents and Reaction Media, Brunner, G. (ed.), Elsevier B.V., Amsterdam, Netherlands (2004), 323-340. P (bar)

y x 106

T (K)

[C-184]

106

150

300 P (bar)

[C-185]

Copper bis(thenoyltrifluoroacetonate) (C16H8CuF6O4S2; FW=505.89) 106

4 y x 106

yx T(K) P(bar) 317.8 96.5 0.70 313.0 103.4 3.26 Synonym: Bis[4,4,4-trifluoro-1-(2thienyl)-1,3-butanedionato]copper Source: Guigard, S. E.; Hayward, G. L.; Zytner, R. G.; Stiver, W. H. Fluid Phase Equil. (2001),187-188, 233-246.

450

317.8 K 313.0 K

2 0 90

95

100

105

P (bar)

Copper bis(1,1,1-trifluoroacetylacetonate) (C10H8CuF6O4; FW=369.71) P (bar)

313.15 103.4 137.9 172.4 206.8 241.3 275.8 310.3 344.7

y x 106 296.0 313.3 352.7 420.8 481.8 546.2 573.8 593.8

700 y x 106

T (K)

[C-186]

450

200 50

Synonyms: Bis(1,1,1-trifluoropentane2,4-dionato)copper; Cu(tfa)2 Source: Lagaiante, A. F.; Hansen, B. N.; Bruno, T. J.; Sievers, R. E. Inorg. Chem. (1995), 34(23), 5781-5785.

CAT4240—CHAPTER 3—1/11/2006—17:30—SRIDHAR—XML MODEL C – pp. 151–270

150

250 P (bar)

350

256

Solubility in Supercritical Carbon Dioxide

[C-187]

Copper bis(1,1,1-trifluoro-4-phenylbutane-2,4-dionate) (C20H12CuF6O4; FW=493.85) 50 y x 106

y x 106 T (K) P (bar) 313.15 137.9 7.02 172.4 14.24 206.8 21.13 241.3 27.40 275.8 33.13 310.3 38.43 344.7 42.69 Synonyms: Bis(4,4,4-trifluoro-1-phenyl butane-1,3-dionato)copper; Cu(tfbzm)2 Source: Lagalante, A. F.; Hansen, B. N.; Bruno, T. J.; Sievers, R. E. Inorg. Chem. (1995), 34(23), 5781-5785.

25

0 100

200

300

400

P (bar)

[C-188]

Copper bis(2,2,7-trimethyloctane-3,5-dionate) (C22H38CuO4; FW=430.09)

y x 106

y x 106 T (K) P (bar) 3000 313.15 103.4 260 137.9 490 172.4 775 1500 206.8 1141 241.3 1488 275.8 1810 310.3 2128 0 344.7 2697 0 Synonym: Bis(2,2,7-trimethyloctane-3,-5 dionato)copper; Cu(tod)2 Source: Lagalante, A. F.; Hansen, B. N.; Bruno, T. J.; Sievers, R. E. Inorg. Chem. (1995), 34(23), 5781-5785.

100

200 P (bar)

106

M x y1) x 106 (mol/L) Copper Pyrrolidinedithiocarbamate (PDC) (C10H16CuN2S4; FW=356.04) P (bar)

250

333.15

101 1.4 0.21 233 11.0 0.63 Copper bis(dipropyldithiocarbamate) (P3DC) (C14H28CuN2S4; FW=416.18) 333.15

101 6.3 0.93 233 120.0 6.90 Copper bis(dibutyldithiocarbamate) (BDC) (C18H36CuN2S4; FW=472.28) 333.15

101

13

1.91

PDC DDC P3DC BDC P5DC HDC TFDC

200

333.15

y x 106

101 0.41 0.06 233 4.00 0.23 Copper bis(diethyldithiocarbamate) (DDC) (C10H20CuN2S4; FW=360.07)

400

[C-189]

Copper dithiocarbamate Complexes T (K)

300

150 100 50 0 0

CAT4240—CHAPTER 3—1/11/2006—17:30—SRIDHAR—XML MODEL C – pp. 151–270

100

200 P (bar)

300

Solubility Data C

257

233 720 41.10 Copper bis(dipentyldithiocarbamate) (P5DC) (C22H44CuN2S4; FW=528.39) 333.15

101 90 13.30 233 1800 102.80 Copper bis(dihexyldithiocarbamate) (HDC) (C26H52CuN2S4; FW=584.50) 333.15

101 210 30.90 233 2800 160.00 Copper bis[bis(trifluoroethyl)dithiocarbamate] (TFDC) (C10H8CuF12N2S4; FW=575.95) 333.15

101 910 134.00 233 4000 228.00 1: Calculated from M. Source: Wai, C. M.; Wang, S.; Yu, J.-J. Anal. Chem. (1996), 68(19), 3516-3519. [C-190]

Copper(II) hydrogen arsenate (AsHCuO4; MW=203.47) P (bar)

W x 105 (g/kg CO2)

0.02

y x 106

308.2

147 4.11 0.0091 245 5.20 0.0115 363.2 147 2.41 0.0054 245 2.96 0.0066 Source: Takeshita, Y.; Sato, Y. J. Supercrit. Fluids (2002), 24(2), 91-101.

y x 106

T (K)

308.2 K 363.2 K

0.01

0 100

200

300

P (bar) Cortisone acetate (C23H30O6; MW=402.48)

[C-191]

308.15 K 328.15 K 373.15 K

4

3 y x 106

T (K) P (bar) 308.15 82.4 99.0 113.8 129.4 146.1 160.8 177.5 196.1 210.8 226.5 328.15 82.4 99.0 113.8 129.4 146.1 160.8 177.5 196.1

y x 106 0.48 0.99 1.93 2.18 2.65 3.10 3.09 3.24 3.78 4.14 0.15 0.28 0.45 0.54 1.23 1.42 1.52 1.61

2

1

0

50

CAT4240—CHAPTER 3—1/11/2006—17:30—SRIDHAR—XML MODEL C – pp. 151–270

150 P (bar)

250

258

210.8 226.5 373.15 82.4 99.0 113.8 129.4 146.1 160.8 177.5 196.1 210.8 226.5

Solubility in Supercritical Carbon Dioxide

2.08 2.55 0.11 0.23 0.35 0.49 1.11 1.25 1.32 1.45 1.91 2.31

Synonym: 21-Acetoxy-17a-hydroxypregn-4-ene3,11,20-trione; Cortisone 21-acetate Source: Dean, J. R.; Kane, M.; Khundker, S.; Dowle, C.; Tranter, R. L.; Jones, P. Analyst (1995), 120(8), 2153-2157.

o -Coumaric acid (C9H8O3; MW=164.16)

[C-192]

106

y x 106

yx T (K) P (bar) 0.4 0.011 308.15 85 0.038 100 0.081 150 0.144 200 0.175 250 0.2 0.008 313.15 85 0.026 100 0.094 150 0.199 200 0.260 250 0.002 323.15 85 0.0 0.012 100 0 0.140 150 0.250 200 250 0.354 Synonyms: 2-Coumaric acid; 2-Hydroxycinnamic acid Source: Choi, E. S. ; Noh, M. J. ; Yoo, K.-P. J. Chem. Eng. Data (1998), 43(1), 6-8.

308.15 K 313.15 K 323.15 K

CAT4240—CHAPTER 3—1/11/2006—17:30—SRIDHAR—XML MODEL C – pp. 151–270

100

200 P (bar)

300

Solubility Data C

259

o -Coumaric acid (C9H8O3; MW=164.16) yx

0.032 0.046 0.086 0.148 0.196 0.011 0.039 0.117 0.170 0.278 0.002 0.014 0.179 0.254 0.390

0.4 308.15 K 313.15 K 323.15 K

y x 106

T (K) P (bar) 308.15 85 100 150 200 250 313.15 85 100 150 200 250 323.15 85 100 150 200 250

[C-193]

106

0.2

0.0 0

100

P (bar)

200

300

Synonyms: 2-Coumaric acid;2-Hydroxycinnamic acid Source: Choi, E. S.; Shin, H. Y.; You, S.-S.; Yoo, K.-P. Korean J. Chem. Eng. (1997), 14(4), 292-296.

m -Coumaric acid (C9H8O3; MW=164.16) 0.031 0.139 0.325 0.384 0.526 0.021 0.103 0.326 0.586 0.701 0.002 0.043 0.381 0.638 1.056

1.2

y x 106

T (K) P (bar) 308.15 85 100 150 200 250 313.15 85 100 150 200 250 323.15 85 100 150 200 250

[C-194]

y x 106

308.15 K 313.15 K 323.15 K

0.8

0.4

0.0 0

Synonyms: 3-Coumaric acid; 3-Hydroxycinnamic acid Source: Choi, E. S. ; Noh, M. J. ; Yoo, K.-P. J. Chem. Eng. Data (1998), 43(1), 6-8.

CAT4240—CHAPTER 3—1/11/2006—17:30—SRIDHAR—XML MODEL C – pp. 151–270

100

200 P (bar)

300

260

Solubility in Supercritical Carbon Dioxide

m -Coumaric acid (C9H8O3; MW=164.16) yx 0.092 0.153 0.283 0.376 0.534 0.030 0.102 0.302 0.502 0.725 0.002 0.052 0.524 0.715 1.330

1.5

y x 106

T (K) P (bar) 308.15 85 100 150 200 250 313.15 85 100 150 200 250 323.15 85 100 150 200 250

[C-195]

106

308.15 K 313.15 K 323.15 K

1.0

0.5

0.0 0

100

200

300

P (bar)

Synonyms: 3-Coumaric acid; 3-Hydroxycinnamic acid Source: Choi, E. S.; Shin, H. Y.; You, S.-S.; Yoo, K.-P. Korean J. Chem. Eng. (1997), 14(4), 292-296.

p -Coumaric acid (C9H8O3; MW=164.16) y x 106 0.015 0.056 0.117 0.157 0.176 0.008 0.027 0.147 0.209 0.270 0.005 0.006 0.163 0.275 0.385

[C-196]

0.4 308.15 K 313.15 K 323.15 K

y x 106

T (K) P (bar) 308.15 85 100 150 200 250 313.15 85 100 150 200 250 323.15 85 100 150 200 250

0.2

0.0 0

Synonyms: 4-Coumaric acid; 4-Hydroxycinnamic acid Source: Choi, E. S. ; Noh, M. J. ; Yoo, K.-P. J. Chem. Eng. Data (1998), 43(1), 6-8.

CAT4240—CHAPTER 3—1/11/2006—17:30—SRIDHAR—XML MODEL C – pp. 151–270

100

200 P (bar)

300

Solubility Data C

261

p -Coumaric acid (C9H8O3; MW=164.16) yx 0.034 0.058 0.108 0.165 0.176 0.011 0.026 0.118 0.225 0.294 0.006 0.009 0.177 0.280 0.350

0.4 308.15 K 313.15 K 323.15 K

y x 106

T (K) P (bar) 308.15 85 100 150 200 250 313.15 85 100 150 200 250 323.15 85 100 150 200 250

[C-197]

106

0.2

0.0 0

100 200 P (bar)

300

Synonyms: 4-Coumaric acid; 4-Hydroxycinnamic acid Source: Choi, E. S.; Shin, H. Y.; You, S.-S.; Yoo, K.-P. Korean J. Chem. Eng. (1997), 14(4), 292-296.

p -Coumaric acid (C9H8O3; MW=164.16) 0.4 313 K 323 K

yx

0.007 0.029 0.155 0.203 0.273 0.006 0.008 0.166 0.263 0.363

106

T (K) P (bar) 313 85 100 150 200 250 323 85 100 150 200 250

[C-198]

y x 106

0.2

0.0 50

Synonyms: 4-Coumaric acid; 4Hydroxycinnamic acid Source: Murga,R.;Sanz,M.T.;Beltran,S.; Cabezas, J. L. J. Supercrit. Fluids (2002), 23(2), 113-121.

CAT4240—CHAPTER 3—1/11/2006—17:31—SRIDHAR—XML MODEL C – pp. 151–270

150 P (bar)

250

262

Solubility in Supercritical Carbon Dioxide

p -Coumaric acid (C9H8O3; MW=164.16) yx 0.007 0.029 0.155 0.203 0.273 0.389 0.488 0.603 0.713 0.863 0.006 0.008 0.166 0.263 0.363 0.526 0.824 1.058 1.217 1.380 0.003 0.189 0.691 1.065 1.303 1.590 2.030 2.295 2.552

3 313 K 323 K 333 K

2 y x 106

T (K) P (bar) 313 85 100 150 200 250 300 350 400 450 500 323 85 100 150 200 250 300 350 400 450 500 333 100 150 200 250 300 350 400 450 500

[C-199]

106

1

0 0

200

400

600

P (bar)

Synonyms: 4-Coumaric acid; 4-Hydroxycinnamic acid Source: Murga,R.;Sanz,M.T.;Beltran,S.; Cabezas, J. L. J. Supercrit. Fluids (2003), 27(3), 239-245.

Coumarin (C9H6O2; MW=146.14)

313.15

70 80 85 90 120 150

0.18 0.60 1.99 7.00 35.00 51.50

27 91 303 1065 5304 7784

8000 y x 106

T(K) P1) (bar)

[C-200]

S1) (mg/Nl2)) y3) x 106

4000

0 1: Obtained by digitizing the graph in the original article. 60 2: "Nl" means "Normliter," which is one liter at 273.15 K and 1 atm. 3: Calculated from S. Synonym: 2H-1-Benzopyran-2-one Source: Stahl, E.; Schilz, W.Talanta(1979), 26, 675-679.

CAT4240—CHAPTER 3—1/11/2006—17:31—SRIDHAR—XML MODEL C – pp. 151–270

110 P (bar)

160

Solubility Data C

263

Coumarin (C9H6O2; MW=146.14)

[C-201]

106

3000 308.15 K 313.15 K 323.15 K

2000 y x 106

yx T (K) P (bar) 308.15 85 996 100 1183 150 1430 200 1790 250 2119 313.15 85 452 100 1532 150 1683 200 1873 250 2659 323.15 85 62 100 231 150 457 200 756 250 902 Synonym: 2H-1-Benzopyran-2-one Source: Yoo, K.-P.; Shin, H. Y.; Noh, M. J.; You, S. S.Korean J. Chem. Eng. (1997), 14(5), 341-346.

1000

0 50

150 P (bar)

p -Cresol(CO7H8; MW=108.14) yx

[C-202]

106

625 506 546 578 688 1050 1660 4080 10200 17800 22600 4570 3680 3210 3120 3120 3490 4270 6040 9460 17300

353.15 K 393.15 K 423.15 K

20000

y x 106

T(K) P(bar) 353.15 20 30 40 50 60 80 100 130 160 185 200 393.15 20 30 40 50 60 80 100 130 160 200

250

10000

0 0

CAT4240—CHAPTER 3—1/11/2006—17:31—SRIDHAR—XML MODEL C – pp. 151–270

100 P (bar)

200

264

Solubility in Supercritical Carbon Dioxide

423.15

20 13600 30 10400 40 8810 50 8660 60 8140 80 8290 100 8960 130 11200 160 14800 200 20800 Synonyms: 4-Methylphenol; 4-Cresol Source: Lee, M.-J.; Kou, C.-F.; Cheng, J.-W.; Lin, H.m. Fluid Phase Equil. (1999), 162(1-2), 211-224.

Cupuacu1) seed fat T (K) 323

P2)

(bar)

W2)

[C-203]

(g/kg)

w3)

x

106

12000

323 K 343 K

w x 106

151 0.0 0 248 3.5 3500 284 5.6 5600 8000 317 6.6 6600 352 8.1 8000 343 151 0.0 0 4000 248 2.5 2500 284 4.0 4000 317 6.6 6600 352 11.6 11500 0 1: A Brazilian Amazonian fruit 100 (Theobroma grandiflorum). 2: Obtained by digitizing the graph in the original article. 3: Calculated from W. Source: de Azevedo, A. B. A.; Kopcak, U.; Mohamed, R. S.J. Supercrit. Fluids (2003), 27(2), 223-237.

200

300 P (bar)

2-Cyanonaphthalene (C11H7N; MW=153.18) (bar) T (K) 308.15 96.8 114.2 141.6 176.3 211.0

y1)

x

106 643 1570 2650 3380 4020

[C-204]

5000 y x 106

P1)

400

1: Obtained by digitizing the graph in the original article. Synonyms: 2-Naphthonitrile; 2-Naphthalenenitrile Source: Nakatani, T.; Ohgaki, K.; Katayama, T. Ind. Eng. Chem. Res. (1991), 30(6), 1362-1366.

2500

0 50

CAT4240—CHAPTER 3—1/11/2006—17:31—SRIDHAR—XML MODEL C – pp. 151–270

150 P (bar)

250

Solubility Data C

265

a -Cyclodextrin octadecaacetate (C72H96O48; Mw=1729.50)

[C-205] 298 K 313 K

y x 106

T (K) P1) (bar) y1) x 106 9000 298 225.0 663 280.0 1344 306.8 2798 6000 345.0 8427 350.0 6327 313 275.0 663 3000 344.0 1327 392.0 2811 438.9 6310 0 449.0 8413 200 1: Obtained by digitizing the graph in the original article. Synonym: 2,3,6-Triacetyl-a-cyclodextrin Source: Potluri, V. K.; Hamilton, A. D.; Karanikas, C. F.; Bane, S. E., Xu, J.; Beckman, E. J.; Enick, R. M. Fluid Phase Equil. (2003), 211, 211–217.

300

400

P (bar)

b -Cyclodextrin heneicosaacetate (C84H112O56; Mw=2017.75)

[C-206]

298 K 313 K

y x 106

T (K) P1) (bar) y1) x 106 12000 298 195.0 530 278.8 1161 338.2 2411 8000 361.3 9226 371.2 5417 313 253.0 530 4000 346.5 1131 417.5 2411 447.2 5417 0 455.4 9226 150 1: Obtained by digitizing the graph in the original article. Synonym: 2,3,6-Triacetyl-b-cyclodextrin Source: Potluri, V. K.; Hamilton, A. D.; Karanikas, C. F.; Bane, S. E., Xu, J.; Beckman, E. J.; Enick, R. M. Fluid Phase Equil. (2003), 211, 211–217.

CAT4240—CHAPTER 3—1/11/2006—17:31—SRIDHAR—XML MODEL C – pp. 151–270

250

350 P (bar)

450

266

Solubility in Supercritical Carbon Dioxide

[C-207]

g -Cyclodextrin tetracosaacetate (C96H128O64; Mw=2306.03) (bar) T (K) 298 214.0 305.2 359.7 387.7 313 262.3 366.3 425.7 457.1 470.3

y1)

x

106

663 1012 2113 4732 506 982 2113 3363 4762

6000

y x 106

P1)

4000

298 K 313 K

2000

1: Obtained by digitizing the graph in the original article. Synonym: 2,3,6-Triacetyl-g -cyclodextrin Source: Potluri, V. K.; Hamilton, A. D.; Karanikas, C. F.; Bane, S. E., Xu, J.; Beckman, E. J.; Enick, R. M. Fluid Phase Equil. (2003), 211, 211–217.

0 200

300

400 P (bar)

Cyclododecene (C12H22; MW=166.30) T (K)

P (bar)

[C-208]

y x 106

20000

380

y x 106

200 12500 250 17000 423 200 13200 250 17200 Source: De Jong, A. ; Eftaxias, A. ; Trabelsi, F. ; Recasens, F. ; Sueiras, J.; Stueber, F. Ind. Eng. Chem. Res. (2001), 40(14), 3225-3229.

500

15000

380 K 423 K

10000 150

200

250

300

P (bar)

[C-209]

1,5,9-Cyclododecatriene (C12H18; MW=162.27) 380

P (bar) 200 250 200 250

yx

12500 18500 423 10900 13800 Source : De Jong, A. ; Eftaxias, A. ; Trabelsi, F. ; Recasens, F. ; Sueiras, J.; Stueber, F. Ind. Eng. Chem. Res. (2001), 40(14), 3225-3229.

20000 y x 106

T (K)

106

380 K 423 K

15000

10000 150

CAT4240—CHAPTER 3—1/11/2006—17:31—SRIDHAR—XML MODEL C – pp. 151–270

200 250 P (bar)

300

Solubility Data C

267

Cyclohexanone (C6H10O; MW=98.14)

[C-210]

106

yx T (K) P (bar) 100000 410 125.6 19700 150.5 25100 75000 165.8 29800 187.5 52500 204.7 90600 50000 423 139.1 12900 169.3 30200 190.5 56800 25000 204.9 82000 433 142.8 27800 0 157.5 28100 100 170.6 38000 190.9 54600 204.8 91800 Source: Mukhopadhyay, M.; Srinivas, P.Ind. Eng. Chem. Res. (1996), 35(12), 4713-4717.

y x 106

410 K 423 K 433 K

150

200

P (bar)

Cyclohexanol (C6H12O; MW=100.16)

[C-211]

106

410 K 423 K 433 K

y x 106

yx T (K) P (bar) 80000 410 145.9 18700 155.5 17500 172.3 37300 60000 190.6 54100 205.4 72500 423 129.9 14400 40000 153.8 22200 173.3 35500 20000 190.8 53900 204.3 70400 433 152.8 15400 0 164.6 23700 100 178.1 33500 191.8 50500 205.1 72400 Source: Mukhopadhyay, M.; Srinivas, P. Ind. Eng. Chem. Res. (1996), 35(12), 4713-4717.

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150

200 P (bar)

250

268

Solubility in Supercritical Carbon Dioxide

[C-212]

Cyclopentadienylmanganese tricarbonyl (C8H5MnO3; FW=204.06) Mx (mol/L)

16000

y1) x 106

2220 70 1 4470 90 5 7660 100 11 12200 110 19 120 21 12800 1: Calculated from M. Synonym: Tricarbonyl(η5cyclopentadienyl) manganese Source: Fedotov, A. N.;Simonov, A. P.; Popov, V. K.; Bagratashvili, V. N. J. Phys. Chem. B (1997),101(15), 29292932. 313

y x 106

T (K) P (bar)

102

8000

0 50

75

100 P (bar)

[C-213]

Cyclopentadienyl metal Complexes Name of compound Chloro(h5-cyclopentadienyl) dioxomolybdenum Dichlorobis(uh5-cyclopentadienyl) zirconium Carbonyldiiodo(h5cyclopentadienyl)cobalt

125

Formula

FW

C5H5ClMoO2

106

P (bar)

Mx (mol/L)

y1) x 106

313

128

1550

91.90

313

104

470

31.30

313

95

70

5.22

T (K)

228.48

C10H10Cl2Zr 292.32

C6H5CoI2O 405.85

1: Calculated from M. Source: Montilla, F.; Rosa, V.; Prevett, C.; Aviles, T.; Nunes da Ponte, M.; Masi, D.; Mealli, C. Dalton Trans. (2003), (11), 2170-2176.

[C-214]

Cyclopentadienyl trimethylsilyl metal Complexes Name of compound Chloro[h5(trimethylsilyl)cyclopentadienyl] dioxomolybdenum Dichlorobis[h5(trimethylsilyl)cyclopentadienyl] zirconium Carbonyldiiodo[h5-(trimethylsilyl) cyclopentadienyl]cobalt

Formula

FW

C8H13Cl22MoOSi

T (K)

P (bar)

313

102

313

103

313

99

106

Mx (mol/L)

y1) x 106

5810

393.65

1380

92.68

336.91

C16H26Cl2Si2Zr 434

C9H13CoI2OSi

4102

477.82

1: Calculated from M. Source: Montilla, F.; Rosa, V.; Prevett, C.; Aviles, T.; Nunes da Ponte, M.; Masi, D.; Mealli, C. Dalton Trans. (2003), (11), 2170-2176.

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8.71

Solubility Data C

269

Cyclotrimethylenetrinitramine (C3H6N6O6; MW=222.12) y1)

[C-215]

106

303 K 308 K 323 K 338 K 353 K

y x 106

x T (K) P (bar) W (g/kg) 303 69 0.002 0.40 104 0.007 1.39 60 138 0.013 2.58 276 0.032 6.34 414 0.053 10.50 483 0.055 10.90 308 104 0.008 1.59 40 138 0.013 2.58 276 0.034 6.74 414 0.067 13.27 483 0.064 12.68 323 104 0.003 0.59 20 138 0.013 2.58 276 0.051 10.10 414 0.097 19.22 483 0.111 21.99 338 104 0.001 0.20 138 0.009 0 1.78 276 0.076 15.06 0 414 0.173 34.28 483 0.173 34.28 353 138 0.004 0.79 276 0.114 22.59 414 0.237 46.96 50.32 483 0.254 1: Calculated from W. Synonyms: 1,3,5-Trinitrohexahydro-s-triazine; RDX Source: Morris, J. B. J. Chem. Eng. Data 43 (1998), 43(2), 269–273.

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200

400 P (bar)

600

270

Solubility in Supercritical Carbon Dioxide

Cyproterone acetate (C24H29ClO4; MW=416.94)

[C-216]

106

308 K 318 K 328 K 338 K 348 K

y x 106

yx T (K) P (bar) 308 122 45 152 63 182 81 213 108 243 135 274 155 304 176 355 253 318 122 35 300 152 54 182 72 213 94 243 116 274 141 304 165 200 355 261 328 122 23 152 38 182 52 213 75 100 243 97 274 125 304 158 355 250 338 122 17 152 25 0 182 36 100 213 59 243 83 274 112 304 145 355 255 348 122 13 152 18 182 23 213 42 243 63 274 93 304 134 355 245 Synonym: 6-Chloro-1,2α-methylene-6-dehydro-17αhydroxyprogesterone acetate Source: Asghari-Khiavi, M.; Yamini, Y.; Farajzadeh, M. A. J. Supercrit. Fluids (2004), 30(2), 111-117.

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200

300 P (bar)

400

4

Solubility Data D

[D-1]

DDT (C14H9Cl5; MW=354.49) y x 106 T (K) P (bar) 313 101 92 Synonym: 4,4'-Dichlorodiphenyltrichloroethane; 1,1,1-Trichloro-2,2-bis(4-chlorophenyl)ethane Source: Dooley, K. M.; Ghonasgi, D.; Knopf, F. C.; Gambrell, R. P. Environ. Progr. (1990), 9(4), 197-203.

[D-2]

Decalin (C10H18; MW=138.25) P (bar)

yx

323

60

800

343

70 80 90 100 55 75 90 100 110

1000 2700 6000 11100 2300 2900 5000 9200 11100

130 25900 Synonym: Decahydronaphthalene Source: Mukhopadhyay,M.; De, S. K. J. Chem. Eng. Data (1995), 40(4), 909-913.

30000 323K 343K

y x 106

T (K)

106

20000

10000

0 50

100

150

P (bar)

271

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272

Solubility in Supercritical Carbon Dioxide

[D-3]

Decane (C10H22; MW=142.28) 106

P (bar) y x 3000 645 10.0 459 19.0 2000 480 31.6 553 44.4 555 44.5 1000 550 44.6 766 56.7 0 1390 69.2 0 2010 74.8 2700 77.8 77.9 2710 Source: Chylinski, K. ; Gregorowicz, J. Fluid Phase Equil. (1998), 143(1-2), 163-172.

y x 106

T (K) 313

30 P (bar)

60

[D-4]

Decane (C10H22; MW=142.28) 80000 y x 106

T (K) P (bar) y x 106 344.15 89.9 3200 104.5 6000 118.5 15000 125.5 34000 127.0 43900 127.4 46200 127.6 64800 Source: Eustaquio-Rincon, R. ; Trejo, A. Fluid Phase Equil. (2001), 185(1-2), 231-239.

40000

0 80

Decane (C10H22; MW=142.28) T (K) 311

P (bar) 6.9 13.8 20.7 27.6 34.5 41.4 48.3 55.1 62.0 68.9 74.6 75.8 80.0 344.26 13.8 27.6 41.4 55.1 68.9 75.7 86.2

90

y x 106 1400 1000 900 800 700 700 700 700 700 700 700 800 5400 3900 2800 2500 2400 2400 2400 2800

CAT4240—CHAPTER 4—1/11/2006—19:27—SRIDHAR—XML MODEL C – pp. 271–334

100

120

140

P (bar) [D-5]

Solubility Data D

410.93

444.26

477.59

5800 17800 52300 10800 7400 6700 6200 6200 7700 6900 8800 12300 21100 36000 95400 32300 20300 17000 15200 15000 15000 15100 16900 19600 25200 36700 56400 129500 81800 48300 38300 34300 32800 32500 32600 34800 38600 45200 57300 78000 157000 176900 98300 74500 65400 62300 62000 62100 64700 70800 82300 102200

400000 310.93 K 344.26 K 377.59 K 410.93 K 444.26 K 477.59 K 510.93 K

300000 y x 106

377.59

103.4 120.6 128.2 13.8 27.6 41.4 55.1 68.9 77.2 86.2 103.4 120.6 137.9 155.1 164.9 13.8 27.6 41.4 55.1 68.9 78.9 86.2 103.4 120.6 137.9 155.1 172.3 185.6 13.8 27.6 41.4 55.1 68.9 80.9 86.2 103.4 120.6 137.9 155.1 172.3 188.3 13.8 27.6 41.4 55.1 68.9 82.9 86.2 103.4 120.6 137.9 155.1

273

200000

100000

0 05

CAT4240—CHAPTER 4—1/11/2006—19:27—SRIDHAR—XML MODEL C – pp. 271–334

0

100 P (bar)

150

200

274

Solubility in Supercritical Carbon Dioxide

172.3 145500 178.3 195000 510.93 13.8 345200 27.6 188400 41.4 142200 55.1 131600 68.9 127600 84.1 126000 86.2 126100 103.4 129400 120.6 139200 137.9 165300 153.3 272000 Source: Reamer, H. H.; Sage, B. H . J. Chem. Eng. Data (1963), 8(4), 508-513.

[D-6]

Decane (C10H22; MW=142.28) P (bar) 343.0 110.0 115.0 118.0 120.0 122.0 123.0 124.0 125.0 126.0 126.4 362.5 116.0 120.0 130.0 135.0 138.0 140.0 142.0 145.0 147.0 148.0 149.0 150.0 382.0 124.0 130.0 136.0 141.0 144.0 146.0 150.0 152.0 154.0 157.0 159.0 160.0 162.0

S (g/L) 10.50 15.61 20.39 23.30 28.91 32.85 38.10 45.14 58.06 65.18 9.60 11.47 18.02 23.54 27.38 32.18 35.11 43.92 53.97 62.46 70.29 80.76 12.37 15.42 18.64 22.87 24.97 27.77 31.68 35.54 38.03 45.01 49.54 53.84 61.07

x

106

10800 14700 18300 20200 24200 27000 30700 35600 44700 49600 11500 13000 18000 22100 24800 28400 30300 36500 43600 49600 55000 62100 15800 18500 20900 24400 25800 28100 30800 33900 35500 40800 44000 47200 52400

100000

75000 y x 106

T (K)

y1)

343.0 K 362.5 K 382.0 K 402.0 K

50000

25000

0 100

120

CAT4240—CHAPTER 4—1/11/2006—19:27—SRIDHAR—XML MODEL C – pp. 271–334

140 P (bar)

160

180

Solubility Data D

402.0

275

164.0 166.0 168.0 124.0 130.0 142.0

70.28 84.89 115.50 14.34 16.45 23.24

145.0 148.0 150.0 155.0 156.0 158.0 158.0 160.0 162.0 165.0 168.0 172.0 174.0 176.0

25.33 27.54 29.44 34.76 35.22 37.80 38.01 41.47 44.77 50.44 56.71 68.68 76.26 86.86

58900 69300 90600 20700 22400 28200

29900 31600 33200 37400 37600 39600 39800 42700 45200 49600 54200 63200 68800 76600

1: Calculated from S. Source: Swaid, I.; Nickel, D.; Schneider, G. M. Fluid Phase Equil. (1985), 21(1-2), 95-112.

[D-7]

1,10-Decanediol (C10H22O2; MW=174.28) 106

900

y x 106

P (bar) y x 205.3 299 253.7 358 307.1 395 323 138.2 189 154.5 260 185.5 362 224.4 448 263.7 543 305.9 617 328 133.7 199 164.7 397 195.8 524 222.8 599 262.8 704 307.3 789 Synonym: Decamethylene glycol Source: Pennisi, K. J.; Chimowitz, E. H. J. Chem. Eng. Data (1986), 31(3), 285-288. (See also Chimowitz, E. H.; Pennisi, K. J. AIChE J. (1986), 32(10), 1665-1676). T (K) 318

600

318 K 323 K 328 K

300

0 100

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200 P (bar)

300

276

Solubility in Supercritical Carbon Dioxide

[D-8]

1,10-Decanediol (1) + Benzoic acid (2) Mixture 308

318

P (bar) 119.4 125.5 131.9 163.8 186.4 230.9 265.1 306.4 119.4 125.0 132.9 163.8 186.8 226.1 267.6 307.1

x

106

127.0 142.0 153.0 181.4 236.0 254.2 288.2 306.4 125.0 163.0 203.0 341.1 348.6 410.7 412.5 533.5

y21)

x

106

1430 1610 1790 2338 2689 3246 3425 3874 1000 1350 1720 2755 3195 3843 4582 4840

6000

4000

Diol 308 K Diol 318 K Acid 308 K Acid 318 K

y x 106

T (K)

y11)

2000

0 100

200

300

P (bar)

1: Measured from the mixture of solids 1 and 2 of equal weights. Source: Chimowitz, E. H.; Pennisi, K. J. AIChEJ (1986), 32(10), 1665-1676. (See also Pennisi, K. J.; Chimowitz, E. H. J. Chem. Eng. Data (1986), 31(3), 285-288).

[D-9]

1-Decanol (C10H2O2; MW=158.28)

402.0

P (bar) 130 140 150 160 170 180 210 211 185 200 230 248

S (g/L) 4.9 9.7 16.6 26.1 38.9 54.1 136.8 141.5 16.2 23.7 55.7 121.2

y1) x 106 3360 5840 8900 13000 18100 23900 53000 54600 12900 17200 34000 66400

80000

y x 106

T (K) 343.3

343.3 K 402.0 K

40000

0 100

1: Calculated from S. Synonyms: Decyl alcohol; Capric alcohol Source: Nickel, D.; Schneider, G. M. J. Chem. Thermodyn. (1989), 21(3), 293-305.

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150

200 P (bar)

250

Solubility Data D

277

Decyl 2,5-dichlorobenzoate (C17H24Cl2O2; MW=331.28) P(bar) y x 88.5 2400 140.9 2400 184.8 2400 207.8 2400 184.8 7800 182.0 7800 203.9 7800 600 225.2 7800 276.5 7800 317.9 7800 349.6 14700 312.3 14700 400 298.3 14700 287.8 14700 286.8 14700 290.1 14700 299.7 14700 200 310.3 14700 326.4 14700 346.2 14700 574.5 24900 500.3 24900 423.4 24900 0 392.7 24900 250 368.1 24900 361.6 24900 353.7 24900 364.0 24900 370.8 24900 377.7 24900 241.3 18100 0 185.1 18100 0 181.3 18100 0 182.0 18100 0 184.4 18100 0 Source: Shen, Z.; McHugh, M. A.; Lott, K. M.; Wright, M. E. Fluid Phase Equil. (2004), 216(1), 1-12.

y=0.0024 y=0.0078 y=0.0147 y=0.0249 y=0.1810

P (bar)

T (K) 307.65 327.95 350.35 365.05 295.75 302.45 308.35 321.75 346.25 374.35 295.65 299.85 305.15 310.15 315.55 324.25 332.45 339.95 351.65 362.65 296.45 300.35 306.05 314.15 323.65 333.25 338.45 342.35 355.25 364.45 295.05 299.85 304.85 307.35 310.35

Diacetoxyscirpenol (C19H26O7; MW=366.41) T (K) P1) (bar) y2) x 106 334.68

[D-10]

106

87 95 101 102 106 110 112 115 116

0.02 0.07 0.32 0.91 2.30 4.90 11.00 16.00 22.00

CAT4240—CHAPTER 4—1/11/2006—19:27—SRIDHAR—XML MODEL C – pp. 271–334

300

350

400

T (K)

[D-11]

278

Solubility in Supercritical Carbon Dioxide

y x 106

121 39.00 900 123 38.00 126 65.00 129 92.00 133 180.00 600 137 190.00 139 305.00 144 310.00 149 470.00 300 154 600.00 159 650.00 167 710.00 880.00 176 0 1: Calculated from temperature and density digitized from the source graph. 50 2: Obtained by digitizing the graph in the original article. Synonyms: Anguidin; 12,13-Epoxytrichothec-9-ene3a,4b,15-triol 4,15-diacetate Source: Smith, R. D.; Udseth, H. R.; Wright, B. W.; Yonker, C. R. Sep. Sci. Technol. (1987), 22(2-3), 1065-1086.

100

150 P (bar)

[D-12]

Diamantane (C14H20; MW=188.31) P (bar) y x 81.3 101.4 126.2 151.2 175.5 201.0

106

800

29.5 56.9 175.0 369.0 553.0 708.0

y x 106

T (K) 333

Synonyms: Diadamantane; Decahydro 3,5,1,7-[1,2,3,4]butanetetrayl naphthalene Source: Smith, V. S.; Teja, A. S. J. Chem. Eng. Data (1996), 41(4), 923-925.

400

0 50

Diazepam (C16H13ClN2O; MW=284.74) T (K) 308

P (bar)

S (g/L)

122 152 182 213 243 274 304 334 355

0.88 1.07 1.31 1.39 1.77 1.82 1.99 2.30 2.40

200

yx

106

180 200 240 250 310 310 330 380 390

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100

150

200

P (bar)

[D-13]

Solubility Data D

328

338

348

122 152 182 213 243 274 304 334 355 122 152 182 213 243 274 304 334 355 122 152 182 213 243 274 304 334 355 122 152 182 213 243 274 304 334 355

0.68 1.05 1.36 1.66 1.87 2.34 2.71 3.17 3.35 0.54 0.84 1.27 1.61 2.11 2.63 2.94 3.79 4.04 0.42 0.75 1.16 1.76 2.31 3.03 3.78 4.48 4.95 0.39 0.62 1.11 1.66 2.38 3.19 4.04 4.99 5.82

160 220 260 310 340 410 470 540 560 160 200 270 320 410 490 530 670 710 160 210 270 380 470 600 720 830 900 180 200 290 390 520 670 810 970 1110

1200

800

308 K 318 K 328 K 338 K 348 K

y x 106

318

279

400

0 100

200

300

400

P (bar)

Synonym: 7-Chloro-1-methyl-5-phenyl-3H1,4-benzodiazepin-2(1H)-one Source: Yamini, Y.; Hassan, J.; Haghgo, S. J. Chem. Eng. Data (2001), 46(2), 451-455.

Dibenzo-24-crown-8 (C24H32O8; MW=448.51) T (K) P (bar) y x 106 308 121.6 18.6 162.1 17.8 202.7 21.1 243.2 28.9 283.7 34.4 324.2 36.2 364.8 37.4

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[D-14]

280

Solubility in Supercritical Carbon Dioxide

40.8 45.1 8.2 15.8 22.4 33.4 43.4 50.0 58.1 65.1 73.4 4.6 16.4 30.9 46.3 62.8 74.9 101.0 117.0 131.2 11.0 16.1 25.6 62.1 91.8 121.8 157.0 192.0 229.6

240

160

308 K 318 K 328 K 338 K

y x 106

405.3 445.8 318 121.6 162.1 202.7 243.2 283.7 324.2 364.8 405.3 445.8 328 121.6 162.1 202.7 243.2 283.7 324.2 364.8 405.3 445.8 338 121.6 162.1 202.7 243.2 283.7 324.2 364.8 405.3 445.8

80

0 100

300

500

P (bar)

Synonym: 6,7,9,10,12,13,20,21,23,24,26,27Dodecahydrodibenz[b,n][1,4,7,10,13,16,19,22]octa oxacyclotetracosin Source: Shamispur, M.; Yamini, Y.; Hasan, J. Fluid Phase Equil. (2001), 186(1-2), 39-46.

Dibenzo-27-crown-9 (C26H36O9; MW=492.56) T (K)

P (bar) y x

106

308

121.6 162.1 202.7 243.2 283.7 324.2 364.8 405.3 445.8 486.4 121.6 162.1 202.7

7.9 8.8 0.2 12.9 14.6 16.2 18.9 21.1 22.3 26.5 4.1 9.0 13.7

318

CAT4240—CHAPTER 4—1/11/2006—19:27—SRIDHAR—XML MODEL C – pp. 271–334

[D-15]

Solubility Data D

338

18.7 23.6 29.7 33.3 38.5 43.5 51.1 3.3 9.7 18.9 29.7 38.1 48.9 59.6 68.2 78.8 87.5 5.4 10.1 24.3 40.5 57.7 79.0 98.4 113.5

300

200 y x 106

328

243.2 283.7 324.2 364.8 405.3 445.8 486.4 121.6 162.1 202.7 243.2 283.7 324.2 364.8 405.3 445.8 486.4 121.6 162.1 202.7 243.2 283.7 324.2 364.8 405.3

281

308 K 318 K 328 K 338 K 348 K

100

0 100

300

500

P (bar)

445.8 134.7 486.4 153.2 348 121.6 1.8 162.1 7.4 202.7 28.5 243.2 57.5 283.7 93.0 324.2 148.0 364.8 160.9 405.3 202.7 445.8 243.0 486.4 275.7 Synonym: 6,7,9,10,12,13,15,16,23,24,26,27,29,30Tetradecahydrodibenzo[b,n][1,4,7,10,13,16,19,22,25] nonaoxacycloheptacosin Source: Shamispur, M.; Yamini, Y.; Hasan, J. Fluid Phase Equil. (2001), 186(1-2), 39-46.

Dibenzo-30-crown-10 (C28H40O10; MW=536.61) T (K) P (bar) y x 106 318 202.7 0.46 243.2 2.35 283.7 2.38 324.2 2.83 364.8 6.87 445.8 7.41

CAT4240—CHAPTER 4—1/11/2006—19:27—SRIDHAR—XML MODEL C – pp. 271–334

[D-16]

282

Solubility in Supercritical Carbon Dioxide

2.94 4.47 5.16 5.75 8.12 9.41 11.73 12.38 14.97 19.90 2.79 3.48 5.47 9.35 13.22 18.16 23.32 28.53 34.65 46.91 6.33 4.69 7.14 15.42 24.46 35.98 49.11 61.38 82.13 97.38

100 80

y x 106

328 121.6 162.1 202.7 243.2 283.7 324.2 364.8 405.3 445.8 486.4 3381 21.6 162.1 202.7 243.2 283.7 324.2 364.8 405.3 445.8 486.4 348 121.6 162.1 202.7 243.2 283.7 324.2 364.8 405.3 445.8 486.4

318 K 328 K 338 K 348 K

60 40 20 0 100

200

300

400

500

P (bar)

Synonym: 6,7,9,10,12,13,15,16,23,24,26,27,29,30,32,33Hexadecahydrodibenzo[b,q][1,4,7,10,13,16,19,22,25,28] decaoxacyclotriacontin Source: Shamispur, M.; Yamini, Y.; Hasan, J. Fluid Phase Equil. (2001), 186(1-2), 39-46.

Dibenzofuran (C12H8O; MW=168.19) T (K) 323

P (bar) 104.4 118.2 132.0 145.8 173.3 242.3 345.7 118.2 132.0 145.8

Cosolvent1) (mol %) Acetone 1.0 1.0 1.0 1.0 1.0 1.0 1.0 2.5 2.5 2.5

y x 106 2190 3480 3760 5610 12100 16900 33500 7850 11400 16600

CAT4240—CHAPTER 4—1/11/2006—19:27—SRIDHAR—XML MODEL C – pp. 271–334

[D-17]

Solubility Data D

283

2.5 20900 2.5 23200 2.5 26500 Methanol 323 94.1 1.0 258 118.2 1.0 2160 138.9 1.0 3150 173.3 1.0 9320 207.8 1.0 13500 276.7 1.0 27200 345.7 1.0 30200 104.4 2.5 4020 118.2 2.5 6290 145.8 2.5 9770 173.3 2.5 14000 242.3 2.5 17900 311.2 2.5 20500 1: Cosolvent in CO2 on a solute-free basis. Synonym: Diphenylene oxide Source: Van Alsten, J. G.; Eckert, C. A. J. Chem. Eng. Data (1993), 38(4), 605-610.

y x 106

173.3 242.3 345.7

40000

Acetone 1.0% Acetone 2.5% Methanol 1.0% Methanol 2.5%

30000

20000

10000

0 0

100

200

300

400

P (bar)

Dibenzothiophene (C12H8S; MW=184.26)

[D-18]

106

309.2 K 328.2 K 338.2 K

3000

2000

yx

106

T (K) P (bar) y x 309.15 76.9 28 104.4 486 138.9 974 173.4 1053 207.9 1250 242.3 1530 276.8 2295 328.15 76.9 19 104.4 151 138.9 917 173.4 1390 207.9 2120 242.3 2230 276.8 2340 338.15 76.9 22 104.4 84 138.9 625 173.4 1410 207.9 2200 242.3 2440 276.8 3220 Synonyms: 9-Thiafluorene; Diphenylene sulfide Source: Mitra, S.; Chen, J. W.; Viswanath, D. S. J. Chem. Eng. Data (1988), 33(1), 35-37.

1000

0 50

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150 P (bar)

250

284

Solubility in Supercritical Carbon Dioxide

[D-19]

Dibenzoylmethane (C15H12O2; MW=224.25) T (K)

P (bar)

S (g/L)

y x 106

101 2.7 730 152 5.4 1300 203 5.7 1280 253 7.8 1690 304 8.4 1760 355 10.5 2150 318 101 1.8 670 152 4.0 1050 203 6.6 1590 253 9.6 2190 355 17.7 3760 328 101 0.5 300 152 2.7 820 203 9.6 2470 253 15.7 3770 304 19.8 4530 355 27.4 6030 338 101 0.1 100 152 2.2 750 203 11.3 3180 253 22.2 5670 304 32.0 7650 355 43.5 9950 Synonyms: 1,3-Diphenyl-1,3-propanedione; 2-Benzoylacetophenone Source: Shamsipur, M.; Ghiasvand, A. R.; Yamini, Y. J. Chem. Eng. Data (2004), 49(5), 1483-1486.

y x 106

308

12000 308 K 318 K 328 K 338 K

9000

6000

3000

0 50

150

250

350

P (bar)

Di-tert-butyl 3H-naphtho[2,1-b]pyran-2,3-dicarboxylate (C23H52O6; MW=382.46) [D-20] T (K) 308

318

P (bar)

S (g/L)

122 152 182 213 243 274 304 334 355 122 152 182 213 243 274 304

6.02 7.89 9.00 9.74 11.64 11.94 13.12 14.01 14.40 3.64 5.18 8.41 10.12 11.94 15.42 17.95

y x 106 898 1108 1217 1277 1491 1498 1618 1700 1732 633 799 1220 1408 1609 2024 2307

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Solubility Data D

285

308 K 318 K 328 K 338 K 348 K

y x 106

334 19.60 2471 355 21.07 2630 328 122 1.48 330 152 1.98 347 182 6.54 1035 213 11.83 1761 243 14.58 2082 274 18.53 2558 12000 304 22.91 3080 334 26.10 3431 355 28.78 3731 3381 22 0.78 228 152 1.20 245 8000 182 5.47 962 213 12.23 1972 243 19.53 2971 274 24.24 3536 304 30.21 4262 4000 334 38.73 5315 355 44.01 5936 348 122 0.57 199 152 0.93 224 182 5.64 1108 0 213 8.83 1555 100 243 20.25 3307 274 30.40 4704 304 45.67 6760 334 59.95 8590 355 70.63 9919 Synonym: Di-tert-butyl 3H-benzo[f]chromene-2,3-dicarboxylate Source: Bahramifar, N.; Yamini, Y.; Ramazani, A.; Noshiranzadeh, N. J. Chem. Eng. Data (2003), 48(5), 1104-1108.

1,2-Dichlorobenzene (C6H4Cl2; MW=147.00) T (K) 313.2

353.2

P (bar) y x 106 62.9 1300 62.9 1600 65.9 600 65.9 700 70.9 210 75.9 1900 62.9 2900 62.9 3000 80.9 4000 100.9 5100 100.9 5300 120.9 8900 140.9 18600 140.9 18000 160.9 54000

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200

300

400

P (bar)

[D-21]

286

Solubility in Supercritical Carbon Dioxide

60000 62.9 8000 62.9 8000 80.9 8400 40000 100.9 10300 120.9 12200 120.9 12200 120.9 12700 140.9 13800 20000 140.9 14500 140.9 14300 160.9 17500 180.9 30200 0 180.9 30300 50 Source: Walther, D.; Maurer, G. Ber. Bunsenges. Phys. Chem. (1992), 96(8), 981-988.

313.2 K 353.2 K 393.2 K

y x 106

393.2

100

150 P (bar)

2,2'-Dichlorobiphenyl (C12H8Cl2; MW=223.10) y x 106 901 1300 1700 2000 2320 2600 2920 3180 3320 3610 3890 4210 4500 4970 5160 5610 228 569 1070 1620 2130 2590 3030 3410 3980 4180 4570 5240 5940 6750 7280 7860

[D-22]

12000 313 K 323 K 333 K

8000 y x 106

T (K) P (bar) 313 100 110 120 130 140 150 160 170 180 190 200 220 240 260 280 300 323 100 110 120 130 140 150 160 170 180 190 200 220 240 260 280 300

200

4000

0 50

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150

250 P (bar)

350

Solubility Data D

333

287

100 110 120 130 140 150 160 170 180 190 200 220 240 260 280 300

173 303 597 1000 1520 2170 2830 3460 4000 4610 5290 6380 7380 8610 9470 10600

Synonym: 2,2'-Dichloro-1,1'-biphenyl Source: Anitescu, G.; Tavlarides, L. L. J. Supercrit. Fluids (1999), 14(3), 197-211.

2,2'-Dichlorobiphenyl (C12H8Cl2; MW=223.10) P (bar)

313

100 110 120 130 140 150 160 170 180 190 200 220 240 260 280 300 100 110 120 130 140 150 160 170 180 190

323

n-Butane1) (mol%) 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0

y x 106 1300 1860 2400 2790 3190 3440 3820 4100 4320 4560 4810 5190 5580 5990 6330 6680 337 825 1520 2250 2920 3500 4030 4470 4980 5310

12000

y x 106

T (K)

[D-23]

313 K 323 K 333 K

8000

4000

0 50

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150

250 P (bar)

350

288

Solubility in Supercritical Carbon Dioxide

200 5.0 5710 220 5.0 6450 240 5.0 7190 260 5.0 7980 280 5.0 8590 300 5.0 9200 333 100 5.0 272 110 5.0 461 120 5.0 890 130 5.0 1460 140 5.0 2170 150 5.0 3040 160 5.0 3880 170 5.0 4640 180 5.0 5240 190 5.0 5900 200 5.0 6610 220 5.0 7780 240 5.0 8930 260 5.0 10100 280 5.0 11200 300 5.0 12100 1: Cosolventin CO2. Synonym: 2,2'-Dichloro-1,1'-biphenyl Source: Anitescu, G.; Tavlarides, L. L. J. Supercrit. Fluids (1999), 14(3), 197-211.

2,2'-Dichlorobiphenyl (C12H8Cl2; MW=223.10) T (K)

P (bar)

313

100 110 120 130 140 150 160 170 180 190 200 220 240 260 280 300 100 110 120 130

323

Methanol1) (mol%) 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0

y x 106 1220 1730 2230 2590 2940 3180 3520 3770 3980 4190 4410 4760 5100 5500 5790 6110 317 779 1450 2180

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[D-24]

Solubility Data D

289

y X 106

140 5.0 2800 150 5.0 3380 160 5.0 3900 170 5.0 4310 180 5.0 4760 190 5.0 5140 200 5.0 5530 12000 220 5.0 6450 313 K 240 5.0 6950 323 K 260 5.0 7670 333 K 280 5.0 8290 300 5.0 8880 8000 333 100 5.0 258 110 5.0 446 120 5.0 866 130 5.0 1420 140 5.0 2100 4000 150 5.0 2950 160 5.0 3780 170 5.0 4510 180 5.0 5090 190 5.0 5720 0 6410 200 5.0 50 150 250 220 5.0 7780 P(bar) 240 5.0 8930 260 5.0 10100 280 5.0 11200 300 5.0 12100 1: Cosolventin CO2. Synonym: 2,2'-Dichloro-1,1'-biphenyl Source: Anitescu, G.; Tavlarides, L. L. J. Supercrit.Fluids (1999), 14(3), 197-211.

4,4'-Dichlorobiphenyl (C12H8Cl2; MW=223.10) T (K) 313

P (bar) y x 106 100 227 110 293 120 345 130 383 140 418 150 447 160 477 170 498 180 509 190 531 200 553 220 569 240 583 260 613 280 616 300 639

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350

[D-25]

290

Solubility in Supercritical Carbon Dioxide

323

313 K 323 K 333 K

y x 106

100 97 110 191 120 299 130 399 140 481 150 547 160 609 170 659 180 729 190 749 200 790 1500 220 853 240 912 260 974 280 1010 1000 300 1040 333 100 96 110 138 120 226 500 130 332 140 460 150 586 160 704 170 810 0 180 887 50 190 974 200 1060 220 1190 240 1290 260 1410 280 1480 300 1580 Synonyms: 4,4'-Dichloro-1,1'-biphenyl; PCB 15 Source: Anitescu, G.; Tavlarides, L. L. J. Supercrit. Fluids (1999), 14(3), 197-211.

4,4'-Dichlorobiphenyl (C12H8Cl2; MW=223.10) T (K) P (bar) 313.1 98.9 113.5 124.2 133.1 191.4 218.7 243.0 320.6 380.3

y x 106 178 259 436 389 549 637 658 782 870

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150

250

350

P (bar)

[D-26]

Solubility Data D

283 344 605 624 884 1137 1257 1244

1500

313.1 K 323.1 K

1000 y x 106

323.1 113.8 126.3 158.6 162.3 206.3 269.3 364.9 376.2

291

Synonyms: 4,4'-Dichloro-1,1'-biphenyl; PCB 15 Source: Yu, E.; Richter, M.; Chen, P.; Wang, X.; Tavlarides, L. L. Ind. Eng. Chem. Res. (1995), 34(1), 340-346.

500

0 50

150

250

350

P (bar)

4,4'-Dichlorobiphenyl (C12H8Cl2; MW=223.10)

313

323

P (bar) 100 110 120 130 140 150 160 170 180 190 200 220 240 260 280 300 100 110 120 130 140 150 160 170 180 190 200 220 240

(mol%) 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0

[D-27]

y x 106 335 411 477 522 562 593 611 637 650 666 678 699 713 726 740 755 161 284 423 539 636 720 788 842 895 927 957 1020 1080

2000 313 K 323 K 333 K

1500 y x 106

T (K)

n-Butane1)

1000

500

0 50

CAT4240—CHAPTER 4—1/11/2006—19:27—SRIDHAR—XML MODEL C – pp. 271–334

150

250 P (bar)

350

292

Solubility in Supercritical Carbon Dioxide

260 5.0 1130 280 5.0 1170 300 5.0 1210 333 100 5.0 143 110 5.0 221 120 5.0 348 130 5.0 494 140 5.0 668 150 5.0 826 160 5.0 969 170 5.0 1080 180 5.0 1160 190 5.0 1240 200 5.0 1320 220 5.0 1430 240 5.0 1540 260 5.0 1630 280 5.0 1700 300 5.0 1750 1: Cosolvent in CO2. Synonyms: 4,4'-Dichloro-1,1'-biphenyl; PCB 15 Source: Anitescu, G.; Tavlarides, L. L. J. Supercrit. Fluids (1999), 14(3), 197-211.

4,4'-Dichlorobiphenyl (C12H8Cl2; MW=223.10) T (K) 313

323

P (bar) 100 110 120 130 140 150 160 170 180 190 200 220 240 260 280 300 100 110 120 130 140 150

Methanol1) (mol%) 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0

y x 106 292 370 431 471 506 531 559 578 596 610 624 641 652 666 677 691 149 2 262 402 527 623 699

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[D-28]

Solubility Data D

293

313 K 323 K 333 K

y x 106

160 5.0 764 170 5.0 816 180 5.0 861 190 5.0 896 200 5.0 935 220 5.0 1000 2000 240 5.0 1060 260 5.0 1110 280 5.0 1150 300 5.0 1180 1500 333 100 5.0 132 110 5.0 206 120 5.0 330 130 5.0 473 1000 140 5.0 641 150 5.0 794 160 5.0 921 170 5.0 1020 500 180 5.0 1100 190 5.0 1180 200 5.0 1240 0 220 5.0 1360 240 5.0 1470 50 260 5.0 1560 280 5.0 1640 300 5.0 1710 1: Cosolvent in CO2. Synonyms: 4,4'-Dichloro-1,1'-biphenyl; PCB 15 Source: Anitescu, G.; Tavlarides, L. L. J. Supercrit. Fluids (1999), 14(3), 197-211.

150

250

350

P (bar)

Dichlorobis(triphenylphosphine)nickel(II) (C36H30Cl2NiP2; FW=654.20)

[D-29]

6

6

4

308 K 318 K 328 K

yx

106

y x 10 T (K) P (bar) 308 108 1.32 140 1.75 194 2.10 222 2.19 249 2.11 277 2.41 318 137 1.68 165 2.47 182 3.02 222 3.64 249 3.73 279 4.41 328 138 1.69 167 3.13 195 3.93 219 4.42 249 4.82 276 5.33 Source: Palo, D. R.; Erkey, C. J. Chem. Eng. Data (1998), 43(1), 47-48.

2

0 100

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200 P (bar)

300

294

Solubility in Supercritical Carbon Dioxide

2,4-Dichloro-1-naphthol (C10H6Cl2O; MW=213.06)

[D-30]

106

308.15 K 318.15 K 328.15 K

y x 106

yx T (K) P (bar) 308.15 100 178.8 115 232.7 130 341.0 1500 150 687.6 200 689.0 250 694.5 300 695.8 350 695.9 1000 318.15 100 143.5 115 181.4 130 297.9 150 762.3 200 870.5 500 250 868.1 300 896.6 350 973.6 328.15 100 80.0 0 115 160.0 130 430.7 0 150 875.7 200 959.3 250 1028.0 300 1152.0 350 1461.0 Synonym: 2,4-Dichloro-1-naphthalenol Source: Yoon, J. H.; Lee, H. S.; Lee, H. J. Chem. Thermodyn. (1993), 25(2), 193-196.

100

200

yx

20840 33840 46520 45930 61720 69740 85970 108100

Source: Van Leer, R. A.; Paulaitis, M. E. J. Chem. Eng. Data (1980), 25(3), 257-259.

[D-31]

120000 y x 106

T (K) P (bar) 309.15 80.3 86.2 112.6 125.7 150.1 162.1 171.0 206.2

400

P (bar)

2,4-Dichlorophenol (C6H4Cl2O; MW=163.00) 106

300

60000

0 50

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150 P (bar)

250

Solubility Data D

295

2,4-Dichlorophenoxyacetic acid (C8H6Cl2O3; MW=221.04)

y x 106

T1) (K) P2) (bar) y1,3) x 106 140 294 72 1.1 303 113 3.1 314 170 16.0 70 323 211 34.1 334 267 98.0 345 322 126.0 1: Obtained by digitizing the graph in 0 the original article. May have large 0 reading error as the original graph is small. 2: Calculated from temperature and density in the source graph. 3: Measured at a constant density (0.80 g/mL). Synonyms: 2,4-D; 2,4-Dichlorophenoxyethanoic acid Source: Burk, R.; Kruus, P. Can. J. Chem. Eng. (1992), 70(2), 1403-1407.

[D-32]

100

200 P (bar)

2,4-Dichlorophenoxyacetic acid (C8H6Cl2O3; MW=221.04) 106

x T (K) P (bar) 307.95 141 106 167 120 203 127 226 128 254 133 1: Obtained by digitizing the graph in the original article. Synonyms: 2,4-D; 2,4Dichlorophenoxyethanoic acid Source: Curren, M. S.; Burk, R. C. J.Chem. Eng. Data (1997), 42(4), 727-730.

120 100 100

2,4-Dichlorophenoxyacetic acid (C8H6Cl2O3; MW=221.04) T (K) P (bar) 313 250 300 350 400 450

yx

[D-33]

140 y x 106

y1)

300

106 10 11 33 57 83

CAT4240—CHAPTER 4—1/11/2006—19:28—SRIDHAR—XML MODEL C – pp. 271–334

200

300

P (bar)

[D-34]

296

Solubility in Supercritical Carbon Dioxide

200 250 300 350 400 450 150 200 250 300 350 400

393

10 113 291 497 694 843 10 33 554 1450 2910 4370

313 K 373 K 393 K

4500

y x 106

373

3000

1500

Synonyms: 2,4-D; 2,4-Dichlorophenoxyethanoic acid Source: Miller, D. J.; Hawthrone, S. B.; Clifford, A. A. J. Supercrit. Fluids (1997), 10(1), 57-63.

0 100

300

2,4-Dichlorophenoxyacetic acid (C8H6Cl2O3; MW=221.04)

333.1

313.1

323.1

0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 saturated saturated saturated saturated saturated saturated saturated saturated saturated saturated

y2)

x

[D-35]

106

18.2 29.4 36.9 42.9 50.9 58.5 27.0 42.5 53.5 66.3 80.6 16.4 40.4 61.7 84.3 112.0 45.4 62.9 79.0 93.6 109.0 44.3 75.5 101.0 129.0 146.0

250 200

yx

323.1

(bar) 104 125 146 167 187 208 125 146 167 187 208 125 146 167 187 208 125 146 167 187 208 125 146 167 187 208

Water1)

106

T (K) 313.1

P1)

500

P (bar)

150

CO2 313.1 K CO2 323.1 K CO2 333.1 K Water 313.1 K Water 323.1 K Water 333.1 K

100 50 0 100

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150 P (bar)

200

Solubility Data D

333.1

297

125 146 167 187 208

28.9 saturated 65.2 saturated 113.0 saturated 165.0 saturated 204.0 saturated 1: Cosolvent in CO2. 2: Obtained by digitizing the graph in the original article. Synonyms: 2,4-D; 2,4-Dichlorophenoxyethanoic acid Source: Macnaughton, S. J.; Foster, N. R. Ind. Eng. Chem. Res. (1994), 33(11), 2757-2763.

Diclofenac sodium (C14H11Cl2NO2· Na; FW=318.13) T (K) P1) (bar) y1) x 106 Anhydrate 313.15 101 1.3 200 2.5 301 6.2 Hydrate (C14H10Cl2NNaO2. 4H2O)

y x 106

12

313.15

100 1.6 201 5.0 300 9.0 1:Obtained by digitizing the graph in the original article. Synonyms: Diclofenac sodium salt; Sodium 2-(2,6-dichloroanilino)phenyl Source: Bettini, R.; Bertolini, G.; Frigo, E.; Rossi, A.; Casini, I.; Pasquali, I.; Giordano, F. J. Therm. Anal. Cal. (2004), 77(2), 625-638.

[D-36] Anhydrate Hydrate

8 4 0 50

150

250 P (bar)

Di-n -dodecylamine (C24H51N; MW=353.67) 106

[D-37] 300

y x 106

yx T (K) P (bar) 310 109.5 100 140.0 134 205.0 233 320 109.5 44 140.0 134 205.0 266 Synonyms: Didodecylamine; Dilaurylamine Source: Schmitt, W. J.; Reid, R. C. Chem. Eng. Comm. (1988), 64, 155-176.

350

310 K 320 K

150

0 100

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140

180 P (bar)

220

298

Solubility in Supercritical Carbon Dioxide

Didodecylphosphine (C24H51P; MW=370.64) 106

1500 y x 106

yx T (K) P (bar) 320 127 785 151 1210 Synonym: Dilaurylphosphine Source: Schmitt, W. J.; Reid, R. C. Chem. Eng. Comm. (1988), 64, 155-176.

[D-38]

1000 500 120

140

160

P (bar)

Didodecylthioether (C24H50S; MW=370.72)

[D-39] 3000

y x 106

y x 106 T (K) P (bar) 310 110.0 750 140.5 1560 201.0 2600 320 110.0 230 140.5 1040 201.0 2400 Synonym: Didodecylsulfane Source: Schmitt, W. J.; Reid, R. C. Chem. Eng. Comm. (1988), 64, 155-176.

310 K 320 K

1500

0 100

140

180

220

P (bar)

Diethylammonium diethyldithiocarbamate (C5H11NS2 · C4H11N; FW=222.41)

308.2

P (bar) 100

150

200

250

300

313.2

100

(mol%)

1 3 5 1 3 5 1 3 5 1 3 5 1 3 5 1 3 5

[D-40]

y x 106 1000 1210 1450 2230 2440 2760 3410 3600 3820 4310 4460 4780 4550 4790 5100 3620 3650 3770

12000

8000

1 mol% 3 mol% 5 mol%

y x 106

T (K)

Ethanol1)

4000 P = 200 bar

0 305

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310

315 T (K)

320

325

Solubility Data D

250

300

318.2

100

150 200

250

300

323.2

100

150

200

250

300

4700 4900 5330 6020 6250 6530 6510 6620 7030 7400 7520 7910 5400 5980 6330 7110 7530 7760 8010 8250 8570 8420 8730 9060 8850 9120 9570 6600 7230 7650 8710 9020 9360 9480 9740 10100 10000 10200 10730 10600 11100 11600

10000 1 mol% 3 mol% 5 mol%

y x 106

200

1 3 5 1 3 5 1 3 5 1 3 5 1 3 5 1 3 5 1 3 5 1 3 5 1 3 5 1 3 5 1 3 5 1 3 5 1 3 5 1 3 5

6000

T = 313.2 K

2000 0

100

200

300

400

P (bar)

9000

6000 y x 106

150

299

3000

100 bar 150 bar 200 bar 250 bar 300 bar

0 0

1: Cosolvent in CO2. Synonyms: Diethylamine diethyldithiocarbamate; N,N-Diethyldithiocarbamic acid diethylamine salt Source: Wang, T.; Wang, H. Chem. Eng. Process. (2003), 42(1), 61-65.

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2

T = 313.2 K

4

Ethanol (mol %)

6

300

Solubility in Supercritical Carbon Dioxide

Di-(2-ethylhexyl)phosphoric acid (C16H35O4P; MW=322.42) 106

T (K) P (bar) M (mol/L) 1600 333 150 0.02 9600 200 0.16 250 0.81 43000 1: Calculated from M. Synonym: Bis(2-ethylhexyl) phosphate Source: Meguro, Y.; Iso, S.; Sasaki, T.; Yoshida, Z. Anal. Chem. (1998), 70(4), . 774-779

[D-41]

50000 y x 106

y1) x

25000

0 100

200 P (bar)

Diethyl phthalate (C12H14O4; MW=222.24)

[D-42]

106

10000 318.15 K 328.15 K

y x 106

yx T (K) P (bar) 318.15 85.8 100 96.0 1000 115.3 7400 328.15 56.2 100 70.3 500 82.7 600 101.0 700 111.0 1000 125.6 2200 Synonyms: Phthalic acid diethyl ester; Diethyl 1,2-benzenedicarboxylate Source: Cheng, K.-W.; Kuo, S.-J.; Tang, M.; Chen, Y.-P. J. Supercrit. Fluids (2000), 18(2), 87-99.

300

5000

0 50

100

150

P (bar)

Dihexyl-(N ,N -diethylcarbamoyl)methylphosphonate (C18H38NO4P; MW=363.47) [D-43] 30000 y x 106

T (K) P (bar) M (mol/L) y1) x 106 35 333 100 0.0002 120 110 0.0010 7900 120 0.0780 150 0.4100 29000 1: Calculated from M. Synonym: Dihexyl(diethylcarbamoyl) methylphosphonate Source: Meguro, Y.; Iso, S.; Sasaki, T.; Yoshida, Z. Anal. Chem. (1998), 70(4), 774-779.

15000 0 80

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120 P (bar)

160

Solubility Data D

301

1,4-Dihydroxyanthraquinone (C14H8O4; MW=240.21)

[D-44]

6

308 K 318 K 328 K 338 K 348 K

y x 10

6

y x 10 T (K) P (bar) S (g/L) 40 308 121.6 0.17 54 162.1 0.24 61 202.7 0.29 75 243.2 0.37 79 283.7 0.40 90 324.2 0.47 104 364.8 0.54 111 405.3 0.59 24 318 121.6 0.08 46 162.1 0.19 300 64 202.7 0.29 83 243.2 0.39 101 283.7 0.48 120 324.2 0.59 130 364.8 0.65 200 144 405.3 0.75 45 328 162.1 0.17 74 202.7 0.30 103 243.2 0.45 100 130 283.7 0.60 324.2 0.71 151 364.8 0.83 172 187 405.3 0.93 0 16 338 121.6 0.03 100 50 162.1 0.16 87 202.7 0.33 127 243.2 0.52 158 283.7 0.69 189 324.2 0.85 220 364.8 1.02 249 405.3 1.19 13 348 121.6 0.02 36 162.1 0.10 82 202.7 0.28 135 243.2 0.52 180 283.7 0.74 222 324.2 0.95 266 364.8 1.19 405.3 1.44 314 Synonyms: C. I. Solvent Orange 86; Quinizarin Source: Fat'hi, M. R.; Yamini, Y.; Sharghi, H.; Shamsipur, M. J. Chem. Eng. Data (1998), 43(3), 400-402.

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200

300 P (bar)

400

302

Solubility in Supercritical Carbon Dioxide

1,4-Dihydroxyanthraquinone (C14H8O4; MW=240.21)

[D-45]

6

y x 10 T (K) P (bar) 120 353.2 160 12.6 190 27.5 210 52.6 240 67.2 80 270 79.2 300 110.0 373.2 120 2.2 40 140 7.2 160 13.2 220 60.8 250 107.0 0 393.2 120 0.7 100 150 9.6 180 21.0 210 69.4 Synonyms: C. I. Solvent Orange 86; Quinizarin Source: Ferri, A.; Banchero, M.; Manna, L.; Sicardi, S. J. Supercrit. Fluids (2004), 30(1), 41-49.

y x 10

6

353.2 K 373.2 K 393.2 K

200

300

P (bar)

1,8-Dihydroxyanthraquinone (C14H8O4; MW=240.21) S (g/m ) 9 12 20 24 27 29 32 8 13 21 26 31 37 42 6 15 23 28 40 49 54 4 18 31 45

1)

y x 10

[D-46]

6

2.2 3.0 4.1 4.9 5.4 5.6 6.2 2.0 3.1 4.7 5.5 6.4 7.5 8.3 2.1 3.9 5.6 6.3 8.8 10.3 11.2 1.9 5.4 8.3 10.8

20

15 y x 106

T (K) P (bar) 308.15 122 162 203 243 284 324 365 318.15 122 162 203 243 284 324 365 328.15 122 162 203 243 284 324 365 338.15 122 162 203 243

3

308 K 318 K 328 K 338 K 348 K

10

5

0 100

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200

300 P (bar)

400

Solubility Data D

348.15

284 324 365 122 162 203 243 284 324 365

303

50 57 71 2 15 32 49 57 71 90

11.8 12.6 15.4 1.4 5.4 9.3 12.8 14.0 16.5 20.2

1: The magnitude " x 104 " of y in the original table must have been misprinted and thus was corrected to " x 105" based on S. Synonym: Danthron Source: Fat'hi, M. R.; Yamini, Y.; Sharghi, H.; Shamsipur, M. Talanta (1999), 48(4), 951-957.

1,8-Dihydroxyanthraquinone (C14H8O4; MW=240.21)

[D-47]

106

150

327 K 337 K 357 K

100 y x 106

yx T (K) P (bar) 327 110 8.2 115 15.8 116 15.4 119 16.5 126 21.2 136 27.5 139 28.9 152 41.0 165 53.1 178 58.6 180 65.9 188 69.4 200 82.4 337 115 7.9 122 21.5 141 44.0 152 60.8 174 73.3 180 78.8 201 98.9 357 69 7.3 72 18.3 74 29.3 80 64.1 100 95.2 128 147.0 Synonym: Danthron Source: Galia, A.; Argentino, A.; Scialdone, O.; Filardo, G. J. Supercrit. Fluids (2002), 24(1), 7-17.

50

0 50

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100

150 P (bar)

200

304

Solubility in Supercritical Carbon Dioxide

1,8-Dihydroxyanthraquinone (C14H8O4; MW=240.21)

[D-48]

S1)

y x 106

60 1) y3) x 106 T (K) P (bar) (mg/Nl2)) 313.15 72 0.0028 0.26 96 0.0477 4.42 119 0.0953 8.83 30 161 0.1837 17.03 213 0.2698 25.00 284 0.3674 34.05 0 527 0.6059 56.15 1: Obtained by digitizing the graph in 0 the original article. 2: "Nl" means "Normliter," which designates one liter at 273.15 K and 1 atm. 3: Calculated from S. Synonyms: Danthron Source: Stahl, E. Rev. Latinoam. Quim. (1980), 11(1), 1-7.

200

400 P (bar)

[D-49]

1,8-Dihydroxyanthrone (C14H10O3; MW=226.23) S (g/L) 0.49 0.32 0.40 0.51 0.58 0.66 0.72 0.79 0.89 0.92 1.00 0.12 0.25 0.36 0.49 0.59 0.71 0.81 0.90 1.01 1.10 1.24 0.06 0.16 0.30 0.45 0.58 0.71 0.82

yx

106 133 81 96 118 130 144 154 168 186 190 204 47 72 95 121 141 165 183 201 219 236 261 32 55 89 123 149 175 196

308 K 318 K 328 K 338 K 348 K

450

y x 106

T (K) P (bar) 308 101 127 152 177 203 228 253 279 304 329 355 318 101 127 152 177 203 228 253 279 304 329 355 328 101 127 152 177 203 228 253

600

300

150

0 50

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150

250 P (bar)

350

Solubility Data D

305

279 0.92 215 304 1.04 237 329 1.17 261 355 1.29 283 338 101 0.04 31 127 0.10 46 152 0.27 92 177 0.43 130 203 0.63 177 228 0.86 227 253 1.08 273 279 1.29 318 304 1.48 354 329 1.66 389 355 1.89 433 348 101 0.05 39 127 0.06 37 152 0.16 64 177 0.35 119 203 0.52 160 228 0.76 217 253 1.10 299 279 1.39 362 304 1.68 424 329 1.98 487 Synonyms: 1,8-Dihydroxyanthracen-9(10H)-one; 1,8-Dihydroxy-9-anthrone Source: Karami, A. R.; Yamini, Y.; Ghiasvand, A. R.; Sharghi, H.; Shamsipur, M. J. Chem. Eng. Data (2001), 46(6), 1371-1374.

[D-50]

Dihydroxybenzenes (C6H6O2; MW=110.11) Compounds

Synonyms

o -Dihydroxybenzene m -Dihydroxybenzene p -Dihydroxybenzene

T (K)

P(bar) 310 310

yx 106

1,2-Benzenediol; Pyrocatechol 328 1,3-Benzenediol; Resorcinol 328 1,4-Benzenediol; Hydroquinone 328 310 Source: Krukonis, V. J.; Kurnik, R. T. J. Chem. Eng. Data (1985), 30(3), 247-249.

1800

1,8-Dihydroxy-2,7-bis (prop-1 -enyl)anthraquinone (C20H16O4; MW=320.34)

[D-51]

T (K) P (bar) 308.15 122 162 203 284 324 365 405

3

S (g/m ) 29 47 132 243 381 547 676

1)

y x 10

6

5.2 7.8 20.9 36.2 55.6 78.3 95.2

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485 21

306

Solubility in Supercritical Carbon Dioxide

318.15

200 308 K 318 K 328 K 338 K 348 K

150

y x 10

6

162 26 4.7 203 122 20.5 243 266 42.8 284 426 66.4 324 554 84.1 365 700 103.9 328.15 162 90 17.9 203 207 37.4 243 410 69.9 284 492 80.5 324 609 96.4 365 752 116.0 405 779 117.5 338.15 122 90 31.1 162 194 44.2 203 303 59.6 243 448 81.4 284 570 98.3 324 681 112.9 365 761 122.2 405 785 122.8 348.15 122 300 125.6 162 440 116.7 203 558 120.8 284 766 139.8 324 862 150.0 365 967 162.1 405 1109 180.4 1: The y values in the source table did not agree with S and thus were re-calculated based on S. Source: Fat'hi, M. R.; Yamini, Y.; Sharghi, H.; Shamsipur, M. Talanta (1999), 48(4), 951-957.

100

50

0 100

200

300 P (bar)

[D-52]

7,8-Dihydroxyflavone (C15H10O4; MW=254.24) 308.2 K 318.2 K

40 yx

106

y x 106 T (K) P (bar) 308.2 91 8.6 101 12.1 152 15.1 203 18.0 253 18.7 318.2 101 16.0 152 32.1 203 36.0 253 38.8 Synonym: 7,8-Dihydroxy-2-phenyl-4-benzopyrone Source: Matsuyama, K.; Mishima, K.; Ohdate, R.; Chidori, M.; Yang, H. J. Chem. Eng. Data (2003), 48(4), 1040-1043.

400

20

0 50

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150 P (bar)

250

Solubility Data D

307

[D-53]

1,4-Dihydroxy-3-methylthioxanthone (C14H10O3S; MW=258.29) 0.016 0.019 0.035 0.041 0.047 0.052 0.062 0.067 0.016 0.023 0.043 0.049 0.060 0.070 0.023 0.076 0.083 0.022 0.040 0.050 0.070 0.096 0.117 0.122 0.142 0.009 0.031 0.063 0.091 0.121 0.147 0.156 0.183 0.014 0.042 0.082 0.079 0.126 0.149 0.184 0.205

y x 10

3.5 3.9 6.7 7.9 8.7 9.4 11.2 12.0 4.2 5.3 9.3 10.1 11.9 13.6 14.4 14.2 15.5 5.7 9.5 11.0 14.8 19.7 23.3 23.8 27.4 2.8 8.1 15.1 20.7 26.3 30.8 31.9 36.7 5.0 12.3 21.4 19.2 28.9 32.9 39.3 43.1

50 40

6

S (g/L)

y x 10

T (K) P (bar) 308 121 152 212 243 273 304 334 354 318 121 152 182 212 243 273 304 334 354 328 152 182 212 243 273 304 334 354 338 152 182 212 243 273 304 334 354 348 152 182 212 243 273 304 334 354

6

308 K 318 K 328 K 338 K 348 K

30 20 10

100

Synonym: 1,4-Dihydroxy-3-methyl-9H-thioxanthen-9-one Source: Shamsipur, M .; Karami, A.R.; Yamini, Y.; Sharghi, H.; Salimi, A. R. J. Chem. Eng. Data (2003), 48(5), 1088-1091.

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200

300 P (bar)

400

308

Solubility in Supercritical Carbon Dioxide

1,8- Dihydroxy-2-(prop-2'-enyl)anthrone (C17H14O3; MW=266.30) 308

318

328

338

348

P (bar) 101 127 152 177 203 228 253 279 304 329 355 101 127 152 177 203 228 253 304 329 355 101 127 152 177 203 228 253 279 304 329 355 101 127 152 177 203 228 253 279 304 329 355 101 127 152 177

S (g/L) 0.44 0.78 1.02 1.28 1.50 1.81 2.01 2.14 2.45 2.92 3.34 0.21 0.36 0.59 0.82 1.01 1.33 1.61 2.30 2.56 3.19 0.06 0.16 0.41 0.70 1.05 1.39 1.77 1.94 2.63 3.10 4.06 0.05 0.08 0.27 0.58 1.06 1.52 1.93 2.56 3.25 4.00 4.65 0.07 0.06 0.17 0.42

yx

106 171 215 259 296 350 383 400 452 532 599 69 90 135 180 212 271 321 443 484 594 31 50 107 168 238 304 372 397 528 613 787 34 34 84 155 262 355 433 556 686 825 940 50 33 62 128

1200 308 K 318 K 328 K 338 K 348 K

900

y x 106

T (K)

[D-54]

106

600

300

0 50

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150

250 P (bar)

350

Solubility Data D

309

203 0.80 215 228 1.33 337 253 1.88 451 279 2.82 651 304 3.83 851 329 4.91 1064 Synonym: 1,8- Dihydroxy-2-(prop-2'-enyl)anthracen-9-one Source: Karami, A. R.; Yamini, Y.; Ghiasvand, A. R.; Sharghi, H.; Shamsipur, M. J. Chem. Eng. Data (2001), 46(6), 1371-1374.

1,6-Dihydroxyxanthone (C13H8O4; MW=228.20) S (g/L) 0.005 0.005 0.012 0.013 0.016 0.019 0.041 0.058 0.003 0.004 0.011 0.023 0.032 0.040 0.066 0.075 0.003 0.003 0.015 0.023 0.036 0.051 0.081 0.096 0.002 0.003 0.009 0.022 0.041 0.080 0.104 0.120

x

[D-55]

106

1.58 1.31 2.85 2.76 3.47 4.00 8.32 11.48 2.68 1.31 2.93 5.51 7.35 8.85 14.21 15.71 3.05 1.52 4.37 5.95 8.63 11.90 18.17 20.82 2.97 1.96 3.05 6.30 10.56 19.51 24.47 27.23

40 305 K 318 K 328 K 338 K 348 K

30 y x 106

T (K) P (bar) 305.15 74 112 152 193 233 274 314 355 318.15 74 112 152 193 233 274 314 355 328.15 74 112 152 193 233 274 314 355 338.15 74 112 152 193 233 274 314 355

y1)

20

10

0 50

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150

250 P (bar)

350

310

348.15

Solubility in Supercritical Carbon Dioxide

74 112 152 193 233 274 314 355

0.002 0.002 0.003 0.020 0.050 0.097 0.124 0.151

2.15 1.34 3.21 6.47 14.09 25.24 30.69 35.88

1: The order of magnitude (x 104) of y in the original table must have been misprinted and thus was corrected to "x 106" based on S. Some y values at low pressures at each temperature still do not match S values. Synonym: 1,6-Dihydroxyxanthen-9-one Source: Ghiasvand, A. R.; Hosseini, M.; Sharghi, H.; Yamini, Y.; Shamsipur, M. J. Chem. Eng. Data (1999), 44(6), 1135-1138.

Diiodomethyl p -tolyl sulfone (C8H8I2O2S; MW=422.02)

[D-56]

6

318 K 328 K 338 K

y x 10

6

y x 10 T (K) P (bar) 318 100 12.2 120 170 38.0 200 39.0 225 58.1 250 62.0 80 300 72.6 328 200 63.8 225 70.7 250 89.8 40 300 86.6 338 100 6.3 125 24.3 150 36.7 170 56.0 0 200 84.5 50 225 82.9 250 96.3 300 115.0 Synonym: p-Tolyl diiodomethyl sulfone Source: Sahle-Demessie, E.; Pillai, U. R.; Junsophonsri, S.; Levien, K. L. J. Chem. Eng. Data (2003), 48(3), 541-547.

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150

250 P (bar)

350

Solubility Data D

311

Diisodecyl phosphoric acid (C20H43O4P; MW=378.53) 1)

[D-57]

6

y x 10

6

y x 10 T (K) P (bar) M (mol/l) 8000 897 313 125 0.015 1790 150 0.032 5950 250 0.120 227 323 125 0.003 1060 150 0.017 6270 250 0.120 4000 332 333 150 0.005 2480 200 0.041 4990 250 0.090 431 343 175 0.006 200 0.019 1260 0 250 0.057 3380 100 1: Calculated from M. Synonym: Bis(8-methylnonyl) hydrogen phosphate Source: Meguro, Y.; Iso, S.; Sasaki, T.; Yoshida, Z. Anal. Chem. (1998), 70(4), 774-779.

313 K 323 K 333 K 343 K

200 P (bar)

Dilaurin1) (C27H52O5; MW=456.70)

[D-58]

y x 106

y x 106 T (K) P (bar) 20000 313 150 1886 200 3571 250 4837 300 5400 10000 350 6350 400 6875 338 150 322 0 250 4116 350 16277 100 1: Equimolar mixture of 1,2- and 1,3-dilaurin isomers. Synonyms: Didodecanoyl glycerol; Glycerol dilaurate Source: Ashour, I.; Hammam, H. J. Supercrit. Fluids (1993), 6(1), 3-8. (Also, see the graph in Hammam, H. J. Supercrit. Fluids (1992), 5(2), 101-106).

1,2-Dimethoxybenzene (C8H10O2; MW=138.16) T (K) P (bar) 323.15 20 30 40 50 60 80 100 120

300

y x 106 101 108 134 168 255 757 6770 53000

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313 K 338 K

200

300 P (bar)

400

[D-59]

312

Solubility in Supercritical Carbon Dioxide

353.15

323.15 K 353.15 K 323.15 K

y x 106

20 525 30 468 40 465 60000 50 546 60 661 80 1060 100 1460 130 4770 40000 160 22000 180 45900 393.15 20 3940 30 3080 40 2960 20000 50 2830 60 3040 80 3520 100 4200 130 7140 0 160 12000 0 200 26000 Synonym: 2-Methoxyanisole Source: Lee, M.-J.; Kou, C.-F.; Cheng, J.-W.; Lin, H.-m. Fluid Phase Equil. (1999), 162(1-2), 211-224.

100 P (bar)

200

[D-60]

1,4-Dimethoxybenzene (C8H10O2; MW=138.16) 313.15 K 328.15 K 338.15 K

yx

106

y x 106 T (K) P (bar) 200 313.15 200 47.4 220 57.9 240 61.3 260 63.4 328.15 200 61.4 100 220 84.4 240 106.0 260 121.0 280 132.0 338.15 200 102.0 0 220 139.0 150 240 154.0 260 172.0 280 185.0 Synonyms: 4-Methoxyanisole; Hydroquinone dimethyl ether Source: Lee, L.-S.; Fu, J.-H.; Hsu, H.-L. J. Chem. Eng. Data(2000), 45(2), 358-361.

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200

250 P (bar)

300

Solubility Data D

313

p -Dimethylaminoazobenzene (C14H15N3; MW=225.29) 106

1500

y x 106

yx T (K) P (bar) 308.2 91 437 101 467 152 724 203 829 253 905 318.2 91 322 101 537 152 1030 203 1230 245 1250 Synonym: 4-Dimethylaminoazobenzene Source: Maeda, S.; Mishima, K.; Matsuyama, K.; Baba, M.; Hirabaru, T.; Ishikawa, H.; Hayashi, K.-I. J. Chem. Eng. Data (2001), 46(3), 647-650.

[D-61]

1000

500

308.2 K 318.2 K

0 50

150

250

P (bar)

p -Dimethylaminoazobenzene (C14H15N3; MW=225.29)

[D-62]

yx T (K) P (bar) 333.2 101 390 152 1180 203 1720 253 1980 Synonym: 4-Dimethylaminoazobenzene Source: Mishima, K.; Matsuyama, K.; Ishikawa, H.; Hayashi, K-I.; Maeda, S. Fluid Phase Equil. (2002), 194-197, 895-904.

y x 106

106

2000 1000 0 50

2,5-Dimethylaniline (C8H11N; MW=121.18) T (K) P (bar) 313 80 100 125 150 175 200

yx

106 1440 5160 6600 7600 8030 9520

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150

250

P (bar)

[D-63]

314

Solubility in Supercritical Carbon Dioxide

80 630 10500 100 1650 125 3530 150 4200 175 4820 7000 200 5070 333 80 330 100 620 125 1560 150 2170 3500 175 2930 200 3040 Synonyms: 2,5-Xylidine; 2,5-Dimethylbenzenamine Source: Medina, I.; Bueno, J. L. Fluid Phase Equil. 0 (2001), 187-188, 337-345. 323

y x 106

313 K 323 K 333 K

50

100

150

200

P (bar)

Dimethyl 2H -1-benzopyran-2,3-dicarboxylate (C13H12O5; MW=284.23) S (g/L) 25.65 34.88 45.26 49.31 52.74 61.92 69.41 74.50 78.14 19.57 44.00 61.27 83.36 102.99 119.04 126.78 136.50 148.37

y1) x 106 5103 6541 8156 8620 9003 10344 11388 12033 12495 4493 9011 11798 15344 18329 20601 21468 22671 24323

30000 308 K 318 K

20000 y x 106

T (K) P (bar) 308 122 152 182 213 243 274 304 334 355 318 122 152 182 213 243 274 304 334 355

[D-64]

10000

0 100

1: The y values in the source table did not agree with S and thus were re-calculated based on S. Synonym: Dimethyl 2H-chromene-2,3-dicarboxylate Source: Bahramifar, N.; Yamini, Y.; Ramazani, A.; Noshiranzadeh, N. J. Chem. Eng. Data (2003), 48(5), 1104-1108.

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200

300 P (bar)

400

Solubility Data D

315

Dimethyl 6-bromo-2H-1-benzopyran-2,3-dicarboxylate (C13H11BrO5; MW=327.13) [D-65] S (g/L) 1.02 1.30 1.58 2.17 2.28 2.96 3.29 3.67 4.07 0.79 1.19 1.71 2.39 3.03 3.84 4.73 5.38 6.40 0.63 0.79 1.59 3.01 4.05 5.27 6.66 8.19 9.41 0.13 0.28 1.22 2.71 4.35 5.19 9.53 11.95 13.10 0.10 0.26 1.15 2.50 4.27 7.69 11.48 13.15 15.21

y x 106 178 213 251 333 341 435 474 521 573 161 214 290 389 478 589 712 794 936 164 162 294 525 676 853 1049 1261 1430 46 68 251 512 775 888 1575 1923 2073 41 74 265 516 818 1396 1996 2217 2517

3000

2000 y x 106

T (K) P (bar) 308 122 152 182 213 243 274 304 334 355 318 122 152 182 213 243 274 304 334 355 328 122 152 182 213 243 274 304 334 355 338 122 152 182 213 243 274 304 334 355 348 122 152 182 213 243 274 304 334 355

308 K 318 K 328 K 338 K 348 K

1000

0 100

Synonym: Dimethyl 6-bromo-2H-chromene-2,3-dicarboxylate Source: Bahramifar, N.; Yamini, Y.; Ramazani, A.; Noshiranzadeh, N. J. Chem. Eng. Data (2003), 48(5), 1104-1108.

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200

300 P (bar)

400

316

Solubility in Supercritical Carbon Dioxide

2,3-Dimethylhexane (C8H18; MW=114.23)

[D-66]

106

8000

y x 106

yx T (K) P (bar) 318.15 120 1440 140 3650 160 4430 200 5510 240 5930 328.15 120 475 140 3820 160 5630 200 6780 240 7130 Source: Lee, L.-S.; Huang, J.-F.; Zhu, O.-X. J. Chem. Eng. Data (2001), 46(5), 1156-1159.

4000 318.15 K 328.15 K

0 100

150

200

250

P (bar)

2,3-Dimethylnaphthalene (C12H12; MW=156.22)

y x 106

T (K) P1) (bar) y1) x 106 308.15 101 3470 8000 101 3550 308 K 3840 109 323 K 109 4060 6000 116 3990 116 4190 129 4430 4000 136 4520 137 4550 144 4410 2000 144 4500 323.15 108 2030 115 3270 122 4080 0 122 4350 100 129 4700 135 5510 144 6730 1: Obtained by digitizing the graph in the original article. Source: Johnston, K. P.; Barry, S. E.; Read, N. K.; Holcomb, T. R. Ind. Eng. Chem. Res. (1987), 26(11), 2372-2377.

[D-67]

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125 P (bar)

150

Solubility Data D

317

2,3-Dimethylnaphthalene (C12H12; MW=156.22) 106

10000

y x 106

yx T (K) P (bar) 308 99 2200 143 4400 194 5410 242 5820 280 6430 318 99 1280 145 4790 195 6370 242 6880 280 7190 328 99 340 146 4450 197 7140 241 8470 9010 280 Source: Kurnik, R. T.; Holla, S. J.; Reid, R. C. J. Chem. Eng. Data (1981), 26(1), 47-51.

[D-68]

308 K 318 K 328 K

5000

0 50

150

250 P (bar)

2,3-Dimethylnaphthalene (1) + 2,6-Dimethylnaphthalene (2) Mixture

10000

y x 106

y2 x 106 T (K) P (bar) y1 x 106 308 120 3920 3040 140 4340 3360 160 4940 3870 180 5210 4020 200 5680 4380 220 6000 4620 240 6030 4570 260 6160 4620 280 6400 4740 318 120 3670 3400 140 5180 4470 160 6510 5480 180 7360 6140 200 7950 6590 220 8240 6780 240 9010 7390 260 9450 7580 10100 8130 280 Source: Kurnik, R. T.; Reid, R. C. Fluid Phase Equil. (1982), 8(1), 93-105.

350

[D-69]

2,3-DN 308 K 2,3-DN 318 K 2,6-DN 308 K 2,6-DN 318 K

6000

2000 100

CAT4240—CHAPTER 4—1/11/2006—19:28—SRIDHAR—XML MODEL C – pp. 271–334

200 P (bar)

300

318

Solubility in Supercritical Carbon Dioxide

2,6-Dimethylnaphthalene (C12H12; MW=156.22) 106

4000 308.2 K

y x 106

yx T (K) P (bar) 308.2 79 1070 91 1950 121 2660 146 3060 328.2 100 509 109 1070 121 2010 127 2700 Source: Iwai, Y.; Mori, Y.; Hosotani, N.; Higashi, H.; Furuya, T.; Arai, Y.; Yamamoto, K.; Mito, Y. J. Chem. Eng. Data (1993), 38(4), 509-511.

[D-70]

323.2 K

2000

0 50

100 P (bar)

2,6-Dimethylnaphthalene (C12H12; MW=156.22)

[D-71]

6000 308 K 323 K

y x 106

T (K) P1) (bar) y1) x 106 308.15 101 2660 101 2760 109 2980 109 3100 116 3210 122 3210 122 3370 129 3370 136 3490 137 3540 144 3490 144 3720 323.15 108 1810 115 2910 122 3650 129 4310 135 4870 144 5360

150

4000

2000

0 100

1: Obtained by digitizing the graph in the original article . Source: Johnston, K. P.; Barry, S. E.; Read, N. K.; Holcomb, T. R. Ind. Eng. Chem. Res. (1987), .26(11), 2372-2377

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125 P (bar)

150

Solubility Data D

319

2,6-Dimethylnaphthalene (C12H12; MW=156.22) 106

10000 308 K 318 K 328 K

y x 106

yx T (K) P (bar) 308 97 1900 145 2960 195 3830 245 4010 280 4470 318 98 757 146 3940 194 5090 244 6270 280 6770 328 96 305 146 4310 195 6150 246 7990 9210 280 Source: Kurnik, R. T.; Holla, S. J.; Reid, R. C. J. Chem. Eng. Data (1981), 26(1), 47-51.

[D-72]

5000

0 0

100

200 P (bar)

2,6-Dimethylnaphthalene (C12H12; MW=156.22)

[D-73]

4000 y x 106

T (K) P1) (bar) y1) x 106 308.15 94.6 746 107.3 1130 134.2 2180 172.3 2750 197.7 2900 226.0 3050 1: Obtained by digitizing the graph in .the original article Source: Nakatani, T.; Ohgaki, K.; Katayama, T. Ind. Eng. Chem. Res. (1991), 30(6), 1362-1366.

2000

0 50

150

250

P (bar)

2,6-Dimethylnaphthalene (1) + 2,7-Dimethylnaphthalene (2) Mixture 106

y1 x y2 x T (K) P (bar) 308.2 90 2200 3220 99 2640 3820 120 3120 4550 148 3770 5470 198 4240 6170 246 4370 6380 318.2 90 475 682 100 1910 2730 120 3690 5310 149 5150 7420 198 6630 9550 247 7260 10500 Source: Iwai, Y.; Mori, Y.; Hosotani, N.; Higashi, H.; Furuya, T.; Arai, Y.; Yamamoto, K.; Mito, Y. J. Chem. Eng. Data. (1993), 38(4), 509-511.

[D-74]

12000

y x 106

106

300

308.2 K (1) 318.2 K (1) 308.2 K (2) 318.2 K (2)

8000

4000

0 0

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100

200 P (bar)

300

320

Solubility in Supercritical Carbon Dioxide

2,7-Dimethylnaphthalene (C12H12; MW=156.22) 106

15000

y x 106

yx T (K) P (bar) 308.2 88 2680 107 3510 150 4720 200 5290 242 5740 328.2 100 745 110 1750 149 6640 198 10100 249 11900 Source: Iwai, Y.; Mori, Y.; Hosotani, N.; Higashi, H.; Furuya, T.; Arai, Y.; Yamamoto, K.; Mito, Y. J. Chem. Eng. Data (1993), 38(4), 509-511.

[D-75]

308.2 K 328.2 K

10000 5000 0 50

150 P (bar)

250

Dimethyl 3H -naphtho[2,1- b ]pyran-2,3-dicarboxylate (C17H14O5; MW=298.29) S (g/L) 1.16 1.40 1.58 2.12 2.35 2.46 2.92 3.14 0.94 1.30 1.59 2.19 3.07 3.55 4.36 4.97 0.68 1.13 1.56 2.39 3.15 4.17 5.55 6.40 0.60 0.98 1.94 3.14 4.20 5.84

yx

208 242 265 348 378 389 455 485 185 242 284 380 518 585 707 797 153 229 298 438 559 720 938 1066 157 222 401 614 787 1060

2000

1500

y x 106

T (K) P (bar) 308 152 182 213 243 274 304 334 355 318 152 182 213 243 274 304 334 355 328 152 182 213 243 274 304 334 355 338 152 182 213 243 274 304

[D-76]

106

308 K 318 K 328 K 338 K 348 K

1000

500

0 100

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200

P (bar)

300

400

Solubility Data D

321

334 6.40 1131 355 8.61 1496 348 152 0.43 133 182 0.61 153 213 1.31 296 243 2.86 600 274 4.12 821 304 6.03 1150 334 8.20 1518 355 9.62 1746 Synonym: Dimethyl 3H-benzo[f]chromene-2,3-dicarboxylate Source: Bahramifar, N.; Yamini, Y.; Ramazani, A.; Noshiranzadeh, N. J. Chem. Eng. Data (2003), 48(5), 1104-1108.

2,4-Dinitrophenol (C6H4N2O5; MW=184.11) S (g/L) 4.012 5.416 6.064 8.054 8.894 9.553 12.959 14.197 15.125 3.580 5.328 10.579 17.969 20.510 22.574 24.474 33.591 0.845 2.057 5.192 11.487 14.856 17.726 21.320 38.990 43.308 47.313 0.236 5.555 6.272 12.580 13.389 15.137

yx

1240 1550 1660 2140 2300 2420 3230 3480 3650 1290 1670 3100 4770 5420 5830 6190 8380 386 718 1640 3410 4240 4890 5730 10300 11200 12000 141 1600 1720 3350 3470 3770

15000 308 K 318 K 328 K 338 K 348 K

10000 y x 106

T (K) P (bar) 308 121.6 162.1 202.6 243.2 283.7 324.2 364.8 405.3 445.8 318 121.6 162.1 202.6 283.7 324.2 364.8 405.3 445.8 328 121.6 162.1 202.6 243.2 283.7 324.2 364.8 405.3 445.8 486.4 338 121.6 162.1 202.6 243.2 283.7 364.8

[D-77]

106

5000

0 0

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200

P (bar)

400

600

322

Solubility in Supercritical Carbon Dioxide

348

121.6 162.1 202.6 243.2 283.7 324.2 364.8 405.3 445.8

1.611 5.324 6.014 15.182 24.679 32.585 39.675 44.750 50.707

1170 2450 2280 5170 7860 10200 11600 12700 14000

Source: Shamsipur, M.; Fat'hi, M. R.; Yamini, Y.; Ghiasvand, A. R. J. Supercrit. Fluids (2002), 23(3), 225-231.

[D-78]

2,5-Dinitrophenol (C6H4N2O5; MW=184.11) S (g/L) 6.141 6.630 9.353 11.225 13.283 15.427 16.778 17.144 17.512 2.488 4.749 10.162 15.122 20.150 22.143 22.807 24.406 1.519 3.897 8.337 10.215 14.005 17.194 21.217 21.838 23.748 0.872 2.843 5.833 9.518 13.384 17.380 21.321 23.635 25.307

y x 10

1910 1900 2570 2990 3440 3910 4180 4200 4230 894 1490 2980 4240 5470 5730 5770 6090 693 1360 2630 3040 3990 4740 5700 5740 6120 525 1130 2010 3020 4020 5020 5970 6450 6750

10000

y x 106

T (K) P (bar) 308 121.6 162.1 202.6 243.2 283.7 324.2 364.8 405.3 445.8 318 121.6 162.1 202.6 243.2 283.7 364.8 405.3 445.8 328 121.6 162.1 202.6 243.2 283.7 324.2 364.8 405.3 445.8 338 121.6 162.1 202.6 243.2 283.7 324.2 364.8 405.3 445.8

6

308 K 318 K 328 K 338 K 348 K

5000

0 0

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200

400 P (bar)

600

Solubility Data D

323

348

121.6 0.433 316 162.1 1.116 514 202.6 2.927 1110 243.2 7.044 2400 283.7 12.800 4080 324.2 18.288 5550 364.8 23.416 6840 405.3 28.459 8070 445.8 32.899 9100 486.4 34.920 9440 Source: Shamsipur, M.; Fat'hi, M. R.; Yamini, Y.; Ghiasvand, A. R. J. Supercrit. Fluids (2002), 23(3), 225-231.

[D-79]

Dinonyl phthalate (C26H42O4; MW=418.61) yx

1270 2500 3900 5100 6300 7000 7800 1110 1680 2700 3200 4600 5300 6200 170 1050 1740 2100 3100 4100 4700 5800 6900 1500 2400 3400 4200 4900 5600 830 3000 3800 4800 6000

9000 303.2 K 308.2 K 313.2 K 318.2 K 323.2 K 328.2 K

6000 y x 106

T (K) P (bar) 303.2 79 94 111 126 139 150 158 308.2 92 98 113 121 136 144 155 313.2 90 105 113 119 133 146 154 167 179 318.2 124 136 149 162 169 178 323.2 125 161 170 183 195

106

3000

0 50

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100

150 P (bar)

200

324

Solubility in Supercritical Carbon Dioxide

328.2

149 1460 161 2100 171 2800 181 3500 192 4300 208 5600 Synonym: Dinonyl 1,2-benzenedicarboxylate Source: Sovova, H.; Jez, J.; Khachaturyan, M. Fluid Phase Equil. (1997), 137(1-2), 185-191.

[D-80]

Dinonyl phthalate (C26H42O4; MW=418.61) T (K)

P (bar)

Ethanol1)

303 K, 90 bar 303 K, 100 bar 313 K, 100 bar

y x 106

y x 106 (mol%) 303.15 90 0.0 2200 15000 1.5 4200 2.3 5300 2.5 5700 3.7 7000 3.9 7900 10000 5.5 10300 100 0.0 3000 2.1 6300 2.2 6300 3.8 9200 5000 5.0 11700 5.8 12900 313.15 100 0.0 800 0.3 1000 0.5 1100 0 1.4 1900 0 1.5 1800 2.1 2400 2.6 2900 1: Cosolvent in CO2. Synonym: Dinonyl 1,2-benzenedicarboxylate Source: Sovova, H.; Rat, V.; Khachaturyan, M.; Vlcek, D. J. Supercrit. Fluids (1999), 14(2), 145-149.

Dinonyl phthalate (C26H42O4; MW=418.61) T (K)

P (bar) n-Heptane1) y x 106 (mol%) 303.15 90 0.0 2200 0.3 2800 0.6 3300 0.6 3400 0.7 3400 0.9 3800 1.0 3900 1.9 6100

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2

4

6

Ethanol (mol%)

[D-81]

Solubility Data D

313.15

100

0.0 0.1 0.6 0.7 0.8 0.9 1.0 1.1 1.7 0.0 0.4 0.6 0.8 2.4 2.5

3000 3200 4100 4600 4800 5200 5400 5700 7600 800 1300 1400 1700 4000 4800

9000

6000 y x 106

100

325

3000

1: Cosolvent in CO2. Synonym: Dinonyl 1,2-benzenedicarboxylate Source: Sovova, H.; Rat, V.; Khachaturyan, M.; Vlcek, D. J. Supercrit. Fluids (1999), 14(2), 145-149.

303 K, 90 bar 303 K, 100 bar 313 K, 100 bar

0 0

1

2

n -Heptane (mol%)

[D-82]

Dinonyl phthalate (C26H42O4; MW=418.61) Toluene1) y x 106 (mol%) 303.15 90 0.0 2200 0.7 3400 12000 0.9 3700 1.2 4300 2.0 5500 2.2 5900 4.1 10100 8000 4.2 10600 100 0.0 3000 0.4 3600 1.0 5000 1.1 5100 4000 2.8 8700 313.15 100 0.0 800 0.4 1100 1.0 1700 1.2 2100 0 1.6 2500 0 1.7 2500 3.3 5100 3.7 6400 4.0 7400 4.1 8600 1: Cosolvent in CO2. Synonym: Dinonyl 1,2-benzenedicarboxylate Source: Sovova, H.; Rat, V.; Khachaturyan, M.; Vlcek, D. J. Supercrit. Fluids (1999), 14(2), 145-149. P (bar)

303 K, 90 bar 303 K, 100 bar 313 K, 100 bar

y x 106

T (K)

3

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1

2

3

Toluene (mol%)

4

326

Solubility in Supercritical Carbon Dioxide

Dioctyl ether (C16H34O; MW=242.44)

[D-83]

106

60000 y x 106

yx T (K) P (bar) 320 107.5 9600 109.5 10900 126.5 32600 132.5 50500 Synonyms: Dicaprylyl ether; Octyl ether Source: Schmitt, W. J.; Reid, R. C. Chem. Eng. Comm. (1988), 64, 155-176.

30000

0 100

120 P (bar)

140

Dioctyl phthalate (C24H38O4; MW=390.56) 50

30 40

Synonym: Bis(2-ethylhexyl) phthalate Source: Shende, R. V.; Lombardo, S. J. J. Supercrit. Fluids (2002), 23(2), 153-162.

yx

yx

106

T (K) P (bar) 308.15 400 348.15 400

[D-84]

106

20 300

320

T (K)

340

Diolein (C39H72O5; MW=620.99)

[D-85] 6

w x 10 y x 10 T (K) P (bar) 323.15 151 1600 114 172 2700 192 206 5300 377 241 7900 564 275 10500 751 333.15 151 700 50 172 1500 106 206 3500 249 241 6700 478 275 9900 708 309 13100 940 1: Calculated from w. Synonym: Glycerol dioeate Source: Nilsson, W. B.; Gauglitz, E. J. Jr.; Hudson, J. K. J. Am. Oil Chem. Soc. (1991), 68(2), 87-91.

1000 323.15 K 333.15 K

y x 10

1)

6

6

360

500

0 100

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200 P (bar)

300

Solubility Data D

327

Diphenylamine (C12H11N; MW=169.22)

[D-86]

6

7000 313 K 333 K

6

y x 10 T (K) P (bar) S (g/L) 313.15 60 16.00 5190 333.15 263 19.26 6210 1: Calculated form S. Synonyms: N-Phenylaniline; N -Phenylbenzenamine Source: Ashraf-Khorassani, M.; Taylor, L. T. J. Chem. Eng. Data (1999), 44(6), 1254-1258.

y x 10

1)

6000 5000 100

150

200 P (bar)

250

Diphenylamine (C12H11N; MW=169.22) 160 78 52 100 52 78 160 230 210 230 550 470 600 780 960 990 1170 1150 1880 1960 1700 1700 1910 2090 2490 2200 2960 3020 3200 2940 3330 3550 3440 3760 3630

305.35 K 310.15 K

6000

6

x

[D-87]

106

y x 10

T (K) P1) (bar) w2) (wt%) 305.35 46.8 0.06 66.8 0.03 66.8 0.02 69.2 0.04 70.8 0.02 73.7 0.03 74.9 0.06 75.2 0.09 75.3 0.08 75.4 0.09 75.8 0.21 75.9 0.18 76.1 0.23 76.2 0.30 77.1 0.37 77.4 0.38 77.8 0.45 78.9 0.44 85.4 0.72 85.4 0.75 87.2 0.65 89.3 0.65 89.3 0.73 97.4 0.80 97.4 0.95 100.8 0.84 109.0 1.13 119.3 1.15 119.3 1.22 125.3 1.12 139.2 1.27 139.2 1.35 139.2 1.31 147.2 1.43 147.2 1.38

y3)

300

4000

2000

0 0

50

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100

150

P (bar)

200

250

328

310.15

Solubility in Supercritical Carbon Dioxide

156.1 165.7 165.7 176.3 176.3 200.3 214.0 228.8 228.8

1.42 1.41 1.49 1.57 1.80 2.04 1.93 2.04 2.07

3730 3710 3920 4130 4740 5390 5090 5390 5470

49.7

0.07

180

49.7

0.06

160

49.7 54.7 74.4 75.3 75.7

0.05 0.03 0.09 0.10 0.16

130 80 230 260 420

75.9

0.26

680

76.2

0.34

890

78.9

0.60

1570

82.5

0.70

1830

85.4

0.90

2360

89.3

0.95

2490

109.0

1.30

3410

104.7

1.23

3230

104.7

1.20

3150

119.3

1.57

4130

156.1

1.98

5230

176.3

1.98

5230

187.8

2.38

6300

1: Calculated from temperature and density in the source table. 2: The data in italics were measured in a glass vial with a volume of approximately 1.5 cm3. 3: Calculated from w. Synonyms: N-Phenylaniline; N-Phenylbenzenamine Source: Tsekhanskaya, Yu. V.; Iomtev, M. B.; Mushkina, E. V. Z. Fiz. Khim. (1962), 36, 2187-2193.

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Solubility Data D

329

Diphenylamine (C12H11N; MW=169.22) T (K) P1) (bar)

(mol%)

[D-88]

y1) x 106

102 120 149 200 262 322

0 3070 12000 0 3510 0 4290 0 5660 0 7170 0 7760 8000 Acetone 100 3.7 4540 119 3.7 6000 150 3.7 7320 203 3.7 9460 4000 Ethanol 119 3.7 5370 151 3.7 6440 201 3.7 8490 262 3.7 10600 0 322 3.7 11200 n-Hexane 50 120 3.7 4780 150 3.7 5950 201 3.7 7170 261 3.7 8490 320 3.7 9020 1: Obtained by digitizing the graph in the original article. 2: Cosolvent in CO2 on a solute-free basis. Synonyms: N-Phenylaniline; N-Phenylbenzenamine Source: Zhang, J.; Zhu, M.; Yu, E.; Zhang, Z. Chinese J. Chem. Eng. (1993), 1(4), 239-246.

y x 106

308

Cosolvent2)

Pure CO2 Acetone Ethanol n-Hexane

150

250 P (bar)

Diphenylmethane (C13H12; MW=168.23) T (K)

P (bar)

350

[D-89]

y x 106

73.9 1800 83.2 8900 91.3 11500 110.9 19300 127.5 24900 154.0 31300 176.9 36200 213.3 44000 263.9 58100 328.15 114.1 3700 130.8 9600 162.2 21200 195.4 34200 234.0 49700 267.4 63000 Synonym: Benzylbenzene Source: Chung, S. T.; Shing, K. S. Fluid Phase Equil. (1992), 81, 321-341.

y x 106

308.15

308.15 K 328.15 K

60000 40000 20000 0 0

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100

200 P (bar)

300

330

Solubility in Supercritical Carbon Dioxide

Docosahexaenoic acid ethyl ester (C24H36O2; MW = 356.54) 1)

[D-90]

y2) x 106

S1)

298.2 K 313.2 K 328.2 K

y x 10

6

(g/L) T (K) P (bar) 298.2 69 7.0 1170 8000 3510 103 23.5 4400 138 31.0 5280 172 38.5 0 313.2 69 0.0 2100 103 11.1 4000 3330 125 19.8 4370 138 27.0 6020 152 38.5 6350 172 42.0 0 328.2 69 0.0 314 103 0.9 0 1550 138 7.6 50 2330 144 12.0 3350 152 18.0 172 28.5 4940 1: Obtained by digitizing the graph in the original article. 2: Calculated from S. Synonyms: (all Z)-4,7,10,13,16,19-Docosa docosahexaenoate hexaenoic acid ethyl ester; Ethyl Source: Liang, J. H.; Yeh, A. I. J. Am. Oil Chem. Soc. (1991), 68(9), 687-692.

125

200

P (bar)

Docosahexaenoic acid ethyl ester (C24H36O2; MW = 356.54)

333

95 102 110 125 140 170 99 109 129 150 170 192 128 150 168 190 211

x

[D-91]

106

214 388 703 1060 1570 2710 20 121 616 1170 1750 2420 208 616 1190 1970 2480

3000 313 K 323 K 333 K 373 K

2000 yx

323

(bar)

y1)

106

T (K) 313

P1)

1000

0 50

100

150

200

P (bar)

CAT4240—CHAPTER 4—1/11/2006—19:28—SRIDHAR—XML MODEL C – pp. 271–334

250

Solubility Data D

373

149 180 209 249

331

33 161 489 1150

1: Obtained by digitizing the graph in the original article Synonyms: (all Z)-4,7,10,13,16,19-Docosa hexaenoic acid ethyl ester; Ethyl docosahexaenoate Source: Liong, K.; Foster, N.; Ting, S. Ind. Eng. Chem. Res. (1992), 31(1), 400-4.

Docosane (C22H46; MW=310.60) 20000 y x 106

y x 106 T (K) P (bar) 310 119.0 3200 145.0 6200 189.0 18000 320 119.0 1200 145.0 2800 189.0 11900 Source: Schmitt, W. J.; Reid, R. C. Chem. Eng. Comm. (1988), 64, 155-176.

[D-92] 310 K 320 K

10000

0 100

150

200

P (bar)

Dodecane (C12H26; MW=170.33) wx 28000 51000 103000 200000 317000 405000 483000 28000 51000 103000 200000 317000 405000 483000 28000 51000 103000 200000 317000 405000

y1)

[D-93]

106

x 7400 13700 28800 60700 107000 150000 194000 7400 13700 28800 60700 107000 150000 194000 7400 13700 28800 60700 107000 150000

313.2 K 323,2 K 333.2 K 343.2 K

200000

150000 y x 106

T (K) P (bar) 313.2 85.7 84.9 84.2 83.5 82.8 82.2 79.5 323.2 99.0 101.3 102.8 102.9 101.7 99.1 94.4 333.2 110.4 117.5 122.1 123.3 121.6 117.3

106

100000

50000

0 70

CAT4240—CHAPTER 4—1/11/2006—19:28—SRIDHAR—XML MODEL C – pp. 271–334

90

110 P (bar)

130

150

332

Solubility in Supercritical Carbon Dioxide

7400 343.2 120.0 28000 13700 130.5 51000 28800 141.0 103000 60700 143.0 200000 107000 140.0 317000 134.3 405000 150000 1: Calculated from w. Source: Nieuwoudt, I.; du Rand, M. J. Supercrit. Fluids (2002), 22(3), 185-199.

Dodecyl gallate (C19H30O5; MW=338.44)

20 y x 106

y x 106 T (K) P (bar) 313.1 150 3.1 175 3.4 200 3.9 250 4.7 333.1 150 4.5 175 8.7 200 13.1 250 20.7 Synonyms: Dodecyl 3,4,5-trihydroxybenzoate ; Gallic acid dodecyl ester Source: Cortesi, A.; Kikic, I.; Alessi, P.; Turtoi, G.; Garnier, S. J. Supercrit. Fluids (1999), 14(2), 139-144.

[D-94]

313.1 K 333.1 K

10

0 100

200 P (bar)

Dotriacontane (C32H66; MW=450.87)

[D-95]

106

x T (K) P (bar) S (g/L) 343 184.6 1.36 211 220.0 3.53 493 250.0 5.79 764 280.0 8.30 1048 1263 310.0 10.35 1: Calculated from S. Source: Chartier, T.; Delhomme, E.; Baumard, J. F.; Marteau, P.; Subra, P.; Tufeu, R. Ind. Eng. Chem. Res. (1999), 38(5), 1904-1910.

1400 y x 106

y1)

300

700 0 150

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250 P (bar)

350

Solubility Data D

333

Dotriacontane (C32H66; MW=450.87) x

[D-96]

106

14.0 19.0 22.0 29.0 34.0 36.0 43.0 4.4 32.0 66.0 90.0 120.0 150.0 180.0 0.8 24.0 99.0 200.0 310.0 420.0 560.0

600 308.2 K 318.2 K 328.2 K

400 y x 106

T (K) P (bar) 308.2 100 120 140 160 180 200 240 318.2 100 120 140 160 180 200 240 328.2 100 120 140 160 180 200 240

y1)

200

0 50

150 P (bar)

250

1: All the data at 100 bar and data at 328.2 K and 120 bar (in italics) are extrapolated values in the original article. Source: Chandler, K.; Pouillot, F. L. L.; Eckert, C. A. J. Chem. Eng. Data (1996), 41, 6-10.

Dotriacontane (C32H66; MW=450.87) P (bar)

yx

[D-97]

106

308.15 91.9 30 103.8 20 108.6 80 108.7 80 125.1 70 146.5 50 161.0 70 Source:: K King, M. B.; Alderson, D. A.; Fallah, F. H.; Kassim, D. M.; Sheldon, J. R.; Mahmud, R. S. in: Chapter 2, Chemical Engineering at Supercritical Fluid Conditions, Paulaitis, M. E.; Penninger, J. M. L.; Gray, Jr., R. D.; Davidson, P. (Eds.) Ann Arbor Science, 1983, pp. 31-80.

100 y x 106

T (K)

50

0 80

CAT4240—CHAPTER 4—1/11/2006—19:28—SRIDHAR—XML MODEL C – pp. 271–334

120 P (bar)

160

334

Solubility in Supercritical Carbon Dioxide

[D-98]

Dotriacontane (C32H66; MW=450.87) 106

1200 318.2 K 328.2 K 338.2 K

800

y x 106

yx T (K) P (bar) 318.2 46.9 390 60.8 334 87.9 314 112.0 305 134.8 328 155.5 363 181.0 520 203.1 628 328.2 48.3 300 61.2 252 87.4 269 108.8 306 131.2 316 153.5 430 177.9 538 205.8 659 338.2 47.2 372 61.0 318 85.5 256 108.2 294 131.7 362 153.8 494 178.6 668 205.5 1162 Source: Yau, J. S.; Tsai, F. N. J. Chem. Eng. Data .(1993), 38(2), 171-174

400

0 0

CAT4240—CHAPTER 4—1/11/2006—19:28—SRIDHAR—XML MODEL C – pp. 271–334

100 P (bar)

200

5

Solubility Data E

Eflucimibe (C29H43NO2S; MW=469.72)

308.15 98.6 103.5 125.6 153.5 198.5 222.8 254.1 274.6 297.3 318.15 93.3 99.2 107.9 120.1 148.6 150.8 195.9 202.0 253.0 255.5 301.9 318.15 122.5 149.7 171.7 201.0 267.6 291.1 318.15 200.0 200.0 200.0 200.0 200.0 200.0 200.0

Cosolvent (mol%) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 DMSO 2.0 2.0 2.0 2.0 2.0 2.0 0.9 1.3 2.0 2.1 2.6 2.7 3.3

y x 106 0.07 0.07 0.14 0.24 0.42 0.50 0.56 0.57 0.64 0.01 0.03 0.08 0.12 0.35 0.36 0.68 0.74 1.08 1.12 1.57

40 308 K, Pure CO2 318 K, Pure CO2 318 K, 2% DMSO 318 K, 5% EtOH

30 6

P (bar)

y x 10

T (K)

[E-1]

20

10

0 50

150

250

350

P (bar)

3.28 7.23 11.38 15.23 28.26 36.54 2.10 5.19 11.07 15.23 29.98 34.33 46.90

335

CAT4240—CHAPTER 5—31/10/2006—18:47—KADAMBADI—XML MODEL C – pp. 335–349

336

Solubility in Supercritical Carbon Dioxide

Ethanol 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 4.0 7.6 7.7 10.2 16.2 17.1

90

1.11 1.20 2.04 2.09 2.93 3.10 4.84 7.28 8.82 9.08 9.08 3.46 14.42 14.31 28.59 73.74 80.27

DMSO EtOH 318.15 K 200 bar

60 6

98.0 99.5 122.5 122.7 148.0 149.0 174.5 224.0 271.7 296.9 303.6 318.15 200.0 200.0 200.0 200.0 200.0 200.0

y x 10

318.15

30

0

0

Synonym: (S)-2-(Dodecylthio)-N-(4-hydroxy-2,3,5trimethylphenyl)-2-phenylacetamide Source: Sauceau, M.; Letourneau, J.-J.; Freiss, B.; Richon, D.; Fages, J. J. Supercrit. Fluids (2004), 31(2), 133-140.

5 10 15 Cosolvent (mol%)

Eicosane (C20H42; MW=282.55) T (K)

P (bar)

20

[E-2]

6

y x 10

310 K 320 K

6

y x 10

111.5 3800 126.0 5000 151.5 6700 205.0 9900 280.0 13000 320 111.5 1600 126.0 3100 151.5 6100 205.0 10200 280.0 16000 Source: Schmitt, W. J.; Reid, R. C. Chem. Eng. Comm. (1988), 64, 155-176.

18000

310

9000

0 100

CAT4240—CHAPTER 5—31/10/2006—18:47—KADAMBADI—XML MODEL C – pp. 335–349

200 P (bar)

300

Solubility Data E

337

Eicosane (C20H42; MW=282.55)

[E-3] 6

y x 10 T (K) P (bar) w x 10 315.9 100.9 18000 2800 196.1 55000 5500 320.6 109.1 18000 2800 157.4 34000 5500 197.9 55000 8900 329.6 121.8 18000 2800 166.2 34000 5500 205.0 55000 8900 339.1 135.0 18000 2800 186.8 34000 5500 212.3 55000 8900 281.4 132000 23100 348.3 140.9 18000 2800 203.1 34000 5500 219.7 55000 8900 279.0 132000 23100 1: Calculated from w. Source: Nieuwoudt, I.; du Rand, M. J. Supercrit. Fluids (2002), 22(3), 185-199.

315.9 K 320.6 K 329.6 K 339.1 K 348.3 K

20000 6

1)

y x 10

6

10000

0 100

200 P (bar)

Eicosanoic acid (C20H40O2; MW=312.53) T (K)

P (bar)

300

[E-4]

6

y x 10

308.2

300 308.2 K 318.2 K 328.2 K

6

200 y x 10

38.2 12.3 70.3 12.7 117.1 23.2 138.5 35.9 163.0 46.9 187.1 56.8 209.5 62.3 318.2 37.5 11.2 91.9 11.2 115.9 22.2 139.9 45.2 163.3 61.1 187.1 80.2 210.4 89.0 328.2 33.7 6.3 67.3 9.0 91.3 16.8 135.9 58.4 161.3 103.4 188.8 178.7 211.2 287.3 Synonym: Arachidic acid Source: Yau, J.-S.; Tsai, F.-N. J. Chem. Eng. Data (1994), 39(4), 827-829.

100

0

0

CAT4240—CHAPTER 5—31/10/2006—18:47—KADAMBADI—XML MODEL C – pp. 335–349

100 P (bar)

200

338

Solubility in Supercritical Carbon Dioxide

1-Eicosanol (C20H42O; MW=298.55) 1)

[E-5]

6

y x 10

6

T (K) P (bar) y x 10 308.2 37.5 22 64.6 21 92.4 77 116.3 124 142.3 151 164.4 181 186.6 194 209.0 230 318.2 36.2 20 63.4 15 93.7 42 116.7 203 140.2 424 164.4 538 189.2 608 212.6 699 328.2 37.5 18 73.0 15 89.9 16 113.7 100 140.6 677 161.6 1258 186.8 1782 210.4 2210 1: The obviously-mistyped pressure (412.3 bar at 308.2 K) in the source table was corrected to 142.3 bar. Synonym: Arachidyl alcohol Source: Yau, J.-S.; Tsai, F.-N. J. Chem. Eng. Data (1994), 39(4), 827-829.

308.2 K 318.2 K 328.2 K

2000 1500 1000 500 0 0

Eicosapentaenoic acid ethyl ester (C22H34O2; MW=330.50) 1) 1) T (K) P (bar) S (g/L)

298.2

313.2

69 103 138 172 69 103 125 138 152 172

15.4 46.5 58.5 63.7 0.0 15.4 26.5 31.6 42.2 47.5

y2) x 106 2770 7470 8920 9380 0 3130 4810 5510 7120 7740

CAT4240—CHAPTER 5—31/10/2006—18:47—KADAMBADI—XML MODEL C – pp. 335–349

100

200

P (bar)

[E-6]

Solubility Data E

339

10000

0 69 0.0 320 103 0.9 2240 138 10.3 5000 3330 144 15.9 4480 152 22.2 5430 172 29.1 1: Obtained by digitizing the graph in the original article. 2: Calculated from S. Synonym: (all-Z )-5,8,11,14,17-Eicosapentaenoic 0 acid ethyl ester; Ethyl eicosapentaenoate 50 Source: Liang, J. H.; Yeh, A. I. J. Am. Oil Chem. Soc. (1991), 68(9), 687-692.

y x 10

6

328.2

298 K 313 K 328 K

125 P (bar)

Eicosatrienoic acid ethyl ester (C22H38O2; MW = 334.54)

[E-7]

6

T (K) P (bar) y x 10 313 90 500 100 2160 114 4300 129 6110 143 7880 333 129 1220 150 2750 169 4440 189 6550 209 8200 373 149 90 180 490 208 2230 248 4410 1: Obtained by digitizing the graph in the original article. Source: Liong, K.; Foster, N.; Ting, S. Ind. Eng. Chem. Res. (1992), 31(1), 400-404.

9000

6

1)

313 K 333 K 373 K

6000

y x 10

1)

3000

0 50

Emodin (C15H10O5; MW=270.24) 1) 2) 3) T (K) P (bar) S (μg/Nl )

313.2

89 489 994 1495

200

0.89 4.80 6.49 8.39

y4) x 106 0.073 0.395 0.535 0.691

CAT4240—CHAPTER 5—31/10/2006—18:47—KADAMBADI—XML MODEL C – pp. 335–349

150

250

P (bar)

[E-8]

340

Solubility in Supercritical Carbon Dioxide

y x 106

1989 0.740 8.98 9.60 2389 0.791 1.0 1: Calculated from temperature and density obtained by digitizing the original graph. 2: Obtained by digitizing the graph in 0.5 the original article. 3: "Nl" means "Normliter," which is one liter at 273.15 K and 1 atm. 4: Calculated from S. 0.0 Synonym: 1,3,8-Trihydroxy-6-methylanthraquinone 0 Source: Stahl, E.; Schilz, W.; Schutz, E.; Willing, E. Angew. Chem. Int. Ed. Engl. (1978), 17, 731-738.

1000

2000

3000

P (bar)

Endrin (C12H8Cl6O; MW=380.91)

[E-9]

6

313.1 K 333.1 K

y x 10

6

y x 10 T (K) P (bar) 2000 313.1 100 340 130 769 160 1090 190 1460 1000 220 1640 333.1 100 18 130 259 160 806 190 1370 0 220 1910 50 Synonym: 1,2,3,4,10,10-Hexachloro6,7-epoxy-1,4,4a,5,6,7,8,8a-octahydroendo-1,4-endo-5,8-dimethanonaphthalene Source: Macnaughton, S. J.; Kikic, I.; Rovedo, G.; Foster, N. R.; Alessi, P. J. Chem. Eng. Data (1995), 40(3), 593-597.

Epicatechin (C15H14O6; MW=290.27) T (K)

P (bar)

1)

Ethanol (wt%)

y x 106

313.2

80 90 100 110 120

5 5 5 5 5

51 474 926 1410 2182

313.2

80 90

10 10

386 697

CAT4240—CHAPTER 5—31/10/2006—18:47—KADAMBADI—XML MODEL C – pp. 335–349

150 P (bar)

250

[E-10]

Solubility Data E

341

6000

5% 10% 15% 20% 25% 30%

y x 10

6

100 10 1448 110 10 2574 313.2 80 15 882 90 15 1503 4000 100 15 2947 313.2 80 20 1367 90 20 2323 100 20 4589 313.2 80 25 2004 2000 90 25 5356 313.2 80 30 4902 1: Cosolvent in CO2. Synonyms: Epicatechol; (—)-(2R, 3R)-5,7,3',4'0 Tetrahydroxyflavan-3-ol Source: Chafer, A.; Berna, A.; Monton, J. B.; Munoz, R. 75 J. Supercrit. Fluids (2002), 24(2), 103-109.

100 P (bar)

Ergosterol (C28H44O; MW=396.65) T (K)

P (bar)

125

[E-11]

6

y x 10

y x 10

6

250.8 1.0 276.7 1.2 Synonyms: (3b ,22E )-Ergosta-5,7,22trien-3-ol; 24-Methylcholesta-5,7,22trien-3b -ol Source: Wong, J. M.; Johnston, K. P. Biotech. Prog. (1986), 2(1), 29-39.

1.3

308.2

0.9 240

260

280

P (bar)

Ergosterol (C28H44O; MW=396.65) T (K)

P (bar)

313.15

70 132 172 200 210 242

313.15

110 135 165 200 247

313.15

108 123

Cosolvent (wt%) 0.0 0.0 0.0 0.0 0.0 0.0 Acetone 3.0 3.0 3.0 3.0 3.0 Methanol 3.0 3.0

y1) x 106 2 12 20 22 24 27 100 100 130 230 230 21 64

CAT4240—CHAPTER 5—31/10/2006—18:47—KADAMBADI—XML MODEL C – pp. 335–349

[E-12]

342

Solubility in Supercritical Carbon Dioxide

86 100 100

110 135 165 207 242

3.0

10.0

1.3 5.0 7.1 9.3

270 Pure CO2 Acetone Methanol Water

180 6

313.15

3.0 3.0 3.0 Water 3.0 3.0 3.0 3.0

y x 10

172 207 242

1: Obtained by digitizing the graph in the original article. Some data may not be accurate as the source graph is in a semi-log scale with a small span. Synonyms:(3b ,22E )-Ergosta-5,7,22-trien-3-ol; 24-Methylcholesta-5,7,22-trien-3 b-ol Source : Noh, M. J.; Kim, T. G.; Hong, I. K.; Yoo, K.-P. Korean J. Chem. Eng. (1995), 12(1), 48-55.

90

0 50

150 P (bar)

Erythromycin (C37H67NO13; MW=733.93)

6

3000

y x 10

P (bar)

[E-13]

4

M x 10 y x 106 (mol/L) 313.15 150 66 380 313.25 200 170 880 313.35 250 170 880 313.15 300 180 890 333.15 150 190 1400 333.25 200 280 1800 333.25 250 320 1800 333.35 300 380 2100 Source: Burgos-Solorzano, G. I.; Brennecke, J. F.; Stadtherr, M. A. Fluid Phase Equil (2004), 220(1), 57-69. T (K)

2000

313.25 K 333.25 K

1000 0 100

200

60

6

6

1)

[E-14]

y x 10

6

300

P (bar)

b -Estradiol (C18H24O2; MW=272.38) y x 10 T (K) P (bar) w x 10 308 105 10.5 1.7 140 48.3 7.7 179 73.2 11.7 220 126.0 20.1 318 110 21.5 3.4 144 47.0 7.5 153 74.1 11.8 180 107.0 17.1 220 181.0 28.9 328 114 15.8 2.5 141 77.8 12.4 181 203.0 32.4 217 305.0 48.7 1: Calculated from w. Synonym: Estra-1,3,5(10)-triene-3,17-diol Source: Guney, O.; Akgerman, A. J. Chem. Eng. Data (2000), 45(6), 1049-1052.

250

308 K 318 K 328 K

40

20

0 50

CAT4240—CHAPTER 5—31/10/2006—18:47—KADAMBADI—XML MODEL C – pp. 335–349

150 P (bar)

250

Solubility Data E

343

b -Estradiol (C18H24O2; MW=272.38) Ethanol (wt%)

200

333

172

343

172

w x 106

y2) x 106

0 5

276 3450

44.1 554.1

0 10 0 13

174 1090 104 777

27.8 175.1 16.6 124.9

6

323

P (bar)

[E-15] 600

y x 10

T (K)

1)

400

200

1: Cosolvent in CO 2. 2: Calculated from w. Synonym: Estra-1,3,5(10)-triene-3,17-diol Source: Guney, O.; Akgerman, A. J. Chem. Eng. Data (2000), 45(6), 1049-1052.

Ethyl centralite (C17H20N2O; MW=268.35) 6

0 0

5 10 Ethanol (wt%)

15

[E-16] 60000 304 K 333 K

6

y x 10 T (K) P (bar) S (g/L) 4952 304 152 25.65 333 303 290.70 54060 1: Calculated form S. Synonym: N ,N -Diethyl-N ,N 'diphenylurea; N ,N '-Diethylcarbanilide Source: Ashraf-Khorassani, M.; Taylor, L. T. J. Chem. Eng. Data (1999), 44(6), 1254-1258.

y x 10

1)

323 K 333 K 343 K

0 0

Ethylene glycol (C2H6O2; MW=62.07)

100

200 P (bar)

300

400

[E-17]

100000 y x 10

6

6

y x 10 T (K) P (bar) 325.15 344.7 73380 551.6 22270 8460 689.5 Synonym: 1,2-Ethanediol Source: Eissier, R.; Friedrich, J. P. J. Am. Oil Chem. Soc. (1988), 65(5), 764-767.

30000

50000 0 300

CAT4240—CHAPTER 5—31/10/2006—18:47—KADAMBADI—XML MODEL C – pp. 335–349

500 P (bar)

700

344

Solubility in Supercritical Carbon Dioxide

[E-18]

2-Ethyl-1-hexanol (C8H18O; MW=130.23) 6

80000 313 K 323 K

60000

y x 10

6

y x 10 T (K) P (bar) 313 68 600 72 800 81 1600 90 15000 99 37900 110 44500 120 43400 126 44700 135 44900 144 44500 153 48400 180 45800 323 68 800 72 1000 81 1400 110 14800 120 44600 126 69200 135 66600 144 69100 153 66400 180 68700 Source: Ghaziaskar, H. S.; Eskandari, H.; Daneshfar, A. J. Chem. Eng. Data (2003), 48(2), 236-240.

40000

20000

0 50

100

P (bar)

150

[E-19]

2-Ethylhexanoic acid (C8H16O2; MW=144.21) 313

323

P (bar) 68 72 90 99 110 120 126 135 144 153 180 68 72 90 99 110 120 126 135 144

y x 10

6

700 800 4000 18100 22200 33600 35700 35900 41500 43800 41300 900 1100 2400 6700 14700 25400 39200 48300 47300

313 K

60000

y x 106

T (K)

200

323 K

40000

20000

0 50

100

CAT4240—CHAPTER 5—31/10/2006—18:47—KADAMBADI—XML MODEL C – pp. 335–349

150 P (bar)

200

Solubility Data E

345

153 53100 180 62100 Synonym: a-Ethylcaproic acid Source: Ghaziaskar, H. S.; Eskandari, H.; Daneshfar, A. J. Chem. Eng. Data (2003), 48(2), 236-240. 1)

2-Ethyl-1-hexanol (1) + 2-Ethylhexanoic acid (2) Mixture 40000 Acid/Alcoh 1.00 30200 31600 1.00 25800 25100 1.00 23400 23000 1.00 15000 12600 138 0.33 31800 11700 0.50 25900 13500 1.00 22400 21700 2.00 16500 28000 3.00 13600 29300 1: Solubility was measured from an equimolar mixture of 1 and 2. Source: Ghaziaskar, H. S.; Eskandari, H.; Daneshfar, A. J. Chem. Eng. Data (2003), 48(2), 236-240.

y x 10

313 323 333 343 333

6

y2 x 106

20000 1 2

0 310

330 T (K)

40000

350

6

138

ol mole ratio y1 x 106

y x 10

P (bar) T (K)

[E-20]

20000 1 2

0

0

1 2 3 Acid/Alcohol mole ratio

Ethyl myristate (C16H32O2; MW=256.42)

[E-21]

6

40000 30000 y x 106

y x 10 T (K) P (bar) 313.15 89.1 9000 91.6 10000 92.5 18000 93.4 35000 93.4 37000 323.15 111.4 9000 114.9 10000 115.5 18000 119.6 35000 120.3 37000 333.15 131.5 9000 137.2 10000 136.2 18000 143.7 35000 144.4 37000 Synonyms: Myristic acid ethyl ester; Tetradecanoic acid ethyl ester Source: Crampon, C.; Charbit, G.; Neau, E. J. Supercrit. Fluids (1999), 16(1), 11-20.

20000 10000

313.15 K 323.15 K 333.15 K

0 50

100

CAT4240—CHAPTER 5—31/10/2006—18:47—KADAMBADI—XML MODEL C – pp. 335–349

150 P (bar)

200

346

Solubility in Supercritical Carbon Dioxide

[E-22]

Ethyl oleate (C20H38O2; MW=310.51) 1)

1)

2)

6

y x 10

6

y x 10 T (K) P (bar) S (g/L) 12000 298.2 69 32.0 6113 8283 103 48.5 9458 138 58.3 9888 172 63.1 0 313.2 69 0.0 8000 897 83 2.0 5302 103 24.5 6097 125 31.6 7286 138 39.3 4000 9193 152 51.3 10054 172 58.1 0 328.2 69 0.0 601 103 1.5 0 4552 138 19.7 50 6068 144 27.3 7670 152 35.9 8308 172 41.9 1: Obtained by digitizing the graph in the original article. 2: Calculated from S. Synonyms: (Z)-9-Octadecenoic acid ethyl ester; Oleic acid ethyl ester Source: Liang, J. H.; Yeh, A. I. J. Am. Oil Chem. Soc. (1991), 68(9), 687-692.

298.2 K 313.2 K 328.2 K

100

150 P (bar)

Ethyl oleate (C20H38O2; MW=310.51)

[E-23]

6

T (K) P (bar) y x 10 313 90 600 95 2800 100 5070 110 10700 120 18300 21500 130 1: Obtained by digitizing the graph in the original article. Synonyms: Oleic acid ethyl ester; (Z)-9-Octadecenoic acid ethyl ester Source: Liong, K.; Foster. N.; Ting, S. Ind. Eng. Chem. Res. (1992), 31(1), 400-404.

25000 6

1)

y x 10

1)

200

12500

0 80

CAT4240—CHAPTER 5—31/10/2006—18:47—KADAMBADI—XML MODEL C – pp. 335–349

110 P (bar)

140

Solubility Data E

347

[E-24]

Ethyl palmitate (C18H36O2; MW=284.48) 6

y x 106

y x 10 T (K) P (bar) 313.15 91.0 6000 92.0 9000 92.1 7000 92.9 9000 94.1 10000 100.8 13000 106.4 15000 323.15 109.7 6000 111.4 7000 113.1 9000 115.4 9000 118.1 10000 125.2 13000 131.6 15000 333.15 127.5 6000 127.8 7000 131.4 9000 135.2 9000 139.0 10000 148.1 13000 156.2 15000 Synonyms: Ethyl hexadecanoate; Palmitic acid ethyl ester Source: Crampon, C.; Charbit, G.; Neau, E. J. Supercrit. Fluids (1999), 16(1), 11-20.

15000

10000 313.15 K 323.15 K 333.15 K

5000

80

130 P (bar)

[E-25]

Ethyl palmitate (C18H36O2; MW=284.48) 1)

1)

T (K) P (bar) S (g/L)

2)

y x 10

180

6

20000 4370 69 20.9 9290 103 49.9 13200 138 75.1 14500 172 84.9 1670 313.2 83 3.4 6050 103 25.6 10000 8610 125 41.0 11800 138 58.5 17100 152 88.0 17000 172 90.6 1500 328.2 103 3.4 0 4110 138 16.2 50 6010 144 24.8 9160 152 39.3 11800 172 54.7 1: Obtained by digitizing the graph in the original article. 2: Calculated from S. Synonyms: Ethyl hexadecanoate; Palmitic acid ethyl ester Source : Liang, J. H.; Yeh, A. I. J. Am. Oil Chem. Soc. (1991), 68(9), 687-692.

298.2 K 313.2 K 328.2 K

y x 10

6

298.2

CAT4240—CHAPTER 5—31/10/2006—18:47—KADAMBADI—XML MODEL C – pp. 335–349

125 P (bar)

200

348

Solubility in Supercritical Carbon Dioxide

Ethyl stearate (C20H40O2; MW=312.53)

[E-26]

6000

313 K 323 K 333 K

6

4000 y x 10

T (K) P (bar) 313.15 94.7 95.1 96.1 99.4 99.4 101.2 101.2 101.8 102.1 109.0 109.4 323.15 115.8 117.4 119.4 124.0 125.4 125.7 129.0 129.2 136.2 136.5 333.15 133.4 137.3 139.9 144.2 145.5 146.9 149.7 149.8 159.3 159.6

y x 106 1400 1600 2000 2200 2200 2300 2300 3000 3000 5000 5000 1400 1600 2000 2200 2300 2300 3000 3000 5000 5000 1400 1600 2000 2300 2200 2300 3000 3000 5000 5000

2000

0 60

100

140

180

P (bar)

Synonyms: Ethyl octadecanoate; Stearic acid ethyl ester Source : Crampon, C.; Charbit, G.; Neau, E. J. Supercrit. Fluids (1999), 16(1), 11-20. 1)

Eucalyptus leaves extract 283.15 288.15 293.15 298.15

66.7 66.7 78.5 66.7 66.7

W (g/kg) 2.03 3.95 4.94 4.07 3.25

w x 10

2230 3930 4920 4050 3240

6000 6

P (bar)

6

w x 10

T (K)

[E-27] 2)

1: The botanical name is Eucalyptus tereticornis. 2: Calculated from W. Source: Rodrigues, V. M.; Sousa E. M. B. D.; Monteiro, A. R.; Chiavone-Filho, O.; Marques, M. O. M.; Meireles, M. A. A. J. Supercrit. Fluids (2002), 22(1), 21-36.

283.15 K 288.15 K 293.15 K 298.15 K

3000

0 65

CAT4240—CHAPTER 5—31/10/2006—18:47—KADAMBADI—XML MODEL C – pp. 335–349

70

75 P (bar)

80

Solubility Data E

349

Eugenol (C10H12O2; MW=164.20)

[E-28]

6

308.15 K 318.15 K 328.15 K

y x 10

6

y x 10 T (K) P (bar) 308.15 14.8 1200 20000 28.3 1300 42.5 1300 56.2 1300 70.5 1400 84.1 16300 318.15 14.8 1200 28.3 1300 10000 42.1 1400 55.5 1400 71.1 1400 83.6 1500 97.6 4100 328.15 56.5 1400 0 70.7 1500 0 84.2 1500 97.1 1500 112.4 3900 125.1 9600 Synonyms: 2-Methoxy-4-(2-propenyl)phenol; 4-Allyl2-methoxyphenol Source: Cheng, K.-W.; Kuo, S.-J.; Tang, M.; Chen, Y.-P. J. Supercrit. Fluids (2000), 18(2), 87-99.

50

100 P (bar)

Ewe's milk fat T (K) P1) (bar) S1) (g/L)

150

[E-29] 2)

w x 10

6

14000 90 0.00 0 105 0.24 360 115 1.41 2000 149 6.12 7780 187 8.70 10400 7000 247 9.10 10300 300 9.06 9840 323.15 90 0.00 0 105 2.12 4670 115 5.53 9880 0 149 8.59 12100 187 8.82 11300 50 247 9.10 10800 300 9.30 10600 1: Obtained by digitizing the graph in the original article. 2: Calculated from S. Source: Gonzalez Hierro, M. T.; Ruiz-Sala, P.; Alonso, L.; Santa-Maria, G. Z. Lebensm. Unters. Forsch. (1995), 200(4), 297-300. w x 10

6

313.15

313.15 K 323.15 K

150

CAT4240—CHAPTER 5—31/10/2006—18:47—KADAMBADI—XML MODEL C – pp. 335–349

250 P (bar)

350

6

Solubility Data F

Fenchone (C10H16O; MW=152.23)

323

333

P (bar) 70.4 75.0 77.6 78.5 80.0 73.8 78.3 84.9 88.7 92.0 95.3 98.7 79.8 85.5 89.9 96.0 103.1 107.6 112.0 113.3 115.0

y x 106 300 400 500 1000 2100 400 800 1700 1900 3400 4400 19200 500 1000 2200 2100 3500 4400 6800 10300 16900

20000

y x 106

T (K) 313

[F-1]

313 K 323 K 333 K

10000

0 60

80

100

120

P (bar)

Synonyms: 1,3,3-Trimethyl-2-norbornanone; 1,3,3-Trimethylnorcamphor Source: Akgun, M.; Akgun, N. A.; Dincer, S. J. Supercrit. Fluids (1999), 15, 117-125.

Ferrocene (C10H10Fe; FW=186.03) P (bar) 134 245 335

yx

1080 3920 4830

Synonyms: Bis(η5-cyclopentadienyl) iron; Iron bis(cyclopentadienide) Source: Burford, M. D.; Clifford, A. A.; Bartle, K. D.; Cowey, C. M.; Smart, N. G. J. Chromatogr. A (1996), 738(2), 241252.

6000 y x 106

T (K) 333

[F-2]

106

3000 0 100

200 300 P (bar)

400

351

CAT4240—CHAPTER 6—1/11/2006—14:18—MUGUNTHAN—XML MODEL C – pp. 351–380

352

Solubility in Supercritical Carbon Dioxide

[F-3]

Ferrocene (C10H10Fe; FW=186.03) y2)

106

(g/L) x T (K) P (bar) 313.15 134.1 4.77 1490 244.4 9.13 2460 335.5 12.10 3070 323.15 134.1 3.80 1370 244.4 11.10 3150 335.5 13.30 3510 333.15 134.1 2.42 1070 244.4 13.00 3910 335.5 17.50 4810 343.15 134.1 1.38 761 244.4 14.90 4790 335.5 20.70 5950 1: The solubility was directly measured by SFE. 2: Calculated from S. Synonyms: Bis(η5-cyclopentadienyl)iron; Iron bis(cyclopentadienide) Source: Cowey, C. M.; Bartle, K. D.; Burford, M. D.; Clifford, A. A.; Zhu, S.; Smart, N. G.; Tinker, N. D. J. Chem. Eng. Data (1995), 40(6), 1217-1221.

6000 y x 106

S1)

313.15 K 323.15 K 333.15 K 343.15 K

4000

2000

0 100

200

300

P (bar)

Ferrocene (C10H10Fe; FW=186.03)

323.15

333.15

P (bar) 97.5 117.3 134.1 153.9 183.9 214.1 244.4 274.9 305.0 335.5 366.3 97.5 117.3 134.1 153.9 183.9 214.1 244.4 274.9 305.0 335.5 366.3 97.5 117.3 134.1

(g/L)

2.070 3.860 5.040 6.290 7.820 8.389 10.300 11.600 13.100 12.700 14.800 0.582 2.130 3.840 5.470 7.500 9.270 10.700 12.300 13.600 18.400 20.600 0.301 1.060 2.290

y2)

x

[F-4]

106

799 1280 1580 1880 2240 2320 2770 3050 3079 3220 3700 381 881 1380 1820 2310 2730 3040 3390 3660 4850 5330 256 599 1010

8000

313.15 K 323.15 K 333.15 K 343.15 K

6000

y x 106

T (K) 313.15

S1)

4000

2000

0 0

100

CAT4240—CHAPTER 6—1/11/2006—14:18—MUGUNTHAN—XML MODEL C – pp. 351–380

200 P (bar)

300

400

Solubility Data F

353

153.9 3.950 1500 183.9 6.450 2180 214.1 8.580 2710 244.4 10.700 3220 274.9 13.000 3780 305.0 14.800 4180 335.5 18.800 5170 366.3 22.600 6080 343.15 97.5 0.222 220 117.3 0.594 421 134.1 1.410 778 153.9 2.750 1230 183.9 5.360 2020 214.1 8.340 2860 244.4 11.200 3610 274.9 14.800 4550 305.0 17.400 5160 335.5 20.500 5900 366.3 24.000 6730 1: The solubility was measured by supercritical fluid chromatography. 2: Calculated from S. Synonyms: Bis(η5-cyclopentadienyl)iron; Iron bis(cyclopentadienide) Source: Cowey, C. M.; Bartle, K. D.; Burford, M. D.; Clifford, A. A.; Zhu, S.; Smart, N. G.; Tinker, N. D. J. Chem. Eng. Data (1995), 40(6), 1217-1221.

Ferrocene (C10H10Fe; FW=186.03)

1600

y x 106

P1) (bar) y1) x 106 T (K) 45 313.15 71 75 72 72 78 108 80 153 83 171 83 84 243 387 86 342 86 476 87 602 89 701 92 773 93 890 95 854 96 1030 103 1160 108 1220 110 1290 115

[F-5]

800

0 50

CAT4240—CHAPTER 6—1/11/2006—14:18—MUGUNTHAN—XML MODEL C – pp. 351–380

100 P (bar)

150

354

Solubility in Supercritical Carbon Dioxide

122 123 131 132 138

1430 1380 1440 1520 1510

1: Obtained by digitizing the graph in the original article. Synonyms: Bis(η5-cyclopentadienyl)iron; Iron bis(cyclopentadienide) Source: Hansen, B. N.; Lagalante, A. F.; Sievers, R. E.; Bruno, T. J. Rev. Sci. Instr. (1994), 65(6), 2112-2114.

Ferulic acid (C10H10O4; MW=194.19)

[F-6]

106

yx P (bar) 0.82 100 3.67 150 6.55 200 8.83 250 11.28 300 13.88 350 15.13 400 16.93 450 18.81 500 0.11 323 100 4.03 150 8.44 200 13.43 250 15.60 300 18.60 350 20.84 400 23.92 450 26.61 500 0.07 333 100 3.83 150 10.85 200 18.23 250 24.48 300 31.47 350 36.83 400 40.01 450 500 43.33 Synonyms: 3-(4-Hydroxy-3-methoxyphenyl)acrylic acid; 4-Hydroxy-3-methoxycinnamic acid Source: Murga, R.; Sanz, M. T.; Beltran, S.; Cabezas, J. L. J. Supercrit. Fluids (2003), 27(3), 239-245.

y x 10

6

T (K) 313

50 313 K 323 K 333 K

40 30 20 10 0 0

200

CAT4240—CHAPTER 6—1/11/2006—14:18—MUGUNTHAN—XML MODEL C – pp. 351–380

400 P (bar)

600

Solubility Data F

355

Ferulic acid (C10H10O4; MW=194.19) T (K)

P (bar)

5

w x 10

[F-7]

6

y x 10

301 K 313 K 323 K 333 K

10 y x 10

6

120 0.94 2.13 150 1.09 2.47 200 1.42 3.22 313.15 120 0.86 1.95 150 1.19 2.70 200 1.88 4.25 250 2.38 5.40 280 2.74 6.21 323.15 120 0.68 1.55 150 1.54 3.49 200 2.37 5.38 250 3.77 8.53 280 4.35 9.85 333.15 150 1.42 3.22 200 2.99 6.77 220 3.52 7.98 250 4.33 9.81 280 5.22 11.80 Synonyms: 3-(4-Hydroxy-3-methoxyphenyl)acrylic acid; 4-Hydroxy-3-methoxycinnamic acid Source: Sovova, H. J. Chem. Eng. Data (2001), 46(5), 1255-1257.

15

301.15

5

0 100

200

300

P (bar)

Ferulic acid (C10H10O4; MW=194.19)

120

150 200

250

280

1)

Ethanol (wt%) 0.29 0.64 1.00 3.57 0.34 0.74 3.00 0.45 0.86 1.85 2.45 0.40 0.42 1.00 2.03 0.46 1.20 1.69

5

w x 10

2.58 4.01 6.32 26.60 3.65 6.07 24.90 6.41 8.32 31.30 22.60 8.82 7.17 15.10 26.10 12.00 18.10 24.50

2)

6

y x 10

5.85 9.09 14.32 60.30 8.27 13.76 56.44 14.53 18.86 70.95 51.23 19.99 16.25 34.23 59.16 27.20 41.03 55.54

100 313.15 K

80 6

313.15

P (bar)

y x 10

T (K)

[F-8]

60 40

120 bar 150 bar 200 bar 250 bar 280 bar

20 0

0

1

CAT4240—CHAPTER 6—1/11/2006—14:18—MUGUNTHAN—XML MODEL C – pp. 351–380

2 Ethanol (wt%)

3

4

356

250

280 333.15

120

150 200 250

280

3.42 6.69 58.94 6.98 15.00 45.79 19.17 21.53 82.06 55.76 18.31 18.90 35.59 57.35 62.34 24.48 45.79 64.83 2.29 3.85 37.63 7.12 12.22 35.59 33.77 59.16 56.67 21.33 23.80 41.48 60.07 31.28 47.15 76.40

100 323.15 K

80 6

200

1.51 2.95 26.00 3.08 6.62 20.20 8.46 9.50 36.20 24.60 8.08 8.34 15.70 25.30 27.50 10.80 20.20 28.60 1.01 1.70 16.60 3.14 5.39 15.70 14.90 26.10 25.00 9.41 10.50 18.30 26.50 13.80 20.80 33.70

y x 10

150

0.28 0.61 3.35 0.33 0.71 2.78 0.48 0.82 1.97 2.30 0.38 0.40 0.96 1.54 1.91 0.44 1.12 1.58 0.27 0.58 3.15 0.31 0.67 2.61 0.78 1.74 2.16 0.36 0.37 0.91 1.80 0.42 1.06 1.49

60 40

120 bar 150 bar 200 bar 250 bar 280 bar

20 0

0

1

2 3 Ethanol (wt%)

4

100 333.15 K

80 6

120

y x 10

323.15

Solubility in Supercritical Carbon Dioxide

60

120 bar 150 bar 200 bar 250 bar 280 bar

40 20 0

0

1: Cosolvent in CO2. 2: Calculated from w on a cosolvent-free basis. Synonyms: 3-(4-Hydroxy-3-methoxyphenyl)acrylic acid; 4-Hydroxy-3-methoxycinnamic acid Source: Sovova, H. J. Chem. Eng. Data (2001), 46(5), 1255-1257.

CAT4240—CHAPTER 6—1/11/2006—14:18—MUGUNTHAN—XML MODEL C – pp. 351–380

1

2 3 Ethanol (wt%)

4

Solubility Data F

357

Fish liver oil (Cod)1) W (g/kg CO2)

P (bar)

8000

w2) x 106

200 3.66 3650 225 4.79 4770 250 5.94 5910 333 200 1.60 1600 225 2.54 2530 250 3.92 3910 275 5.27 5240 300 7.08 7030 1: The scientific name of cod is Gadus callarias . 2: Calculated from W. Source: Catchpole, O. J.; Grey, J. B.; Noermark, K. A. J. Chem. Eng. Data (1998), 43(6), 1091-1095.

6

313

313 K 333 K

w x 10

T (K)

[F-9]

4000

0 150

200

250 P (bar)

300

Fish liver oil (Cod)1) T (K)

P (bar)

Ethanol2) (wt%)

350

[F-10]

W (g/kg CO2)

w3) x 106

200 bar 250 bar 275 bar 300 bar

6

333

30000

w x 10

200 4.86 4.81 4570 200 7.75 9.07 8350 200 10.89 14.91 13300 333 250 4.16 11.58 11000 250 7.27 18.65 17100 250 9.92 27.95 24800 333 275 4.31 15.70 14800 275 6.92 21.15 19400 275 9.61 32.60 28900 333 300 4.25 16.81 15900 300 7.17 27.12 24700 300 10.20 42.35 37000 1: The scientific name of cod is Gadus callarias . 2: Cosolvent in CO2 on a solute-free basis. 3: Calculated from W and the amount of cosolvent. Source: Catchpole, O. J.; Grey, J. B.; Noermark, K. A. J. Chem. Eng. Data (1998), 43(6), 1091-1095.

45000

15000

0

0

CAT4240—CHAPTER 6—1/11/2006—14:19—MUGUNTHAN—XML MODEL C – pp. 351–380

5 10 Ethanol (wt%)

15

358

Solubility in Supercritical Carbon Dioxide

Fish liver oil (Orange Roughy fish)1) T (K)

Ethanol (wt%)

2)

W (g/kg CO2)

80000

w3) x 106

0.00 5.79 5760 4.99 14.43 13600 7.91 22.79 20700 11.01 35.36 30900 333 260 0.00 12.24 12100 5.00 26.23 24400 8.07 40.90 36500 11.17 63.41 54000 333 300 0.00 17.10 16800 4.58 32.44 30100 7.66 50.17 44500 10.50 79.91 67400 1: The scientific name of this fish is Hoplostethus atlanticus. 2: Cosolvent in CO2 on a solute-free basis. 3: Calculated from W and the amount of cosolvent. Source: Catchpole, O. J.; Grey, J. B.; Noermark, K. A. J. Chem. Eng. Data (1998), 43(6), 1091-1095

200 bar 260 bar 300 bar

200

w x 10

6

333

P (bar)

[F-11]

40000

0

0

5

10

Ethanol (wt%)

Fish liver oil (Spiny Dogfish)1)

200 225 250 275 300 200

2)

W (g/kg CO2)

3)

6000

6

w x 10

6

Ethanol (wt%)

0 1.40 1400 3000 0 2.02 2010 0 2.95 2940 0 4.09 4070 0 0 5.40 5370 150 333 4.51 3.97 3780 7.53 7.21 6660 9.95 11.30 10200 40000 250 4.26 7.99 7600 7.29 13.53 12500 9.95 20.69 18500 275 4.37 9.97 9460 7.11 16.58 15200 9.72 24.68 22000 20000 300 3.98 12.25 11600 6.56 18.58 17100 9.53 28.05 25000 1: The scientific name of this fish is Squalus acanthius . 0 2: Cosolvent in CO2 on a solute-free basis. 0 3: Calculated from W and the amount of cosolvent. Source: Catchpole, O. J.; Grey, J. B.; Noermark, K. A. J. Chem. Eng. Data (1998), 43(6), 1091-1095.

w x 10

6

333

P (bar)

[F-12]

w x 10

T (K)

15

CAT4240—CHAPTER 6—1/11/2006—14:19—MUGUNTHAN—XML MODEL C – pp. 351–380

200

250

300

350

P (bar)

200 bar 250 bar 275 bar 300 bar

5 10 Ethanol (wt%)

15

Solubility Data F

359

[F-13]

Fish liver oil (Spiny Dogfish + Deep Sea Shark)

333

Ethanol2) (wt%)

W (g/kg CO2)

Spiny Dogfish 0 3.0 4 8.3 7 13.8 10 21.0 Deep Sea Shark 250 0 16.7 4 28.5 8 42.3 11 55.9 250

4)

60000

6

w x 10

3000 7920 12700 18700

Spiny Dogfish Deep Sea shark

6

333

1)

P (bar)

w x 10

T (K)

1,3)

30000

16400 26700 37700 47900

0

1: Obtained by digitizing the graph in the original article. 2: Cosolvent on a solute-free basis. 3: Mass solubility in CO2 (cosolvent-free basis). 4: Calculated from W and the amount of cosolvent. Source: Catchpole, O. J.; Grey, J. B.; Noermark, K. A. J. Supercrit. Fluids (2000), 19(1), 25-37.

0

5

10

Ethanol (wt%)

Fish oil (Sand Eel)1)

353.2

P (bar) 53.3 100.6 100.9 151.0 151.2 202.3 203.1 255.0 255.2 255.5 345.0 352.0 450.4 452.0 552.1 552.4 553.5 554.2 102.0 106.5 152.0 201.1 250.6 251.8

wx

0 730 780 1700 1700 4000 3800 7000 7600 6400 10700 10700 15800 14600 21900 19400 18900 17700 840 0 0 380 2500 1800

100000

w x 106

T (K) 313.2

[F-14] 106

313.2 K 353.2 K 393.2 K

50000

0 0

200

CAT4240—CHAPTER 6—1/11/2006—14:19—MUGUNTHAN—XML MODEL C – pp. 351–380

400 P (bar)

600

800

360

Solubility in Supercritical Carbon Dioxide

302.3 5000 302.6 4400 350.4 9000 350.8 8800 400.5 14000 403.0 14500 450.4 20500 451.0 22100 501.0 28200 501.7 28100 550.6 34600 550.8 35800 600.2 44700 600.3 45600 650.4 53900 650.8 55100 393.2 351.0 5300 404.9 13300 452.2 20000 452.2 19800 503.6 32000 645.2 92500 1: Fish oil from sand eel (Ammodytes lancea). Source: Borch-Jensen, C.; Mollerup, J. Fluid Phase Equil. (1997), 138(1-2), 179-211.

Fish oil ethyl esters (EE-1)1)

333.2

343.2

353.2

P (bar) w x 106 90 32900 100 82900 120 10600 130 25800 140 42500 150 88600 130 9000 140 23800 150 36300 160 54400 170 69000 150 7800 160 18200 170 26100 180 40700 190 70200 200 93700

100000

w x 106

T (K) 313.2

[F-15]

50000 313.2 K 333.2 K 343.2 K 353.2 K

0 50

100

1: Artificial mixture of high hydrocarbon ethyl esters, ranging from C14 to C22. Source: Riha, V.; Brunner, G. J. Supercrit. Fluids (1999), 15(1), 33-50.

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150 P (bar)

200

250

Solubility Data F

361

Fish oil ethyl esters (EE-2)1) 60000 w x 106

T (K) P (bar) w x 106 313.2 90 9400 100 48300 333.2 120 6400 140 29200

[F-16]

1: Artificial mixture of high hydrocarbon ethyl esters, ranging from C14 to C22. Source: Riha, V.; Brunner, G. J. Supercrit. Fluids (1999), 15(1), 33-50.

30000

313.2 K 333.2 K

0 50

100 P (bar)

150

[F-17]

Fish oil ethyl esters (EE-3)1)

333.2

343.2

353.2

P (bar) w x 90 19300 100 66500 110 113000 120 9800 130 20000 140 37300 150 64600 160 107600 130 9300 140 16200 150 24100 160 42800 170 73000 150 13400 160 18200 170 30400 180 45800 190 79800

120000

w x 106

T (K) 313.2

106

313 K 333 K 343 K 353 K

80000

40000

0 50

100

1: Artificial mixture of high hydrocarbon ethyl esters, ranging from C14 to C22. Source: Riha, V.; Brunner, G. J. Supercrit. Fluids (1999), 15(1), 33-50.

CAT4240—CHAPTER 6—1/11/2006—14:19—MUGUNTHAN—XML MODEL C – pp. 351–380

150 P (bar)

200

362

Solubility in Supercritical Carbon Dioxide

Fish oil ethyl esters (EE-4)1)

333.2

343.2

P (bar) 90 100 110 115 120 125 130 135 120 130 140 145 150 160 170 180 140 145 150 160 170 180 190 200

w x 106 6300 33800 50600 74500 86900 121900 144700 175600 1600 12200 21800 36500 41500 61300 86000 117100 8800 11900 18400 26200 37000 53500 78100 97800

180000 313.2 K 333.2 K 343.2 K

120000 w x 106

T (K) 313.2

[F-18]

60000

0 50

100

150

200

P (bar)

1: Artificial mixture of high hydrocarbon ethyl esters, ranging from C14 to C22. Source: Riha, V.; Brunner, G. J. Supercrit. Fluids (1999), 15(1), 33-50.

Fish oil ethyl esters (EE-5)1) 313.2 333.2

P (bar) w x

100 47500 120 103400 120 9100 140 31500 160 64100

1: Artificial mixture of high hydrocarbon ethyl esters, ranging from C14 to C22. Source: Riha, V.; Brunner, G. J. Supercrit. Fluids (1999), 15(1), 33-50.

[F-19] 120000 w x 106

T (K)

106

313.2 K 333.2 K

60000

0 50

CAT4240—CHAPTER 6—1/11/2006—14:19—MUGUNTHAN—XML MODEL C – pp. 351–380

100 150 P (bar)

200

Solubility Data F

363

Fish oil ethyl esters (EE-6)1)

333.2

P(bar) w x 106 100 32000 120 81000 120 4600 140 21800 160 50700

100000 w x 106

T (K) 313.2

[F-20] 313.2 K 333.2 K

50000

1: Artificial mixture of high hydrocarbon ethyl esters, ranging from C14 to C22. Source: Riha, V.; Brunner, G. J. Supercrit. Fluids (1999), 15(1), 33-50.

0 50

100

150

Fish oil ethyl esters (EE-7)1)

333.2

[F-21]

106

P (bar) w x 100 27700 120 70700 120 4400 140 20500 160 36700

80000 w x 106

T (K) 313.2

313.2 K 333.2 K

40000 0

1: Artificial mixture of high hydrocarbon ethyl esters, ranging from C14 to C22. Source: Riha, V.; Brunner, G. J. Supercrit. Fluids (1999), 15(1), 33-50.

50

100 150 P (bar)

Fish oil ethyl esters (EE-8)1)

333.2

P (bar) w x 100 29900 120 67700 120 7700 140 21700 160 49100

1: Artificial mixture of high hydrocarbon ethyl esters, ranging from C14 to C22. Source: Riha, V.; Brunner, G. J. Supercrit. Fluids (1999), 15(1), 33-50.

200

[F-22]

106

80000 w x 106

T (K) 313.2

200

P (bar)

313 K 333 K

40000

0 50

100 150 P (bar)

CAT4240—CHAPTER 6—1/11/2006—14:19—MUGUNTHAN—XML MODEL C – pp. 351–380

200

364

Solubility in Supercritical Carbon Dioxide

Fish oil ethyl esters (EE-9)1)

333.2

P (bar) w x 106 100 24200 120 63100 120 4800 140 17900 160 43800

80000 w x 106

T (K) 313.2

[F-23]

1: Artificial mixture of high hydrocarbon ethyl esters, ranging from C14 to C22. Source: Riha, V.; Brunner, G. J. Supercrit. Fluids (1999), 15(1), 33-50.

313.2 K 333.2 K

40000

0 50

100

150 P (bar)

Fish oil ethyl esters (EE-10)1) 313.2

333.2

343.2

353.2

P (bar) w x 90 100 110 120 130 140 120 130 140 150 160 170 180 190 130 140 150 160 170 180 190 200 210 150 160 170 180 190 200 210 220 230

[F-24]

106

11100 25800 44400 65200 93700 132900 4900 10300 17600 26900 37300 70000 116600 162200 2800 7400 9700 23600 26600 36600 52600 75100 101300 6500 9500 17100 24000 32500 47500 64600 89500 107600

200000

313.2 K 333.2 K 343.2 K 353.2 K

150000 w x 106

T (K)

200

100000

50000

0 50

100

1: Artificial mixture of high hydrocarbon ethyl esters, ranging from C14 to C22. Source: Riha, V.; Brunner, G. J. Supercrit. Fluids (1999), 15(1), 33-50.

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150 P (bar)

200

250

Solubility Data F

365

Fish oil ethyl esters (EE-11)1)

333.2

P (bar) 100 120 150 120 140 160 200

w x 106 17900 41600 84000 2600 11500 28200 79600

100000 w x 106

T (K) 313.2

[F-25] 313.2 K 333.2 K

50000

0

1: Artificial mixture of high hydrocarbon ethyl esters, ranging from C14 to C22. Source: Riha, V.; Brunner, G. J. Supercrit. Fluids (1999), 15(1), 33-50.

50

100

150 P (bar)

Fish oil ethyl esters (EE-12)1)

333.2

343.2

P (bar) 90 100 110 120 130 140 150 160 170 120 130 140 150 160 170 180 190 200 210 130 140 150 160 170 180 190 200 210 220 230

wx

[F-26]

106

7000 18600 31100 43100 56200 74600 95900 121300 160000 3100 6300 12400 22500 30800 41800 54500 67700 92100 121100 2900 6400 12800 15000 22000 28800 36800 52200 71200 87800 110700

180000 313.2 K 333.2 K 343.2 K 353.2 K

120000 w x 106

T (K) 313.2

200

60000

0 50

CAT4240—CHAPTER 6—1/11/2006—14:19—MUGUNTHAN—XML MODEL C – pp. 351–380

150 P (bar)

250

366

Solubility in Supercritical Carbon Dioxide

353.2

150 160 170 180 190 200 210 220 230 240 250

3000 5100 7300 12300 18500 30300 38400 51800 58800 67300 93800

1: Artificial mixture of high hydrocarbon ethyl esters, ranging from C14 to C22. Source: Riha, V.; Brunner, G. J. Supercrit. Fluids (1999), 15(1), 33-50.

Fish oil ethyl esters (EE-13)1) 313.2

333.2

343.2

P (bar) 90 100 110 120 130 140 150 160 120 130 140 150 160 170 180 190 200 210 130 140 150 160 170 180 190 200 210 220 230 240

wx

8300 19400 31000 55400 56700 68700 101300 130800 2500 7100 13700 19700 28400 39100 52000 71200 88300 113100 2300 5600 8400 12700 20400 29400 37700 48200 59700 73800 113000 129700

150000

313.2 K 333.2 K 343.2 K 353.2 K

100000 w x 106

T (K)

[F-27]

106

50000

0 50

100

CAT4240—CHAPTER 6—1/11/2006—14:19—MUGUNTHAN—XML MODEL C – pp. 351–380

150 P (bar)

200

250

Solubility Data F

353.2

367

150 5000 160 7700 170 13000 180 18500 190 22200 200 31000 210 40100 220 48600 230 64000 240 83500 250 112900

1: Artificial mixture of high hydrocarbon ethyl esters, ranging from C14 to C22. Source: Riha, V.; Brunner, G. J. Supercrit. Fluids (1999), 15(1), 33-50.

Fish oil fatty acid ethyl ester (FAEE)

[F-28]

106

150000

w x 106

wx T (K) P (bar) From Original FAEE 343.15 0.0 54500 11.3 78000 31.5 103000 72.0 119000 122.7 130000 195.5 136000 From Urea Fractionated 343.15 5.7 54500 31.5 78000 56.8 103000 84.6 119000 105.2 130000 159.1 136000 From Omega 3 Concentrate 343.15 0.0 54500 11.3 78000 26.7 103000 94.6 130000 101.0 130000 139.9 139000

100000

Original FAEE Urea Fractionated Omega 3 Conc

50000 0

50

Source: Borch-Jensen, C.; Henriksen, O.; Mollerup, J. ACS Symp. Series (1997), 670 (Supercrit. Fluids), 90-100.

CAT4240—CHAPTER 6—1/11/2006—14:19—MUGUNTHAN—XML MODEL C – pp. 351–380

100 P (bar)

150

200

368

Solubility in Supercritical Carbon Dioxide

Fish oil fatty acid ethyl ester, Urea fractionated 700 18900 42600 71700 121500 163300 1800 11800 23800 43900 61900 124200

[F-29]

180000

6

wx

313.2 K 343.2 K

120000

w x 10

T (K) P (bar) 313.2 80.2 90.0 100.8 125.5 150.1 175.4 343.2 100.8 125.8 150.0 175.6 199.5 225.7

106

60000

0 50

Source: Borch-Jensen, C.; Staby, A.; Mollerup, J. M. Ind. Eng. Chem. Res. (1994), 33(6), 1574-1579.

100

150

200

250

P (bar)

[F-30]

Flavone (C15H10O2; MW= 222.24) 1000

T(K) P1) (bar) S1) (mg/Nl2)) y3) x 106

80 0.06 6 85 0.21 21 90 0.60 60 500 100 2.26 226 150 5.95 596 200 8.24 825 1: Obtained by digitizing the graph in the 0 original article. 50 2: "Nl" means "Normliter," which is one liter at 273.15 K and 1 atm. 3: Calculated from S. Synonym: 2-Phenyl-4-chromone Source: Stahl, E.; Schilz, W. Talanta (1979), 26, 675-679.

y x 106

313.15

CAT4240—CHAPTER 6—1/11/2006—14:19—MUGUNTHAN—XML MODEL C – pp. 351–380

100

150 P (bar)

200

Solubility Data F

369

Flavone (C15H10O2; MW=222.24) 600

y x 106

yx P (bar) 91 107 101 233 152 359 203 422 253 462 318.2 91 35 101 165 152 473 203 536 253 561 Synonym: 2-Phenyl-4-chromone Source: Uchiyama, H.; Mishima, K.; Oka, S.; Ezawa, M.; Ide, M.; Takai, T.; Park, P. W. J. Chem. Eng. Data (1997), 42(3), 570-573. T (K) 308.2

[F-31]

106

308.2 K 318.2 K

400

200

0 0

100

200 P (bar)

Florfenicol (C12H14Cl2FNO4S; MW=358.21)

[F-32]

y x 106 0.21 0.57 1.02 1.78 2.09 2.41 0.17 2.94 4.52 4.90 5.56 5.89 6.36 7.07 7.69

9

313.15 K 333.15 K

6 y x 106

T (K) P (bar) 313.15 178 221 292 358 406 465 333.15 117 144 184 209 257 293 367 427 490

300

3

0 0

200

Synonyms: Aquafen; 2,2-Dichloro-N-[(1S, 2R)-1(fluoromethyl)-2-hydroxy-2-[4-(methylsulfonyl) phenyl]ethyl]acetamide Source: Li, S.; Maxwell, R. J.; Shadwell, R. J. Fluid Phase Equil. (2002), 198(1), 67-80.

CAT4240—CHAPTER 6—1/11/2006—14:19—MUGUNTHAN—XML MODEL C – pp. 351–380

400 P (bar)

600

370

Solubility in Supercritical Carbon Dioxide

Fluoranthene (C16H10; MW=202.25)

[F-33]

106

1000 308.15 K 318.15 K 328.15 K

750 y x 106

P (bar) y x 89 113 98 183 109 241 121 310 135 343 150 388 160 416 173 448 175 455 198 491 200 517 247 572 318.15 86 9 90 14 100 59 110 143 120 235 136 359 153 433 176 524 198 603 249 779 328.15 100 17 121 99 140 258 159 508 180 609 209 930 Synonym: Benzo[j, k]fluorene Source: Barna, L.; Blanchard, J.-M.; Rauzy, E.; Berro, C. J. Chem. Eng. Data (1996), 41(6), 14661469. T (K) 308.15

500

250

0 50

Fluoranthene (C16H10; MW=202.25) T (K) P (bar) 308.15 121.6 152.0 182.4 212.8 243.2 273.6 304.0 334.4 354.6 318.15 121.6 152.0 182.4

yx

106 236 284 328 363 399 423 465 468 497 214 298 378

CAT4240—CHAPTER 6—1/11/2006—14:19—MUGUNTHAN—XML MODEL C – pp. 351–380

150 P (bar)

250

[F-34]

Solubility Data F

371

1500

y x 106

212.8 443 243.2 505 273.6 549 304.0 605 334.4 644 354.6 662 328.15 121.6 186 152.0 300 182.4 416 212.8 544 243.2 628 273.6 715 304.0 784 334.4 864 354.6 923 338.15 121.6 104 152.0 263 182.4 433 212.8 615 243.2 735 273.6 1013 304.0 1021 334.4 1126 354.6 1178 348.15 121.6 127 152.0 297 182.4 559 212.8 711 243.2 934 273.6 1124 304.0 1316 334.4 1446 354.6 1515 Synonym: Benzo[ j, k]fluorene Source: Yamini, Y.; Bahramifar, N. J. Chem. Eng. Data (2000), 45(1), 53-56.

308.15 K 318.15 K 328.15 K 338.15 K 348.15 K

1000

500

0 100

Fluoranthene (C16H10; MW=202.25) Cosolvent3) T1) (K) 295.2

308.2

P2) (bar)

(mol%)

y4) x 106

71 92 145 226 316 91 111 139

0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0

2 11 95 303 357 6 16 21

CAT4240—CHAPTER 6—1/11/2006—14:19—MUGUNTHAN—XML MODEL C – pp. 351–380

200

300 P (bar)

400

[F-35]

372

Solubility in Supercritical Carbon Dioxide

295.2

65 84 136 258 402 60 69 122 189 298 62 84 132 236 364

0.0 0.0 0.0 Methanol 3.2 3.2 3.2 3.2 3.2 Hexane 3.2 3.2 3.2 3.2 3.2 Acetone 3.2 3.2 3.2 3.2 3.2

91 310 510 11 21 98 210 293 32 57 265 436 334 217 248 334 550 628

1500

1000

CO2 295 K CO2 308 K MeOH 295 K Hexan 295 K Aceto 295 K CO2 0.8 g/mL

y x 106

191 238 284

500

r = 0.80 g/ml 0 314 170 0.0 268 0 317 181 0.0 569 320 197 0.0 599 325 235 0.0 696 333 266 0.0 1408 345 322 0.0 1408 1: Obtained by digitizing the graph in the original article (temperatures at 0.80 g/ml). 2: Calculated from temperature and density in the source graph. 3: Cosolvent in CO2. 4: Obtained by digitizing the graph in the original article. Synonym: Benzo[ j, k]fluorene Source: Burk, R.; Kruus, P. Can. J. Chem. Eng. (1992), 70(2), 1403-1407.

100

Fluorene (C13H10; MW = 166.22) T (K) 308.2

P (bar) 78.3 79.8 80.4 80.9 82.2 82.5 83.4 84.4 85.1

yx

106 240 330 330 340 530 470 510 650 510

CAT4240—CHAPTER 6—1/11/2006—14:19—MUGUNTHAN—XML MODEL C – pp. 351–380

200

300

400

P (bar)

[F-36]

Solubility Data F

318.2

490 550 760 740 800 780 980 910 1030 910 990 1190 1220 1080 1130 1330 1370 1340 1300 1370 1500 1500 1500 1600 1620 1610 1700 1660 1820 1820 1960 1940 1930 2000 2060 2080 2280 2230 60 130 280 490 690 900 1060 1140 1280 1320 1540 1730 1910 1990 2230

4000 308.2 K 318.2 K 323.2 K 328.2 K

3000 y x 106

85.6 86.0 89.0 89.3 91.8 95.1 96.6 97.4 99.1 100.0 100.3 109.2 109.5 110.0 111.2 116.5 119.5 120.7 121.0 121.9 130.0 130.5 131.2 140.4 141.4 142.0 150.5 151.7 160.5 163.0 170.4 171.7 180.5 181.0 182.6 191.2 201.6 203.5 85.0 90.0 95.0 100.0 105.0 110.0 115.0 120.0 124.6 130.0 134.0 145.0 156.0 169.5 184.5

373

2000

1000

0 50

100

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150 P (bar)

200

250

374

Solubility in Supercritical Carbon Dioxide

323.2

328.2

198.0 216.0 224.5 232.5 244.2 254.0 89.4 92.0 95.5 100.1 102.0 105.2 105.9 106.7 108.1 108.8 110.2 114.5 118.5 121.0 125.7 129.4 130.3 135.6 137.0 140.7 145.0 146.2 151.0 156.0 156.5 160.5 166.0 167.0 168.2 174.6 181.0 181.4 193.0 195.6 202.0 212.2 219.5 228.5 85.0 90.0 95.0 100.0 105.0 110.0 115.0 120.0 125.0

2430 2710 2790 2880 2970 3120 70 110 130 260 270 430 480 490 520 500 650 730 980 920 1210 1370 1420 1440 1610 1730 1730 1800 1990 2050 2040 2180 2360 2310 2290 2520 2360 2490 2590 2600 2740 2930 2950 3110 50 80 110 180 280 430 600 820 1050

CAT4240—CHAPTER 6—1/11/2006—14:19—MUGUNTHAN—XML MODEL C – pp. 351–380

Solubility Data F

375

130.0 1230 134.2 1370 137.2 1400 145.5 1720 157.0 2060 166.1 2280 174.8 2460 186.1 2660 194.2 2800 205.5 3050 209.8 3170 214.7 3300 225.2 3480 237.0 3690 245.0 3770 Synonym: 2,2'-Methylenebiphenyl Source: Bartle, K. D.; Clifford, A. A.; Jafar, S. A. J. Chem. Eng. Data (1990), 35(3), 355-360.

Fluorene (C13H10; MW=166.22) y x 106 911 1170 1390 1480 1860 2160 2260 415 1180 1530 2260 2430 2720 11 36 428 1540 2390 3080 3870 4080 4360 69 192 985

10000

303.15 K 308.15 K 323.15 K 343.15 K

7500 y x 106

P (bar) T (K) 303.15 83.6 104.3 125.0 138.8 207.7 345.6 483.5 308.15 83.7 104.3 138.8 207.7 345.6 414.5 323.15 69.9 83.7 104.3 138.8 173.3 207.7 276.7 345.6 414.5 343.15 83.7 104.3 138.8

[F-37]

5000

2500

0 0

CAT4240—CHAPTER 6—1/11/2006—14:19—MUGUNTHAN—XML MODEL C – pp. 351–380

200 P (bar)

400

376

Solubility in Supercritical Carbon Dioxide

173.3 2540 207.7 4050 345.6 7670 414.5 8740 483.4 9180 Synonym: 2, 2'-Methylenebiphenyl Source: Johnston, K. P.; Ziger, D. H.; Eckert, C. A. Ind. Eng. Chem. Fund. (1982), 21(3), 191-197.

Fluorene (C13H10; MW=166.22)

[F-38]

106

3000 y x 106

P (bar) yx T (K) 313.1 100 1030 125 1690 150 1880 175 2030 200 2330 Synonym: 2, 2'-Methylenebiphenyl Source: Kwiatkowski, J.; Lisicki, Z.; Majewski, W. Ber. Bunsenges. Phys. Chem. (1984), 88(9), 865-869.

1500 0 50

150

250

Fluorene (C13H10; MW=166.22) T (K)

P (bar)

[F-39]

Acetone1) y x 106 (mol %)

323

y x 106

104.4 1.0 303 118.2 1.0 714 132.0 1.0 1140 145.8 1.0 3070 173.3 1.0 2630 242.3 1.0 4940 345.8 1.0 4760 118.2 2.5 1330 132.0 2.5 1540 145.8 2.5 3030 173.3 2.5 4890 242.3 2.5 8390 345.7 2.5 8760 1: Cosolvent in CO2 on a solute-free basis. Synonym: 2, 2'-Methylenebiphenyl Source: Van Alsten, J. G.; Eckert, C. A. J. Chem. Eng. Data (1993), 38(4), 605-610.

323 K (1.0%) 323 K (2.5%)

9000

6000

3000

0 0

100

CAT4240—CHAPTER 6—1/11/2006—14:19—MUGUNTHAN—XML MODEL C – pp. 351–380

200 P (bar)

300

400

Solubility Data F

377

Fluorene(1) + Anthracene (2) Mixture T (K)

P (bar)

y1 x

106

y2 x

[F-40]

106

y x 106

100 1100 25.4 125 1740 37.6 150 1840 35.2 175 2100 43.2 200 2610 50.9 Source: Kwiatkowski, J.; Lisicki, Z.; Majewski, W. Ber. Bunsenges. Phys. Chem. (1984), 88(9), 865-869.

3000

313.1

1500

Fluo Anth

0 50

150 P (bar)

250

[F-41]

9-Fluorenone (C13H8O; MW=180.20)

323

104.4 118.2 132.0 145.8 242.3 345.7 107.9 118.2 132.0 152.7 187.1 214.7 276.7

Acetone 1.0 1.0 1.0 1.0 1.0 1.0 2.5 2.5 2.5 2.5 2.5 2.5 2.5 Methanol

y x 106 265 1310 1740 2370 4900 10600 2690 2490 4070 4460 6810 7590 16400

20000

15000

y x 106

T (K)

Cosolvent1) P (bar) (mol%)

Acetone 1.0% Acetone 2.5% Methanol 1.0% Methanol 2.5%

10000

323

94.1 1.0 59 5000 104.4 1.0 99 118.2 1.0 239 132.0 1.0 1670 145.8 1.0 2190 0 242.3 1.0 3370 311.2 1.0 6710 0 380.1 1.0 9760 107.9 2.5 1130 118.2 2.5 1740 152.7 2.5 3580 214.7 2.5 6470 276.7 2.5 8440 345.7 2.5 11200 1: Cosolvent in CO2 on a solute-free basis. Synonym: Fluoren-9-one Source: Van Alsten, J. G.; Eckert, C. A. J. Chem. Eng. Data (1993), 38(4), 605-610.

100

CAT4240—CHAPTER 6—1/11/2006—14:19—MUGUNTHAN—XML MODEL C – pp. 351–380

200 P (bar)

300

400

378

Solubility in Supercritical Carbon Dioxide

5-Fluorouracil (C4H3FN2O2; MW=130.08) y1)

x P (bar) w x 110 0.46 0.156 145 0.95 0.321 175 1.39 0.470 210 2.05 0.694 328 110 0.37 0.125 145 1.36 0.460 175 2.18 0.738 210 2.86 0.968 1: Calculated from w. Synonym: 5-Fluoro-2,4-pyrimidinedione Source: Guney, O.; Akgerman, A. J. Chem. Eng. Data (2000), 45(6), 1049 1052. T (K) 308

[F-42]

106

1.2

y x 106

106

308 K 328 K

0.6

0.0 50

150 P (bar)

Flurbiprofen (C15H13FO2; MW=244.26) 303

313

323

P (bar)

S (g/L)

89 112 131 141 153 173 185 195 219 231 245 98 118 131 141 153 171 202 234 244 112 133 166

0.10 0.13 0.16 0.19 0.25 0.28 0.30 0.36 0.40 0.42 0.43 0.06 0.14 0.22 0.22 0.29 0.37 0.59 0.67 0.73 0.08 0.19 0.42

x

[F-43]

106

21.7 29.0 35.3 41.4 53.1 59.9 62.4 72.6 79.0 82.1 83.4 16.7 36.1 53.9 52.5 66.5 81.2 125.6 139.0 149.5 26.0 52.7 101.8

200 303 K 313 K 323 K

150 y x 106

T (K)

y1)

250

100

50

0 50

CAT4240—CHAPTER 6—1/11/2006—14:19—MUGUNTHAN—XML MODEL C – pp. 351–380

150 P (bar)

250

Solubility Data F

379

177 0.60 140.1 197 0.65 148.4 206 0.71 162.1 234 0.90 196.8 1: At 313 K the solubility S might have been misprinted to 0.52 and 0.55 at 202 and 234 bar, respectively, in the source table. They were recalculated based on y's in Table 1 and Figure 3 in the original article. Synonym: 2-Fluoro-a-methyl-4-biphenylacetic acid Source: Duarte, A. R. C.; Coimbra, P.; de Sousa, H. C.; Duarte, C. M. M. J. Chem. Eng. Data (2004), 49(3), 449-452.

[F-44]

Frangulin A (C21H20O9; MW=416.38)

313.15

S2) (bar) (μg/Nl3)) y4) x 106

100 0.18 0.010 489 1.09 0.058 994 1.61 0.086 1495 2.12 0.114 2000 2.04 0.109 2200 2.32 0.124 1: Calculated from temperature and density obtained by digitizing the original graph. 2: Obtained by digitizing the graph in the original article. 3: "Nl" means "Normliter," which is one liter at 273.15 K and 1 atm. 4: Calculated from S. Synonym: 3-[(6-Deoxy-a-L-mannopyranosyl)oxy]1,8-dihydroxy-6-methylanthaquinone Source: Stahl, E.; Schilz, W.; Schutz, E.; Willing, E. Angew. Chem. Int. Ed. Engl. (1978), 17, 731-738.

0.16 y x 106

T (K)

P1)

0.08

0.00 0

CAT4240—CHAPTER 6—1/11/2006—14:19—MUGUNTHAN—XML MODEL C – pp. 351–380

1000 P (bar)

2000

380

Solubility in Supercritical Carbon Dioxide

D-(—)-Fructose (C6H12O6; MW=180.16)

40 308.2 K 328.2 K 348.2 K

30 y x 106

y x 106 T (K) P (bar) 308.2 43.7 18.9 71.3 13.4 99.6 9.9 121.3 10.0 141.5 12.2 187.8 18.2 210.5 36.5 328.2 49.3 23.0 96.1 18.1 120.9 16.6 142.7 9.9 166.8 18.1 190.6 22.1 214.0 23.5 348.2 40.6 24.6 69.9 19.3 93.4 18.3 113.0 14.3 137.5 11.6 164.7 8.5 189.9 6.3 Synonym: D-Fructose; D-(−)-Levulose Source: Yau, J.-S.; Tsai, F.-N. J. Supercrit. Fluids (1994), 7(2), 129-133.

[F-45]

20 10 0 0

100 P (bar)

Fungal oil1)

[F-46] S2) (g/L) w3)x 106 1.55 1960 3.51 4170 5.16 5830 0.25 389 1.43 1980 4.56 5770 6.89 8220 1.69 2470 4.75 6310

1: Extracted from fungi (Mortierella ramanniana var. angulispora). 2: Obtained by digitizing the graph in the original article. 3: Calculated from S. Source: Sakaki, K.; Yokochi, T.; Suzuki, O.; Hakuta, T. J. Am. Oil Chem. Soc. (1990), 67(9), 558-557.

10000

w x 106

P2) (bar) T (K) 313 157 196 247 333 156 197 246 300 353 246 300

200

313 K 333 K 353 K

5000

0 100

CAT4240—CHAPTER 6—1/11/2006—14:19—MUGUNTHAN—XML MODEL C – pp. 351–380

200 P (bar)

300

7

Solubility Data G

Gallium tris(acetylacetonate) (C15H21GaO6; FW=367.05) (bar)

S1)

(mg/L)

y2)

x

106

98 0.06 0.024 196 1.21 0.201 294 3.10 0.449 1: Obtained by digitizing from the original article. 2. Calculated from S. Synonym: Tris(2,4-pentanedionato)gallium Source: Saito, N.; Ikushima, Y.; Goto, T. Bull. Chem. Soc. Japan (1990), 63(5), 1532-1534.

[G-1]

0.5 y x 106

T (K) 333

P1)

0.0 50

150

250 P (bar)

Gentisic acid (C7H6O4; MW=154.12) T (K)

[G-2] 10

110 10.9 1.57 150 14.8 2.14 200 17.2 2.48 5 300 22.5 3.25 500 28.1 4.06 1000 37.7 5.45 1500 45.2 6.53 0 2000 50.3 7.27 0 1: Obtained by digitizing the graph in the original article. 2: "Nl" means "Normliter," which is one liter at 273.15 K and 1 atm. 3: Calculated from S. Synonyms: 2,5-Dihydroxybenzoic acid; 5-Hydroxysalicylic acid Source: Stahl, E.; Schilz, W. Talanta (1979), 26, 675-679.

y x 106

313.15

P1) (bar) S1)(mg/Nl2)) y3) x 106

350

1000

2000

P (bar)

381

CAT4240—CHAPTER 7—31/10/2006—18:52—MUGUNTHAN—XML MODEL C – pp. 381–385

382

Solubility in Supercritical Carbon Dioxide

Ginger (Zingiber officinale Roscoe) rhizomes extract w1)

[G-3]

106

x P (bar) W (g/kg) 8000 150.0 5.15 5120 200.0 4.14 4120 6000 250.0 5.38 5350 303.15 100.0 2.92 2910 150.0 5.78 5750 4000 200.0 5.21 5180 250.0 5.90 5870 2000 300.0 6.57 6530 313.15 100.0 1.99 1990 0 150.0 6.41 6370 200.0 6.73 6690 50 250.0 7.20 7150 300.0 5.97 5930 1: Calculated from W. Source: Rodrigues, V. M.; Sousa, E. M. B. D.; Monteiro, A. R.; Chiavone-Filho, O.; Marques, M. O. M.; Meireles, M. A. A. J. Supercrit. Fluids (2002), 22(1), 21-36.

w x 106

T (K) 293.15

D-(+)-Glucose

T (K)

293.15 K 303.15 K 313.15 K

150

250 P (bar)

[G-4]

(C6H12O6; MW=180.16) 0.3

P1) (bar) S1) (μg/Nl2)) y3) x 106

313.15

y x 106

296 0.88 0.109 500 1.08 0.133 1000 1.51 0.187 1497 1.89 0.234 1983 1.79 0.221 1: Obtained by digitizing the graph in the original article. 2: "Nl" means "Normliter," which is one liter at 273.15 K and 1 atm. 3: Calculated from S. Synonyms: D-Glucose; Dextrose Source: Stahl, E.; Schilz, W. Chem. Ing. Tech. (1978), 50(7), 535-537.

350

0.2

0.1 0

CAT4240—CHAPTER 7—31/10/2006—18:52—MUGUNTHAN—XML MODEL C – pp. 381–385

1000 P (bar)

2000

Solubility Data G D-(+)-Glucose

383

[G-5]

(C6H12O6; MW=180.16) 106

60 308.2 K 328.2 K 348.2 K

40 y x 106

yx T (K) P (bar) 308.2 50.3 37.4 73.0 32.9 98.2 20.6 139.5 11.9 165.1 17.0 186.1 32.8 212.3 50.1 328.2 49.9 50.1 72.5 30.9 95.1 19.0 119.4 7.2 138.9 7.7 163.7 10.2 209.5 21.9 348.2 41.1 23.2 73.0 19.3 93.4 18.3 144.0 11.8 164.2 13.3 188.1 15.5 211.2 15.9 Synonyms: D-Glucose; Dextrose Source: Yau, J.-S.; Tsai, F.-N. J. Supercrit. Fluids (1994), 7(2), 129-133.

20

0 0

100 P (bar)

Glycerol (C3H8O3; MW=92.09) P (bar)

[G-6]

y x 106

344.7 7900 551.6 5600 689.5 9750 Synonyms: Glycerin; 1,2,3-Propanetriol Source: Eissler, R.; Friedrich, J. P. J. Am. Oil Chem. Soc. (1988), 65(5), 764-767.

15000 y x 106

T (K) 325.15

200

7500 0 300

500 P (bar)

CAT4240—CHAPTER 7—31/10/2006—18:52—MUGUNTHAN—XML MODEL C – pp. 381–385

700

384

Solubility in Supercritical Carbon Dioxide

[G-7]

Glycerol (C3H8O3; MW=92.09) T (K)

P (bar)

yx

106

296.2

40 296.2 K 313.2 K 323.2 K 333.2 K

y x 106

99 22 103 21 200 27 200 25 268 26 313.2 100 22 102 21 171 29 194 29 195 31 202 29 242 31 274 32 283 32 323.2 103 20 118 25 118 25 201 32 273 34 283 37 333.2 117 24 118 24 197 34 202 34 273 39 275 39 282 38 Synonyms: Glycerin; 1,2,3-Propanetriol Source: Sovova, H.; Jez, J.; Khachaturyan, M. Fluid Phase Equil. (1997), 137(1-2), 185-191.

30

20 50

150 P (bar)

[G-8]

Glycine (C2H5NO2; MW=75.07) 313.15

P1) (bar) S1) (μg/Nl2)) y3) x 106 500 1000 1500 2000

0.261 0.352 0.398 0.394

0.077 0.104 0.118 0.117

1: Obtained by digitizing the graph in the original article. 2: "Nl" means "Normliter," which is one liter at 273.15 K and 1 atm. 3: Calculated from S. Synonym: 2-Aminoacetic acid Source: Stahl, E.; Schilz, W. Chem. Ing. Tech. (1978), 50(7), 535-537.

0.15 y x 106

T (K)

250

0.10

0.05

0

CAT4240—CHAPTER 7—31/10/2006—18:52—MUGUNTHAN—XML MODEL C – pp. 381–385

1000 P (bar)

2000

Solubility Data G

385

Grape seed1) oil

[G-9] 106

x T (K) P (bar) W (g/kg) 313.15 150 3.4 3390 200 5.7 5670 205 6.9 6850 255 10.6 10500 280 11.0 10900 290 13.3 13100 290 13.2 13000 1: Seed of grape (Vitis vinifera) from a winery in Negotino, Macedonia. 2: Calculated from W. Source: Sovova, H.; Zarevucka, M.; Vacek, M.; Stransky, K. J. Supercrit. Fluids (2001), 20(1), 15-28.

15000 w x 106

w2)

10000 5000 0 100

200

300

P (bar)

[G-10]

Griseofulvin (C17H17ClO6; MW=352.77) Menthol1) y x 106 (mol%) 0 6.0 0 7.0 0 1.0 0 2.0 0 7.0 0 14.0 0 18.0 0 0.1 0 4.0 0 7.0 0 13.0 0 18.0 2.1 27.0 2.5 71.0 3.7 133.0 4.2 217.0 6.0 266.0 0.5 2.0 2.4 43.0 3.4 110.0

130.2 130.9 313.13 95.4 114.9 128.7 195.7 235.2 323.13 95.1 129.1 161.8 195.6 232.2 313.13 96.0 117.0 130.0 198.0 239.0 323.13 96.0 130.0 164.0 1: Cosolvent in CO2. Synonym: 7-Chloro-2',4,6-trimethoxy-6'methylspiro[benzofuran-2(3H),1'- [2] cyclohexene]-3,4'-dione Source: Thakur, R., Ph.D. Dissertation, Auburn University, Auburn, Alabama, 2006.

20

y x 106

308.13

P (bar)

308.13 K 313.13 K 323.13 K

10

0 50

100

150

200

P (bar) 300 y x 106

T (K)

313.13 K 323.13 K

200 100 0 0

CAT4240—CHAPTER 7—31/10/2006—18:52—MUGUNTHAN—XML MODEL C – pp. 381–385

2 4 6 Menthol (mol/L)

250

8

Solubility Data H

Heneicosane (C21H44; MW=296.58)

[H-1]

14000 y x 106

y1) x 106 T (K) P (bar) S (g/L) 343 139.5 1.9 610 157.0 6.3 1700 179.0 14.4 3470 199.1 24.5 5470 211.1 31.6 6820 231.6 45.8 9410 12500 255.4 63.8 1: Calculated from S. Source: Chartier, T.; Delhomme, E.; Baumard, J. F.; Marteau, P.; Subra, P.; Tufeu, R. Ind. Eng. Chem. Res. (1999), 38(5), 1904-1910.

7000

0 100

200

300

P (bar)

[H-2]

2,2',3,4,4',5,5'-Heptachlorobiphenyl (C12H3Cl7; MW=395.32) yx

26 39 51 60 71 80 91 99 107 116 125 143 155 169 180 192 6 16 32 50

500 313 K 323 K 333 K

400

y x 106

T (K) P (bar) 313 100 110 120 130 140 150 160 170 180 190 200 220 240 260 280 300 323 100 110 120 130

106

300 200 100 0 50

150

250

350

P (bar)

387

CAT4240—CHAPTER 8—31/10/2006—18:58—KADAMBADI—XML MODEL C – pp. 387–449

388

Solubility in Supercritical Carbon Dioxide

140 67 150 83 160 99 170 116 180 131 190 146 200 161 220 190 240 220 260 252 280 277 300 301 333 100 5 110 8 120 17 130 30 140 47 150 70 160 94 170 120 180 141 190 168 200 196 220 246 240 295 260 343 280 387 300 432 Synonym: PCB 180 Source: Anitescu, G.; Tavlarides, L. L. J. Supercrit. Fluids (1999), 14(3), 197-211.

2,2',3,4,4',5,5'-Heptachlorobiphenyl (C12H3Cl7; MW=395.32) T (K)

P (bar)

313

100 110 120 130 140 150 160 170

n -Butane1) (mol%) 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0

y x 106 38 56 73 85 100 112 126 137

CAT4240—CHAPTER 8—31/10/2006—18:58—KADAMBADI—XML MODEL C – pp. 387–449

[H-3]

Solubility Data H

600 313 K 323 K 333 K

400 y x 106

180 5.0 147 190 5.0 158 200 5.0 171 220 5.0 192 240 5.0 205 260 5.0 223 280 5.0 236 300 5.0 250 323 100 5.0 9 110 5.0 25 120 5.0 48 130 5.0 71 140 5.0 92 150 5.0 114 160 5.0 135 170 5.0 158 180 5.0 176 190 5.0 196 200 5.0 217 220 5.0 257 240 5.0 293 260 5.0 329 280 5.0 356 300 5.0 380 333 100 5.0 8 110 5.0 12 120 5.0 26 130 5.0 46 140 5.0 71 150 5.0 103 160 5.0 136 170 5.0 173 180 5.0 201 190 5.0 237 200 5.0 275 220 5.0 339 240 5.0 390 260 5.0 441 280 5.0 482 300 5.0 524 1: Cosolvent in CO2. Synonym: PCB 180 Source: Anitescu, G.; Tavlarides, L. L. J. Supercrit. Fluids (1999), 14(3), 197-211.

389

200

0 50

150

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250 P (bar)

350

390

Solubility in Supercritical Carbon Dioxide

2,2',3,4,4',5,5'-Heptachlorobiphenyl (C12H3Cl7; MW=395.32) P (bar)

313

100 110 120 130 140 150 160 170 180 190 200 220 240 260 280 300 100 110 120 130 140 150 160 170 180 190 200 220 240 260 280 300 100 110 120 130 140

323

333

(mol%) 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0

[H-4]

y x 106 34 50 64 74 86 96 108 116 125 134 145 162 174 188 199 211 9 23 45 67 88 106 125 146 163 180 197 228 262 297 323 347 8 11 23 41 63

600 313 K 323 K 333 K

400 y x 106

T (K)

Methanol1)

200

0 50

150

CAT4240—CHAPTER 8—31/10/2006—18:58—KADAMBADI—XML MODEL C – pp. 387–449

250 P (bar)

350

Solubility Data H

391

150 5.0 94 160 5.0 124 170 5.0 155 180 5.0 184 190 5.0 214 200 5.0 245 220 5.0 299 240 5.0 353 260 5.0 401 280 5.0 444 300 5.0 491 1: Cosolvent in CO2. Synonym: PCB 180 Source: Anitescu, G.; Tavlarides, L. L. J. Supercrit. Fluids (1999), 14(3), 197-211.

Heptacosane (C27H56; MW=380.73)

[H-5]

106

400 y x 106

yx T (K) P (bar) 313 100 100 130 190 146 210 154 240 176 260 371 260 434 240 523 190 Source: Furuya, T.; Teja, A. S. J. Supercrit. Fluids (2004), 29(3), 231-236.

200 0 0

200

400 P (bar)

Heptadecane (C17H36; MW=240.47)

[H-6]

106

x T (K) P (bar) S (g/L) 343 128.8 2.8 1300 139.4 6.4 2500 149.2 12.3 4400 159.8 22.3 7300 178.6 49.9 14700 25500 196.8 93.9 1: Calculated from S. Source: Chartier, T.; Delhomme, E.; Baumard, J. F.; Marteau, P.; Subra, P.; Tufeu, R. Ind. Eng. Chem. Res. (1999), 38(5), 1904-1910.

30000 y x 106

y1)

600

15000

0 100

CAT4240—CHAPTER 8—31/10/2006—18:58—KADAMBADI—XML MODEL C – pp. 387–449

150 P (bar)

200

392

Solubility in Supercritical Carbon Dioxide

Hexabromocyclododecane (C12H18Br6; MW=641.73) y1)

106

x T (K) P (bar) w x 298.15 200 530 36 300 600 41 400 680 47 500 760 52 313.15 200 560 38 300 660 45 400 1010 69 500 1690 116 333.15 200 520 36 300 1080 74 400 1900 131 500 2930 201 353.15 200 430 30 300 1530 105 400 3350 230 500 5790 399 373.15 200 540 37 300 2660 183 400 5130 354 500 8030 555 1: Calculated from w. Source: Gamse, J.; Steinkellner, F.; Marr, R.; Alessi, P.; Kikic, I. Ind. Eng. Chem. Res. (2000), 39(12), 4888-4890.

[H-7]

600

400

298.15 K 313.15 K 333.15 K 353.15 K 373.15 K

y x 106

106

200

0 150

350

[H-8]

Hexachlorobenzene (C6Cl6; MW=284.78) 2)

1,3)

6

T (K) P (bar) y x 10 314 170 21 323 211 31 334 267 40 345 322 44 1:Obtained by digitizing the graph in the original article. May have large reading error as the original graph is small. 2: Calculated from temperature and density in the source graph. 3: Measured at a constant density (0.80 g/mL). Synonyms: BHC; Perchlorobenzene Source: Burk, R.; Kruus, P. Can. J. Chem. Eng. (1992), 70(2), 1403-1407.

50 y x 106

1)

550

P (bar)

30

10 150

CAT4240—CHAPTER 8—31/10/2006—18:58—KADAMBADI—XML MODEL C – pp. 387–449

250 P (bar)

350

Solubility Data H

393

Hexachlorobenzene (C6Cl6 ; MW=284.78) yx

20.4 22.4 23.4 27.8 34.2 16.5 19.6 23.2 28.1 30.1 10.6 17.3 20.5 25.4 30.8 Synonyms: BHC; Perchlorobenzene Source: Cross, W. J. ; Akgerman, A. Ind. Eng. Chem. Res. (1998), 37(4), 1510-1518.

40 308 K 318 K 328 K

30 y x 106

T (K) P (bar) 308 90.0 96.7 112.4 136.5 186.2 318 117.2 133.8 156.9 187.5 240.6 328 133.4 156.2 169.6 196.5 236.5

[H-9]

106

20

10

0 0

100

200 P (bar)

Hexachlorobenzene (C6Cl6; MW=284.78) P (bar) T (K)

M x 106 (mol/L)

[H-10]

y1) x 106

298 695 36.6 308 685 40.2 313 576 36.7 509 36.4 318 1: Calculated from M. Synonyms: BHC; Perchlorobenzene Source: Madras, G.; Erkey, C.; Akgerman, A. J. Chem. Eng. Data (1993), 38(3), 422-423.

300

50 y x 106

111.5

35

20 290

300

CAT4240—CHAPTER 8—31/10/2006—18:58—KADAMBADI—XML MODEL C – pp. 387–449

310 T (K)

320

394

Solubility in Supercritical Carbon Dioxide

2,2’,3,3’,4,4’-Hexachlorobiphenyl (C12H4Cl6; MW=360.88)

[H-11]

106

313 K 373 K 413 K

y x 106

yx T (K) P (bar) 8000 313 150 50 200 50 250 120 6000 300 195 350 235 400 325 4000 450 350 373 150 50 200 50 2000 250 420 300 820 413 150 50 200 200 0 250 980 100 300 2360 350 4520 400 7180 Synonym: PCB 128 Source: Miller, D. J.; Hawthrone, S. B.; Clifford, A. A. J. Supercrit. Fluids (1997), 10(1), 57-63.

300 P (bar)

500

2,2',3,3',4,4'-Hexachlorobiphenyl (C12H4Cl6; MW=360.88) P (bar)

y x 106

313.1 242.3 110 245.9 90 311.2 85 383.1 134 490.5 174 323.1 153.5 87 213.1 89 295.0 152 346.6 218 432.2 259 Synonym: PCB 128 Source: Yu, E.; Richter, M.; Chen, P.; Wang, X.; Tavlarides, L. L. Ind. Eng. Chem. Res. (1995), 34(1), 340-346.

300 313.1 K 323.1 K

y x 106

T (K)

[H-12]

200

100

0 100

200

CAT4240—CHAPTER 8—31/10/2006—18:58—KADAMBADI—XML MODEL C – pp. 387–449

300 P (bar)

400

500

Solubility Data H

395

[H-13]

2,2',4,4',5,5'-Hexachlorobiphenyl (C12H4Cl6; MW=360.88)

600

313 K 323 K 333 K

400 y x 106

y x 106 T (K) P (bar) 313 100 68 110 96 120 122 130 142 140 162 150 179 160 198 170 212 180 225 190 235 200 245 220 266 240 285 260 301 280 317 300 338 323 100 16 110 39 120 71 130 106 140 137 150 163 160 189 170 212 180 236 190 259 200 281 220 320 240 357 260 398 280 427 300 456 333 100 12 110 19 120 36 130 61 140 92 150 129 160 165 170 199 180 236 190 273 200 308 220 369 240 427 260 490 280 544 300 592 Synonym: PCB 153 Source: Anitescu, G.; Tavlarides, L. L J. Supercrit. Fluids (1999), 14(3), 197-211.

200

0 50

150

CAT4240—CHAPTER 8—31/10/2006—18:58—KADAMBADI—XML MODEL C – pp. 387–449

250 P (bar)

350

396

Solubility in Supercritical Carbon Dioxide

2,2',4,4',5,5'-Hexachlorobiphenyl (C12H4Cl6; MW=360.88) P (bar)

313

100 110 120 130 140 150 160 170 180 190 200 220 240 260 280 300 100 110 120 130 140 150 160 170 180 190 200 220 240 260 280 300 100 110 120 130 140 150 160 170 180 190 200 220

323

333

(mol%) 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0

[H-14]

y x 106 102 139 167 198 219 240 262 276 290 304 315 333 351 371 394 413 26 61 96 132 166 200 235 262 289 311 334 377 420 462 495 528 15 28 52 79 115 160 205 246 286 327 372 440

313 K 323 K 333 K

600

y x 106

T (K)

n-Butane1)

400

200

0 50

150

CAT4240—CHAPTER 8—31/10/2006—18:58—KADAMBADI—XML MODEL C – pp. 387–449

250 P (bar)

350

Solubility Data H

397

240 5.0 509 260 5.0 570 280 5.0 621 300 5.0 677 1: Cosolvent in CO2. Synonym: PCB 153 Source: Anitescu, G.; Tavlarides, L. L. J. Supercrit. Fluids (1999), 14(3), 197-211.

2,2',4,4',5,5'-Hexachlorobiphenyl (C12H4Cl6; MW=360.88) P (bar)

313

100 110 120 130 140 150 160 170 180 190 200 220 240 260 280 300 100 110 120 130 140 150 160 170 180 190 200 220 240 260 280 300 100 110 120 130 140 150

323

333

Methanol1) (mol%) 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0

y x 106 88 121 151 172 193 211 230 244 257 266 276 296 309 329 344 365 23 54 93 124 159 195 224 247 276 300 322 360 401 443 482 511 18 27 48 75 112 156

313 K 323 K 333 K

600

y x 106

T (K)

[H-15]

400

200

0 50

150

CAT4240—CHAPTER 8—31/10/2006—18:58—KADAMBADI—XML MODEL C – pp. 387–449

250 P (bar)

350

398

Solubility in Supercritical Carbon Dioxide

160 5.0 196 170 5.0 234 180 5.0 273 190 5.0 311 200 5.0 347 220 5.0 424 240 5.0 486 260 5.0 552 280 5.0 609 300 5.0 658 1: Cosolvent in CO2. Synonym: PCB 153 Source: Anitescu, G.; Tavlarides, L. L. J. Supercrit. Fluids (1999), 14(3), 197-211.

Hexachloroethane (C2Cl6; MW=236.74)

308 K 318 K 328 K

40000

y x 106

y x 106 T (K) P (bar) 308 99 14500 149 18600 199 19600 248 19900 280 18000 318 100 10300 148 23900 198 26000 247 27800 280 27000 328 97 3790 145 23200 195 38900 245 39300 38900 280 Synonym: Perchloroethane Source: Kurnik, R. T.; Holla, S. J.; Reid, R. C. J. Chem. Eng. Data (1981), 26(1), 47-51.

[H-16]

20000

0 50

150

250

P (bar)

Hexacosane (C26H54; MW=366.71) S (g/L) 1.91 4.19 7.42 11.44 15.99 22.28

x

[H-17]

106

419 825 1364 1977 2647 3546

1: Calculated from S. Source: Chartier, T.; Delhomme, E.; Baumard, J. F.; Marteau, P.; Subra, P.; Tufeu, R. Ind. Eng. Chem. Res. (1999), 38(5), 1904-1910.

4000 y x 106

T (K) P (bar) 343 158.3 177.2 194.9 216.9 237.1 260.1

y1)

2000

0 100

150

CAT4240—CHAPTER 8—31/10/2006—18:58—KADAMBADI—XML MODEL C – pp. 387–449

200 P (bar)

250

300

Solubility Data H

399

Hexacosane (C26H54; MW=366.71) yx

500

400 420 400 430 430 400

y x 106

T (K) P (bar) 313 138 144 150 205 300 413

[H-18]

106

400 300 100

Source: Furuya, T.; Teja, A. S. J. Supercrit. Fluids (2004), 29(3), 231-236.

200

300 P (bar)

Hexadecane (C16H34; MW=226.44) P (bar)

344.15 83.0 96.4 113.3 124.2

yx

[H-19]

106 2600 7800 8700 9900

12000 y x 106

T (K)

400

Source: Eustaquio-Rincon, R. ; Trejo, A. Fluid Phase Equil. (2001), 185(1-2), 231-239.

6000 0 70

100

130

P (bar)

Hexadecane (C16H34; MW=226.44)

[H-20]

y x 106

T (K) P (bar) y1) x 106 60000 333.15 50.6 1440 61.1 1940 76.0 1310 87.5 563 30000 90.5 438 97.0 2440 111.0 4380 116.0 7250 0 128.5 9380 146.0 15400 50 151.0 21800 162.0 29900 170.0 31900 182.0 49500 1: The data in the source have only one or two significant numbers, and therefore were refined using the graph in the authors' another paper: King, M. B.; Bott, T. R. Sep. Sci. Tech. (1982), 17(1), 119-150. Source: King, M. B.; Kassim, K.; Bott, T. R.; Sheldon, J. R.; Mahmud, R. S. Ber. Bunsenges. Phys. Chem. (1984), 88(9), 812-820.

100

CAT4240—CHAPTER 8—31/10/2006—18:58—KADAMBADI—XML MODEL C – pp. 387–449

150 P (bar)

200

400

Solubility in Supercritical Carbon Dioxide

Hexadecane (C16H34; MW=226.44) y1)

[H-21]

106

x T (K) P (bar) w x 313.2 99.0 50000 10100 123.9 99000 20900 142.0 138000 30200 154.7 176000 39900 323.2 121.4 50000 10100 142.5 99000 20900 154.5 138000 30200 162.4 176000 39900 1: Calculated from w. Source: Nieuwoudt, I.; du Rand, M. J. Supercrit. Fluids (2002), 22(3), 185199.

50000 y x 106

106

313.2 K 323.2 K

25000

0 80

100

120

140

160

P (bar)

4-(Hexadecylamino)-7-nitrobenz-2-oxa-1,3-diazole (C22H36N4O3; MW=404.55) 313.15

333.15

99 130 148 150 180 210 100 130 140 150 180 210

1.1 2.0 3.0 3.4 4.2 4.4 0.6 0.6 2.2 4.6 10.3 16.2

[H-22]

y2) x 106 0.12 0.22 0.33 0.37 0.46 0.48 0.07 0.07 0.24 0.50 1.12 1.76

1: Obtained by digitizing the graph in the original article. May have reading error of up to 10% as the original graph is small. 2: Calculated from w. Synonyms: N-Hexadecyl-7-nitro-4benzofurazanamine; NBD-HAD Source: Wang, Y.; Yang, C.; Tomasko, D. Ind. Eng. Chem. Res.(2002), 41(7), 1780-1786.

2.0 313.15 K 333.15 K

1.5 y x 106

T (K) P1) (bar) w1) x 106

180

1.0

0.5

0.0 50

100

CAT4240—CHAPTER 8—31/10/2006—18:58—KADAMBADI—XML MODEL C – pp. 387–449

150 P (bar)

200

250

Solubility Data H

401

Hexamethylbenzene (C12H18; MW=162.27) P (bar)

308.15

Cosolvent (mol%)

y x 106

150 200 350

0.0 1700 0.0 1780 0.0 1910 Octane 120 3.5 3000 150 3.5 3270 200 3.5 3500 250 3.5 3610 300 3.5 3710 350 3.5 3700 Pentane 100 3.5 2060 120 3.5 2360 150 3.5 2470 200 3.5 2740 300 3.5 3040 350 3.5 3080 Undecane 120 3.5 3850 200 3.5 4250 300 3.5 4600 350 3.5 4730 Source: Dobbs, J. M.; Wong, J.; Johnston, K. P. J. Chem. Eng. Data (1986), 31(3), 303-308.

Pure CO2 Octane Pentane Undecane

5000

4000 y x 106

T (K)

[H-23]

3000

2000

1000 50

150

250 P (bar)

Hexamethylbenzene (C12H18; MW=162.27) P (bar)

Cosolvent (mol%)

y x 106

Acetone 3.5 1580 3.5 1510 3.5 1550 3.5 1660 3.5 1830 3.5 2170 3.5 2240 3.5 2300 3.5 2240 3.5 2210 Methanol 100 3.5 1500 120 3.5 1630 200 3.5 2110 200 3.5 2320 3.5 2210 350 Source: Dobbs, J. M.; Wong, J. M.; Lahiere, R. J.; Johnston, K. P. Ind. Eng. Chem. Res. (1987), 26(1), 56-65. 308.15

100 100 100 100 120 150 200 250 350 350

[H-24]

2500

y x 106

T (K)

350

2000

1500 Acetone MeOH

1000 50

150

CAT4240—CHAPTER 8—31/10/2006—18:58—KADAMBADI—XML MODEL C – pp. 387–449

250 P (bar)

350

402

Solubility in Supercritical Carbon Dioxide

Hexamethylbenzene (C12H18; MW=162.27)

[H-25]

y x 106

69.9 55 83.7 1360 104.3 1070 138.8 1370 207.7 1540 276.7 1580 345.6 1550 323.15 69.9 35 76.8 40 258 90.5 104.3 390 125.0 1470 138.8 1770 173.3 2350 207.7 2740 276.7 3200 345.6 3490 343.15 83.7 87 104.3 285 125.0 685 138.8 1240 173.3 2840 207.7 4170 276.7 5580 345.6 6760 414.5 6820 483.5 6790 Source: Johnston, K. P.; Ziger, D. H.; Eckert, C. A. Ind. Eng. Chem. Fund. (1982), 21(3), 191-197.

8000 303.15 K 323.15 K 343.15 K

6000 y x 106

T (K) 303.15

P(bar)

4000

2000

0 0

200 P (bar)

Hexanoic acid (C6H12O2; MW=116.16)

[H-26] 12000 313 K 323 K

y x 106

y x 106 T (K) P (bar) 313 75 350 88 6270 100 10320 105 10510 120 10720 130 10830 323 75 430 88 2280 95 5630 105 8950 123 9910 130 10030 140 10100 Synonyms: Caproic acid; 1-Hexanoic acid Source: Ghaziaskar, H. S.; Nikravesh, M. Fluid Phase Equil. (2003), 206(1-2), 215-221.

400

8000

4000

0 50

CAT4240—CHAPTER 8—31/10/2006—18:58—KADAMBADI—XML MODEL C – pp. 387–449

100 P (bar)

150

Solubility Data H

403

Hexanoic acid (C6H12O2; MW=116.16)

[H-27]

106

14000 y x 106

yx P (bar) T (K) 123 313 10700 323 9910 333 9100 353 4450 Synonyms: Caproic acid; 1-Hexanoic acid Source: Ghaziaskar, H. S.; Nikravesh, M. Fluid Phase Equil. (2003), 206(1-2), 215-221.

7000 0 300

320

340 T (K)

1-Hexanol (C6H14O; MW=102.17) T (K)

P (bar)

S (g/L)

[H-28]

y1) x 106

13200 101 12.4 18100 103 18.1 25100 105 26.7 55700 110 69.0 81500 114 111.5 24000 401.8 121 11.6 39600 160 27.6 62700 180 51.8 82800 190 74.5 195 99.5 105000 1: Calculated from S. Synonym: n-Hexyl alcohol Source: Nickel, D.; Schneider, G. M. J. Chem. Thermodyn. (1989), 21(3), 293305.

120000

323.4

y x 106

323.4 K 401.8 K

60000

0 100

3-Hexanol (C6H14O; MW=102.17) T (K) P (bar) 323.4 84.0 86.0 88.0 90.0 90.0 92.0 92.0 94.0

S (g/L) 3.8 4.5 5.2 7.2 7.0 9.6 8.3 14.9

360

y1,2) x 106 6670 7490 8200 10700 10400 13400 11600 19600

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150

200

P (bar)

[H-29]

404

397.3

100.0 106.0 110.0 115.0 120.0 126.0 130.0 135.0 139.0 100.0 105.0 110.0 115.0 120.0 127.0 134.0 141.0 147.0 154.0 159.0

8.8 10.6 12.7 14.6 19.5 23.2 32.1 40.6 58.3 13.6 15.0 18.0 20.4 22.4 26.9 31.7 39.4 49.6 64.9 86.1

18200 20100 22700 24400 30400 33500 43700 51700 69700 34300 35600 40200 43000 44600 49700 54400 62800 74090 89800 111700

120000 323.4 K 362.8 K 397.3 K

80000 y x 106

362.8

Solubility in Supercritical Carbon Dioxide

40000

0 75

100

125

150

175

P (bar)

1: Calculated from S. 2: The solubility data in italics at 397.3 K are one order of magnitude smaller than the actual in the original article and therefore are corrected based on Friedrich's original thesis. Source: Friedrich, J.; Schneider, G. M. J. Chem. Thermodyn. (1989), 21(3), 307-319.

Hexatriacontane (C36H74; MW=506.97) T (K) 308.2

318.2

P (bar)

y1) x 106

100 120 140 160 180 200 240 100 120 140

4.8 7.8 9.2 12.0 14.0 15.0 19.0 1.2 14.0 28.0

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[H-30]

Solubility Data H

333.2

42.0 55.0 59.0 78.0

100 120 140 160 180 200 240 100 120 140 160 180 200 240

0.2 7.8 42.0 98.0 150.0 210.0 290.0

600

308.2 K 318.2 K 328.2 K 333.2 K

400 6

160 180 200 240

y x 10

328.2

405

0.1 4.4 46.0 110.0 220.0 220.0 560.0

200

0 50

1: Only the data at 200 and 240 bar at 318.2 K, and at 160 and 200 bar at 333.2 K are experimental ones. All the other data (in italics) are the extrapolated values in the original article. Source: Chandler, K.; Pouillot, F. L. L.; Eckert, C. A. J. Chem. Eng. Data (1996), 41, 6-10.

Hexatriacontane (C36H74; MW=506.97) T (K) P (bar) 318.2 35.2 57.7 86.5 107.6 131.4 155.1 180.3 206.5

yx

106 262 265 259 269 277 303 404 527

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150 P (bar)

250

[H-31]

406

Solubility in Supercritical Carbon Dioxide

35.9 58.1 86.4 109.3 132.7 155.1 180.0 202.7 338.2 30.0 58.1 85.0 107.4 130.3 156.5 180.0 203.4

254 257 260 255 269 289 423 518 246 244 259 248 319 392 601 997

1200 318.2 K 328.2 K 338.2 K

800 y x 106

328.2

400

0 0

Source: Yau, J. S.; Tsai, F. N. J. Chem. Eng. Data (1993), 38(2), 171174.

100

200

P (bar)

Hexatriacontane (C36H74; MW=506.97) P (bar) 223.2 289.6 234.3 254.4 263.8 285.4 292.6 250.0 260.6 266.3 276.9 289.8 254.4 260.0 272.6 273.1 289.7

348.5

357.0

366.9

wx

14000 8000 14000 10000 19000 8000 22000 14000 10000 19000 22000 8000 14000 10000 19000 22000 8000

y1)

x

[H-32]

106

1200 700 1200 900 1700 700 1900 1200 900 1700 700 1900 1200 900 1700 700 1900

2000

1500

344.0 K 348.5 K 357.0 K 366.9 K

y x 106

T (K) 344.0

106

1000

500 200

250

1: Calculated from w. Source: Nieuwoudt, I.; du Rand, M. J. Supercrit. Fluids (2002), 22(3), 185199.

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300 P (bar)

350

Solubility Data H

407

Hydrocortisone (C21H30O5; MW=362.46) yx

0.046 0.098 0.124 0.148 0.254 0.516 0.575 0.873 0.901 0.004 0.098 0.163 0.232 0.393 0.568 0.693 0.865 0.878 0.003 0.063 0.139 0.164 0.457 0.502 0.644 0.734

1.0 308.15 K 328.15 K 373.15 K

0.8

y x 106

T (K) P (bar) 308.15 99.0 113.8 129.4 146.1 160.8 177.5 196.1 210.8 226.5 328.15 99.0 113.8 129.4 146.1 160.8 177.5 196.1 210.8 226.5 373.15 99.0 113.8 129.4 146.1 160.8 177.5 196.1 226.5

[H-33]

106

0.6 0.4 0.2 0.0 50

150 P (bar)

250

Synonyms: Cortisol; 11b, 17a, 21Trihydroxypregn-4-ene-3,20-dione Source: Dean, J. R.; Kane, M.; Khundker, S.; Dowle, C.; Tranter, R. L.; Jones, P. Analyst (1995), 120(8), 21532157.

Hydroquinone (C6H6O2; MW=110.11) T (K)

P (bar)

308.15 83.6 89.2 92.7 97.4 106.1 109.1 135.2 158.3 172.7

yx

106 3.36 4.81 4.69 5.72 5.91 6.81 7.78 8.42 8.81

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[H-34]

408

Solubility in Supercritical Carbon Dioxide

9.78 10.21 10.74 11.39 11.16 11.42 2.04 2.87 4.28 5.75 7.79 9.05 10.65 11.56 12.43 13.41 13.58 13.94 14.29 14.32 14.70 14.95

15

y x 106

203.4 229.6 255.0 271.8 298.2 311.6 318.15 85.7 91.6 96.2 99.8 108.6 119.4 129.5 141.4 168.8 192.4 209.7 231.2 249.4 253.1 286.3 313.3

10

5 308.15 K 318.15 K

0 50

150

250

350

P (bar)

Synonym: 1,4-Benzenediol Source: Coutsikos, P.; Magoulas, K.; Tassios, D. J. Chem. Eng. Data (1995), 40(4), 953-958.

Hydroquinone (C6H6O2; MW=110.11) 333

348

P (bar) 100 125 150 175 200 225 250 275 300 325 350 100 125 150 175 200 225 250 275 300 325 350

y x 106 7.0 12.0 21.2 28.1 29.0 28.9 31.3 30.8 32.4 33.5 33.8 9.0 10.0 20.0 24.3 31.2 31.3 35.2 36.7 40.4 41.0 42.4

60 333 K 348 K 363 K

40 y x 106

T (K)

[H-35]

20

0 50

150

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250 P (bar)

350

Solubility Data H

409

363

100 10.0 125 12.0 150 15.9 175 21.5 200 28.3 225 31.9 250 41.0 275 44.0 300 49.5 325 51.5 350 55.9 Synonym: 1,4-Benzenediol Source: Garcia-Gonzalez, J.; Molina, M. J.; Rodriguez, F.; Mirada, F. Fluid Phase Equil. (2002), 200(1), 31-39.

Hydroquinone (C6H6O2; MW=110.11)

[H-36]

P1) TBP2) y1)x 106 (bar) (mol%) 308.15 105 0.0008 6.9 3000 107 0.0008 7.8 175 0.0008 8.0 178 0.0008 9.8 245 0.0008 10.0 312 0.0008 10.9 2000 107 0.099 16.0 175 0.099 20.0 243 0.099 14.0 314 0.099 26.0 1000 106 0.62 250.0 175 0.62 280.0 244 0.62 295.0 312 0.62 320.0 141 2.0 2600.0 0 183 2.0 2400.0 50 225 2.0 2480.0 266 2.0 2300.0 304 2.0 2280.0 347 2.0 2500.0 1: Obtained by digitizing the graph in the original article. 2: Tributyl phosphate as a cosolvent in CO2. Synonym: 1,4-Benzenediol Source: Johnston, K.P.; McFann, G. J.; Peck, D. G.; Lemert, R. M. Fluid Phase Equil. (1989), 52, 337346.

y x 106

T (K)

0.0008% 0.099% 0.62% 2.0%

150

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250 P (bar)

350

410

Solubility in Supercritical Carbon Dioxide

Hydroquinone (C6H6O2; MW=110.11) P (bar)

308.15 103.4 128.1 153.2 177.2 177.2 203.0 252.9 327.8 308.15

318.15

308.15

308.15

318.15

308.15

104.4 104.8 172.8 174.8 241.5 308.8 105.1 173.5 241.5 308.8 105.1 172.1 239.5 309.2 104.4 172.4 240.8 307.1 104.1 172.1 240.1 306.8 137.8 179.9 179.9 221.1 261.9 299.3 340.8

Cosolvent1) (%) Methanol 2.8 2.8 2.8 2.8 2.8 2.8 2.8 2.8 TBP 0.0008 0.0008 0.0008 0.0008 0.0008 0.0008 0.0008 0.0008 0.0008 0.0008 0.099 0.099 0.099 0.099 0.62 0.62 0.62 0.62 0.62 0.62 0.62 0.62 2.0 2.0 2.0 2.0 2.0 2.0 2.0

y x 106 62.2 65.7 73.6 76.3 77.4 84.3 88.1 92.2 7.87 6.66 8.14 9.90 10.80 11.20 11.0 12.4 15.0 16.8 15.1 19.2 13.5 25.8 244 266 288 326 198 309 336 374 2550 2340 2290 2430 2330 2310 2460

3000

2000

308.15 K, MeOH 2.8% 308.15 K, TBP 0.0008% 318.15 K, TBP 0.0008% 308.15 K, TBP 0.099% 308.15 K, TBP 0.62% 318.15 K, TBP 0.62% 308.15 K, TBP 2.0%

y x 106

T (K)

[H-37]

1000

0 50

150

1: Solute-free basis. Synonym: 1,4-Benzenediol Source: Lemert, R. M.; Johnston, K. P. Ind. Eng. Chem. Res. (1991), 30(6), 1222-1231.

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250 P (bar)

350

Solubility Data H

411

Hydroquinone (C6H6O2; MW=110.11)

0.62 0.62 0.62 0.62 0.62 0.62

175.1 308.15 313.15 318.15 323.15 328.15 333.15

500

y x 106 266 286 309 368 364 406

6

(mol%)

[H-38]

y x 10

P (bar) T (K)

TBP1)

350 200 300

1:Tri-n-butyl phosphate as a cosolvent in CO2 on a solute-free basis. Synonym: 1,4-Benzenediol Source: Lemert, R. M.; Johnston, K. P. Ind. Eng. Chem. Res. (1991), 30(6), 1222-1231.

320

340

T (K)

Hydroquinone(1) + p-Quinone(2) Mixture1) y1 x

10.0 38.0 92.0 127.5 146.5 180.9 237.3 310.8 297.4 309.7 296.3 12.4 29.6 67.2 104.8 163.6 205.7 271.7 439.4 445.1 437.4 441.9 24.5 30.1 52.8

y2 x

[H-39]

106

70 540 2100 3070 6120 7270 10890 11180 11500 11440 11520 70 160 540 1420 2500 3970 6190 7820 9640 11950 12190 70 120 300

H-QN 333 K H-QN 348 K H-QN 363 K p-QN 333 K p-QN 348 K p-QN 363 K

12000

y x 106

T (K) P (bar) 333 100 125 150 175 200 225 250 275 300 325 350 348 100 125 150 175 200 225 250 275 300 325 350 363 100 125 150

106

8000

4000

0 50

150

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250 P (bar)

350

412

Solubility in Supercritical Carbon Dioxide

175 90.5 720 200 163.0 1510 225 298.0 2450 250 358.0 3680 275 411.0 5110 300 462.0 6700 325 516.2 8010 350 511.9 9260 1: Solubility was measured from an equimolar mixture of hydroquinone and p-quinone. Source: Garcia-Gonzalez, J.; Molina, M. J.; Rodriguez, F.; Mirada, F. Fluid Phase Equil. (2002), 200(1), 31-39.

1-Hydroxyanthraquinone (C14H8O3; MW=224.21) 308

318

328

P (bar) 122 152 182 213 243 274 304 334 355 122 152 182 213 243 274 304 334 355 122 152 182 213 243 274 304 334 355

S (g/L) 0.39 0.40 0.45 0.51 0.56 0.58 0.61 0.65 0.66 0.10 0.26 0.38 0.45 0.61 0.64 9.69 0.75 0.80 0.15 0.26 0.37 0.50 0.63 0.74 0.87 0.93 1.04

y x

100 95 103 114 123 125 128 134 135 30 69 95 108 141 144 153 163 171 57 76 101 127 154 176 201 208 232

500 400

y x 106

T (K)

[H-40]

106

308 K 318 K 328 K 338 K 348 K

300 200 100 0 100

200

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300 P (bar)

400

Solubility Data H

413

338

122 0.09 45 152 0.24 83 182 0.42 127 213 0.59 162 243 0.80 208 274 1.00 249 304 1.14 277 334 1.40 330 355 1.55 359 348 122 0.07 40 152 0.11 45 182 0.50 167 213 0.72 216 243 0.95 266 274 1.18 312 304 1.61 409 334 1.70 418 355 1.84 445 Source: Shamsipur, M.; Karami, A. R.; Yamini, Y.; Sharghi, H. J. Supercrit. Fluids (2004), 32(1-3), 47-53.

1-Hydroxy-2-(1-butoxymethyl)anthraquinone (C19H18O4; MW=310.34) 308

318

328

P (bar) 122 152 182 213 243 274 304 334 355 122 152 182 213 243 274 304 334 355 122 152 182 213 243 274 304 334 355

S (g/L) 1.00 1.84 2.43 3.00 3.30 3.77 4.11 4.28 4.74 0.73 1.45 2.11 2.86 3.64 4.30 5.03 5.71 6.29 0.33 1.64 1.96 2.64 3.69 5.24 6.41 7.59 8.39

y x

183 319 406 485 521 583 625 641 703 157 276 378 491 606 696 798 890 971 90 355 382 485 651 893 1066 1234 1346

3000

2000

308 K 318 K 328 K 338 K 348 K

y x 106

T (K)

[H-41]

106

1000

0 100

200

CAT4240—CHAPTER 8—31/10/2006—18:58—KADAMBADI—XML MODEL C – pp. 387–449

P (bar)

300

400

414

Solubility in Supercritical Carbon Dioxide

338

122 0.24 87 152 0.86 218 182 1.79 388 213 2.86 569 243 4.18 785 274 6.04 1090 304 7.92 1383 334 9.47 1609 355 10.85 1814 348 122 0.19 82 152 0.37 110 182 1.16 281 213 2.48 540 243 6.61 1334 274 8.94 1714 304 11.70 2148 334 13.55 2414 355 15.44 2699 Source: Shamsipur, M.; Karami, A. R.; Yamini, Y.; Sharghi, H. J. Supercrit. Fluids (2004), 32(1-3), 47-53.

1-Hydroxy-2-(ethoxymethyl)anthraquinone (C17H14O4; MW=282.29) 308

318

328

P (bar) 122 152 182 213 243 274 304 334 355 122 152 182 213 243 274 304 334 355 122 152 182 213 243 274 304 334 355

S (g/L) 0.40 0.77 1.06 1.30 1.51 1.66 1.84 1.86 1.90 0.42 0.79 1.34 1.60 1.90 2.15 2.39 2.63 2.86 0.36 0.63 1.11 1.54 1.95 2.47 2.82 3.27 3.73

y x 106 80 146 194 232 262 282 309 307 310 100 166 263 303 348 383 417 450 486 109 149 238 311 379 462 515 585 658

1200

800

308 K 318 K 328 K 338 K 348 K

y x 106

T (K)

[H-42]

400

0 100

200

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300 P (bar)

400

Solubility Data H

415

338

122 0.29 115 152 0.33 92 182 0.72 171 213 1.32 288 243 1.92 396 274 2.48 491 304 3.03 582 334 3.73 697 355 4.42 812 348 122 0.05 23 152 0.21 70 182 0.66 175 213 1.34 321 243 2.17 383 274 2.88 607 304 3.71 750 334 4.69 919 355 5.73 1100 Source: Shamsipur, M.; Karami, A. R.; Yamini, Y.; Sharghi, H. J. Supercrit. Fluids (2004), 32(1-3), 47-53.

1-Hydroxy-2-(isobutoxymethyl)anthraquinone1) (C19H18O4; MW=310.34) 308

318

328

P (bar) 122 152 182 213 243 274 304 334 355 122 152 182 213 243 274 304 334 355 122 152 182 213 243 274 304 334 355

S (g/L) 1.42 2.04 2.88 3.32 3.85 4.55 5.52 5.70 5.27 0.81 1.67 2.65 3.71 4.80 5.03 6.80 8.04 7.89 0.60 1.27 2.52 3.84 5.12 6.56 7.68 8.87 9.23

x

[H-43]

106 261 353 480 537 608 704 841 854 782 174 317 474 637 799 815 1080 1252 1217 164 274 491 706 902 1120 1277 1442 1480

3000

2000

308 K 318 K 328 K 338 K 348 K

y x 106

T (K)

y2)

1000

0 100

200

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300 P (bar)

400

416

Solubility in Supercritical Carbon Dioxide

338

348

122 152 182 213 243 274 304 334 355 122 152 182 213 243 274 304 334 355

0.14 0.55 1.63 2.99 4.91 6.49 8.13 9.72 11.03 0.06 0.25 0.96 2.06 3.76 6.37 9.58 12.43 15.10

51 38 353 596 923 1170 1419 1652 1844 25 74 233 447 759 1220 1760 2213 2640

1: The compound name is corrected based on the structure and molecular weight shown in Figure 1 of the source. 2: The mole fraction solubility (y x 104) at 318 K and 304 bar was mistyped to 1.80 in the source table and thus was corrected based on S in the same source. Source: Shamsipur, M.; Karami, A. R.; Yamini, Y.; Sharghi, H. J. Supercrit. Fluids (2004), 32(1-3), 47-53.

1-Hydroxy-2-(methoxymethyl)anthraquinone (C16H12O4; MW=268.26) T (K) 308

318

328

P (bar) 122 152 182 213 243 274 304 334 355 122 152 182 243 274 304 334 355 122 152 182 213 243

S (g/L) 0.36 0.57 0.86 0.94 0.99 1.03 1.07 1.18 1.34 0.24 0.47 0.73 1.16 1.28 1.34 1.43 1.43 0.16 0.40 0.67 0.96 1.22

6

y x 10

77 113 166 177 181 184 188 205 229 60 104 152 223 239 245 257 255 51 101 151 205 248

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[H-44]

Solubility Data H

417

308 K 318 K 328 K 338 K 348 K

y x 10

6

274 1.48 291 600 304 1.62 312 334 1.76 332 355 1.79 333 338 122 0.14 57 152 0.25 72 400 182 0.57 142 213 0.77 178 243 1.13 245 274 1.62 337 304 1.92 388 200 334 2.16 425 355 2.24 434 348 122 0.12 59 152 0.19 65 182 0.49 137 0 213 0.89 223 243 1.06 247 100 274 1.96 436 304 2.26 481 334 2.59 534 355 2.65 537 Source: Shamsipur, M.; Karami, A. R.; Yamini, Y.; Sharghi, H. J. Supercrit. Fluids (2004), 32(1-3), 47-53.

200

300 P (bar)

1-Hydroxy-4-(prop-2-enyloxy)anthraquinone (C17H12O4; MW=280.27) y x 106 49 51 70 83 105 117 128 131 50 75 112 116 133 148 167 59 96 130 171 197 243

600

400

308 K 318 K 328 K 338 K 348 K

6

S (g/L) 0.24 0.27 0.39 0.47 0.62 0.71 0.78 0.81 0.27 0.54 0.66 0.72 0.85 0.97 1.13 0.26 0.47 0.67 0.91 1.08 1.37

[H-45]

y x 10

T (K) P (bar) 308 121.6 162.1 202.7 243.2 283.7 324.2 364.8 405.3 318 121.6 162.1 202.7 243.2 283.7 324.2 364.8 328 162.1 202.7 243.2 283.7 324.2 364.8

400

200

0 100

200

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300 P (bar)

400

418

Solubility in Supercritical Carbon Dioxide

338

348

121.6 162.1 202.7 243.2 283.7 324.2 364.8 405.3 121.6 162.1 202.7 243.2 283.7 324.2 364.8 405.3

0.02 0.18 0.41 0.71 1.20 1.36 1.71 1.99 0.02 0.13 0.42 0.84 1.30 1.75 2.22 2.67

9 46 94 147 201 258 314 358 10 39 105 188 272 348 425 498

Source: Fat'hi, M. R.; Yamini, Y.; Sharghi, H.; Shamsipur, M. J. Chem. Eng. Data (1998), 43(3), 400-402.

1-Hydroxy-8-(prop-2-enyloxy)anthraquinone (C17H12O4; MW=280.27) 121 199 264 314 377 426 478 531 82 187 290 399 504 590 677 745 50 178 328 463 604 754 907 26 155 340

y1) x 106 25 37 47 55 64 70 78 85 19 38 56 74 90 102 115 124 15 41 68 90 113 137 160 10 41 77

300

200

308 K 318 K 328 K 338 K

6

S (g/m3)

y x 10

T (K) P (bar) 308.15 122 162 203 243 284 324 365 405 318.15 122 162 203 243 284 324 365 405 328.15 122 162 203 243 284 324 365 338.15 122 162 203

[H-46]

100

0 100

200

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300 P (bar)

400

Solubility Data H

243 284 324 365 405

419

556 778 1017 1238 1446

116 154 193 227 259

1: The magnitude (x 104) of y in the original table must have been misprinted and thus was corrected to "x 105" based on S. Source: Fat'hi, M. R.; Yamini, Y.; Sharghi, H.; Shamsipur, M. Talanta (1999), 48(4), 951-957.

1-Hydroxy-2-(1-propoxymethyl)anthraquinone (C18H16O4; MW=296.32)

318

328

338

122 152 182 213 243 274 304 334 355 122 152 182 213 243 274 304 334 355 122 152 182 213 243 274 304 334 355 122 152 182 213 243 274 304 334 355

S (g/L) 0.53 1.21 1.58 1.84 1.95 2.18 2.47 2.75 3.29 0.54 1.19 1.85 2.40 2.99 3.42 3.81 4.35 4.69 0.66 0.85 1.68 2.39 2.97 3.65 4.40 5.44 6.06 0.71 0.62 1.57 2.46 3.43 4.37 5.72 7.07 7.95

y x 10

103 221 276 311 322 353 394 431 511 122 237 347 432 521 580 634 710 758 189 191 343 461 549 652 766 927 1017 267 165 356 512 676 826 1046 1259 1392

1500

6

308

P (bar)

y x 10

T (K)

[H-47]

6

308 K 318 K 328 K 338 K 348 K

1000

500

0 100

200

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300 P (bar)

400

420

Solubility in Supercritical Carbon Dioxide

348

122 0.23 104 152 0.34 106 182 0.93 236 213 2.02 460 243 3.35 708 274 4.85 972 304 6.61 1272 334 8.07 1506 355 9.16 1676 Source: Shamsipur, M.; Karami, A. R.; Yamini, Y.; Sharghi, H. J. Supercrit. Fluids (2004), 32(1-3), 47-53.

p -Hydroxyazobenzene (C12H10N2O; MW=198.22) y x 10

6000 6

2570 2750 3450 3540 3950 1830 3290 5160 5930 6360 Synonyms: C. I. Solvent Yellow 7; 4(Phenylazo)phenol Source: Maeda, S.; Mishima, K.; Matsuyama, K.; Baba, M.; Hirabaru, T.; Ishikawa, H.; Hayashi, K.-I. J. Chem. Eng. Data (2001), 46(3), 647-650.

y x 10

T (K) P (bar) 308.2 91 101 152 203 253 318.2 91 101 152 203 253

[H-48]

6

4000 2000

308.2 K 318.2 K

0 50

150 P (bar)

p -Hydroxyazobenzene (C12H10N2O; MW=198.22) 6

[H-49]

6

10000 y x 10

y x 10 T (K) P (bar) 333.2 101 1710 152 5410 203 7670 253 8570 Synonyms: 4-(Phenylazo)phenol; C. I. Solvent Yellow 7 Source: Mishima, K.; Matsuyama, K.; Ishikawa, H.; Hayashi, K-I.; Maeda, S. Fluid Phase Equil. (2002), 194-197, 895-904.

250

5000

0 50

CAT4240—CHAPTER 8—31/10/2006—18:58—KADAMBADI—XML MODEL C – pp. 387–449

150 P (bar)

250

Solubility Data H

421

o -Hydroxybenzoic acid (C7H6O3; MW=138.12) T (K)

y1) x 106

7 79 144 182 600 211 224 254 272 318 30 400 46 98 169 191 208 200 209 242 268 295 448 0 559 50 328 16 27 41 196 266 344 390 1: The data in italics are measured by static method. All others are from dynamic method. Synonyms: 2-Hydroxybenzoic acid; Salicylic acid Source: Bristow, S.; Shekunov, B. Y.; York, P. Ind. Eng. Chem. Res. (2001), 40(7), 1732-1739.

308 K 318 K 328 K

6

80 90 100 110 120 130 140 150 85 90 95 105 110 112 115 125 135 145 161 202 80 90 100 125 135 150 165

y x 10

308

P (bar)

[H-50]

100

o -Hydroxybenzoic acid (C7H6O3; MW=138.12) T (K) P (bar) 318 102 120 122 140 172 185 327 120 130

6

y x 10

111 128 214 191 250 312 72 105

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150

200

P (bar)

[H-51]

422

Solubility in Supercritical Carbon Dioxide

135 145 140 319 161 497 180 478 190 637 200 574 220 625 328 103 20 114 83 133 211 138 285 151 331 162 380 164 352 170 389 191 495 Synonyms: 2-Hydroxybenzoic acid; Salicylic acid Source: Galia, A.; Argentino, A.; Scialdone, O.; Filardo, G. J. Supercrit. Fluids (2002), 24(1), 7-17.

318 K 327 K 328 K

y x 10

6

600

400

200

0 50

150 P (bar)

o- Hydroxybenzoic acid (C7H6O3; MW=138.12) 308.15 81.1 86.1 91.2 101.3 111.4 121.6 131.7 152.0 172.2 182.4 202.6 313.15 81.1 86.1 91.2 96.2 101.3 111.4 121.6 131.7 141.8 152.0 162.1 172.2 182.4 192.5 202.6

[H-52]

y x 106 34 75 123 164 186 208 221 241 262 280 306 11 18 66 97 136 163 192 223 253 276 302 315 350 364 395

308.15 K 313.15 K 318.15 K 328.15 K

600

6

P (bar)

y x 10

T (K)

250

400

200

0 50

100

CAT4240—CHAPTER 8—31/10/2006—18:58—KADAMBADI—XML MODEL C – pp. 387–449

150 P (bar)

200

Solubility Data H

423

318.15 81.1 7 91.2 17 101.3 83 111.4 127 121.6 172 131.7 227 141.8 259 152.0 305 162.1 325 172.2 359 182.4 385 202.6 432 328.15 101.3 34 111.4 73 121.6 130 131.7 228 141.8 268 152.0 334 162.1 401 172.2 481 182.4 546 192.5 572 202.6 624 Synonyms: 2-Hydroxybenzoic acid; Salicylic acid Source: Gurdial, G. S.; Foster, N. R. Ind. Eng. Chem. Res. (1991), 30(3), 575-580.

[H-53]

o-Hydroxybenzoic acid (C7H6O3; MW=138.12) 308.15 92.6 105.4 108.4 111.2 119.4 136.3 149.4 155.3 318.15 99.0 103.9 106.7 114.3 115.0 122.6 131.9 133.4 144.7

y x 106 140 182 189 204 218 257 281 291 97 112 133 185 220 244 265 265 304

450 308.15 K 318.15 K

300 6

P (bar)

y x 10

T (K)

150

0 50

100

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150 P (bar)

200

424

Solubility in Supercritical Carbon Dioxide

146.5 324 154.2 351 157.9 398 Synonyms: 2-Hydroxybenzoic acid; Salicylic acid Source: Ke, J.; Mao, C.; Zhong, M.; Han, B.; Yan, H. J. Supercrit. Fluids (1996), 9(2), 82-87.

o -Hydroxybenzoic acid (C7H6O3; MW=138.12)

[H-54]

6

6

8000 y x 10

y x 10 T(K) P(bar) 373 207 2070 276 2990 345 3530 6990 414 Synonyms: 2-Hydroxybenzoic acid; Salicylic acid Source: Krukonis, V. J.; Kurnik, R. T. J. Chem. Eng. Data (1985), 30(3), 247-249.

4000 0 100

200

300

y x 10

31.7 132.0 206.0 324.0 435.0 562.0

Synonyms: 2-Hydroxybenzoic acid; Salicylic acid Source: Lucien, F. P.; Foster, N. R. Ind. Eng. Chem. Res. (1996), 35(12), 4686-4699.

600 6

328 101.3 121.6 131.7 152.0 172.2 202.6

6

y x 10

P (bar)

500

[H-55]

o -Hydroxybenzoic acid (C7H6O3; MW=138.12) T (K)

400

P (bar)

300

0 50

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150 P (bar)

250

Solubility Data H

425

o -Hydroxybenzoic acid (C7H6O3; MW=138.12) y x 10

105 194 280 360 465 470 512 507 502 505 525 530 83 200 350 431 541 599 624 643 653 659 669

800

6

313.15 K 333.15 K

y x 10

T (K) P (bar) 313.15 100 115 130 150 175 190 225 250 275 300 325 350 333.15 115 130 140 150 175 200 225 250 275 300 325

[H-56]

6

400

0 50

150

250

350

P (bar)

Synonyms: 2-Hydroxybenzoic acid; Salicylic acid Source: Reverchon, E.; Donsi, G.; Gorgoglione, D. J. Supercrit. Fluids (1993), 6(4), 241-248.

o -Hydroxybenzoic acid (C7H6O3; MW=138.12) 1)

T(K) P (bar) S1) (mg/Nl2)) y3) x 106 0.04 0.09 0.37 0.70 1.29 2.04 2.81

6 14 59 113 207 328 453

500

6

80 85 90 100 120 150 200

y x 10

313.15

[H-57]

250

0 1: Obtained by digitizing the graph in the original article. 50 2: Nl means "Normliter," which is one liter at 273.15 K and 1 atm. 3: Calculated from S. Synonyms: 2-Hydroxybenzoic acid; Salicylic acid Source: Stahl, E.; Schilz, W. Talanta (1979), 26, 675-679.

100

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150 P (bar)

200

426

Solubility in Supercritical Carbon Dioxide

[H-58]

o -Hydroxybenzoic acid (C7H6O3; MW=138.12) 313

86 96 101 124 142 152 193 250 101 112 122 152 172 203

328

y x 10

600

17 90 131 200 237 259 332 407 34 76 138 309 447 583

313 K 328 K

400 6

P(bar)

y x 10

T(K)

6

200

0 50

Synonyms: 2-Hydroxybenzoic acid; Salicylic acid Source: Stassi, A.; Bettini, R.; Gazzaniga, A.; Giordano, F.; Schiraldi, A. J. Chem. Eng. Data (2000), 45(2), 161-165.

150

250

P (bar)

[H-59]

o -Hydroxybenzoic acid (C7H6O3; MW=138.12) T (K)

P (bar)

1)

HFC134a (mol%)

2)

M x 10 (mol/L)

4

101 0.0 2.8 112 0.0 5.4 1500 122 0.0 8.5 131 0.0 10.5 142 0.0 13.8 152 0.0 15.8 163 0.0 17.0 1000 172 0.0 20.9 182 0.0 21.6 202 0.0 24.0 323.15 149 5.3 68.0 500 199 5.3 83.0 230 5.3 161.0 290 5.3 196.0 343.15 121 30.4 1490.0 159 30.4 1200.0 0 188 30.4 1080.0 100 210 30.4 986.0 227 30.4 1000.0 250 30.4 830.0 1: Cosolvent on a solute-free basis. 2: The data for solubility in pure CO2 are from Abbott, A. P.; Eardley, C. A.; Tooth, R. J. Chem. Eng. Data. (1999), 44, 112. Synonyms: 2-Hydroxybenzoic acid; Salicylic acid Source: Abbott, A. P.; Eardley, C. A.; Scheirer, J. E. Green Chem. (2000), 2(2), 63-66. 4

M x 10 (mol/L)

318.15

318.15K, 0.0% 323.15K, 5.3% 343.15K, 30.4%

150

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200 P (bar)

250

300

Solubility Data H

427

[H-60]

o -Hydroxybenzoic acid (C7H6O3; MW=138.12)

323

328

318

323

328

86 91 101 111 121 141 161 201 91 96 101 111 121 141 161 201 101 111 121 141 161 201 96 101 111 121 131 141 161 181 201 101 111 121 141 161 201 101 111 121 141 161 201

Cosolvent (mol %) Acetone 3.5 3.5 3.5 3.5 3.5 3.5 3.5 3.5 3.5 3.5 3.5 3.5 3.5 3.5 3.5 3.5 3.5 3.5 3.5 3.5 3.5 3.5 Methanol 3.5 3.5 3.5 3.5 3.5 3.5 3.5 3.5 3.5 3.5 3.5 3.5 3.5 3.5 3.5 3.5 3.5 3.5 3.5 3.5 3.5

y x 106 680 800 1250 1480 1720 1850 1940 2100 720 830 1090 1460 1700 2020 2130 2330 930 1220 1540 2100 2330 2520 1250 1620 2490 2970 3280 3510 3930 4260 4480 1210 2110 2680 3590 4070 4760 1120 1660 2520 3640 4280 5120

6000 Acet 318 K Acet 323 K Acet 328 K MeOH 318 K MeOH 323 K MeOH 328 K

4000 6

318

P (bar)

y x 10

T (K)

1)

2000

0 0

50

1: Cosolvent in CO2 on a solute-free basis. Synonyms: 2-Hydroxybenzoic acid; Salicylic acid Source: Gurdial, G. S.; Macnaughton, S. J.; Tomasko, D. L.; Foster, N. R. Ind. Eng. Chem. Res. (1993), 32(7), 1488-1497.

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100

150

P (bar)

200

250

428

Solubility in Supercritical Carbon Dioxide

o -Hydroxybenzoic acid (C7H6O3; MW=138.12) Ethanol y x 106 (mol%) 87 308.15 0.00 124 15000 2.44 3760 87 bar 2.99 4760 106 bar 6.59 12600 130 bar 106 0.00 186 144 bar 10000 1.47 2320 156 bar 3.78 5390 6.91 11800 308.15 K 130 0.00 246 2.01 2680 5000 3.56 4780 6.41 11200 144 0.00 273 2.63 3180 3.60 4960 0 6.65 11500 0 2 4 6 156 0.00 290 Ethanol (mol%) 2.05 3220 3.76 5160 6.40 11100 96 318.15 0.00 78 15000 1.78 1000 4.89 7670 96 bar 5.49 9140 106 bar 106 0.00 138 127 bar 2.80 3090 139 bar 10000 3.81 5110 157 bar 4.44 6260 6.78 13000 318.15 K 127 0.00 248 2.87 2960 5000 4.47 6570 5.94 10100 139 0.00 300 2.71 3200 0 4.05 5810 5.76 9860 0 2 4 6 157 0.00 362 Ethanol (mol%) 2.49 3160 3.74 5850 5.42 9460 1: Cosolvent in CO2. Synonyms: 2-Hydroxybenzoic acid; Salicylic acid Source: Ke, J.; Mao, C.; Zhong, M.; Han, B.; Yan, H. J. Supercrit. Fluids (1996), 9(2), 82-87. P (bar)

y x 10

6

T (K)

[H-61]

1)

y x 10

6

8

CAT4240—CHAPTER 8—31/10/2006—18:59—KADAMBADI—XML MODEL C – pp. 387–449

8

Solubility Data H

429

[H-62]

o -Hydroxybenzoic acid (C7H6O3; MW=138.12) 3000 Pure CO2 w/Benzoic acid 6

2000 y x 10

Benzoic T (K) P (bar) y x 106 acid1) 318 138 0 321 0 155 428 0 172 494 0 207 441 0 241 574 318 102 trace 918 136 trace 1650 153 trace 1090 170 trace 2030 204 trace 1120 238 trace 2230 1: Cosolvent in CO2. Synonyms: 2-Hydroxybenzoic acid; Salicylic acid Source: Tavana, A.; Randolph, A. D. AIChE Symp. Ser. (1991), 87 (284, Particle. Des. Cryst.), 5-15.

1000

0 50

150

o -Hydroxybenzoic acid (1) + m-Hydroxybenzoic acid (2) Mixture1) (C7H6O3; MW=138.12) 318 101.3 121.6 131.7 152.0 172.2 202.6

y1 x106 79 186 235 293 356 436

y2 x106 0.97 2.78 3.72 4.88 6.20 7.94

1: Solubility was measured from an equimolar mixture of 1 and 2. Source: Lucien, F. P.; Foster, N. R. J. Chem. Eng. Data (1998), 43(5), 726-731.

500

[H-63]

o-HBA m-HBA

6

P (bar)

y x 10

T (K)

250

P (bar)

250

0 50

150 P (bar)

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250

430

Solubility in Supercritical Carbon Dioxide 1)

o -Hydroxybenzoic acid (1) + m-Hydroxybenzoic acid (2) Mixture (C7H6O3; MW=138.12) Methanol2) y1 x 106 y2 x 106 (mol%) 318 101 3.5 2830 108 111 3.5 3280 134 121 3.5 3440 145 141 3.5 3740 169 161 3.5 4010 183 201 3.5 4410 203 328 111 3.5 1560 41 121 3.5 2600 99 141 3.5 3540 136 161 3.5 4290 171 201 3.5 4850 199 1: Solubility was measured from an equimolar mixture of components 1 and 2. 2: Cosolvent in CO2. Source: Saquing, C. D.; Lucien, F. P.; Foster, N. R. Ind. Eng. Chem. Res. (1998), 37(10), 4190-4197.

5000

P (bar)

4000 3000

y x 106

T (K)

[H-64]

o-HBA , 318 K o-HBA , 328 K m-HBA ,318 K m-HBA ,328 K

2000 1000 0 100

150 P (bar)

o -Hydroxybenzoic acid (1) + p -Hydroxybenzoic acid (2) Mixture1) (C7H6O3; MW=138.12) 318 101.3 121.6 131.7 152.0 172.2 202.6 328 101.3 121.6 131.7 152.0 172.2 202.6

y1 x 106 80 189 236 313 366 447 31 138 201 316 434 554

y2 x 106 0.80 2.41 3.14 4.65 5.99 7.53 0.21 1.55 2.55 4.72 7.00 9.93

1: Solubillity was measured from an equimolar mixture of components 1 and 2. Source: Lucine, F. P,: Foster, N. R. Ind. Eng. Chem. Res. (1996), 35(12), 4686-4699.

600

o-HBA , 318 K o-HBA , 328 K p-HBA , 318 K p-HBA , 328 K

400 6

P (bar)

[H-65]

y x 10

T (K)

200

200

0 50

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150 P (bar)

250

Solubility Data H

431

[H-66]

o -Hydroxybenzoic acid (1) + m-Hydroxybenzoic acid (2) 1)

+ p -Hydroxybenzoic acid (3) Mixture T (K)

P (bar)

y1 x 106

y2 x 106

500

y3 x 106

o-HBA m-HBA p-HBA

y x 10

6

318 101.3 80 1.00 0.79 121.6 190 2.79 2.36 131.7 233 3.54 3.06 152.0 305 4.89 4.34 172.2 377 6.20 5.55 202.6 457 7.99 7.19 1: Solubility was measured from an equimolar mixture of components 1, 2 and 3. Source: Lucien, F. P.; Foster, N. R. J. Chem. Eng. Data (1998), 43(5), 726-731.

250

0 50

150

250

P (bar) 1)

m -Hydroxybenzoic acid (1) + p -Hydroxybenzoic acid (2) Mixture (C7H6O3; MW=138.12) y1 x 106

y2 x 106

318 101.3 0.60 0.45 121.6 1.40 1.18 131.7 1.72 1.43 152.0 2.29 1.77 172.2 2.81 2.35 202.6 3.23 2.76 328 101.3 0.22 0.17 121.6 1.12 0.85 131.7 1.63 1.22 152.0 2.71 2.01 172.2 3.56 2.68 202.6 4.63 3.52 1: Solubility was measured from an equimolar mixture of components 1 and 2. Source: Lucien, F. P.; Foster, N. R. J. Chem. Eng. Data (1998), 43(5), 726731.

m-HBA 318 K m-HBA 328 K p-HBA 318 K p-HBA 328 K

4 6

P (bar)

y x 10

T (K)

[H-67]

2

0 50

150

250

P (bar)

m- Hydroxybenzoic acid (C7H6O3; MW=138.12) 6

Source: Krukonis, V. J.;

Kurnik, R. T. J. Chem. Eng. Data (1985), 30(3), 247249.

6

140 y x 10

T (K) P (bar) y x 10 207 373 27.1 276 53.5 345 75.4 112.0 414 Synonym: 3-Hydroxybenzoic acid

[H-68]

70 0 100

200

CAT4240—CHAPTER 8—31/10/2006—18:59—KADAMBADI—XML MODEL C – pp. 387–449

300 P (bar)

400

500

432

Solubility in Supercritical Carbon Dioxide

m -Hydroxybenzoic acid (C7H6O3; MW=138.12) 6

6 318 K 328 K 6

4

y x 10

y x 10 T (K) P (bar) 318 101.3 0.58 121.6 1.49 131.7 1.74 152.0 2.28 172.2 2.85 202.6 3.37 328 101.3 0.19 121.6 1.00 131.7 1.49 152.0 2.63 172.2 3.50 202.6 4.81 Synonym: 3-Hydroxybenzoic acid Source: Lucien, F. P.; Foster, N. R. J. Chem. Eng. Data (1998), 43(5), 726-731.

[H-69]

2

0 50

100

150

200

P (bar)

m -Hydroxybenzoic acid (C7H6O3; MW=138.12) Methanol1) (mol%)

85 100 105 115 125 130 145 150 170 175 200

3.5 3.5 3.5 3.5 3.5 3.5 3.5 3.5 3.5 3.5 3.5

y x 106 74 300 293 301 336 326 344 327 354 355 341

[H-70]

400 6

318

P (bar)

y x 10

T (K)

250

200

0 50

100

1: Cosolvent in CO2. Synonym: 3-Hydroxybenzoic acid Source: Bristow, S.; Shekunov, B. Y.; York, P. Ind. Eng. Chem. Res. (2001), 40(7), 1732-1739.

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150 P (bar)

200

250

Solubility Data H

433

m -Hydroxybenzoic acid (C7H6O3; MW=138.12) P (bar)

318

91 96 111 121 141 161 201

(mol %) Acetone 3.5 3.5 3.5 3.5 3.5 3.5 3.5 3.5 3.5 3.5 3.5 3.5 3.5 3.5 3.5 3.5 3.5 3.5 3.5 3.5 3.5 3.5 Methanol 3.5 3.5 3.5 3.5 3.5 3.5 3.5

323

101 111 121 141 161 201

3.5 3.5 3.5 3.5 3.5 3.5

318

323

328

91 101 111 121 141 161 181 201 96 106 111 121 141 161 201 101 111 121 131 141 161 201

[H-71]

y2) x 106 15.0 25.6 32.6 37.3 42.8 44.9 45.8 48.3 16.7 24.7 28.5 33.6 43.7 47.2 51.6 17.7 24.0 31.4 39.5 44.5 50.4 54.7 159 263 307 326 349 376 399

500 400

y x 106

T (K)

Cosolvent1)

300

Acet 318 K Acet 323 K Acet 328 K MeOH 318 K MeOH 323 K MeOH 328 K

200 100 0 50

100

204 281 322 359 398 419

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150 P (bar)

200

250

434

Solubility in Supercritical Carbon Dioxide

328

101 178 3.5 111 265 3.5 121 318 3.5 141 386 3.5 161 419 3.5 201 457 3.5 1: Cosolvent in CO2 on a solute-free basis. 2: The order of magnitude (105) for solubility in CO2 modified with methanol must have been misprinted in the source table (Table II) and therefore was corrected to 104 based on Figure 1. The corrected solubility values are shown in this table. Synonym: 3-Hydroxybenzoic acid Source: Gurdial, G. S.; Macnaughton, S. J.; Tomasko, D. L.; Foster, N. R. Ind. Eng. Chem. Res. (1993), 32(7), 14881497.

m-Hydroxybenzoic acid (C7H6O3; MW=138.12)

[H-72]

1)

Methanol y x 106 (mol%) 119 318 101 3.5 134 111 3.5 150 121 3.5 177 141 3.5 195 161 3.5 226 201 3.5 245 250 3.5 266 300 3.5 34 328 101 3.5 80 111 3.5 107 121 3.5 152 141 3.5 171 161 3.5 215 201 3.5 300 3.5 301 1: Cosolvent in CO2. Synonym: 3-Hydroxybenzoic acid Source: Saquing, C. D.; Lucien, F. P.; Foster, N. R. Ind. Eng. Chem. Res. (1998), 37(10), 4190-4197.

318 K 328 K

300

y x106

T (K) P (bar)

200

100

0 0

100

200

300

p-Hydroxybenzoic acid (C7H6O3; MW=138.12) y x 106 13.3 35.7 57.7 74.9

Synonym: 4-Hydroxybenzoic acid Source: Kurkonis, V. J.; Kurnik, R. T. J. Chem. Eng. Data (1985), 30(3), 247249.

[H-73] 100

y x 106

T(K) P(bar) 207 373 276 345 414

400

P (bar)

50

0 100

200

300 P (bar)

CAT4240—CHAPTER 8—31/10/2006—18:59—KADAMBADI—XML MODEL C – pp. 387–449

400

500

Solubility Data H

435

[H-74]

p-Hydroxybenzoic acid (C7H6O3; MW=138.12) T (K)

P (bar)

yx

106

4 y x 106

328 101.3 0.14 121.6 0.73 131.7 1.13 152.0 1.89 172.2 2.78 202.6 3.72 Synonym: 4-Hydroxybenzoic acid Source: Lucien, F. P.; Foster, N. R. Ind. Eng. Chem. Res. (1996), 35(12), 4686-4699.

2

0 50

150 P (bar)

250

p-Hydroxybenzoic acid (C7H6O3; MW=138.12) 313.15

100 120 210 280 290 500 1000 1500 2000

S1) (mg/Nl2)) 3.0 5.8 12.9 15.8 16.6 27.8 31.1 35.0 40.2

y3) x

[H-75]

106

0.49 0.94 2.08 2.54 2.68 4.48 5.01 5.64 6.48

8 y x 106

T(K)

P1) (bar)

4

0 0

1: Obtained by digitizing the graph in the original article. 2: "Nl" means "Normliter," which is one liter at 273.15 K and 1 atm. 3: Calculated from S. Synonym: 4-Hydroxybenzoic acid Source: Stahl, E.; Schilz, W.Talanta (1979), 26, 675-679. (Another source : Stahl, E.; Schilz, W.; Schutz, E.; Willing, E. Angew. Chem. Int. Ed. (1978), 17, 731-738.)

500

1000

1500

P (bar)

4-Hydroxybenzoic acid ethyl ester (C9H10O3; MW=166.17) T (K)

P1)

(bar)

S1) (mg/Nl2)) y3) x 106

2000

[H-76]

500

85 0.08 11 0.40 54 90 100 0.77 104 250 120 1.40 188 150 2.17 291 200 2.97 397 0 1: Obtained by digitizing the graph in 50 the original article. 2: "Nl" means "Normliter," which is one liter at 273.15 K and 1 atm. 3: Calculated from S. Synonym: Ethyl 4-hydroxybenzoate Source: Stahl, E.; Schilz, W. Talanta (1979), 26, 675-679.

y x 106

313.15

100

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150 P (bar)

200

436

Solubility in Supercritical Carbon Dioxide

4-Hydroxycoumarin (C9H6O3; MW=162.14)

[H-77]

106

1.2

308.15 K 313.15 K 323.15 K

0.8

y x 106

yx T (K) P (bar) 308.15 85 0.093 100 0.168 150 0.337 200 0.411 250 0.454 313.15 85 0.022 100 0.128 150 0.324 200 0.487 250 0.598 323.15 85 0.012 100 0.079 150 0.413 200 0.877 250 1.020 Synonym: 4-Hydroxychromen-2-one Source: Yoo, K.-P.; Shin, H. Y.; Noh, M. J.; You, S. S. Korean J. Chem. Eng. (1997), 14(5), 341-346.

0.4

0.0 0

100

200

P (bar)

[H-78]

7-Hydroxycoumarin (C9H6O3; MW=162.14) 313.15

90 100 120 150 190 200 300 500 1000 1500 2000

y3) x 106

0.0027 0.0071 0.0082 0.0089 0.0108 0.0132 0.0139 0.0189 0.0257 0.0291 0.0325

0.37 0.97 1.13 1.22 1.48 1.81 1.91 2.60 3.53 4.00 4.46

6

y x 106

T (K) P1) (bar)

S1) (mg/Nl2))

300

3

0

0

500

1: Obtained by digitizing the graph in the original article. 2: "Nl" means "Normliter," which is one liter at 273.15 K and 1 atm. 3: Calculated from S. Synonym: 7-Hydroxychromen-2-one Source: Stahl, E.; Schilz, W. Talanta (1979), 26, 675-679.

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1000 P (bar)

1500

2000

Solubility Data H

437

7-Hydroxycoumarin (C9H6O3; MW=162.14) yx 0.223 0.358 0.677 1.030 1.470 0.033 0.366 0.808 1.250 1.520 0.015 0.134 1.030 1.660 2.270

308.15 K 313.15 K 323.15 K

2 y x 106

T (K) P (bar) 308.15 85 100 150 200 250 313.15 85 100 150 200 250 323.15 85 100 150 200 250

[H-79]

106

1

0 0

100

200

300

P (bar)

Synonym: 7-Hydroxychromen-2-one Source: Yoo, K.-P.; Shin, H. Y.; Noh, M. J.; You, S. S. Korean J. Chem. Eng. (1997), 14(5), 341-346.

1-Hydroxy-2,4-dimethylanthrone (C16H14O2; MW=238.28) 308

318

P (bar)

S (g/L)

101 127 152 177 203 228 253 279 304 329 355 101 127 152 177 203 228 253 304 329 355

0.09 0.14 0.16 0.19 0.23 0.26 0.28 0.29 0.30 0.32 0.34 0.08 0.17 0.23 0.29 0.33 0.38 0.42 0.47 0.51 0.53

[H-80]

y x 106 24 32 36 41 48 53 57 58 59 63 66 30 46 56 67 74 84 90 96 103 107

270 308 K 318 K 328 K 338 K 348 K

180 y x 106

T (K)

90

0 50

150

250 P (bar)

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350

438

Solubility in Supercritical Carbon Dioxide

328

101 0.02 12 127 0.08 25 152 0.16 44 177 0.24 61 203 0.30 74 228 0.35 83 253 0.44 100 279 0.48 106 304 0.54 118 329 0.62 132 355 0.66 138 338 101 0.03 22 127 0.06 24 152 0.11 35 177 0.21 59 203 0.30 79 228 0.38 95 253 0.48 115 279 0.61 142 304 0.69 157 329 0.80 177 355 0.90 195 348 101 0.03 21 127 0.04 22 152 0.10 37 177 0.20 65 203 0.33 95 228 0.45 122 253 0.56 144 279 0.75 185 304 0.94 224 329 1.06 246 Synonym: 4-Hydroxy-1,3-dimethylanthracen-10(9H )-one Source: Karami, A. R.; Yamini, Y.; Ghiasvand, A. R.; Sharghi, H.; Shamsipur, M. J. Chem. Eng. Data (2001), 46(6), 1371-1374.

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Solubility Data H

439

1-Hydroxy-2-ethylanthrone (C16H14O2; MW=238.28) 308

318

328

338

P (bar) 101 127 152 177 203 228 253 279 304 329 355 101 127 152 177 203 228 253 279 304 329 355 101 127 152 177 203 228 253 279 304 329 355 101 127 152 177 203 228 253 279 304 329 355

S (g/L) 0.42 0.54 0.70 0.77 0.95 1.03 1.05 1.24 1.32 1.40 1.43 0.09 0.42 0.59 0.88 1.06 1.25 1.39 1.53 1.64 1.80 1.90 0.09 0.29 0.58 0.90 1.17 1.46 1.76 2.04 2.26 2.43 2.57 0.05 0.15 0.42 0.88 1.36 1.80 2.30 2.72 3.11 2.91 3.63

yx

108 127 158 169 201 214 214 248 262 274 277 34 115 147 207 240 274 297 323 340 366 380 49 96 162 233 285 341 400 450 489 517 535 31 66 139 251 361 450 555 634 705 646 790

1050 308 K 318 K 328 K 338 K 348 K

700 y x 106

T (K)

[H-81]

106

350

0 50

150

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250 P (bar)

350

440

Solubility in Supercritical Carbon Dioxide

348

101 0.04 28 127 0.09 52 152 0.34 131 177 0.78 254 203 1.34 391 228 1.82 494 253 2.50 643 279 3.12 774 304 3.68 880 329 4.20 978 Synonym: 2-Ethyl-1-hydroxyanthracen-9(10H)-one Source: Karami, A. R.; Yamini, Y.; Ghiasvand, A. R.; Sharghi, H.; Shamsipur, M. J. Chem. Eng. Data (2001), 46(6), 1371-1374.

3-Hydroxyflavone (C15H10O3; MW=238.24) y1) x 106

600

6

149 239 304 325 337 79 266 454 506 556

400

y x 10

T (K) P (bar) 308.2 91 101 152 203 253 318.2 91 101 152 203 253

[H-82]

200

0 1: The order of magnitude for solubility 50 (105) in the source table was misprinted. The solubility values shown here were obtained directly from the authors. Synonyms: Flavon-3-ol; 3-Hydroxy-2-phenylchromone Source: Uchiyama, H.; Mishima, K.; Oka, S.; Ezawa, M.; Ide, M.; Takai, T.; Park, P. W. J. Chem. Eng. Data (1997), 42(3), 570-573. (Another source : Mishima, K.; Y, S.; Ito, M.; Ezawa, M.; Tanabe, D. Solvent Extr. Res. Dev., Japan (1999), 6, 176-181.)

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308.2 K 318.2 K

150 P (bar)

250

Solubility Data H

441

2-Hydroxyhexanoic acid (C6H12O3; MW=132.16) y x 10

3000 311 K 318 K 328 K

2000 6

23 80 282 541 806 990 1100 1200 1130 1200 1120 24 245 473 935 978 1310 1390 1600 1610 29 72 262 241 523 610 713 956 1340 1700 1850 2030 2320 2610

y x 10

T (K) P (bar) 311 74 82 86 90 101 110 125 141 162 180 198 318 82 95 100 121 121 141 164 180 197 328 91 101 110 110 121 121 122 131 139 151 161 172 181 196

[H-83]

6

1000

0 50

100

Synonym: (±)-2-Hydroxycaproic acid Source: Gregorowicz, J. Fluid Phase Equil. (1999), 166(1), 39-46.

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150 P (bar)

200

442

Solubility in Supercritical Carbon Dioxide

1-Hydroxy-2-methylanthraquinone (C15H10O3; MW=238.25) T (K)

P (bar)

[H-84]

6

y x 10 S (g/L) 122 0.26 63 152 0.43 97 182 0.70 151 213 0.82 174 243 0.85 176 274 0.94 190 304 1.03 205 334 1.19 232 355 1.26 244 318 122 0.21 59 152 0.43 107 800 182 0.59 138 213 0.77 172 243 0.95 206 274 1.12 237 600 304 1.19 247 334 1.46 295 355 1.55 312 328 122 0.19 67 400 152 0.31 86 182 0.53 136 213 0.71 170 243 1.14 262 200 274 1.44 320 304 1.67 361 334 1.92 406 355 2.08 435 0 338 122 0.04 17 100 152 0.24 77 182 0.55 156 213 0.89 231 243 1.31 320 274 1.69 398 304 2.03 462 334 2.33 516 355 2.53 551 348 122 0.02 9 152 0.14 54 182 0.59 185 213 0.94 267 243 1.39 365 274 1.85 461 304 2.28 545 334 3.11 721 355 3.24 737 Source: Shamsipur, M.; Karami, A. R.; Yamini, Y.; Sharghi, H. J. Supercrit. Fluids (2004), 32(1-3), 47-53. 308

y x 106

308 K 318 K 328 K 338 K 348 K

200

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P (bar)

300

400

Solubility Data H

443

[H-85]

1-Hydroxy-2-methylanthrone (C15H12O2; MW=224.25) y x 10

87 121 150 179 181 217 231 243 251 262 260 47 84 129 164 199 225 251 274 287 299 312 24 65 115 115 219 264 303 341 371 339 431 9 34 100 167 242 322 374 439 506 549 786 50 38

900 308 K 318 K 328 K 338 K 348 K

600 6

S (g/L) 0.32 0.48 0.63 0.77 0.80 0.98 1.07 1.14 1.19 1.26 1.27 0.12 0.29 0.49 0.65 0.82 0.97 1.10 1.23 1.31 1.38 1.47 0.04 0.18 0.39 0.42 0.84 1.06 1.26 1.45 1.6? 1.50 1.95 0.01 0.07 0.29 0.55 0.86 1.21 1.46 1.77 2.10 2.33 3.41 0.06 0.06

y x 10

T (K) P (bar) 308 101 127 152 177 203 228 253 279 304 329 355 318 101 127 152 177 203 228 253 279 304 329 355 328 101 127 152 177 203 228 253 279 304 329 355 338 101 127 152 177 203 228 253 279 304 329 355 348 101 127

6

300

0 50

150

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250 P (bar)

350

444

Solubility in Supercritical Carbon Dioxide

152 0.21 86 177 0.44 151 203 0.82 254 228 1.20 347 253 1.52 415 279 1.99 523 304 2.44 620 329 2.85 705 Synonyms: 1-Hydroxy-2-methylanthracen-9(10H )-one Source: Karami, A. R.; Yamini, Y.; Ghiasvand, A. R.; Sharghi, H.; Shamsipur, M. J. Chem. Eng. Data (2001), 46(6), 1371-1374.

[H-86]

7-Hydroxy-4-methylcoumarin (C10H8O3; FW=176.17) y x 106 0.85 1.78 3.34 3.91 5.17 0.37 1.59 4.41 4.70 5.81 0.06 0.70 5.22 8.53 12.70

15 308.15 K 313.15 K 323.15 K

6

10 y x 10

T (K) P (bar) 308.15 85 100 150 200 250 313.15 313. 85 100 150 200 250 313.15 313. 85 100 150 200 250

5

0 50

150

250

P (bar)

Synonym: 7-Hydroxy-4-methyl-2 H chromen-2-one; 4-Methylumbelliferone Source: Yoo, K.-P.; Shin, H. Y.; Noh, M. J.; You, S. S. Korean J. Chem. Eng. (1997), 14(5), 341-346.

1-Hydroxy-3-methylthioxanthone (C14H10O2S; MW=242.29) T (K) P (bar) 308 121 152 182 212 243 273 304 334 354

S (g/L) 0.24 0.25 0.31 0.35 0.38 0.42 0.47 0.54 0.55

6

y x 10

57 56 65 72 76 83 92 103 104

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[H-87]

Solubility Data H

445

318

308 K 318 K 328 K 338 K 348 K

y x 106

121 0.16 45 152 0.24 59 400 182 0.33 76 212 0.40 87 243 0.49 104 273 0.55 115 300 304 0.61 125 334 0.69 138 354 0.74 147 200 328 121 0.12 41 152 0.19 52 182 0.30 76 212 0.41 96 100 243 0.50 114 273 0.64 140 304 0.72 153 334 0.81 168 0 354 0.94 193 100 338 121 0.08 36 152 0.17 53 182 0.29 81 212 0.43 111 243 0.58 140 273 0.68 15 8 304 0.88 196 334 1.01 220 354 1.10 235 348 121 0.08 43 152 0.13 49 182 0.26 80 212 0.43 121 243 0.60 156 273 0.75 185 304 1.03 242 334 1.24 282 354 1.42 318 Synonym: 1-Hydroxy-3-methylthioxanthen-9-one Source: Shamsipur, M.; Karami, A. R.; Yamini, Y.; Sharghi, H.; Salimi, A. R. J. Chem. Eng. Data (2003), 48(5), 1088-1091.

200

1-Hydroxy-3-methylxanthone (C14H10O3; MW=226.23) T (K) P (bar) 305.15 74 112 152 193 233 274 314 355 318.15 74 112

S (g/L) 1.33 2.13 2.75 3.71 4.62 5.75 6.34 6.77 0.49 1.06

y1) x 106 778 526 633 819 991 1201 1296 1359 471 340

CAT4240—CHAPTER 8—31/10/2006—18:59—KADAMBADI—XML MODEL C – pp. 387–449

300

400

P (bar)

[H-88]

446

Solubility in Supercritical Carbon Dioxide

y x 10

6

152 2.39 623 193 3.73 901 233 4.96 1140 274 6.11 1359 314 7.50 1621 355 8.32 1755 3000 305 K 328.15 74 0.17 183 318 K 112 0.57 258 152 2.41 713 328 K 193 3.31 867 338 K 233 5.16 1263 2000 348 K 274 7.98 1861 314 9.19 2069 355 9.73 2132 338.15 74 0.14 168 1000 112 0.44 259 152 1.98 686 193 3.35 961 233 4.92 1290 274 8.57 2117 0 314 9.93 2344 0 100 200 355 10.53 2406 348.15 74 0.15 196 P (bar) 112 0.52 359 152 1.43 583 193 2.95 942 233 5.14 1452 274 9.22 2413 314 10.97 2725 355 12.65 3022 1: The y value at 305.15 K and 74 bar in the source did not agree with S and thus was re-calculated based on the S value. Synonym: 1-Hydroxy-3-methyl-9H-xanthen-9-one Source: Ghiasvand, A. R.; Hosseini, M.; Sharghi, H.; Yamini, Y.; Shamsipur, M. J. Chem. Eng. Data (1999), 44(6), 11351138.

500 1400 2190 2480 2700

1: Obtained by digitizing the graph in the original article. Synonym: 1-Formyl-2-naphthol Source: Nakatani, T.; Ohgaki, K.; Katayama, T. Ind. Eng. Chem. Res. (1991), 30(6), 1362-1366.

3000 6

100 142 170 182 210

y x 10

308.15

400

[H-89]

2-Hydroxy-1-naphthaldehyde (C11H8O2; MW=172.18) 1) 1) 6 T (K) P (bar) y x 10

300

1500

0 50

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150 P (bar)

250

Solubility Data H

447

4-Hydroxypyrimidine (C4H4N2O; MW=96.09) y x 10

308.15 72.4 23.4 88.1 59.3 99.7 67.0 113.1 82.5 126.5 105.9 130.7 121.2 144.6 145.2 157.0 154.2 178.7 184.6 Synonyms: 4-Pyrimidone; 4(1H)-Pyrimidinone Source: Nakatani, T.; Tohdo, T.; Ohgaki, K.; Katayama, T. J. Chem. Eng. Data (1991), 36(3), 314-316.

200 6

P (bar)

y x 10

T (K)

[H-90]

6

100

0 50

100

150

[H-91]

8-Hydroxyquinoline (C9H7NO; MW=145.16) 5.5 9.6 12.1 14.3 16.3 17.1 1.8 10.7 15.2 18.2 24.4 1.0 10.8 18.2 24.4 29.6 34.3 1.3 9.6 19.2 27.1 39.3 47.6

y x 10

2320 3540 4210 4770 5270 5400 1090 4330 5610 6390 7960 870 4950 7260 9000 10400 11600 1400 5140 8310 10600 14400 16700

18000 308 K 318 K 328 K 338 K

12000 6

S (g/L)

6

y x 10

T (K) P (bar) 308 101 152 203 253 304 355 318 101 152 203 253 355 328 101 152 203 253 304 355 338 101 152 203 253 304 355

200

P (bar)

6000

0 50

150

Synonym: 8-Quinolinol Source: Shamsipur, M.; Ghiasvand, A. R.; Yamini, Y. J. Chem. Eng. Data (2004), 49(5), 1483-1486.

CAT4240—CHAPTER 8—31/10/2006—18:59—KADAMBADI—XML MODEL C – pp. 387–449

250 P (bar)

350

448

Solubility in Supercritical Carbon Dioxide

[H-92]

1-Hydroxythioxanthone (C13H8O2S; MW=228.27) 0.40 0.49 0.61 0.75 0.89 1.00 1.07 1.17 1.28 0.25 0.43 0.60 0.75 0.88 1.01 1.14 1.23 1.31 0.16 0.35 0.55 0.74 0.92 1.07 1.25 1.41 1.50 0.08 0.21 0.45 0.68 0.92 1.14 1.37 1.61 1.71 0.06 0.17 0.36 0.62 0.89 1.16 1.45 1.65 1.78

y x 106 99 116 138 164 192 211 221 238 259 74 112 146 175 200 222 245 261 275 61 102 147 186 222 249 283 311 328 37 72 132 184 235 280 325 372 388 33 67 120 182 246 303 361 400 424

400

308 K 318 K 328 K 338 K 348 K

6

S (g/L)

y x 10

T (K) P (bar) 308 121 152 182 212 243 273 304 334 354 318 121 152 182 212 243 273 304 334 354 328 121 152 182 212 243 273 304 334 354 338 121 152 182 212 243 273 304 334 354 348 121 152 182 212 243 273 304 334 354

200

0 100

Synonym: 1-Hydroxy-9H -thioxanthen-9-one Source: Shamsipur, M.; Karami, A. R.; Yamini, Y.; Sharghi, H.; Salimi, A. R. J. Chem. Eng. Data (2003), 48(5), 1088-1091.

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200

300 P (bar)

400

Solubility Data H

449

[H-93]

1-Hydroxyxanthone (C13H8O3; MW=212.20) T (K)

P (bar)

S (g/L)

1)

y x 10

6

305.15

305 K 318 K 328 K 338 K 348 K

y x10

6

74 0.40 249 112 0.71 188 152 1.93 475 193 2.82 665 233 3.71 846 274 4.04 899 314 4.60 1003 2500 355 5.03 1076 318.15 0.35 357 74 112 0.72 245 2000 152 1.63 453 193 2.69 693 233 3.63 889 1500 274 4.65 1102 314 5.31 1275 355 6.24 1406 1000 328.15 0.30 348 74 112 0.50 239 500 152 0.89 281 193 2.32 647 233 3.41 890 0 274 4.81 1198 314 6.11 1467 50 355 7.43 1736 338.15 0.30 384 74 112 0.43 271 152 0.70 260 193 1.78 545 233 3.16 884 274 4.86 1281 314 6.57 1654 355 7.95 1938 348.15 0.25 356 74 112 0.31 233 152 0.45 197 193 1.40 477 233 2.93 884 274 4.90 1369 314 7.00 1856 355 8.71 2220 1: The y value at 305.15 K and 74 bar in the source did not agree with S and thus was re-calculated based on the S value. Synonym: 1-Hydroxy-9H-xanthen-9-one Source: Ghiasvand, A. R.; Hosseini, M.; Sharghi, H.; Yamini, Y.; Shamsipur, M. J. Chem. Eng. Data (1999), 44(6), 1135-1138.

150

CAT4240—CHAPTER 8—31/10/2006—18:59—KADAMBADI—XML MODEL C – pp. 387–449

250 P (bar)

350

9

Solubility Data I

Imipramine hydrochloride (C19H24N2·ClH; FW=316.87)

323.15

P (bar) 300 350 400 450 500 300 350 400 450 500

6.4 7.6 9.0 9.9 5.1 6.1 8.8 8.2 8.0 6.4

12

y x 106

T (K) 313.15

[I-1]

y x 106

313 K 323 K

8

4 250

350

450

Indium tris(acetylacetonate) (C15H21InO6; FW=412.15) (bar)

S1)

(mg/L)

y2)

x

106

100 0.03 0.011 200 0.95 0.139 300 2.32 0.298 1: Obtained by digitizing from the original article. 2. Calculated from S. Synonym: Tris(2,4-pentanedionato)indium Source: Saito, N.; Ikushima, Y.; Goto, T. Bull. Chem. Soc. Japan (1990), 63(5), 1532-1534.

[I-2]

0.4 y x 106

T (K) 333

P1)

550

P (bar)

Synonym: 5-[3-(Dimethylamino)propyl]10,11-dihydro-5H-dibenz[b,f]azepine Hydrochloride Source: Jara-Morante, E.; Suleiman, D.; Estevez, L. A. Ind. Eng. Chem. Res.(2003), 42(8), 1821-1823.

0.2 0 50

150

250

350

P (bar)

451

CAT4240—CHAPTER 9—31/10/2006—18:57—MUGUNTHAN—XML MODEL C – pp. 451–454

452

Solubility in Supercritical Carbon Dioxide

Indole (C8H7N; MW=117.15)

[I-3]

106

6000

y x 106

T (K) P (bar) y x 308.15 53.8 188 64.3 204 75.2 424 85.4 2890 96.0 3400 105.0 3810 116.6 4290 134.5 4670 146.5 4890 162.3 5200 184.0 5470 207.5 5750 Synonyms: 1H-Indole; 2,3-Benzopyrrole Source: Sako, S.; Ogaki, K.; Katayama, T. J. Supercrit. Fluids (1988), 1(1), 1-6.

3000

0

50

100

150 P (bar)

Iron tris(acetylacetonate) (C15H21FeO6; FW=353.17) 313

323

P (bar)

S (g/L)

98.2 106.3 117.4 124.6 138.8 147.0 160.1 167.7 180.0 189.2 199.5 217.6 245.5 247.8 269.2 275.4 295.0 298.2 323.6 328.0 353.7 119.9 126.8 134.6 147.5 163.1 163.5 170.0 183.3

0.28 0.47 0.66 0.72 0.79 0.95 1.14 1.13 1.23 1.28 1.39 1.50 1.59 1.67 1.74 1.79 1.90 1.85 1.96 1.97 2.05 0.32 0.31 0.55 0.51 0.74 0.75 0.65 0.84

yx

[I-4]

106

60 90 120 120 130 150 180 170 190 190 210 220 230 240 240 250 260 250 260 270 270 70 60 100 90 130 130 110 140

313 K 323 K 333 K

300

y x 106

T (K)

200

200

100

0

50

150

CAT4240—CHAPTER 9—31/10/2006—18:57—MUGUNTHAN—XML MODEL C – pp. 451–454

250 P (bar)

350

Solubility Data I

189.6 205.6 212.5 228.9 238.0 249.2 249.9 265.5 271.3 296.5 296.7 323.6 334.0 348.6 127.6 147.7 166.9 187.4 207.4 228.2 247.8

453

0.80 0.92 0.92 1.04 1.02 1.14 1.19 1.14 1.29 1.36 1.28 1.39 1.36 1.46 0.24 0.56 0.91 1.21 1.51 1.74 1.91

130 150 140 160 150 170 180 170 190 190 180 200 190 200 333 60 120 170 210 260 280 300 Synonyms: Fe(acac)3; Tris(2,4-pentanedionato)iron Source: Andersen, W. C.; Sievers, R. E.; Lagalante, A. F.; Bruno, T. J. J. Chem. Eng. Data (2001), 46(5), 1045-1049.

Iron tris(acetylacetonate) (C15H21FeO6; FW=353.17) P (bar)

313.15

90.1 137.9 172.4 206.9 237.9 275.8 90.1 137.9 172.4 206.9 237.9 275.8 137.9 172.4 206.9 237.9 275.8

333.15

333.15

(mol %) 0 0 0 0 0 0 0 0 0 0 0 0 3 3 3 3 3

[I-5]

y x 106 31 155 207 263 290 317 9 120 241 357 472 576 433 733 978 1210 1340

1500 CO2, 313 K CO2, 333 K CHCl3, 333 K

1000 y x 106

T (K)

CHCl31)

500

0 50

1 : Cosolvent in CO2. Synonyms: Fe(acac)3; Tris(2,4-pentanedionato)iron Source: Roggeman, E. J. ; Scurto, A. M. ; Brennecke, J. F. Ind. Eng. Chem. Res. (2001), 40(3), 980-989.

CAT4240—CHAPTER 9—31/10/2006—18:57—MUGUNTHAN—XML MODEL C – pp. 451–454

150 P (bar)

250

454

Solubility in Supercritical Carbon Dioxide

Iron tris(2,2,6,6-tetramethyl-3,5-heptanedionate) (C33H57FeO6; FW=605.65) 313

323

333

P (bar) 94.8 104.0 123.6 145.4 173.0 200.4 241.5 122.7 144.4 172.5 202.0 243.7 306.7 138.8 142.2 157.1 163.0 184.8

[I-6]

y x 106 1640 2300 3400 4240 4940 5340 5600 2990 3720 4340 4690 4820 5850 3910 4700 8700 7880 10130

12000 313 K 323 K 333 K

8000 y x 106

T (K)

4000

0 50

150 250 P (bar)

350

Synonyms: Fe(thd)3; Tris(2,2,6,6tetramethyl-3,5-heptanedionato)iron Source: Andersen, W. C.; Sievers, R. E.; Lagalante, A. F.; Bruno, T. J. J. Chem. Eng. Data (2001), 46(5), 1045-1049.

Iron tris(2,2,7-trimethyl-3,5-octanedionate) (C33H57FeO6; FW=605.65) P (bar) y x 106 90.6 1750 93.1 2640 107.5 5480 112.8 6480 121.6 8500 147.5 10320 323 111.0 1390 124.6 4130 127.9 4750 139.1 6200 144.7 8250 165.0 10300 333 131.1 1550 144.6 3710 152.3 5020 159.0 6820 161.8 7750 166.3 8600 177.4 12670 Synonyms: Fe(tod)3; Tris(2,2,7-trimethyl3,5-octanedionato)iron Source: Andersen, W. C.; Sievers, R. E.; Lagalante, A. F.; Bruno, T. J. J. Chem. Eng. Data (2001), 46(5), 1045-1049. T (K) 313

[I-7]

15000 313 K 323 K 333 K

y x 106

10000

5000

0

50

100 150 P (bar)

CAT4240—CHAPTER 9—31/10/2006—18:57—MUGUNTHAN—XML MODEL C – pp. 451–454

200

10

Solubility Data J

Jojoba bean oil1) 345.15

P (bar)

yx

345 1740 552 88500 690 75160 1: Extract of Simmondsia chinensis nuts. Synonym: Jojoba wax Source: Eissler, R.; Friedrich, J. P. J. Am. Oil Chem. Soc. (1988), 65(5), 764-767.

100000 y x 106

T (K)

[J-1] 106

50000 0 200

400

600

800

P (bar)

455

CAT4240—CHAPTER 10—31/10/2006—19:04—MUGUNTHAN—XML MODEL C – pp. 455

11

Solubility Data K

Ketoprofen (C16H14O3; MW=254.28) 200 312.5 K 331.5 K

y x 106

y x 106 T (K) P (bar) 312.5 100 13.3 130 29.0 160 51.4 190 72.0 220 79.8 331.5 116 7.8 130 16.3 160 55.0 190 105.0 220 155.0 Synonyms: m-Benzoylhydratropic acid; 2-(3-Benzoylphenyl)propionic acid Source: Macnaughton, S. J.; Kikic, I.; Foster, N. R.; Alessi, P.; Cortesi, A.; Colombo, I. J. Chem. Eng. Data (1996), 41(5), 1083-1086.

[K-1]

100

0 50

150 P (bar)

Ketoprofen (C16H14O3; MW=254.28) 313

328

P (bar) 90 100 110 130 150 200 250 110 130 150 170 190 210

[K-2]

y x 106 3.9 13.9 21.2 55.2 63.2 87.8 91.5 3.3 16.6 46.6 70.3 103.0 133.0

200 313 K 328 K

150 y x 106

T (K)

250

100 50 0 50

150

250

P (bar)

457

CAT4240—CHAPTER 11—31/10/2006—19:13—KADAMBADI—XML MODEL C – pp. 457–459

458

Solubility in Supercritical Carbon Dioxide

230 250

161.0 188.0

Synonyms: m-Benzoylhydratropic acid; 2-(3-Benzoylphenyl)propionic acid Source: Stassi, A.; Bettini, R.; Gazzaniga, A.; Giordano, F.; Schiraldi, A. J. Chem. Eng. Data (2000), 45(2), 161-165.

Ketoprofen (C16H14O3; MW=254.28)

[K-3]

y x 106 T (K) P (bar) 313 95 4.8 103 15.5 130 53.5 147 63.0 198 89.9 249 98.5 Synonyms: m-Benzoylhydratropic acid; 2-(3-Benzoylphenyl)propionic acid Source: Weinstein, R. D.; Muske, K. R.; Moriarty, J.; Schmidt, E. K. J. Chem. Eng. Data (2004), 49(3), 547-552.

y x 106

100

50

0 50

150

250

P (bar)

[K-4]

Krytox dithiol1) wx

44100 37200 31200 26900 23700 21200

1: Prepared from DuPont's Krytox FSL functional oil, consisting of oligomers of hexafluoropropylene oxide capped with carboxylic acid group, via reaction with thionyl chloride, followed by reaction with 2,3-dithio-1-propanol. Source: Yazdi, A. ; Beckman, E. J. Mat. Res. Soc. Symp. Proc. (1994), 344, 211-216.

50000

w x 106

P (bar) T (K) 298.15 64.9 67.7 68.4 70.1 71.3 72.7

106

30000

10000 60

CAT4240—CHAPTER 11—31/10/2006—19:13—KADAMBADI—XML MODEL C – pp. 457–459

65

70 P (bar)

75

Solubility Data K

459

Krytox picolyl amine1) w x 106 25900 34700 41900 59500 69200 46600 83000 52300

1: Prepared from DuPont's Krytox FSL functional oil, consisting of oligomers of hexafluoropropylene oxide capped with carboxylic acid group, via reaction with thionyl chloride, followed by reaction with picolyl amine. Source: Yazdi, A. ; Beckman, E. J. Mat. Res. Soc. Symp. Proc. (1994), 344, 211-216.

100000

w x 106

P (bar) T (K) 298.15 97.5 101.8 101.8 104.4 104.4 104.5 105.8 106.4

[K-5]

50000

0 95

100

CAT4240—CHAPTER 11—31/10/2006—19:13—KADAMBADI—XML MODEL C – pp. 457–459

105 P (bar)

110

12

Solubility Data L

Lactic acid (C3H6O3; MW=90.08)

[L-1]

6

313 K 318 K 328 K

6

1500

y x 10

y x 10 T (K) P (bar) 313 58 32 85 153 92 449 102 734 110 883 123 1040 140 1150 160 1300 179 1270 196 1390 318 70 38 81 71 91 192 100 503 120 1110 142 1330 166 1480 166 1530 182 1600 328 71 24 89 55 101 183 111 439 120 664 132 1010 152 1360 170 1620 186 1700 197 1690 Synonym: 2-Hydroxypropanoic acid Source: Gregorowicz, J. Fluid Phase Equil. (1999), 166(1), 39-46.

1000

500

0 50

100

150

200

P (bar)

461

CAT4240—CHAPTER 12—1/11/2006—16:07—SRIDHAR—XML MODEL C – pp. 461–475

462

Solubility in Supercritical Carbon Dioxide

[L-2]

Lariat ether carboxylic acid T (K)

P (bar)

M x 106 (mol/L)

1)

6

y x 10

2)

Ring-fluorinated lariat ether carboxylic acid 323.15 101 7.9 0.86 119 84.0 6.34 152 99.0 6.16 203 120.0 6.69 304 210.0 10.57

3)

Fluorine-containing lariat ether carboxylic acid 323.15 101 30.0 3.28 119 90.0 6.79 152 130.0 8.09 203 160.0 8.92 304 210.0 10.57

8

y x 10

6

12

4

Non-fluorinated lariat ether carboxylic acid4) 0 323.15 101 7.6 0.83 50 119 22.0 1.66 152 76.0 4.73 203 120.0 6.69 304 210.0 10.57 1: Calculated from M. 2: sym -3(6),3'(6')-Difluorodibenzo-16-crown-5oxyacetic acid (C21H22F2O8; MW=440.40). 3: sym -[3,5-Di(trifluoromethyl)phenyl]dibenzo-16crown-5-oxyacetic acid (C29H26F6O8; MW=616.51). 4: sym -Dibenzo-16-crown-5-oxyacetic acid (C21H24O8; MW=404.42). Source: Elshani, S.; Du, H.; Laintz, K. E.; Natale, N. R.; Wai, C. M.; Elkarim, N. S. A.; Bartsch, R. A. Tetrahedron (2000), 56(27), 4651-4657.

Ring-fluorinated Fluorine-containing Non-fluorinated

150

250 P (bar)

[L-3]

Lasalocid sodium salt (C34H53NaO8; FW=612.78)

6

14 y x 10

Methanol T (K) P (bar) y x 106 (wt%) 1 6.95 353.15 152 1 3.68 207 1 3.98 279 1 6.44 344 1 7.22 382 390 1 12.30 Source: Maxwell, R.; Hampson, J.; Cygnarowicz-Provost, M. J. Supercrit. Fluids (1992), 5(1), 31-37.

350

7

0 100

CAT4240—CHAPTER 12—1/11/2006—16:07—SRIDHAR—XML MODEL C – pp. 461–475

200

300 P (bar)

400

Solubility Data L

463

[L-4]

Lauric acid (C12H24O2; MW=200.32) 6

P (bar) y x 10 T (K) 313 77 0.4 81 23.6 81 6.0 91 678.0 110 4060.0 150 11000.0 150 10800.0 151 11100.0 200 24800.0 248 57300.0 Synonym: Dodecanoic acid Source: Bamberger, T.; Erickson, J. C.; Cooney, C. L.; Kumar, S. K. J. Chem. Eng. Data (1988), 33(3), 327-333.

y x 10

6

60000

30000

0 50

150

250

P (bar)

Lauric acid (C12H24O2; MW = 200.32) W (g/kg CO2)

100000

y1) x 106

308

139 42 9100 269 340 69500 318 142 30 6500 207 450 90000 1: Calculated from W. Synonym: Dodecanoic acid Source: Maheshwari, P.; Nikolov, Z.; White, T.; Hartel, R. J. Am. Oil Chem. Soc. (1992), 69(11), 1069-1076.

308 K 318 K

6

P (bar)

y x 10

T (K)

[L-5]

50000

0 100

150

200

T (K) 323.15

P (bar) 150 200 250 300 350 400

M x 10 (mol/L)

y x 10

14.0 32.0 34.1 44.8 58.5 67.5

8.8 17.9 17.9 22.6 28.6 32.1

1)

6

CAT4240—CHAPTER 12—1/11/2006—16:07—SRIDHAR—XML MODEL C – pp. 461–475

300

P (bar)

Lead bis(diisopropyldithiocarbamate) (C14H28N2PbS4; FW=559.83) 5

250

[L-6]

464

Solubility in Supercritical Carbon Dioxide

333.15

150 5.0 3.6 200 20.0 12.1 250 34.7 19.4 300 49.3 26.1 350 71.1 36.2 400 75.5 37.3 343.15 150 6.2 5.3 200 22.8 15.2 250 46.6 27.7 300 65.2 36.3 350 92.9 49.4 400 139.2 71.4 1: Calculated from M. Synonym: Bis(diisopropyldithiocarbamato)lead Source: Wenclawiak, B. W.; Wolf, A.; Wilnewski, S. in: Supercritical Fluids as Solvents and Reaction Media, Brunner, G. (ed.), Elsevier B. V., Amsterdam, Netherlands (2004), 323-340. (Another source : Wolf, A.: Sc.D. Thesis, Siegen University, Germany, 1999.)

80 323.15 K 333.15 K 343.15 K

y x 10

6

60

40

20

0 100

250

400

P (bar)

Lecithin S201)

323

150 200 250 300 330 150 200 250 300 330 150 200 250 300 330 150 200 250 300 330 150 200 250 300

2)

Ethanol (wt%)

5 5 5 5 5 7 7 7 7 7 10 10 10 10 10 5 5 5 5 5 7 7 7 7

W 3) (g/kg CO2) 0.09 0.03 0.08 0.73 1.45 0.20 0.07 0.38 1.27 1.45 0.23 0.04 0.24 0.96 2.00 0.05 0.04 0.99 1.80 2.94 0.18 0.12 0.16 3.29

4)

6

w x 10

86 29 76 700 1380 190 65 355 1190 1350 210 36 218 872 1820 48 38 940 1710 2790 170 110 150 3070

4000

3000

6

313

P(bar)

w x 10

T(K)

[L-7]

2000

313 K 313 K 313 K 323 K 323 K 323 K 333 K 333 K 333 K

5% 7% 10% 5% 7% 10% 5% 7% 10%

1000

0 100

CAT4240—CHAPTER 12—1/11/2006—16:07—SRIDHAR—XML MODEL C – pp. 461–475

200 P (bar)

300

Solubility Data L

333

465

150 200 250 300 330

10 10 10 10 10

0.21 0.71 0.51 2.64 3.21

190 650 460 2390 2910

150 200 250 300 330 150 200 250 300 330 150 200 250 300 330

5 5 5 5 5 7 7 7 7 7 10 10 10 10 10

0.13 0.43 0.93 3.13 3.72 0.03 0.05 2.16 3.61 4.25 1.59 0.74 1.30 2.56 3.87

120 410 880 2970 3530 28 47 2020 3360 3960 1440 670 1180 2320 3510

1: Product of Lipoid KG, Germany, that contains phosphatidylethanolamine (20-23%), phosphatidylinositol (10-14%), and phosphatidylethanolamine (13-16%). 2: Cosolvent in CO2. 3: The total amount of phospholipids (phosphatidylcholine, phosphatidylinositol and phosphatidylethanolamine). 4: Calculated from W. Source: Badens, E.; Magnan, C.; Charbit, G. Biotech. Bioeng. (2000), 72(2), 194-204.

(C6H13NO2; MW=131.17) 0.10 6

T (K) P1) (bar) S1)(μg/Nl2)) y3) x 106 313.15 300 0.26 0.044 500 0.32 0.054 1000 0.44 0.075 1500 0.50 0.084 2000 0.52 0.089 1: Obtained by digitizing the graph in the original article. 2: "Nl" means "Normliter," which is one liter at 273.15 K and 1 atm. 3: Calculated from S. Synonyms: (S)-2-Amino-4-methylpentanoic acid; 4-Methyl-L-norvaline Source: Stahl, E.; Schilz, W. Chem. Ing. Tech. (1978), 50(7), 535-537.

[L-8]

y x 10

L-Leucine

0.06

0.02 0

CAT4240—CHAPTER 12—1/11/2006—16:07—SRIDHAR—XML MODEL C – pp. 461–475

1000 P (bar)

2000

466

Solubility in Supercritical Carbon Dioxide

Lidocaine (C14H22N2O; MW=234.34)

[L-9]

6

300 298 K 308 K 318 K

200 y x 10

6

y x 10 T (K) P (bar) 298 70 74.4 74 75.9 89 83.0 100 79.0 114 87.4 124 108.0 143 132.0 156 154.0 177 187.0 195 222.0 248 275.0 308 78 15.5 85 25.7 89 31.1 99 32.0 123 35.3 146 38.8 166 55.9 175 66.7 197 90.7 212 108.0 234 132.0 248 163.0 318 75 33.3 85 29.1 100 31.4 122 39.2 148 40.9 176 68.8 197 97.8 221 138.0 234 162.0 252 197.0 Synonyms: 2-(Diethylamino)-2',6'-acetoxylidide; 2 (Diethylamino)-N-(2,6-dimethylphenyl)acetamide Source: Weinstein, R. D.; Muske, K. R.; Moriarty, J.; Schmidt, E. K. J. Chem. Eng. Data (2004), 49(3), 547-552.

100

0 0

CAT4240—CHAPTER 12—1/11/2006—16:07—SRIDHAR—XML MODEL C – pp. 461–475

100

200 P (bar)

300

Solubility Data L

467

Limonene (C10H16 ; MW=136.23)

[L-10]

6

313 K 323 K 333 K

6

30000

y x 10

y x 10 T (K) P (bar) 313 70.4 400 74.6 400 77.9 1200 79.6 2900 81.5 32000 323 71.1 800 78.1 1600 84.7 3500 89.7 3600 91.2 4300 93.1 8100 95.6 9500 333 72.9 600 76.0 900 80.0 1900 91.1 2400 95.4 4300 99.7 5100 104.9 6400 107.3 6300 109.5 11000 112.0 17400 Synonyms: 4-Isopropenyl-1-methyl-1cyclohexene; p-Mentha-1,8-diene Source: Akgun, M.; Akgun, N. A.; Dincer, S. J. Supercrit. Fluids (1999), 15, 117-125.

20000

10000

0 60

80

100

[L-11]

Limonene (C10H16 ; MW=136.23) 6

P (bar) w x 10 y x 10 T (K) 315 30.5 600 194 40.7 1200 388 50.8 1800 582 61.0 2500 809 71.2 4000 1300 81.3 7000 2270 83.9 10800 3510 85.0 18000 5890 1: Calculated from w. Synonyms: 4-Isopropenyl-1-methyl-1cyclohexene; p -Mentha-1,8-diene Source: Benvenuti, F.; Gironi, F. J. Chem. Eng. Data (2001), 46(4), 795-799.

7000 6

1)

y x 10

6

120

P (bar)

3500

0 0

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50 P (bar)

100

468

Solubility in Supercritical Carbon Dioxide

Limonene (C10H16; MW=136.23)

[L-12]

6

6

300000 y x 10

y x 10 T (K) P (bar) 318.2 69 1700 76 2410 81 3940 85 9530 90 22920 95 108300 100 173200 105 279700 Synonyms: 4-Isopropenyl-1-methyl-1cyclohexene; p-Mentha-1,8-diene Source: Berna, A.; Chafer, A.; Monton, J. B. J. Chem. Eng. Data(2000), 45(5), 724-727.

200000 100000 0 50

70

90

[L-13]

Limonene (C10H16 ; MW=136.23) T (K)

P (bar)

110

P (bar)

6

y x 10

313.8

16000 313.8 K 323.2 K 333.3 K

6

12000 y x 10

8.3 500 14.7 300 27.1 1100 45.1 2600 65.6 4700 75.6 5700 79.4 6700 84.5 7900 323.2 11.3 900 21.6 1500 31.6 2000 41.8 3100 51.8 4000 62.5 4500 72.8 5800 82.7 7200 89.3 8300 96.9 10300 98.3 15000 333.3 41.3 3900 67.3 4800 84.3 6300 93.0 6600 96.2 6800 99.2 8000 102.9 11200 107.7 12900 110.0 13600 Synonyms: 4-Isopropenyl-1-methyl-1cyclohexene; p-Mentha-1,8-diene Source: Chang, C.-M. J.; Chen, C.-C. Fluid Phase Equil. (1999), 163, 119-126.

8000

4000

0 0

CAT4240—CHAPTER 12—1/11/2006—16:07—SRIDHAR—XML MODEL C – pp. 461–475

40

80 P (bar)

120

Solubility Data L

469

[L-14]

Limonene (C10H16; MW=136.23) 6

308.2 K 315.0 K 323.2 K

y x 10

6

P (bar) y x 10 T (K) 308.2 30 220 40 290 50 390 60 610 70 830 50000 73 1970 75 31300 315.0 30 350 40 390 50 570 60 790 70 1270 25000 80 2460 83 3490 84 5930 85 42900 323.2 30 530 40 570 0 50 790 60 930 0 70 1510 80 2220 85 3090 90 4090 95 5020 100 43800 Synonyms: 4-Isopropenyl-1-methyl-1cyclohexene; p-Mentha-1,8-diene Source: Di Giacomo, G.; Brandani, V.; Del Re, G.; Mucciante, V. Fluid Phase Equil. (1989), 52. 405-411.

50 P (bar)

[L-15]

Limonene (C10H16; MW=136.23) 6

1) P (bar) S (g/L) y x 10 313.15 80 0.026 4550 100 0.084 14500 150 0.143 24500 250 0.164 28000 333.15 80 0.017 2980 100 0.057 9910 150 0.095 16400 250 0.122 21000 1: Obtained by digitizing the graph in the original article. 2: Solubility is based on 1liter of CO2 at 293.15K and 1 atm. 3: Calculated from S. Synonyms: 4-Isopropenyl-1-methyl-1cyclohexene; p-Mentha-1,8-diene Source: Francisco, J. C.; Sivik, B. J. Supercrit. Fluids (2002), 23(1), 11-19.

T (K)

30000

6

3)

y x 10

1,2)

100

20000 10000

313.15 K 333.15 K

0 50

CAT4240—CHAPTER 12—1/11/2006—16:07—SRIDHAR—XML MODEL C – pp. 461–475

150 P (bar)

250

470

Solubility in Supercritical Carbon Dioxide

[L-16]

Limonene (C10H16; MW=136.23) 6

L-Limonene

15000 313.5 K 323.5 K

6

10000 y x 10

y x 10 T (K) P (bar) 313.15 70.0 1440 72.0 1230 75.0 1900 77.0 2160 78.8 2920 80.0 3200 81.0 3960 81.7 4310 323.15 70.0 1740 75.0 1830 83.8 2850 86.0 3450 87.2 3830 90.0 4850 92.1 5940 92.3 6580 93.0 6830 95.6 10800 95.9 11900 Synonyms: 4-Isopropenyl-1-methyl-1cyclohexene; p-Mentha-1,8-diene Source: Sovova, H.; Zarevucka, M.; Vacek, M.; Stransky, K. J. Supercrit. Fluids (2001), 20(1), 15-28.

5000

0 60

80

100

P (bar)

[L-17]

(C10H16; MW=136.23) 6

6

30000

y x 10

y x 10 T (K) P (bar) 312.15 62.1 929 68.9 1630 75.8 3140 79.3 5090 81.0 6686 82.7 26000 322.15 62.1 839 68.9 1551 75.8 2473 82.7 3857 89.6 6806 91.4 9971 93.1 22160 Synonyms: (4S )-4-Isopropenyl-1-methyl1-cyclohexene; (S)-(−)-p-Mentha-1,8diene Source: Kim, K. H.; Hong, J. Fluid Phase Equil. (1999), 164(1), 107-115.

312.15 K 322.15 K

20000

10000

0 60

CAT4240—CHAPTER 12—1/11/2006—16:07—SRIDHAR—XML MODEL C – pp. 461–475

80 P (bar)

100

Solubility Data L

471

Limonene (C10H16; MW=136.23) T (K)

P (bar)

Ethane 6 y1 x 10 (mol %) 0.0 4000 0.0 3000 0.0 9000 0.0 7000 0.0 8000 0.0 16000 0.0 6000 0.0 4000 0.0 6000 0.0 9000 0.0 13000 0.0 15000 0.0 15000 0.0 33000 23.2 9000 23.2 9000 23.2 14000 23.2 17000 23.2 27000

40000

86.0 87.0 87.0 88.0 30000 89.0 90.0 323.2 87.0 20000 91.0 94.0 95.0 96.0 10000 97.0 97.5 98.0 0 303.2 67.0 60 68.0 69.5 70.5 71.0 1: Cosolvent in CO2. Synonyms: 4-Isopropenyl-1-methyl-1cyclohexene; p-Mentha-1,8-diene Source: Matos, H. A.; de Azevedo, E. G.; Simoes, P. C.; Carrondo, M. T.; da Ponte, N. M. Fluid Phase Equil. (1989), 52, 357-364. 6

CO2 318.2 K CO2 323.2 K w/Eth 303.2 K

y x 10

318.2

[L-18]

1)

80 P (bar)

[L-19]

Limonene (1) + Citral (C10H16O; MW=152.23) (2) Mixture T (K)

P (bar)

x11)

6

y1 x 10

6

y2 x 10

Limonene Citral x 1= 0.755

6

y x 10

94.9 0.775 3850 230 95.0 0.972 4560 50 96.5 0.776 3810 230 100.0 0.028 130 1220 0.779 14600 3170 100.0 1: Mole fraction of limonene in the liquid phase (solvent-free basis). Synonym of (2): 3,7-Dimethyl-2,6-octadienal Source: Di Giacomo, G.; Brandani, V.; Del Re, G.; Mucciante, V. Fluid Phase Equil. (1989), 52. 405-411.

16000

323.2

100

8000

0 94

CAT4240—CHAPTER 12—1/11/2006—16:07—SRIDHAR—XML MODEL C – pp. 461–475

97 P (bar)

100

472

Solubility in Supercritical Carbon Dioxide

Limonene (1) + Linalool (2) Mixture 1) 6

[L-20]

6

Limo 318 K, 40:60 Limo 318 K, 60:40 Limo 328 K, 60:40 Lina 318 K, 40:60 Lina 318 K, 60:40 Lina 328 K, 60:40

y x 10

6

y2 x 10 T (K) P (bar) y1 x 10 Limonene(40 wt%) + Linalool(60 wt%) 120000 318.15 70 4000 3100 74 6400 6900 78 7600 9800 82 12800 16700 86 24200 33900 90 53600 76000 80000 Limonene(60 wt%) + Linalool(40 wt%) 318.15 70 3600 1000 74 4200 1500 78 4800 1900 82 10100 6700 86 24200 15200 40000 90 65500 40700 328.15 70 8000 4000 74 8200 4000 78 8300 4100 82 8900 4600 0 86 10000 5300 90 13000 6200 60 95 20700 7400 100 30600 15200 105 45800 25200 110 97500 43600 1: Solubility of each component was measured from the mixture. Source: Chafer, A.; Berna, A.; Monton, J. B.; Mulet, A. J. Chem. Eng. Data (2001), 46(5), 1145-1148.

80

100 P (bar)

[L-21]

Linalool (C10H18O; MW=154.25) 6

6

300000

y x 10

y x 10 T (K) P (bar) 318.2 71 680 77 1050 84 2530 91 17400 96 282600 328.2 71 690 79 800 85 1390 91 1990 96 3390 100 30390 106 104200 111 212700 Synonym: 3,7-Dimethyl-1,6-octadien-3-ol Source: Berna, A.; Chafer, A.; Monton, J. B. J. Chem. Eng. Data (2000), 45(5), 724-727.

120

318.2 K 328.2 K

200000

100000

0 60

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80

100 P (bar)

120

Solubility Data L

473

Linalool (C10H18O; MW=154.25)

[L-22]

6

12000 313.2 K 323.3 K 333.2 K

6

8000 y x 10

y x 10 T (K) P (bar) 313.2 8.1 300 15.2 500 22.0 1000 28.1 1500 42.4 2400 61.7 3000 70.8 5000 76.4 5700 323.3 7.8 800 14.4 900 21.1 1500 27.9 1900 34.6 2400 48.3 3500 54.7 4000 61.8 4600 69.0 5300 81.3 6800 95.0 8700 102.0 10000 333.2 22.6 500 42.0 1000 62.1 1200 91.5 2200 95.8 2200 100.2 3600 104.2 3800 108.1 6900 110.6 8600 Synonym: 3,7-Dimethyl-1,6-octadien-3-ol Source: Chang, C.-M. J.; Chen, C.-C. Fluid Phase Equil. (1999), 163, 119-126.

4000

0 0

40

80

120

P (bar)

Lindane (C6H6Cl6; MW=290.83)

[L-23]

6

6

3000

y x 10

y x 10 T (K) P (bar) 313.1 100 544 130 1040 160 1420 190 1720 220 1960 333.1 100 51 130 510 160 1320 190 2140 220 2690 Synonyms: g -BHC; g -1,2,3,4,5,6Hexachlorocyclohexane Source: Macnaughton, S. J.; Kikic, I.; Rovedo, G.; Foster, N. R.; Alessi, P. J. Chem. Eng. Data (1995), 40(3), 593-597.

313.1 K 333.1 K

2000 1000 0 50

CAT4240—CHAPTER 12—1/11/2006—16:07—SRIDHAR—XML MODEL C – pp. 461–475

150 P (bar)

250

474

Solubility in Supercritical Carbon Dioxide

Linoleic acid (C18H32O2; MW= 280.45) T (K)

P(bar)

[L-24]

6

y x 10

313

313 K 333 K

2000

6

1500 y x 10

99.4 300 118.8 500 137.3 700 157.5 900 177.7 1100 197.4 1200 210.7 1500 222.0 1700 231.8 1700 241.0 2000 333 54.2 100 80.0 200 105.9 200 131.4 400 157.8 700 180.2 700 196.0 800 210.6 1000 226.8 1300 240.6 1500 Synonym: (Z ,Z )-9,12-Octadecadienoic acid Source: Chen, C.-C.; Chang, C.-M. J.; Yang, P.-W. Fluid Phase Equilibria (2000), 175(1-2), 107-115.

1000 500 0 0

100

200 P (bar)

Linoleic acid (C18H32O2; MW= 280.45) T (K)

P (bar)

W (g/kg CO2)

[L-25] 5000

y1) x 106

313 K 323 K 333 K 6

313

y x 10

138 4.5 705 207 22.0 3440 276 26.0 4060 323 138 2.7 420 207 16.0 2500 276 27.0 4220 333 138 1.1 173 206 18.0 2820 276 19.0 2970 1: Calculated from W. Synonym: (Z,Z)-9,12-Octadecadienoic acid Source: Maheshwari, P.; Nikolov, Z.; White, T.; Hartel, R. J. Am. Oil Chem. Soc. (1992), 69(11), 1069-76. (Another source : Nikolov, Z.; Maheshwari, P.; Hardwick, J.; Murphy, P.; Johnson, L. Dev. Food Sci. (1992), 29, 595-616).

300

2500

0 100

CAT4240—CHAPTER 12—1/11/2006—16:07—SRIDHAR—XML MODEL C – pp. 461–475

200 P (bar)

300

Solubility Data L

475

[L-26]

Lipids1) T (K)

P (bar) W2)(g/kg CO2) w3) x 106

6

313.15 K 333.15 K

w x 10

150 1.2 1200 225 3.3 3290 300 7.4 7350 333.15 150 0.3 300 225 2.6 2590 300 5.9 5870 1: Lipids that were extracted from frying oil (hydrogenated soybean oil). 2: Mass solubility in CO2 (solute-free basis). 3: Calculated from W. Source: Yoon, J.; Han, B.-S.; Kang, Y.- C.; Kim, K. H.; Jung, M. Y.; Kwon, Y. A. Food Chem. (2000), 71(2), 275-279.

8000

313.15

4000

0 100

200

300

P (bar)

[L-27]

Lithium acetylacetonate (C5H7LiO2; FW=106.05) P (bar) S (mg/L) T (K) 333 98 0.0056 196 0.0113 294 0.0199

2)

6

y x 10

0.00831 0.00653 0.00998

1: Obtained by digitizing the graph in the original article. 2. Calculated from S. Synonyms: Bis(2,4-pentanedionato) lithium; Li(acac) Source: Saito, N.; Ikushima, Y.; Goto, T. Bull. Chem. Soc. Japan (1990), 63(5), 1532-1534.

0.012 6

1)

y x 10

1)

0.008 0.004 50

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150

250 P (bar)

350

13

Solubility Data M

[M-1]

Mandelic acid (C8H8O3; MW=152.15)

308.15 K 318.15 K 328.15 K

y × 106

y × 106 T (K) P (bar) 308.15 101.0 93 3000 121.6 195 140.3 326 163.0 528 189.2 912 207.1 1114 2000 228.5 1243 318.15 102.3 36 120.9 141 141.6 320 163.0 604 1000 183.7 970 205.0 1366 225.7 1794 328.15 104.4 27 124.4 109 0 143.0 303 50 163.7 666 185.1 1194 205.7 2010 230.6 2904 Synonyms: α-Hydroxybenzeneacetic acid; 2-Hydroxy2-phenylacetic acid Source: Cheng, K.-W.; Tang, M.; Chen, Y.-P. Fluid Phase Equil. (2002), 201(1), 79-96.

150

250

P (bar)

477

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478

Solubility in Supercritical Carbon Dioxide

Manganese bis(acetylacetonate) dihydrate (C10H14MnO4·2HO2; FW=289.191)) y3) × 106 0.0337 0.0313 0.0721

1: The mass of dihydrate is included. 2: Obtained by digitizing the graph in the original article. 3: Calculated from S. Synonyms: Bis(2,4-pentanedionato) manganese dihydrate; Mn(acac)2 ·2H2O Source: Saito, N.; Ikushima, Y.; Goto, T. Bull. Chem. Soc. Japan (1990), 63(5), 1532-1534.

0.08 y × 106

2) 2) T (K) P (bar) S (mg/L) 333 98 0.062 196 0.148 294 0.392

0.05

0.02 50

150

250

[M-3]

y x 106

0.2

0.1

0 50

150

Medroxyprogesterone acetate (C24H34O4; MW=386.52) T (K) 308

318

P (bar) 122 152 182 213 243 274 304 355 122 152 182 213 243

y×

350

P (bar)

Manganese tris(acetylacetonate) (C15H21MnO6; FW=352.27) y2) × 106 T (K) P1) (bar) S1) (mg/L) 333 98 0.077 0.034 196 0.493 0.084 294 1.170 0.175 1: Obtained by digitizing the graph in the original article. 2. Calculated from S. Synonyms: Mn(acac)3; Tris(2,4pentanedionato) manganese Source: Saito, N.; Ikushima, Y.; Goto, T. Bull. Chem. Soc. Japan (1990), 63(5), 1532-1534.

[M-2]

106 40 57 74 90 107 128 142 186 30 49 65 89 109

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250

350

P (bar)

[M-4]

Solubility Data M

338

348

274 304 355 122 152 182 213 243 274 304 355 122 152 182 213 243 274 304 355 122 152 182 213 243 274 304 355

150 175 226 23 40 56 86 114 173 208 266 19 36 55 86 124 195 253 339 16 33 54 87 134 219 298 413

500 308 K 318 K 328 K 338 K 348 K

y × 106

328

479

250

0 100

200

300

400

P (bar)

Synonym: 17α -Acetoxy-6α -methylprogesterone Source: Asghari-Khiavi, M.; Yamini, Y.; Farajzadeh, M. A. J. Supercrit. Fluids (2004), 30(2), 111-117.

[M-5]

Medroxyprogesterone acetate (1) + Cyproterone acetate (2) Mixture1) 308

318

P (bar) 122 152 182 213 243 274 304 355 122 152 182 213 243 274 304 355

y1 ×

85 95 105 109 115 139 164 229 64 76 90 105 119 157 193 272

y2 ×

106 51 56 61 65 70 88 105 156 43 47 52 61 69 95 120 180

500

y × 106

T (K)

106

Medroxyprogesterone acetate

250

0 100

308 K 318 K 328 K 338 K 348 K

200

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300 P (bar)

400

480

Solubility in Supercritical Carbon Dioxide

122 43 36 152 58 38 182 75 44 213 100 56 243 124 68 300 274 174 102 Cyproterone acetate 304 222 135 308 K 355 315 205 318 K 338 122 43 30 328 K 200 152 54 34 338 K 182 66 39 348 K 213 95 54 243 130 68 274 200 104 100 304 266 137 355 385 221 348 122 43 25 152 50 29 182 58 33 0 213 90 52 100 200 300 243 136 69 P (bar) 274 226 105 304 310 139 355 454 238 1: Solubility was measured from an equimolar mixture of 1 and 2. Source: Asghari-Khiavi, M.; Yamini, Y.; Farajzadeh, M. A. J. Supercrit. Fluids (2004), 30(2), 111-117.

y × 106

328

[M-6]

Megestrol acetate (C24H32O4; MW=384.51) yx

0.64 1.09 2.32 7.16 13.6 23.4 38.2 49.3 51.7 53.1 1.09 2.84 8.06 13.7 23.3 29.5 43.6

80 328.15 K 373.15 K

60 y x 106

T (K) P (bar) 328.15 82.4 99.0 113.8 129.4 146.1 160.8 177.5 196.1 210.8 226.5 373.15 82.4 99.0 113.8 129.4 146.1 160.8 177.5

106

400

40

20

0 50

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150 P (bar)

250

Solubility Data M

481

196.1 50.7 210.8 55.4 226.5 66.1 Synonym: 17α-Acetoxy-6-dehydro-6-methylprogesterone Source: Dean, J. R.; Kane, M.; Khundker, S.; Dowle, C.; Tranter, R. L.; Jones, P. Analyst (1995), 120(8), 2153-2157.

Menthol (C10H20O; MW=156.27)

[M-7]

6

323 K 343 K

y x 106

y x 10 T (K) P (bar) 60000 323 65 1720 78 2890 88 5331 40000 95 8127 112 42310 120 57830 343 65 720 20000 75 880 82 1020 100 3400 0 115 7290 50 135 22080 Synonym: 5-Methyl-2-(1-methylethyl) cyclohexanol Source: Mukhopadhyay, M.; De, S. K. J. Chem. Eng. Data (1995), 40(4), 909-913.

100

150

P (bar)

[M-8]

Menthol (C10H20O; MW=156.27) y x 106 470 960 1230 1510 4800 12600 1070 1330 4100 5070 7920 13090 480 790 1180 1210 1260 2440 5390 6630 10860

15000 308 K 313 K 318 K 323 K 328 K

10000 y x 106

T (K) P (bar) 308.15 67.0 75.1 77.4 78.0 80.2 81.1 313.15 80.7 82.6 87.7 88.4 89.4 90.7 318.15 71.4 80.3 84.7 86.6 87.4 92.0 96.0 97.2 99.1

5000

0 50

75

CAT4240—CHAPTER 13—31/10/2006—19:15—KADAMBADI—XML MODEL C – pp. 477–512

100 P (bar)

125

482

Solubility in Supercritical Carbon Dioxide

323.15

64.0 220 72.7 470 83.2 770 92.6 1350 95.8 1820 97.5 2290 101.5 3960 103.2 5010 105.4 7490 106.9 9110 328.15 65.2 230 75.6 490 92.2 1130 95.1 1380 103.3 2270 107.4 3780 109.8 5100 113.6 7440 115.6 9130 Synonym: 5-Methyl-2-(1-methylethyl)cyclohexanol Source: Sovova, H.; Jez, J. J. Chem. Eng. Data (1994), 39(4), 840-841.

[M-9]

Menthol (C10H20O; MW=156.27) 106

308.13 K 313.13 K 318.13 K 323.13 K

y x 106

T (K) P (bar) y x 160000 308.13 72.9 2000 77.6 3000 79.2 6000 120000 95.4 11000 128.9 29000 129.9 29000 163.5 31000 80000 163.9 33000 313.13 94.8 18000 129.0 40000 40000 235.6 51000 318.13 96.0 43000 129.0 84000 0 163.0 121000 196.0 147000 50 323.13 94.8 3000 128.9 12000 Synonym: 5-Methyl-2-(1-methylethyl)cyclohexanol Source: Thakur, R., Ph.D. Dissertation, Auburn University, Auburn, Alabama, 2006.

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150 P (bar)

250

Solubility Data M

483

2-Mercaptopyrimidine (C4H4N2S; MW=112.15) 106

50 y x 106

yx T (K) P (bar) 308.15 98.3 38.73 120.0 48.01 144.3 47.08 169.3 46.87 197.7 45.70 Synonyms: 2-Pyrimidinethione; Pyrimidine-2-thiol Source: Nakatani, T.; Tohdo, T.; Ohgaki, K.; Katayama, T. J. Chem. Eng. Data (1991), 36(3), 314-316.

[M-10]

40 30 50

150

250

P (bar)

[M-11]

Mercury dithiocarbamate Complexes M x 106 T (K) P (bar) y1) x 106 (mol/L) Mercury pyrrolidinedithiocarbamate (PDC) (C10H16HgN2S4; FW=493.08) 333.15

101 0.35 0.05 233 3.40 0.19 Mercury bis(diethyldithiocarbamate) (DDC) (C10H20HgN2S4; FW=497.11)

900

101 6.8 1.00 233 53.0 3.03 Mercury bis(dipropyldithiocarbamate) (P3DC) (C14H28HgN2S4; FW=553.22)

PDC DDC P3DC BDC P5DC HDC FDDC

333.15

101 12 1.77 233 230 13.10 Mercury bis(dibutyldithiocarbamate) (BDC) (C18H36HgN2S4; FW=609.33) 333.15

101 56 8.25 233 560 32.00 Mercury bis(dipentyldithiocarbamate) (P5DC) (C22H44HgN2S4; FW=665.43)

y x 106

333.15

600

300

333.15

101 100 14.70 233 2000 114.00 Mercury bis(dihexyldithiocarbamate) (HDC) (C26H52HgN2S4; FW=721.54)

0 0

100

333.15

101 160 23.60 233 3800 217.00 Mercury bis[bis(trifluoroethyl)dithiocarbamate] (FDDC) (C10H8F12HgN2S4; FW=713.00) 333.15

101 3000 442.00 233 14000 799.00 1: Calculated from M. Source: Wai, C. M.; Wang, S.; Yu, J.-J. Anal. Chem. (1996), 68(19), 3516-3519.

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200 P (bar)

300

484

Solubility in Supercritical Carbon Dioxide

Metal diethyldithiocarbamate Complexes Compounds

[M-12] Formula

T (K)

P (bar)

C5H4F6NNaS2 323.15 101.3 C5H10NNaS2 323.15 101.3 Sodium diethyldithiocarbamate C H Copper bis[bis(trifluoroethyl)dithiocarbamate] 8 10CuF12N2S4 323.15 101.3 C10H20CuN2S4 323.15 101.3 Copper bis(diethyldithiocarbamate) Sodium bis(trifluoroethyl)dithiocarbamate

106

Mx y1) x 106 (mol/L) 470.0

50.87

150.0

16.24

910.0

98.48

1.1

0.12

C10H8F12N2NiS4 323.15 101.3 C10H20N2NiS4 323.15 101.3

720.0

77.92

0.9

0.09

Cobalt tris[bis(trifluoroethyl)dithiocarbamate] C15H12CoF18N3S6 323.15 101.3 C15H30CoN3S6 323.15 101.3 Cobalt tris(diethyldithiocarbamate)

800.0

86.58

2.4

0.26

Bismuth tris[bis(trifluoroethyl)dithiocarbamate] C15H12BiF18N3S6 323.15 101.3 152.0 C15H30BiN3S6 323.15 101.3 Bismuth tris(diethyldithiocarbamate)

0.1 730.0

0.01 45.43

1.3 9.0

0.14 0.56

Nickel bis[bis(trifluoroethyl)dithiocarbamate] Nickel bis(diethyldithiocarbamate)

152.0

1: Calculated from M. Source: Laintz, K. E.; Wai, C. M.; Yonker, C. R.; Smith, R. D. J. Supercrit. Fluids(1991), 4(3), 194-198.

Metal b -diketone and Metal dithiocarbamate Complexes

[M-13] 104

P (bar)

Mx (mol/L)

333.15

101.3

0.09

Bismuth tris[bis(trifluoroethyl)dithiocarbamate] C15H12F18BiN3S6 333.15

Compounds Bismuth tris(diethyldithiocarbamate)

Formula T (K) C15H30BiN3S6

y1) x 106 1.330

101.3

7.30

108

C15H30CoN3S6

333.15

101.3

0.024

0.354

Cobalt tris[bis(trifluoroethyl)dithiocarbamate] C15H12F18CoN3S6

333.15

101.3

8.0

118

C15H21CrO6

333.15

202.7

121 173 > 4840 > 4040 0.162

Cobalt tris(diethyldithiocarbamate)

Chromium tris(hexafluoroacetylacetonate)

C15H3CrF18O6

333.15

405.3 202.7

Copper bis(diethyldithiocarbamate)

C10H20CoN2S4

333.15

405.3 101.3

20.0 35.0 >800 >820 0.011

Copper bis[bis(trifluoroethyl)dithiocarbamate] C10H8F12CoN2S4

333.15

101.3

9.1

134

C10H2CoF12O4

333.15

202.7

333.15

405.3 152.0

870 850 0.082

5260 4190 0.590

Mercury bis[bis(trifluoroethyl)dithiocarbamate] C10H8F12HgN2S4 333.15

152.0

50.0

53.1

1.5

22.1

Chromium tris(acetylacetonate)

Copper bis(hexafluoroacetylacetonate) Mercury bis(diethyldithiocarbamate)

C10H20HgN2S4 C5H10NNaS2

333.15

101.3

Sodium bis(trifluoroethyl)dithiocarbamate

C5H4F6NNaS2

333.15

101.3

4.7

69.4

Nickel bis(diethyldithiocarbamate)

C10H20N2NiS4

333.15

101.3

0.0085

0.125

C10H8F12N2NiS4

333.15

101.3

7.2

106

C10H2F12NiO4

333.15

202.7

80.0

484

405.3

99.0

488

Sodium diethyldithiocarbamate

Nickel bis[bis(trifluoroethyl)dithiocarbamate] Nickel bis(hexafluoroacetylacetonate)

1: Calculated from M. Source: Ashraf-Khorassani, M.; Combs, M. T.; Taylor, L. T. Talanta(1997), 44(5), 755-763.

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Solubility Data M

485

Metal dithiocarbamate Complexes

[M-14] FW

Name of Complexes (Formula) Rhodium tris(diethyldithiocarbamate) (C15H30N3RhS6)

T (K)

P Mx y1) x 106 (bar) (mol/L) 105

547.69 353.15 300

4.61

2.71

Rhodium tris(diisopropyldithiocarbamate) (C21H42N3RhS6) 631.85 353.15 300

5.00

2.94

Rhodium tris(dibutyldithiocarbamate) (C27H54N3RhS6)

716.01 353.15 300

15.30

9.01

Rhodium tris(diisobutyldithiocarbamate) (C27H54N3RhS6)

716.01 353.15 300 201.00

118.30

Rhodium tris(dihexyldithiocarbamate) (C39H78N3RhS6)

884.33 353.15 300

88.70

52.20

Rhodium tris(dioctyldithiocarbamate) (C51H102N3RhS6)

1052.7 353.15 300

55.80

32.90

Palladium bis(diethyldithiocarbamate) (C10H20N2PdS4)

402.92 353.15 300

0.47

0.277

Palladium bis(diisopropyldithiocarbamate) (C14H28N2PdS4) 459.03 353.15 300

1.20

0.707

515.14 353.15 300

15.00

8.830

Palladium bis(diisobutyldithiocarbamate) (C18H36N2PdS4) 515.14 353.15 300

41.00

24.100

Palladium bis(dibutyldithiocarbamate) (C18H36N2PdS4) Palladium bis(dipentyldithiocarbamate) (C22H44N2PdS4)

571.24 353.15 300

7.00

4.120

Palladium bis(dioctyldithiocarbamate) (C34H68N2PdS4)

739.57 353.15 300

1.60

0.942

1: Calculated from M. Source: Wenclawiak, B. W.; Wolf, A.; Wilnewski, S. in: Supercritical Fluids as Solvents and Reaction Media, Brunner, G. (ed.), Elsevier B.V., Amsterdam, Netherlands (2004), 323-340. (Numerical data obtained from the authors.)

Metal trifluoroethyldithiocarbamates Compounds

[M-15] Formula

T (K)

4 P (bar) M x 10 y1) x 106 (mol/L)

Arsenic tris[bis(trifluoroethyl)dithiocarbamate] C15H12AsF18N3S6 323.15 101.325

53.0

573

Mercury bis[bis(trifluoroethyl)dithiocarbamate] C10H8F12HgN2S4 323.15 101.325

4.2

45

Cobalt tris[bis(trifluoroethyl)dithiocarbamate] C15H12F18CoN3S6 323.15 101.325

8.0

87

Copper bis[bis(trifluoroethyl)dithiocarbamate] C10H8F12CoN2S4 323.15 101.325 C10H8F12N2NiS4 323.15 101.325 Nickel bis[bis(trifluoroethyl)dithiocarbamate]

8.2

89

7.2

78

1: Calculated from M. Source: Wai, C. M.; Brauer, R. D.; Liu, Y.; Lopez-Avila, V.; Beckert, W. F. Proceedings of ACS Meeting (1993), 33(1), 363-366.

Methimazole (C4H6N2S; MW=114.17) T (K) 308

P (bar) 122 152 182 213 243 274 304 355

S (g/L) 0.04 0.05 0.06 0.09 0.10 0.12 0.13 0.14

y x 106 22.3 23.1 29.5 40.3 44.9 50.4 52.9 59.9

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[M-16]

486

Solubility in Supercritical Carbon Dioxide

318

308 K 318 K 328 K 338 K 348 K

y x 106

122 0.04 21.3 152 0.04 20.6 182 0.07 32.2 213 0.09 40.2 243 0.12 55.0 274 0.14 63.3 200 304 0.16 69.5 355 0.20 82.5 328 122 0.02 18.9 152 0.03 19.7 150 182 0.07 35.4 213 0.10 50.7 243 0.13 63.7 274 0.16 73.9 100 304 0.20 91.6 355 0.27 118.4 338 122 0.01 15.1 50 152 0.03 17.3 182 0.09 34.7 213 0.10 51.9 243 0.15 76.7 0 274 0.18 89.3 100 304 0.24 116.0 355 0.33 148.6 348 152 0.02 12.2 182 0.04 30.0 213 0.09 52.5 243 0.16 85.4 274 0.22 112.1 304 0.28 137.8 355 0.40 189.9 Synonyms: 1-Methylimidazole-2-thiol; 1-Methyl-4imidazoline-2-thione Source: Asghari-Khiavi, M.; Yamini, Y. J. Chem. Eng. Data (2003), 48(1), 61-65. (The same data were reported in: Yamini, Y.; Arab, J.; AsghariKhiavi, M. Pharm. Bio. Anal. (2003), 32(1), 181-187).

200

300 P (bar)

3-Methoxybenzamide (C8H9O2N; MW=151.16)

[M-17]

4000 343 K 363 K

y x 106

T (K) P (bar) y x 106 90 343 560 100 902 120 2021 90 363 1210 100 1800 120 3450 Synonym: m-Anisamide Source: Bristow, S.; Shekunov, B. Y.; York, P. Ind. Eng. Chem. Res. (2001), 40(7), 1732-1739.

400

2000

0 80

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100 P (bar)

120

Solubility Data M

487

4-Methoxybenzamide (C8H9O2N; MW=151.16) 1200 y x 106

T (K) P (bar) y1) x 106 200 90 343 323 100 673 120 1028 140 399 90 363 100 630 Synonym: p -Anisamide Source: Bristow, S.; Shekunov, B. Y.; York, P. Ind. Eng. Chem. Res. (2001), 40(7), 1732-1739.

[M-18]

800 400

343 K 363 K

0 80

100

120 P (bar)

2-Methoxybenzoic acid (C8H8O3; MW=152.15)

[M-19]

120000 308.2 K 318.2 K 328.2 K

80000 y x 106

y x 106 T (K) P (bar) 308.2 99.8 24000 120.3 32700 142.1 40800 163.6 48400 184.3 53800 204.3 59500 225.0 65000 246.9 69600 318.2 99.8 8940 121.5 30600 141.9 44100 162.8 54100 183.7 63900 205.0 74900 224.9 80900 246.3 89200 328.2 120.4 15500 141.5 39200 163.1 59000 183.7 75100 204.6 92200 225.6 105000 246.9 111000 Synonym: o -Anisic acid Source: Chen, J. W.; Tsai, F. N. Fluid Phase Equil. (1995), 107(2), 189-200.

140

40000

0 50

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150 P (bar)

250

488

Solubility in Supercritical Carbon Dioxide

3-Methoxybenzoic acid (C8H8O3; MW=152.15) T (K)

P (bar)

yx

[M-20]

106

308.2

180000

y x 106

99.6 22700 120.7 38700 141.8 48800 162.8 57100 183.9 67300 204.8 72200 225.0 79600 245.7 85200 318.2 120.5 31700 141.9 51500 162.3 70500 183.5 88400 204.8 104000 225.4 118000 245.9 126000 328.2 120.5 16500 141.0 45300 163.7 80000 183.4 107000 204.9 133000 225.7 157000 245.9 173000 Synonym: m -Anisic acid Source: Chen, J. W.; Tsai, F. N. Fluid Phase Equil. (1995), 107(2), 189-200.

308.2 K 318.2 K 328.2 K

120000

60000

0 50

150 P (bar)

4-Methoxybenzoic acid (C8H8O3; MW=152.15)

[M-21]

100000 308.2 K 318.2 K 328.2 K

y x 106

T (K) P (bar) y x 106 308.2 141.6 29200 162.0 33600 183.7 37700 204.1 40500 225.0 44100 245.4 46200 318.2 140.8 30900 163.3 38300 183.7 44900 204.5 51500 225.1 57900 245.9 63300 328.2 142.0 28100 162.3 41500 182.8 55900 203.5 68600 224.5 79400 246.0 90600 Synonym: p -Anisic acid Source: Chen, J. W.; Tsai, F. N. Fluid Phase Equil. (1995), 107(2), 189-200.

250

60000

20000 100

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200 P (bar)

300

Solubility Data M

489

Methoxychlor (C16H15Cl3O2; MW=345.65)

[M-22]

106

1500

y x 106

yx T (K) P (bar) 313.1 100 164 130 392 160 603 190 737 220 958 333.1 100 7 130 141 160 487 190 925 220 1420 Synonyms: DMDT; 1,1,1-Trichloro-2,2bis(4-methoxyphenyl)ethane Source: Macnaughton, S. J.; Kikic, I.; Rovedo, G.; Foster, N. R.; Alessi, P. J. Chem. Eng. Data(1995), 40(3), 593-597.

313.1 K 333.1 K

1000 500 0 50

150

250

P (bar)

7-Methoxycoumarin (C10H8O3; MW=176.17)

[M-23]

106

308.15 K 313.15 K 323.15 K

y x 106

yx T (K) P (bar) 308.15 85 16.5 450 100 88.0 150 129.0 200 295.0 250 410.0 300 313.15 85 5.1 100 55.7 150 163.0 200 309.0 150 250 400.0 323.15 85 0.5 100 45.7 150 209.0 0 200 393.0 0 250 455.0 Synonyms: 7-Methoxy-2H-1-benzopyran2-one; Methylumbelliferone Source: Yoo, K.-P.; Shin, H. Y.; Noh, M. J.; You, S. S. Korean J. Chem. Eng. (1997), 14(5), 341-346.

100

200 P (bar)

5-Methoxyindole (C9H9NO; MW=147.17)

[M-24] 2000 y x 106

T (K) P (bar) y x 106 308.15 79.8 191 96.5 861 109.0 1200 137.0 1500 159.0 1550 184.0 1750 Synonym: 5-Methoxy-1H-indole Source: Sako, S.; Shibata, K.; Ohgaki, K.; Katayama, T. J. Supercrit. Fluids (1989), 2(1), 3-8.

300

1000

0 50

100

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150 P (bar)

200

490

Solubility in Supercritical Carbon Dioxide

2-Methoxynapthalene (C11H10O; MW=158.20) 10000 y x 106

T (K) P1) (bar) y1) x 106 308.15 113 3090 120 3830 154 6070 178 7410 194 8260 1: Obtained by digitizing the graph in the original article. Synonym: Methyl-2-naphthyl ether Source: Nakatani, T.; Ohgaki, K.; Katayama, T. Ind. Eng. Chem. Res. (1991), 30(6), 1362-1366.

[M-25]

5000

0 100

150

200

P (bar)

2-Methoxyphenol (C7H8O2; MW=124.14)

[M-26]

323.15 K 353.15 K 393.15 K

y x 106

T (K) P (bar) y x 106 323.15 20 125 30 115 40 159 50 205 60 311 120000 80 838 100 5330 130 41000 150 61500 180 111000 80000 353.15 20 799 30 718 40 676 50 735 60 762 40000 80 1120 100 2090 130 5950 160 18400 200 56500 0 393.15 20 4550 30 3850 0 40 3380 50 3300 60 3470 80 3810 100 4760 130 6890 160 11600 200 23100 Synonym: 2-Hydroxyanisole Source: Lee, M.-J.; Kou, C.-F.; Cheng, J.-W.; Lin, H.-M. Fluid Phase Equil. (1999), 162(1-2), 211-224.

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100 P (bar)

200

Solubility Data M

491

[M-27]

o -, m - & p - Methoxyphenylacetic acid (C9H10O3; MW=166.17) T (K)

P (bar)

y x 106

o-MPAA m-MPAA p-MPAA

y x 106

o-MPAA1) 4500 76 308.2 122 142 181 258 240 333 300 3000 367 337 1) m-MPAA 308.2 117 730 180 1680 239 2600 1500 300 3720 339 3980 p-MPAA1) 308.2 121 190 0 180 400 100 240 810 303 1180 339 1440 1: MPAA = Methoxyphenylacetic acid. Source: Lee, H. K.; Kim, C. H.; Kim, S.; Choi, C. S. J. Chem. Eng. Data (1994), 39(1), 163-165.

200

300

P (bar)

5-Methoxy-1-tetralone (C11H12O2; MW=176.21) 308

P (bar)

y x 106

83.0 110.0 138.0 172.0 207.0 275.0

2200 4200 4400 4900 5400 6000

8000 y x 106

T (K)

[M-28]

4000

0

Synonym: 3,4-Dihydro-5-methoxy-1(2H)naphthalenone Source: Chang, H.; Morrell, D. G. J. Chem. Eng. Data (1985), 30(1), 74-78.

0

100

200 P (bar)

6-Methoxy-1-tetralone (C11H12O2; MW=176.21) yx

1300 3500 5200 6800 10000 12000

Synonym: 3,4-Dihydro-6-methoxy-1(2H)naphthalenone Source: Chang, H.; Morrell, D. G. J. Chem. Eng. Data (1985), 30(1), 74-78.

[M-29]

14000 y x 106

T (K) P (bar) 83.0 308 111.0 138.0 179.0 219.0 277.0

106

300

7000

0 0

100

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P (bar)

200

300

492

Solubility in Supercritical Carbon Dioxide

7-Methoxy-1-tetralone (C11H12O2; MW=176.21) y x 10

[M-30] 80000

7400 17200 24100 36900 58500 75300

y x 106

T (K) P (bar) 85.0 308 111.0 138.0 179.0 219.0 276.0

6

40000

0

Synonym: 3,4-Dihydro-7-methoxy-1(2H)naphthalenone Source: Chang, H.; Morrell, D. G. J. Chem. Eng. Data (1985), 30(1), 74-78.

0

100

200 P (bar)

6-Methoxy-1-tetralone (1) + 7-Methoxy-1-tetralone (2) Mixture

308

P (bar) 110

x1 (mol%) 0 10 30 50 65 70 70 80 90 100

y1 x

0 800 2400 4200 5000 4700 5100 4600 4800 3500

y2 x

106

17200 12400 9000 6000 3600 2800 3100 3000 2400 0

[M-31]

20000 1 2

y x 106

T (K)

106

10000

0 0

Source: Chang, H.; Morrell, D. G. J. Chem. Eng. Data (1985), 30(1), 74-78.

50

110

x1 y1 x 106 y2 x 106 (mol%) 0 0 4200 30 4600 6100 70 9000 2800 100 17200 0

Source: Chang, H.; Morrell, D. G. J. Chem. Eng. Data (1985), 30(1), 74-78.

[M-32]

20000 y x 106

308

P(bar)

100

x1 (mol%)

7-Methoxy-1-tetralone (1) + 5-Methoxy-1-tetralone (2) Mixture T(K)

300

1 2

10000

0 0

50 x1 (mol%)

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100

Solubility Data M

493

2-Methylanthracene (C15H12; MW=192.26) yx

97 116 146 168 185 201 217 233 240 74 120 161 192 227 255 279 304 316 60 109 163 218 270 312 354 385 410 42 89 157 235 298 363 429 481 515 24 65

182

134

213

229

243

317

274

414

304

500

334

584

355

641

600

y x 106

T (K) P (bar) 308 122 152 182 213 243 274 304 334 355 318 122 152 182 213 243 274 304 334 355 328 122 152 182 213 243 274 304 334 355 338 122 152 182 213 243 274 304 334 355 348 122 152

[M-33]

106

308 K 318 K 328 K 338 K 348 K

400

200

0 100

200

Source: Yamini, Y.; Bahramifar, N.; Hassan, J. J. Chem. Eng. Data (2002), 47(2), 329-332.

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300 P (bar)

400

494

Solubility in Supercritical Carbon Dioxide

2-Methylbenzoic acid (C8H8O2; MW=136.16) T (K)

P (bar)

[M-34]

y x 106

6000 110 902 137 1380 164 1820 192 2130 219 2380 4000 246 2540 323.2 110 510 137 1510 164 2230 2000 192 2880 219 3420 246 3820 333.2 110 240 137 1280 0 164 2570 100 192 3750 219 4810 246 5700 Source: Tsai, K.-L.; Tsai, F.-N. J. Chem. Eng. Data (1995), 40(1), 264-266.

313.2 K 323.2 K 333.2 K

y x 106

313.2

150

200 P (bar)

3-Methylbenzoic acid (C8H8O2; MW=136.16)

[M-35]

313.2 K 323.2 K 333.2 K

y x 106

y x 106 T (K) P (bar) 313.2 110 910 6000 137 1460 164 1880 192 2210 219 2400 4000 246 2650 323.2 110 470 137 1370 164 2140 2000 192 2860 219 3390 246 3870 333.2 110 184 137 1160 0 164 2290 100 192 3390 219 4650 246 5340 Source: Tsai, K.-L.; Tsai, F.-N. J. Chem. Eng. Data (1995), 40(1), 264-266.

250

150

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200 P (bar)

250

Solubility Data M

495

4-Methylbenzoic acid (C8H8O2; MW=136.16) T (K)

P (bar)

yx

[M-36]

106

110 148 137 212 164 267 192 306 219 344 246 371 323.2 110 80 137 209 164 316 192 397 219 462 246 513 333.2 110 43 137 181 164 347 192 487 219 600 246 702 Source: Tsai, K.-L.; Tsai, F.-N. J. Chem. Eng. Data (1995), 40(1), 264-266.

y x 106

313.2

800 600

313.2 K 323.2 K 333.2 K

400 200 0 100

150

200

250

P (bar)

6-Methylcoumarin (C10H8O2 ; MW=160.17)

[M-37]

106

308.15 K 313.15 K 323.15 K

y x 106

yx T (K) P (bar) 20000 308.15 85 1170 100 3100 150 7810 15000 200 11700 250 10700 313.15 85 745 10000 100 2600 150 6300 200 8110 5000 250 10700 323.15 85 600 0 100 1290 150 8340 50 200 15400 250 5060 1: Could not get the verification of the data from the authors. Synonym: 6-Methyl-2H-1-benzopyran-2-one Source: Yoo, K.-P.; Shin, H. Y.; Noh, M. J.; You, S. S. Korean J. Chem. Eng. (1997), 14(5), 341-346.

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150 P (bar)

250

496

Solubility in Supercritical Carbon Dioxide

7-Methylcoumarin (C10H8O2; MW=160.17) yx

368 691 1131 1217 1396 103 656 1317 1606 1793 33 163 2165 1719 2165

2000 y x 106

T (K) P (bar) 308.15 85 100 150 200 250 313.15 85 100 150 200 250 323.15 85 100 150 200 250

[M-38]

106

1000 308.15 K 313.15 K 323.15 K

0 50

150

250

P (bar)

Synonym: 7-Methyl-2H-1-benzopyran-2-one Source: Yoo, K.-P.; Shin, H. Y.; Noh, M. J.; You, S. S. Korean J. Chem. Eng. (1997), 14(5), 341-346.

Methyl gallate (C8H8O5; MW=184.15)

[M-39]

106

P(bar) y x 100 0.120 150 0.356 200 0.557 250 0.765 4.5 300 1.023 350 1.243 400 1.499 450 1.902 500 2.213 3.0 323 100 0.003 150 0.012 200 0.027 300 0.034 350 0.065 1.5 400 0.022 450 0.060 500 0.060 333 100 0.019 0.0 150 0.557 200 1.044 0 250 1.917 300 2.409 350 2.997 400 3.520 450 3.982 500 4.240 Synonyms: 3,4,5-Trihydroxybenzoic acid methyl ester; Gallic acid methyl ester Source: Murga, R.; Sanz, M. T.; Beltran, S.; Cabezas, J. L. J. Supercrit. Fluids (2002), 23(2), 113-121.

313 K 323 K 333 K

y x 106

T (K) 313

200

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400 P (bar)

600

Solubility Data M

497

1-Methylnaphthalene (C11H10; MW=142.20) P(bar) 79.1 97.1 121.5 157.1 200.2 245.3 277.4 104.0 124.3 153.7 195.0 241.7 278.1

328.15

yx

60000

7800 15900 21300 29000 37400 44700 50000 2400 9400 19200 30600 44900 58800

308.15 K 328.15 K

y x 106

T (K) 308.15

[M-40]

106

40000

20000

0 50

150

250

P (bar)

Source: Chung, S. T.; Shing, K. S. Fluid Phase Equil. (1992), 81, 321-341.

2-Methylnaphthalene (C11H10; MW=142.20) T (K)

P(bar)

[M-41]

6

y x 10 77.5 8400 96.1 17800 111.7 21000 131.9 24100 172.7 41800 209.2 44700 251.5 52800 278.8 64200 328.15 101.0 2300 117.7 7200 148.8 22100 188.9 37000 245.7 64900 271.5 79100 Source: Chung, S. T.; Shing, K. S. Fluid Phase Equil. (1992), 81, 321-341.

90000

308.15

y x 106

308.15 K 328.15 K

60000

30000

0 50

150

250

P (bar)

1-Methylnaphthalene (1) & 2-Methylnaphthalene (2) Mixture P (bar)

y1 x 106

y2x 106

xov1)= 0.44 308.15 78.0 4000 4500 99.5 8100 9300 122.4 10700 12500 162.5 12100 16100 203.3 17200 19900 246.3 24400 26600 1: Initial (overall) composition of naphthalene in the mixture of solutes 1 and 2 (mole fraction). Source: Chung, S. T.; Shing, K. S. Fluid Phase Equil. (1992), 81, 321-341.

30000

y x 106

T (K)

[M-42]

1-MeNaph 2-MeNaph

20000 10000 0 0

100

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200 P (bar)

300

498

Solubility in Supercritical Carbon Dioxide

Methyl o-nitrobenzoate (C8H7NO4; MW=181.15) y x 106

60000

5700 14600 21200 34600 51200

y x 106

T (K) P (bar) 308 83.0 111.0 138.0 220.0 278.0

[M-43]

30000

Synonyms: 2-Nitrobenzoic acid methyl ester; Methyl 2-nitrobenzoate Source: Chang, H.; Morrell, D. G. J. Chem. Eng. Data (1985), 30(1), 74-78.

0 0

100

200 P (bar)

Methyl m-nitrobenzoate (C8H7NO4; MW=181.15) y x 106 T (K) P (bar) 308 83.0 2700 111.0 6300 200.0 16000 277.0 19100 Synonyms: 3-Nitrobenzoic acid methyl ester; Methyl 3-nitrobenzoate Source: Chang, H.; Morrell, D. G. J. Chem. Eng. Data (1985), 30(1), 74-78.

[M-44]

y x 106

20000 10000 0 0

100

200

83 110 138 172 207 272

y x 106

[M-45]

16000

1200 4800 7000 9400 11100 14900

y x 106

308

P (bar)

8000 0

Synonyms: 4-Nitrobenzoic acid methyl ester; Methyl 4-nitrobenzoate Source: Chang, H.; Morrell, D. G. J. Chem. Eng. Data (1985), 30(1), 74-78.

0

100

200

308

P (bar) 110

(mol%) 0 30 70 100

y1 x

0 4200 10800 14600

y2 x

106

6300 10200 5100 0

1: Initial composition of Methyl o-nitrobenzoate in the mixture of solutes 1 and 2 (CO2-free). Source: Chang, H.; Morrell, D. G. J. Chem. Eng. Data (1985), 30(1), 74-78.

[M-46]

20000

y x 106

T (K)

106

300

P (bar)

Methyl o-nitrobenzoate (1) + Methyl m-nitrobenzoate (2) Mixture x11)

300

P (bar)

Methyl p-nitrobenzoate (C8H7NO4; MW=181.15) T (K)

300

1 2

10000

0 0

50 x1 (mol%)

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100

Solubility Data M

499

Methyl o-nitrobenzoate (1) + Methyl p-nitrobenzoate (2) Mixture P (bar)

y2 x 106 x11) y1 x 106 (mol%) 0 308 110 0 4800 30 7200 14300 70 11000 6900 100 14600 0 1: Initial composition of Methyl o-nitrobenzoate in the mixture of solutes 1 and 2 (CO2-free). Source: Chang, H.; Morrell, D. G. J. Chem. Eng. Data (1985), 30(1), 74-78.

[M-47]

20000 y x 106

T (K)

1 2

10000

0

0

50 x1 (mol%)

Methyl oleate (C21H36O2; MW=296.49) T (K)

P (bar)

100

[M-48]

y x 106

313.15

313.15 K 323.15 K 333.15 K

y x 106

95.5 3000 40000 102.9 5000 107.5 7000 121.5 24000 122.0 27000 30000 123.4 30000 126.1 33000 323.15 121.5 3000 20000 129.9 5000 135.2 7000 149.6 24000 151.0 27000 10000 151.0 30000 154.8 33000 333.15 146.7 3000 0 153.6 5000 50 160.4 7000 177.0 27000 180.7 28000 33000 181.2 Synonyms: (Z)-9-Octadecenoic acid methyl ester; Oleic acid methyl ester Source: Crampon, C.; Charbit, G.; Neau, E. J. Supercrit. Fluids (1999), 16(1), 11-20.

100

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150 P (bar)

200

500

Solubility in Supercritical Carbon Dioxide

Methyl oleate (C19H36O2; MW=296.49) T (K)

P (bar)

yx

[M-49]

106

313.15

313.15 K 333.15 K 353.15 K

y x 106

62.0 0 66.9 170 30000 80.9 1270 96.0 2860 100.0 4590 108.0 6730 120.0 11980 20000 125.0 13750 333.15 52.1 0 69.0 0 95.5 430 125.0 1900 10000 138.0 4570 164.0 12540 183.0 24570 353.15 51.2 0 66.5 0 0 97.0 420 50 121.0 970 150.3 1680 179.5 9210 209.7 13240 223.2 24640 Synonyms: (Z )-9-Octadecenoic acid methyl ester; Oleic acid methyl ester Source: Fang, T.; Goto, M.; Yun, Z.; Ding, X.-l.; Hirose, T. J. Supercrit. Fluids (2004), 30(1), 1-16.

150 P (bar)

Methyl oleate (C19H36O2; MW=296.49)

333.15

P (bar) 110 124 131 110 124 131 137 151

w x 10

7700 29100 40000 1600 6100 11000 17700 36300

1)

y x 10

[M-50]

6

1150 4430 6150 238 910 1650 2670 5560

1: Calculated from w. Synonyms: (Z )-9-Octadecenoic acid methyl ester; Oleic acid methyl ester Source: Nilsson, W. B.; Gauglitz, E. J. Jr.; Hudson, J. K. J. Am. Oil Chem. Soc. (1991), 68(2), 87-91.

7000

y x 106

T (K) 323.15

6

250

323.15 K 333.15 K

3500

0 100

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125 P (bar)

150

Solubility Data M

501

3-Methyl-3-pentanol (C6H14O; MW=102.17)

323.4 K 362.8 K 381.6 K

y x 106

S (g/L) y1) x 106 T (K) P (bar) 323.4 80 3.3 6410 83 4.8 8630 85 5.2 8870 86 6.0 9960 87 6.9 11100 88 7.2 11300 89 8.2 12500 150000 90 8.7 12900 91 9.6 13800 92 10.0 14000 94 12.0 15800 95 17.2 21900 96 24.1 29500 100000 362.8 114 19.3 32500 118 25.5 40400 120 24.5 37900 123 28.4 42200 126 35.1 49800 50000 130 42.8 57500 133 59.6 75800 136 70.3 85400 381.6 100 14.8 34200 105 16.2 35200 0 110 19.3 39200 75 115 21.3 40800 120 25.4 45700 124 27.8 47800 127 30.7 50900 130 36.6 58300 134 42.1 64000 138 51.6 74500 141 56.0 78300 144 70.4 94000 147 81.4 104000 150 102.2 125000 1: Calculated from S. Synonym: Diethyl methyl carbinol Source: Friedrich, J.; Schneider, G. M. J. Chem. Thermodyn. (1989), 21(3), 307-319.

[M-51]

100

Methyl salicylate (C8H8O3 ; MW=152.15) T (K)

P (bar)

308.15

15.2 29.5 42.4 55.9 69.8 83.8

y x 106 200 200 300 300 400 1000

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125

150

P (bar)

[M-52]

502

Solubility in Supercritical Carbon Dioxide

318.15

308.15 K 318.15 K 328.15 K

y x 106

15.7 400 15000 29.1 400 43.2 400 56.0 500 68.6 500 82.7 600 10000 99.6 3700 112.4 7900 328.15 15.5 300 28.6 300 42.4 400 5000 56.3 400 69.6 600 93.4 1000 100.6 1300 0 121.0 5100 0 132.0 13200 Synonyms: 2-Hydroxybenzoic acid methyl ester; Methyl 2-hydroxybenzoate Source: Cheng, K.-W.; Kuo, S.-J.; Tang, M.; Chen, Y.- P. J. Supercrit. Fluids (2000), 18(2), 87-99.

50

100 P (bar)

Methylparaben (C8H8O3; MW=152.15) 308

318

328

P (bar) 122 152 182 213 243 274 304 355 122 152 182 213 243 274 304 355 122 152 182 213 243 274 304 355

S (g/L) 0.30 0.38 0.47 0.57 0.60 0.66 0.75 0.84 0.26 0.40 0.55 0.70 0.77 0.91 1.07 1.26 0.19 0.39 0.60 0.80 0.98 1.13 1.25 1.51

[M-53]

y x 106 113 135 160 188 194 209 233 256 113 157 200 248 262 301 345 396 108 170 237 300 351 395 422 493

1500

1000

308 K 318 K 328 K 338 K 348 K

y x 106

T (K)

150

500

0 100

200

CAT4240—CHAPTER 13—31/10/2006—19:16—KADAMBADI—XML MODEL C – pp. 477–512

P (bar)

300

400

Solubility Data M

338

348

122 152 182 213 243 274 304 355 122 152 182 213 243 274 304 355

503

0.16 0.34 0.67 1.04 1.18 1.48 1.80 2.11 0.15 0.31 0.70 1.13 1.51 2.07 2.56 3.40

118 173 295 422 451 547 641 719 135 185 345 503 602 808 960 1213

Synonyms: 4-(Carbomethoxy)phenol; Methyl 4-hydroxybenzoate Source: Asghari-Khiavi, M.; Yamini, Y. J. Chem. Eng. Data (2003), 48(1), 61-65.

Metronidazole benzoate (C13H13N3O4; MW=275.26)

318

328

338

P (bar) 122 152 182 213 243 274 304 355 122 152 182 213 243 274 304 355 122 152 182 213 243 274 304 355 122 152 182

S (g/L) 2.38 2.76 3.23 3.86 4.73 5.44 6.31 8.34 1.11 1.75 2.57 3.59 4.70 2.91 7.09 8.44 0.48 1.45 2.53 3.97 5.28 6.49 7.68 9.80 0.16 0.83 2.10

y x 106 490 540 610 700 840 950 1080 1390 270 370 720 690 880 1080 1270 1470 120 350 560 820 1050 1250 1440 1770 70 240 510

5000

4000

y x 106

T (K) 308

[M-54]

308 K 318 K 328 K 338 K 348 K

3000

2000

1000

0 100

200

CAT4240—CHAPTER 13—31/10/2006—19:16—KADAMBADI—XML MODEL C – pp. 477–512

300 P (bar)

400

504

Solubility in Supercritical Carbon Dioxide

213 3.86 870 243 5.93 1260 274 8.00 1620 304 11.57 2270 355 14.87 2790 348 122 0.32 160 152 1.40 407 182 2.03 550 213 4.83 1180 243 7.68 1750 274 10.62 2290 304 14.63 3020 355 23.17 4550 Synonym: 2-Methyl-5-nitro-1H-imidazole-1-ethanol benzoate Source: Garmroodi, A.; Hassan, J.; Yamini, Y. J. Chem. Eng. Data (2004), 49(3), 709-712.

Miconazole (C18H14ClO4N2; MW=416.12) T (K) 313

P1)

(bar)

w1)

x

106

y2)

x

[M-55]

106

y x 106

84.4 80 8.5 200 99.4 400 42.3 115.8 760 80.4 139.7 1280 136.0 100 179.5 2130 226.0 1: Obtained by digitizing the graph in the original article. 0 2: Calculated from w. 50 Synonym: 1-[2-(2,4-Dichlorophenyl)-2[(2,4-dichlorophenyl)methoxy]ethyl]-1Himidazole Source: Smirnova, I.; Mamic, J.; Arlt, W. Langmuir (2003), 19(20), 8521-8525.

100

150

Milk fat triglyceride1)

[M-56] 106

T (K) P (bar) 323.15 120 400 160 3890 220 11960 330 20470 353.15 195 600 1: Commercial butter oil after removal of protein residues. 2: Weight fraction solubility on a solutefree basis. Source: Arul, J.; Tardif, R.; Boudreau, A.; McGinnis, D. S.; Lencki, R. W. Food Res. Internat. (1994), 27(5), 459-467.

24000 w x 106

w2)x

200

P (bar)

323.15 K 353.15 K

12000 0 100

CAT4240—CHAPTER 13—31/10/2006—19:16—KADAMBADI—XML MODEL C – pp. 477–512

200 P (bar)

300

Solubility Data M

505

Milk thistle seed oil1)

[M-57]

w x 106

P (bar) 101.0 1300 20000 151.5 5400 185.0 7700 250.5 9800 15000 296.0 12600 333 103.5 6000 157.0 6700 10000 158.5 7700 158.5 8800 199.5 10500 5000 228.5 17600 259.0 13800 353 95.5 7200 0 151.5 12000 50 217.0 10600 257.5 12200 311.0 15600 1: Oil extracted from Milk Thistle (Silybum marianum) seeds obtained from Sentjernej, Slovenia. Source: Skerget, M.; Kotnik, P.; Knez, Z. J. Supercrit. Fluids (2003), 26(3), 181-191.

w x 106

T (K) 313

313 K 333 K 353 K

150

250 P (bar)

Molybdenumhexacarbonyl (C6MoO6; MW=264.00) P (bar)

y1 x

[M-58]

106

1000 313.45 79 950 313.55 80 313.85 4760 88 4780 313.85 89 313.15 10510 90 9080 314.05 91 313.55 10510 92 14510 313.45 93 950 323.05 79 4760 323.05 97 323.85 4780 98 323.85 9080 104 10510 323.85 105 324.05 9080 105 14510 322.85 107 950 333.05 61 9080 333.55 113 10510 333.25 115 333.35 118 14510 Synonym: Hexacarbonylmolybdenum Source: Warzinski, R.; Lee, C.; Holder, G. J. Supercrit. Fluids (1992), 5(1), 60-71.

15000 313 K 323 K 333 K

10000 y x 106

T (K)

350

5000

0 50

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90 P (bar)

130

506

Solubility in Supercritical Carbon Dioxide

Monensin sodium salt (C36H61NaO11; FW=692.86) T (K)

P (bar)

[M-59]

Cosolvent1)

Pure CO2 CO2+MeOH CO2+H2O

y x 106

y x 106 (wt%) 12 353.15 201 0 0.904 277 0 0.957 309 0 1.977 8 408 0 3.029 Methanol 185 1 0.614 243 1 2.860 4 316 1 6.870 402 1 10.800 Water 182 Saturated 0.635 0 242 Saturated 0.555 100 316 Saturated 0.877 401 Saturated 1.430 1: Cosolvent in CO2. Source: Maxwell, R.; Hampson, J.; CygnarowiczProvost, M. J. Supercrit. Fluids (1992), 5(1), 31-37.

200

300 P (bar)

Monocrotaline1) (C16H23NO6; MW=325.36) P (bar)

308.15

88.6 103.4 118.1 147.7 184.6 221.5 274.1 88.6 103.4 118.1 147.7 184.6 221.5 274.1 88.6 103.4 118.1 147.7 184.6 221.5 274.1 88.6 103.4 118.1 147.7

318.15

Ethanol2) (mol%) 0 0 0 0 0 0 0 5 5 5 5 5 5 5 10 10 10 10 10 10 10 0 0 0 0

[M-60]

y x 106 6.7 8.0 9.0 17.1 21.0 25.4 32.3 66.0 73.8 74.8 82.1 114.0 131.0 149.0 172.0 179.0 179.0 182.0 202.0 210.0 216.0 6.0 7.2 10.1 18.1

300

308.2 K, 0% 308.2 K, 5% 308.2 K, 10% 318.2 K, 0% 318.2 K, 5% 318.2 K, 10% 328.2 K, 0% 328.2 K, 5% 328.2 K, 10%

200 y x 106

T (K)

400

100

0 0

100

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200 P (bar)

300

Solubility Data M

0 0 0 5 5 5 5 5 5 10 10 10 10 10 0 0 0 0 0 0 0 5 5 5 5 5 5 10 10 10 10 10 10

21.0 28.9 38.0 65.0 69.0 78.1 111.0 135.0 170.0 146.0 150.0 162.0 183.0 199.0 6.2 8.0 11.9 20.5 23.8 33.0 44.3 44.0 49.4 68.9 119.0 137.0 182.0 126.0 139.0 153.0 172.0 197.0 221.0

308 K, 103 bar 308 K, 184 bar 308 K, 274 bar 318 K, 103 bar 318 K, 184 bar 318 K, 274 bar 328 K, 103 bar 328 K, 184 bar 328 K, 274 bar

300

y x 106

328.15

184.6 221.5 274.1 103.45 118.15 147.75 184.65 221.55 274.15 103.4 118.1 147.7 184.6 221.5 88.6 103.4 118.1 147.7 184.6 221.5 274.1 103.4 118.1 147.7 184.6 221.5 274.1 103.4 118.1 147.7 184.6 221.5 274.1

507

200

100

0 0

5

10

Ethanol (mol%)

1: A lipid extracted from Crotalario spectabilis seeds. 2: Cosolvent in CO2. Source: Schaeffer, S. T.; Zalkow, L. H.; Teja, A. S. Fluid Phase Equil. (1988), 43(1), 45-56.

Monocrotaline1) (C16H23NO6; MW=325.36) T (K) 308.15

P (bar) 88.6

118.1

Ethanol2) (mol%)

0 2 4 5 6 8 2 4 5

y x 106 0 0 160 170 180 215 40 80 110

CAT4240—CHAPTER 13—31/10/2006—19:16—KADAMBADI—XML MODEL C – pp. 477–512

[M-61]

508

Solubility in Supercritical Carbon Dioxide

221.5

274.1

318.15

103.4

118.1

147.7

184.6

221.5

400 88.6 bar 118.1 bar 147.7 bar 184.6 bar 221.5 bar 274.1 bar

300 y x 106

184.6

160 360 0 0 80 120 170 250 340 0 10 50 70 90 0 50 80 100 170 280 0 0 50 80 150 0 0 20 50 100 200 360 30 60 140 190 300 420 0 20 60 130 260 0 0 120 180 240 0 120 220 310 550

308.15 K

200

100

0 0

5

10

Ethanol (mol%)

600 103.4 bar 118.1 bar 147.7 bar 184.6 bar 221.5 bar 274.1 bar

400 y x 106

147.7

6 8 0 2 4 5 6 8 10 0 2 4 5 6 2 4 5 6 8 10 0 2 4 5 6 0 2 4 5 6 8 10 2 4 5 6 8 10 0 2 4 5 6 0 2 4 5 6 2 4 5 6 8

318.15 K

200

0 0

5 Ethanol (mol%)

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10

Solubility Data M

509

0 0 2 0 4 100 5 250 6 390 328.15 103.4 0 0 2 0 4 20 5 40 6 80 8 90 10 130 118.1 2 0 800 4 30 5 60 6 110 8 220 10 330 147.7 0 0 2 0 4 50 400 5 90 6 160 8 320 10 470 184.6 0 0 2 30 4 140 5 220 0 6 300 0 8 470 10 640 221.5 2 0 4 180 5 260 6 330 8 480 274.1 0 0 2 20 4 240 5 350 6 460 8 700 1: A lipid extracted from Crotalario spectabilis seeds. 2: Cosolvent in CO2. Source: Schaeffer, S. T.; Zalkow, L. H.; Teja, A. S. Biotech. Bioeng. (1989), 34(11), 1357-1365.

y x 106

274.1

103.4 bar 118.1 bar 147.7 bar 184.6 bar 221.5 bar 274.1 bar 328.15

5 Ethanol (mol%)

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10

510

Solubility in Supercritical Carbon Dioxide

Monolaurin (C15H30O4; MW=274.40)

[M-62]

106

6000 y x 106

yx T (K) P (bar) 313 150 521 250 763 300 932 350 1129 400 1211 338 350 4974 Synonyms: Glycerin monolaurate; Glycerol monododecanoate Source: Ashour, I.; Hammam, H. J. Supercrit. Fluids (1993), 6(1), 3-8. (See the graph in Hammam, H. J. Supercrit. Fluids (1992), 5(2), 101-106).

313 K 338 K

3000

0 100

200

300 P (bar)

Monoolein (C21H40O4; MW=356.55)

400

[M-63] 308.15 K 333.15 K

y x 106

T (K) P (bar) y x 106 308.15 103.7 73 114.1 87 200 127.2 92 146.8 108 152.0 147 167.8 171 100 178.9 235 333.15 132.7 23 143.0 24 0 156.8 25 174.0 87 100 189.2 108 Synonyms: Glycerin monooleate; Glycerol monooleate Source: King, M. B.; Alderson, D. A.; Fallah, F. H.; Kassim, D. M.; Sheldon, J. R.; Mahmud, R. S. in: Chapter 2, Chemical Engineering at Supercritical Fluid Conditions, Paulaitis, M. E.; Penninger, J. M. L.; Gray, Jr., R. D.; Davidson, P. (Eds.) Ann Arbor Science, 1983, pp.31-80.

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150 P (bar)

200

Solubility Data M

511

Monoolein (C21H40O4; MW=356.55) 106

y1)

[M-64]

106

323.15 K 333.15 K

y x 106

wx x T (K) P (bar) 1500 323.15 151 2200 272 172 3500 433 206 5000 620 1000 241 7200 894 275 8000 994 333.15 151 1300 161 500 172 2600 322 206 4400 545 241 6900 857 0 275 7900 982 309 10900 1358 100 1: Calculated from w. Synonyms: Glycerin monooleate; Glycerol monooleate Source: Nilsson, W. B.; Gauglitz, E. J. Jr.; Hudson, J. K. J. Am. Oil Chem. Soc.(1991), 68(2), 87-91.

200

300

P (bar)

Myristic acid (C14H28O2; MW=228.37)

[M-65]

106

12000 y x 106

yx T (K) P (bar) 313 82 16 90 481 111 1700 150 4140 150 4210 202 7810 249 11300 Synonym: Tetradecanoic acid Source: Bamberger, T.; Erickson, J. C.; Cooney, C. L.; Kumar, S. K. J. Chem. Eng. Data (1988), 33(3), 327-333.

6000

0 0

100

200

Myristic acid (C14H28O2; MW=228.37)

[M-66]

106

6000 y x 106

yx T (K) P (bar) 308.15 81 343 99 1160 128 2310 148 3330 197 4030 228 4340 Synonym: Tetradecanoic acid Source: Iwai, Y.; Fukuda, T.; Koga, Y.; Arai, Y. J. Chem. Eng. Data(1991), 36(4), 430-432.

300

P (bar)

3000 0 50

150 P (bar)

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250

512

Solubility in Supercritical Carbon Dioxide

Myristic acid (C14H28O2; MW = 228.37) T (K)

P (bar)

W (g/kg CO2)

[M-67]

y1) x 106

120000

140 14 2690 272 26 4990 396 25 4800 313 152 32 6130 80000 207 44 8400 276 87 16500 318 139 9 1670 272 73 13900 40000 419 620 106700 323 152 30 5750 207 49 9360 276 74 14100 328 144 5 960 0 266 70 13300 100 333 152 21 4000 207 41 7840 276 120 22600 1: Calculated from W. Synonym: Tetradecanoic acid Source: Maheshwari, P.; Nikolov, Z.; White, T.; Hartel, R. J. Am. Oil Chem. Soc. (1992), 69(11), 1069-76. (See the graph in Nikolov, Z.; Maheshwari, P.; Hardwick, J.; Murphy, P.; Johnson, L. Develop. Food Sci. (1992), 29, 595-616.)

y x 106

308

308 K 313 K 318 K 323 K 328 K 333 K

200

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300 P (bar)

400

14

Solubility Data N

Naphthalene (C10H8; MW=128.17)

[N-1] 60000 y x 106

y x 106 T (K) P (bar) 318 83.0 900 103.0 8900 139.0 19800 172.0 22300 207.0 24300 276.0 25200 328 112.0 5800 138.0 22300 172.0 32300 276.0 54600 Source: Chang, H.; Morrell, D. G. J. Chem. Eng. Data (1985), 30(1), 74-78.

318 K 328 K

30000

0 50

150 P (bar)

Naphthalene (C10H8; MW=128.17) T (K)

P (bar)

[N-2]

y x 106

45000

308.2

308.2 K 328.2 K

30000 y x 106

98.0 9730 106.2 11100 133.3 14500 171.0 16000 200.5 17100 328.2 92.2 1630 102.8 2970 110.5 5500 121.7 12200 133.1 20700 143.5 25300 160.6 30500 171.6 33300 174.8 33700 190.0 37900 Source: Chen, J. W.; Tsai, F. N. Fluid Phase Equil. (1995), 107(2), 189-200.

250

15000

0 50

100

150

200

P (bar)

513

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514

Solubility in Supercritical Carbon Dioxide

Naphthalene (C10H8; MW=128.17) T (K)

P (bar)

[N-3]

106

yx 62.8 0 180000 73.9 400 77.5 1600 79.2 5000 86.3 7100 120000 104.0 10000 138.5 13100 173.0 15000 208.5 16700 60000 264.3 17900 338.15 98.4 3100 117.4 5500 0 138.5 16000 165.5 37400 0 200.9 66500 242.1 108000 261.9 155000 Source: Chung, S. T.; Shing, K. S. Fluid Phase Equil. (1992), 81, 321-341. 308.15

y x 106

308.15 K 338.15 K

100

200

300

P (bar)

Naphthalene (C10H8; MW=128.17)

[N-4]

106

y x 106

yx T (K) P (bar) 308 88 6000 20000 93 9000 99 10200 106 11600 109 11700 15000 117 11200 120 12400 128 13800 10000 132 14200 136 14300 139 13800 5000 144 15400 50 152 16400 163 14300 205 16800 208 17500 Source: Diefenbacher, A.; Turk, M. J. Supercrit. Fluids (2002), 22(3), 175-184.

CAT4240—CHAPTER 14—1/11/2006—17:04—SRIDHAR—XML MODEL C – pp. 513–568

150 P (bar)

250

Solubility Data N

515

Naphthalene (C10H8; MW=128.17)

[N-5]

106

313.15 K 318.15 K 323.15 K

y x 106

T (K) P (bar) M (mol/L) yx 14600 313.15 124.2 0.241 16000 135.6 0.276 16400 144.9 0.287 17800 162.8 0.323 40000 19000 187.6 0.358 19900 207.6 0.383 20800 232.1 0.410 20400 261.3 0.412 15100 318.15 122.5 0.230 30000 17800 135.3 0.286 19500 147.5 0.327 21600 168.2 0.380 22600 181.3 0.408 23800 203.0 0.442 20000 24400 223.4 0.465 25200 245.1 0.488 25900 280.6 0.516 12100 323.15 120.1 0.161 19000 139.2 0.289 10000 21600 149.0 0.343 100 24800 165.2 0.415 28000 185.4 0.486 30100 205.6 0.542 31600 222.0 0.580 33000 244.5 0.623 34000 265.4 0.656 34900 286.6 0.684 304.7 0.703 35400 Source: Hourri, A.; St-Arnaud, J. M.; Bose, T. K. Rev. Sci. Instrum. (1998), 69(7), 2732-2737.

200

300

P (bar)

[N-6]

Naphthalene (C 10 H 8 ; MW=128.17) y x 106 8300 10660 13590 15210 16610 8430 17620 22330 24890

30000 308.2 K

y x 106

T (K) P (bar) 308.2 91.3 104.3 138.2 172.8 206.9 318.2 103.1 137.9 172.0 206.9

Source: Kaiaga, A.; Trebble, M. J. Chem. Eng. Data (1999), 44(5), 1063-1066.

318.2 K

20000 10000 0 50

100

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150 P (bar)

200

250

516

Solubility in Supercritical Carbon Dioxide

Naphthalene (C10H8; MW=128.17) T (K)

P (bar)

yx

[N-7]

106

14000

81.0 3400 90.6 5800 94.8 3900 97.5 5800 102.4 8000 112.7 8600 119.6 10300 125.1 11500 Source: King, M. B.; Alderson,D. A.; Fallah, F. H.; Kassim, D. M.; Sheldon, J. R.; Mahmud, R. S. in: Chapter 2, Chemical Engineering at Supercritical Fluid Conditions, Paulaitis, M. E.; Penninger, J. M. L.; Gray, R. D., Jr.; Davidson, P. (Eds.) Ann Arbor Science,1983, pp. 31-80.

y x 106

308.15

8000

2000 70

100 P (bar)

130

Naphthalene (C10H8; MW=128.17)

[N-8]

106

y x 106

yx T (K) P (bar) 323.15 120 14100 160 24300 200 28600 240 32800 270 36000 300 37900 375 39000 450 38700 328.15 120 9800 160 28200 200 41700 240 47600 280 51600 320 53100 400 51200 500 47900 331.65 120 5670 160 28100 180 36200 200 43400 220 48700 230 48600 240 58100 250 58300 280 61100 320 64000 400 63600 62200 500 Source: Lamb, D. M.; Barbara, T. M.; Jonas, J. J. Phys. Chem. (1986), 90(17), 4210-4215.

60000

40000

20000

0 100

323.15 K 328.15 K 331.65 K

200

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300 P (bar)

400

500

Solubility Data N

517

Naphthalene (C10H8; MW=128.17)

338.1

151.8 171.6 185.2

[N-9]

y x 106 7500 9750 10660 14100 16050 17090 18300 19080 19220 1313 1672 2920 5464 12290 21140 25440 30530 33870 34730 39280 42240 43660 45860 49690 53820 5238 15160 25890 34010 42960 44360 53860 59030 62590 69630 69900 77200 77210 83060 90640 92040 95830 97560 98020

100000 308.2 K 328.2 K 333.6 K 338.1 K

75000 y x 106

T (K) P (bar) 308.15 86.8 98.2 106.5 133.0 169.0 199.5 222.4 242.5 255.3 328.15 82.2 92.3 102.3 109.7 121.7 133.2 143.7 160.6 171.6 174.9 189.6 210.4 223.5 237.8 251.6 287.8 333.55 108.4 133.9 152.5 164.2 175.6 183.7 192.6 204.0 206.1 217.0 217.4 226.6 231.9 235.9 248.1 255.0 257.8 273.3 291.4

50000

25000

0 50

24270 37650 44280

CAT4240—CHAPTER 14—1/11/2006—17:04—SRIDHAR—XML MODEL C – pp. 513–568

150 P (bar)

250

518

Solubility in Supercritical Carbon Dioxide

192.3 213.0 225.0 232.2

50150 64400 73090 79020

Source: McHugh, M.; Paulaitis, M. E. J. Chem. Eng. Data (1980), 25(4), 326-329.

Naphthalene (C10H8; MW=128.17) 309.15

328.15

P (bar) 75.4 104.4 138.9 173.4 207.9 242.3 276.8 76.9 104.4 138.9 173.4 207.9 242.3 276.8

yx

804 10000 13230 14890 17540 18740 19610 1389 3470 23340 35160 44770 50670 55040

60000

y x 106

T (K)

[N-10]

106

309.2 K 328.2 K

40000

20000

0 0

100

200

300

P (bar)

Source: Mitra, S.; Chen, J. W.; Viswanath, D. S. J. Chem. Eng. Data (1988), 33(1), 35-37.

[N-11]

Naphthalene (C10H8; MW=128.17) 308.15

P (bar) 71.9 77.5 84.8 86.6 86.9 87.6 89.4 89.7 90.0 90.3 90.8 90.8 91.4 92.0 92.9 92.9 93.8 93.8 94.1 94.1 94.4 96.2 96.2

y x

740 520 3660 3340 7670 7870 6430 8810 8800 8110 8520 7960 9340 9530 10400 10600 9710 9660 9140 9910 10300 10500 10900

20000

15000 y x 106

T (K)

106

10000

5000

0 0

100

CAT4240—CHAPTER 14—1/11/2006—17:04—SRIDHAR—XML MODEL C – pp. 513–568

200 P (bar)

300

400

Solubility Data N

519

97.4 11000 97.4 10500 97.6 11400 102.3 12100 102.3 12100 106.6 12400 106.6 12600 115.9 13400 116.5 13500 124.8 15200 125.0 14400 136.6 15500 136.6 14700 146.0 15400 146.3 15600 165.6 15300 166.1 16300 181.5 17100 187.8 17300 188.8 16900 189.0 16900 194.6 16100 197.4 17700 209.0 18200 209.2 18300 214.4 18100 228.0 17900 260.1 18100 260.8 17600 279.5 17400 279.7 18300 300.5 18300 300.8 17700 319.3 17600 321.5 18500 Source: Pauchon, V.; Cisse, Z.; Chavret, M.; Jose, J. J. Supercrit. Fluids (2004), 32(1-3), 115-121.

Naphthalene (C10H8; MW=128.17)

[N-12]

106

18000 y x 106

T (K) P (bar) y x 308.15 121.8 12700 135.8 13900 142.3 14600 152.9 15200 157.6 15500 167.2 16000 167.9 16200 188.8 16800 189.1 16900 204.0 17300 Source: Sako, S.; Ogaki, K.; Katayama, T. J. Supercrit. Fluids (1988), 1(1), 1-6.

15000

12000 100

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150 P (bar)

200

520

Solubility in Supercritical Carbon Dioxide

Naphthalene (C10H8; MW=128.17)

[N-13]

106

308 K 318 K 328 K 338 K

y x 106

yx T (K) P (bar) 308 88.3 9750 114.7 13080 134.4 14570 157.9 15850 186.3 16230 197.1 16320 228.5 16620 251.0 17890 288.3 18290 318 83.4 1110 89.2 1960 60000 92.2 5710 97.1 8090 100.0 9950 122.3 17020 151.0 20690 40000 204.0 24160 227.5 26640 265.8 28680 300.1 29350 20000 328 77.5 930 98.1 3140 109.8 7610 117.7 12530 0 133.4 22360 50 138.3 24340 154.9 30120 181.4 37420 218.7 43980 268.7 51390 338 117.7 7340 127.5 10820 147.1 25950 160.8 33500 187.3 46310 199.1 51040 218.7 58940 225.6 63940 Source: Sako, T.; Yamane, S.; Negishi, A.; Sato, M. Sekiyu Gakkaishi (1994), 37(3), 321-327.

CAT4240—CHAPTER 14—1/11/2006—17:04—SRIDHAR—XML MODEL C – pp. 513–568

150 P (bar)

250

Solubility Data N

521

Naphthalene (C10H8; MW=128.17)

318.15

P (bar) 81 134 135 149 151 200 201 248 298 299 85 98 147 151 153 198 250 297

yx

30000

4400 13800 13900 14600 14700 16100 16300 16900 17400 17500 1100 6000 20600 20800 21500 23700 25800 27800

308.15 K 318.15 K

y x 106

T (K) 308.15

[N-14]

106

20000

10000

0 0

100

200

300

P (bar)

Source: Sauceau, M.; Fages, J.; Letoumeau, J. J.; Richon, D. Ind. Eng. Chem. Res. (2000), 39(12), 4609-4614.

Naphthalene (C10H8; MW=128.17) (bar)

46.8 60.8 70.8 71.6 74.9 75.6 75.7 75.7 75.8 75.8 76.0 76.0 76.0 77.1 77.4 81.4 82.5 89.3 104.7 119.3 156.1 165.7 165.7 214.0

w2)

(wt%) 0.18 0.07 0.12 0.14 0.30 0.63 0.71 0.77 0.83 0.81 1.03 1.05 1.05 1.61 1.53 1.90 2.09 2.36 2.86 3.24 4.16 3.74 4.03 4.72

y3)

x

[N-15]

106

620 240 410 480 1030 2170 2450 2660 2870 2800 3560 3630 3630 5590 5310 6610 7280 8230 10000 11400 14700 13200 14200 16800

20000 307.75 K 308.65 K 318.15 K

15000 y x 106

T (K) 307.75

P1)

10000

5000

0 0

CAT4240—CHAPTER 14—1/11/2006—17:04—SRIDHAR—XML MODEL C – pp. 513–568

100 P (bar)

200

522

Solubility in Supercritical Carbon Dioxide

308.65

71.6 0.14 480 74.1 0.30 1030 74.6 0.33 1140 74.9 0.34 1170 75.2 0.39 1340 75.4 0.49 1690 76.0 1.09 3770 76.1 1.17 4050 76.5 1.40 4850 77.1 1.58 5480 318.15 70.0 0.19 650 70.9 0.18 620 71.6 0.24 830 74.9 0.42 1450 1140 75.0 0.33 1: Calculated from temperature and density in the source table. 2: Measured in a glass vial with a volume of 1.5 cm3. The data in italics were measured in a small column with a volume of 23.3 cm3. 3: Calculated from w. Source: Tsekhanskaya, Yu. V.; Iomtev, M. B.; Mushkina, E. V. Z. Fiz. Khim. (1962), 36, 2187-2193.

Naphthalene (C10H8; MW=128.17) yx

240 750 870 1070 1370 3010 4760 6110 8110 9200 11000 11700 12500 13200 13900 14600 15100 16300 17400 17700 18400 18700

60000 308.15 K 318.15 K 328.15 K

40000 y x 106

T (K) P (bar) 308.15 60.8 76.0 77.0 78.0 79.0 79.5 80.5 81.0 87.1 92.2 106.4 111.4 121.6 131.7 141.8 152.0 162.1 192.5 222.9 243.1 293.8 334.3

[N-16]

106

20000

0 0

100

CAT4240—CHAPTER 14—1/11/2006—17:04—SRIDHAR—XML MODEL C – pp. 513–568

200 P (bar)

300

400

Solubility Data N

318.15

328.15

62.8 72.9 78.0 82.1 85.6 88.1 92.2 95.7 97.8 99.3 101.3 106.4 109.4 119.5 126.6 141.8 155.0 202.6 278.6 314.0 77.0 92.2 94.2 99.3 102.3 106.4 111.4 114.5 116.5 119.5 122.6 125.6 131.7 142.8 152.0 162.1 172.2 182.3 197.5 233.0 253.3 324.2

523

470 480 670 780 1100 1300 2100 4300 5100 6100 6900 9700 11300 14200 15400 18300 19700 24500 28500 29400 1100 2400 2000 2400 3000 4200 6100 7700 9200 10800 12700 14200 18100 23400 26400 30000 32400 35600 39900 45900 48500 55000

Source: Tsekhanskaya, Yu. V.; Iomtev, M. B.; Mushkina, E. V. Z. Fiz. Khim. (1964), 38(9), 2166-2171.

CAT4240—CHAPTER 14—1/11/2006—17:04—SRIDHAR—XML MODEL C – pp. 513–568

524

Solubility in Supercritical Carbon Dioxide

Naphthalene (C10H8; MW=128.17)

[N-17]

106

80 bar 85 bar 90 bar 95 bar 100 bar

y x 106

yx P (bar) T (K) 80.0 310.75 1460 313.55 1080 318.25 910 323.15 950 328.05 910 333.05 910 85.0 308.05 7480 310.45 6710 311.05 5350 8000 313.05 3220 313.65 2320 316.15 1730 318.55 1440 6000 323.15 1280 328.45 1120 333.75 1210 90.0 311.15 6880 4000 313.65 6190 315.45 4570 317.95 2900 322.85 1830 2000 328.35 1570 333.25 1500 95.0 310.75 7570 313.35 6730 0 315.45 6480 300 318.15 5600 318.45 5150 321.35 3070 323.15 2610 328.15 1830 100.0 315.35 7220 317.85 6580 320.75 5620 323.45 4320 325.65 3530 328.35 2860 333.15 2360 Source: Zhao, S.; Wang, R.; Yang, G. J. Supercrit. Fluids (1995), 8(1), 15-19.

310

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320 T (K)

330

340

Solubility Data N

525

Naphthalene (C10H8; MW=128.17)

[N-18]

Ethane1) y x 106 (mol%) 308 58.7 50.4 280 73.4 50.4 1050 78.4 50.4 3340 40000 83.4 50.4 4800 91.1 50.4 7960 112.1 50.4 12370 151.7 50.4 17920 30000 176.1 50.4 21620 69.9 60.1 1620 71.4 60.1 2760 75.7 60.1 4800 20000 104.9 60.1 11800 159.9 60.1 21200 206.2 60.1 27400 10000 302.5 60.1 32340 318 58.7 52.6 500 77.1 52.6 1900 99.6 52.6 9910 0 188.7 52.6 35700 0 69.0 74.6 1710 72.5 74.6 4730 74.4 74.6 2890 84.3 74.6 11580 109.0 74.6 21960 113.1 74.6 21180 1: Cosolvent in CO2 on a solute-free basis. Source: Hollar, W. E., Jr.; Ehrlich, P. J. Chem. Eng. Data (1990), 35(3), 271-275. P(bar)

y x 106

T(K)

308 K, 50.4% 308 K, 60.1% 318 K, 52.6% 318 K, 74.6%

100

200

300

P (bar)

Naphthalene (C10H8; MW=128.17)

308.15

328.15

P (bar) 140 175 209 244 127 153 175 208 149 157 176 211 244

n-Pentane1) (mol%) 0.0 0.0 0.0 0.0 4.1 4.1 4.1 4.1 4.1 4.1 4.1 4.1 4.1

y x 106 15500 17400 18500 19300 23000 23600 25800 26800 59800 64800 71500 87500 93100

150000

0.0% 308 K 4.1% 308 K 4.1% 328 K 8.0% 326 K

100000

y x 106

T (K)

[N-19]

50000

0 50

100

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150 P (bar)

200

250

526

Solubility in Supercritical Carbon Dioxide

326.15

112 bar 139 bar

y x 106

96 8.0 43300 102 8.0 51600 108 8.0 58100 115 8.0 66100 121 8.0 76800 120000 124 8.0 84200 150 8.0 96700 168 8.0 103000 8000 111000 193 8.0 308.15 112 8.5 29400 313.15 112 8.5 41400 318.15 112 8.5 47200 40000 323.15 112 8.5 62100 326.15 112 8.5 81800 308.15 139 8.5 32800 313.15 139 8.5 41600 0 318.15 139 8.5 52100 305 323.15 139 8.5 73900 101000 326.15 139 8.5 1: Cosolvent in CO2 on a solute-free basis. Source: Lemert, R. M.; Johnston, K. P. Fluid Phase Equil. (1990), 59(1), 31-55.

315

325 T (K)

Naphthalene (C10H8; MW=128.17)

[N-20]

Ethane1) y x 106 40000 (mol%) 308.15 99.0 6.2 9300 104.0 6.2 10200 30000 112.0 6.2 11300 122.0 6.2 13100 147.0 6.2 14000 198.0 6.2 17500 20000 284.0 6.2 19000 364.0 6.2 20800 318.15 99.0 6.2 1900 10000 104.0 6.2 8100 112.0 6.2 11600 122.0 6.2 14800 0 147.0 6.2 18700 100 198.0 6.2 25400 284.0 6.2 31900 364.0 6.2 34200 1: Cosolvent in CO2. Source: Schmitt, W. J.; Reid, R. C. Fluid Phase Equil. (1986), 32(1), 77-99. P (bar)

y x 106

T (K)

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308 K 318 K

200

300 P (bar)

400

Solubility Data N

527

Naphthalene (C10H8; MW=128.17)

307.9

323.0

328.0

333.0

P (bar) 60.9 71.0 87.0 91.0 101.0 111.0 121.0 141.0 161.0 181.0 202.0 222.0 262.0 242.0 81.0 101.0 122.0 141.0 162.0 182.0 202.0 222.0 242.0 262.0 81.0 101.0 121.0 132.0 151.0 161.0 171.0 181.0 192.0 202.0 212.0 222.0 232.0 242.0 262.0 81.0 102.0 121.0 141.0 152.0

[N-21]

y2) x 106 420 1290 8530 9560 12600 15300 17200 20400 24500 25500 27500 29200 29500 28300 4550 10740 23800 35000 47640 56240 65500 70100 82200 82520 2570 11500 31500 33700 55700 84300 10350 166800 19050 222900 235300 210100 207900 202000 176200 2410 7840 26400 46200 61000

250000 200000

y x 106

T (K)

Ethane1) (mol %) 56.9 57.4 59.1 57.6 55.6 57.4 56.4 55.3 54.8 59.6 54.9 59.7 59.0 59.1 57.8 57.8 57.7 57.4 63.8 63.8 63.9 64.2 62.3 62.5 63.8 63.5 62.8 57.0 57.0 59.6 55.5 59.7 52.4 60.4 57.0 60.8 56.8 60.9 63.1 61.9 61.2 61.2 61.7 61.1

307.9 K 323.0 K 328.0 K 333.0 K

150000 100000 50000 0 50

1: Cosolvent in CO2 on a solute-free basis. Source: Smith, G. R.; Wormald, C. J. Fluid Phase Equil. (1990), 57(1-2), 205-222.

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150 P (bar)

250

528

Solubility in Supercritical Carbon Dioxide

Naphthalene (C10H8; MW=128.17) T (K)

P (bar)

Propane1) (mol %)

[N-22]

y x 106

308.3

308.3 K 323.3 K 327.5 K 328.3 K

y x 106

60.9 15.6 520 71.0 15.6 12800 80.0 15.2 16600 90.0 15.2 19100 111.0 15.2 22700 141.0 15.2 24200 171.0 15.0 26900 150000 202.0 15.6 31500 232.0 15.5 33400 323.3 60.9 14.9 510 81.0 14.9 2230 92.0 16.1 17800 100000 101.0 15.0 26600 122.0 15.0 41500 142.0 14.8 51400 161.0 15.4 58600 181.0 16.0 69400 50000 212.0 16.0 74800 243.0 16.4 78500 327.5 126.0 15.0 56900 137.0 14.8 80400 145.0 15.0 87500 0 146.0 15.0 142100 50 151.0 14.0 98800 151.0 15.4 123900 156.0 15.4 112900 157.0 15.0 121900 166.0 14.8 107900 177.0 15.2 84500 328.3 86.0 15.2 3050 102.0 15.2 24100 111.0 15.2 40100 121.0 15.2 60700 131.0 15.3 77700 141.0 15.2 111900 1. Cosolvent in CO2 on a solute-free basis. Source: Smith, G. R.; Wormald, C. J. Fluid Phase Equil. (1990), 57(1-2), 205-222.

CAT4240—CHAPTER 14—1/11/2006—17:04—SRIDHAR—XML MODEL C – pp. 513–568

150 P (bar)

250

Solubility Data N

529

Naphthalene (C10H8; MW=128.17) T (K)

P (bar)

M x 102 (mol/L)

[N-23]

y1) x 106 308 K 328 K

40000

y x 106

86 15 9900 10200 88 15 11000 91 17 11800 96 19 13700 119 24 14000 150 26 174 30 15300 206 35 17100 228 35 17200 276 37 17200 301 39 18100 80 1 328 2600 101 3 3600 107 8 8400 122 22 18300 147 45 29400 172 57 34300 194 72 40400 251 95 48700 300 106 51900 1: Calculated from M. Source: Wagner, K.-D.; Dahmen, N.; Dinjus, E., J. Chem. Eng. Data (2000), 45(4), 672-677.

60000

308

20000

0

0

100

200 P (bar)

Naphthalene (1) + Benzoic acid (2) Mixture T (K)

P (bar)

y1 x

106

y2 x

[N-24]

106

308

40000 y x 106

120 14400 2930 160 17300 4010 200 20600 5220 240 20800 5460 21200 5610 280 318 120 17600 3490 160 26100 6960 200 32500 10000 240 36700 12100 36600 12600 280 Source: Kurnik, R. T.; Reid, R. C. Fluid Phase Equil. (1982), 8(1), 93-105.

300

Naph 308 K Naph 318 K Benz 308 K Benz 318 K

20000

0 100

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200 P (bar)

300

530

Solubility in Supercritical Carbon Dioxide

Naphthalene (1) + Biphenyl (2) Mixture1) 106

[N-25]

106

Naph 308 K Naph 318 K BiPh 308 K BiPh 318 K

y x 106

y1 x y2 x T (K) P (bar) 308 57 140 30 73 410 80 30000 87 1210 460 104 4740 4060 121 10050 8390 139 10550 9160 156 13320 10690 20000 174 16950 15400 191 19710 17350 208 22950 21250 243 23100 21800 278 24900 23000 10000 318 60 310 80 69 380 120 87 710 270 104 2520 1080 121 3430 2200 0 139 6640 5690 0 156 8910 7420 174 11250 9430 191 14700 12400 208 17200 15100 243 21900 20600 278 24800 22600 1: Initial composition of the mixture of 1 and 2 = 45:55 (mol%). Source: Gopal, J. S.; Holder, G. D.; Kosal, E. Ind. Eng. Chem. Proc. Des. Dev. (1985), 24(3), 697-701.

100

200

P (bar)

Naphthalene (1) + Biphenyl (2) Mixture

308.15

P (bar) 77.9 82.7 96.4 119.1 186.1 246.1 78.2 87.0 107.9 140.2 188.1 244.9 280.1

y1 x 106

xov1)= 0.25 2600 3700 6300 9000 12500 14200 1) xov = 0.62 7300 11600 17100 21800 29300 35300 40100

y22)x 106 4600 7100 12700 22400 30000 30500 2900 4700 7400 10300 15000 19800 22700

[N-26] 45000 NP Xov=0.25 NP Xov=0.62 NP Xov=0.75 BP Xov=0.25 BP Xov=0.62 BP Xov=0.75

30000 y x 106

T (K)

300

15000

0

0

100

200 P (bar)

CAT4240—CHAPTER 14—1/11/2006—17:04—SRIDHAR—XML MODEL C – pp. 513–568

300

Solubility Data N

531

xov1)= 0.75 77.7 7100 2700 87.3 11900 4700 106.4 16600 7100 140.9 22200 10900 175.8 27800 14600 215.4 33000 19300 271.7 39400 25900 1: Initial (overall) composition of naphthalene (mole fraction). 2: The authors confirmed the large biphenyl data at xov= 0.25. Source: Chung, S. T.; Shing, K. S. Fluid Phase Equil. (1992), 81, 321-341.

Naphthalene (1) + 2,3-Dimethylnaphthalene (2) Mixture 30000 y1 x 106 y2 x 106 T (K) P (bar) 308

y x 106

120 18500 6520 160 24100 8800 200 23900 9340 240 25800 9950 26200 9900 280 Source: Kurnik, R. T.; Reid, R. C. Fluid Phase Equil. (1982), 8(1), 93-105.

[N-27]

Naph 2,3-DN

15000

0 100

200

300

P (bar)

Naphthalene (1) + 2,6-Dimethylnaphthalene (2) Mixture T (K)

P (bar)

y1 x

106

y2x

106

40000

303.15

y x 106

244 16200 4590 279 13100 4270 314 11500 4060 308.15 244 15200 5410 279 15600 5510 314 15000 5390 313.15 244 15800 6640 279 18500 7020 314 20700 8780 315.15 244 38200 11800 279 36600 11400 314 37600 11600 317.15 314 53400 17000 Source: Lemert, R. M.; Johnston, K. P. Fluid Phase Equil. (1990), 59(1), 31-55.

[N-28]

20000

Naph 303 K Naph 313 K Naph 315 K 2,6-DN 303 K 2,6-DN 313 K 2,6-DN 315 K

0 200

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250 P (bar)

300

350

532

Solubility in Supercritical Carbon Dioxide

Naphthalene (1) + Diphenylmethane (2) Mixture P (bar)

y1 x xov

106

y2 x

0.44 308.15 80.3 5200 5400 98.1 7700 8400 122.9 10600 12100 167.8 15700 18800 208.5 20900 26100 256.7 24900 31700 1: Initial (overall) composition of naphthalene (mole fraction). Source: Chung, S. T.; Shing, K. S. Fluid Phase Equil. (1992), 81, 321-341.

[N-29]

40000

1)=

y x 106

T (K)

106

Naph DPMe

20000

0 50

150

250

P (bar)

Naphthalene (1) + 2-Methylnaphthalene (2) Mixture T (K)

P (bar)

y1 x

106

y2x

106

60000

xov1)=

Naph 2-MeNp

y x 106

0.62 308.15 77.3 8600 4700 103.0 19000 10600 152.0 29900 17700 175.0 34200 20800 207.0 39500 24700 261.9 49700 34100 1: Initial (overall) composition of naphthalene (mole fraction). Source: Chung, S. T.; Shing, K. S. Fluid Phase Equil. (1992), 81, 321-341.

[N-30]

30000

0 0

100

200 P (bar)

Naphthalene (1) + Phenanthrene (2) Mixture T (K)

P (bar)

y1 x

106

y2 x

300

[N-31]

106

308

40000 y x 106

102.0 12900 1390 120.6 14670 1780 150.0 17000 2220 196.1 18450 2706 205.9 19100 2928 247.1 19670 3161 328 100.0 3550 100 125.5 17600 448 147.1 25240 842 171.6 32420 1522 249.1 49200 3459 Source: Sako, T.; Yamane, S.; Negishi, A.; Sato, M. Sekiyu Gakkaishi (1994), 37(3), 321-327.

Naph 308 K Naph 328 K Phen 308 K Phen 328 K

20000

0 50

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150 P (bar)

250

Solubility Data N

533

Naphthalene (1) + Phenanthrene (2) mixture T (K)

P (bar)

y1 x

106

y2 x

106

30000

308.2

Naph Phen

20000 y x 106

48.7 81 ND 60.2 194 ND 71.8 688 ND 81.7 9861 935 101.6 13411 543 120.9 16050 2059 139.6 17320 2302 158.1 18580 2469 178.7 20170 2990 200.4 21130 3096 220.7 22440 3425 241.3 23370 3931 261.4 22820 3908 282.3 22210 3683 ND : Not detectable. Source: Liu, G.-T.; Nagahama, K. J. Supercrit. Fluids (1996), 9(3), 152-160.

[N-32]

10000

0 0

100

200 P (bar)

Naphthalene (1) + Phenanthrene (2) Mixture1) T (K)

P (bar)

y1 x

106

y2 x

300

[N-33]

106

86 5280 462 100 12600 1021 20000 113 13710 1516 126 15170 1647 128 16360 1763 139 16920 2089 15000 154 19180 2410 167 16600 2205 181 16510 1570 10000 195 18700 2628 210 17940 1894 225 19170 2540 242 19050 2707 5000 280 18540 2674 318 77 1070 48 88 1870 103 106 3010 344 0 139 6510 944 50 173 11050 1158 207 15970 2048 242 17760 2333 15800 2461 278 1: Initial composition of the mixture of 1 and 2 = 40:60 (mol%). Source: Gopal, J. S.; Holder, G. D.; Kosal, E. Ind. Eng. Chem. Proc. Des. Dev. (1985), 24(3), 697-701.

y x 106

308

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Naph 308 K Naph 318 K Phen 308 K Phen 318 K

150 P (bar)

250

534

Solubility in Supercritical Carbon Dioxide

Naphthalene (1) + Phenol (2) Mixture1) y1 x 106 230 270 1590 9730 21030 19930 20970 20940 18800 19150 18150 260 500 1120 2100 15020 31550 45340 53370 52000

y2 x 106 290 360 1800 8230 9580 12000 18350 17000 16550 16810 18600 530 680 1720 3100 13360 30940 47340 56360 53000

60000 Naph Naph Phnol Phnol

308 K 318 K 308 K 318 K

40000 y x 106

T (K) P (bar) 308 54 61 76 87 105 123 140 174 208 243 277 318 64 76 88 107 139 174 208 243 277

[N-34]

20000

0 0

100

200

300

P (bar)

1: Initial composition of the mixture of the solutes 1 and 2 = 60:40 (mol%). Source: Gopal, J. S.; Holder, G. D.; Kosal, E. Ind. Eng. Chem. Proc. Des. Dev. (1985), 24(3), 697-701.

Naphthalene (1) + 2,5-Xylenol (2) Mixture T (K)

P (bar)

y1 x

106

y2 x

106

40000

308.15

y x 106

85 16500 12100 111 22600 17400 142 27600 21300 184 31200 24100 223 30900 24300 262 32100 24900 Source: Mori, Y.; Shimizu, T.; Iwai, Y.; Arai, Y. J. Chem. Eng. Data (1992), 37(3), 317-19.

[N-35]

20000 Naph Xylenol

0 50

a-Naphthol (C10H8O; MW=144.17) T (K) P (bar) 308.15 84.7 88.2 91.3 96.1 103.5

yx

106 99 145 187 271 324

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150 P (bar)

250

[N-36]

Solubility Data N

328.15

344 470 579 683 09 888 912 973 1063 66 71 74 82 148 298 352 401 486 547 687 826 948 1059 1183 1244 1307 1391 1446 40 45 59 71 103 118 198 284 328 588 804 987 1168 1284 1364 1542 1591 1647 1749 1788

2000 308.15 K 318.15 K 328.15 K

1500 y x 106

318.15

109.7 122.2 140.4 163.4 203.1 232.8 254.2 277.6 293.6 88.7 89.7 91.5 94.8 96.9 103.0 106.6 109.2 114.4 118.5 130.3 144.7 159.5 173.0 205.0 212.3 227.0 262.2 287.4 82.8 85.6 89.3 91.7 95.4 98.5 101.3 105.4 108.2 118.5 127.1 140.2 152.4 167.3 183.1 205.0 234.0 251.3 274.2 296.5

535

1000

500

0 50

Synonyms: 1-Naphthalenol; 1-Naphthol Source: Coutsikos, P.; Magoulas, K.; Tassios, D. J. Chem. Eng. Data (1995), 40(4), 953-958.

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150 P (bar)

250

536

Solubility in Supercritical Carbon Dioxide

a -Naphthol (C10H8O; MW=144.17)

[N-37]

106

2000 308 K 318 K 328 K

1500 y x 106

yx T (K) P (bar) 308 92.2 735 106.4 940 121.6 1040 131.7 1150 141.9 1210 162.1 1310 318 99.3 417 109.4 720 119.6 982 131.7 1150 141.9 1350 152.0 1470 328 106.4 330 116.5 530 125.6 830 142.9 1320 152.0 1470 172.3 1780 Synonyms: 1-Naphthalenol; 1-Naphthol Source: Tan, C. S.; Weng, J. Y. Fluid Phase Equil. (1987), 34(1), 37-47.

1000

500

0 50

100

150

a -Naphthol (1) +b -Naphthol (2) Mixture1) T (K) P2) (bar) y12) x 106

y22)

x

106

250 91 603 350 107 884 407 122 998 457 132 1138 507 142 1179 162 1272 557 1: Initial composition of the mixture of 1 and 2 = 50:50(%). 2: Obtained by digitizing the graph in the original article. Source: Tan, C. S.; Weng, J. Y. Fluid Phase Equil. (1987), 34(1), 37-47.

200

P (bar)

[N-38] 1500

y x 106

308

alpha-NP beta-NP

1000 500 0 50

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100

150 P (bar)

200

Solubility Data N

537

b -Naphthol (C10H8O; MW=144.17) P (bar) yx 106 330 132 420 152 580 318 99 140 132 480 152 640 328 111 220 132 510 152 730 Synonyms: 2-Naphthalenol; 2-Naphthol Source: Abaroudi, K.; Trabelsi, F.; Recasens, F. Fluid Phase Equil. (2000),169(2), 177-189.

900

y x 106

T (K) 308

[N-39]

106

308 K 318 K 328 K

600 300 0 80

100

120

140

P (bar)

b -Naphthol (C10H8O; MW=144.17)

[N-40] 1500 308.1 K 318.1 K 328.1 K

1000 y x 106

y x 106 T (K) P (bar) 308.1 100.5 249 140.0 433 180.0 509 220.5 547 260.0 610 300.0 654 318.1 100.5 148 140.0 470 180.0 649 220.5 772 260.0 847 300.0 964 328.1 100.5 116 140.0 441 180.0 692 220.5 925 260.0 1140 300.0 1230 Synonyms: 2-Naphthalenol; 2-Naphthol Source: Li, Q.; Zhang, Z.; Zhong, C.; Liu, Y.; Zhou, Q. Fluid Phase Equil. (2003), 207(1-2), 183-192.

160

500

0 50

CAT4240—CHAPTER 14—1/11/2006—17:04—SRIDHAR—XML MODEL C – pp. 513–568

150

250 P (bar)

350

538

Solubility in Supercritical Carbon Dioxide

b -Naphthol (C10H8O; MW=144.17) T (K) 308.15

P1)

(bar)

y1)

x

[N-41]

106

800

y x 106

98.6 224 124.3 400 145.7 464 400 170.0 520 200.0 552 235.7 572 0 1: Obtained by digitizing the graph in the original article. 50 Synonyms: 2-Naphthalenol; 2-Naphthol Source: Nakatani, T.; Ohgaki, K.; Katayama, T. Ind. Eng. Chem. Res. (1991), 30(6), 1362-1366.

150 P (bar)

250

b -Naphthol (C10H8O; MW=144.17)

2000

1500 y x 106

y x 106 T (K) P (bar) 308.25 102.8 110 118.5 202 143.7 446 200.5 528 279.7 638 362.0 720 318.25 102.8 100 118.5 235 143.7 477 200.5 681 279.7 742 362.0 950 328.05 105.2 80 111.5 110 120.0 189 145.7 448 201.0 798 281.0 1200 363.6 1390 343.05 105.2 58 111.5 97 120.0 136 145.7 414 201.0 960 281.0 1630 363.6 2000 Synonyms: 2-Naphthalenol; 2-Naphthol Source: Schmitt, W. J.; Reid, R. C. J. Chem. Eng. Data (1986), 31(2), 204-212.

[N-42]

308.2 K 318.2 K 328.2 K 343.2 K

1000

500

0 100

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200

300 P (bar)

400

Solubility Data N

539

b -Naphthol (C10H8O; MW=144.17) 1000 308 K 318 K 328 K

750 y x 106

y x 106 T (K) P (bar) 308 92.2 238 106.4 339 116.5 376 131.7 453 131.7 458 152.0 510 162.1 540 318 99.3 158 109.4 292 119.6 395 131.7 480 141.9 558 152.0 647 328 102.3 86 111.5 161 119.6 282 131.7 491 152.0 686 172.3 898 Synonyms: 2-Naphthalenol; 2-Naphthol Source: Tan, C. S.; Weng, J. Y. Fluid Phase Equil. (1987), 34(1), 37-47.

[N-43]

500

250

0 50

100

150

b -Naphthol (C10H8O; MW=144.17)

[N-44]

Methanol1) y x 106 (mol%) 4000 308.15 100 0.0 277 120 0.0 372 150 0.0 437 3000 200 0.0 557 250 0.0 661 250 0.0 635 2000 678 300 0.0 754 350 0.0 726 350 0.0 1000 1850 120 3.5 150 3.5 2150 0 200 3.5 2640 250 3.5 2860 0 300 3.5 2840 350 3.5 3080 1: Cosolvent in CO2. Synonyms: 2-Naphthalenol; 2-Naphthol Source: Dobbs, J. M.; Wong, J. M.; Lahiere, R. J.; Johnston, K. P. Ind. Eng. Chem. Res. (1987), 26(1), 56-65. P (bar)

Pure CO2 w/ MeOH

y x 106

T (K)

200

P (bar)

100

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200 P (bar)

300

400

540

Solubility in Supercritical Carbon Dioxide

b -Naphthol (C10H8O; MW=144.17)

318.1

328.1

308.1

318.1

328.1

308.1

(mol%) Acetone 101 3.6 140 3.6 180 3.6 221 3.6 260 3.6 300 3.6 101 3.6 140 3.6 180 3.6 221 3.6 260 3.6 300 3.6 101 3.6 140 3.6 180 3.6 221 3.6 260 3.6 300 3.6 Cyclohexane 101 3.6 140 3.6 180 3.6 221 3.6 260 3.6 300 3.6 101 3.6 140 3.6 180 3.6 221 3.6 260 3.6 300 3.6 101 3.6 140 3.6 180 3.6 221 3.6 260 3.6 300 3.6 101 140 180 221 260 300

Ethanol 3.6 3.6 3.6 3.6 3.6 3.6

y x 106 483 585 635 706 816 916 478 766 977 1100 1260 1500 379 1070 1500 1870 2230 1900 733 884 974 1060 1140 1240 580 851 1070 1330 1380 1550 313 893 220 1460 1780 1890 1820 2170 2360 2530 2680 2770

308.1 K 318.1 K 328.1 K

2000 y x 106

308.1

P (bar)

[N-45]

1000

Acetone 0 50

150

250

350

P (bar)

2000 308.1 K 318.1 K 328.1 K

y x 106

T (K)

Cosolvent1)

1000

Cyclohexane 0 50

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150

250 P (bar)

350

Solubility Data N

318.1

3000

y x 106

101 3.6 1150 140 3.6 2060 180 3.6 2360 221 3.6 2570 260 3.6 2750 300 3.6 3020 328.1 101 3.6 553 140 3.6 1490 180 3.6 2160 221 3.6 2430 260 3.6 2930 300 3.6 3270 1: Cosolvent in CO2. Synonyms: 2-Naphthalenol; 2-Naphthol Source: Li, Q.; Zhang, Z.; Zhong, C.; Liu, Y.; Zhou, Q. Fluid Phase Equil. (2003), 207(1-2), 183-192.

541

2000

308.1 K 318.1 K 328.1 K

1000

Ethanol 0 50

150

250 P (bar)

b -Naphthol (C10H8O; MW=144.17)

[N-46]

Methanol1) y x 106 30000 (mol%) 308.15 120 7.0 5080 200 7.0 7200 20000 250 7.0 7240 300 7.0 7170 350 7.0 6730 10000 200 9.0 11800 250 9.0 14400 250 9.0 15500 0 300 9.0 21100 100 350 9.0 24800 350 9.0 26200 1: Cosolvent in CO2. Synonyms: 2-Naphthalenol; 2-Naphthol Source: Dobbs, J. M.; Johnston, K. P. Ind. Eng. Chem. Res. (1987), 26(7), 1476-1482. P (bar)

MeOH 7.0% MeOH 9.0%

y x 106

T (K)

350

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200 P (bar)

300

400

542

Solubility in Supercritical Carbon Dioxide

b -Naphthol (C10H8O; MW=144.17) P (bar)

y x 106 (mol %) 313 88.5 0 57 95.6 0 120 122.7 0 310 180.7 0 539 85.2 5.14 1500 92.8 2.25 838 124.1 1.00 592 1: Cosolvent in CO2. Synonyms: 2-Naphthalenol; 2-Naphthol Source: Ngo, T. T.; Bush, D.; Eckert, C. A.; Liotta, C. L. AIChE J. (2001), 47(11), 2566-2572.

1600

y x 106

T (K)

[N-47]

Methanol1)

MeOH 0.00% MeOH 5.14% MeOH 2.25% MeOH 1.00%

800

0 50

100

150

b -Naphthol (C10H8O; MW=144.17)

368

P (bar) 150 200 200 150 200 200 150 200 200

Toluene1) (wt%) 0 0 0 6 6 6 10 10 10

[N-48]

y × 106 810 990 1220 2110 2120 2820 1980 2350 2880

1: Cosolvent in CO2. Synonyms: 2-Naphthalenol; 2-Naphthol Calloud-Gabriel, B.; Recasens, F. Ind. Eng. Chem. Res. (1999), 38(9), 35053518.

4000

y x 106

T (K)

200

P (bar)

Tol 0 wt% Tol 6 wt% Tol 10 wt%

2000

0 130

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170 P (bar)

210

Solubility Data N

543

b -Naphthol (1) + Anthracene (2) Mixture1) T (K)

P (bar)

308.15

120 150 200 200 300 350

Cosolvent (mol%)

y1 x 106

[N-49]

y2 x 106

3000

0.0 405 56 0.0 494 70 0.0 591 72 2000 0.0 613 79 0.0 744 84 0.0 776 89 Methanol 1000 120 3.5 1810 69 150 3.5 2230 80 200 3.5 2480 93 0 300 3.5 2890 99 100 350 3.5 2990 108 1: The solubility was measured from a mixture of solids 1 and 2 of 50:50 wt%. Source: Dobbs, J. M.; Johnston, K. P. Ind. Eng. Chem. Res. (1987), 26(7), 1476-1482.

y x 106

NP, CO2 NP, MeOH AN, CO2 AN, MeOH

200 300 P (bar)

b -Naphthol (1) + Phenanthrene (2) Mixture T (K)

P (bar)

y1 x

106

y2 x

106

3000 y x 106

139 406 1110 204 596 1540 271 722 1810 344 772 2020 318.15 136 399 962 204 738 1710 274 1160 2450 339 1320 2760 323.15 136 384 926 204 866 1960 274 1170 2660 341 1310 3030 328.15 136 367 909 204 946 2140 272 1350 3010 1440 3130 341 Source: Lemert, R. M.; Johnston, K. P. Fluid Phase Equil. (1990), 59(1), 31-55.

[N-50] 4000

308.15

400

2-Ntol 308 K 2-Ntol 318 K 2-Ntol 328 K Phen 308 K Phen 318 K Phen 328 K

2000

1000

0 100

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200 P (bar)

300

544

Solubility in Supercritical Carbon Dioxide

b -Naphthol (1) + Phenanthrene (2) Mixture P (bar)

9000

2-Ntol, 2.0% 2-Ntol, 3.8% 2-Ntol, 5.0% Phen, 2.0% Phen, 3.8% Phen, 5.0%

6000

y x 106

y1 x 106 y2 x 106 (mol%) 308.15 141 2.0 1520 1540 209 2.0 1570 1890 278 2.0 2030 2360 346 2.0 2500 2510 313.15 140 2.0 1290 1530 209 2.0 1890 2150 277 2.0 2340 2720 346 2.0 2920 3000 318.15 141 2.0 1260 1520 174 2.0 1700 1840 210 2.0 2050 2330 2740 2860 178 2.0 308.15 141 3.8 2000 1560 210 3.8 3510 1900 277 3.8 3860 2170 313.15 140 3.8 2780 1820 209 3.8 3520 2320 278 3.8 4430 2360 345 3.8 4900 2650 318.15 141 3.8 1880 1590 175 3.8 2410 2310 209 3.8 4070 2780 278 3.8 5230 3080 6980 4260 345 3.8 308.15 138 5.0 2710 1700 205 5.0 4460 2350 272 5.0 6310 2950 307 5.0 6700 3120 313.15 206 5.0 4170 2590 8420 4140 273 5.0 308.15 140 6.0 5340 2620 210 6.0 5150 2720 277 6.0 9330 3480 12400 4130 345 6.0 1: Cosolvent in CO2 on a solute-free basis. Source: Lemert, R. M.; Johnston, K. P. Fluid Phase Equil. (1990), 59(1), 31-55.

y x 106

T (K)

[N-51]

Methanol1)

308.15 K

3000

0 100

200

300

P (bar) 8000 6000

2-Ntol, 308 K 2-Ntol, 313 K 2-Ntol, 318 K Phen, 308 K Phen, 313 K Phen, 318 K

4000

2000 MeOH = 3.8%

0 100

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200 P (bar)

300

Solubility Data N

545

1,4-Naphthoquinone (C10H6O2; MW=158.15)

[N-52]

106

15000

318.2 K 328.2 K 343.2 K

10000 y x 106

yx T (K) P (bar) 318.15 101.0 932 115.8 1550 145.0 2620 200.5 4200 274.5 5760 363.0 6970 328.15 100.9 240 116.0 720 145.0 2120 200.5 4590 275.0 6960 364.0 8880 343.15 100.8 180 116.0 370 145.0 1670 200.5 5340 275.0 9920 364.0 13500 Synonyms: 1,4-Naphthalenedione; p-Naphthoquinone Source: Schmitt, W. J.; Reid, R. C. J. Chem. Eng. Data (1986), 31(2), 204-212.

5000

0 100

200

300 P (bar)

1,4-Naphthoquinone (C10H6O2; MW=158.15)

308.15

308.15

79.5 79.7 80.3 80.5 82.2 83.4 86.8 89.8 76.6 77.5 78.2 78.9 79.8 80.2 80.7 81.3 81.9 83.0 84.0 86.0 90.0

Cosolvent2) (mol%) 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 Acetone 0.5 0.5 0.5 0.5 0.5 0.5 0.5 0.5 0.5 0.5 0.5 0.5 0.5

[N-53]

y x 106 173 193 266 306 661 872 1310 1680 564 607 679 776 910 985 1180 1310 1470 1600 1740 1860 2090

8000

6000

y x 106

T (K) P1) (bar)

400

Pure CO2 w/Acetone 0.5% w/Acetone 1.1% w/CHClF2 1.1%

4000

2000

0 70

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80

90 P (bar)

100

546

Solubility in Supercritical Carbon Dioxide

308.15

80.4 81.1 82.9 84.5 85.9 88.3 90.7 92.5 94.2

1.1 1.1 1.1 1.1 1.1 1.1 1.1 1.1 1.1

4601 5150 5992 6222 6581 6740 7209 7578 7602

CHClF2 78.9 1.1 516 79.3 1.1 566 80.0 1.1 676 80.6 1.1 824 81.1 1.1 978 82.0 1.1 1230 84.5 1.1 1810 86.1 1.1 2060 87.9 1.1 2180 1: Pressure was calculated from density and temperature data in the source table. 2: Cosolvent in CO2. Synonyms: 1,4-Naphthalenedione; p-Naphthoquinone Source: Zhang, X.; Han, B.; Hou, Z.; Zhang, J.; Liu, Z.; Jiang, T.; He, J.; Li, H. Chem. Euro. J. (2002), 8(22), 5107-5111. 308.15

1,4-Naphthoquinone (C10H6O2; MW=158.15) T (K)

P (bar)

Methanol1) (mol %)

4000

y x 106

84.6 0 16 3000 0 85.3 30 0 88.3 123 0 90.0 187 2000 0 95.2 547 0 97.6 761 1000 0 1530 123.0 89.0 2.37 1980 100.7 1.04 1700 0 122.2 1.79 2990 70 1 : Cosolvent in CO2. Synonyms: 1,4-Naphthalenedione; p - Naphthoquinone Source: Ngo, T. T.; Bush, D.; Eckert, C. A.; Liotta, C. L. AIChE J. (2001), 47(11), 2566-2572.

y x 106

313

[N-54] 0 mol % 1.04 mol % 1.79 mol % 2.37 mol %

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100 P (bar)

130

Solubility Data N

547

Naproxen (C14H14O3; MW=230.26) T (K)

P (bar)

S (g/L)

yx

[N-55]

106

308

200

150 y x 106

122 0.05 10 152 0.08 20 182 0.09 20 213 0.09 20 243 0.11 20 274 0.13 30 304 0.15 30 355 0.19 40 318 122 0.06 20 152 0.08 20 182 0.10 20 213 0.12 30 243 0.15 30 274 0.17 40 304 0.19 40 355 0.23 50 328 122 0.03 10 152 0.06 20 182 0.09 20 213 0.12 30 243 0.17 40 274 0.20 50 304 0.24 50 355 0.25 80 338 122 0.03 20 152 0.06 20 182 0.10 30 213 0.15 40 243 0.23 60 274 0.28 70 304 0.34 80 355 0.51 110 348 122 0.02 10 152 0.04 20 182 0.09 30 213 0.16 50 243 0.25 70 274 0.40 100 304 0.52 130 355 0.84 200 Synonyms: (S)-2-(6-Methoxy-2naphthyl)propionic acid; (+)-Naproxen; (S )-(+)-Naproxen Source: Garmroodi, A.; Hassan, J.; Yamini, Y. J. Chem. Eng. Data (2004), 49(3), 709-712.

308 K 318 K 328 K 338 K 348 K

100

50

0 100

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200

300 P (bar)

400

548

Solubility in Supercritical Carbon Dioxide

Naproxen (C14H14O3; MW=230.26) yx

2.0 8.3 12.9 17.2 20.8 24.3 1.9 4.3 12.0 17.7 23.2 29.1 7.0 10.8 15.6 23.3 27.1 31.8

40 313.1 K 323.1 K 333.1 K

30 y x 106

T (K) P (bar) 313.1 89.6 110.3 131.0 151.7 172.4 193.1 323.1 100.0 110.3 131.0 144.8 172.4 193.1 333.1 124.1 137.9 151.7 165.5 179.3 193.1

[N-56]

106

20

10

0 50

100

150

200

P (bar)

Synonyms: (S )-2-(6-Methoxy-2naphthyl)propionic acid; (+)-Naproxen; (S )-(+)-Naproxen Source: Ting, S. S. T.; Tomasko, D. L.; Foster, N. R.; Macnaughton, S. J. Ind. Eng. Chem. Res. (1993), 32(7), 1471-1481.

Naproxen (C14H14O3; MW=230.26)

318.1

323.1

333.1

P (bar) 89.6 96.5 110.3 124.1 137.9 151.7 165.5 179.3 110.3 124.1 137.9 151.7 165.5 179.3 110.3 124.1 137.9 151.7 165.5

Acetone (mol %)

3.50 3.50 3.50 3.50 3.50 3.50 3.50 3.50 3.50 3.50 3.50 3.50 3.50 3.50 1.75 1.75 1.75 1.75 1.75

y x 106 24.5 31.7 46.6 52.2 60.5 67.9 71.8 76.3 32.5 47.8 58.4 70.5 79.1 89.8 6.0 14.9 26.7 39.1 50.5

[N-57] 120 318.1 K 323.1 K 333.1 K

80

3.5 mol% Acetone

y x 106

T (K)

1)

40

0 50

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100

150 P (bar)

200

Solubility Data N

549

y x 106

179.3 1.75 60.9 193.1 1.75 57.5 110.3 3.50 20.3 124.1 3.50 34.2 137.9 3.50 53.7 151.7 3.50 69.6 165.5 3.50 85.5 179.3 3.50 108.0 110.3 5.25 45.5 124.1 5.25 78.8 137.9 5.25 106.8 151.7 5.25 131.4 165.5 5.25 150.7 179.3 5.25 169.7 1: Cosolvent in CO2 on a solute-free basis. Synonyms: (S )-2-(6-Methoxy-2-naphthyl)propionic acid; (+)-Naproxen; (S)-(+)-Naproxen Source: Ting, S. S. T.; Tomasko, D. L.; Foster, N. R.; Macnaughton, S. J. Ind. Eng. Chem. Res. (1993), 32(7), 1471-1481.

200 110.3 bar 124.1 bar 137.9 bar 151.7 bar 165.5 bar 179.3 bar

150 100

333.1 K

50 0 0

2

4

Acetone (mol%)

Naproxen (C14H14O3; MW=230.26) P (bar)

333.1

110.3 124.1 137.9 151.7 165.5 179.3 110.3 124.1 137.9 151.7 165.5 179.3 110.3 124.1 137.9 151.7 165.5 179.3

1.75 1.75 1.75 1.75 1.75 1.75 3.50 3.50 3.50 3.50 3.50 3.50 5.25 5.25 5.25 5.25 5.25 5.25

y x 106 6.4 13.2 23.6 32.6 41.5 52.6 21.0 34.3 52.7 65.5 71.8 97.5 53.2 73.8 96.4 116.0 131.1 143.3

[N-58]

150

1.75 mol% 3.50 mol% 5.25 mol%

100 y x 106

T (K)

Ethyl acetate1) (mol %)

6

50

0 100

1: Cosolvent in CO2 on a solute-free basis. Synonyms: (S )-2-(6-Methoxy-2-naphthyl)propionic acid; (+)-Naproxen; (S )-(+)-Naproxen Source: Ting, S. S. T.; Tomasko, D. L.; Foster, N. R.; Macnaughton, S. J. Ind. Eng. Chem. Res. (1993), 32(7), 1471-1481.

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150 P (bar)

200

550

Solubility in Supercritical Carbon Dioxide

Naproxen (C14H14O3; MW=230.26) T (K)

P (bar)

Ethanol1) (mol %)

[N-59]

y x 106

600

3.50 81.3 110.3 114.2 124.1 3.50 142.1 137.9 3.50 3.50 151.7 152.4 400 3.50 168.2 165.5 191.8 179.3 3.50 333.1 110.3 1.75 12.6 124.1 1.75 26.9 200 137.9 1.75 44.2 151.7 1.75 62.6 165.5 1.75 80.9 179.3 1.75 95.5 110.3 3.50 47.6 0 124.1 3.50 96.2 100 137.9 3.50 141.7 151.7 3.50 181.6 165.5 3.50 221.9 179.3 3.50 256.1 110.3 5.25 127.8 124.1 5.25 214.7 137.9 5.25 298.7 151.7 5.25 364.3 165.5 5.25 425.8 179.3 5.25 477.8 1: Cosolvent in CO2 on a solute-free basis. Synonyms: (S )-2-(6-Methoxy-2-naphthyl)propionic acid; (+)-Naproxen; (S)-(+)-Naproxen Source: Ting, S. S. T.; Tomasko, D. L.; Foster, N. R.; Macnaughton, S. J. Ind. Eng. Chem. Res. (1993), 32(7), 1471-1481.

323 K, 3.50% 333 K, 1.75% 333 K, 3.50% 333 K, 5.25%

y x 106

323.1

Naproxen (C14H14O3; MW=230.26) T (K) 323.1

333.1

P (bar) 110.3 124.1 137.9 151.7 165.5 179.3 193.1 110.3 124.1 137.9

Methanol1)

(mol %) 3.50 3.50 3.50 3.50 3.50 3.50 3.50 1.75 1.75 1.75

y x 106 86.9 113.7 147.5 163.1 195.2 224.6 240.5 8.7 19.5 35.3

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150

200

P (bar)

[N-60]

Solubility Data N

551

323 K, 3.50% 333 K, 1.75% 333 K, 3.50% 333 K, 5.25%

y x 106

151.7 1.75 56.4 500 165.5 1.75 77.6 179.3 1.75 95.3 110.3 3.50 32.9 400 124.1 3.50 72.7 137.9 3.50 122.2 151.7 3.50 165.4 300 165.5 3.50 203.9 179.3 3.50 235.6 193.1 3.50 285.4 200 110.3 5.25 81.1 124.1 5.25 156.3 137.9 5.25 229.9 100 151.7 5.25 302.5 165.5 5.25 359.0 179.3 5.25 416.1 0 100 1: Cosolvent in CO2 on a solute-free basis. Synonyms: (S )-2-(6-Methoxy-2-naphthyl)propionic acid; (+)-Naproxen; (S )-(+)-Naproxen Source: Ting, S. S. T.; Tomasko, D. L.; Foster, N. R.; Macnaughton, S. J. Ind. Eng. Chem. Res. (1993), 32(7), 1471-1481.

150 P (bar)

[N-61]

Naproxen (C14H14O3; MW=230.26) T (K)

P (bar)

1-Propanol1) (mol%)

200

y x 106

800

110.3 1.75 22.3 124.1 1.75 38.6 600 137.9 1.75 58.8 151.7 1.75 73.5 179.3 1.75 112.0 110.3 3.50 86.6 400 124.1 3.50 143.4 137.9 3.50 193.0 151.7 3.50 231.8 200 179.3 3.50 315.8 110.3 5.25 251.7 124.1 5.25 346.5 0 137.9 5.25 423.4 100 151.7 5.25 504.0 179.3 5.25 618.2 1: Cosolvent in CO2 on a solute-free basis. Synonyms: (S )-2-(6-Methoxy-2-naphthyl)propionic acid; (+)-Naproxen; (S )-(+)-Naproxen Source: Ting, S. S. T.; Tomasko, D. L.; Foster, N. R.; Macnaughton, S. J. Ind. Eng. Chem. Res. (1993), 32(7), 1471-1481.

1.75 mol% 3.50 mol% 5.25 mol%

y x 106

333.1

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150 P (bar)

200

552

Solubility in Supercritical Carbon Dioxide

Naproxen (C14H14O3; MW=230.26)

323.1

333.1

P (bar) 110.3 124.1 137.9 151.7 166.5 179.3 110.3 124.1 137.9 151.7 166.5 179.3 110.3 124.1 137.9 151.7 179.3

(mol%) 3.50 3.50 3.50 3.50 3.50 3.50 1.75 1.75 1.75 1.75 1.75 1.75 3.50 3.50 3.50 3.50 3.50

yx

[N-62]

106

95.4 138.0 158.5 183.1 216.4 220.0 13.7 32.0 53.2 72.2 89.1 108.4 70.1 118.0 168.3 216.7 281.1

600

323 K, 3.50% 333 K, 1.75% 333 K, 3.50% 333 K, 5.25%

400 y x 106

T (K)

2-Propanol1)

200

0 100

110.3 5.25 197.1 124.1 5.25 280.9 137.9 5.25 363.3 151.7 5.25 438.2 179.3 5.25 566.0 1: Cosolvent in CO2 on a solute-free basis.

150

200

P (bar)

Synonyms: (S)-2-(6-Methoxy-2-naphthyl)propionic acid; (+)-Naproxen; (S)-(+)-Naproxen Source: Ting, S. S. T.; Tomasko, D. L.; Foster, N. R.; Macnaughton, S. J. Ind. Eng. Chem. Res. (1993), 32(7), 1471-1481.

Narasin sodium salt (C43H71NaO11; FW= 787.02)

343.15

353.15

P (bar) 195 206 264 274 332 401 175 241 314 405 141 217 276 364

yx 0 0 0 0 0 0 0 0 0 0 0 0 0 0

106 15.9 19.8 23.6 23.9 36.2 55.3 22.7 29.1 46.2 64.4 18.2 18.7 32.4 74.3

[N-63]

360 333 K, CO2 343 K, CO2 353 K, CO2 333 K, Sat'd H2O

240 y x 106

T (K) 333.15

Water1)

120

0 100

200

300 P (bar)

CAT4240—CHAPTER 14—1/11/2006—17:04—SRIDHAR—XML MODEL C – pp. 513–568

400

Solubility Data N

553

333.15

181 Saturated 26.3 184 Saturated 38.2 243 Saturated 132.0 311 Saturated 244.0 401 Saturated 319.0 1: Cosolvent in CO2. Synonym: (4 S)-4-Methylsalinomycin monosodium salt Source: Maxwell, R.; Hampson, J.; CygnarowiczProvost, M. J. Supercrit. Fluids (1992), 5(1), 31-37.

Nickel complex1) (C22H22N4Ni; FW=401.15) P (bar)

Ethanol2) (wt%)

y x 106

333

161 252 342

10 10 10

0.67 2.26 3.05

4 y x 106

T (K)

[N-64]

1: The exact name of this compound is (5,7,12,14-Tetramethyl-2,3:9,10-dibenzo [b,i ][1,4,8,11]tetraazacyclotetradecine) nickel(II). 2 : Cosolvent in CO2. Source: Burford, M. D.; Clifford, A. A.; Bartle, K. D.; Cowey, C. M.; Smart, N. G. J. Chromatogr., A (1996), 738(2), 241-252.

2 0 100

200

300

Nickel complex1) (C22H22N4Ni; FW=401.15) P (bar)

313.15

161.1 252.6 342.3 161.1 252.6 342.3 161.1 252.6 342.3 161.1 252.6 342.3

323.15

333.15

343.15

Methanol2) (vol%) 10 10 10 10 10 10 10 10 10 10 10 10

[N-65] 80

y3) x 106 13.2 19.3 23.6 13.8 24.0 27.4 12.5 30.9 36.5 13.1 46.5 70.3

60 y x 106

T (K)

400

P (bar)

313.15 K 323.15 K 333.15 K 343.15 K

40 20 0 100

1: The exact name of this compound is (5,7,12,14-Tetramethyl-2,3:9,10-dibenzo [b,i ][1,4,8,11]tetraazacyclotetradecine) nickel(II). 2 : Cosolvent in CO2. 3: The solubility was measured directly by an SFE system. Source: Cowey, C. M.; Bartle, K. D.; Burford, M. D.; Clifford, A. A.; Zhu, S.; Smart, N. G.; Tinker, N. D. J. Chem. Eng. Data (1995), 40(6), 1217-1221.

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200

300 P (bar)

400

554

Solubility in Supercritical Carbon Dioxide

Nickel complex1) (C22H22N4Ni; FW=401.15) T (K)

P (bar)

Methanol2) (vol%)

[N-66]

y3) x 106

313.15

313.15 K 323.15 K 333.15 K 343.15 K

y x 106

161.1 10 12.0 191.6 10 14.2 221.9 10 16.4 252.6 10 18.5 283.3 10 20.3 80 314.0 10 21.7 342.3 10 22.1 372.3 10 21.3 323.15 161.1 10 14.4 60 191.6 10 18.2 221.9 10 22.3 252.6 10 26.1 283.3 10 29.7 40 314.0 10 30.0 342.3 10 30.2 372.3 10 29.1 333.15 161.1 10 14.6 20 191.6 10 20.6 221.9 10 26.6 252.6 10 32.8 0 283.3 10 38.7 314.0 10 44.3 100 342.3 10 44.0 372.3 10 44.0 343.15 161.1 10 12.6 191.6 10 20.1 221.9 10 28.1 252.6 10 36.3 283.3 10 45.2 314.0 10 53.9 342.3 10 62.5 372.3 10 66.5 1: The exact name is (5,7,12,14-tetramethyl-2,3:9,10-dibenzo[b,i][1,4,8,11]tetraazacyclotetradecine)nickel(II). 2 : Cosolvent in CO2. 3 : The solubility was measured by supercritical fluid chromatography. (Compare with the SFE method above). Source: Cowey, C. M.; Bartle, K. D.; Burford, M. D.; Clifford, A. A.; Zhu, S.; Smart, N. G.; Tinker, N. D. J. Chem. Eng. Data (1995), 40(6), 1217-1221.

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200

300 P (bar)

400

Solubility Data N

555

Nicotinic acid (C6H5NO2; MW=123.11)

[N-67]

106

yx P (bar) 100 1.22 120 1.36 140 1.63 160 1.74 180 1.95 200 2.00 328.15 100 0.93 120 1.83 140 1.73 160 3.18 180 3.88 200 4.46 348.15 100 1.22 120 1.63 160 4.33 180 6.79 200 7.58 Synonyms: 3-Carboxypyridine; 3-Pyridinecarboxylic acid Source: Jouyban, A.; Rehman, M.; Shekunov, B. Y.; Chan, H.-K.; Clark, B. J.; York, P. J. Pharmac. Sci. (2002), 91(5), 1287-1295.

9 308.15 K 328.15 K 348.15 K

6

y x 106

T (K) 308.15

3

0 50

100

150 P (bar)

Nicotinic acid (C6H5NO2; MW=123.11)

328

[N-68] 6

P1) (bar) y1) x 106 100 120 140 160 180 200 100 120 140 160 180 200

1.40 1.50 1.75 1.75 2.00 2.20 1.00 2.10 3.05 3.82 4.25 5.15

308 K 328 K

4 y x 106

T (K) 308

200

2

0 50

100

1: Obtained by digitizing the graph in the original article. Synonyms: 3-Carboxypyridine; 3-Pyridinecarboxylic acid Source: Rehman, M.; Shekunov, B. Y.; York, P.; Colthorpe, P. J. Pharm. Sci. (2001), 90(10), 1570-1582.

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150 P (bar)

200

556

Solubility in Supercritical Carbon Dioxide

Nicotinic acid (C6H5NO2; MW=123.11) T (K) P1) (bar)

Methanol2) (mol %)

[N-69]

y1) x 106

80 2 19 100 2 14 120 2 15 140 2 16 160 2 17 180 2 19 200 2 20 318 80 2 6 100 2 10 120 2 13 140 2 15 45 160 2 18 180 2 20 200 2 22 328 80 2 0 100 2 6 30 120 2 15 140 2 16 160 2 22 180 2 26 200 2 27 15 338 80 2 0 100 2 6 120 2 13 140 2 19 160 2 25 0 180 2 29 50 200 2 33 348 80 2 2 100 2 6 120 2 11 140 2 20 160 2 29 180 2 35 200 2 40 363 80 2 6 100 2 10 120 2 15 140 2 25 160 2 33 180 2 41 200 2 42 1: Obtained by digitizing the graph in the original article. 2 : Cosolvent in CO2. Synonyms: 3-Carboxypyridine; 3-Pyridinecarboxylic acid Source: Rehman, M.; Shekunov, B. Y.; York, P.; Colthorpe, P. J. Pharm. Sci. (2001), 90(10), 1570-1582.

y x 106

308

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308 K 318 K 328 K 338 K 348 K 363 K

100

150 P (bar)

200

Solubility Data N

557

Nicotinic acid (C6H5NO2; MW=123.11) T (K) P1) (bar)

[N-70]

Methanol2)

y x 106

y1) x 106 (mol %) 308 200 0.3 0 120 0.9 2 1.2 8 1.5 10 2.0 13 80 2.9 30 3.9 42 201 4.9 58 348 120 1.2 5 1.3 5 40 1.9 7 2.2 7 2.9 9 3.8 19 4.7 28 0 5.7 40 0 6.3 51 121 7.2 69 122 9.0 110 1: Obtained by digitizing the graph in the original article. 2: Cosolvent in CO2. Synonyms: 3-Carboxypyridine; 3-Pyridinecarboxylic acid Source: Rehman, M.; Shekunov, B. Y.; York, P.; Colthorpe, P. J. Pharm. Sci. (2001), 90(10), 1570-1582.

308 K, 200 bar 308 K, 201 bar 348 K, 120 bar 348 K, 121 bar 348 K, 122 bar

Nicotinic acid (C6H5NO2; MW=123.11)

200

308 318 328 338 348 363 308 318 328 338 348 363

2 2 2 2 2 2 2 2 2 2 2 2

y1)x 106 15 10 6 6 6 10 21 23 27 33 40 42

50

yx

100

(mol %)

[N-71]

106

T (K) P1) (bar)

Methanol2)

10

5 Methanol (mol%)

100 bar 200 bar

25

0 300

320

1: Obtained by digitizing the graph in the original article. 2: Cosolvent in CO2. Synonyms: 3-Carboxypyridine; 3-Pyridinecarboxylic acid Source: Rehman, M.; Shekunov, B. Y.; York, P.; Colthorpe, P. J. Pharm. Sci. (2001), 90(10), 1570-1582.

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340 T (K)

360

558

Solubility in Supercritical Carbon Dioxide

Nifedipine (C17H18N2O6; MW=346.33)

[N-72]

333.15 K 353.15 K 373.15 K

y x 106

y x 106 T (K) P (bar) 333.15 135 5.08 146 8.08 80 210 15.06 217 17.61 247 20.75 60 255 23.24 290 25.91 296 30.59 353.15 126 1.35 40 140 3.55 168 6.11 187 10.14 20 212 18.11 215 16.78 250 25.32 255 24.42 0 280 36.16 100 283 38.03 373.15 126 1.43 140 3.79 161 3.49 170 4.9 191 11.04 211 18.46 224 20.57 242 31.05 266 46.53 289 60.22 296 70.87 Synonym: 4-(2-Nitrophenyl)-2,6-dimethyl-3,5dicarbomethoxy-1,4-dihydropyridine Source: Knez, Z.; Skerget, M.; Sencar-Bozic, P.; Rizner, A. J. Chem. Eng. Data (1995), 40(1), 216-220.

200

300

P (bar)

Nimesulide (C13H12N2O5S; MW=308.31)

333.1

P (bar) 130 160 190 220 130 160 190 220

yx

18.9 31.8 51.1 74.2 8.5 38.0 70.8 98.5

120

y x 106

T (K) 313.1

[N-73]

106

Synonym: 4-Nitro-2-phenoxymethanesulfonanilide Source: Macnaughton, S. J.; Kikic, I.; Foster, N. R.; Alessi, P.; Cortesi, A.; Colombo, I. J. Chem. Eng. Data (1996), 41(5), 1083-1086.

80

313.1 K 333.1 K

40 0 100

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150

200 P (bar)

250

Solubility Data N

559

Nimodipine (C21H26N2O7; MW=418.44) T (K) 313

P (bar) S x106(g/L) 100 31.1 125 53.5 150 79.3 175 100.5 200 110.1 225 129.1 250 140.3 100 7.1 125 37.3 150 76.8 175 121.8 200 157.6 225 191.2 250 200.5 100 1.7 125 22.3 150 71.9 175 147.9 200 211.0 225 271.8 250 328.0

[N-74]

y x 106 313 K 323 K 333 K

y x 106

5.0 7.4 10.3 40 12.5 13.3 15.2 16.2 323 1.8 6.1 20 11.1 16.5 20.4 23.9 24.4 0 333 0.6 50 4.6 12.0 22.1 29.5 36.4 42.3 Synonym: 1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)3,5-pyridinedicarboxylic acid 2-methoxyethyl 1-methylethyl ester Source: Medina, I.; Bueno, J. L. J. Chem. Eng. Data (2001), 46(5), 1211-1214.

Nitrendipine (C18H20N2O6; MW=360.36) T (K) P (bar) 333.15 117 130 142 159 168 179 190 200 217 226 239 246 259 275 300 353.15 100 117 126 139

yx

106

5.66 6.86 13.41 16.93 18.55 21.90 23.25 23.67 25.24 28.15 30.77 35.17 36.42 43.09 49.03 1.34 2.91 2.37 4.40

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150

250

P (bar)

[N-75]

560

Solubility in Supercritical Carbon Dioxide

333.15 K 353.15 K 373.15 K

y x 106

150 7.00 120 162 9.60 173 15.45 186 20.78 206 27.69 214 32.36 80 230 36.89 242 42.45 281 56.40 290 66.66 300 70.63 40 373.15 121 2.69 136 7.82 142 11.63 174 21.73 192 26.48 0 205 34.21 50 218 43.16 227 46.41 241 59.95 261 69.95 283 89.70 300 105.86 Synonym: 1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)3,5-pyridinedicarboxylic acid ethyl methyl ester Source: Knez, Z.; Skerget, M.; Sencar-Bozic, P.; Rizner, A. J. Chem. Eng. Data (1995), 40(1), 216-220.

150

250 P (bar)

2-Nitroanisole (C7H7NO3; MW=153.14) T (K)

P (bar)

S (g/L)

yx

350

[N-76]

106

6000

80 1.31 1230 100 8.17 3700 125 11.88 4620 150 14.15 5170 4000 175 15.80 5530 200 17.12 5810 323 80 0.47 580 100 2.05 1390 125 5.42 2500 2000 150 7.24 2950 175 8.76 3330 200 9.78 3560 333 80 0.22 320 100 0.66 620 0 125 2.14 1250 50 150 3.63 1710 175 4.81 2030 200 5.75 2270 Synonym: 2-Methoxynitrobenzene Source: Medina, L.; Bueno, J. L. J. Chem. Eng. Data (2000), 45(2), 298-300.

y x 106

313

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313 K 323 K 333 K

150 P (bar)

250

Solubility Data N

561

9-Nitroanthracene (C14H9NO2; MW=223.23) T (K)

P (bar)

[N-77]

y x 106

122 35 152 46 182 51 213 53 243 53 274 58 304 60 334 62 355 62 318 122 30 152 45 182 63 213 70 243 80 274 88 304 92 334 99 355 100 328 122 33 152 52 182 75 213 96 243 110 274 122 304 140 334 145 355 149 338 122 40 152 54 182 92 213 122 243 148 274 170 304 200 334 208 355 222 348 122 28 152 52 182 97 213 148 243 192 274 235 304 268 334 304 355 320 Source: Yamini, Y.; Bahramifar, N.; Hassan, J. J. Chem. Eng. Data (2002), 47(2), 329-332.

y x 106

308

400

300

308 K 318 K 328 K 338 K 348 K

200

100

0 100

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200

300 P (bar)

400

562

Solubility in Supercritical Carbon Dioxide

9-Nitroanthracene (1) + 2-Methyl anthracene (2) Mixture1) 106

y1 x y2 x P (bar) 122 46 110 152 56 137 182 64 157 213 74 189 600 243 93 207 9-Nitroanthracene 274 89 242 308 K 304 92 266 318 K 334 96 318 328 K 355 115 357 400 338 K 318 122 55 101 348 K 152 68 133 182 91 188 213 98 214 243 116 262 200 274 123 332 304 131 377 334 139 438 355 147 538 328 122 24 54 0 152 73 131 100 200 300 182 105 200 P (bar) 213 124 253 243 166 348 274 211 419 304 206 450 1200 334 274 583 355 244 640 2-Methylanthracene 338 122 31 34 308 K 152 85 117 318 K 182 147 214 328 K 800 213 208 321 338 K 243 263 448 348 K 274 309 533 304 362 646 334 415 760 400 355 439 817 348 122 18 18 152 73 76 182 162 192 213 249 328 0 243 329 469 100 200 300 274 406 601 304 479 751 P (bar) 334 508 863 355 536 1057 1: Solubility was measured from an equimolar mixture of 1 and 2. Source: Yamini, Y.; Bahramifar, N.; Hassan, J. J. Chem. Eng. Data (2002), 47(2), 329-332.

y x 106

T (K) 308

[N-78]

106

y x 106

400

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400

Solubility Data N

563

2-Nitrodiphenylamine (C12H10N2O2; MW=214. 22) P (bar)

S (g/L)

x

106

313.15 160 1.97 507 333.15 263 4.07 1042 1: Calculated form S. Synonym: 2-Nitro-N-phenylaniline Source: Ashraf-Khorassani, M.; Taylor, L. T. J. Chem. Eng. Data (1999), 44(6), 1254-1258.

[N-79]

1200 y x 106

T (K)

y1)

600

313 K 333 K

0 100

200

300

P (bar)

m-Nitrophenol (C6H5NO3; MW=139.11)

318

328

338

P (bar) 121.6 162.1 202.6 243.2 283.7 324.2 364.8 405.3 445.8 486.4 121.6 162.1 202.6 243.2 283.7 324.2 364.8 405.3 445.8 486.4 121.6 162.1 202.6 243.2 283.7 324.2 364.8 405.3 445.8 486.4 121.6 162.1

S (g/L) 0.96 1.36 1.59 1.78 2.02 2.29 2.63 2.76 3.22 3.47 0.96 1.59 2.12 2.59 2.94 3.08 3.66 4.13 5.09 5.50 0.43 1.29 2.11 3.07 3.55 4.55 5.24 6.74 7.59 7.35 0.41 1.08

y x 106 394 517 579 627 691 768 865 895 1030 1090 454 657 823 960 1060 1080 1250 1380 1680 1790 259 594 879 1200 1340 1690 1860 2340 2590 2460 329 568

5000 308 K 318 K 328 K 338 K 348 K

4000

y x 106

T (K) 308

[N-80]

3000 2000 1000 0 0

CAT4240—CHAPTER 14—1/11/2006—17:05—SRIDHAR—XML MODEL C – pp. 513–568

200

400 P (bar)

600

564

Solubility in Supercritical Carbon Dioxide

202.6 1.87 850 243.2 2.94 1230 283.7 4.04 1600 324.2 5.95 2270 364.8 7.84 2900 405.3 9.11 3290 445.8 10.40 3670 486.4 11.45 3970 348 121.6 0.14 132 162.1 0.88 536 202.6 1.91 959 243.2 2.95 1330 283.7 4.65 1960 324.2 6.41 2570 364.8 8.44 3260 405.3 10.33 3880 445.8 12.15 4450 Synonym: 3-Nitrophenol Source: Shamsipur, M.; Fat'hi, M. R.; Yamini, Y.; Ghiasvand, A. R. J. Supercrit. Fluids (2002), 23(3), 225-231.

p-Nitrophenol (C6H5NO3; MW=139.11) 308

318

328

P (bar) 121.6 162.1 202.6 243.2 283.7 324.2 364.8 405.3 445.8 486.4 121.6 162.1 202.6 243.2 283.7 324.2 364.8 405.3 445.8 486.4 121.6 162.1 202.6 243.2 283.7 324.2 364.8

S (g/L) 0.54 0.73 0.91 1.09 1.33 1.50 1.69 1.80 1.87 2.09 0.46 0.81 0.94 1.29 1.66 1.94 2.08 2.38 2.69 2.76 0.27 0.66 1.09 1.49 1.95 2.25 2.63

yx

223 277 331 385 457 502 558 582 598 658 217 335 364 478 597 678 711 795 889 899 163 307 455 584 734 821 936

2000

308 K 318 K 328 K 338 K 348 K

1500 y x 106

T (K)

[N-81]

106

1000

500

0 0

CAT4240—CHAPTER 14—1/11/2006—17:05—SRIDHAR—XML MODEL C – pp. 513–568

200

400 P (bar)

600

Solubility Data N

565

405.3 2.86 994 445.8 3.41 1160 486.4 3.62 1210 338 121.6 0.14 110 162.1 0.56 296 202.6 1.10 502 243.2 1.68 703 283.7 2.23 886 324.2 2.83 1080 364.8 3.30 1220 405.3 3.83 1380 445.8 4.35 1540 486.4 4.90 1700 348 121.6 0.10 98 162.1 0.48 295 202.6 1.15 576 243.2 1.88 846 283.7 2.70 1140 324.2 3.36 1350 364.8 4.30 1660 405.3 4.69 1760 445.8 5.39 1970 Synonym: 4-Nitrophenol Source: Shamsipur, M.; Fat'hi, M. R.; Yamini, Y.; Ghiasvand, A. R. J. Supercrit. Fluids (2002), 23(3), 225-231.

3-Nitrotoluene (C7H7NO2; MW=137.14)

[N-82]

313 K 323 K 333 K

y x 106

y x 106 T (K) P (bar) 313 80 720 100 3370 6000 125 4580 150 4950 175 5590 200 5920 4000 323 80 310 100 930 125 2310 150 3060 2000 175 3470 200 3690 333 80 150 100 360 0 125 1070 150 1580 50 175 1910 200 2430 Synonym: 1-Methyl-3-nitrobenzene Source: Medina, I.; Bueno, J. L. Fluid Phase Equil. (2001), 187-188, 337-345.

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100

150 P (bar)

200

566

Solubility in Supercritical Carbon Dioxide

Nonacosane (C29H60; MW=408.79) y1)

[N-83]

106

308.2 K 318.2 K

y x 106

x T (K) P (bar) 450 308.2 100 12 120 80 140 150 300 160 200 180 250 200 310 240 360 150 318.2 100 27 120 45 140 54 0 160 64 180 73 50 200 79 240 98 1: The datum at 318.2 K and 100 bar (in italics) is the extrapolated value in the original article. Source: Chandler, K.; Pouillot, F. L. L.; Eckert, C. A. J. Chem. Eng. Data (1996), 41, 6-10.

150 P (bar)

Nonacosane (C29H60; MW=408.79)

[N-84]

106

100 y x 106

T (K) P (bar) yx 313 124 41 133 58 161 69 165 66 178 73 Source: Furuya, T.; Teja, A. S. J. Supercrit. Fluids (2004), 29(3), 231-236.

250

50 0 100

150

200

P (bar) Nonadecane (C19H40; MW=268.53) S (g/L) 4.6 10.1 16.5 27.7 38.0 53.2 61.1 71.4 88.0 102.8 122.7

x

[N-85]

106

1551 3048 4606 7055 9472 12680 14320 16450 19740 22650 26510

30000

y x 106

T (K) P (bar) 343 144.5 157.0 169.0 189.0 194.5 208.5 214.5 221.0 232.0 240.0 249.0

y1)

15000

0 100

1: Calculated from S. Source: Chartier, T.; Delhomme, E.; Baumard, J. F.; Marteau, P.; Subra, P.; Tufeu, R. Ind. Eng. Chem. Res. (1999), 38(5), 1904-1910.

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200 P (bar)

300

Solubility Data N

567

Nonadecane (C19H40; MW=268.53) 20000 310 K

y x 106

y x 106 T (K) P (bar) 310 111.0 4400 140.0 7480 204.0 18400 320 111.0 1750 140.0 4800 140.0 5890 204.0 8650 Source: Schmitt, W. J.; Reid, R. C. Chem. Eng. Comm. (1988), 64, 155-176.

[N-86]

320 K

10000

0 100

150

200

P (bar)

[N-87]

Nonadecanenitrile (C19H37N; MW=279.50) 20000 y x 106

T (K) P (bar) y1) x 106 320 110.5 1260 140.0 5080 203.0 17000 1: These values may need corrections as the incorrect chemical formula [(C19H39)CN] and molecular weight [293.54] were used in the source table. Synonyms: Octadecyl cyanide; 1Cyanooctadecane Source: Schmitt, W. J.; Reid, R. C. Chem. Eng. Comm. (1988), 64, 155-176.

10000 0 100

150 P (bar)

2-Nonadecanone (C19H38O; MW=282.50)

[N-88] 10000 y x 106

6

y x 10 T (K) P (bar) 320 111.0 2570 143.0 9380 Synonym: Heptadecyl methyl ketone Source: Schmitt, W. J.; Reid, R. C. Chem. Eng. Comm. (1988), 64, 155-176.

200

5000 0 100

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125 P (bar)

150

568

Solubility in Supercritical Carbon Dioxide

1-Nonanol (C9H20O; MW=144.25)

[N-89]

y x 106

y x 106 T (K) P (bar) 150000 323.15 94.5 6564 104.6 9435 104.6 9435 100000 123.6 16630 147.3 28870 147.3 29300 50000 159.0 38420 173.7 60000 184.7 76440 0 202.8 86770 50 221.7 122000 Synonym: Nonyl alcohol Source: Artal, M.; Pauchon, V.; Embid, J. M.; Jose, J. J. Chem. Eng. Data (1998), 43(6), 983-985.

100

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150 P (bar)

200

250

15

Solubility Data O [O-1]

Octacosane (C28H58; MW=394.76) 600 308.2 K 318.2 K

400

y x 106

T (K) P (bar) y1) x 106 308.2 100 38 120 62 140 73 160 87 180 100 200 110 240 130 318.2 100 19 120 110 140 200 160 270 180 340 200 410 240 470 1: The datum at 318.2 K and 100 bar is the extrapolated value in the original article. Source: Chandler, K.; Pouillot, F. L. L.; Eckert, C. A. J. Chem. Eng. Data (1996), 41, 6-10.

200

0 50

150 P (bar)

Octacosane (C28H58; MW=394.76)

[O-2] 2000 y x 106

y1) x 106 T (K) P (bar) S (g/L) 343 162.0 1.29 257 181.0 2.62 471 200.0 4.91 825 1504 240.0 9.82 1: Calculated from S. Source: Chartier, T.; Delhomme, E.; Baumard, J. F.; Marteau, P.; Subra, P.; Tufeu, R. Ind. Eng. Chem. Res. (1999), 38(5), 1904-1910.

250

1000 0 150

200

250

P (bar)

569

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570

Solubility in Supercritical Carbon Dioxide

Octacosane (C28H58; MW=394.76)

[O-3]

106

140 6

x 110.0 118.5 125.0 129.0

y x 10

T (K) P (bar) 308.2 103.9 138.2 173.0 206.7

y1)

1: The order of magnitude(103) of the solubility in the source table was corrected to 10 5 based on Figure 4 in the same article. Source: Kalaga, A.; Trebble, M. J. Chem. Eng. Data (1999), 44(5), 1063-1066.

120 100 50

100

150

318.55

323.35

325.15

P (bar) 123.4 139.5 154.2 165.1 182.7 194.2 223.3 244.9 262.9 281.1 119.1 136.0 155.2 175.8 203.0 224.1 252.6 283.6 124.5 141.1 159.9 178.8 188.2 201.6 214.7 229.3 245.2 261.9 282.8 120.8 129.4 143.2 155.7 167.5

x

[O-4]

106 107 110 114 115 116 115 117 116 112 112 154 218 276 322 370 390 399 407 210 327 493 617 633 702 761 816 838 855 882 179 251 385 507 628

1200 307.9 K 318.6 K 323.4 K 325.2 K

800 y x 106

T (K) 307.85

250

P (bar)

Octacosane (C28H58; MW=394.76) y1)

200

400

0 100

CAT4240—CHAPTER 15—31/10/2006—19:18—KADAMBADI—XML MODEL C – pp. 569–585

200 P (bar)

300

Solubility Data O

571

172.9 659 181.8 756 189.9 821 197.0 899 205.2 933 214.9 966 221.9 987 237.1 1039 245.7 1060 264.7 1100 283.6 1108 1: Data measured by flow method. Source: McHugh, M. A.; Seckner, A. J.; Yogan, T. J. Ind. Eng. Chem. Fund. (1984), 23(4), 493-499.

Octacosane (C28H58; MW=394.76)

[O-5]

y x 106

y1) x 106 T (K) P (bar) 1000 318.55 132.3 203 177.5 325 323.35 126.4 203 135.9 325 136.5 325 138.0 326 500 167.8 545 201.7 698 213.9 750 254.3 850 270.8 863 311.0 850 0 326.7 863 100 325.15 120.6 203 178.2 750 1: Data measured in a view cell apparatus. Source: McHugh, M. A.; Seckner, A. J.; Yogan, T. J. Ind. Eng. Chem. Fund. (1984), 23(4), 493-499.

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318.6 K 323.4 K 325.2 K

200 P (bar)

300

572

Solubility in Supercritical Carbon Dioxide

Octacosane (C28H58; MW=394.76) 106

y1)

[O-6]

106

wx x P (bar) 3500 196.8 17000 1900 232.5 19000 2200 246.6 26000 3000 278.7 28000 3200 348.0 226.3 17000 1900 232.4 19000 2200 2500 276.2 26000 3000 289.9 28000 3200 357.0 239.8 17000 1900 242.2 19000 2200 272.2 26000 3000 284.4 28000 3200 366.4 254.8 19000 2200 150 274.8 26000 3000 288.8 28000 3200 1: Calculated from w. Source: Nieuwoudt, I.; du Rand, M. J. Supercrit. Fluids (2002), 22(3), 185-199.

338.5 K 348.0 K 357.0 K 366.4 K

y x 106

T (K) 338.5

200

250

300

P (bar)

Octacosane (C28H58; MW=394.76) 0.055 0.209 0.340 0.374 0.420 0.500 0.625 0.725 0.790 0.081 0.142 0.269 0.363 0.611 0.666 0.731 0.972 1.289 1.365 0.187 0.407 0.771 1.130 1.587 1.949

12.3 34.5 51.7 54.6 59.1 68.3 81.3 93.6 99.0 18.7 28.0 48.4 60.0 90.5 96.2 102.5 130.4 167.2 171.0 39.6 76.0 127.8 179.0 237.1 275.4

[O-7]

308.15 K 313.15 K 318.15 K

400

300 yx

y x 106

106

T (K) P (bar) 308.15 80 90 100 110 120 150 180 200 220 313.15 90 95 100 110 130 140 150 180 225 275 318.15 106 110 125 135 150 175

S(g/L)

200

100

0 50

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150 P (bar)

250

Solubility Data O

573

2.336 200 319.5 2.933 225 390.0 260 389.3 2.974 Source : Reverchon, E.; Russo, P.; Stassi, A. J. Chem. Eng. Data (1993), 38(3), 458-460.

[O-8]

Octacosane (C28H58; MW=394.76) y1)

106

323.7 K 343.2 K 362.5 K

y x 106

x T (K) P (bar) S (g/L) 5.47 323.7 204.5 773 228.5 6.90 944 250.5 7.71 1030 300.5 8.50 1088 376.0 8.35 1020 444.0 7.09 839 489.0 6.79 789 489.0 6.85 796 5.49 343.2 204.0 914 230.0 8.49 1327 12000 241.5 9.12 1395 270.0 13.26 1939 270.0 13.72 2006 270.5 13.76 2010 280.5 15.36 2214 8000 280.5 14.69 2118 310.0 20.01 2788 330.0 21.53 2942 359.0 25.86 3447 420.0 33.97 4339 4000 448.0 37.21 4676 550.0 46.16 5529 551.5 45.93 5499 720.0 54.00 6111 770.0 54.79 6119 0 810.0 55.39 6126 100 6.70 362.5 244.5 1179 288.5 14.06 2251 288.5 15.04 2408 302.0 17.42 2727 309.0 19.53 3025 320.0 20.72 3160 340.0 25.48 3786 349.0 28.73 4223 369.5 31.82 4576 379.5 33.95 4834 446.5 55.22 7430 504.0 69.63 9023 563.0 91.35 11455 571.0 91.79 11468 1: Calculated from S. Source : Swaid, I.; Nickel, D.; Schneider, G. M. Fluid Phase Equil. (1985), 21(1-2), 95-112.

300

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500 P (bar)

700

900

574

Solubility in Supercritical Carbon Dioxide

Octacosane (C28H58; MW=394.76) T (K)

P (bar)

yx

[O-9]

106

308.2

2000 308.2 K 318.2 K 328.2 K

1500 y x 106

50.3 499 63.8 387 91.0 388 111.2 410 133.8 447 157.2 565 188.9 761 204.1 870 318.2 48.6 380 64.1 387 90.7 422 111.7 473 132.9 552 155.1 697 178.2 830 205.1 948 328.2 49.3 383 64.2 410 89.4 426 110.0 391 130.0 618 151.0 975 178.6 1233 203.4 1570 Source : Yau, J. S.; Tsai, F. N. J. Chem. Eng. Data (1993), 38(2), 171-174.

1000

500

0 0

100

Octadecane (C18H38; MW=254.49)

[O-10] 70000 y x 106

y x 106 T (K) P (bar) 310 120.0 12000 145.0 14000 201.0 62000 320 145.0 12000 201.0 43000 Source : Schmitt, W. J.; Reid, R. C. Chem. Eng. Comm. (1988), 64, 155-176.

200

P (bar)

310 K 320 K

35000

0 100

150 P (bar)

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200

Solubility Data O

575

Octadecane (C18H38; MW=254.49) T(K)

P(bar)

yx

[O-11]

106

310

310 K 313 K 333 K 353 K

y x 106

100 1100 110 1600 120 2300 130 3600 140 3900 160 5200 180 5800 9000 200 6800 313 100 1600 110 2500 120 3500 130 4500 6000 140 5400 160 6700 180 7600 200 8600 333 100 200 3000 110 300 120 500 130 700 140 1100 0 160 2000 180 2500 50 200 3300 353 100 100 110 100 120 200 130 400 140 600 160 1200 180 1800 200 2200 Source : Eustaquio-Rincon, R. ; Trejo, A. Fluid Phase Equil. (2001), 185(1-2), 231-239.

100

1-Octadecanol (C18H38O; MW=270.49) T (K) P (bar) 323.4 160 180 200 208 250 266 270 290 350

S (g/L) 11.7 16.4 20.5 23.4 28.0 33.8 33.0 37.8 40.6

y1)

106

x 2630 3510 4230 4770 5430 6450 6270 7060 7290

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150

200

P (bar)

[O-12]

576

Solubility in Supercritical Carbon Dioxide

323.4 K 362.8 K 402.2 K

y x 106

400 40.2 7030 20000 520 34.4 5740 532 32.9 5470 362.8 200 7.8 2350 15000 220 13.9 3850 230 17.8 4760 230 17.0 4550 250 26.6 6710 10000 262 32.0 7840 280 33.3 7870 280 42.6 10000 330 88.8 19200 5000 402 220 7.1 2750 260 12.5 4090 280 25.3 7740 0 300 36.7 10600 150 330 69.8 18700 1: Calculated from S. 2: The solubility datum at 362.8 K and 330 bar was corrected as it is one order of magnitude smaller in th source than the actual value in the Friedrich's thesis. Synonyms : n-Octadecyl alcohol; 1-Stearyl alcohol Source : Friedrich, J.; Schneider, G. M. J. Chem. Thermodyn. (1989), 21(3), 307-319.

200

250

300

350

P (bar)

1-Octadecanol (C18H38O; MW=270.49)

[O-13]

106

318 K 328 K 338 K

y x 106

yx T (K) P (bar) 318 152.0 2720 202.5 3520 317.9 4070 20000 437.9 3190 328 139.9 1550 153.9 2240 176.9 3380 212.3 6170 10000 280.6 8750 443.2 15600 447.7 18200 338 145.8 1040 0 157.7 1550 191.8 3440 100 237.2 6570 324.0 13100 22900 452.8 Synonyms : n-Octadecyl alcohol; 1-Stearyl alcohol Source : Kramer, A.; Thodos, G. J. Chem. Eng. Data (1988), 33(3), 230-234.

CAT4240—CHAPTER 15—31/10/2006—19:18—KADAMBADI—XML MODEL C – pp. 569–585

300 P (bar)

500

Solubility Data O

577

1-Octadecanol (C18H38O; MW=270.49) T (K)

P (bar)

yx

[O-14]

106

310 K 320 K

y x 106

111.0 597 140.0 649 198.0 913 279.0 1030 320 111.0 517 140.0 1500 198.0 2620 279.0 3290 Synonyms : n-Octadecyl alcohol; 1-Stearyl alcohol Source : Schmitt, W. J.; Reid, R. C. Chem. Eng. Comm. (1988), 64, 155-176.

4000

310

2000

0 100

200 P (bar)

1-Octadecanol (C18H38O; MW=270.49)

308

318

328

P (bar) 50.7 68.2 102.7 127.6 160.2 177.9 201.7 50.0 70.0 86.2 111.9 133.8 154.4 175.8 199.6 49.8 69.6 86.2 111.0 133.1 153.8 174.8 200.3 48.6 70.3 87.6 110.7 132.4 153.0 175.0 199.3

[O-15]

y x 106 290 260 520 720 1020 1060 1090 420 430 460 660 880 1050 1400 2330 380 410 410 1000 1620 2160 2800 3500 540 340 380 540 1780 2880 3910 5090

6000 302 K 308 K 318 K 328 K 338 K

4000 y x 106

T (K) 302

300

2000

0 0

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100 P (bar)

200

578

Solubility in Supercritical Carbon Dioxide

338

50.0 350 68.8 400 84.5 450 111.0 480 130.7 930 151.7 1910 170.5 3020 204.4 4810 Synonyms : n-Octadecyl alcohol; 1-Stearyl alcohol Source : Yau, J.; Tsai, F. J. Chem. Eng. Data (1992), 37(3), 285-287.

Octadecylmercaptan (C18H38S; MW=286.56)

320

P (bar) 111 140 204 111 140 204

yx

[O-16] 9000

1810 4630 7700 1080 3380 7700

y x 106

T (K) 310

106

Synonyms : 1-Octadecanethiol; Stearyl mercaptan Source : Schmitt, W. J.; Reid, R. C. Chem. Eng. Comm. (1988), 64, 155-176.

310 K 320 K

4500

0 100

150

200

P (bar)

n-Octane (C8H18; MW=114.23) T (K)

y x 106 6000 4000 4000 5000 7000 62000 61000 39000 40000 39000 39000 42000 47000 72000

27.5 90000 39.8 42.1 59.3 60000 73.8 383.15 29.0 40.9 30000 60.2 74.0 81.4 99.3 0 119.7 0 131.3 140.0 Synonym: Octane Source: King, M. B.; Alderson, D. A.; Fallah, F. H.; Kassim, D. M.; Sheldon, J. R.; Mahmud, R. S. in: Chapter 2, Chemical Engineering at Supercritical Fluid Conditions, Paulaitis, M. E.; Penninger, J. M. L.; Gray, Jr., R. D.; Davidson, P. (Eds.) Ann Arbor Science, 1983, pp.31-80.

313.15 K 383.15 K

y x 106

313.15

P (bar)

[O-17]

50

CAT4240—CHAPTER 15—31/10/2006—19:18—KADAMBADI—XML MODEL C – pp. 569–585

100 P (bar)

150

Solubility Data O

579

Octyl 2,5-dichlorobenzoate (C15H20Cl2O2; MW=303.22)

[O-18]

106

P (bar) y x 86.4 3100 113.8 3100 161.4 3100 205.4 3100 98.8 7600 400 137.1 7600 192.3 7600 232.8 7600 264.9 7600 300 190.2 19200 213.9 19200 256.3 19200 289.8 19200 200 317.5 19200 309.7 31700 306.6 31700 291.2 31700 100 286.1 31700 284.7 31700 283.7 31700 0 287.4 31700 300.1 31700 250 311.3 31700 329.4 31700 334.6 46900 318.2 46900 304.8 46900 292.2 46900 294.3 46900 303.8 46900 321.2 46900 347.2 46900 367.4 46900 Source : Shen, Z.; McHugh, M. A.; Lott, K. M.; Wright, M. E. Fluid Phase Equil. (2004), 216(1), 1-12.

P (bar)

T (K) 308.25 318.95 338.65 363.25 299.65 313.75 333.45 352.75 374.75 296.25 311.55 334.15 353.25 373.15 296.05 297.95 303.95 308.75 312.25 318.75 323.55 334.65 344.35 357.25 295.65 299.65 302.65 308.15 312.65 318.75 332.65 348.75 364.65

y=0.0031 y=0.0076 y=0.0192 y=0.0317 y=0.0469

300

350 T (K)

P (bar)

M (mol/l)

y1)x 106

y x 106

Octyl(phenyl)(N ,N-diisobutylcarbamoyl)methylphosphine oxide (C24H42NO2P; MW=407.57) 6000 T (K)

12.5 100 0.0001 154.0 120 0.0015 1240.0 150 0.0170 200 0.0890 5380.0 1: Calculated from M. Source: Meguro, Y.; Iso, S.; Sasaki, T.; Yoshida, Z. Anal. Chem. (1998), 70(4),774-779. 333

400

[O-19]

3000

0 50

100

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150 P (bar)

200

580

Solubility in Supercritical Carbon Dioxide

[O-20]

Okadaic acid (C44H68O13; MW=805.00) T (K)

P (bar)

Cosolvent (vol %)

M x 106 (mol/L)

Methanol 20 0 < det. limit 0 < det. limit 0 < det. limit 5.0 1.24 15 5.0 0.91 5.0 1.80 5.0 3.76 10 5.0 3.74 6.0 8.19 7.5 4.35 7.5 8.96 5 8.5 3.99 8.5 11.05 8.5 15.15 0 333 5.0 1.81 50 8.5 2.30 346 390 8.5 3.17 Water 333 315 0.1 1.08 0.3 5.40 * det. limit: detection limit Synonym : 9,10-Deepithio-9,10-didehydroacanthifolicin Source : Gonzalez, J. C.; Vieytes, M. R.; Vieites, J. M.; Botana, L. M. J. Am. Oil Chem. Soc. (2001), 78(1), 77-81. 90 200 300 90 100 150 200 300 300 100 300 100 200 300 315

M x 106 (mol/L)

313

MeOH 5.0 vol% MeOH 7.5 vol% MeOH 8.5 vol% T = 313 K

150

250 P (bar)

Oleic acid (C18H34O2; MW=282.46)

[O-21]

106

x T (K) P (bar) S (g/L) 313.15 101.3 0.70 170 121.6 1.95 419 152.0 3.65 724 202.7 6.29 1160 253.3 9.05 1594 333.15 101.3 0.05 26 121.6 1.01 348 152.0 6.66 1684 253.3 71.20 13820 1: Calculated from S. Synonym: (Z )-9-Octadecenoic acid Source: Chrastil, J. J. Phys. Chem. (1982), 86(15), 3016-3021.

15000

y x 106

y1)

350

313.15 K 333.15 K

10000 5000 0 50

CAT4240—CHAPTER 15—31/10/2006—19:18—KADAMBADI—XML MODEL C – pp. 569–585

150 P (bar)

250

Solubility Data O

581

[O-22]

Oleic acid (C18H34O2; MW=282.46) 106

3000 308.15 K

y x 106

yx T (K) P (bar) 308.15 96.0 480 114.7 857 130.6 1103 150.6 1480 180.9 1958 200.9 2570 318.15 103.4 217 117.2 587 131.0 953 153.1 1306 169.6 1610 186.2 1886 Synonym : (Z)-9-Octadecenoic acid Source : Foster, N. R.; Yun, S. L. J.; Ting, S. S. T. J. Supercrit. Fluids (1991), 4(2), 127-130.

318.15 K

2000

1000

0 50

100

150 P (bar)

Oleic acid (C18H34O2; MW=282.46) T (K)

P (bar)

200

[O-23]

106

yx 1200 85.1 150 96.1 270 114.8 520 800 130.6 790 140.3 850 150.6 760 176.8 920 400 180.9 1060 333.15 129.9 139 139.6 147 144.1 282 0 162.3 496 50 177.5 496 181.6 509 Synonym : (Z )-9-Octadecenoic acid Source : King, M. B.; Alderson, D. A.; Fallah, F. H.; Kassim, D. M.; Sheldon, J. R.; Mahmud, R. S. in: Chapter 2, Chemical Engineering at Supercritical Fluid Conditions, Paulaitis, M. E.; Penninger, J. M. L.; Gray, Jr., R. D.; Davidson, P. (Eds.) Ann Arbor Science, 1983, pp.31-80.

308.15 K 333.15 K

y x 106

308.15

100

CAT4240—CHAPTER 15—31/10/2006—19:18—KADAMBADI—XML MODEL C – pp. 569–585

150 P (bar)

200

582

Solubility in Supercritical Carbon Dioxide

Oleic acid (C18H34O2; MW = 282.46) T (K)

P (bar)

W (g/kg CO2)

[O-24] 4000

y1) x 106

y x 106

138 5.7 890 207 15.0 2330 276 21.0 3260 323 138 3.0 470 207 15.0 2330 276 23.0 3570 333 138 0.5 75 206 7.6 1180 276 20.0 3110 1: Calculated from W. Synonym : (Z )-9-Octadecenoic acid Source : Maheshwari, P.; Nikolov, Z.; White, T.; Hartel, R. J. Am. Oil Chem. Soc. (1992), 69(11), 1069-76. (Also see Figure 2 in Nikolov, Z.; Maheshwari, P.; Hardwick, J.; Murphy, P.; Johnson, L. Develop. Food Sci. (1992), 29, 595-616.)

313 K 323 K 333 K

313

2000

0 100

200 P (bar)

Oleic acid (C18H34O2; MW=282.46)

[O-25] 3000 323.15 K 333.15 K

y x 106

w x 106 y1) x 106 T (K) P (bar) 323.15 124 1700 265 137 3900 610 151 5800 908 172 9800 1540 206 14900 2351 333.15 124 400 62 131 1700 265 137 3100 484 151 5400 845 199 9600 1508 1: Calculated from w. Synonym : (Z)-9-Octadecenoic acid Source : Nilsson, W. B.; Gauglitz, E. J. Jr.; Hudson, J. K. J. Am. Oil Chem. Soc. (1991), 68(2), 87-91.

300

1500

0 100

CAT4240—CHAPTER 15—31/10/2006—19:18—KADAMBADI—XML MODEL C – pp. 569–585

150 P (bar)

200

Solubility Data O

583

Oleic acid (C18H34O2; MW=282.46) T (K)

P (bar)

S (g/L)

y1)

x

[O-26]

106

116.0 2.9 563 1800 139.5 2.1 391 185.0 2.7 478 211.5 6.2 1073 313.15 105.5 3.2 756 1200 145.8 4.3 866 185.0 4.8 905 221.0 6.0 1088 234.3 7.4 1325 238.5 7.8 1388 600 259.3 9.0 1580 279.0 9.9 1714 323.15 165.0 2.9 618 173.5 3.3 688 190.8 3.1 625 0 208.8 5.8 1136 239.5 7.9 1489 100 251.0 8.4 1564 256.5 8.3 1538 262.2 8.7 1603 1: Calculated from S. Synonyms : (Z )-9-Octadecenoic acid Source : Skerget, M.; Knez, Z.; Habulin, M. Fluid Phase Equil. (1995), 109(1), 131-138. 303.15

y x 106

303.15 K 313.15 K 323.15 K

200 P (bar)

Oleic acid (1) + Olive oil (2) Mixture1) T (K)

P (bar)

w1 x

106

w2 x

[O-27]

106

20000 Acid, 313 K Acid, 333 K Oil, 313 K Oil, 333 K

313.15

w x 106

138 5400 800 207 10440 1560 276 17940 5060 333.15 138 2520 480 207 8190 910 276 17430 3570 1: Solubility was measured from an equimass mixture of 1 and 2. Source : Nikolov, Z.; Maheshwari, P.; Hardwick, J.; Murphy, P.; Johnson, L. Develop. Food Sci. (1992), 29, 595-616.

300

10000

0 100

CAT4240—CHAPTER 15—31/10/2006—19:18—KADAMBADI—XML MODEL C – pp. 569–585

200 P (bar)

300

584

Solubility in Supercritical Carbon Dioxide

Orange peel oil P (bar) 40.6 50.7 61.0 313.15 40.4 56.2 71.7 323.15 42.6 57.2 68.4 72.5 77.9 80.3 81.5 81.8 87.8 88.1 92.0 92.7 94.0 94.5 95.7 96.7 333.15 79.2 79.9 81.5 85.3 94.8 95.4 100.1 103.4 104.9 105.7 105.8 109.7 111.5 111.8 112.1 112.3 114.1 114.6

x

106

2300 2700 3000 3100 3600 5100 4100 4800 4600 6200 5500 8500 7400 8900 11600 10000 14800 15900 15000 19900 22200 26900 8500 8400 10700 9900 13000 13900 19000 23700 23500 26700 26900 39300 44600 50300 54200 57300 72800 98400

150000 303.15 K 313.15 K 323.15 K 333.15 K 343.15 K

100000 w x 106

T (K) 303.15

[O-28] w1)

50000

0 0

50

CAT4240—CHAPTER 15—31/10/2006—19:18—KADAMBADI—XML MODEL C – pp. 569–585

100 P (bar)

150

Solubility Data O

343.15

79.4 11000 80.1 9000 81.8 8900 100.7 15600 105.2 17500 105.4 17900 116.4 32800 120.3 42600 124.7 51300 125.1 56900 127.6 73500 130.6 104800 131.8 140100 1: Each datum represents the weight fraction of oil from one of the 3 different types of oranges: two from Brazil and one from Greece. Cold-pressed and dewaxed oils were used as feed material that has average monoterpene of about 98.5 wt%, including D-Limonene about 95.3 wt%. Source: Budich, M.; Brunner, G. Fluid Phase Equil. (1999), 158-160, 759-773.

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585

16

Solubility Data P

Palladium bis(acetylacetonate) (C10H14O4Pd; FW=304.64) T1)

(K)

P1)

(bar)

y1)

x

106

99 8.5 200 25.0 300 34.0 196 313.2 26.0 196 353.3 21.5 196 373.2 28.0 196 393.1 26.0 423.2 22.0 196 1: Obtained by digitizing the graph in the original article. Synonyms: Bis(2,4-pentanedionato) palladium; Pd(acac)2 Source: Yoda, S.; Hasegawa, A.; Suda, H.; Uchimaru, Y.; Haraya, K.; Tsuji, T.; Otake, K. Chem. Mater. (2004), 16(12), 2363-2368.

[P-1]

40 y x 106

313.0

20 0 0

100

200

300

P (bar)

y x 106

40 20 0 300

350

400

450

T (K)

Palladium bis(methylthioglycolate) (C6H10O4PdS2; FW=316.69) T (K) 323.15

P (bar) 150 200 250 300 350 400

M x 106 (mol/L) 63.7 74.2 81.4 86.3 90.3 93.3

[P-2]

y1) x 106 3.99 4.15 4.29 4.36 4.41 4.44

587

CAT4240—CHAPTER 16—1/11/2006—16:29—SRIDHAR—XML MODEL C – pp. 587–693

588

Solubility in Supercritical Carbon Dioxide

150 54.6 3.95 200 81.4 4.94 250 96.5 5.39 300 109.0 5.77 350 115.1 5.86 400 115.8 5.72 150 49.2 343.15 4.24 200 90.6 6.03 250 110.6 6.59 300 123.5 6.88 350 130.0 6.91 6.96 400 135.7 1: Calculated from M. Synonyms: Bis(methylthioglycolato)palladium; Pd(MTG)2 Source: Wenclawiak, B. W.; Wolf, A.; Wilnewski, S. in: Supercritical Fluids as Solvents and Reaction Media, Brunner, G. (ed.), Elsevier B.V., Amsterdam, Netherlands (2004), 323-340.(Another source: Wolf, A.: Sc.D. Thesis, Siegen University, Germany, 1999.)

y x 106

333.15

7

323.15K 333.15K 343.15K

5

3 100

250 P (bar)

400

Palladium bis(2,2,6,6-tetramethyl-3,5-heptanedionate) (C22H38O4Pd; FW=472.94) M x 104 y1) x 106 (mol/L) 1200 150 40.7 323.15 255 200 76.1 426 250 101.2 532 300 136.2 687 800 350 161.7 790 400 170.5 811 150 34.1 333.15 247 200 85.8 520 250 118.1 659 400 300 144.2 763 350 168.7 858 400 181.1 893 150 22.3 343.15 192 0 200 88.5 588 1002 250 142.0 845 300 172.5 960 350 185.7 987 1010 400 196.8 1: Calculated from M. Synonyms: Bis(2,2,6,6-tetramethyl-3,5heptanedionato) palladium; Pd(thd)2 Source: Wenclawiak, B. W.; Wolf, A.; Wilnewski, S. in: Supercritical Fluids as Solvents and Reaction Media, Brunner, G. (ed.), Elsevier B. V., Amsterdam, Netherlands (2004), 323-340.(Another source: Wolf, A.: Sc.D. Thesis, Siegen University, Germany, 1999.) P (bar)

y x 106

T (K)

[P-3]

CAT4240—CHAPTER 16—1/11/2006—16:29—SRIDHAR—XML MODEL C – pp. 587–693

323.15 K 333.15 K 343.15 K

50 P (bar)

400

Solubility Data P

589

[P-4]

Palladium bis(diisopropyldithiocarbamate) (C14H28N2PdS4; FW=459.07) 106

Mx y1) x 106 (mol/L) 150 6.61 323.15 0.414 200 8.77 0.491 250 9.04 0.476 300 9.71 0.490 350 9.71 0.475 400 9.86 0.469 150 4.75 333.15 0.344 200 10.85 0.658 250 13.15 0.734 300 13.49 0.714 350 14.94 0.760 400 16.54 0.816 150 2.97 343.15 0.257 200 15.51 1.030 250 18.00 1.070 300 18.39 1.020 350 20.30 1.080 1.120 400 21.94 1: Calculated from M. Synonym: Bis(diisopropyldithiocarbamato)palladium Source: Wenclawiak, B. W.; Wolf, A.; Wilnewski, S. in: Supercritical Fluids as Solvents and Reaction Media, Brunner, G. (ed.), Elsevier B.V., Amsterdam, Netherlands (2004), 323-340.(Another source: Wolf, A.: Sc.D. Thesis, Siegen University, Germany, 1999.) P (bar)

1.2

0.8

y x 106

T (K)

0.4

0.0 100

323.15 K 333.15 K 343.15 K

250

400

P (bar)

[P-5]

Palladium diimine · BArF complex1)

308.15

313.15

151 201 304 150 199 305

M3) x 105 (mol/L) 3.46 5.56 8.46 6.20 7.57 11.44

6

y4)x 106 1.86 2.82 3.99 3.49 3.96 5.51

y x 106

T (K) P2) (bar)

4 2

1: Brookhart's catalysts: Mixture of [N,N'0 (1,2-dimethyl-1,2-ethanediylidene)bis[2,6100 bis(1-methylethyl)benzenamine-ΚappaN ]] + methyl[1,1'-oxybis[ethane]]palladium(1 ) tetrakis[3,5-bis(trifluoromethyl)phenyl] borate(1-) and the same complex but with "(acetonitrile)" group instead of "[1,1'oxybis[ethane]]" group. 2: The pressure was calculated from temperature and density. 3: Obtained by digitizing the graph in the original article. 4: Calculated from M. Source: de Vries, T. J.; Vorstman, M. A. G.; Keurentjes, J. T. F.; Duchateau, R. Chem. Commun. (2000), (4), 263-264.

CAT4240—CHAPTER 16—1/11/2006—16:29—SRIDHAR—XML MODEL C – pp. 587–693

308.15 K 313.15 K

200 P (bar)

300

590

Solubility in Supercritical Carbon Dioxide

[P-6]

Palmitic acid (C16H32O2; MW=256.42) y x 106 0.5 24.2 34.8 133.0 267.0 554.0 562.0 759.0 995.0

1200 y x 106

T (K) P (bar) 313 80 91 91 100 110 151 151 201 248

600

0 50

Synonym: Hexadecanoic acid Source: Bamberger, T.; Erickson, J. C.; Cooney, C. L.; Kumar, S. K. J. Chem. Eng. Data (1988), 33(3), 327-333.

150

250

P (bar)

[P-7]

Palmitic acid (C16H23O2; MW=256.42) P (bar) y x 106 100 103 150 376 200 445 250 599 300 601 350 650 318.15 100 79 150 466 200 858 250 992 300 1105 350 1147 328.15 100 65 150 535 200 1013 250 1260 300 1450 350 1579 Synonym: Hexadecanoic acid Source: Gordillo, D.; Pereyra, C.; Martinez de la Ossa, E. J. J. Chem. Eng. Data (2004), 49(3), 435-438. T (K) 308.15

308.15 K 318.15 K 328.15 K

y x 106

1500

1000

500

0 50

CAT4240—CHAPTER 16—1/11/2006—16:29—SRIDHAR—XML MODEL C – pp. 587–693

150

250 P (bar)

350

Solubility Data P

591

[P-8]

Palmitic acid (C16H32O2; MW=256.42)

6

600 y x 10

y x 106 T (K) P (bar) 308.15 99 153 127 326 157 398 186 441 206 482 230 494 Synonym: Hexadecanoic acid Source: Iwai, Y.; Fukuda, T.; Koga, Y.; Arai, Y. J. Chem. Eng. Data (1991), 36(4), 430-432.

300

0 50

150

250

P (bar)

[P-9]

Palmitic acid (C16H32O2; MW=256.42)

60000

y x 106

y x 106 T (K) P (bar) 318 142.1 1420 158.2 1930 206.6 3600 257.1 5190 360.6 8700 328 144.1 1090 158.2 1740 211.2 4310 259.9 8130 362.1 16700 463.9 21500 573.5 27700 338 142.5 520 159.0 1290 213.8 3510 277.0 10900 362.7 19100 454.9 31700 59600 574.8 Synonym: Hexadecanoic acid Source: Kramer, A.; Thodos, G. J. Chem. Eng. Data (1988), 33(3), 230-234.

318 K 328 K 338 K

40000

20000

0 100

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300 P (bar)

500

592

Solubility in Supercritical Carbon Dioxide

[P-10]

Palmitic acid (C16H32O2; MW= 256.42) T (K)

P (bar)

W (g/kg CO2)

15000

y1) x 106

138 1.9 326 275 3.2 549 414 3.6 617 318 138 5.2 892 275 23.0 3930 414 23.0 3930 328 138 4.0 686 275 47.0 8000 345 76.0 12900 1: Calculated from W. Synonym: Hexadecanoic acid Source: Maheshwari, P.; Nikolov, Z.; White, T.; Hartel, R. J. Am. Oil Chem. Soc. (1992), 69(11), 1069-76.

y x 106

308

10000

308 K 318 K 328 K

5000

0 100

200

300

400

P (bar)

Palmitic acid (C16H32O2; MW=256.42) T (K)

Cosolvent (wt%)

[P-11]

y6 x 106

0.0 360 0.0 640 0.0 710 60000 0.0 1000 323.15 0.0 570 0.0 780 0.0 860 0.0 930 40000 Acetone 323.15 3.0 29000 88 3.0 50000 135 3.0 50000 190 3.0 57000 225 20000 3.0 57000 235 Methanol 323.15 3.0 2100 102 3.0 2900 132 3.0 3600 172 0 3.0 4300 212 50 3.0 4300 240 Water 323.15 3.0 500 110 3.0 570 135 3.0 640 172 3.0 710 207 228 3.0 710 1: Obtained by digitizing the graph in the original article. Some data may have large reading errors. Synonym: Hexadecanoic acid Source: Noh, M. J.; Kim, T. G.; Hong, I. K.; Yoo, K.-P. Korean J. Chem. Eng. (1995), 12(1), 48-55. 103 172 205 241 102 172 200 240

CO2 313 K CO2 323 K Acetone 323 K MeOH 323 K Water 323 K

y x 106

313.15

P (bar)

500

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150 P (bar)

250

Solubility Data P

593

Palmitic acid (C16H32O2; MW=256.42)

308.2

308.2

P (bar)

(mol%) Ethanol 99 0.00 1.06 1.57 3.22 4.16 5.09 5.24 6.70 6.86 7.44 8.27 8.83 197 0.00 0.99 1.54 2.96 5.03 5.07 5.27 5.68 5.88 8.25 n-Octane 99 0.00 0.66 0.67 1.75 1.88 2.76 4.36 6.95 7.66

197

[P-12]

y x 106 153 336 621 1350 2110 3220 3640 5350 6280 8010 8270 9740 464 712 1110 2160 4870 4220 4540 5660 6430 11300 153 226 236 340 533 804 1690 4470 4880

8.03

6030

8.24

6550

0.00

464

0.70

690

2.64

1140

3.87

1850

4.81

3100

5.49

3580

6.28

4680

6.80

5370

12000 EtOH 99 bar EtOH 197 bar Octane 99 bar Octane 197 bar

9000

y x 106

T (K)

Cosolvent1)

6000

3000

0 0

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5 Cosolvent (mol%)

10

594

Solubility in Supercritical Carbon Dioxide

6.94

5400

7.08

6500

7.27

5790

1: Cosolvent in CO2. Synonym: Hexadecanoic acid Source: Koga, Y.; Iwai, Y.; Hata, Y.; Yamamoto, M.; Arai, Y. Fluid Phase Equil. (1996), 125, 115-128.

Palmitic acid (C16H32O2; MW=256.42)

313.2

P(bar) 150

(mol/L)

0.000 0.016 0.018 0.029 0.047 0.048 0.053 0.058 0.064 0.072 0.083 0.086 0.103 0.105 0.149 0.197

[P-13]

y x 106 557 571 561 575 579 567 589 585 604 638 636 650 649 648 638 644

700

y x 106

T (K)

Water1)

600

500 0.0

0.1

0.2

Water (mol/L)

1: Cosolvent in CO2. Synonym: Hexadecanoic acid Source: Iwai, Y.; Uno, M.; Nagano, H.; Arai, Y. J. Supercrit. Fluids (2004), 28(2-3), 193-200.

Palmityl behenate (C38H76O2; MW=565.01) T (K)

P (bar)

S (g/L)

[P-14]

y1) x 106

y x 106

101.3 0.44 53 121.6 0.53 57 152.0 0.59 59 202.7 0.65 60 253.3 0.70 62 323.15 253.3 0.86 80 333.15 101.3 0.25 65 121.6 0.44 76 152.0 0.71 90 202.7 0.90 96 101 253.3 1.03 1: Calculated from S. Synonyms: Hexadecyl docosanoate; Cetyl behenate Source: Chrastil, J. J. Phys. Chem. (1982), 86(15), 3016-3021.

110

313.15

313.15 K 323.15 K 333.15 K

90

70

50 50

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150 P (bar)

250

Solubility Data P

595

Palm kernel oil

313.15

345 414 483

(g/kg CO2) 75 130 210

180000

w2) x 106 69800 115000 174000

w x 106

T (K) P1) (bar)

[P-15] W1)

1: Obtained by digitizing the graph in the original article. 2: Calculated from W. Source: Nik Norulaini, N. A.; Md Zaidul, I. S.; Anuar, O.; Azlan, A.; Omar, A. K. M. J. Chem. Eng. Japan (2004), 37(2), 194-203.

120000

60000 300

400 P (bar)

Palm kernel oil

[P-16] W1) w2) x 106 (g/kg CO2)

353.15

277 40 38900 345 75 70000 413 125 111000 482 141 124000 1: Obtained by digitizing the graph in the original article. 2: Calculated from W. Source: Nik Norulaini, N. A.; Md Zaidul, I. S.; Anuar, O.; Mohd. Omar, A. K. Sep. Purif. Tech.(2004), 39(3), 133-138.

140000 w x 106

T (K) P1) (bar)

80000 20000 250

Palm oil1)

350

450

P (bar)

[P-17]

T (K) P2) (bar) 348.15

500

194 255 300 343 396

Ethanol3) (wt%)

0 0 0 0 0

w2) x 106 169 702 1200 1710 2290

CAT4240—CHAPTER 16—1/11/2006—16:29—SRIDHAR—XML MODEL C – pp. 587–693

596

Solubility in Supercritical Carbon Dioxide

323.15

~ 10 60 775 90000 ~ 10 77 2950 ~ 10 82 13000 ~ 10 80 24000 ~ 10 94 24900 ~ 10 104 50500 60000 ~ 10 139 62700 ~ 10 175 85300 343.15 ~ 10 102 6200 ~ 10 141 17600 ~ 10 175 46500 30000 ~ 10 217 55800 363.15 ~ 10 138 4810 ~ 10 214 30000 383.15 ~ 10 141 1710 211 21200 ~ 10 0 1: Palm oil containing 85% triglycerides. 0 2: Obtained by digitizing the graph in the original article. 3: Cosolvent in CO2. Source: Brunner, G.; Peter, S. Sep. Sci. Technol. (1982), 17(1), 199-214.

w x 106

CO2 348 K w/EtOH 323 K w/EtOH 343 K w/EtOH 363 K w/EtOH 383 K

150

300 P (bar)

Para red (C16H11N3O3; MW=293.28)

[P-18]

y x 106 0.32 0.48 0.78 1.16 1.45 1.73 2.06 2.46 2.75 0.44 0.50 0.75 1.43 1.77 2.43 3.08 3.51 3.95 0.41 1.06 1.25 1.95 2.90 3.50 4.35 5.16

6

y x 106

T (K) P(bar) S x 102 (g/L) 328 122 0.11 152 0.21 182 0.38 213 0.60 243 0.77 274 0.96 304 1.17 334 1.43 355 1.62 338 122 0.12 152 0.19 182 0.33 213 0.68 243 0.89 274 1.27 304 1.67 334 1.95 355 2.23 348 152 0.13 182 0.41 213 0.54 243 0.91 274 1.43 304 1.80 334 2.31 355 2.79

450

328 K 338 K 348 K 358 K

4

2

0 100

CAT4240—CHAPTER 16—1/11/2006—16:30—SRIDHAR—XML MODEL C – pp. 587–693

200

300 P (bar)

400

Solubility Data P

597

358

122 0.04 0.22 152 0.13 0.47 182 0.27 1.27 213 0.54 2.22 243 1.18 2.85 274 1.75 3.80 304 2.31 4.76 334 2.98 5.91 355 3.33 6.46 Synonyms: 1-(4-Nitrophenylazo)-2naphthol; C. I. Pigment Red 1 Source: Fasihi, J.; Yamini, Y.; Nourmohammadian, F.; Bahramifar, N. Dyes Pigm. (2004), 63(2), 161-168.

Penicillin G (C16H18N2O4S; MW=334.39)

[P-19]

313.15 K 323.15 K 333.15 K

60

y x 106

T (K) P (bar) y x 106 313.15 100 5.35 150 4.85 200 14.30 250 18.50 300 20.00 350 19.80 323.15 100 4.62 150 6.13 200 18.20 250 27.00 300 38.70 350 46.20 333.15 100 4.20 150 8.49 200 23.90 250 38.90 300 52.90 350 63.30 Synonym: Benzylpenicillin Source: Gordillo, M. D.; Blanco, M. A.; Molero, A.; De la Ossa, E. M. J. Supercrit. Fluids (1999), 15(3), 183-190.

40

20

0 50

CAT4240—CHAPTER 16—1/11/2006—16:30—SRIDHAR—XML MODEL C – pp. 587–693

150

250 P (bar)

350

598

Solubility in Supercritical Carbon Dioxide

Penicillin V (C16H18N2O5S; MW=350.39) y x 106 T (K) P (bar) 314.85 80.8 62.3 90.1 97.0 114.7 177.0 144.0 213.0 173.0 268.0 207.7 328.0 242.5 373.0 280.5 432.0 324.85 79.9 58.7 91.2 99.4 115.8 203.0 143.5 245.0 170.7 308.0 208.1 401.0 241.4 437.0 279.6 501.0 334.85 80.1 54.5 91.7 92.3 117.4 215.0 144.0 312.0 171.4 391.0 207.8 433.0 240.7 520.0 280.2 576.0 Synonym: Phenoxymethylpenicillin Source: Ko, M.; Shah, V.; Bienkowski, P. R.; Cochran, H. D. J. Supercrit. Fluids (1991), 4(1), 32-39.

[P-20]

600 314.85 K 324.85 K 334.85 K

y x 106

400

200

0 50

150

1,2,3,4,6-Pentaacetyl-D-galactose (C16H22O11; MW=390.34) T (K) 313.15

P1)

(bar)

w1)

x

106

y2)

x

250

P (bar)

106

[P-21]

40000

y x 106

90.0 46500 5470 81000 96.0 9840 141000 106.0 18200 20000 238000 109.5 34000 110.0 189000 25600 1: Obtained by digitizing the graph in the 0 original article. 2: Calculated from w. 80 Synonyms: b-D-Galactopyranose pentaacetate; b-D-Galactose Source: Raveendran, P.; Wallen, S. L. J. Am. Chem. Soc. (2002), 124(25), 7274-7275.

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100 P (bar)

120

Solubility Data P

599

1,2,3,4,6-Pentaacetyl-D-glucose (C16H22O11; MW=390.34) T (K) P1) (bar)

w1) x 106

y2) x 106

50000

AGLU BGLU

y x 106

AGLU 313.15 83.0 33000 3800 88.5 133000 17000 90.5 183000 24600 96.0 245000 35300 101.5 292000 44400 25000 BGLU 313.15 88.0 28000 3240 94.0 80000 9700 101.0 145000 18800 102.2 198000 27100 0 104.0 287000 43400 80 1: Obtained by digitizing the graph in the original article. 2: Calculated from w. AGLU:a -form of 1,2,3,4,6-Pentaacetyl-D-glucose BGLU:b -form of 1,2,3,4,6-Pentaacetyl-D-glucose Synonyms: D-Glucose pentaacetate;DGlucopyranose pentaacetate Source: Raveendran, P.; Wallen, S. L. J. Am. Chem. Soc. (2002), 124(25), 7274-7275.

[P-22]

90

100

2,2',4,5,5'-Pentachlorobiphenyl (C12H5Cl5; MW=326.43) y x 106 115 176 235 280 332 383 436 474 506 549 589 648 711 782 841 920 20 55 112 179 244 305

[P-23]

1500 313 K 323 K 333 K

1000 y x 106

T (K) P (bar) 313 100 110 120 130 140 150 160 170 180 190 200 220 240 260 280 300 323 100 110 120 130 140 150

110

P (bar)

500

0 50

CAT4240—CHAPTER 16—1/11/2006—16:30—SRIDHAR—XML MODEL C – pp. 587–693

150

250 P (bar)

350

600

Solubility in Supercritical Carbon Dioxide

160 367 170 429 180 493 190 545 200 601 220 713 240 814 260 935 280 1030 300 1120 333 100 13 110 23 120 47 130 85 140 137 150 203 160 278 170 349 180 412 190 494 200 584 220 739 240 887 260 1070 280 1220 300 1360 Source: Anitescu, G.; Tavlarides, L. L. J. Supercrit. Fluids (1999), 14(3), 197-211.

2,2',4,5,5'-Pentachlorobiphenyl (C12H5Cl5; MW=326.43) T (K)

P (bar)

313

100 110 120 130 140 150 160 170 180 190 200 220 240 260 280 300

1)

n -Butane (mol%) 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0

y x 106 161 242 319 376 441 505 554 590 632 673 711 781 855 926 992 1070

CAT4240—CHAPTER 16—1/11/2006—16:30—SRIDHAR—XML MODEL C – pp. 587–693

[P-24]

Solubility Data P

601

323

313 K 323 K 333 K

y x 10

6

100 5.0 33 110 5.0 89 120 5.0 178 130 5.0 268 140 5.0 361 150 5.0 444 160 5.0 516 170 5.0 589 1600 180 5.0 650 190 5.0 713 200 5.0 768 220 5.0 888 1200 240 5.0 999 260 5.0 1120 280 5.0 1210 800 300 5.0 1300 333 100 5.0 23 110 5.0 41 120 5.0 77 400 130 5.0 133 140 5.0 198 150 5.0 277 160 5.0 375 0 170 5.0 477 50 180 5.0 568 190 5.0 673 200 5.0 763 220 5.0 929 240 5.0 1080 260 5.0 1260 280 5.0 1410 300 5.0 1570 1: Cosolvent in CO2. Source: Anitescu, G.; Tavlarides, L. L. J. Supercrit. Fluids (1999), 14(3), 197-211.

2,2',4,5,5'-Pentachlorobiphenyl (C12H5Cl5; MW=326.43) T (K)

P (bar)

313

100 110 120 130 140 150 160 170 180 190 200

1)

Methanol (mol%) 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0

y x 106 147 222 285 341 398 453 498 539 579 620 653

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150

250

350

P (bar)

[P-25]

602

Solubility in Supercritical Carbon Dioxide

313 K 323 K 333 K

y x 10

6

220 5.0 723 240 5.0 787 260 5.0 857 1600 280 5.0 920 300 5.0 994 323 100 5.0 28 110 5.0 80 1200 120 5.0 160 130 5.0 247 140 5.0 318 150 5.0 391 800 160 5.0 462 170 5.0 529 180 5.0 596 190 5.0 648 400 200 5.0 705 220 5.0 825 240 5.0 947 260 5.0 1070 0 280 5.0 1180 300 5.0 1270 50 333 100 5.0 21 110 5.0 35 120 5.0 69 130 5.0 121 140 5.0 189 150 5.0 273 160 5.0 366 170 5.0 447 180 5.0 514 190 5.0 602 200 5.0 698 220 5.0 869 240 5.0 1040 260 5.0 1220 280 5.0 1380 300 5.0 1520 1: Cosolvent in CO2. Source: Anitescu, G.; Tavlarides, L. L. J. Supercrit. Fluids (1999), 14(3), 197-211.

CAT4240—CHAPTER 16—1/11/2006—16:30—SRIDHAR—XML MODEL C – pp. 587–693

150

250 P (bar)

350

Solubility Data P

603

Pentachlorophenol (C6HCl5O ; MW=266.34) T (K)

P (bar)

[P-26]

6

y x 10

600 103 90.0 127 96.7 149 112.4 191 136.5 400 246 186.2 134 318 117.2 202 133.8 200 264 156.9 322 187.5 351 240.6 188 328 133.4 0 293 156.2 0 315 169.6 393 196.5 236.5 480 Source: Cross, W. J. ; Akgerman, A. Ind. Eng. Chem. Res. (1998), 37(4), 1510-1518.

308 K 318 K 328 K

y x 10

6

308

100

200 P (bar)

[P-27]

Pentachlorophenol (C6HCl5O; MW=266.34) T (K)

P (bar)

300

6

y x 10

293.15

293.15 K 314.15 K 332.65 K

y x 106

97.4 193 600 127 229 153 245 189 260 220 278 400 252 304 269 315 314.15 108 93 143 280 200 177 381 212 436 213 455 246 483 332.65 107 45 0 143 111 50 177 322 178 321 213 498 Source: Curren, M. S. S.; Burk, R. C. J. Chem. Eng. Data (2000), 45(5), 746-750.

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150 P (bar)

250

604

Solubility in Supercritical Carbon Dioxide

Pentachlorophenol (C6HCl5O; MW=266.34) M x 10 (mol/L)

y1) x 106

298 2950 308 2710 318 2240 1: Calculated from M. Source: Madras, G.; Erkey, C.; Akgerman, A. J. Chem. Eng. Data (1993), 38(3), 422-423. 111.5

155 159 160

165 6

T (K)

[P-28]

y x 10

P (bar)

6

150 290

300

310

320

T (K)

Pentachlorophenol (C6HCl5O; MW=266.34)

[P-29]

6

313 K 373 K 413 K

y x 10

6

y x 10 T (K) P (bar) 313 150 10 200 160 9000 250 260 300 350 350 440 400 540 6000 450 631 373 150 24 200 220 250 790 300 1310 3000 350 2090 400 2830 450 3390 413 150 162 0 200 519 250 1340 100 300 2870 350 4310 400 5800 450 8190 Source: Miller, D. J.; Hawthrone, S. B.; Clifford, A. A. J. Supercrit. Fluids (1997), 10(1), 57-63.

Pentachlorophenol (C6HCl5O; MW=266.34) T (K) P (bar) 292.25 109 143 147 175 210 252

H2O1) Sat'd Sat'd Sat'd Sat'd Sat'd Sat'd

6

y x 10

108 150 149 180 203 211

CAT4240—CHAPTER 16—1/11/2006—16:30—SRIDHAR—XML MODEL C – pp. 587–693

300

500

P (bar)

[P-30]

Solubility Data P

332.75

108 111 141 177 212 242 107 141 178 210 246 280

Sat'd Sat'd Sat'd Sat'd Sat'd Sat'd Sat'd Sat'd Sat'd Sat'd Sat'd Sat'd

11 29 159 278 415 492 24 87 349 593 767 1020

1200

y x 106

312.75

605

292.25 K 312.75 K 332.75 K

800

400

1: Cosolvent saturated in CO2. Source: Curren, M. S. S.; B, Robert C. J. Chem. Eng. Data (2000), 45(5), 746-750.

0 50

150

250

P (bar)

Pentacosane (C25H52; MW=352.68)

[P-31]

6

6

400 y x 10

y x 10 T (K) P (bar) 308.2 100 110 120 170 140 180 160 220 180 250 200 250 240 300 Source: Chandler, K.; Pouillot, F. L. L.; Eckert, C. A. J. Chem. Eng. Data (1996), 41(1), 6-10.

200

0 50

150

250

P (bar)

Pentacosane (C25H52; MW= 352.68)

[P-32]

6

6

1100 y x 10

y x 10 T (K) P (bar) 313 152 860 165 880 189 950 322 930 360 860 Source: Furuya, T.; Teja, A. S. J. Supercrit. Fluids (2004), 29(3), 231-236.

900 700 100

200

300 P (bar)

CAT4240—CHAPTER 16—1/11/2006—16:30—SRIDHAR—XML MODEL C – pp. 587–693

400

606

Solubility in Supercritical Carbon Dioxide

Pentadecafluorooctyl 2,5-dichlorobenzoate (C15H5Cl2F15O2; MW=573.09)

[P-33]

6

200

P (bar)

y x 10 T (K) P (bar) 84.3 700 309.95 700 328.35 114.5 700 347.95 138.8 700 363.45 152.6 89.9 1400 312.35 99.1 1400 317.75 1400 332.55 121.7 1400 346.35 141.2 1400 364.85 161.4 8800 317.95 102.1 8800 330.25 132.3 8800 344.75 160.4 8800 365.75 192.6 98.1 10800 315.55 10800 329.45 129.9 10800 350.55 172.8 10800 366.65 196.3 18700 334.85 143.3 18700 341.35 160.1 18700 353.45 182.7 18700 365.15 203.2 23900 355.65 184.4 365.85 202.2 23900 Source: Shen, Z.; McHugh, M. A.; Lott, K. M.; Wright, M. E. Fluid Phase Equil. (2004), 216(1), 1-12.

160

y=0.0007 y=0.0014 y=0.0088 y=0.0108 y=0.0187 y=0.0239

120

80 280

320

360

400

T (K)

1-Pentadecanol (C15H33O; MW=229.42)

[P-34]

6

y x 10

6

y x 10 T (K) P (bar) 15000 323.15 90.8 342 112.5 1538 125.8 2994 139.4 4454 10000 153.2 5618 165.9 6646 179.2 7626 5000 193.5 8604 201.0 9238 207.9 10030 0 212.3 10050 0 219.9 10100 228.5 11020 236.6 12000 Source: Artal, M.; Pauchon, V. ; Embid, J. M. ; Jose, J. J. Chem. Eng. Data (1998), 43(6), 983-985.

CAT4240—CHAPTER 16—1/11/2006—16:30—SRIDHAR—XML MODEL C – pp. 587–693

100

200 P (bar)

300

Solubility Data P

607

Pentadecanolactone (C15H28O2; MW=240.38) y x 10

[P-35]

4000 308.2 K 318.2 K 6

567 753 1180 1330 1620 825 1160 2200 2440 3130 Synonyms: 15-Pentadecanolide; Oxacyclohexadecan-2-one Source: Mishima, K.; Matsuyama, K.; Baba, M.; Hirabaru, T.; Yamauchi, S.; Tomokage, H.; Takahashi, K.; Yamasaki, N. J. Chem. Eng. Data (2001), 46(1), 69-72.

y x 10

T (K) P (bar) 308.2 91 101 151 203 253 318.2 91 101 151 203 253

6

2000

0 50

150 P (bar)

Pentaethylene glycol n -octyl ether (C18H38O6; MW=350.49) 2.35 2.55 5.19 5.57 9.91 1.03 2.38 2.52 5.57 5.19 9.88 1.00 2.32 2.52 5.54 5.16 9.85 2.38 2.52 5.16 5.57 9.88

y x 10

[P-36]

6

3010 3280 6830 7350 13600 1300 3050 3240 7350 6830 13600 1300 3050 3240 7350 6830 13600 3010 3280 6830 7350 13600

15000

293.15 K 303.15 K 313.15 K 323.15 K 333.15 K

10000 6

w (wt %)

2)

y x 10

T (K) P (bar) 293.15 75.6 77.5 115.6 115.6 164.3 303.15 81.3 100.1 115.7 127.8 158.0 189.2 313.15 105.2 121.7 152.2 181.9 187.6 211.8 323.15 155.2 180.4 205.8 205.8 229.0

1)

250

5000

0 50

CAT4240—CHAPTER 16—1/11/2006—16:30—SRIDHAR—XML MODEL C – pp. 587–693

150 P (bar)

250

608

Solubility in Supercritical Carbon Dioxide

333.15

152.8 1.09 1300 174.6 2.38 3050 205.4 2.52 3240 223.3 5.16 7350 224.4 5.54 6830 251.7 9.88 13600 1: Obtained by digitizing the graph in the original article. 2: Calculated from w. Synonyms: Octylpentaglycol; Octyl pentaethylene glycol ether Source: McFann, G. J.; Johnston, K. P.; Howdle, S. M. AIChE J. (1994), 40(3), 543-555.

Pentafluorobutyl 2,5-dichlorobenzoate (C11H7Cl2F5O2; MW=337.07)

[P-37]

6

200

P (bar)

y x 10 T (K) P (bar) 2300 323.25 103.9 2300 333.25 117.6 2300 351.75 136.1 2300 366.05 142.6 15200 325.45 114.1 15200 335.65 131.7 15200 349.55 155.6 15200 364.95 176.5 25400 338.15 138.8 25400 358.15 173.8 25400 367.65 187.4 34600 356.05 169.3 365.85 184.4 34600 Source: Shen, Z.; McHugh, M. A.; Lott, K. M.; Wright, M. E. Fluid Phase Equil. (2004), 216(1), 1-12.

y=0.0023 y=0.0152 y=0.0254 y=0.0346

150

100 320

340

360

Pentafluoropropyl 2,5-dichlorobenzoate (C10H5Cl2F5O2; MW=323.04)

[P-38]

6

y x 10

1400 1400 1400 2800 2800 2800 2800 2800 14800 14800 14800 14800 35800 35800 35800

200

P (bar)

T (K) P (bar) 317.15 93.6 335.25 116.9 355.75 134.0 88.5 313.95 325.05 106.6 334.85 120.7 350.55 140.2 366.85 149.4 323.65 108.0 328.45 119.7 346.75 152.2 365.05 176.5 349.75 162.5 354.25 170.0 365.45 189.5

380

T (K)

160

y=0.0014 y=0.0028 y=0.0148 y=0.0358

120

80 300

320

Source: Shen, Z.; McHugh, M. A.; Lott, K. M.; Wright, M. E. Fluid Phase Equil. (2004), 216(1), 1-12.

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340 T (K)

360

380

Solubility Data P

609

3,3',4',5,7-Pentahydroxyflavone (C15H10O7; MW=302.24) 6

30 308.2 K 318.2 K

6

20

y x 10

y x 10 T (K) P (bar) 308.2 101 6.10 152 9.65 203 10.50 253 12.00 318.2 101 5.42 152 18.80 203 21.40 253 22.00 Synonym: Quercetin Source: Matsuyama, K.; Mishima, K.; Ohdate, R.; Chidori, M.; Yang, H. J. Chem. Eng. Data (2003), 48(4), 1040-1043.

[P-39]

10 0 0

100

200 P (bar)

Perylene (C20H12; MW=252.31)

[P-40]

3 323 K 333 K 6

y x 106 0.62 0.85 1.14 1.37 1.45 1.50 1.56 1.63 1.69 0.82 1.11 1.49 1.80 1.84 1.86 2.00 2.07 2.15 2.20

2

y x 10

T (K) P (bar) 323 172.3 206.1 250.0 286.1 299.0 307.4 317.1 328.7 331.8 333 174.1 209.0 250.0 287.3 301.1 303.4 311.9 331.2 346.1 350.0

300

1

0 100

Synonyms: α-Perylene; Dibenz[de,kl ]anthracene Source: Anitescu, G.; Tavlarides, L. L. J. Supercrit. Fluids (1997), 10(3), 175-189.

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200

300 P (bar)

400

610

Solubility in Supercritical Carbon Dioxide

Perylene (C20H12; MW=252.31)

[P-41]

6

800 313 K 373 K 423 K 473 K 523 K

600 y x 10

6

y x 10 T (K) P (bar) 313 300 0.33 350 0.72 400 0.93 450 1.40 373 250 1.20 300 3.60 350 6.10 400 9.00 450 12.00 423 200 0.73 250 4.60 300 12.00 350 24.00 400 38.00 450 56.00 473 100 1.10 150 4.00 200 11.00 250 27.00 300 43.00 350 95.00 400 154.00 450 217.00 523 100 31.00 150 34.40 200 66.00 250 118.00 300 197.00 350 330.00 400 479.00 450 700.00 Synonyms: α-Perylene; Dibenz[de,kl ]anthracene Source: Miller, D. J.; Hawthorne, S. B.; Clifford, A. A.; Zhu, S. J. Chem. Eng. Data (1996), 41(4), 779-786.

400

200

0

0

Perylene (C20H12; MW=252.31) T (K) 333

P (bar) 214 227 241 255 272 288 301 315 329 346 369

Cosolvent (mol%) n-Butane 5 5 5 5 5 5 5 5 5 5 5

200

400

600

P (bar)

[P-42]

y x 106 1.58 1.94 2.20 2.44 2.68 2.89 3.21 3.35 3.59 3.74 3.94

CAT4240—CHAPTER 16—1/11/2006—16:30—SRIDHAR—XML MODEL C – pp. 587–693

Solubility Data P

333

Methanol 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5

0.95 1.02 1.15 1.25 1.37 1.46 1.54 1.66 1.75 1.82 1.69 1.88 2.10 2.22 2.30 2.50 2.69 2.77 2.91 3.03 3.08

220

10

2.05

239

10

2.31

248

10

2.43

257

10

2.58

267

10

2.66

278

10

2.86

290

10

3.00

306

10

3.20

322

10

3.35

335

10

3.58

348

10

3.70

5 4

6

333

209 218 237 251 267 284 300 318 335 350 212 229 250 260 272 290 307 318 333 346 350

y x 10

313

611

5% Butane, 333 K 5% MeOH, 313 K 5% MeOH, 333 K 10% MeOH, 333 K

3 2 1 0 100

Synonyms: a-Perylene; Dibenz[de,kl ]anthracene Source: Anitescu, G.; Tavlarides, L. L. J. Supercrit. Fluids (1997), 11(1,2), 37-51.

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200

300 P (bar)

400

612

Solubility in Supercritical Carbon Dioxide

Pesticides T (K)

[P-43]

P (bar)

313.15

200

Compounds Linuron1) Methoxychlor 2) Diclofopmethyl3) Diclofop4) 2,4-D5) 3,4-Dichloraniline6)

Formula C9H10Cl2N2O2 C16H15Cl3O2 C16H14Cl2O4 C15H12Cl2O4 C16H12Cl4O6 C6H5Cl2N

MW

7)

S (g/L)

y x 106

4.25 3.80 8.55 0.34 0.43 11.65

892 575 1309 54 102 3747

249.09 345.65 341.19 327.16 221.04 162.02

8)

1: 3-(3,4-Dichlorophenyl)-1-methoxy-1-methylurea. 2: 1,1,1-Trichloro-2,2-bis(4-methoxyphenyl)ethane. 3: Methyl 2-[4-(2,4-dichlorophenoxy)phenoxy]propanoate. 4: 2-[4-(2,4-Dichlorophenoxy)phenoxy]propanoic acid. 5: (2,4-Dichlorophenoxy)acetic acid. 6: 3,4-Dichlorobenzenamine. 7: The average of the two solubilities measured by two different methods. 8: Calculated from S. Source: Schaefer, K.; Baumann, W. Fresenius Z. Anal. Chem. (1988), 332(2), 122-124.

Phenanthrene (C14H10; MW=178.23) 1)

1)

[P-44]

6

318.15 K 338.15 K

y x 10

6

T (K) P (bar) y x 10 318.15 119 600 3000 134 700 145 850 158 1100 169 1300 2000 185 1450 197 1500 220 1650 1000 255 1800 338.15 158 850 174 1300 0 190 1600 200 2150 50 220 2450 246 2950 1: Obtained by digitizing the graph in the original article. Source: Andrews, A. T.; Ahlert, R. C. J. Env. Sci. Health, Part A: Toxic/Hazard. Subst. Environ. Eng. (2001), A36(1), 89-100.

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150 P (bar)

250

Solubility Data P

613

Phenanthrene (C14H10; MW=178.23) y x 106

T (K)

P (bar)

313

107.1 114.0 122.2 127.9 134.6 142.6 151.4 161.6 172.6 182.7 193.3 203.0 213.9 223.6 234.4 244.3 254.9 264.6 275.9 285.8 296.3 307.3 317.3 327.7 338.2 350.0 110.2

423 544 662 740 825 919 1017 1119 1222 1304 1388 1465 1561 1643 1720 1784 1861 1929 2000 2060 2118 2160 2200 2256 2290 2341 299

113.9 117.1 121.3 124.0 127.7 134.5 141.7 147.6 154.5 164.5 172.9 183.0 192.4 203.8 213.8 224.3 234.7

340 390 446 487 560 680 805 911 1020 1188 1302 1451 1600 1770 1915 2048 2189

323

CAT4240—CHAPTER 16—1/11/2006—16:30—SRIDHAR—XML MODEL C – pp. 587–693

[P-45]

614

Solubility in Supercritical Carbon Dioxide

4500

313 K 323 K 333 K

3000 6

2300 2400 2514 2600 2666 2727 2811 2893 2940 3000 3058 3102 333 200 259 314 360 429 503 623 762 948 1091 1240 1399 1571 1760 1927 2126 2304 2525 2690 2880 3022 3200 3401 3560 3640 3719 3823 3920 3988 4078 Source: Anitescu, G.; Tavlarides, L. L. J. Supercrit. Fluids (1997), 10(3), 175-189.

y x 10

244.6 254.9 265.7 275.6 281.5 289.4 300.0 309.9 316.5 324.2 332.0 340.3 111.3 117.0 121.0 125.2 130.0 135.0 141.3 148.6 158.1 163.5 170.0 177.1 185.0 193.6 203.3 213.6 223.9 234.5 244.2 255.6 265.3 275.9 288.6 300.0 306.6 315.3 323.8 334.2 342.0 350.0

1500

0 0

100

CAT4240—CHAPTER 16—1/11/2006—16:30—SRIDHAR—XML MODEL C – pp. 587–693

200 P (bar)

300

400

Solubility Data P

615

Phenanthrene (C14H10; MW=178.23)

[P-46]

6

6

1800

y x 10

y x 10 T (K) P (bar) 318.15 101 354 127 1010 151 1280 175 1540 328.15 102 176 125 643 145 1090 Source: Barna, L.; Blanchard, J-M.; Rauzy, E.; Berro, C. J. Chem. Eng. Data (1996), 41(6), 1466-1469.

318.15 K 328.15 K

1200 600 0 50

Phenanthrene (C14H10; MW = 178.23) T (K)

P (bar)

308.2

78.3 79.8 80.4 80.9 82.2 82.5 83.4 84.4 85.1 85.6 86.0 89.0 89.3 91.8 95.1 96.6 97.4 99.1 100.0 100.3 109.2 109.5 110.0 111.2 116.5 119.5 120.7 121.0 121.9

yx

106

130 170 180 180 280 250 270 350 270 260 270 420 410 460 450 550 510 580 540 560 690 690 620 650 760 790 780 760 790

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100

150

200

P (bar) [P-47]

616

323.2

870 870 870

140.4

940

141.4

950

142.0

950

150.5

1020

151.7

1030

160.5 163.0

1100 1090

170.4

1160

171.7

1160

180.5

1170

181.0

1210

182.6

1230

191.2

1250

201.6 203.5 95.0 100.0 105.0 110.0 115.0 120.0 124.6 130.0 134.0 145.0 156.0 169.5 184.5 198.0 208.0 216.0 224.5 232.5 244.2 254.0 89.4 92.0 95.5 100.1 102.0 105.2 105.9 106.7 108.1 108.8

1340 1330 160 310 460 610 720 800 920 950 1090 1250 1400 1480 1650 1840 1960 2060 2080 2200 2270 2390 40 50 70 150 160 260 290 300 340 320

110.2 114.5

3000

308.2 K 318.2 K 323.2 K 328.2 K

2000 6

130.0 130.5 131.2

y x 10

318.2

Solubility in Supercritical Carbon Dioxide

.

1000

0 50

410 490

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150 P (bar)

250

Solubility Data P

328.2

617

118.5 121.0 125.7 129.4 130.3 135.6 151.0

650 640 830 940 980 820 1430

156.0

1480

156.5

1520

160.5

1560

166.0

1690

167.0

1690

168.2

1650

174.6

1880

181.0

1740

181.4

1790

193.0

1930

195.6

1940

202.0

2090

212.2

2220

219.5

2240

228.5

2470

90.0

40

95.0

60

100.0

100

105.0

170

110.0

260

115.0

380

120.0

550

125.0

710

130.0

830

134.2

950

137.2

980

145.5

1210

157.0

1490

166.1

1680

174.8

1820

186.1

2010

194.2

2080

205.5

2320

209.8 214.7

2400 2520

225.2

2670

237.0

2730

245.0

2930

Source: Bartle, K. D.; Clifford, A. A.; Jafar, S. A. J. Chem. Eng. Data (1990), 35(3), 355-360.

CAT4240—CHAPTER 16—1/11/2006—16:30—SRIDHAR—XML MODEL C – pp. 587–693

618

Solubility in Supercritical Carbon Dioxide

[P-48]

Phenanthrene (C14H10; MW=178.23) 6

6

1600 y x 10

y x 10 T (K) P (bar) 308.2 101 556 121 734 141 937 161 1107 181 1244 Source: Goodarznia, I.; Esmaeilzadeh, F. J. Chem. Eng. Data (2002), 47(2), 333338.

800

0 100

150

200

P (bar)

Phenanthrene (C14H10; MW=178.23)

303.15 K 323.15 K 343.15 K

4000

6

y x 10 400 491 647 922 1220 1230 1420 1460 141 556 829 2330 2920 2840 23 168 509 1630

y x 10

T (K) P (bar) 303.15 80.9 86.4 104.3 138.8 242.2 276.7 380.1 414.5 323.15 104.3 118.1 138.8 276.7 345.6 414.5 343.15 104.3 118.1 138.8 207.7

[P-49]

6

3000 2000 1000 0 50

150

276.7 3500 380.1 3950 414.5 4130 Source: Johnston, K. P.; Ziger, D. H.; Eckert, C. A. Ind. Eng. Chem. Fund. (1982), 21(3), 191-197.

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250 P (bar)

350

450

Solubility Data P

619

Phenanthrene (C14H10; MW=178.23)

[P-50]

6

4000 318 K 328 K 338 K

y x 10

6

y x 10 T (K) P (bar) 318 120 849 160 1400 200 1700 240 2230 280 2280 328 120 465 160 1510 200 2140 240 2790 280 3190 338 120 328 160 1180 200 2370 240 3280 3840 280 Source: Kurnik, R. T.; Holla, S. J.; Reid, R. C. J. Chem. Eng. Data (1981), 26(1), 47-51.

2000

0 100

200 P (bar)

Phenanthrene (C14H10; MW=178.23)

[P-51]

6

6

1500 y x 10

y x 10 T (K) P (bar) 100 313.1 653 125 949 150 1080 175 1240 1220 200 Source: Kwiatkowski, J.; Lisicki, Z.; Majewski, W. Ber. Bunsenges. Phys. Chem. (1984), 88(9), 865-869.

1000 500 50

150

[P-52]

6

y x 10

3000

6

318.15 K 328.15 K

y x 10

732 1130 1390 1680 1780 1840 404 1260 1700 2150 2280 2330

250

P (bar)

Phenanthrene (C14H10; MW=178.23) T (K) P (bar) 318.15 120 160 200 240 255 270 328.15 120 160 200 240 255 270

300

2000

1000

0 100

Source: Lee, L.-s.; Huang, J.-f.; Zhu, O.-x. J. Chem. Eng. Data (2001), 46(5), 1156-1159.

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200 P (bar)

300

620

Solubility in Supercritical Carbon Dioxide

Phenanthrene (C14H10; MW=178.23) yx

512 707 1018 1158 1263 1454 1569 1634 247 356 660 815 1067 1306 1492 1750 1942 2088 2157 2194 107 383 904 934 1352 1764 2076 2377 2599 2831 2991 74 238 576 1172 1724 2272 2814 3347 3683 4011

4500 308 K 318 K 328 K 338 K

3000 y x 106

T (K) P (bar) 308 89.2 93.1 130.4 155.9 167.7 199.1 227.5 254.0 318 97.1 100.0 115.7 123.6 140.2 159.8 180.4 200.1 218.7 239.3 256.9 274.6 328 101.0 116.7 136.3 139.3 154.9 176.5 195.2 212.8 232.4 250.1 267.7 338 103.0 119.6 137.3 159.8 180.4 201.0 219.7 236.3 258.9 294.2

[P-53]

106

1500

0 50

Source: Sako, T.; Yamane, S.; Negishi, A.; Sato, M. Sekiyu Gakkaishi (1994), 37(3), 321-327.

CAT4240—CHAPTER 16—1/11/2006—16:30—SRIDHAR—XML MODEL C – pp. 587–693

150 P (bar)

250

Solubility Data P

621

Phenanthrene (C14H10; MW=178.23)

[P-54]

106

4000 308.15 K 328.15 K

y x 106

yx T (K) P (bar) 308.15 120 887 150 1120 200 1390 250 1580 300 1770 328.15 120 479 160 1460 200 2060 240 2700 280 3000 Source: Sane, A.; Taylor, S.; Sun, Y.-P.; Thies, M. C. J. Supercrit. Fluids (2004), 28(2-3), 277-285.

2000

0 50

150

250

[P-55]

Phenanthrene(C14H10; MW=178.23)

600

y x 106

y x 106 P (bar) T (K) 85.0 315.05 52.5 317.95 31.6 317.95 39.4 322.95 21.6 328.25 19.5 332.75 21.2 95.0 317.95 239.5 318.45 200.0 318.45 166.7 323.05 137.4 327.95 101.7 333.25 79.8 111.0 323.35 435.0 328.25 300.8 333.35 184.4 337.85 159.2 121.0 323.25 650.5 328.15 489.4 332.85 374.0 333.15 339.9 Source: Zhao, S.; Wang, R.; Yang, G. J. Supercrit. Fluids (1995), 8(1), 15-19.

350

P (bar)

85 bar 95 bar 111 bar 121 bar

400

200

0 310

CAT4240—CHAPTER 16—1/11/2006—16:30—SRIDHAR—XML MODEL C – pp. 587–693

320

330 T (K)

340

622

Solubility in Supercritical Carbon Dioxide

[P-56]

Phenanthrene (C14H10; MW=178.23) P (bar)

328.15

200.5 200.5 200.5 200.5 111.0 111.0 140.0 140.5 201.0 201.0 305.0 202.0 202.0 202.0 202.0

Cosolvent y x 106 (mol%) Acetone 3570 3.3 4610 5.5 6690 9.0 6250 9.4 Benzene 4.0 1490 9.4 1910 8.8 4970 3.7 2590 2.7 3900 7.7 8610 1.7 4410 Cyclohexane 3530 2.6 5850 5.8 Methylene Chloride 5320 5.7 13.1 11800

15000 Acetone Benzene Cy-Hex CH2Cl2

10000

200 bar

y x 106

T (K)

5000

0 0

5

10

15

Cosolvent (mol%)

Source: Schmitt, W. J.; Reid, R. C. Fluid Phase Equil. (1986), 32(1), 77-99.

Phenanthrene (C14H10; MW=178.23) T (K) 323

P (bar) 104.4 118.2 132.0 145.8 173.3 242.3 345.7 449.0 118.2 132.0 173.3 173.3 242.3 345.7

Cosolvent1) (mol %) Acetone 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 2.5 2.5 2.5 2.5 2.5 2.5

y x 106 142 358 613 964 1980 2140 2260 4090 991 1770 2710 3110 4180 5630

CAT4240—CHAPTER 16—1/11/2006—16:30—SRIDHAR—XML MODEL C – pp. 587–693

[P-57]

Solubility Data P

104.4 118.2 132.0 145.8 173.3 242.3 345.7 104.4 118.2 132.0 145.8 173.3 242.3 345.7 104.4 118.2 138.9 145.8 173.3 207.8 242.3 276.7 345.7

Methanol 1.0 1.0 1.0 1.0 1.0 1.0 1.0 2.5 2.5 2.5 2.5 2.5 2.5 2.5 3.9 3.9 3.9 3.9 3.9 3.9 3.9 3.9 3.9

224 730 1000 1280 1720 2710 3260 462 948 1160 1540 3110 5490 6360 474 874 983 1280 1690 4630 5840 7940 13700

16000 Acetone 1.0% Acetone 2.5% Methanol 1.0% Methanol 2.5% Methanol 3.9%

12000 y x 106

323

623

8000

4000

0 50

250

450

P (bar)

1: Cosolvent in CO2 on a solute-free basis. Source: Van Alsten, J. G.; Eckert, C. A. J. Chem. Eng. Data (1993), 38(4), 605-610.

Phenanthrene (C14H10; MW=178.23) T (K) 313

P (bar) 103 119 131 144 160 184 201 215 226 240 270 311 348

n-Butane1) (mol%) 5 5 5 5 5 5 5 5 5 5 5 5 5

y x 106 510 860 1020 1280 1500 1810 2000 2150 2260 2410 2670 2950 3170

CAT4240—CHAPTER 16—1/11/2006—16:30—SRIDHAR—XML MODEL C – pp. 587–693

[P-58]

624

Solubility in Supercritical Carbon Dioxide

333

333

100 118 131 145 159 186 200 213 228 241 275 312 350 102 111 129 145 159 173 190 221 254 282 301 320 349

10 10 10 10 10 10 10 10 10 10 10 10 10 5 5 5 5 5 5 5 5 5 5 5 5 5

580 1060 1380 1680 1950 2390 2570 2760 2970 3130 3540 3890 4160 310 470 860 1300 1700 2080 2500 3280 4050 4620 5010 5390 5880

101 110 130 144 160 174 192 220 255 279 300 321 341

10 10 10 10 10 10 10 10 10 10 10 10 10

450 700 1240 1690 2130 2630 3190 4120 5200 5900 6480 6980 7410

8000 313 K, 5% C4H10 313 K, 10% C4H10 333 K, 5% C4H10 333 K, 10% C4H10

6000

y x 106

313

4000

2000

0 0

100

1: Cosolvent in CO2. Source: Anitescu, G.; Tavlarides, L. L. J. Supercrit. Fluids (1997), 11(1,2), 37-51.

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200 P (bar)

300

400

Solubility Data P

625

Phenanthrene (C14H10; MW=178.23)

313

313

P (bar)

Ethane1) (mol%)

110 125 141 156 170 183 197 210 225 239 251 266 280 295 308 323 336 350

5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5

570 750 940 1140 1300 1450 1600 1730 1850 1980 2070 2190 2290 2380 2460 2540 2610 2660

109 124 140 156 170 185 199 211 224 240 250 265 280 295 309 324 335 350

10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10

580 830 1040 1220 1400 1590 1750 1880 2040 2200 2270 2380 2500 2600 2700 2780 2850 2920

y x 106

6000 313 K, 5% C2H6 313 K, 10% C2H6 333 K, 5% C2H6 333 K, 10% C2H6

4000 y x 106

T (K)

[P-59]

2000

0 0

100

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200 P (bar)

300

400

626

Solubility in Supercritical Carbon Dioxide

333

333

111 126 142 155 169 182 195 210 224 238 252 266 281 294 308 322 337 350 104 117 125 138 152 166 179 193 206 219 235 251 269 286 304 321 338 349

5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10

280 500 830 1140 1510 1800 2100 2400 2660 2910 3160 3400 3650 3820 4070 4230 4400 4510 210 400 590 900 1220 1600 1940 2260 2510 2790 3070 3380 3700 4000 4300 4500 4730 4880

1: Cosolvent in CO2. Source: Anitescu, G.; Tavlarides, L. L. J. Supercrit. Fluids (1997), 11(1,2), 37-51.

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Solubility Data P

627

Phenanthrene (C14H10; MW=178.23)

[P-60] y1) x 106

P (bar)

Ethane2) 0.33 600 850 1080 1300 1520 1730 1930 2140 2340 2520 2700 2880 3050 3200 3360 3520 3650 3790 3930 4050 4170 4280 4380 4480 4570 4650

0.00 0.10 0.20 380 450 500 500 590 670 630 750 850 750 900 1030 880 1040 1200 990 1150 1360 1100 1280 1530 1190 1400 1680 1290 1530 1840 1380 1650 1990 1470 1760 2130 1550 1880 2260 1630 2000 2400 1700 2100 2520 1770 2200 2650 1840 2270 2770 1900 2350 2880 1960 2420 2990 2020 2500 3100 2070 2560 3200 2120 2640 3290 2170 2700 3380 2220 2760 3480 2270 2810 3550 2310 2870 3630 2350 2920 3700 1: The temperature of the system is 313 K. 2: Cosolvent expressed in mole fraction in CO2. 8000 Source: Anitescu, G.; Tavlarides, L. L. J. Supercrit. Fluids (1997),11(1,2), 37-51. 100 110 120 130 140 150 160 170 180 190 200 210 220 230 240 250 260 270 280 290 300 310 320 330 340 350

0.52 950 1220 1490 1750 2010 2260 2500 2720 2950 3170 3370 3580 3770 3950 4140 4300 4460 4620 4760 4900 5040 5150 5270 5380 5480 5570

1.00 1550 2000 2420 2840 3220 3570 3890 4190 4450 4700 4930 5140 5320 5500 5660 5810 5950 6080 6200 6310 6420 6540 6640 6750 6850 6940

0.0 0.1 0.2 0.33 0.52 0.7 1.0

6000

y x 106

0.70 1200 1510 1820 2120 2420 2700 2970 3220 3480 3710 3950 4160 4360 4560 4750 4930 5100 5260 5400 5540 5670 5780 5890 5990 6070 6150

4000 2000 0 0

100

200 P (bar)

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300

400

628

Solubility in Supercritical Carbon Dioxide

[P-61]

Phenanthrene (C14H10; MW=178.23) T (K)

P (bar)

Methanol1) (mol%)

y x 106

313

313 K, 5% MeOH 333 K, 5% MeOH 333 K, 10% MeOH

y x 106

103 5 640 108 5 770 118 5 1000 127 5 1150 138 5 1420 152 5 1660 6000 167 5 1910 180 5 2130 195 5 2400 207 5 2550 222 5 2790 4000 241 5 3040 333 109 5 370 113 5 430 120 5 550 130 5 760 137 5 950 2000 145 5 1200 153 5 1540 166 5 2030 179 5 2510 193 5 2890 0 227 5 3600 0 250 5 4000 333 103 10 440 118 10 680 124 10 790 131 10 960 141 10 1340 150 10 1800 162 10 2420 172 10 2950 183 10 3500 193 10 3950 200 10 4200 250 10 5460 1: Cosolvent in CO2. Source: Anitescu, G.; Tavlarides, L. L. J. Supercrit. Fluids (1997),11(1,2), 37-51.

CAT4240—CHAPTER 16—1/11/2006—16:30—SRIDHAR—XML MODEL C – pp. 587–693

100

200 P (bar)

300

Solubility Data P

629

[P-62]

Phenanthrene (C14H10; MW=178.23)

308.2

P (bar)

(mol%)

148 150

0.00 1.53 1.69 2.29 2.44 3.46 3.69 3.77 4.73 4.87 5.91 6.11 6.46 6.87 7.31 7.40 7.45

y x 106 1030 1670 1810 1960 2100 2350 2760 2450 3470 3010 3930 4000 4400 4470 4760 4800 4460

6000 148 bar 150 bar

4500 y x 106

T (K)

n-Octane1)

3000 1500 0 0

2

4

6

8

Octane (mol%)

1: Cosolvent in CO2. Source: Koga, Y.; Iwai, Y.; Hata, Y.; Yamamoto, M.; Arai, Y. Fluid Phase Equil. (1996), 125, 115-128.

Phenanthrene (C14H10; MW=178.23) T (K) 313

313

P (bar) 110 118 127 137 149 163 180 200 221 241 262 282 300 313 330 346 109 115 125 137 152

Propane1) (mol%) 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 10 10 10 10 10

y x 106 610 700 820 980 1140 1310 1510 1730 1940 2150 2330 2490 2610 2680 2790 2860 690 810 1040 1260 1510

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[P-63]

630

Solubility in Supercritical Carbon Dioxide

333

10 10 10 10 10 10 10 10 10 10 10 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10

1700 1970 2100 2320 2550 2710 2890 3060 3200 3290 3390 480 740 1180 1520 1800 2050 2300 2600 2970 3320 3770 4070 4320 4580 4800 5050 670 840 1050 1450 1870 2290 2600 3000 3410 3740 4320 4700 5070 5420 5700 6060

313 K, 5% C3H8 313 K, 10% C3H8 333 K, 5% C3H8 333 K, 10% C3H8

6000

4000 y x 106

333

165 184 196 214 234 250 267 287 303 317 334 117 129 146 159 171 181 193 207 223 241 263 279 295 309 324 338 117 124 132 145 159 174 186 200 214 227 249 265 280 297 311 330

2000

0 0

100

1: Cosolvent in CO2. Source: Anitescu, G.; Tavlarides, L. L. J. Supercrit. Fluids (1997), 11(1,2), 37-51.

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200 P (bar)

300

400

Solubility Data P

631

Phenanthrene (C14H10; MW=178.23)

[P-64]

Cosolvent y x 106 (mol%) 308 100 0.0 571 120 0.0 787 150 0.0 1010 200 0.0 1250 250 0.0 1460 300 0.0 1620 350 0.0 1710 n-Octane 120 3.5 1940 120 3.5 2000 150 3.5 2360 150 3.5 2260 200 3.5 2700 300 3.5 3000 350 3.5 3220 120 5.25 2520 150 5.25 2980 200 5.25 3540 4070 250 5.25 4580 350 5.25 3840 120 7.0 150 7.0 4060 200 7.0 4570 200 7.0 4710 250 7.0 5140 350 7.0 5360 n-Pentane 120 3.5 1060 150 3.5 1390 200 3.5 1730 250 3.5 1970 300 3.5 2140 350 3.5 2430 Undecane 120 3.5 2560 250 3.5 3570 250 3.5 3620 350 3.5 3780 Source: Dobbs, J. M.; Wong, J.; Johnston, K. P. J. Chem. Eng. Data (1986), 31(3), 303-308. P (bar)

y x 106

T (K)

8000

Pure CO2 Octane 3.5% Octane 5.25% Octane 7.0% Pentane 3.5% Undecane 3.5%

6000

4000

2000

0 0

100

CAT4240—CHAPTER 16—1/11/2006—16:30—SRIDHAR—XML MODEL C – pp. 587–693

200 P (bar)

300

400

632

Solubility in Supercritical Carbon Dioxide

[P-65]

Phenanthrene (1) + Anthracene (2) Mixture 308

318

P (bar)

y1 x 10

104.4 138.7 173.2 206.9 242.2 104.4 138.7 173.2 206.9 242.2

6

y2 x 10

581 991 1290 1520 1610 243 965 1560 1930 2290

32.4 59.9 81.1 92.3 96.0 12.0 57.8 90.1 112.1 122.8

2500 2000 y x 106

T (K)

6

Phen 308 K Phen 318 K Anthr 308 K

1500 1000 500 0 100

Source: Kosal, E.; Holder, G. D. J. Chem. Eng. Data (1987), 32(2), 148-150.

150

200

250

P (bar) [P-66]

Phenanthrene (1) + Anthracene (2) Mixture T (K)

P (bar)

1) y1

x 106

1) y2

x 106

y x 106

106.2 600 32.76 139.3 1056 66.01 170.1 1318 85.30 206.2 1529 93.97 242.0 1665 101.90 1: Solubility was obtained from a mixture of phenanthrene and anthracene. Source: Liu, G.-T.; Nagahama, K. J. Chem. Eng. Japan (1997), 30(2), 293301.

2000

308.15

1000 Phenanthrene Anthracene

0 100

150

200 P (bar)

[P-67]

Phenanthrene (1) + Benzoic acid (2) Mixture 106

y1 x y2 x T (K) P (bar) 308 120 1020 1840 160 1360 2440 200 1630 2950 240 1870 3280 2050 3700 280 Source: Kurnik, R. T.; Reid, R. C. Fluid Phase Equil. (1982), 8(1), 93-105.

5000 y x 106

106

250

Phen BA

2500

0 100

200 P (bar)

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300

Solubility Data P

633

[P-68]

Phenanthrene (1) + Carbazole (2) Mixture y1 x

y2 x

106

595 832 1010 1150 1320

11.0 14.8 17.6 19.9 22.1

1600 y x 106

T (K) P (bar) 313.1 100 125 150 175 200

106

Source: Kwiatkowski, J.; Lisicki, Z.; Majewski, W. Ber. Bunsenges. Phys. Chem. (1984), 88(9), 865-869.

Phen Carbz

800

0 50

150

250

P (bar)

[P-69]

Phenanthrene (1) + 2,3-Dimethylnaphthalene (2) Mixture T (K)

P (bar)

y1 x 106

y2 x 106

Phen 308 K Phen 318 K 2,3-DMN 308 K 2,3-DMN 318 K

6000 y x 106

120 730 2890 160 1000 3560 200 1240 4230 240 1430 4430 1480 4500 280 318 120 530 2470 160 1190 4330 200 1710 5540 240 1960 5850 2330 6970 280 Source: Kurnik, R. T.; Reid, R. C. Fluid Phase Equil. (1982), 8(1), 93-105.

9000

308

3000

0 100

200

300

P (bar)

[P-70]

Phenanthrene(1) + 2,6-Dimethylnaphthalene(2) Mixture T (K)

P (bar)

y1 x

106

y2 x

106

Phen 2,6-DMN

y x 106

120 1060 2920 160 1490 3460 200 1850 4180 240 2050 4250 2070 4230 280 Source: Kurnik, R. T.; Reid, R. C. Fluid Phase Equil. (1982), 8(1), 93-105.

6000

308

3000

0 100

200 P (bar)

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300

634

Solubility in Supercritical Carbon Dioxide

[P-71]

Phenanthrene (1) + Naphthalene (2) Mixture 308

P (bar) 120 140 160 180 200 220 240 260 280

y1 x 106 1650 1920 2320 2540 2590 2900 2930 3010 3210

y2 x 106 14700 16200 17600 18400 18800 20800 21400 21300 21400

30000 Phen Naph

y x 106

T (K)

15000

0 100

Source: Kurnik, R. T.; Reid, R. C. Fluid Phase Equil. (1982), 8(1), 93-105.

200

300

P (bar)

[P-72]

1,10-Phenanthroline (C12H8N2; MW=180.21) 106

308 K 318 K 328 K 338 K 348 K

y x 106

S (g/L) yx T (K) P (bar) 308 101 0.3 100 152 0.5 150 203 0.6 160 253 0.7 200 304 0.9 240 1200 355 1.2 290 318 101 0.2 80 152 0.4 140 203 0.8 250 900 253 1.1 310 355 1.7 450 328 101 0.1 60 152 0.4 140 600 203 1.0 310 253 1.4 420 304 1.7 480 300 355 2.1 590 338 101 0.0 30 152 0.3 140 203 1.2 430 0 253 1.7 550 50 304 2.2 660 355 2.8 800 348 101 0.0 20 152 0.3 150 203 1.3 520 253 2.2 730 304 2.9 920 355 3.5 1040 Synonym: 4,5-Diazaphenanthrene Source: Shamsipur, M.; Ghiasvand, A. R.; Yamini, Y. J. Chem. Eng. Data (2004), 49(5), 1483-1486.

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150

250 P (bar)

350

Solubility Data P

635

[P-73]

Phenazine (C12H8N2; MW=180.21)

323

P (bar)

(mol%)

0 0 0 0 0 0 0

104.4 118.2 132.0 145.8 173.3 242.3 345.7

y x 106 37 101 207 225 519 1110 1290

Acetone 2.5 124 2.5 333 2.5 459 2.5 541 2.5 1000 2.5 1560 2.5 1870 Methanol 104.4 2.5 100 118.2 2.5 249 132.0 2.5 495 145.8 2.5 601 173.3 2.5 972 242.3 2.5 2020 345.7 2.5 4520 1: Cosolvent in CO2 on a solute-free basis. 104.4 118.2 132.0 145.8 173.3 242.3 345.7

4000

Pure CO2 Acetone (2.5%) Methanol (2.5%)

y x 106

T (K)

Cosolvent1)

2000

0 50

150

250

350

P (bar)

Synonyms: 9,10-Diazaanthracene; Dibenzopyrazine Source: Van Alsten, J. G.; Eckert, C. A. J. Chem. Eng. Data (1993), 38(4), 605-610.

Phenazopyridine (C11H11N5; MW=213.24) T (K) P (bar) 308 122 152 182 213 243 273 304 334 355 318 122 152 182 213 243 273

y x 106 15.0 20.5 26.3 32.2 38.4 44.4 47.8 51.0 56.8 14.5 21.3 31.0 41.8 51.6 61.8

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[P-74]

636

Solubility in Supercritical Carbon Dioxide

338

348

73.6 80.9 87.6 11.2 18.4 27.9 44.2 59.9 71.4 86.9 98.9 108.2 4.4 14.9 31.6 51.5 76.9 99.9 121.8 149.1 168.4 7.1 11.8 29.1 55.2 88.4 121.9 156.1 193.1 202.1

200

150 y x 106

328

304 334 355 122 152 182 213 243 273 304 334 355 122 152 182 213 243 273 304 334 355 122 152 182 213 243 273 304 334 355

308 K 318 K 328 K 338 K 348 K

100

50

0 100

200

300

400

P (bar)

Synonym: 2,6-Diamino-3-phenylazopyridine Source: Yamini, Y.; Arab, J.; Asghari-Khiavi, M. J. Pharm. Biomed. Anal. (2003), 32(1), 181-187.

Phenol (C6H6O; MW=94.11) T (K) P (bar) 100 333.15 125 150 175 200 225 250 275 300 325 350

y x 106 1140 5340 13600 23600 36000 40650 44620 54380 59900 67820 77300

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[P-75]

Solubility Data P

348.15

637

100 125 150 175 200 225 250 275 300 325 350 100 125 150 175 200 225 250 275 300 325 350

333.15 K 348.15 K 363.15 K

y x 106

1840 100000 3460 7350 16310 27920 36270 40200 55650 50000 62100 70500 80910 363.15 2040 3250 7490 11530 0 19790 50 27990 38660 51710 65390 77490 90640 Source: Julian, G.-G.; Molina, M. J.; Rodriguez, F.; Mirada, F. J. Chem. Eng. Data (2001), 46(4), 918-921.

150

250 P (bar)

Phenol (C6H6O; MW=94.11)

[P-76]

y x 106 3488 7314 9581 11270 12430 12800 13670 13900 14860 15020 15150 15890 16040 16360 15900 16710 16510 16700 16860 17550 17880 17930

50000 309.2 K 333.2 K

37500 y x 106

T (K) P (bar) 309.15 79.3 80.9 86.5 96.8 105.8 111.0 119.1 123.6 132.8 146.3 146.7 155.7 161.5 163.4 171.7 182.6 183.0 193.9 196.4 207.6 213.7 215.9

350

25000

12500

0 0

CAT4240—CHAPTER 16—1/11/2006—16:30—SRIDHAR—XML MODEL C – pp. 587–693

100

200 P (bar)

300

638

Solubility in Supercritical Carbon Dioxide

221.7 18220 234.2 18340 249.4 18160 333.15 122.7 6496 127.0 12330 145.7 18590 146.1 18720 152.6 18040 160.3 21950 168.3 22090 177.5 28300 183.0 29010 186.8 30650 192.5 31580 204.0 31460 211.1 38900 221.8 36440 232.9 44600 241.8 46600 Source: Van Leer, R. A.; Paulaitis, M. E. J. Chem. Eng. Data (1980), 25(3), 257-259.

[P-77]

Phenol Blue (C14H14N2O; MW=226.27)

313

323

333

P (bar) 93.5 94.6 96.0 97.4 99.1 101.0 103.4 104.7 108.2 111.3 112.5 113.5 114.4 116.4 116.9 118.5 120.3 122.6 126.6 123.4 124.5 126.2 128.9 130.6

S x 103 (g/L) 1.59 2.37 3.40 4.58 6.16 7.77 9.18 10.52 1.20 2.49 3.09 3.67 4.23 5.04 5.77 6.48 7.92 9.30 11.81 2.48 3.21 4.37 5.52 7.09

y1) x 106 0.54 0.79 1.10 1.45 1.90 2.35 2.72 3.08 0.48 0.93 1.12 1.31 1.49 1.73 1.97 2.17 2.59 2.98 3.66 1.03 1.31 1.75 2.12 2.68

6 313 K 323 K 333 K 343 K

4 y x 106

T (K)

2

0 80

CAT4240—CHAPTER 16—1/11/2006—16:31—SRIDHAR—XML MODEL C – pp. 587–693

120 P (bar)

160

Solubility Data P

639

132.2 8.39 3.10 135.7 10.18 3.63 138.5 11.58 4.02 141.1 13.01 4.42 343 125.4 1.84 0.94 127.6 2.19 1.09 129.7 2.89 1.39 133.3 3.79 1.73 137.4 5.73 2.49 138.8 6.83 2.91 141.7 8.44 3.49 144.3 9.80 3.93 146.5 11.07 4.35 148.2 12.36 4.78 13.61 5.23 148.8 1: Obtained by digitizing the graph in the original article. Synonym: N,N-Dimethylindoaniline Source: Sasaki, T.; Takeishi, H.; Yoshida, Z. J. Supercrit. Fluids (1999), 15, 23-31.

Phenol Blue (C14H14N2O; MW=226.27) P (bar)

308.15

100.8 121.0 150.5 199.6 300.2

Cosolvent (mol%) 0.0 0.0 0.0 0.0 0.0 Acetone 3.5 3.5 3.5 3.5 3.5 5.25 5.25 5.25 5.25 5.25

y x 106

150 None 3.50% 5.25%

13.1 17.2 24.3 32.4 42.7

100.8 32.5 120.1 44.6 150.7 44.6 200.0 66.0 298.2 88.0 100.6 64.6 120.9 80.2 151.2 102.0 200.2 111.0 146.0 299.9 Synonym: N,N-Dimethylindoaniline Source: Kim, S.; Johnston, K. P. AIChE. J. (1987), 33(10), 1603-1611.

100 y x 106

T (K)

[P-78]

50

0 50

CAT4240—CHAPTER 16—1/11/2006—16:31—SRIDHAR—XML MODEL C – pp. 587–693

150

250 P (bar)

350

640

Solubility in Supercritical Carbon Dioxide

[P-79]

Phenylacetic acid (C8H8O2; MW=136.15)

308.2 K 318.2 K

y x 106

T (K) P (bar) y1) x 106 308.2 83.5 1000 90.5 2200 95.5 2500 98.5 2400 20000 99.0 2500 102.5 2900 110.5 3800 111.5 4000 15000 134.5 4900 142.5 5700 161.0 6500 10000 166.5 6500 174.0 6900 175.0 7400 184.0 7700 5000 318.2 93.0 400 109.0 2100 122.0 5600 0 131.0 7300 50 138.0 8800 142.0 9000 152.0 10900 171.0 14300 191.0 17500 1: The unit of solubility in the source table was corrected from mole fraction to mol% to be consistent with the graphed data in the same article. Synonyms: Benzeneacetic acid; Phenylethanoic acid Source: Wells, P. A.; Chaplin, R. P.; Foster, N. R. J. Supercrit. Fluids (1990), 3(1), 8-14.

L-Phenylalanine

100

150 P (bar)

[P-80]

(C9H11NO2; MW=165.19)

T (K) P1) (bar) S1) (μg/Nl2))

200

y3) x 106

0.06

300 0.230 0.0310 500 0.279 0.0376 1000 0.382 0.0515 0.04 1500 0.424 0.0571 0.430 0.0580 2000 1: Obtained by digitizing the graph in the 0.02 original article. 2: Nl means "Normliter," which is one liter 0 at 273.15 K and 1 atm. 3: Calculated from S. Synonyms: (S)-2-Amino-3-phenylpropanonic acid; 3Phenyl-L-alanine Source: Stahl, E.; Schilz, W. Chem. Ing. Tech. (1978), 50(7), 535-537.

y x 106

313.15

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1000 P (bar)

2000

Solubility Data P

641

[P-81]

3-Phenyl-1-propanol (C9H12O; MW=136.19)

y x 106

y x 106 T (K) P (bar) S (g/L) 313 80 0.58 550 8000 100 8.08 3650 125 13.87 5390 150 17.12 6240 6000 175 20.49 7160 200 22.20 7520 323 80 0.18 220 4000 100 1.46 990 125 5.93 2740 150 8.85 3600 2000 175 11.47 4360 200 13.60 4940 333 80 0.07 110 0 100 0.35 330 125 1.95 1140 50 150 4.16 1960 175 6.17 2600 200 7.92 3120 Synonym: Benzenepropanol Source: Medina, L.; Bueno, J. L. J. Chem. Eng. Data (2000), 45(2), 298-300.

313 K 323 K 333 K

150 P (bar)

[P-82]

Phenytoin (C15H12N2O2; MW=252.27) T (K)

P (bar)

Menthol1)

y x 106

1500

318.13

y x 106

96 0 0.8 129 0 1.6 196 0 3.0 96 saturated 561.0 129 saturated 829.0 196 saturated 1302.0 1: A cosolvent that is fully saturated in CO2. Synonyms: 5-5-Diphenyl-2,-4imidazolidinedione; 5,5-diphenylhyclantoin. Source: Thakur, R., Ph.D. Dissertation, Auburn University, Auburn, Alabama, 2006.

250

1000 Pure CO2 With Menthol

500 0 50

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150 P (bar)

250

642

Solubility in Supercritical Carbon Dioxide

[P-83]

Phthalic anhydride (C8H4O3; MW=148.12)

308.15

P (bar) 120 150 200 300 350 200 200 300 300

Cosolvent (mol%) 0.0 0.0 0.0 0.0 0.0 Acetone 3.5 3.5 3.5 3.5

y x 106 1420 1530 2270 3140 3450

8000 CO2 Acetone

y x 106

T (K)

4290 4310 5460 5210

4000

0 0

100

Synonyms: 1,3-Isobenzofurandione; 1,3Phthalandione Source: Dobbs, J. M.; Wong, J. M.; Lahiere, R. J.; Johnston, K. P. Ind. Eng. Chem. Res. (1987), 26(1), 56-65.

200 P (bar)

300

[P-84]

Picric acid (C6H3N3O7; MW=229.10) S (g/L) 1.05 1.40 2.04 2.84 3.35 3.84 4.54 5.19 5.76 6.44 0.98 1.66 2.14 2.93 3.49 4.19 5.12 5.85 6.58 7.77 0.36 1.24 1.89 2.67 3.67 4.62 5.72 6.91 7.88 8.94

x

106 262 322 449 608 698 782 908 1020 1120 1230 282 417 505 660 760 888 1060 1190 1320 1530 130 348 480 637 841 1030 1230 1460 1630 1820

3000 308 K 318 K 328 K 338 K 348 K

2000 y x 106

T (K) P (bar) 308 121.6 162.1 202.6 243.2 283.7 324.2 364.8 405.3 445.8 486.4 318 121.6 162.1 202.6 243.2 283.7 324.2 364.8 405.3 445.8 486.4 328 121.6 162.1 202.6 243.2 283.7 324.2 364.8 405.3 445.8 486.4

y1)

400

1000

0 0

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200

400 P (bar)

600

Solubility Data P 338

348

121.6 162.1 202.6 243.2 283.7 324.2 364.8 405.3 445.8 486.4 121.6 162.1 202.6 243.2 283.7 324.2 364.8 405.3 445.8 486.4

643 0.47 1.18 2.23 0.30 3.86 5.17 6.28 7.72 9.26 10.66 0.04 0.66 1.80 2.84 4.02 5.36 6.84 8.63 10.40 12.21

227 380 617 771 930 1200 1410 1690 1980 2240 22 243 546 777 1030 1310 1600 1970 2310 2650

1: y value for 308 K and 243.2 bar in the original article was misprinted and thus corrected based on S. Synonym: 2,4,6-Trinitrophenol Source: Shamsipur, M.; Fat'hi, M. R.; Yamini, Y.; Ghiasvand, A. R. J. Supercrit. Fluids (2002), 23(3), 225-231. [P-85]

a -Pinene (C10H16; MW=136.23) 106

P (bar) y x 18000 72.6 1700 75.1 2000 75.9 2200 78.2 2600 78.6 3200 12000 79.3 3400 323 79.1 4200 83.9 4600 88.8 5800 91.8 7600 6000 93.0 7800 333 71.5 2600 79.9 3000 86.9 3700 91.9 4000 0 95.4 6200 60 104.0 8100 108.3 13400 109.3 17000 Synonyms: 2-Pinene; 2,6,6-Trimethylbicyclo[3.1.1]hept-2-ene Source: Akgun, M.; Akgun, N. A.; Dincer, S. J. Supercrit. Fluids (1999), 15, 117-125.

313 K 323 K 333 K

y x 106

T (K) 313

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80

100 P (bar)

120

644

Solubility in Supercritical Carbon Dioxide

[P-86]

a -Pinene (C10H16; MW=136.23) S1,2)(g/L)

y3)

106

y x 106

x T (K) P1) (bar) 30000 313 80 0.039 6920 10400 100 0.059 17400 150 0.099 20000 25600 250 0.147 1960 333 80 0.011 8860 100 0.050 10000 12000 150 0.068 250 0.094 16500 0 1: Obtained by digitizing the graph in the original article. 50 2: Solubility is based on 1 liter of CO2 at 293.15 K and 1 atm. 3: Calculated from S. Synonyms: 2-Pinene; 2,6,6-Trimethylbicyclo[3.1.1] hept-2-ene Source: Francisco, J. C.; Sivik, B. J. Supercrit. Fluids (2002), 23(1), 11-19.

a -Pinene (C10H16; MW=136.23) T (K) P (bar) 313.15 46.3 47.3 49.0 49.3 52.7 52.7 53.0 53.6 57.3 58.0 58.9 59.9 60.7 64.9 65.2 66.9 66.9 68.6 69.1 70.5 71.6 72.6 73.0 73.4 73.7 74.4 74.8 75.4 75.5

yx

106 1350 1420 1160 1430 1450 1420 1510 1540 1950 1960 2180 2000 2060 2390 2370 2210 2270 2750 2750 2310 2100 2780 2980 3400 3720 3410 4130 4470 3800

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313 K 333 K

150

250

P (bar)

[P-87]

Solubility Data P

645

323.15

313.15 K 323.15 K 328.15 K

y x 106

33.6 2400 33.6 2620 38.6 2180 42.3 2130 42.7 2270 48.6 2270 51.5 2570 60.4 2530 68.5 3140 76.7 4220 81.5 5780 81.7 6100 86.3 7320 86.4 7460 88.5 8150 88.7 8010 90.4 9510 20000 90.5 9310 91.6 10420 91.6 9880 92.0 10820 328.15 32.5 2620 40.0 2920 40.1 2820 10000 51.9 2970 52.5 3080 61.3 3270 61.6 3350 69.1 3480 69.6 3630 75.3 4700 80.0 5190 0 81.0 5470 30 81.5 5860 85.6 6530 89.5 7180 89.8 7200 92.0 8260 92.9 9170 96.0 15040 97.1 12350 97.1 15700 97.5 17230 Synonyms: 2-Pinene; 2,6,6-Trimethylbicyclo [3.1.1]hept-2-ene Source: Richter, M.; Sovova, H. Fluid Phase Equil. (1993), 85, 285-300.

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70 P (bar)

110

646

Solubility in Supercritical Carbon Dioxide

[P-88]

a -Pinene (C10H16; MW=136.23) P (bar)

T (K)

yx

106

61.4 295.85 10410 298.15 2820 300.55 1880 40000 300.55 1840 300.65 1630 303.15 1340 303.55 1390 305.15 1490 313.15 1860 323.15 2620 20000 328.15 3300 335.15 4240 76.5 311.05 31930 311.75 16400 313.15 9500 315.85 5230 317.85 4530 0 317.85 4580 321.45 4200 290 321.45 4130 323.15 3900 328.15 4470 335.15 4650 335.25 4930 Synonyms: 2-Pinene; 2,6,6-Trimethylbicyclo [3.1.1]hept-2-ene Source: Richter, M.; Sovova, H. Fluid Phase Equil. (1993), 85, 285-300.

y x 106

61.4 bar 76.5 bar

310

Piroxicam (C15H13N3O4S; MW=331.35)

[P-89] 50 312.5 K 331.5 K

y x 106

y x 106 T (K) P (bar) 312.5 100 4.5 130 12.1 160 19.2 190 29.2 220 43.3 331.5 130 3.7 160 12.6 190 23.1 220 38.9 Synonym: 4-Hydroxy-2-methyl-N-2pyridinyl-2H-1,2-benzothiazine-3carboxamide 1,1-dioxide Source: Macnaughton, S. J.; Kikic, I.; Foster, N. R.; Alessi, P.; Cortesi, A.; Colombo, I. J. Chem. Eng. Data (1996), 41(5), 1083-1086.

330

T (K)

25

0 50

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150 P (bar)

250

Solubility Data P

647

[P-90]

Platinum bis(acetylacetonate) (C10H14O4Pt; FW=393.29)

313.2 353.3 373.2 393.1 423.2

97.1 146.7 195.2 244.8 294.3 196.0 196.0 196.0 196.0 196.0

15.0 26.0 29.7 31.8 37.2 30.0 19.0 30.0 31.0 29.0

1: T at 196 bar, P at 313.0 K, and y are those obtained by digitizing the graph in the original article. Synonyms: Bis(2,4-pentanedionato) platinum; Platinum(II) acetylacetonate Source: Yoda, S.; Hasegawa, A.; Suda, H.; Uchimaru, Y.; Haraya, K.; Tsuji, T.; Otake, K. Chem. Mater. (2004), 16(12), 2363-2368.

50 y x 106

313.0

y1) x 106

25 0 50

150

250

350

400

450

P (bar) 50 y x 106

T1) (K) P1) (bar)

25 0 300

350

T (K)

[P-91]

Poly(1,1-dihydroperfluorooctyl acrylate)1) (MW=1.0 x 106) w2) x 106 800 5200 10000 800 5200 10000 800 5200 10000 800 5200 10000 800 5200 10000 800 5200 10000

12000

303 K 313 K 323 K 328 K 333 K 338 K 343 K 353 K

8000 w x 106

T (K) P2) (bar) 303 126 135 138 313 150 169 173 323 186 202 205 328 200 216 219 333 217 231 233 338 237 244 248

4000

0 50

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150 P (bar)

250

648

Solubility in Supercritical Carbon Dioxide

343

251 800 259 5200 261 10000 353 279 800 283 5200 287 10000 1: Usually abbreviated as poly(FOA). 2: Obtained by digitizing the graph in the source article. Source: Hsiao, Y.-L.; Maury, E. E.; DeSimone, J. M.; Mawson, S.; Johnston, K. P. Macromolecules (1995), 28 (24), 8159-8166.

Polyethylene glycol (PEG1000, PEG2000, PEG6000) T (K)

P (bar)

Ethanol1,2) (wt%)

w2) x 106

[P-92]

500000 PEG 1000 PEG 2000 PEG 6000

w x 106

PEG 1000 (Mw=1000) 313.15 160 14.0 190000 22.1 264000 30.9 416000 PEG 2000 (Mw=2000) 0.8 56000 250000 6.8 100000 22.5 172000 PEG 6000 (Mw=7500) 5.2 22000 18.5 58000 24.7 100000 0 1: Cosolvent concentration in the entire 0 fluid mixture. 2: Obtained by digitizing the graph in the source article. Source: Mishima, K.; Tokuyasu, T.; Matsuyama, K.; Komorita, N.; Enjoji, T.; Nagatani, M. Fluid Phase Equil. (1998), 144, 299-305.

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10 20 Ethanol (wt%)

30

Solubility Data P

649

[P-93]

Polyethylene glycol (PEG 6000; Mw=7500) T (K)

P (bar)

Cosolv1,2) (wt%)

w2) x 106

300000 Ethanol Toluene

w x 106

Ethanol 313 150 18.3 60000 200000 24.7 102000 28.3 160000 29.2 191000 100000 Toluene 9.4 72000 10.4 84000 11.4 113000 0 14.3 254000 0 1: Cosolvent concentration in the entire fluid mixture. 2: According to the authors the concentraion data for cosolvent and PEG in the source graph are wrong. The data shown here are directly from the authors. Source: Mishima, Kenji; Y, S.; Ito, M.; Ezawa, M.; Tanabe, D. Solvent Extr. Res. Dev., Japan, (1999), 6, 176-181.

10

20

30

Cosolvent (wt%)

[P-94]

Poly(ethylene glycol-block-propylene glycol)1) T (K) P2) (bar) w2) x 106 EO6-PO21-EO6 439 7360 442 7280 448 7490 450 7620 450 7680 453 7810 PO9-EO23-PO9 337 351 356 367 370 379 384 390 395 403 409 412 414

6500 6690 7010 7280 7580 7790 7950 8190 8380 8690 8990 9070 9090

10000 EO6-PO21-EO6 PO9-EO23-PO9 PO15-EO10-PO15 EO-PO16-EO

8000 w x 106

295.4

6000

4000 100

200

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300 P (bar)

400

500

650

Solubility in Supercritical Carbon Dioxide

PO15-EO10-PO15 243 4200 252 4500 257 4690 263 4880 265 5110 268 5300 271 5380 276 5490 279 5830 282 5700 287 5910 EO-PO16-EO 149 5110 158 5590 166 6080 171 6480 177 6900 177 7470 1: Block copolymer of ethylene oxide and propylene oxide. 2: Obtained by digitizing the graph in the original article. Source: Drohmann, C.; Beckman, E. J. J. Supercrit. Fluids (2002), 22, 103–110.

[P-95]

Poly(ethylene glycol) dimethylether1) (bar)

w2)

x

106

Mw=500 295.4 101 21800 110 26700 120 31500 1: Both end groups of the polymer are dimethyl ethers. 2: Obtained by digitizing the graph in the original article. Source: Drohmann, C.; Beckman, E. J. J. Supercrit. Fluids (2002), 22, 103-110.

40000 w x 106

T (K)

P2)

10000 100

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110 P (bar)

120

Solubility Data P

651

[P-96]

Poly(ethylene glycol) diol1) T (K) P2) (bar)

w2) x 106

Mw=200 12100 13200 14400 15200 16300 17100 17500 Mw=300 175 8300 20000 182 8810 194 9450 203 10000 214 10500 15000 222 10900 233 11500 240 11800 246 12200 10000 249 12500 Mw=400 203 8170 220 8680 5000 230 9450 250 10000 260 10700 0 274 11400 288 11900 100 297 12300 304 12700 313 13300 Mw=600 220 4760 241 5340 262 5790 274 6240 288 6690 296 7070 310 7520 318 7850 1: Both end groups of this polymer are hydroxyl groups. 2: Obtained by digitizing the graph in the original article. Source: Drohmann, C.; Beckman, E. J. J. Supercrit. Fluids (2002), 22, 103-110. 146 164 184 197 218 234 241

w x 106

295.4

Mw=200 Mw=300 Mw=400 Mw=600

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200 P (bar)

300

652

Solubility in Supercritical Carbon Dioxide

Poly(ethylene glycol) monomethylether1) P2) (bar)

295.4

295.4

295.4

97 101 103 109 111 122 130 132 136 148 160 166 174 182 186 191 191 201 203 211 213 215 221 231 239 247 251 259 266 270 276 280 280 231 239 255 266 274 282 286 288 300

w2) x 106 Mw=350 13100 11000 15100 18800 20800 23600 26100 27500 Mw=550 5920 6430 7030 7460 7980 8410 9010 10100 11900 12700 10600 11200 13600 11700 14300 15100 16000 16500 17200 17800 18400 19100 19700 20200 20800 Mw=750 9440 10100 10600 11200 11600 12200 12500 15200 13200

30000

w x 106

T (K)

[P-97]

20000

10000 Mw=350 Mw=550 Mw=750 Mw=1000

0 0

100

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200

300

P (bar)

400

500

Solubility Data P

300 302 306 306 308 312 312 318 328 339 347 355 363 369 373 381 383 389 393 397 401 401 407

16100 13600 13600 14200 17000 14500 14800 17500 18300 18700 19600 20200 20700 21200 21500 22100 22700 23000 23600 23800 24300 24700 25300 Mw=1000 295.4 164 3860 180 4200 182 4460 193 4890 197 5150 209 5490 215 5830 221 6090 257 10600 266 11200 274 11600 276 12200 294 12600 300 13400 304 13600 1: This polymer has a methyl ether group at one end and a hydroxyl group at the other end. 2: Obtained by digitizing the graph in the original article. Source: Drohmann, C.; Beckman, E. J. J. Supercrit. Fluids (2002), 22, 103–110.

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653

654

Solubility in Supercritical Carbon Dioxide

[P-98]

Poly(ethylene glycol-ran-propylene glycol)1) T (K) P2) (bar)

w2) x 106

215 218 221 227 227 227 227 230 230 233 242 242 245 255 264 267 267 267 267 267 276 279 279 282 288 294 297 297 297 306 306 312 315

Mw= 970 Mw=1700

w x 106

Mw=970 7790 8100 8400 9150 9380 9830 10100 8780 8850 25000 10500 10700 11000 11100 14400 11600 11300 12000 15000 12200 12400 15100 15800 17200 17700 16300 5000 18400 19400 150 20100 20600 21500 22100 22900 23600 24200 Mw=1700 448 7870 448 8020 448 8170 448 8250 448 8400 1: Random copolymer with an ethylene glycol content of approximately 50 wt%. 2: Obtained by digitizing the graph in the original article. Source: Drohmann, C.; Beckman, E. J. J. Supercrit. Fluids (2002), 22, 103–110. 295.4

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250

350 P (bar)

450

Solubility Data P

655

[P-99]

Poly(ethyl vinyl ether)1) (Mw=1500) (bar) 289 298 304 305 310 321 307 342 346 351

w2)

x

106

16000

11400 11900 12300 12700 13100 13500 13900 14300 14600 15000

w x 106

T (K) 295.4

P2)

13000

10000 280

320

360

P (bar)

1: A low molecular weight polymer. (Lutanol A25) from BASF with 20 repeat units. 2: Obtained by digitizing the graph in the original article. Source: Drohmann, C.; Beckman, E. J. J. Supercrit. Fluids (2002), 22, 103–110.

[P-100]

Poly(FOEMA-co -PPGMA)1)

338.15

P (bar)

330

MMA (g/L)

S3) (g/L)

FOEMA 5) = 52 wt% (Mn=74,000) 0 1.6 30 1.8 60 5.1 90 9.2 150 20.8 200 50.8 5) FOEMA = 67 wt% (Mn=92,000) 0 3.0 30 5.5 60 14.8 90 31.4 5) FOEMA5) = 75 wt% 0 4.0 30 7.4 60 16.2 90 51.7

w4) x 106

1900 2100 6000 10800 24100 58100

3600 6600 17500 36800 4800 8800 19200 60400

FOEMA = 52 wt% FOEMA = 67 wt% FOEMA = 75 wt% FOEMA = 100 wt%

90000

60000 w x 106

T(K)

2,3)

30000

0

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0

50

100

150

MMA (g/L)

200

656

Solubility in Supercritical Carbon Dioxide

FOEMA5) = 100 wt% 0 6.0 7200 30 10.1 12000 60 20.5 24200 90 37.6 44000 150 61.2 70500 1: FOEMA: 2-(Perfluorooctyl)ethyl methacrylate. PPGMA: Poly(propylene glycol) methacrylate. 2: Cosolvent in CO2. 3: Obtained by digitizing the graph in the original article. 4: Calculated from S assuming that MMA and the polymer density of 1 g/mL. 5: FOEMA content in the copolymer. 6: Number average molecular weight (Mn) is not known for these polymers. Source: Ding, L.; Olesik, S. V. Macromolecules (2003), 36(13), 4779-4785.

[P-101]

Poly(b-hydroxybutyrate) (MW=800,000)

318

328

P (bar) S (g/L) 122 0.54 152 0.68 182 1.07 213 1.13 243 1.46 274 1.58 304 1.86 334 1.96 355 2.41 122 0.31 152 0.58 182 1.06 213 1.37 243 1.67 274 1.98 304 2.11 334 2.43 355 2.65 122 0.23 152 0.59 182 1.05 213 1.44 243 1.79 274 2.38 304 2.69 334 2.98 355 3.49

wx

700 830 1260 1290 1630 1720 2000 2070 2520 470 780 1340 1660 1960 2260 2360 2670 2880 460 900 1450 1870 2230 2860 3150 3420 3950

12000

8000

308 K 318 K 328 K 338 K 348 K

w x 106

T (K) 308

106

4000

0 100

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200

300 P (bar)

400

Solubility Data P

338

657

122 152 182 213 243 274 304 334 355

0.18 0.43 1.01 1.43 2.23 2.78 3.18 3.69 4.77

450 770 1540 2010 2960 3540 3920 4420 5630

348 122 152 182 213 243 274 304 334 355

0.15 0.29 0.69 1.49 2.65 3.65 4.71 5.33 8.01

460 610 1180 2290 3770 4930 6100 6700 9880

Source: Khosravi-Darani, K.; Vasheghani-Farahani, E.; Yamini, Y.; Bahramifar, N. J. Chem. Eng. Data (2003), 48(4), 860-863.

Polymers

[P-102]

Polymer

T (K)

P (bar)

PEG4000 PMMA15000 PMMA90000 PMMA120000 PS-b-(PMMA-co-PGMA) Poly(styrene) Bisphenol A-type epoxy resin Poly(oxyalkylene) alkylphenyl ether

308

160

308 308

160 160

308 308

160 160

308 308 308

160 160 160

Ethanol (wt%) 35 35 35 35 35 35 35 35

1: Mass fraction solubility on a polymer-free basis. Source: Matsuyama, K.; Mishima, K.; Umemoto, H.; Yamaguchi, S. Environ. Sci. Tech. (2001), 35(20), 4149-4155.

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w1) x 106 129000 12000 5100 3200 202000 0 22100 161000

658

Solubility in Supercritical Carbon Dioxide

Poly(methyl methacrylate) (Mn = 540,000)

313

313

313

180

180

180

[P-103]

w x 106

Acetone 7.0 14.5 26.6 31.8 Ethanol 7.7 13.0 26.9 31.5 CH 2 Cl 2 15.8 22.0 38.3 43.6

300

160 220 70 30

w x 106

T (K)

Cosolvent P(bar) (wt%)

10 10 20 10

200

10 0

Acetone Ethanol CH2Cl2

0

20 80 200 250

0

20

40

60

Cosolvent (wt%)

Source: Domingo, C.; Vega, A.; Fanovich., M. A.; Elvira, C.; Subra, P. J. Appl. Polym. Sci.(2003), 90(13), 3652-3659.

[P-104]

Poly(propylene glycol) diol1)

295.4

91 106 112 114 126 127 129 131 133 133 134 137 136 91 107 112 113 127 129 130 131 131

w2) x 106 Mw=400 9030 10200 11800 13300 14300 15400 15900 16800 17300 18000 18700 19600 20300 Mw=425 8900 10200 11900 13300 14300 15300 15900 16700 17200

30000

Mw=400 Mw=425 Mw=725 Mw=1000 Mw=2000

20000 w x 106

T (K) P2) (bar)

10000

0 0

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100

200 P (bar)

300

Solubility Data P

133 133 137 136

659

189 196

17900 18700 19700 20200 Mw=725 8680 10800 18700 20200 21900 23200 24800 26200 26700 27700 Mw=1000 7710 8460 9130 9870 10500 11100 11900 Mw=2000 5920 6220

203

6590

212 214 217 224 231 234 234

7040 7260 7340 7790 8080 8230 8530

239

8900

72 86 97 98 101 102 112 111 112 113 171 171 182 189 198 206 213

1: Both end groups of this polymer are hydroxyl groups. 2: Obtained by digitizing the graph in the original article. Source: Drohmann, C.; Beckman, E. J. J. Supercrit. Fluids (2002), 22, 103–110.

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660

Solubility in Supercritical Carbon Dioxide

[P-105]

Poly(propylene glycol) monobutylether1) (Mw = 1000)

w x 106

T (K) P2) (bar) w2) x 106 298.15 115 9420 128 10300 30000 133 11300 140 12400 147 13500 153 14900 20000 174 18300 176 19600 190 21200 195 22600 10000 199 24100 201 25800 203 27200 343.15 300 7590 0 306 10200 100 309 15400 309 20200 311 22400 311 25000 1: This polymer has a butyl ether group at one end and a hydroxyl group at the other end. 2: Obtained by digitizing the graph in the original article. Source: Drohmann, C.; Beckman, E. J. J. Supercrit. Fluids (2002), 22, 103–110.

298.15 K 343.15 K

200 P (bar)

[P-106]

Poly(propylene glycol) monomethylether1)

295.4

116 127 135 142 147 153 174 178 188 197 197 202 202 164 170 181 188 197

w2) x 106 Mw=1000 9430 10300 11300 12300 13500 14900 18200 19600 21300 22600 24200 25800 27200 Mw=1200 9620 10300 10900 11500 12000

30000

20000 w x 106

T (K) P2) (bar)

300

10000 Mw=1000

0 100

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Mw=1200

200 P (bar)

300

Solubility Data P

197 201 205 207 213 216 223 228 236 240 243 248 249 253 259 263 266 266 271 271

661

12600 13200 13700 15400 14100 16200 17200 17800 18700 19400 20100 20800 21600 22200 22700 23200 23800 24600 24700 25600

1: This polymer has a methyl ether group at one end and a hydroxyl group at the other end. 2: Obtained by digitizing the graph in the original article. Source: Drohmann, C.; Beckman, E. J. J. Supercrit. Fluids (2002), 22, 103–110.

Poly(tetrafluoroethylene-co-vinyl acetate) (Mw=166,000; 156,000; 140,000 from the top)

80.7

P1) (bar) 527 520 525 521 524 523 545 548 546 538 527

120000

w1) x 106 30400 40300 50000 59900 70200 80100 10300 20300 30200 39900 50200

73.5 mol% 80.7 mol% 88.4 mol% 100 mol%

80000 w x 106

VAc in T (K) polymer (mol%) 298.15 73.5

[P-107]

40000

0 450

550 P (bar)

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650

662

Solubility in Supercritical Carbon Dioxide

521 59900 512 70500 503 79700 490 89800 478 100000 88.4 542 20000 539 30400 535 40100 526 50000 521 60100 511 73500 100.0 637 30400 624 40500 619 50000 616 60100 1: Obtained by digitizing the graph in the original article. Source: Baradie, B.; Shoichet, M. S.; Shen, Z.; McHugh, M. A.; Hong, L.; Wang, Y.; Johnson, J. K.; Beckman, E. J.; Enick, R. M. Macromolecules (2004), 37(20), 7799-7807.

[P-108]

Poly(vinyl butyral) T (K) P (bar) y x 106 348.15 400 0.008 Source: Shende, R. V.; Lombardo, S. J. J. Supercrit. Fluids (2002), 23(2), 153-162.

[P-109]

Prednisolone (C21H28O5; MW=360.44) yx

0.004 0.028 0.067 0.093 0.117 0.170 0.255 0.350 0.413 0.728 0.001 0.004 0.012 0.027 0.039 0.047 0.066 0.098 0.122 0.131

0.8 308.15 K 328.15 K 373.15 K

0.6 y x 106

T (K) P (bar) 308.15 82.4 99.0 113.8 129.4 146.1 160.8 177.5 196.1 210.8 226.5 328.15 82.4 99.0 113.8 129.4 146.1 160.8 177.5 196.1 210.8 226.5

106

0.4

0.2

0.0 50

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150 P (bar)

250

Solubility Data P

663

373.15

113.8 0.009 129.4 0.011 146.1 0.015 160.8 0.033 177.5 0.054 196.1 0.070 210.8 0.086 226.5 0.099 Synonyms: 1,2-Dehydrohydrocortisone; 11b,17,21Trihydroxy-1,4-pregnadiene-3,20-dione Source: Dean, J. R.; Kane, M.; Khundker, S.; Dowle, C.; Tranter, R. L.; Jones, P. Analyst (1995), 120(8), 2153-2157.

[P-110]

Prednisone (C21H26O5; MW=358.43)

308.15 K 328.15 K 373.15 K

y x 106

y x 106 T (K) P (bar) 308.15 82.4 0.007 99.0 0.026 113.8 0.051 129.4 0.079 146.1 0.118 160.8 0.154 0.9 177.5 0.288 196.1 0.485 210.8 0.659 226.5 0.893 0.6 328.15 82.4 0.001 99.0 0.001 113.8 0.006 129.4 0.016 0.3 146.1 0.039 160.8 0.080 177.5 0.126 196.1 0.266 0.0 210.8 0.427 226.5 0.637 50 373.15 113.8 0.005 129.4 0.014 146.1 0.034 160.8 0.079 177.5 0.112 196.1 0.191 210.8 0.313 226.5 0.588 Synonyms: 1,2-Dehydrocortisone; 17,21-Dihydroxy1,4-pregnadiene-3,11,20-trione Source: Dean, J. R.; Kane, M.; Khundker, S.; Dowle, C.; Tranter, R. L.; Jones, P. Analyst (1995), 120(8), 2153-2157.

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150 P (bar)

250

664

Solubility in Supercritical Carbon Dioxide

[P-111]

Procaine (C13H20N2O2; MW=236.31) T (K)

P (bar)

yx

106

298

298 K 308 K 318 K

y x 106

69 58.2 75 61.0 84 61.3 101 64.2 124 72.0 151 88.2 175 93.7 150 192 97.5 225 103.0 252 103.0 308 94 83.1 100 85.5 122 89.7 100 149 100.8 169 108.0 198 125.0 222 139.0 249 153.0 318 80 71.4 50 85 71.5 0 90 73.1 94 77.2 109 95.4 125 109.0 150 131.0 174 143.0 195 150.0 245 165.0 Synonym: 2-(Diethylamino)ethyl-4-aminobenzoate Source: Weinstein, R. D.; Muske, K. R.; Moriarty, J.; Schmidt, E. K. J. Chem. Eng. Data (2004), 49(3), 547-552.

Progesterone (C21H30O2; MW=314.46) T (K)

P (bar)

308.2

104.7 121.7 140.3 155.8 174.4 190.9 208.6 225.2 243.6

N2O1) (vol %) 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0

y x 106 99.2 139.4 213.3 318.8 355.7 474.7 503.8 558.2 593.4

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100

200

300

P (bar)

[P-112]

Solubility Data P

800

CO2 308.2 K CO2 313.2 K CO2 318.2 K CO2 328.2 K w/N2O 308.2 K w/N2O 328.2 K

600

y x 106

93.8 10.0 52.4 106.1 10.0 127.1 122.5 10.0 166.0 138.4 10.0 266.3 156.6 10.0 321.7 173.2 10.0 384.7 190.9 10.0 497.8 208.6 10.0 509.7 225.8 10.0 593.0 241.4 10.0 621.8 313.2 105.9 0.0 50.9 122.4 0.0 119.0 141.8 0.0 183.3 156.6 0.0 237.8 176.8 0.0 374.6 191.1 0.0 486.7 208.6 0.0 554.1 226.1 0.0 602.6 243.6 0.0 635.9 318.2 106.2 0.0 47.5 124.7 0.0 102.9 140.3 0.0 178.6 161.4 0.0 284.3 174.7 0.0 377.2 191.9 0.0 471.4 209.0 0.0 582.9 225.9 0.0 611.4 243.4 0.0 681.7 328.2 108.5 0.0 10.9 121.7 0.0 16.9 142.8 0.0 64.3 159.6 0.0 174.1 174.5 0.0 277.6 192.0 0.0 489.8 209.0 0.0 576.3 225.8 0.0 656.3 243.3 0.0 738.6 109.8 10.0 15.6 121.9 10.0 19.3 142.6 10.0 104.4 156.4 10.0 167.4 175.0 10.0 314.5 190.7 10.0 494.2 209.6 10.0 609.2 225.9 10.0 705.6 242.6 10.0 745.2 1. Cosolvent in CO2. Synonym: Pregn-4-ene-3,20-dione Source: Kosal, E.; Lee, C. H.; Holder, G. D. J. Supercrit. Fluids (1992), 5(3), 169-179.

665

400

200

0 50

100

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150 P (bar)

200

250

666

Solubility in Supercritical Carbon Dioxide

[P-113]

Progesterone (1) + Cholesterol (2) Mixture1) P (bar)

y1 x 106

y2 x 106

308.2

123.8 203.1 16.9 141.8 301.2 27.6 177.5 375.3 45.8 224.8 561.2 80.1 244.3 587.1 91.6 328.2 122.7 17.6 28.2 156.9 135.7 109.8 176.2 331.4 171.6 214.9 645.3 348.8 226.6 738.2 368.4 244.1 859.2 431.6 333.2 159.7 103.2 78.8 174.4 201.9 137.5 209.3 346.3 312.0 226.3 796.7 372.5 244.0 949.5 452.4 1: Solubility of each component was measured from the mixture. Source: Kosal, E.; Lee, C. H.; Holder, G. D. J. Supercrit. Fluids (1992), 5(3), 169-179.

1000

750 y x 106

T (K)

500

Prog 308.2 K Prog 328.2 K Prog 333.2 K Chol 308.2 K Chol 328.2 K Chol 333.2 K

250

0 100

150

200 P (bar)

[P-114]

Progesterone (1) + Testosterone (2) Mixture1) 900

600

Prog 308.2 K Prog 328.2 K Test 308.2 K Test 328.2 K

y x 106

6 y2 x 106 T (K) P (bar) y1 x 10 308.2 121.8 188.7 17.8 141.2 258.1 30.2 157.2 328.3 40.5 175.0 382.6 48.0 193.9 468.8 56.1 209.9 585.5 70.1 229.0 591.1 76.2 243.6 661.2 88.1 328.2 121.3 38.6 4.8 139.4 73.4 9.0 156.5 199.3 24.4 174.5 312.9 39.4 193.0 496.0 55.5 211.0 582.3 78.2 226.8 709.6 96.5 243.8 785.3 109.3 1: Solubility of each component was measured from the mixture. Source: Kosal, E.; Lee, C. H.; Holder, G. D. J. Supercrit. Fluids (1992), 5(3), 169-179.

250

300

0 100

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150

200 P (bar)

250

Solubility Data P

667

[P-115]

Prometone (C10H19N5O; MW=225.29) T (K) P1) (bar) S1,2) (g/L)

y3) x 106

7000 80 0.07 48 85 0.30 158 90 1.05 413 95 2.63 875 3500 100 4.28 1320 110 6.41 1820 120 8.70 2350 150 15.20 3770 0 180 20.50 4860 50 6230 210 27.30 1: Obtained by digitizing the graph in the original article. 2: The data may have a large reading error as the source graph is small. 3: Calculated from S. Synonym: 2-Methoxy-4,6-bis(isopropylamino)-1,3,5triazine Source: Rodrigues, S. V.; Nepomuceno, D.; Martins, L. V.; Baumann, W. Fresenius' J. Anal. Chem. (1998), 360(1), 58-61. y x 106

313.15

150

250

P (bar)

[P-116]

Prometryne (C10H19N5S; MW=241.36) y1) x 106

1200 313.15 K 333.15 K 353.15 K

800 yx

147 279 308 360 331 331 312 334 363 363 500 559 540 522 525 40 99 114 161 312 422 492 577 654 669

106

T (K) P (bar) 313.15 84.7 92.7 101.8 115.0 139.5 154.3 162.3 176.5 194.2 205.7 225.7 237.6 242.2 272.5 292.3 333.15 82.5 98.4 108.1 113.9 134.9 169.8 188.0 207.9 215.8 231.9

400

0 0

CAT4240—CHAPTER 16—1/11/2006—16:31—SRIDHAR—XML MODEL C – pp. 587–693

100

200 P (bar)

300

668

Solubility in Supercritical Carbon Dioxide

244.5 661 272.9 665 307.2 610 353.15 80.8 29 92.2 47 105.3 118 119.0 191 129.2 210 151.5 363 173.1 724 177.7 739 213.6 1007 234.2 1018 262.2 753 270.1 676 282.6 569 303.8 467 1: Obtained by digitizing the graph in the original article. Synonym: 2,4-Bis(isopropylamino)-6-methylthio-1,3,5-triazine Source: Knez, Z.; Rizner-Hras, A.; Kokot, K.; Bauman, D. Fluid Phase Equil. (1998), 152(1), 95-108.

Prometryne (C10H19N5S; MW=241.36) P1)

S1,2)

y3)

[P-117]

106

(bar) (g/L) x 1400 80 0.03 20 85 0.09 46 90 0.31 112 95 0.84 262 700 100 1.25 359 110 1.81 480 120 2.26 571 150 3.67 854 0 180 4.78 1060 1280 210 5.99 50 1: Obtained by digitizing the graph in the original article. 2: The data may have a large reading error as the source graph is small. 3: Calculated from S. Synonym: 2,4-Bis(isopropylamino)-6-methylthio-1,3,5triazine Source: Rodrigues, S. V.; Nepomuceno, D.; Martins, L. V.; Baumann, W. Fresenius' J. Anal. Chem. (1998), 360(1), 58-61.

y x 106

T (K) 313.15

100

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150 P (bar)

200

250

Solubility Data P

669

1,2-Propanediol (C3H8O2; MW=76.09)

[P-118]

311 K 318 K 328 K

y x 106

y x 106 T (K) P (bar) 51 311 36.6 50 46.1 77 58.0 400 117 66.0 119 66.0 192 73.6 300 78.1 300 370 80.4 92 318 13.2 72 25.6 200 85 45.6 115 58.2 152 66.4 194 72.4 100 262 78.1 303 80.8 360 83.6 0 158 328 14.7 131 26.6 0 129 36.6 147 48.8 185 60.7 239 70.5 286 76.2 80.1 341 Synonym: Propylene glycol Source: Chylinski, K. ; Gregorowicz, J. Fluid Phase Equil. (1998), 143(1-2), 163-172.

1-Propanol (C3H8O ; MW=60.10) T (K) P (bar) 311 10.2 16.3 29.6 37.9 46.4 54.4 61.2 66.1 71.2 71.2 73.3 75.4 76.9

y x 106 6810 4920 3780 3810 4050 4510 5010 6040 7240 7050 8280 9320 10570

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50

100

P (bar)

[P-119]

670

Solubility in Supercritical Carbon Dioxide

10630 9.6 20000 6950 16.9 5500 26.0 5190 35.4 5200 45.0 15000 5510 53.3 6260 62.6 7310 69.6 10000 7290 69.8 7290 69.8 8780 74.9 10550 78.7 5000 12610 81.7 13770 323 10.4 8890 19.0 7230 28.1 0 6710 36.1 0 6610 48.0 7040 57.2 7860 66.0 9350 74.2 10350 78.2 12510 83.0 86.4 14830 Source: Chylinski, K. ; Gregorowicz, J. Fluid Phase Equil. (1998), 143(1-2), 163-172. 318

y x 106

311 K 318 K 323 K

50

100

P (bar)

2-Propanol (C3H8O ; MW=60.1) yx

5400 3400 3300 3300 3500 8900 7300 6400 8400 9600 11900 25000 21500 19700 18700 19100 18800 24500

30000

293.2 K 313.2 K 333.1 K

20000 y x 106

T (K) P (bar) 293.2 11 21 31 41 51 313.2 21 31 41 51 61 71 333.1 21 31 41 51 61 71 81

[P-120]

106

10000

0 0

Source: Bamberger, A.; Maurer, G. J. Chem. Thermodyn. (2000), 32(5), 685-700.

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30

60 P (bar)

90

Solubility Data P

671

Propazine (C9H16ClN5; MW=229.71) T (K) 313.15

P1)

(bar)

S1,2)

(g/L)

y3)

x

[P-121]

106

80

y x 106

80 0.005 3.3 85 0.013 6.9 90 0.036 13.9 95 0.059 19.1 40 100 0.075 22.6 120 0.129 34.3 150 0.181 44.3 0 180 0.229 53.5 66.0 210 0.293 50 1: Obtained by digitizing the graph in the original article. 2: The data may have a large reading error as the source graph is small. 3: Calculated from S. Synonym: 2-Chloro-4,6-bis(isopropylamino)-1,3,5-triazine Source: Rodrigues, S. V.; Nepomuceno, D.; Martins, L. V.; Baumann, W. Fresenius' J. Anal. Chem. (1998), 360(1), 58-61.

100

150

200

P (bar)

Propranolol (C16H21NO2; MW=259.35) yx

[P-122]

106 36.7 61.0 75.2 85.3 93.4 110.2 130.8 151.6 150.2 58.4 87.2 105.7 120.4 143.6 175.1 218.4 278.9 304.2 42.7 82.1 123.2 179.9 235.3 303.6 400.0 473.9 663.9

2000

308 K 318 K 328 K 338 K 348 K

y x 106

T (K) P (bar) 308 122 152 182 213 243 273 304 334 355 318 122 152 182 213 243 273 304 334 355 328 122 152 182 213 243 273 304 334 355

250

1000

0 100

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200

300 P (bar)

400

672

Solubility in Supercritical Carbon Dioxide

338

348

122 152 182 213 243 273 304 334 355 122 152 182 213 243 273 304 334 355

35.8 85.6 149.7 225.6 319.0 500.2 702.2 900.7 1162.3 41.4 113.0 171.3 302.7 463.4 708.0 958.0 1694.5 2396.1

Synonym: 1-(Isopropylamino)-3-(1-naphthyloxy)-2propanol Source: Yamini, Y.; Arab, J.; Asghari-Khiavi, M. Pharm. Biomed. Anal. (2003), 32(1), 181-187.

Propyl 2,5-dichlorobenzoate (C10H10Cl2O2; MW=233.09) T (K)

P(bar)

yx

[P-123]

106 y=0.0039 y=0.0279 y=0.0352 y=0.0528

P (bar)

313.15 91.9 3900 300 320.95 105.2 3900 332.95 127.5 3900 354.75 158.3 3900 373.95 172.1 3900 200 296.45 71.7 27900 314.15 132.7 27900 346.15 214.3 27900 363.65 249.2 27900 100 294.65 70.0 35200 309.35 117.6 35200 339.55 201.2 35200 362.05 251.5 35200 298.55 90.2 52800 0 314.95 140.2 52800 250 332.45 187.8 52800 349.25 227.0 52800 365.25 257.4 52800 Synonym: 2,5-Dichlorobenzoic acid n-propyl ester Source: Shen, Z.; McHugh, M. A.; Lott, K. M.; Wright, M. E. Fluid Phase Equil. (2004), 216(1), 1-12.

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300

350 T (K)

400

Solubility Data P

673

[P-124]

Propyl gallate (C10H12O5; MW=212.20) y x 106 T (K) P (bar) 313.1 150 5.02 175 6.22 200 7.39 250 9.45 333.1 150 6.94 175 10.3 200 13.1 250 18.7 Synonyms: Gallic acid propyl ester; 3,4,5Trihydroxybenzoic acid propyl ester Source: Cortesi, A.; Kikic, I.; Alessi, P.; Turtoi, G.; Garnier, S. J. Supercrit. Fluids (1999), 14(2), 139-144.

20

y x 106

313.1 K 333.1 K

10

0 100

200

300

P (bar)

Propyl 4-hydroxybenzoate (C10H12O3; MW=180.20)

y x 106

y × 106 T (K) P (bar) 308.15 94.1 44 109.2 74 130.6 122 152.0 164 173.3 203 193.7 248 220.9 298 318.15 96.8 19 108.5 43 132.0 111 152.7 180 171.3 244 192.6 311 214.7 400 328.15 105.1 27 114.8 50 131.3 92 153.4 175 172.0 272 197.5 409 220.2 612 Synonym: 4-Hydroxybenzoic acid propyl ester; Source: Cheng, K.-W.; Tang, M.; Chen, Y.-P. Fluid Phase Equil. (2002), 201(1), 79-96.

[P-125]

308.15 K 318.15 K 328.15 K

600

400

200

0 50

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150 P (bar)

250

674

Solubility in Supercritical Carbon Dioxide

[P-126]

Protocatechualdehyde (C7H6O3; MW=138.12) yx

0.43 2.83 3.91 5.71 7.45 9.40 10.10 10.58 0.29 3.10 6.06 8.22 9.82 12.46 15.32 18.52 0.13 4.24 8.33 16.57 20.65 30.97 36.78 45.79

313 K 323 K 333 K

45

y x 106

T (K) P (bar) 313 100 150 200 300 350 400 450 500 323 100 150 200 300 350 400 450 500 333 100 150 200 300 350 400 450 500

106

30

15

0 0

200

400

600

P (bar)

Synonyms: Catechaldehyde; 3,4-Dihydroxybenzaldehyde Source: Murga, R.; Sanz, M. T.; Beltran, S.; Cabezas, J. L. J. Supercrit. Fluids (2002), 23(2), 113-121.

Protocatechuic acid (C7H6O4; MW=154.12) T (K) P (bar) 313 100 150 200 300 350 400 450 500

y x 106 0.044 0.106 0.208 0.348 0.416 0.474 0.514 0.532

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[P-127]

Solubility Data P

675

3

100 0.025 150 0.121 200 0.304 300 0.717 350 0.975 2 400 1.113 450 1.199 500 1.291 333 100 0.002 1 150 0.095 200 0.525 300 1.021 350 1.547 400 1.814 0 450 2.227 0 500 2.595 Synonym: 3,4-Dihydroxybenzoic acid Source: Murga, R.; Sanz, M. T.; Beltran, S.; Cabezas, J. L. J. Supercrit. Fluids (2002), 23(2), 113-121.

313 K 323 K 333 K

y x 106

323

200

400

600

P (bar)

Pyrazine-2-carboxylic acid (C5H4N2O2; MW=124.10)

[P-128]

106

y x 106

yx T (K) P (bar) 12 308.15 91.8 3.96 109.4 5.08 135.3 6.19 6 153.8 8.59 160.3 8.60 170.4 9.18 0 195.3 9.45 50 Synonyms: 2-Pyrazinoic acid; 2-Carboxypyrazine Source: Nakatani, T.; Tohdo, T.; Ohgaki, K.; Katayama, T. J. Chem. Eng. Data (1991), 36(3), 314-316.

Pyrene (C16H10; MW=202.25) T (K) 313

P (bar) 107.0 111.5 117.2 124.0 131.0 136.7 144.5 150.3 152.1 160.4

yx

106 56 65 80 100 108 123 138 145 153 165

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150

250

P (bar)

[P-129]

676

Solubility in Supercritical Carbon Dioxide

323

178 192 204 218 228 236 244 255 260 270 278 286 298 308 315 320 326 333 339 347 353 360 45 58 72 86 105 120 140 157 175 193 216 233 249 261 277 293 305 318 325 333 342 352 361 372 384 397

600 313 K 323 K 333 K

400 y x 106

169.9 181.0 191.0 200.0 210.3 216.9 224.4 234.4 241.2 249.8 258.4 265.7 276.2 285.9 293.6 300.1 308.0 315.2 321.1 329.3 337.0 347.2 117.8 121.2 125.0 129.6 135.0 141.6 149.1 157.2 165.0 172.9 183.4 192.2 200.2 208.4 218.3 226.2 233.7 241.0 247.4 254.9 262.1 269.1 275.6 283.3 291.1 300.1

200

0 0

100

CAT4240—CHAPTER 16—1/11/2006—16:31—SRIDHAR—XML MODEL C – pp. 587–693

200 P (bar)

300

400

Solubility Data P

333

306.9 313.5 323.1 333.2 343.1 350.0 114.0 119.5 125.1 131.3 138.8 147.9 158.6 165.7 179.4 193.8 200.3 207.3 215.7 227.8 235.9 236.9 243.6 244.0 252.5 254.6 260.9 275.7 283.5 293.8 300.9 307.5 314.0 321.6 331.3 338.3 345.1

677

405 410 423 433 444 450 22 31 42 52 71 100 138 155 204 250 262 284 303 334 356 358 373 374 395 400 412 440 453 470 483 495 506 520 531 541 550

Synonym: Benzo[def]phenanthrene Source: Anitescu, G.; Tavlarides, L. L. J. Supercrit. Fluids (1997), 10(3), 175-189.

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678

Solubility in Supercritical Carbon Dioxide

Pyrene (C16H10; MW = 202.25) T (K) 308.2

P (bar) 80.4 80.9 82.2 82.5 83.4 84.4 85.1 85.6 86.0 89.0 89.3 91.8 95.1 96.6 97.4 99.1 100.0 100.3 109.2 109.5 110.0 111.2 116.5 119.5 120.7 121.0 121.9 130.0 130.5 131.2 140.4 141.4 142.0 150.5 151.7 160.5 163.0 170.4 171.7 180.5 181.0 182.6

y x 106 25 23 35 32 36 44 34 33 35 55 53 58 62 74 68 78 77 76 95 95 87 89 106 110 109 106 111 124 121 124 135 136 137 146 145 158 159 168 169 173 178 180

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[P-130]

Solubility Data P

323.2

185 197 196 15 29 45 62 77 86 100 106 121 141 160 172 196 218 235 245 254 264 276 287 12 14 23 26 26 31 30 38 48 64 64 84 98 100 108 117 127 130 138 152 160 166 169 184 184 185 203

308.2 K 318.2 K 323.2 K 328.2 K

300

y x 106

318.2

191.2 201.6 203.5 95.0 100.0 105.0 110.0 115.0 120.0 124.6 130.0 134.0 145.0 156.0 169.5 184.5 198.0 208.0 216.0 224.5 232.5 244.2 254.0 100.1 102.0 105.2 105.9 106.7 108.1 108.8 110.2 114.5 118.5 121.0 125.7 129.4 130.3 135.6 137.0 140.7 145.0 146.2 151.0 156.0 156.5 160.5 166.0 167.0 168.2 174.6

679

200

100

0 50

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150 P (bar)

250

680

Solubility in Supercritical Carbon Dioxide

328.2

181.0 181.4 193.0 195.6 202.0 212.2 219.5 228.5 105.0 110.0 115.0 120.0 125.0 130.0 134.2 137.2 145.5 157.0 166.1 174.8 186.1 194.2 205.5 209.8 214.7 225.2 237.0 245.0

203 210 227 229 241 262 273 284 13 22 33 50 67 82 94 97 123 154 176 195 219 231 255 269 282 297 317 329

Synonym: Benzo[def]phenanthrene Source: Bartle, K. D.; Clifford, A. A.; Jafar, S. A. J. Chem. Eng. Data (1990), 35(3), 355-360.

Pyrene (C16H10; MW=202.25) T (K) P (bar) 308.15 83.6 104.3 125.0 138.8 207.7 345.6 483.4

yx

106 30.3 79.6 119.0 134.0 210.0 256.0 347.0

CAT4240—CHAPTER 16—1/11/2006—16:31—SRIDHAR—XML MODEL C – pp. 587–693

[P-131]

Solubility Data P

681

1000 104.3 15.3 66.6 125.0 123.0 138.8 279.0 207.7 375.0 276.7 448.0 345.6 540.0 483.4 2.7 343.15 104.3 500 32.0 125.0 56.2 138.8 189.0 173.3 315.0 207.7 554.0 276.7 862.0 414.5 938.0 483.4 0 Synonym: Benzo[def]phenanthrene 0 Source: Johnston, K. P.; Ziger, D. H.; Eckert, C. A. Ind. Eng. Chem. Fund. (1982), 21(3), 191-197. 323.15

y x 106

308.15 K 323.15 K 343.15 K

200

400 P (bar)

[P-132]

Pyrene (C16H10; MW=202.25) 313

373

423

P (bar) 100 150 200 250 300 350 400 450 100 150 200 250 300 350 400 450 100 150 200 250 300 350 400 450

yx

6 46 99 142 180 230 270 300 16 22 130 380 680 1010 1230 1560 59 97 270 630 1350 2380 3320 4240

313 K 373 K 423 K 473 K

4000 y x 106

T (K)

106

2000

0 0

CAT4240—CHAPTER 16—1/11/2006—16:31—SRIDHAR—XML MODEL C – pp. 587–693

200

400 P (bar)

600

682

Solubility in Supercritical Carbon Dioxide

473

150 220 200 490 250 1010 300 1850 350 2780 400 3940 450 4790 Synonym: Benzo[def]phenanthrene Source: Miller, D. J.; Hawthorne, S. B.; Clifford, A. A.; Zhu, S. J. Chem. Eng. Data (1996), 41(4), 779-786.

[P-133]

Pyrene (C16H10; MW=202.25) 106

yx T (K) P (bar) 323.1 129.4 114 167.9 188 197.7 268 244.5 339 299.8 416 325.8 423 439.0 546 482.5 582 Synonym: Benzo[def]phenanthrene Source: Yu, E.; Richter, M.; Chen, P.; Wang, X.; Tavlarides, L. L. Ind. Eng. Chem. Res. (1995), 34(1), 340-346.

y x 106

800

400

0 100

200

T (K) 313

P (bar) 100 103 110 117 124 131 138 145 152 159 165 176 176 186 193

5 5 5 5 5 5 5 5 5 5 5 5 5 5 5

500

[P-134] y x 106

(mol%)

400

P (bar)

Pyrene (C16H10; MW=202.25) Butane1)

300

70 81 100 115 133 148 167 177 190 205 216 242 228 254 268

CAT4240—CHAPTER 16—1/11/2006—16:31—SRIDHAR—XML MODEL C – pp. 587–693

Solubility Data P

333

5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 5 5 5 5 5 5 5

278 289 302 312 325 337 346 360 375 390 400 411 420 432 449 147 164 180 202 222 242 260 276 293 310 330 349 363 380 395 417 440 456 470 482 495 507 520 533 544 557 564 585 601 617 100 115 127 140 164 186 209

900

313 K, 5% C4H10 313 K, 10% C4H10 333 K, 5% C4H10 333 K, 10% C4H10

600 y x 106

313

200 207 214 221 228 235 241 249 258 268 275 283 290 297 308 108 115 121 128 136 143 149 156 163 170 177 184 190 196 204 215 227 234 241 248 255 262 269 276 283 290 296 305 314 322 119 123 128 133 138 145 152

683

300

0 0

100

CAT4240—CHAPTER 16—1/11/2006—16:32—SRIDHAR—XML MODEL C – pp. 587–693

200 P (bar)

300

400

684

333

Solubility in Supercritical Carbon Dioxide

159 166 173 179 186 193 200 207 213 220 227 234 242 248 255 262 269 276 283 290 297 303 311 106 111 116 120 125 131 139 145 155 162 169 176 183 191 200 207 214 221 228 236 245 252

5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10

236 257 287 301 323 350 373 390 420 438 460 474 500 519 537 554 575 590 613 627 648 664 680 110 126 149 163 181 200 237 255 300 325 361 388 454 455 488 514 539 570 585 614 645 663

CAT4240—CHAPTER 16—1/11/2006—16:32—SRIDHAR—XML MODEL C – pp. 587–693

Solubility Data P

685

259 267 283 291 300 307 312 319

10 10 10 10 10 10 10 10

690 714 763 787 815 831 846 865

1: Cosolvent in CO2. Synonym: Benzo[def]phenanthrene Source: Anitescu, G.; Tavlarides, L. L. J. Supercrit. Fluids (1997),11(1,2), 37-51.

Pyrene (C16H10; MW=202.25)

313

P (bar) 111 117 124 131 139 144 151 160 165 175 180 185 191 199 206 215 220 226 233 240 249 254 261 269 275 285 289 301 325 344

(mol%) 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5

[P-135] y x 106 74 90 107 121 140 149 161 178 187 202 210 217 225 238 249 260 268 276 286 294 307 314 322 333 341 352 359 372 401 420

313 K, 5% C2H6 313 K, 10% C2H6 333 K, 5% C2H6 333 K, 10% C2H6

600

y x 106

T (K)

Ethane1)

400

200

0 0

100

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200 P (bar)

300

400

686

Solubility in Supercritical Carbon Dioxide

313

333

110 117 125 132 139 145 152 159 165 174 179 186 193 200 207 214 221 227 234 241 248 255 262 268 276 283 290 300 322 345 110 116 121 130 136 141 151 159 164 171 180 185 192 199 206 213 220 230 235 240 251

10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5

91 110 129 141 157 168 180 198 207 223 233 245 257 269 279 281 302 311 322 333 345 354 364 375 385 396 404 418 448 476 24 32 49 71 90 103 137 164 181 204 232 249 265 290 310 331 350 375 388 400 426

CAT4240—CHAPTER 16—1/11/2006—16:32—SRIDHAR—XML MODEL C – pp. 587–693

Solubility Data P

333

261 270 280 292 300 307 314 321 340 111 117 122 129 136 140 150 159 165 172 179 186 193 200 207 214 221 229 236 241 252 262 269 276 284 292 299 307 315 331

687

5 5 5 5 5 5 5 5 5 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10

450 471 493 514 532 547 559 575 600 39 50 64 90 113 125 161 192 212 230 257 280 302 324 343 367 388 410 426 440 469 485 513 530 546 563 577 584 612 641

1: Cosolvent in CO2. Synonym: Benzo[def]phenanthrene Source: Anitescu, G.; Tavlarides, L. L. J. Supercrit. Fluids (1997), 11(1,2), 37-51.

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688

Solubility in Supercritical Carbon Dioxide

Pyrene (C16H10; MW=202.25)

313

333

333

P (bar) 110 119 131 132 141 152 165 179 193 209 221 244 259 274 290 311 117 131 145 159 176 186 198 211 226 249 262 276 289 299 307 318 119 131 146 160 175 185 199 210 226 250 261 275

(mol%) 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 10 10 10 10 10 10 10 10 10 10 10 10

[P-136]

y1) x 106 122 155 188 190 215 241 274 305 335 362 380 413 442 472 509 544 39 78 128 196 268 313 364 413 462 541 579 616 647 672 693 714 84 131 210 287 362 410 479 520 587 663 719 770

313 K, 5% MeOH 333 K, 5% MeOH 333 K, 10% MeOH

900

y x 106

T (K)

Methanol1)

600

300

0 0

100

CAT4240—CHAPTER 16—1/11/2006—16:32—SRIDHAR—XML MODEL C – pp. 587–693

200 P (bar)

300

400

Solubility Data P

689

290 300 311 320

10 10 10 10

826 860 890 929

1: Cosolvent in CO2. Synonym: Benzo[def]phenanthrene Source: Anitescu, G.; Tavlarides, L. L. J. Supercrit. Fluids (1997),11(1,2), 37-51.

[P-137]

Pyrene (C16H10; MW=202.25) T (K) 313

P (bar) 108 114 121 128 135 141 148 155 162 169 176 183 190 197 204 210 217 224 231 238 245 251 258 265 270 279 286 293

n -Propane1) (mol%) 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5

y x 106 81 96 111 127 142 155 168 180 191 205 218 230 241 252 264 273 285 296 308 320 330 339 350 360 367 379 387 395

CAT4240—CHAPTER 16—1/11/2006—16:32—SRIDHAR—XML MODEL C – pp. 587–693

690

Solubility in Supercritical Carbon Dioxide

333

5 5 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10

403 416 110 123 146 160 173 191 205 222 240 253 270 284 313 327 344 359 377 391 401 418 429 441 455 463 478 489 502 515 527

110 116 122 128 136 146 152 159 165 174 182 190 196 203 211 217 224 231 238 245

5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5

50 63 79 102 130 161 180 207 225 256 281 308 325 350 375 390 412 427 450 469

800 313 K, 5% C3H8 313 K, 10% C3H8 333 K, 5% C3H8 333 K, 10% C3H8

600

y x 106

313

300 311 107 111 118 124 131 138 144 152 159 165 172 179 193 200 208 216 226 234 240 248 254 262 269 275 283 291 299 308 317

400

200

0 0

100

CAT4240—CHAPTER 16—1/11/2006—16:32—SRIDHAR—XML MODEL C – pp. 587–693

200 P (bar)

300

400

Solubility Data P

691

251 258 265 272 279 286

333

5 5 5 5 5 5

481 502 520 534 555 570

292

5

582

300 307

5 5

600 615

313

5

625

102

10

66

107

10

80

111

10

94

115

10

110

120

10

126

122

10

135

125

10

150

128

10

161

132

10

169

135

10

182

139

10

198

145

10

219

151

10

236

158

10

265

165

10

287

173

10

313

184

10

354

193

10

385

203

10

425

214

10

463

224

10

492

235

10

527

245

10

561

256

10

590

266

10

620

276

10

649

287

10

675

300

10

711

308

10

726

315 10 733 1: Cosolvent in CO2. Synonym: Benzo[def]phenanthrene Source: Anitescu, G.; Tavlarides, L. L. J. Supercrit. Fluids (1997),11(1,2), 37-51.

CAT4240—CHAPTER 16—1/11/2006—16:32—SRIDHAR—XML MODEL C – pp. 587–693

692

Solubility in Supercritical Carbon Dioxide

Pyrocatechol (C6H6O2; MW=110.11)

[P-138]

106

333.15 K 348.15 K 363.15 K

y x 106

yx T (K) P (bar) 100 333.15 122 125 335 150 1078 175 1625 200 1990 225 2273 250 2608 275 2738 5000 300 2957 325 2998 350 3054 4000 348.15 100 148 125 345 150 569 3000 175 1031 200 1524 225 1917 2000 250 2358 275 2708 300 3096 1000 325 3494 350 3847 363.15 100 210 125 283 0 0 150 453 175 906 200 1463 225 1963 250 2400 275 2900 300 3656 325 4065 350 4583 Synonyms: 1,2-Benzenediol; Catechol Source: Julian, G.-G.; Molina, M. J.; Rodriguez, F.; Mirada, F. J. Chem. Eng. Data (2001), 46(4), 918-921.

100

CAT4240—CHAPTER 16—1/11/2006—16:32—SRIDHAR—XML MODEL C – pp. 587–693

200 P (bar)

300

400

Solubility Data P

693

Pyrocatechol (C6H6O2 ; MW=110.11)

318

328

338

P (bar) 122 162 203 243 284 324 365 405 122 162 203 243 284 324 365 405 122 162 203 243 284 324 365 405 122 162 203 243 284 324 365 405

S (g/L) 1.33 2.02 2.20 2.47 2.65 2.87 3.14 3.27 1.33 2.02 2.57 3.13 3.45 3.85 4.18 4.54 0.98 2.19 3.12 3.78 4.63 5.18 5.53 5.82 0.67 2.34 3.79 4.86 5.95 6.77 7.71 8.63

yx

690 970 1010 1100 1150 1220 1310 1340 800 1060 1260 1470 1570 1700 1810 1920 750 1280 1630 1880 2210 2390 2490 2560 660 1560 2180 2580 2990 3270 3610 3940

4000

3000 y x 106

T (K) 308

[P-139]

106

308 K 318 K 328 K 338 K

2000

1000

0 100

Synonyms: 1,2-Benzenediol; Catechol Source: Yamini, Y.; Fathi, M. R.; Alizadeh, N .; Shamsipur, M. Fluid Phase Equil. (1998), 152(2), 299-305.

CAT4240—CHAPTER 16—1/11/2006—16:32—SRIDHAR—XML MODEL C – pp. 587–693

200

300 P (bar)

400

17

Solubility Data Q

Quercetin (C15H10O7; MW=302.24)

[Q-1]

Ethanol1) y x 106 8000 (mol%) 313.15 80 5 220 10 710 15 1350 6000 20 1980 25 3170 30 5150 90 5 320 4000 10 880 15 1680 20 2770 25 6370 2000 100 5 520 10 1220 15 2640 0 20 5480 110 5 1000 0 10 2040 15 4270 120 5 1600 1: Cosolvent in CO2. Synonym: 3,3',4',5,7-Pentahydroxyflavone Source: Chafer, A.; Fornari, T.; Berna, A.; Stateva, R. P. J. Supercrit. Fluids (2004), 32(1-3), 89-96. P (bar)

80 bar 90 bar 100 bar 110 bar 120 bar

y x 106

T (K)

10

20

30

Ethanol (mol%)

695

CAT4240—CHAPTER 17—1/11/2006—18:40—SRIDHAR—XML MODEL C – pp. 695–697

696

Solubility in Supercritical Carbon Dioxide

p -Quinone (C6H4O2; MW=108.09)

[Q-2]

106

308.15 K 318.15 K

y x 106

yx T (K) P (bar) 308.15 86.7 2950 36000 95.1 6820 109.5 9280 121.8 11300 141.2 14400 24000 173.6 19600 216.4 22300 259.3 23300 290.7 24800 318.15 86.1 1060 12000 97.4 5190 114.6 12200 126.4 15500 159.3 19500 0 186.6 23500 50 227.1 28600 264.4 30500 292.1 31400 Synonyms: 1,4-Benzoquinone; p-Benzoquinone; Quinone Source: Coutsikos, P.; Magoulas, K.; Tassios, D. J. Chem. Eng. Data (1997), 42(3), 463-466.

150

250

p -Quinone (C6H4O2; MW=108.09) yx

[Q-3]

106 1300 4600 10390 16030 17070 19850 20520 23740 26630 29700 31670 1500 3460 6100 9890 15900 24250 26490 28130 31970 32600 32650

40000 333 K 348 K 363 K

30000 y x 106

T (K) P (bar) 333 100 125 150 175 200 225 250 275 300 325 350 348 100 125 150 175 200 225 250 275 300 325 350

350

P (bar)

20000

10000

0 50

CAT4240—CHAPTER 17—1/11/2006—18:40—SRIDHAR—XML MODEL C – pp. 695–697

150

250 P (bar)

350

Solubility Data Q

363

100 2500 125 3290 150 7110 175 9400 200 13330 225 17510 250 29020 275 30740 300 34940 325 34880 350 35540 Synonyms: 1,4-Benzoquinone; p-Benzoquinone; Quinone Source: Garcia-Gonzalez, J.; Molina, M. J.; Rodriguez, F.; Mirada, F. Fluid Phase Equil. (2002), 200(1), 31-39.

CAT4240—CHAPTER 17—1/11/2006—18:40—SRIDHAR—XML MODEL C – pp. 695–697

697

18

Solubility Data R

Rape seed oil1) 244 560 2510 4810 6700 9320 12700 13900 18800 20900 20500 21100 21600 20600 21600 22000 22600 540 492 230 1700 3680 6040 8530 13000 14500 16000 17900 21200 25200 32300 30900 39000 38700 39800 43400

200000 313.15 K 333.15 K 353.15 K 373.15 K

150000

6

w × 10

y × 10

P (bar) T (K) 313.15 101.1 142.2 185.6 235.8 291.4 335.7 427.4 434.5 584.1 622.1 675.4 693.2 708.2 714.1 768.8 785.1 803.4 333.15 107.0 144.8 155.2 182.7 231.1 279.3 321.6 358.0 384.3 405.9 437.6 454.8 499.0 581.1 589.9 662.1 670.2 692.8 729.3

[R-1] 6

100000

50000

0

0

300

600 P (bar)

900

699

CAT4240—CHAPTER 18—1/11/2006—18:46—SRIDHAR—XML MODEL C – pp. 699–705

700

Solubility in Supercritical Carbon Dioxide

732.0 45100 732.7 42300 791.0 48900 801.1 47000 353.15 99.0 693 146.2 629 191.9 594 232.9 1160 282.6 3550 321.8 5920 368.6 9080 417.7 14400 470.3 17600 491.9 22200 545.0 29400 619.9 44800 635.4 53000 721.7 75600 737.1 78400 764.6 87900 777.7 89800 816.5 105200 373.15 99.1 635 152.8 545 197.1 522 242.4 788 285.4 2520 329.1 4870 398.6 12500 443.9 21100 489.7 30900 540.2 40900 581.6 55200 637.7 75600 642.2 77500 685.9 105000 702.7 121500 741.0 138700 743.3 146200 770.3 178900 1: Refined rapeseed oil with a low content of erucic acid. Source: Klein, T.; Schulz, S. Ind. Eng. Chem. Res. (1989), 28(7), 1073-1081.

CAT4240—CHAPTER 18—1/11/2006—18:46—SRIDHAR—XML MODEL C – pp. 699–705

Solubility Data R

701

Reserpine (C33H40N2O9; MW=608.68)

[R-2]

106

3 313 K 333 K 353 K 373 K

2

y × 106

y× P (bar) 50.0 0.132 73.0 0.323 81.9 0.686 88.0 1.653 333 55.0 0.241 82.5 0.467 108.8 0.896 134.2 1.972 353 60.3 0.362 101.0 0.603 130.0 1.122 146.9 2.276 373 66.1 0.611 111.0 0.861 148.1 1.368 185.0 2.631 Synonym: 18b-Hydroxy-11, 17a-dimethoxy3b, 20a-yohimban-16b-carboxylic acid methyl ester 3,4,5-trimethoxybenzoate Source: Tzvetkova, E., Doctoral Thesis, Siegen University, Siegen, Germany, 2001. T (K) 313

1

0

0

50

100

Resorcinol (C6H6O2 ; MW=110.11)

318

328

P (bar) 122 162 203 243 284 324 365 405 122 162 203 243 284 324 365 405 122 162 203 243 284 324 365 405

S (g/L) 0.21 0.33 0.40 0.48 0.53 0.59 0.68 0.73 0.24 0.40 0.51 0.65 0.77 0.86 0.96 1.06 0.26 0.47 0.65 0.84 1.04 1.22 1.38 1.49

y×

200

[R-3]

106 110 159 184 216 232 250 282 298 147 210 251 304 350 379 418 449 197 275 346 420 499 561 619 655

1200

y × 106

T (K) 308

150

P (bar)

308 K 318 K 328 K 338 K

800

400

0

0

CAT4240—CHAPTER 18—1/11/2006—18:46—SRIDHAR—XML MODEL C – pp. 699–705

200 P (bar)

400

702

Solubility in Supercritical Carbon Dioxide

338

122 162 203 243 284 324 365 405

0.24 0.45 0.79 1.10 1.39 1.62 1.92 2.13

244 300 455 585 699 781 898 973

Synonyms: 1,3-Benzenediol; 1,3-Dihydroxybenzene Source: Yamini, Y.; Fat'hi, M. R.; Alizadeh, N.; Shamsipur, M. Fluid Phase Equil. (1998), 152(2), 299-305.

Resveratrol (C14H12O3; MW=228.24) T (K)

P (bar)

Ethanol1) (mol %)

[R-4]

y × 106

313

5.0 mol% 7.5 mol% 10.0 mol% 12.5 mol% 15.0 mol%

y × 106

80 5.0 46.4 90 5.0 54.1 100 5.0 63.3 110 5.0 73.5 300 120 5.0 84.7 130 5.0 98.1 140 5.0 112.4 80 7.5 111.3 90 7.5 151.9 200 100 7.5 186.3 110 7.5 232.7 80 10.0 93.1 90 10.0 121.4 100 100 10.0 150.8 110 10.0 197.2 120 10.0 270.1 80 12.5 56.9 90 12.5 69.5 0 100 12.5 102.0 50 110 12.5 132.4 120 12.5 190.7 80 15.0 41.4 90 15.0 51.0 100 15.0 59.4 110 15.0 75.9 120 15.0 105.1 130 15.0 136.6 140 15.0 175.4 1 : Cosolvent in CO2. Synonyms: (E)-Resveratrol; 3,4',5-Stilbenetriol; 3,4',5-Trihydroxy-trans-stilbene Source: Berna, A.; Chafer, A.; Monton, J. B.; Subirats, S. J. Supercrit. Fluids (2001), 20(2), 157-162.

CAT4240—CHAPTER 18—1/11/2006—18:46—SRIDHAR—XML MODEL C – pp. 699–705

100 P (bar)

150

Solubility Data R

703

Retinol (C20H30O; MW=286.45)

333

353

P (bar) W (g/kg) 200 10.3 220 12.5 240 15.1 260 18.5 280 19.8 300 21.8 320 22.4 350 23.8 200 10.0 220 11.7 240 16.0 260 19.0 200 9.2 220 9.4 240 11.0 260 13.9 280 18.0 300 22.3 320 25.2 350 27.6

y×

1600 1950 2350 2880 3100 3420 3500 3730 1550 1820 2500 2960 1420 1460 1700 2160 2800 3490 3960 4340

5000 313 K 333 K 353 K

y × 106

T (K) 313

[R-5] 106

3000

1000 150

250

350

P (bar)

Synonyms: Vitamin A; all-trans-Retinol; (all-E)3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)2,4,6,8-nonatetraen-1-ol Source: Johannsen, M. ; Brunner, G. J. Chem. Eng. Data (1997), 42(1), 106-111.

Rhodium tris(diisopropyldithiocarbamate) (C21H42N3RhS6; FW=631.87)

333.15

343.15

150 200 250 300 350 400 150 200 250 300 350 400 150 200 250 300

M x 10 (mol/L)

64.4 92.6 137.9 168.4 217.4 243.7 41.1 72.2 133.5 218.5 288.8 336.3 20.9 122.7 208.5 284.1

[R-6]

y1) x 106 4.04 5.19 7.26 8.50 10.60 11.60 2.98 4.38 7.45 11.60 14.70 16.60 1.80 8.16 12.40 15.80

20

323.15 K 333.15 K 343.15 K

6

323.15

P (bar)

y × 10

T (K)

6

10

0 100

CAT4240—CHAPTER 18—1/11/2006—18:46—SRIDHAR—XML MODEL C – pp. 699–705

250 P (bar)

400

704

Solubility in Supercritical Carbon Dioxide

350 339.9 18.10 400 381.5 19.60 1: Calculated from M. Synonym: Tris(diisopropyldithiocarbamato)rhodium Source: Wenclawiak, B.W.; Wolf, A.; Wilnewski, S. in: Supercritical Fluids as Solvents and Reaction Media, Brunner, G. (ed.), Elsevier B.V., Amsterdam, Netherlands (2004), 323-340. (Another source: Wolf, A.: Sc.D. Thesis, Siegen University, Germany, 1999.)

Rhodium tris(methylthioglycolate) (C9H15O6RhS3; FW=418.31) T (K)

P (bar)

M × 106 (mol/L)

[R-7]

y1) × 106

150 69.1 4.33 15 200 106.0 5.93 250 120.3 6.33 300 136.0 6.86 350 144.4 7.05 10 400 152.8 7.27 333.15 150 50.2 3.64 200 127.7 7.74 250 152.8 8.53 5 300 169.5 8.97 350 196.7 10.00 400 209.3 10.30 343.15 150 35.6 3.07 0 200 150.7 10.00 100 250 201.9 12.00 300 230.2 12.80 350 249.0 13.20 400 275.2 14.10 1: Calculated from M. Synonyms: Rh(MTG)3; Tris(methylthioglycolato)rhodium Source: Wenclawiak, B.W.; Wolf, A.; Wilnewski, S. in: Supercritical Fluids as Solvents and Reaction Media, Brunner, G. (ed.), Elsevier B.V., Amsterdam, Netherlands (2004), 323-340. (Another source: Wolf, A.: Sc.D. Thesis, Siegen University, Germany, 1999.)

y × 106

323.15

CAT4240—CHAPTER 18—1/11/2006—18:46—SRIDHAR—XML MODEL C – pp. 699–705

323.15 K 333.15 K 343.15 K

250 P (bar)

400

Solubility Data R

705

Rhodium tris(2,2,6,6-tetramethyl-3,5-heptanedionate) (C33H57O6Rh; FW=652.72) [R-8] P (bar)

323.15

150 200 250 300 350 400 150 200 250 300 350 400 150 200 250 300 350 400

333.15

343.15

M x 106 (mol/L)

y1) × 106

143.7 158.1 176.8 190.7 210.8 222.3 131.0 171.7 219.2 275.7 291.0 302.8 120.2 218.7 302.8 351.6 366.0 377.3

9.00 8.85 9.31 9.62 10.30 10.60 9.48 10.40 12.20 14.60 14.80 14.90 10.40 14.50 18.00 19.60 19.50 19.30

323.15 K 333.15 K 343.15 K

20

y × 106

T (K)

15

10

5 100

250

400

P (bar)

1: Calculated from M. Synonym: Tris(2,2,6,6-tetramethyl-3,5-heptanedionato)rhodium Source: Wenclawiak, B.W.; Wolf, A.; Wilnewski, S. in: Supercritical Fluids as Solvents and Reaction Media, Brunner, G. (ed.), Elsevier B.V., Amsterdam, Netherlands (2004), 323-340. (Another source: Wolf, A.: Sc.D. Thesis, Siegen University, Germany, 1999.)

Rosemary Oil 310.15

320.15

[R-9]

P (bar) 100 120 140 160 100 120 140 160

w × 106 1750 2450 2150 2000 535 1280 2400 2800

Source: Coelho, L. A. F.; Oliveira, J. V.; D'Avila, S. G.; Vilegas, J. H. Y.; Lancas, F. M. J. High Resol. Chromatogr. (1997), 20(8), 431-436.

4000

w × 106

T (K)

310.15 K 320.15 K

2000

0 50

CAT4240—CHAPTER 18—1/11/2006—18:46—SRIDHAR—XML MODEL C – pp. 699–705

100

150 P (bar)

200

19

Solubility Data S

Salen (C16H16N2O2; MW=268.31) T (K)

P1)

(bar)

y1)

[S-1]

6

x 10

70.9 920 102.0 1420 142.4 1970 182.1 2430 203.0 2680 304.1 3220 334.15 142.4 690 181.3 2600 201.5 3480 301.0 4870 1: Obtained by digitizing the graph in the original article. Synonym: N,N'-Bis(salicylidene)-1,2ethanediamine; a ,a'-Ethylenedinitrilodi-o-cresol Source: Koh, S.; Jeon, B.; Kim, H.; Park, K.; Kim, H. Bull. Korean Chem. Soc. (2004), 25(4), 471-474.

y x 106

294.15

6000 294.15 K 334.15 K

3000

0 0

100

200 P (bar)

[S-2]

Salinomycin sodium salt (C42H69NaO11; FW=772.99) T (K)

P (bar)

Water1)

y x 106

185 0 17.0 249 0 53.9 318 0 130.0 391 0 151.0 353.15 142 0 26.1 202 0 46.7 256 0 112.0 273 0 126.0 318 0 271.0 395 0 395.0 333.15 175 Saturated 17.7 184 Saturated 38.2 243 Saturated 132.0 313 Saturated 176.0 326 Saturated 309.0 404 Saturated 295.0 1: Cosolvent in CO2. Source: Maxwell, R.; Hampson, J.; CygnarowiczProvost, M. J. Supercrit. Fluids (1992), 5(1), 31-37.

450

343 K, CO2 353 K, CO2 333 K, Sat'd H2O

300

y x 106

343.15

300

150

0 100

200

300

400

P (bar)

707

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708

Solubility in Supercritical Carbon Dioxide

[S-3]

Shale oil1)

w x 106

P2) (bar) S3) (g/L) w4) x 106 T (K) 100000 28.6 38900 323 151.0 42.5 49200 232.5 297.5 61.3 65800 11.2 21600 348 158.9 41.3 55700 238.9 50000 38.6 51900 242.4 61.3 72600 315.7 3.8 10100 373 160.3 27.5 44900 246.2 0 333.3 64.3 84000 150 1: An atmospheric residue of shale oil originating from Aleksinac oil shale (Yugoslavia). 2: Calculated from density (obtained by digitizing the graph) and temperature. 3: Obtained by digitizing the graph in the original article. 4: Calculated from S. Source: Sokic, M.; Skala, D. J. Serb. Chem. Soc. (1992), 57(5-6), 353-357.

323 K 348 K 373 K

250

350

P (bar)

Simazine (C7H12ClN5; MW=201.66)

333.15

y1) x 106 35 50 48 46 56 55 51 51 54 54 58 61 63 17 37 75 92 96 101 106 123 142 164

200

yx

P (bar) 102.6 115.5 131.9 139.2 141.2 154.7 169.5 181.9 201.6 232.4 252.7 282.8 289.3 108.0 125.4 154.7 178.3 193.3 206.6 229.4 265.1 284.3 291.3

106

T (K) 313.15

[S-4]

313.15 K 333.15 K 353.15 K

100

0 50

150

CAT4240—CHAPTER 19—31/10/2006—19:30—KADAMBADI—XML MODEL C – pp. 707–734

250 P (bar)

350

Solubility Data S

709

353.15

108.0 24 127.8 37 139.7 67 141.7 75 160.6 116 179.3 126 192.8 140 216.1 147 229.4 157 255.1 173 294.2 193 1: Obtained by digitizing the graph in the original article. Synonym: 2-Chloro-4,6-bis(ethylamino)-1,3,5-triazine Source: Knez, Z.; Rizner-Hras, A.; Kokot, K.; Bauman, D. Fluid Phase Equil. (1998), 152(1), 95-108.

[S-5]

Skatole (C9H9N; MW=131.17) T (K)

P (bar)

y x 106

4000

75.2 161 80.0 397 83.8 1260 90.4 1830 109.0 2430 132.0 2760 167.0 3150 190.0 3230 Synonym: 3-Methylindole Source: Sako, S.; Shibata, K.; Ohgaki, K.; Katayama, T. J. Supercrit. Fluids (1989), 2(1), 3-8.

y x 106

308.15

2000

0 50

100

150 P (bar)

[S-6]

Soybean oil1) T (K) 345.15

P (bar)

200

y x 106

y x 106

345 680 552 3980 690 14950 1103 37490 1400 34230 1: A refined, bleached and deodorized commercial soybean oil. Source: Eissler, R.; Friedrich, J. P. J. Am. Oil Chem. Soc. (1988), 65(5), 764-767.

50000 25000 0 0

500

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1000 P (bar)

1500

710

Solubility in Supercritical Carbon Dioxide

Squalane (C30H62; MW=422.81)

[S-7] 5000 y x 106

y x 106 P (bar) 140.0 1560 110.5 410 142.0 1390 142.0 1420 202.0 3100 232.0 3890 Synonym: 2,6,10,15,19,23Hexamethyltetracosane Source: Schmitt, W. J.; Reid, R. C. Chem. Eng. Comm. (1988), 64, 155-176. T (K) 310 320

310K 320K

2500 0 100

150

200

250

P (bar)

Squalane (C30H62; MW=422.81)

[S-8]

106

6000

303.2 K 308.2 K 318.2 K 328.5 K

4000

y x 106

yx T (K) P (bar) 303.2 79.1 570 90.9 900 98.7 1090 167.5 2000 196.4 2400 245.5 2900 254.7 3100 265.2 3000 308.2 83.4 260 95.3 740 118.2 1330 157.6 2000 196.3 2700 245.6 3300 255.3 3500 318.2 91.6 51 96.6 96 109.7 460 117.7 790 118.3 740 157.4 1910 162.4 2000 167.5 2200 206.4 3100 215.5 3600 245.4 4100 275.0 4500 328.5 146.4 1050 162.2 1680 176.2 2300 176.9 2200 212.6 3600 216.1 3700 250.4 4800 Synonym: 2,6,10,15,19,23-Hexamethyltetracosane Source: Sovova, H.; Jez, J.; Khachaturyan, M. Fluid Phase Equil. (1997), 137(1-2), 185-191.

2000

0 50

CAT4240—CHAPTER 19—31/10/2006—19:30—KADAMBADI—XML MODEL C – pp. 707–734

150 P (bar)

250

Solubility Data S

711

[S-9]

Squalane (C30H62; MW=422.81) S (g/L) 2.10 5.80 11.76 16.94 14.65 18.31 17.91 21.71 19.11 23.42 27.67 25.49 28.72 31.18 37.10 41.44 47.12 50.34 54.12 58.73 66.07 79.04 83.35 90.13 101.40 107.22 106.89 104.03 98.45 58.95 101.75 145.53 158.62 161.85 171.19 173.15 176.57 169.69 152.99 5.43 7.26 14.39

367 899 1710 2364 2045 2501 2447 2937 2586 3102 3614 3330 3693 3953 4606 5065 5669 6010 6377 6848 7577 8794 9182 9774 10670 10950 10790 10270 9543 7107 11370 15400 16550 16830 17570 17690 17900 16820 14920 958 1232 2227

30000 323.6 K 328.5 K 343.2 K 362.8 K 382.3 K

20000 y x 106

T (K) P (bar) 323.6 122.0 140.0 157.0 172.5 172.5 182.5 182.5 187.5 187.5 200.0 209.0 209.0 220.5 232.0 251.0 267.0 285.0 294.5 312.0 327.0 353.0 409.0 430.0 466.5 550.0 650.0 700.0 800.0 900.0 328.5 310.0 431.0 560.0 600.0 610.0 653.0 670.0 700.0 800.0 890.0 343.2 171.0 179.0 205.0

y1) x 106

10000

0 0

200 400

CAT4240—CHAPTER 19—31/10/2006—19:30—KADAMBADI—XML MODEL C – pp. 707–734

600 800

P (bar)

1000

712

Solubility in Supercritical Carbon Dioxide

205.0 14.56 2253 215.0 17.24 2598 215.0 17.17 2588 222.5 20.90 3094 222.5 20.31 3007 233.0 24.14 3495 233.0 24.08 3486 250.0 31.54 4425 262.0 37.92 5218 271.0 42.44 5763 282.5 47.17 6307 292.0 53.33 7045 300.0 60.13 7866 308.5 62.84 8144 322.0 73.10 9336 338.0 86.07 10820 345.0 93.45 11660 353.0 99.76 12360 380.0 132.75 16060 390.0 159.85 19140 400.0 201.31 23830 362.8 206.0 7.55 1418 215.0 8.63 1562 230.0 12.50 2145 240.0 14.82 2468 240.0 15.98 2661 255.0 22.09 3536 255.0 22.65 3625 270.0 28.81 4458 285.0 36.94 5548 300.0 47.64 6968 325.0 72.27 10170 343.0 92.20 12650 350.0 101.10 13750 365.0 120.58 16100 369.0 194.76 25650 371.0 209.31 27460 382.3 260.0 14.73 2691 260.0 15.18 2773 280.0 22.77 3936 290.0 25.69 4335 290.0 27.37 4617 300.0 34.16 5633 320.0 48.76 7720 330.0 57.44 8928 340.0 70.17 10710 350.0 88.47 13270 360.0 110.74 16330 368.0 153.44 22250 1: Calculated from S. Synonym: 2,6,10,15,19,23-Hexamethyltetracosane Source: Swaid, I.; Nickel, D.; Schneider, G. M. Fluid Phase Equil. (1985), 21(1-2), 95-112.

CAT4240—CHAPTER 19—31/10/2006—19:30—KADAMBADI—XML MODEL C – pp. 707–734

Solubility Data S

713

Squalane (C30H62; MW=422.81)

303.15

P (bar) 90

100

313.15

100

Ethanol1) (mol%)

y x 106

0.0 0.2 0.3 0.8 2.2 2.9 3.3 3.5 0.0 2.0 5.7 6.7 8.0 0.0 0.4 5.1 6.1 6.7 8.1 9.2 11.2

900 900 1100 1200 1900 2300 2400 2700 1100 2100 3900 4800 5300 500 600 2200 2600 2800 3200 3900 4300

6000

4000 y x 106

T (K)

[S-10]

2000 303 K, 90 bar 303 K, 100 bar 313 K, 100 bar

0 0

4

8

12

Ethanol (mol%)

1: Cosolvent in CO2. Synonym: 2,6,10,15,19,23-Hexamethyltetracosane Source: Sovova, H.; Rat, V.; Khachaturyan, M.; Vlcek, D. J. Supercrit. Fluids (1999), 14(2), 145-149.

Squalane(C30H62; MW=422.81) T (K)

[S-11] 5000

P (bar) n-Heptane1) y x 106 (mol%) 90

100

0.0 0.7 0.9 1.3 3.0 0.0 0.5 0.6 0.9 1.0 1.7 1.9 2.1 2.1

900 1600 1800 2200 4600 1100 1700 1900 2400 2400 3300 3600 3900 4200

4000

y x 106

303.15

3000 2000 303 K, 90 bar 303 K, 100 bar 313 K, 100 bar

1000 0

0

1 2 3 n-Heptane (mol%)

CAT4240—CHAPTER 19—31/10/2006—19:30—KADAMBADI—XML MODEL C – pp. 707–734

4

714

313.15

Solubility in Supercritical Carbon Dioxide

100

0.0 0.8 1.7 2.1 2.2 3.4 3.6 3.8

500 1100 1900 2400 2600 3600 4300 4900

1: Cosolvent in CO2. Synonym: 2,6,10,15,19,23-Hexamethyltetracosane Source: Sovova, H.; Rat, V.; Khachaturyan, M.; Vlcek, D. J. Supercrit. Fluids (1999), 14(2), 145-149.

Squalane(C30H62; MW=422.81)

303.15

P (bar) 90

100

313.15

100

Toluene1) (mol%) 0.0 1.2 2.2 2.4 2.5 2.7 3.0 3.3 3.7 4.0 4.1 0.0 0.4 1.6 2.0 2.2 2.3 2.3 2.5 2.7 3.6 0.0 0.5 0.7 1.6 2.2 2.9 3.2

y x 106 900 1900 2700 2900 2900 3200 3500 3800 4500 4800 5000 1100 1500 2600 2900 3000 3100 3200 3300 3500 4500 500 800 900 1400 1800 2500 3100

6000

303 K, 90 bar 303 K , 100 bar 313 K , 100 bar

4000 y x 106

T (K)

[S-12]

2000

0 0

1

1: Cosolvent in CO2. Synonym: 2,6,10,15,19,23-Hexamethyltetracosane Source: Sovova, H.; Rat, V.; Khachaturyan, M.; Vlcek, D. J. Supercrit. Fluids (1999), 14(2), 145-149.

CAT4240—CHAPTER 19—31/10/2006—19:30—KADAMBADI—XML MODEL C – pp. 707–734

2

3

Toluene (mol%)

4

Solubility Data S

715

Squalene (C30H50; MW=410.72) T (K)

P (bar)

W (g/kg CO2)

[S-13] 6000

y1) x 106

323 K 333 K

0.27 29 100 10.63 1140 150 3000 17.38 1860 175 23.84 2550 200 30.12 3220 225 27.05 2890 333 225 0 34.65 3700 250 50 43.00 4590 275 300 47.70 5090 1: Calculated from W. Synonym: (all-E )-2,6,10,15,19,23-Hexamethyl2,6,10,14,18,22-tetracosahexaene Source: Catchpole, O. J. ; Grey, J. B. ; Noermark, K. A. J. Chem. Eng. Data (1998), 43(6), 1091-1095.

y x 106

323

150

250 P (bar)

Squalene (C30H50; MW=410.72) T (K)

P (bar)

Ethanol1) (wt%)

W2)

(g/kg CO2)

[S-14] y3) x 106

45.22 4600 5.16 72.07 7090 8.47 10600 12.04 111.30 61.14 6250 333 250 4.28 85.28 8530 6.51 14140 9.74 146.30 14920 10.28 155.30 78.83 8060 333 275 4.07 13310 6.78 134.10 9.41 236.90 22760 1: Cosolvent in CO2 on a solute-free basis. 2: Mass solubility on a cosolvent-free basis. 3: Calculated from W on a solute-free basis. Synonym: (all-E )-2,6,10,15,19,23-Hexamethyl2,6,10,14,18,22-tetracosahexaene Source: Catchpole, O. J. ; Grey, J. B. ; Noermark, K. A. J. Chem. Eng. Data (1998), 43(6), 1091-1095. 200

y x 106

333

350

200 bar 250 bar 275 bar

20000

10000

0 0

CAT4240—CHAPTER 19—31/10/2006—19:30—KADAMBADI—XML MODEL C – pp. 707–734

5

10

Ethanol (wt%)

15

716

Solubility in Supercritical Carbon Dioxide

Stearic acid (C18H36O2; MW=284.48) T (K)

P (bar)

S (g/L)

1)

[S-15]

6

y x 10

3000

101.3 1.02 246 152.0 1.53 301 253.3 1.90 333 333.15 101.3 1.97 1012 121.6 4.19 1434 152.0 5.16 1296 253.3 12.01 2342 1: Calculated from S. Synonym: Octadecanoic acid Source: Chrastil, J. J. Phys. Chem. (1982), 86(15), 3016-3021.

y x 10

6

313.15

313.15 K 333.15 K

2000 1000 0 50

150

250

P (bar)

Stearic acid (C18H36O2; MW=284.48)

[S-16]

6

6

150 y x 10

y x 10 T (K) P (bar) 308.15 90 25 99 41 119 64 139 83 159 94 178 104 208 121 237 132 Synonym: Octadecanoic acid Source: Iwai, Y.; Koga, Y.; Maruyama, H.; Arai, Y. J. Chem. Eng. Data (1993), 38(4), 506-508.

100 50 0 0

100

200

300

P (bar)

Stearic acid (C18H36O2; MW=284.48)

328

338

P (bar) 145.4 159.4 183.3 217.7 261.6 361.5 154.8 160.3 228.0 285.2 359.5 467.5 161.5 207.8 256.1

y × 106 791 935 979 963 1010 870 621 774 3860 5380 6290 7020 813 2260 3720

15000

y × 106

T (K) 318

[S-17] 318 K 328 K 338 K

10000

5000

0 100

200

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300 P (bar)

400

500

Solubility Data S

717

360.5 9240 463.8 14700 Synonym: Octadecanoic acid Source: Kramer, A.; Thodos, G. J. Chem. Eng. Data (1988), 33(3), 230-234.

Stearic acid (C18H36O2; MW=284.48) T (K)

P (bar)

W (g/kg CO2)

[S-18] 6000

y1) × 106

141 0.90 139 273 0.93 144 405 0.55 85 4000 313 138 0.28 43 207 1.40 217 276 0.90 1397 318 140 1.20 186 275 4.10 633 2000 412 4.00 618 323 138 0.96 148 207 1.50 232 276 5.10 788 328 139 7.10 1100 0 275 22.00 3390 100 400 33.00 5080 1: Calculated from W. Synonym: Octadecanoic acid Source: Maheshwari, P.; Nikolov, Z.; White, T.; Hartel, R. J. Am. Oil Chem. Soc. (1992), 69(11), 1069-1076.

308 K 313 K 318 K 323 K 328 K

y × 106

308

200

300 P (bar)

Stearic acid (C18H36O2; MW=284.48) T (K)

[S-19]

P1) (bar) w1) × 106 y2) × 106

1000

313.15

y × 106

138 900 139 206 2790 433 274 1860 288 323.15 139 930 144 207 1860 288 276 4650 722 1: Obtained by digitizing the graph in the original article. 2: Calculated from w. Synonym: Octadecanoic acid Source: Nikolov, Z.; Maheshwari, P.; Hardwick, J.; Murphy, P.; Johnson, L. Develop. Food Sci. (1992), 29, 595-616.

400

313.15 K 323.15 K

500

0 100

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200 P (bar)

300

718

Solubility in Supercritical Carbon Dioxide

Stearic acid (C18H36O2; MW=284.48)

[S-20]

106

1200

y × 106

y× P (bar) 113.5 423 114.0 475 142.0 237 143.5 193 202.0 229 202.0 259 282.0 232 283.0 260 364.0 246 320 113.5 190 114.0 213 142.0 605 143.5 592 202.0 772 202.0 1070 282.0 940 283.0 1040 364.0 988 Synonym: Octadecanoic acid Source: Schmitt, W. J.; Reid, R. C. Chem. Eng. Comm. (1988), 64, 155-176. T (K) 310

800 310 K 320 K

400

0 100

200

300 P (bar)

Stearic acid (C18H36O2 ; MW=284.48)

318.15

P (bar) 95

110

125

145

[S-21] 3000

Cosolvent1) y × 106 (mol%) 0.00 1.23 3.47 4.32 5.82 0.00 1.05 3.17 5.21 0.00 1.24 2.30 3.73 4.50 6.82 0.00

46 141 525 794 1380 115 195 617 1290 182 316 537 955 1150 2140 251

y × 106

T (K)

400

95 bar 110 bar 125 bar 145 bar 160 bar

2000

1000

0

0

2 4 6 Cosolvent mixture (mol%)

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Solubility Data S

719

457 1.62 1000 3.53 1620 4.98 2190 6.85 316 160 0.00 575 1.52 1480 3.39 5.21 2240 1: Equimolar mixture of ethanol and acetonitrile. Synonym: Octadecanoic acid Source: Guan, B.; Han, B.; Yan, H. Fluid Phase Equil. (1998), 149(1-2), 277-286.

Stearic acid (C18H36O2 ; MW=284.48) T (K)

P (bar)

[S-22]

Cosolvent1) y × 106 (mol%)

4000

46 0.00 251 1.35 617 3.11 3000 1070 4.48 115 110 0.00 331 1.05 955 2.89 2000 1660 4.37 182 125 0.00 617 1.31 1000 1170 2.68 2000 4.45 251 145 0.00 759 1.08 0 1320 2.51 0 2340 4.59 316 160 0.00 1170 1.32 1780 2.45 4.43 3240 1: Equimolar mixture of acetic acid and acetonitrile. Synonym: Octadecanoic acid Source: Guan, B.; Han, B.; Yan, H. Fluid Phase Equil. (1998), 149(1-2), 277-286. 95

y × 106

318.15

95 bar 110 bar 125 bar 145 bar 160 bar

1

2

3

4

Cosolvent mixture (mol%)

CAT4240—CHAPTER 19—31/10/2006—19:30—KADAMBADI—XML MODEL C – pp. 707–734

5

720

Solubility in Supercritical Carbon Dioxide

Stearic acid (C18H36O2; MW=284.48)

308.2

P (bar) 99

148

197

(mol%)

0.00 1.42 2.59 4.02 4.28 4.47 5.15 6.26 6.26 7.56 0.00 0.47 1.60 2.18 3.85 4.16 4.24 6.73 7.63 8.75 0.00 1.67 2.59 2.78 3.07 3.30 3.40 3.61 3.78 5.63 6.45 6.50 6.54

[S-23]

y x 106 41 163 323 447 725 678 1140 1390 1540 1650 88 105 344 447 867 862 1020 2250 2740 3040 115 383 643 688 924 814 850 849 933 2150 2020 2160 2250

99 bar

3000

148 bar 197 bar

y × 106

T (K)

Ethanol1)

2000

1000

0

0

1: Cosolvent in CO2. Synonym: Octadecanoic acid Source: Koga, Y.; Iwai, Y.; Hata, Y.; Yamamoto, M.; Arai, Y. Fluid Phase Equil. (1996), 125, 115-128.

CAT4240—CHAPTER 19—31/10/2006—19:30—KADAMBADI—XML MODEL C – pp. 707–734

5 Ethanol (mol%)

10

Solubility Data S

721

Stearic acid (C18H36O2; MW=284.48)

308.2

P (bar) 99

197

(mol%)

0.00 1.02 1.10 1.16 1.38 1.99 2.59 4.19 6.55 8.15 8.83 0.00 1.17 3.25 3.75 4.79 6.39 7.24 7.69 7.71

[S-24]

y × 106 41 50 62 58 71 100 112 246 513 744 901 115 164 377 344 626 964 1200 1250 1070

1500

99 bar 197 bar

1000 y × 106

T (K)

Octane1)

500

0

0

10

5 Octane (mol%)

1: Cosolventin CO2. Synonym: Octadecanoic acid Source: Koga, Y.; Iwai, Y.; Hata, Y.; Yamamoto, M.; Arai, Y. Fluid Phase Equil. (1996), 125, 115-128.

Stearic acid (C18H36O2; MW=284.48)

323.15

323.15

323.15

P (bar) 107 137 175 213 242 103 170 202 250 260 118 148 180 209 232 255

0.0 0.0 0.0 0.0 0.0 Acetone 3.0 3.0 3.0 3.0 3.0 Methanol 3.0 3.0 3.0 3.0 3.0 3.0

78 290 780 930 1300 1700 1900 2000 2100 2200 30 100 300 400 600 700

2400

1600 Pure CO2 Acetone Methanol Water

y x 106

T (K)

[S-25]

Cosolvent 1) y × 106 (wt%)

800

0 50

CAT4240—CHAPTER 19—31/10/2006—19:30—KADAMBADI—XML MODEL C – pp. 707–734

150 P (bar)

250

722

Solubility in Supercritical Carbon Dioxide

Water 103 3.0 78 135 3.0 220 170 3.0 700 210 3.0 910 240 3.0 2100 1: Obtained by digitizing the graph in the original article. Some data may not be accurate as the source graph is in a semi-log scale with a small span. Synonym: Octadecanoic acid Source: Noh, M. J.; Kim, T. G.; Hong, I. K.; Yoo, K.-P. Korean J. Chem. Eng. (1995), 12(1), 48-55. 323.15

Stearic acid (C18H36O2; MW=284.48)

318.15

P (bar) 96

113

128

146

162

Acetic acid1) (mol %)

y x 106

0.00 0.45 1.35 1.51 1.96 2.80 0.00 0.60 1.13 1.39 1.98 2.62 3.04 0.00 0.60 1.26 1.64 1.98 2.95 0.00 0.61 1.61 2.16 3.07 0.00 0.62 1.61 2.01 3.13

49 237 395 403 585 935 135 493 715 893 1180 1580 1730 208 643 1270 1490 1400 2070 258 927 1570 2190 3480 281 1160 1780 2280 3500

4000 96 bar 113 bar 128 bar 146 bar 162 bar

3000 y × 106

T (K)

[S-26]

2000

1000

0

0

1: Cosolvent in CO2. Synonym: Octadecanoic acid Source: Zhong, M.; Han, B.; Yan, H. J. Supercrit. Fluids (1997), 10(2), 113-118.

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1 2 3 Acetic acid (mol%)

Solubility Data S

723

Stearic acid (C18H36O2; MW=284.48)

318.15

P (bar) 98

111

126

141

163

Ethanol (mol %) 0.00 0.69 1.42 2.29 0.00 0.67 1.56 2.61 0.00 0.62 1.57 2.83 0.00 0.70 1.49 2.70 0.00 0.71 1.80 2.58

y x 106 58 81 180 509 117 146 359 961 195 236 513 1316 244 336 597 1274 275 420 951 1480

[S-27] 1600 98 bar 111 bar 126 bar 141 bar 163 bar

1200 y × 106

T (K)

1)

800

400

0

0

1

2

3

Ethanol (mol%)

1: Cosolvent in CO2. Synonym: Octadecanoic acid Source: Zhong, M.; Han, B.; Yan, H.; Peng, D.-Y. Fluid Phase Equil. (1997), 134(1-2), 175-183.

Stearic acid (C18H36O2; MW=284.48)

318.15

P (bar) 96

116

130

Methyl acetate1) (mol %)

y x 106

0.00 0.66 1.70 1.86 3.56 3.84 5.14 0.00 0.62 2.05 3.65 5.03 0.00 1.41 1.45 1.54 2.23 3.75 5.32

49 73 118 124 291 357 988 155 166 255 444 1170 216 314 311 294 353 566 1260

1500 96 bar 116 bar 130 bar 151 bar 159 bar

1000 y × 106

T (K)

[S-28]

500

0

0

2

4

Methyl acetate (mol%)

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6

724

Solubility in Supercritical Carbon Dioxide

151

159

0.00 0.65 1.65 4.17 5.66 0.00 0.69 1.49 4.33 5.66

267 334 404 709 1400 281 353 411 854 1400

1: Cosolvent in CO2. Synonym: Octadecanoic acid Source: Zhong, M.; Han, B.; Yan, H. J. Supercrit. Fluids (1997), 10(2), 113-118.

Stearic acid (C18H36O2; MW=284.48)

318.15

P (bar) 96

110

125

135

145

165

(mol %) 0.00 0.54 1.58 2.71 3.77 0.00 0.60 0.61 1.58 2.68 3.76 0.00 0.66 1.54 2.75 3.86 0.00 0.59 1.66 3.91 0.00 0.62 1.63 2.77 3.96 0.00 0.60 1.60 3.87 3.93

[S-29]

y × 106 49 58 136 317 708 112 141 150 225 412 855 186 230 326 694 1247 230 255 405 1521 251 276 423 725 1571 282 355 522 1434 1538

96 bar 110 bar 125 bar 135 bar 145 bar 165 bar

1500

y × 106

T (K)

n-Octane1)

1000

500

0

0

1

2

3

n -Octane (mol%)

1: Cosolvent in CO2. Synonym: Octadecanoic acid Source: Zhong, M.; Han, B.; Yan, H.; Peng, D.-Y. Fluid Phase Equil. (1997), 134(1-2), 175-183.

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4

Solubility Data S

725

Stearyl alcohol (C18H38O; MW=270.49) 308.15

y×

P (bar) 90 104 120 139 159 178 198 218 237

1000

224 407 525 700 721 782 812 828 900

y × 106

T (K)

[S-30]

106

500 0 50

100

150

200

P (bar)

Synonyms: 1-Octadecanol; n-Octadecyl alcohol Source: Iwai, Y.; Koga, Y.; Maruyama, H.; Arai, Y. J. Chem. Eng. Data (1993), 38(4), 506-508.

Stearyl alcohol (C18H38O; MW=270.49)

308.2

P (bar)

99

148

197

Ethanol1) (mol%)

0.00 2.00 2.26 3.61 6.91 7.02 7.10 0.00 0.49 2.13 4.26 4.43 4.57 6.52 7.26 0.00 1.46 3.85 4.71 6.79 7.79 9.03

[S-31]

y × 106

342 550 620 1050 3090 2580 3630 714 714 1100 2150 2440 2740 4120 4230 811 965 2290 2750 4110 5430 6820

8000 99 bar 148 bar 197 bar

6000 y × 106

T (K)

250

4000

2000

0

0

2

1: Cosolvent in CO2. Synonyms: 1-Octadecanol; n-Octadecyl alcohol Source: Koga, Y.; Iwai, Y.; Hata, Y.; Yamamoto, M.; Arai, Y. Fluid Phase Equil. (1996), 125, 115-128.

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4

6

Ethanol (mol%)

8

10

726

Solubility in Supercritical Carbon Dioxide

Stearyl alcohol (C18H38O; MW=270.49)

308.2

P (bar) 99

197

(mol%)

0.00 0.63 1.34 3.47 4.86 5.54 6.60 6.69 0.00 1.32 1.34 1.74 2.55 2.81 3.65 3.81 4.14 5.69 6.57 6.66

[S-32]

y × 106 342 485 637 1380 1780 2480 3070 3100 811 1120 1160 1310 1520 1650 1880 1890 2180 3390 3480 3800

4000 99 bar 197 bar

3000 y × 106

T (K)

Octane1)

2000

1000

0

0

2 4 Octane (mol%)

6

1: Cosolvent in CO2. Synonyms: 1-Octadecanol; n-Octadecyl alcohol Source: Koga, Y.; Iwai, Y.; Hata, Y.; Yamamoto, M.; Arai, Y. Fluid Phase Equil. (1996), 125, 115-128.

Stigmasterol (C29H48O; MW=412.69)

313.15

323.15

313.15

313.15

P (bar) 101 140 166 200 234 132 165 206 241 103 140 172 236 98 140

Cosolvent 1) y × 106 (wt%) 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 Acetone 3.0 3.0 3.0 3.0 Methanol 3.0 3.0

6.3 9.4 10.0 25.0 38.0 1.0 13.0 44.0 56.0 9.4 38.0 50.0 63.0

CO2 313 K CO2 323 K Acet 313 K MeOH 313 K Water 313 K

60

y × 106

T (K)

[S-33]

40

20

0

50

100

8.3 13.0

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150 P (bar)

200

250

Solubility Data S

727

180 210 240

3.0 25.0 3.0 25.0 3.0 38.0 Water 313.15 103 3.0 1.0 139 3.0 1.9 172 3.0 3.8 200 3.0 5.0 231 3.0 5.5 240 3.0 7.5 1: Obtained by digitizing the graph in the original article. Some data may not be accurate as the source graph is in a semi-log scale with a small span. Synonym: (3b,22E)-Stigmasta-5,22-dien-3-ol Source: Noh, M. J.; Kim, T. G.; Hong, I. K.; Yoo,K.-P. Korean J. Chem. Eng. (1995), 12(1), 48-55.

Stigmasterol (C29H48O; MW=412.69)

308.15

323.15

333.15

308.15

P (bar) 91.1 122.6 152.1 181.9 203.0 256.1 276.6 121.6 152.0 182.4 202.7 253.3 304.0 121.5 152.0 182.4 202.7 253.3 304.0 100.7 121.6 152.0 182.0 203.7 252.7 274.3 304.0

Cosolvent 6 y × 10 (mol%) 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 Acetone 3.5 3.5 3.5 3.5 3.5 3.5 3.5 3.5

2.85 5.71 8.06 9.57 10.70 16.30 17.50 2.78 7.33 14.60 21.00 29.20 36.60 4.87 10.80 19.70 27.60 38.00 58.70 8.64 10.40 14.10 16.50 21.60 25.10 27.90 29.80

CO2, 308.2 K CO2, 323.2 K CO2, 333.2 K Acet, 308.2 K EtOH, 308.2 K MeOH, 308.2 K

60

y × 106

T (K)

[S-34]

40

20

0

0

100

CAT4240—CHAPTER 19—31/10/2006—19:30—KADAMBADI—XML MODEL C – pp. 707–734

200 P (bar)

300

400

728

Solubility in Supercritical Carbon Dioxide

Ethanol 3.5 18.60 3.5 22.80 3.5 32.50 3.5 43.10 3.5 53.80 3.5 63.30 Methanol 3.5 101.4 5.95 3.5 123.9 7.45 3.5 152.0 9.73 3.5 153.9 9.84 3.5 182.2 12.10 3.5 182.4 12.30 3.5 201.7 13.40 3.5 203.1 13.40 3.5 253.3 17.60 3.5 273.9 18.10 3.5 303.9 20.50 Synonym: (3b, 22E)-Stigmasta-5,22-dien-3-ol Source: Wong, J. M.; Johnston, K. P. Biotech. Prog. (1986), 2(1), 29-39. 101.9 122.2 151.6 204.2 252.6 354.7

Sucrose(C12H22O11; MW=342.30) T (K)

313.15

P1) (bar) (μg/Nl2))

296 500 1000 1500 2000

0.579 0.785 1.076 1.364 1.303

[S-35]

y3) × 106

0.0377 0.0511 0.0700 0.0887 0.0847

1: Obtained by digitizing the graph in the original article. 2: "Nl" means "Normliter," which is one liter at 273.15 K and 1 atm. 3: Calculated from S. Synonyms: Saccharose; (+)-Sucrose Source: Stahl, E.; Schilz, W. Chem. Ing. Tech. (1978), 50(7), 535-537.

0.10 y × 106

S1)

0.06

0.02 0

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1000 P (bar)

2000

Solubility Data S

729

Surfactant Ls-361) (C36H74O10; MW=666.98) 308.2

318.2

P (bar) M (mol/L) y2) × 106 111.0 145.0 167.3 187.1 197.4 153.1 175.6 197.8 213.3

0.01 0.02 0.03 0.04 0.05 0.01 0.02 0.03 0.04

3000

590 1090 1580 2050 2540 590 1120 1620 2120

308.2 K 318.2 K

y × 106

T (K)

[S-36]

1: A block copolymer of Henkel Corporation of Germany [(dodecyl oxide)(ethylene oxide)3-(propylene oxide)6]. 2: Calculated from M. Source: Liu, J.; Han, B.; Wang, Z.; Zhang, J.; Li, G.; Yang, G. Langmuir (2002), 18(8), 3086-3089.

1500

0 100

150

200

P (bar)

Surfactant Ls-451) (C35H72O10; MW=652.95)

318.2

P (bar) M (mol/L) y1) × 106 129.7 0.01 560 167.3 0.02 1050 193.2 0.03 1530 210.5 0.04 2010 164.6 0.01 570 201.1 0.02 1080 223.7 0.03 1570

1: A block copolymer of Henkel Corporation of Germany [(dodecyl oxide)(ethylene oxide)4-(propylene oxide)5]. 2: Calculated from M. Source: Liu, J.; Han, B.; Wang, Z.; Zhang, J.; Li, G.; Yang, G. Langmuir (2002), 18(8), 3086-3089.

2000 y × 106

T (K) 308.2

[S-37]

308.2 K 318.2 K

1000

0 100

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150

200 P (bar)

250

730

Solubility in Supercritical Carbon Dioxide

Surfactant Ls-541) (C34H74O10; MW=638.92)

318.15

(bar) 137 178 198 217 229 168 189 203 224

M2) (mol/L) 0.01 0.02 0.03 0.04 0.05 0.01 0.015 0.02 0.03

y3)

×

[S-38]

106

570 1050 1540 2000 2480 590 840 1090 1590

3000 y × 106

T (K) 308.15

P2)

308.15 K 318.15 K

1500

0 100

1: A block copolymer of Henkel Corporation of Germany [(dodecyl oxide)(ethylene oxide)5-(propylene oxide)4]. 2: Obtained by digitizing the graph in the original article. 3: Calculated from M. Source: Liu, J.; Han B.; Zhang, J.; Li, G.; Zhang, X.; Wang, J.; Dong, B. Chem. Eur. J. (2002), 8(6), 1356-1360.

150

200 P (bar)

[S-39]

Sulfadimethoxine(C12H14N4O4S; MW=310.33) 106

3 y × 106

y× T (K) P (bar) 313.15 100 2.69 150 2.40 200 2.32 250 2.27 300 2.14 400 2.26 Synonyms: 2,4-Dimethoxy-6sulfonylamido-1,3-diazine; 2,6Dimethoxy-4-sulfanilamidopyrimidine Source: Ashraf-Khorassani, M.; Combs, M.T.; Taylor, L.T.; Schweighardt, F.K.; Mathias, P. S. J. Chem. Eng. Data (1997), 42(3), 636-640.

250

2 0

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200 P (bar)

400

Solubility Data S

731

Sulfadimethoxine (C12H14N4O4S; MW=310.33)

[S-40]

105

S× y × 106 (mol/L) 313.15 131 2.06 1.22 166 3.06 1.67 196 3.74 1.97 3 235 4.36 2.21 275 5.45 2.68 320 5.58 2.66 358 5.69 2.67 2 391 5.59 2.58 437 5.94 2.69 466 6.09 2.73 1 333.15 202 0.43 0.26 237 1.70 0.98 270 3.85 2.10 306 4.47 2.35 0 342 4.78 2.45 100 377 5.33 2.67 414 5.81 2.85 449 6.21 2.99 488 6.50 3.08 Synonyms: 2,4-Dimethoxy-6-sulfonylamido-1,3diazine; 2,6-Dimethoxy-4-sulfanilamidopyrimidine Source: Hampson, J. W.; Maxwell, R. J.; Li, S.; Shadwell, R. J. J. Chem. Eng. Data (1999), 44(6),1222-1225. P (bar)

y × 106

T (K)

313 K 333 K

300 P (bar)

Sulfamerazine (C11H12N4O2S; MW=264.30)

[S-41]

105

S× y × 106 (mol/L) 313.15 151 0.58 0.33 188 2.03 1.08 4 236 3.23 1.63 292 4.55 2.21 327 4.92 2.34 362 5.25 2.45 407 5.41 2.48 433 6.02 2.71 2 474 6.22 2.78 333.15 202 0.33 0.20 224 1.67 0.97 249 3.00 1.68 290 5.06 2.71 0 321 6.33 3.30 100 345 7.17 3.67 384 8.22 4.10 420 7.12 4.46 472 10.14 4.83 Synonym: N-(4-Methyl-2-pyrimidyl)sulfanilamide Source: Hampson, J. W.; Maxwell, R. J.; Li, S.; Shadwell, R. J. J. Chem. Eng. Data (1999), 44(6), 1222-1225. P (bar)

313 K 333 K

y × 106

T (K)

500

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300 P (bar)

500

732

Solubility in Supercritical Carbon Dioxide

Sulfamethazine (C12H14N4O2S; MW=278.33) 3 y × 106

y × 106 T (K) P (bar) 313.15 100 2.23 150 2.18 200 2.04 250 2.09 300 2.08 400 2.11 Synonym: N1-(4,6-Dimethyl-2pyrimidinyl)sulfanilamide Source: Ashraf-Khorassani, M.; Combs, M. T.; Taylor, L. T.; Schweighardt, F. K.; Mathias, P. S. J. Chem. Eng. Data (1997), 42(3), 636-640.

[S-42]

2 1

0

200 P (bar)

Sulfamethazine (C12H14N4O2S; MW=278.33)

313.15

333.15

P (bar) 181 211 254 281 316 360 398 414 459 136 175 215 251 259 288 326 356 396 436 476

S× (mol/L) 1.65 2.32 3.30 3.81 4.18 4.30 4.51 4.72 4.91 1.62 2.37 2.86 3.29 3.52 3.86 4.46 4.65 5.25 5.62 6.59

[S-43]

y × 106 0.88 1.20 1.65 1.86 2.00 2.01 2.08 2.16 2.21 1.32 1.54 1.69 1.84 1.94 2.07 2.31 2.36 2.60 2.72 3.14

3

y × 106

T (K)

105

400

313 K 333 K

2

1

0 100

Synonym: N1-(4,6-Dimethyl-2-pyrimidinyl)sulfanilamide Source: Hampson, J. W.; Maxwell, R. J.; Li, S.; Shadwell, R. J. J. Chem. Eng. Data (1999), 44(6), 1222-1225.

CAT4240—CHAPTER 19—31/10/2006—19:30—KADAMBADI—XML MODEL C – pp. 707–734

300 P (bar)

500

Solubility Data S

733

Sulfathiazole (C9H9N3O2S2; MW=255.32)

313

353

P (bar) 100 150 200 250 350 100 150 175 200 250 300 100 150 200 250 300

y×

0.0012 0.0034 0.0040 0.0043 0.0013 0.0081 0.0093 0.0130 0.0110 0.0113 0.0085 0.0400 0.0518 0.0612 0.0605 0.0593

0.06 y × 106

T (K) 298

[S-44]

106

298 K 313 K 353 K

0.04

0.02

0.00

0

100

200

300

400

P (bar)

Synomyms: 2-(Sulfanilylamino)thiazole;N1-(2Thiazolyl)sulfanilamide Source: Kordikowski, A.; Siddiqi, M.; Palakodaty, S. Fluid Phase Equil. (2002), 194-197, 905-917.

Sulfathiazole (C9H9N3O2S2; MW=255.32) P (bar)

298

200

313

100

150

200

18

Methanol1) y × 106 (mol%) 0.99 1.96 3.84 7.39 13.76 2.01 3.95 5.81 7.59 9.32 10.97 12.57 14.12 1.98 3.89 7.48 13.92 1.96 7.39 13.76

0.011 0.071 0.860 3.790 9.460 0.026 0.170 0.660 1.230 4.810 8.470 13.800 15.600 0.029 0.170 1.190 9.100 0.033 1.290 6.510

y × 106

T (K)

[S-45] 100 bar 150 bar 200 bar

12

6

0

0

5

10

Methanol (mol%)

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15

734

Solubility in Supercritical Carbon Dioxide

100

200

0.99 1.47 1.96 2.43 0.99 1.96 3.84 7.39

0.033 0.035 0.036 0.051 0.054 0.056 0.180 0.500

12

y × 106

353

298 K 313 K 353 K

8

200 bar

4

1: Cosolvent in CO2. Synomyms: 2-(Sulfanilylamino)thiazole; N1-(2Thiazolyl)sulfanilamide Source: Kordikowski, A.; Siddiqi, M.; Palakodaty, S. Fluid Phase Equil. (2002), 194-197, 905-917.

0

0

5 10 Methanol (mol%)

Syringic acid (C9H10O5; MW=198.17) y × 106 P (bar) 100 0.315 150 1.221 200 1.874 250 2.494 300 3.009 350 3.776 400 4.470 450 4.892 500 5.641 323 100 0.058 150 1.260 200 2.606 250 3.857 300 4.459 350 5.852 400 6.953 450 8.006 500 9.210 333 100 0.001 150 1.550 200 3.034 250 4.468 300 6.067 350 7.559 400 9.629 450 11.106 500 12.709 Synonym: Gallic acid 3,5-dimethyl ether; 4Hydroxy-3,5-dimethoxybenzoic acid Source: Murga, R.; Sanz, M.- T.; Beltran, S.; Cabezas, J.- L. J. Chem. Eng. Data (2004), 49(4), 779-782.

15

[S-46]

T (K) 313

15 313 K 323 K 333 K

y × 106

10

5

0

0

200

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400 P (bar)

600

20

Solubility Data T

Taxol (C47H51NO14; MW=853.91)

313.15

318.15

207 276 345 483 207 276 345 483 207 276 345 483

y x 10

0.07 0.14 0.23 0.41 0.07 0.14 0.23 0.44 0.07 0.15 0.25 0.50

0.6

6

P (bar)

0.4

308 K 313 K 318 K

y x 10

T (K) 308.15

[T-1]

6

0.2

0 100

200

300

400

P (bar)

Synonym: Paclitaxel Source: Nalesnik, C. A.; Hansen, B. N.; Hsu, J. T. Fluid Phase Equil. (1998), 146(1,2), 315-323.

Taxol (C47H51NO14; MW=853.91) y x 10

312.2 141.2 1.10 311.4 209.8 2.06 310.2 278.5 3.72 310.6 346.9 4.59 322.5 140.9 3.57 322.4 209.5 4.33 322.0 277.9 4.38 322.0 346.2 5.25 328.8 141.0 5.71 328.9 209.5 6.32 328.9 278.0 5.91 329.0 346.7 5.67 Synonym: Paclitaxel Source: Vandana, V.; Teja, A. S. Fluid Phase Equil. (1997), 135(1), 83-87.

8 6 6

P (bar)

[T-2]

6

y x 10

T (K)

500

4 311 K 322 K 329 K

2 0 100

200

300

400

P (bar)

735

CAT4240—CHAPTER 20—1/11/2006—19:15—SRAM—XML MODEL C – pp. 735–808

736

Solubility in Supercritical Carbon Dioxide

Tebuconazole (C16H22ClN3O; MW=307.82)

338.15

323.15

338.15

100 110 125 150 200 300 100 110 125 150 200 300 150 150 150 100 110 125 150 200 300 100 110 125 150 200 300

1.9 9.6 17.9 44.8 88.6 169.1 8.6 16.8 45.5 193.3 910.7 2468.9 88.0 193.3 429.1 0.7 3.2 15.8 57.2 115.3 292.8 3.5 7.3 24.4 147.1 938.4 3707.1

6

323 K 338 K

y x 10

6.3 13.4 47.8 165.0 334.3 642.1 3.5 5.7 18.0 80.8 483.8 1857.1

1000

0 50

150

250

350

250

350

P (bar) 4000 Acetone, 323 K Acetone, 338 K Methanol, 323 K Methanol, 338 K

3000 6

323.15

0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 Acetone 3.0 3.0 3.0 3.0 3.0 3.0 3.0 3.0 3.0 3.0 3.0 3.0 1.0 3.5 5.0 Methanol 3.0 3.0 3.0 3.0 3.0 3.0 3.0 3.0 3.0 3.0 3.0 3.0

2000

y x 106

y x 10

338.15

100 110 125 150 200 300 100 110 125 150 200 300

Cosolvent (mol%)

2000

1000

0 50

150 P (bar)

500 338 K 150 bar 6

323.15

P (bar)

[T-3]

y x 10

T (K)

1)

250 Acetone Methanol

0 0

5 Cosolvent (mol%)

CAT4240—CHAPTER 20—1/11/2006—19:15—SRAM—XML MODEL C – pp. 735–808

10

Solubility Data T

150 150 150

737

1.0 5.0 10.0

105.6 146.6 336.0

1: Cosolvent in CO2. Synonym: 1-(4-Chlorophenyl)-4,4-dimethyl-3-(1,2,4triazol-1-ylmethyl)pentan-3-ol Source: Sahle-Demessie, E.; Pillai, U. R.; Junsophonsri, S.; Levien, K. L. J. Chem. Eng. Data (2003), 48(3), 541-547.

Terbium tris(2,2,6,6-tetramethyl-3,5-heptanedionate) (C33H57O6Tb; FW=708.74) [T-4]

323

333

124.6 151.4 185.8 233.9 303.8 124.6 146.0 165.3 187.6 206.4 237.1 267.4 300.4 352.3 172.1 207.3 234.0 280.8 349.7

S (g/L) 0.88 1.17 1.46 1.70 2.15 1.02 1.63 2.01 2.34 2.58 2.99 3.18 3.34 3.48 3.07 3.52 4.02 4.50 4.73

y x 106 70 90 110 120 150 100 150 170 190 200 230 230 240 240 280 300 320 340 340

400 313 K 323 K 333 K

300 6

313

P (bar)

y x 10

T (K)

200

100

0 50

Synonyms: Tb(thd)3; Tris(2,2,6,6-tetramethyl 3, 5-heptanedionato)terbium Source: Andersen, W. C.; Sievers, R. E.; Lagalante, A. F.; Bruno, T. J. J. Chem. Eng. Data (2001), 46(5), 1045-1049.

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150

250 P (bar)

350

738

Solubility in Supercritical Carbon Dioxide

Terbium tris(2,2,7-trimethyl-3,5-octanedionate) (C33H57O6Tb; FW=708.74) T (K)

S (g/L)

y x 10

124.3 145.4 149.8 164.9 166.2 187.7 205.2 215.4 248.3 251.2

7.60 640 10.90 870 12.20 970 13.67 1060 14.85 1150 16.52 1240 19.53 1430 19.35 1400 4000 21.74 1530 23.07 1620 305.6 24.14 1640 3000 318.4 25.48 1720 323 128.3 5.41 530 146.5 13.34 1190 146.8 14.06 1260 2000 149.2 12.15 1080 165.7 21.80 1840 168.2 19.18 1610 187.4 31.27 2520 1000 189.6 25.77 2070 208.0 36.83 2870 209.5 30.99 2410 0 225.7 41.68 3170 238.8 45.39 3400 100 265.8 50.91 3720 333 140.6 5.01 550 148.0 7.51 780 153.1 8.74 880 167.6 14.61 1370 173.4 16.30 1500 189.4 24.20 2120 195.8 26.26 2260 208.4 33.84 2840 212.9 33.50 2790 236.7 43.11 3450 Synonyms: Tb(tod)3, Tris(2,2,7-trimethyl-3,5octanedionato)terbium Source: Andersen, W. C.; Sievers, R. E.; Lagalante, A. F.; Bruno, T. J. J. Chem. Eng. Data (2001), 46(5), 1045-1049.

313 K 323 K 333 K

y x 10

6

313

P (bar)

[T-5]

6

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200 P (bar)

300

Solubility Data T

739

m -Terphenyl (C18H14; MW=230.30) 308.2

91 111 139 191 238 284

y x 10

[T-6]

6

7 22 76 200 540 780

800 6

T (K) P (bar)

2)

y x 10

1)

400

0

1: Calculated from temperature and density in the source graph. 2: Obtained by digitizing the graph in the original article. May have large reading error as the original graph is small. Synonym: 1,3-Diphenylbenzene Source: Burk, R.; Kruus, P. Can. J. Chem. Eng. (1992), 70(2), 1403-1407.

50

150

250

P (bar)

Testosterone (C19H28O2; MW=288.42)

328.15

373.15

82.4 99.0 113.8 129.4 146.1 160.8 177.5 196.1 210.8 226.5 82.4 99.0 113.8 129.4 146.1 160.8 177.5 196.1 210.8 226.5 82.4 99.0 113.8 129.4 146.1 160.8

y x 10

6.57 8.22 13.10 24.60 29.60 31.20 32.90 37.80 41.10 52.60 0.95 2.86 8.25 10.40 19.70 23.00 27.90 47.70 69.00 73.90 0.46 0.82 1.56 1.97 16.40 24.60

100 308.15 K 328.15 K 373.15 K

80

6

308.15

P (bar)

y x 10

T (K)

[T-7]

6

60

40

20

0 50

100

CAT4240—CHAPTER 20—1/11/2006—19:15—SRAM—XML MODEL C – pp. 735–808

150 P (bar)

200

250

740

Solubility in Supercritical Carbon Dioxide

177.5 196.1 210.8 226.5

39.40 63.90 85.30 90.50

Synonym: 17b-Hydroxyandrost-4-en-3-one Source: Dean, J. R.; Kane, M.; Khundker, S.; Dowle, C.; Tranter, R. L.; Jones, P. Analyst (1995), 120(8), 2153-2157.

Testosterone (C19H28O2; MW=288.42)

313.2

318.2

328.2

88.4 106.0 121.6 139.1 155.7 171.8 190.1 207.8 224.8 242.3 104.8 125.3 138.5 156.1 156.2 180.0 210.5 231.8 241.7 87.2 104.3 121.5 138.6 155.9 172.6 189.8 207.5 224.5 242.9 87.0 104.2 121.5 139.7

H2 O (vol %) 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0

y x 106 2.28 7.31 11.90 20.09 25.84 31.60 34.26 39.83 45.03 50.28 3.27 5.27 18.53 21.12 22.35 30.92 40.22 48.86 55.75 0.69 1.22 3.71 15.76 18.70 34.04 39.97 41.74 57.12 62.47 0.39 0.95 3.08 8.44

80 CO2 308.2 K CO2 313.2 K CO2 318.2 K CO2 328.2 K w/H2O 308.2 K w/H2O 328.2 K

60

6

308.2

P (bar)

[T-8]

y x 10

T (K)

1)

40

20

0 50

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100

150 P (bar)

200

250

Solubility Data T

308.2

328.2

156.2 173.2 190.8 207.5 224.8 241.8 91.3 105.5 122.1 142.3 158.3 176.1 191.8 209.6 223.9 241.9 121.8 142.2 158.3 173.5 173.2 192.4 206.3 226.9 245.6

741

0.0 0.0 0.0 0.0 0.0 0.0 10.0 10.0 10.0 10.0 10.0 10.0 10.0 10.0 10.0 10.0 10.0 10.0 10.0 10.0 10.0 10.0 10.0 10.0 10.0

13.72 24.67 42.33 48.26 61.88 70.10 8.66 12.58 17.16 22.99 26.57 37.32 40.83 46.23 48.91 52.23 5.05 10.95 15.31 35.91 36.26 47.71 48.93 64.88 71.20

1. Cosolvent in CO2. Synonym: 17b-Hydroxyandrost-4-en-3-one Source: Kosal, E.; Lee, C. H.; Holder, G. D. J. Supercrit. Fluids (1992), 5(3), 169-179.

Testosterone-17-propionate (C22H32O3; MW=344.49)

373.15

82.4 99.0 113.8 129.4 146.1 160.8 177.5 196.1 210.8 226.5 82.4 99.0 113.8 129.4 146.1

y x 10

1.31 7.01 13.10 16.50 26.20 41.30 63.50 75.80 82.50 91.00 0.56 0.98 1.31 5.64 12.20

120 328.15 K 373.15 K

90 6

P (bar)

y x 10

T (K) 328.15

[T-9]

6

60

30

0 50

100

150 P (bar)

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200

250

742

Solubility in Supercritical Carbon Dioxide

160.8 177.5 196.1 210.8 226.5

16.50 53.60 73.90 85.30 99.50

Synonym: 17b -(1-Oxopropoxy)-androst-4-en-3-one Source: Dean, J. R.; Kane, M.; Khundker, S.; Dowle, C.; Tranter, R. L.; Jones, P. Analyst (1995), 120(8), 2153-2157.

Tetrabromobisphenol-A (C15H12Br4O2; 543.87) T (K)

P (bar)

w x 106

[T-10]

y1) x 106

298.15

298.15 K 313.15 K 333.15 K 353.15 k 373.15 K

y x 10

6

200 190 15.4 400 300 210 17.0 400 260 21.0 500 310 25.1 300 313.15 200 450 36.4 300 610 49.4 400 760 61.5 500 920 74.5 200 333.15 200 280 22.7 300 580 47.0 400 900 72.9 100 500 1220 98.8 353.15 200 220 17.8 300 850 68.8 400 1590 128.9 0 500 2310 187.3 150 373.15 200 320 25.9 300 1330 107.8 400 2490 202.0 500 4320 351.0 1: Calculated from w. Synonyms: 4,4'-Isopropylidenebis[2,6-dibromophenol]; 2,2',6,6'-Tetrabromobisphenol A Source: Gamse, T.; Steinkellner, F. ; Marr, R.; Alessi, P.; Kikic, I. Ind. Eng. Chem. Res. (2000), 39(12), 4888-4890.

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250

350 P (bar)

450

550

Solubility Data T

743

2,3',4',5-Tetrachlorobiphenyl (C12H6Cl4; MW=291.99) T (K)

P (bar)

[T-11]

6

y x 10

308.1

308.1 K 313.1 K 323.1 K

y x 10

6

102.9 169 139.7 284 166.9 300 1500 242.7 400 262.4 452 365.2 495 313.1 94.3 183 107.3 286 1000 117.4 339 135.5 443 157.5 505 162.9 548 218.1 609 500 251.6 664 277.5 670 322.4 748 389.8 860 323.1 120.0 213 0 126.7 199 0 157.0 484 189.6 572 231.5 818 301.5 989 369.7 1120 454.1 1360 Synonym: PCB 70 Source: Yu, E.; Richter, M.; Chen, P.; Wang, X.; Tavlarides, L. L. Ind. Eng. Chem. Res. (1995), 34(1), 340-346.

100

3,3',4,4'-Tetrachlorobiphenyl (C12H6Cl4; MW=291.99) T (K) P (bar) 313 100 110 120 130 140 150 160 170 180 190

y x 106 3.2 5.1 7.2 8.9 10.8 12.5 14.3 16.0 17.0 18.8

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200

300

400

500

P (bar)

[T-12]

744

90 313 K 323 K 333 K

6

60 y x 10

200 20.3 220 22.5 240 24.5 260 26.7 280 29.1 300 32.2 323 100 0.6 110 1.9 120 4.1 130 7.0 140 10.0 150 12.9 160 15.7 170 18.7 180 22.6 190 24.5 200 27.1 220 32.5 240 37.8 260 43.8 280 48.3 300 53.2 333 100 0.5 110 0.9 120 2.0 130 4.0 140 6.8 150 10.6 160 15.0 170 20.0 180 24.0 190 29.0 200 34.5 220 44.4 240 53.3 260 63.4 280 72.2 300 82.6 Synonym: PCB 77 Source: Anitescu, G.; Tavlarides, L. L. J. Supercrit. Fluids (1999), 14(3), 197-211.

Solubility in Supercritical Carbon Dioxide

30

0 50

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150

250 P (bar)

350

Solubility Data T

745

3,3',4,4'-Tetrachlorobiphenyl (C12H6Cl4; MW=291.99)

313

100 110 120 130 140 150 160 170 180 190 200 220 240 260 280 300 100 110 120 130 140 150 160 170 180 190 200 220 240 260 280 300 100 110 120 130 140 150 160 170 180 190 200

323

333

n -Butane (mol%) 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0

[T-13]

y x 106 4.7 7.3 10.0 12.4 14.8 17.1 19.3 21.4 22.6 24.7 26.1 29.3 32.7 35.5 38.2 40.9 0.9 2.8 5.9 9.9 13.9 17.6 21.0 24.7 28.3 31.8 34.9 41.2 47.2 53.2 59.0 64.4 0.8 1.4 3.0 5.8 9.8 15.0 20.5 26.9 32.1 38.1 44.6

100 313 K 323 K 333 K

80

6

P (bar)

y x 10

T (K)

1)

60

40

20

0 50

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150

250 P (bar)

350

746

Solubility in Supercritical Carbon Dioxide

220 5.0 55.9 240 5.0 65.8 260 5.0 77.5 280 5.0 86.7 300 5.0 97.1 1: Cosolvent in CO 2. Synonym: PCB 77 Source: Anitescu, G.; Tavlarides, L. L. J. Supercrit. Fluids (1999), 14(3), 197-211.

3,3',4,4'-Tetrachlorobiphenyl (C12H6Cl4; MW=291.99)

313

100 110 120 130 140 150 160 170 180 190 200 220 240 260 280 300 100 110 120 130 140 150 160 170 180 190 200 220 240 260 280 300 100 110 120 130

323

333

Methanol1) (mol%) 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0

y x 106 4.1 6.4 8.9 10.9 13.1 15.0 17.0 18.8 19.8 21.8 23.4 25.7 27.8 30.1 32.5 35.7 0.8 2.6 5.5 9.2 12.9 16.4 19.6 23.0 26.4 29.4 32.3 38.5 44.5 50.6 56.0 61.2 0.7 1.2 2.8 5.5

100 313 K 323 K 333 K

80

6

P (bar)

y x 10

T (K)

[T-14]

60

40

20

0 50

CAT4240—CHAPTER 20—1/11/2006—19:15—SRAM—XML MODEL C – pp. 735–808

150

250 P (bar)

350

Solubility Data T

747

140 5.0 9.2 150 5.0 14.0 160 5.0 19.4 170 5.0 25.4 180 5.0 30.0 190 5.0 35.6 200 5.0 41.7 220 5.0 53.0 240 5.0 62.6 260 5.0 73.7 280 5.0 83.1 300 5.0 94.2 1: Cosolvent in CO2. Synonym: PCB 77 Source: Anitescu, G.; Tavlarides, L. L. J. Supercrit. Fluids (1999), 14(3), 197-211.

Tetrachloroisophthalonitrile (C8Cl4N2; MW=265.91) T (K)

P (bar)

[T-15]

6

y x 10

318

318 K 328 K 338 K

y x 10

6

100 13.2 150 48.1 300 170 84.9 200 132.0 225 121.0 250 132.0 300 156.0 200 328 100 5.3 125 46.2 150 60.9 170 79.9 200 99.3 100 225 122.0 250 141.0 300 180.0 338 100 6.4 125 10.6 0 150 21.7 50 170 54.3 200 137.0 225 154.0 250 192.0 300 268.0 Synonyms: Chlorothalonil; 2,4,5,6-Tetrachloro-1,3benzenedicarbonitrile Source: Sahle-Demessie, E.; Pillai, U. R.; Junsophonsri, S.; Levien, K. L. J. Chem. Eng. Data (2003), 48(3), 541-547.

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150

250 P (bar)

350

748

Solubility in Supercritical Carbon Dioxide

2,3,4,5-Tetrachlorophenol (C6H2Cl4O; MW=231.89)

294 303 314 323 333 345

30000

6

295.2

y x 10

Cosolvent y4) x 106 (mol %) 74 0.00 130 87 0.00 360 154 0.00 2000 213 0.00 5500 322 0.00 4200 n-Hexane 60 3.20 553 65 3.20 848 121 3.20 4114 181 3.20 7438 292 3.20 9060 Methanol 65 1.59 1000 74 1.59 1400 154 1.59 5300 275 1.59 19600 452 1.59 9300 67 3.21 1300 82 3.21 3200 138 3.21 11000 247 3.21 18800 426 3.21 29500 r = constant (0.80 g/ml) 72 0.00 62 113 0.00 162 170 0.00 770 211 0.00 1903 266 0.00 4704 322 0.00 5752

T1) (K) P2) (bar)

[T-16]

3)

Pure CO2 Hexan 3.20% MeOH 1.59% MeOH 3.21% d = 0.80 g/mol

20000

10000

0 0

1: The temperature at 0.80 g/ml was obtained by digitizing the graph in the original article. 2: Calculated from temperature and density in the source graph. 3: Cosolvent in CO2. 4: Obtained by digitizing the graph in the original article. Source: Burk, R.; Kruus, P. Can. J. Chem. Eng. (1992), 70(2), 1403-1407.

CAT4240—CHAPTER 20—1/11/2006—19:15—SRAM—XML MODEL C – pp. 735–808

100

200

300

P (bar)

400

Solubility Data T

749

Tetracosane (C24H50; MW=338.65) T (K)

P (bar)

S (g/L)

1)

[T-17]

y x 10

6

6

y x 10

184.7 8.82 1820 205.2 14.88 2866 223.9 21.50 3952 244.8 28.64 5051 263.8 36.06 6166 1: Calculated from S. Source: Chartier, T.; Delhomme, E.; Baumard, J. F.; Marteau, P.; Subra, P.; Tufeu, R. Ind. Eng. Chem. Res. (1999), 38(5), 1904-1910.

8000

343

4000

0 150

200

250 P (bar)

Tetracosane (C24H50; MW=338.65) T (K)

P (bar)

6

w x 10

1)

y x 10

300

[T-18] 6

329.7

6

6000 y x 10

190.4 22000 2900 246.2 35000 4700 281.4 46000 6200 339.2 203.6 22000 2900 234.5 35000 4700 283.7 46000 6200 348.1 213.8 22000 2900 249.7 35000 4700 279.8 46000 6200 357.1 226.6 22000 2900 279.8 46000 6200 1: Calculated from w. Source: Nieuwoudt, I.; du Rand, M. J. Supercrit. Fluids (2002), 22(3), 185-199.

329.7 K 339.2 K 348.1 K 357.1 K

4000

2000 150

200

250

300

P (bar)

Tetracosane (C24H50; MW=338.65)

[T-19]

6

12000

6

310 K 320 K

y x 10

y x 10 T (K) P (bar) 310 110.0 620 141.3 789 141.5 792 201.0 1130 204.0 606 206.0 1030 260.0 820 320 110.0 353 141.3 1370 141.5 1380 206.0 6980 260.0 10400 Source: Schmitt, W. J.; Reid, R. C. Chem. Eng. Comm. (1988), 64, 155-176.

8000

4000

0 100

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200 P (bar)

300

750

Solubility in Supercritical Carbon Dioxide

Tetracosane (C24H50; MW=338.65)

313.2

318.2

50.3 67.2 93.1 114.5 138.6 161.3 182.7 204.8 50.3 67.9 93.1 113.4 139.3 160.7 182.0 207.2 50.3 67.7 90.7 113.8 140.0 161.0 182.0 208.9

y x 10

486 503 629 813 917 1195 1520 2050 418 363 735 1330 1874 2290 3170 4303 482 394 483 1160 2380 3210 4770 7670

8000 308.2 K 313.2 K 318.2 K

6000 6

308.2

P (bar)

y x 10

T (K)

[T-20]

6

4000

2000

0 0

100

200

P (bar)

Source: Yau, J. S.; Tsai, F. N. J. Chem. Eng. Data (1993), 38(2), 171-174.

Tetracosane (C24H50; MW=338.65)

Source: Chandler, K.; Pouillot, F. L. L.; Eckert, C. A. J. Chem. Eng. Data (1996), 41, 6-10.

600 6

y x 10 170 240 260 330 360 350 430

y x 10

T (K) P (bar) 308.2 100 120 140 160 180 200 240

[T-21]

6

300

0 50

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150 P (bar)

250

Solubility Data T

751

Tetracosane (C24H50; MW=338.65) 123 142 143 156 162 170 259 270 448 459

y x 10

880 1000 910 870 1010 1060 960 1060 940 1040

1200

6

310

P (bar)

y x 10

T (K)

[T-22]

6

900

600 0

200

400

600

P (bar)

Source: Furuya, T.; Teja, A. S. J. Supercrit. Fluids (2004), 29(3), 231-236.

5,10,15,20-Tetrakis(3,5-bis(trifluoromethyl)phenyl)porphyrin (C52H22F24N4; MW=1158.73) y x 106

800 313.15 K 343.15 K 373.15 K

600 6

10.3 97.8 225.0 357.0 559.0 0.1 8.3 106.0 325.0 712.0 0.1 0.7 22.5 174.0 686.0

y x 10

T (K) P (bar) 313.15 103 159 214 269 324 343.15 103 159 214 269 324 373.15 103 159 214 269 324

[T-23]

400 200 0 50

Source: Sane, A.; Taylor, S.; Sun, Y.-P.; Thies, M. C. J. Supercrit. Fluids (2004), 28(2-3), 277-285.

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150

250 P (bar)

350

752

Solubility in Supercritical Carbon Dioxide

5,10,15,20-Tetrakis(pentafluorophenyl)porphyrin (C44H10F20N4; MW=974.55) M x 10 y1) x 106 (mol/L) 313.15 103 2.44 0.164 108 4.14 0.268 3 126 10.50 0.627 152 18.00 1.007 170 31.00 1.683 3.261 195 62.00 2 323.15 127 1.75 0.122 134 3.66 0.245 156 10.10 0.620 184 16.80 0.965 1 206 28.20 1.563 233 52.50 2.814 333.15 149 1.49 0.108 0 159 3.43 0.236 50 182 9.28 0.588 220 16.20 0.944 236 26.40 1.501 252 40.40 2.250 1: Calculated from M. Synonym: 5,10,15,20-Tetrakis(pentafluorophenyl)porphine Source: Sato, H.; Inada, Y.; Nagamura, T.; Funahashi, S. J. Supercrit. Fluids (2001), 21(1), 71-80. P (bar)

313 K 323 K 333 K

y x 10

6

T (K)

[T-24]

6

150 P (bar)

Tetralin (C10H12; MW=132.20)

[T-25]

6

6

10000 y x 10

y x 10 T (K) P (bar) 323 52 300 80 700 85 1000 90 1400 95 2500 110 8400 Synonym: 1,2,3,4-Tetrahydronaphthalene Source: Mukhopadhyay, M.; De, S. K. J. Chem. Eng. Data (1995), 40(4), 909-913.

250

5000

0 40

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80 P (bar)

120

Solubility Data T

753

Tetralin (C10H12; MW=132.20)

353.2

393.1

P (bar) 60.9 60.9 65.9 65.9 70.9 70.9 75.9 75.9 80.9 80.9 60.9 60.9 80.8 80.8 100.8 100.8 120.9 120.9 140.9 140.9 140.9 160.8 160.9 60.9 60.9 80.9 80.9 100.9 100.9 120.9 140.9 140.9 160.9 160.9 180.8 180.8 180.8 200.8 200.8 200.8

y x 10 500 400 400 400 700 900 1100 1000 2400 2300 1000 1100 1200 1100 2100 2300 5200 5100 11100 11400 9100 23300 22900 4000 4100 4500 4500 5600 5700 6200 9300 9200 12800 12700 17700 18300 18300 26700 27400 27500

30000 313.2 K 353.2 K 393.1 K

20000 6

313.2

y x 10

T (K)

[T-26]

6

10000

0 50

Synonym: 1,2,3,4-Tetrahydronaphthalene Source: Walther, D.; Maurer, G. J. Chem. Eng. Data (1993), 38, 247-249.

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140 P (bar)

230

754

Solubility in Supercritical Carbon Dioxide

a -Tetralol (C10H12O; MW=148.20) 303.15

313.15

323.15

P (bar) 125 133 135 138 145 150 152 154 160 165 166 167 169 177 187 197 205 138 152 155 163 175 180 181 183 184 191 192 194 200 203 213 223 230 163 171 172 176 187 196 199 200 203 208

y x 10

7000 8300 8600 9800 11900 13500 13900 14100 14400 16700 17100 17700 19400 21100 25400 30500 36600 7000 8300 8600 9800 11900 13500 13900 14100 14400 16700 17100 17700 19400 21100 25400 30500 36600 7000 8300 8600 9800 11900 13500 13900 14100 14400 16700

40000

30000

y x 106

T (K)

[T-27]

6

303.15 K 313.15 K 323.15 K 333.15 K

20000

10000

0 100

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150

200 P (bar)

250

Solubility Data T

755

209 17100 210 17700 213 19400 219 21100 228 25400 237 30500 245 36600 333.15 173 7000 183 8300 185 8600 190 9800 199 11900 209 13500 210 13900 211 14100 212 14400 220 16700 221 17100 223 17700 226 19400 233 21100 243 25400 251 30500 258 36600 Synonym: 1,2,3,4-Tetrahydro-1-naphthol Source: Borg, P.; Jaubert, J.-N.; Denet, F. Fluid Phase Equil. (2001), 191(1-2), 59-69.

a-Tetralol (C10H12O; MW=148.20) Ethanol1) y x 106 (wt%) 10.3 303.15 94 23400 4.5 119 17600 1.4 144 16700 10.3 313.15 118 23400 4.5 146 17600 1.4 171 16700 10.3 323.15 135 23400 4.5 170 17600 1.4 194 16700 10.3 333.15 148 23400 4.5 185 17600 1.4 216 16700 1: Cosolvent in CO2. Synonym: 1,2,3,4-Tetrahydro-1-naphthol Source: Borg, P. ; Jaubert, J.-N.; Denet, F. Fluid Phase Equil. (2001), 191(1-2), 59-69. P (bar)

25000

y x 106

T (K)

[T-28] EtOH (wt%) 10.3

303.15 K 313.15 K 323.15 K 333.15 K

20000 4.5 1.4

15000 50

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150 P (bar)

250

756

Solubility in Supercritical Carbon Dioxide

Tetraethylene glycol lauryl ether1) (C20H42O5; MW=362.54)

313.15

323.15

102.0 130.2 151.5 168.7 183.5 196.5 121.2 149.8 173.6 188.3 108.4 133.6 156.9 169.5 100.7 121.2 138.6 149.4 94.0 111.2 125.5 133.5 89.8 104.2 114.8 124.2 112.5 132.7 158.6 181.8 193.7

0.00 0.00 0.00 0.00 0.00 0.00 0.28 0.28 0.28 0.28 0.56 0.56 0.56 0.56 0.84 0.84 0.84 0.84 1.12 1.12 1.12 1.12 1.40 1.40 1.40 1.40 0.00 0.00 0.00 0.00 0.00

[T-29]

y3) x 106 787 1386 1958 2496 3040 3638 1336 2509 3689 4526 1336 2522 3702 4578 1311 2534 3766 4642 1336 2547 3740 4681 1398 2597 3779 4694 478 891 1430 2195 2606

6000

313 K - 0.00 313 K - 0.28 313 K - 0.56 313 K - 0.84 313 K - 1.12 313 K - 1.40 323 K - 0.00

4000 y x 106

T (K)

nP (bar) Pentanol2) (mol/L)

2000

0 50

1: In the source the name of the compound includes "laurel" instead of "lauryl". 2: Cosolvent in CO2. 3: Caculated from w. Synonym: Tetraethylene glycol monododecyl ether Source: Liu, J.; Han, B. ; Li, G.; Liu, Z. ; He, J.; Yang, G. Fluid Phase Equil. (2001), 187-188, 247-254.

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100

150 P (bar)

200

Solubility Data T

757

Theobromine (C7H8N4O2; MW=180.16) 313

333

353

P (bar)

yx

213 233 253 273 293 313 345 193 213 233 253 273 293 313 344 194 214 234 254 274 293 314 344

0.88 1.10 1.32 1.39 1.51 1.59 1.81 1.78 1.93 1.93 2.13 2.47 2.47 2.67 3.03 2.52 2.76 3.05 3.30 3.47 3.98 4.18 4.71

6 313 K 333 K 353 K

4 y x 106

T (K)

[T-30]

106

2

0 150

250

350

P (bar)

Synonyms: 3,7-Dimethylxanthine; 3,7Dihydro-3,7-dimethyl-1H-purine-2,6dione Source: Johannsen, M.; Brunner, G. Fluid Phase Equil. (1994), 95, 215-226.

Theobromine (C7H8N4O2; MW=180.16) 333.15

353.15

368.15

P (bar) 150 200 240 300 150 200 240 268 300 100 200 240

yx

0.63 0.69 0.79 1.13 0.67 1.07 1.20 1.34 1.77 0.27 1.29 1.91

3

y x 106

T (K)

[T-31]

106 333.15 K 353.15 K 368.15 K

2

1

0 50

150

250 P (bar)

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350

758

Solubility in Supercritical Carbon Dioxide

270 300

2.16 2.98

Synonyms: 3,7-Dimethyixanthine; 3,7Dihydro-3,7-dimethyl-1H-purine-2,6dione Source: Li, S.; Varadarajan, G. S.; Hartland, S. Fluid Phase Equil. (1991), 68, 263-280.

Theobromine (C7H8N4O2; MW=180.16) T (K)

P1)

(bar)

W1)

(g/kg)

y2)

x

[T-32]

106

313.2

313.2 K 323.2 K 338.2 K 343.2 K 353.2 K

y x 106

140 0.00174 0.426 160 0.00210 0.513 181 0.00250 0.610 200 0.00285 0.697 220 0.00329 0.804 240 0.00365 0.891 2 323.2 140 0.00194 0.475 160 0.00230 0.562 180 0.00274 0.668 200 0.00321 0.784 220 0.00377 0.920 240 0.00432 1.056 338.2 139 0.00206 0.504 1 160 0.00258 0.630 180 0.00309 0.755 200 0.00393 0.959 220 0.00472 1.150 240 0.00571 1.390 343.2 140 0.00242 0.591 0 160 0.00309 0.755 180 0.00345 0.843 100 200 0.00511 1.250 220 0.00587 1.433 240 0.00714 1.743 353.2 140 0.00266 0.649 180 0.00452 1.100 219 0.00698 1.710 240 0.00821 2.010 1: Obtained by digitizing the graph in the original article. 2: Calculated from W. Synonyms: 3,7-Dimethylxanthine; 3,7-Dihydro3, 7-dimethyl-1H-purine-2,6-dione Source: Saldana, M. D. A.; Mohamed, R. S.; Baer, M. G.; Mazzafera, P. J. Agric. Food. Chem. (1999), 47, 3804-3808.

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150

200 P (bar)

250

Solubility Data T

759

Theobromine (C7H8N4O2; MW=180.16) P (bar)

313

333

W Methanol1) (g/kg solv) (wt%)

213 219 216 217 218 216 218 220 217 216 213 219 218 220 217 216

0.0 9.0 10.1 10.8 11.5 13.0 15.1 16.6 19.4 19.7 0.0 9.0 11.5 16.6 19.4 19.7

y2) x 106

0.004 0.050 0.050 0.080 0.060 0.040 0.110 0.100 0.130 0.120 0.008 0.080 0.100 0.170 0.240 0.200

1.0 11.8 11.8 18.8 14.1 9.3 25.4 23.0 29.6 27.3 2.0 18.9 23.4 39.1 54.7 45.5

60 313 K 333 K

40 y x 106

T (K)

[T-33]

20

0 0

5

10

15

20

Methanol (wt%)

1: Cosolvent in CO2 on a solute-free basis. 2: Calculated from W. Synonyms: 3,7-Dimethylxanthine; 3,7-Dihydro3, 7-dimethyl-1H-purine-2,6-dione Source: Johannsen, M.; Brunner, G. J. Chem. Eng. Data (1995), 40(2), 431-434.

Theobromine (C7H8N4O2; MW=180.16)

333.15

150

200

250

300

368.15

200 250

Ethanol2) (wt %) 0.00 5.96 9.09 31.80 6.11 14.42 32.76 0.00 14.89 21.94 25.24 0.00 13.79 16.93 7.29 0.00 2.00 5.00

w3) x 106 3 16 34 21 24 40 200 4 50 120 170 5 53 80 48 8 21 41

y4) x 106 0.7 3.8 8.0 4.6 5.7 9.3 43.5 1.0 11.6 27.1 37.9 1.2 12.3 18.4 11.4 2.0 5.1 9.8

333 K, 150 bar 333 K, 200 bar 333 K, 250 bar 333 K, 300 bar 368 K, 200 bar 368 K, 250 bar 368 K, 300 bar

90

y x 106

T (K) P1) (bar)

[T-34]

60

30

0 0

10

20

Ethanol (wt %)

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30

760

Solubility in Supercritical Carbon Dioxide

300

0.00 12 2.9 3.00 37 8.9 8.71 71 16.8 17.50 240 55.0 32.43 390 85.0 1: Calculated from density and temperature data. 2: Cosolvent in CO2 on a solute-free basis. 3: Obtained by digitizing the graph in the original article. 4: Calculated from w. Synonyms: 3,7-Dimethylxanthine; 3,7-Dihydro-3, 7-dimethyl-1H-purine-2,6-dione Source: Li, S.; Hartland, S. J. Supercrit. Fluids (1992), 5(1), 7-12.

Theophylline (C7H8N4O2; MW=180.16) 313

333

353

P (bar) 199 219 239 259 279 299 319 349 199 219 239 259 279 299 319 349 199 219 239 259 279 299 319 349

yx

10.7 10.3 10.7 11.0 11.5 10.7 12.5 13.4 16.1 16.6 17.1 17.3 16.6 17.8 18.8 19.8 18.1 19.3 18.8 22.2 25.2 29.1 29.6 33.2

35 313 K 333 K 353 K

25 y x 106

T (K)

[T-35]

106

15

5 150

Synonym: 1,3-Dimethylxanthine Source: Johannsen, M.; Brunner, G. Fluid Phase Equil. (1994), 95, 215-226.

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250 P (bar)

350

Solubility Data T

761

Theophylline (C7H8N4O2; MW=180.16) T (K)

P1)

(bar)

W1)

(mg/kg)

y2)

x

[T-36]

106

313.2

313.2 K 323.2 K 338.2 K 343.2 K

y x 106

140 5.58 1.36 160 6.31 1.54 180 7.48 1.83 4 200 8.68 2.12 220 9.63 2.35 240 10.53 2.57 323.2 140 6.07 1.48 160 6.99 1.71 3 180 8.22 2.01 200 9.22 2.25 220 10.10 2.47 240 11.29 2.76 338.2 140 6.80 1.66 2 160 7.89 1.93 180 9.12 2.23 200 10.40 2.54 220 11.67 2.85 240 12.82 3.13 1 343.2 140 7.54 1.84 100 160 8.65 2.11 180 10.45 2.55 200 11.37 2.78 220 12.68 3.10 240 14.18 3.46 1: Obtained by digitizing the graph in the original article. 2: Calculated from W. Synonym: 1,3-Dimethylxanthine Source: Saldana, M. D. A.; Mohamed, R. S.; Baer, M.G.; Mazzafera, P. J. Agric. Food. Chem. (1999), 47, 3804-3808.

150

200 P (bar)

Theophylline (C7H8N4O2; MW=180.16) 1)

T (K) P (bar) y x 10 Anhydrate

313.15 101.1 151.2 200.5 249.7 300.8

0.56 1.17 2.00 2.13 3.75

Hydrate (C7H8N4O2.H2O)

[T-37]

6

Anhydrate

4 y x 106

1)

250

313.15 102.0 0.94 151.2 1.88 201.4 2.67 250.6 3.27 299.8 3.99 1: Obtained by digitizing the graph in the original article. Synonym: 1,3-Dimethylxanthine Source: Bettini, R.; Bertolini, G.; Frigo, E.; Rossi, A.; Casini, I.; Pasquali, I.; Giordano, F. J. Therm. Anal. Cal. (2004), 77(2), 625-638.

Hydrate

2

0 50

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150

250 P (bar)

350

762

Solubility in Supercritical Carbon Dioxide

Theophylline (C7H8N4O2; MW=180.16) T (K)

P (bar)

1)

Methanol (wt%)

W (g/kg solv)

[T-38] y2) x 106

6

313

y x 10

219 0.0 0.04 10 218 4.2 0.62 149 218 5.5 0.77 184 218 6.9 0.79 188 218 9.2 1.80 425 218 10.7 1.90 446 218 10.9 1.90 446 218 12.8 2.50 582 218 14.5 2.80 648 1: Cosolvent in CO2 on a solute-free basis. 2: Calculated from W. Synonym: 1,3-Dimethylxanthine Source: Johannsen, M.; Brunner, G. J. Chem. Eng. Data (1995), 40(2), 431-434.

800

400

0 0

5

10

Methanol (wt%)

Thiamphenicol (C12H15Cl2NO5S; MW=356.22) T (K)

P (bar)

15

[T-39]

6

y x 10

0.45 185 1.00 289 1.16 358 1.40 396 1.52 431 1.54 467 0.96 333.15 291 1.69 342 2.59 401 3.38 447 3.56 474 Synonym: 2,2-Dichloro-N-[2-hydroxy-1(hydroxymethyl)-2-[4-(methylsulfonyl) phenyl]ethyl]acetamide Source: Li, S.; Maxwell, R. J.; Shadwell, R. J. Fluid Phase Equil. (2002), 198(1), 67-80.

4

313.15 K 333.15 K

y x 10

6

313.15

2

0 100

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200

300 P (bar)

400

500

Solubility Data T

763

2-(Thiocyanomethylthio)benzothiazole (C9H6N2S3; MW=238.36) y x 106

1500

y x 106

0.0 8 0.0 38 0.0 107 0.0 256 0.0 590 0.0 1115 338 0.0 2 0.0 6 0.0 23 0.0 111 0.0 621 0.0 1396 Acetone 323 100 1.68 5 150 1.68 254 200 1.68 877 300 1.68 1623 338 100 1.68 1 125 1.68 9 200 1.68 446 300 1.68 1155 150 1.0 103 150 3.5 245 150 5.0 427 Methanol 323 100 3.0 6 125 3.0 96 150 3.0 257 200 3.0 698 300 3.0 1286 338 100 3.0 15 150 3.0 90 200 3.0 597 300 3.0 1325 150 1.0 86 150 5.0 178 150 10.0 435 1: Cosolvent in CO2. Synonym: 2-(Thiocyanatomethylthio) benzo[d]thiazole Source: Sahle-Demessie, E.; Pillai, U. R.; Junsophonsri, S.; Levien, K. L. J. Chem. Eng. Data (2003), 48(3), 541-547.

[T-40]

323 K 338 K

1000

Pure CO 2

500 0 50

150

250

350

250

350

P (bar) 2000 Acetone, 323 K Acetone, 338 K MeOH, 323 K MeOH, 338 K

1500 6

100 110 125 150 200 300 100 110 125 150 200 300

(mol%)

y x 10

323

P (bar)

1000

500

0 50

150 P (bar)

500

y x 106

T (K)

Cosolvent1)

250 Acetone MeOH

0 0

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5 Cosolvent (mol %)

10

764

Solubility in Supercritical Carbon Dioxide

Thioxanthone (C13H8OS; MW=212.27) 308

318

328

338

348

P (bar) 121 152 182 212 243 273 304 334 354 121 152 182 212 243 273 304 334 354 121 152 182 212 243 273 304 334 354 121 152 182 212 243 273 304 334 354 121 152 182 212 243 273 304

S (g/L) 0.09 0.11 0.12 0.16 0.18 0.19 0.20 0.25 0.24 0.05 0.10 0.15 0.18 0.22 0.22 0.28 0.31 0.30 0.05 0.09 0.16 0.23 0.28 0.32 0.35 0.41 0.45 0.00 0.05 0.14 0.22 0.30 0.36 0.42 0.51 0.53 0.00 0.04 0.12 0.23 0.34 0.44 0.53

yx

24 28 30 37 42 43 45 54 52 16 28 39 46 53 51 65 70 68 19 29 47 61 71 80 85 97 106 0 20 43 64 83 94 108 126 129 1 16 43 74 102 122 143

200

150

y x 106

T (K)

[T-41]

106

308 K 318 K 328 K 338 K 348 K

100

50

0 100

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200

300 P (bar)

400

Solubility Data T

765

334 354

0.61 0.66

158 168

Synonyms: Thioxanthen-9-one; 9-Thioxanthone Source: Shamsipur, M.; Karami, A. R.; Yamini, Y.; Sharghi, H.; Salimi, A. R. J. Chem. Eng. Data (2003), 48(5), 1088-1091.

Thymol (C10H14O; MW=150.22)

343

65 78 98 104 113 127 57 70 90 119 140

y x 10

470 830 2440 4140 7210 12560 540 510 440 1710 4490

15000

6

323

P (bar)

y x 10

T (K)

[T-42]

6

323 K 343 K

10000

5000

0 50

100

150

P (bar)

Synonym: 5-Methyl-2-(1-methylethyl)phenol Source: Mukhopadhyay, M.; De, S. K. J. Chem. Eng. Data (1995), 40(4), 909-913.

Titanocene dichloride (C10H10Cl2Ti; MW=249.00) 179 194 215 222 234 252 272 300

y x 10

8.6 10.5 13.4 15.0 16.8 23.2 31.8 33.9

40 6

337

P (bar)

y x 10

T (K)

[T-43]

6

20

0 150

Synonym: Dichlorobis(η5-cyclopenta dienyl) titanium Source : Wang, J.; Chen, J.; Yang, Y. Fluid Phase Equil. (2004), 220(2), 147-151.

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200

250 P (bar)

300

766

Solubility in Supercritical Carbon Dioxide

a -Tocopherol (C29H50O2; MW=430.71) 313

98.8 120.5 136.9 164.2 177.7 192.8 207.0 219.5 232.0 240.9 103.3 124.1 140.7 160.2 176.8 194.6 207.8 220.3 232.6 241.6

333

y x 10

300 500 800 800 1000 1100 1100 1500 1400 1700 100 200 300 700 600 1000 1000 1100 1300 1500

2000 313 K 333 K

1500 6

P (bar)

y x 10

T (K)

[T-44]

6

1000

500

0 50

150

250

P (bar)

Synonyms: (2R)-3,4-Dihydro-2,5,7,8-tetramethyl-2[(4R ,8R )-4,8,12-trimethyltridecyl]-2H-1-benzopyran-6ol; DL-a -Tocopherol; Vitamin E Source: Chen, C.-C.; Chang, C.-m. J.; Yang, P.-w.; Fluid Phase Equil. (2000), 175(1-2), 107-115.

a -Tocopherol (C29H50O2; MW=430.71) 1)

[T-45]

6

313.15 K 333.15 K 353.15 K

y x 10

6

y x 10 T (K) P (bar) S (g/L) 32 313.15 101.3 0.20 30000 82 121.6 0.58 144 152.0 1.11 247 202.7 2.04 348 20000 253.3 3.01 3 333.15 101.3 0.01 70 121.6 0.31 628 152.0 3.78 10000 2306 202.7 16.51 4120 253.3 32.05 9 353.15 101.3 0.02 117 121.6 0.35 0 1048 152.0 4.51 50 10411 202.7 62.10 30190 253.3 211.10 1: Calculated from S. Synonyms: (2R )-3,4-Dihydro-2,5,7,8-tetramethyl-2[(4R ,8R )-4,8,12-trimethyltridecyl]-2H-1-benzopyran-6ol; DL - a -Tocopherol; Vitamin E Source: Chrastil, J. J. Phys. Chem. (1982), 86(15), 3016-3021.

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150 P (bar)

250

Solubility Data T

767

a -Tocopherol (C29H50O2; MW=430.71)

333.15

353.15

86 112 123 154 187 214 247 291 57 106 154 164 184 237 293 56 85 103 135 204 232 254 295 296

y x 10

0 170 440 740 930 1180 1850 2330 0 130 400 570 670 1440 2110 0 120 140 180 610 760 1190 1700 1870

313.15 K 333.15 K 353.15 K

2000

6

313.15

P (bar)

y x 10

T (K)

[T-46]

6

1000

0 0

100

200

300

P (bar)

Synonyms: (2R)-3,4-Dihydro-2,5,7,8-tetramethyl-2[(4R,8R)-4,8,12-trimethyltridecyl]-2H-1-benzopyran-6ol; DL-a -Tocopherol; Vitamin E Source: Fang, T.; Goto, M.; Yun, Z.; Ding, X.-l.; Hirose, T. J. Supercrit. Fluids (2004), 30(1), 1-16.

a -Tocopherol (C29H50O2; MW=430.71) T (K) 313

P (bar) 199 219 239 259 279 299 319 349

W (g/kg) 13.7 16.3 18.1 20.2 23.6 25.5 25.7 27.7

6

y x 10

1420 1690 1880 2100 2460 2670 2690 2900

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[T-47]

768

Solubility in Supercritical Carbon Dioxide

4000 199 10.6 1090 219 13.6 1410 239 17.1 1770 259 19.8 2060 3000 279 22.9 2390 299 25.1 2620 319 29.4 3090 349 33.9 3570 2000 353 199 6.2 640 219 10.1 1040 239 14.4 1490 1000 259 17.3 1800 279 19.9 2070 299 23.0 2410 319 28.4 2980 0 349 33.2 3500 100 Synonyms: (2R)-3,4-Dihydro-2,5,7,8-tetramethyl-2[(4R,8R)-4,8,12-trimethyltridecyl]-2H-1-benzopyran-6ol; DL-α-Tocopherol; Vitamin E Source: Johannsen, M. ; Brunner, G. J. Chem. Eng. Data (1997), 42(1), 106-111. 333

y x 10

6

313 K 333 K 353 K

200

300 P (bar)

a -Tocopherol (C29H50O2; MW=430.71)

333

353

84.5 105.5 135.5 153.0 175.5 199.0 230.5 254.0 275.0 78.5 125.5 172.5 231.5 255.5 259.5 283.5 197.5 201.5 206.5 227.5 250.5 250.5

w x 10

1000 1700 2200 6200 7700 6500 5200 9200 8900 200 500 1600 6700 9700 8900 16700 3400 3800 4100 6700 8400 11100

y x 10

100 170 220 640 790 660 540 940 920 20 50 170 690 1000 910 1730 350 390 420 690 860 1140

2000 313 K 333 K 353 K

1500 6

313

P (bar)

[T-48]

6

y x 10

T (K)

6

400

1000

500

0 50

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150

250 P (bar)

350

Solubility Data T

769

269.5 11400 1180 278.5 10900 1120 301.0 15100 1560 303.0 13900 1430 Synonyms: (2R)-3,4-Dihydro-2,5,7,8-tetramethyl-2[(4R ,8R )-4,8,12-trimethyltridecyl]-2H-1-benzopyran-6ol; DL- a -Tocopherol; Vitamin E Source: Skerget, M.; Kotnik, P.; Knez, Z. J. Supercrit. Fluids (2003), 26(3), 181-191.

d -Tocopherol (C27H46O2; MW=402.65)

333

353

W (g/kg)

199 219 239 259 279 299 319 349 199 219 239 259 279 299 319 349 199 219 239 259 279 299 319 349

9.7 10.4 11.7 15.1 21.2 25.0 27.3 30.8 7.9 11.7 17.5 20.8 25.7 31.7 37.1 40.2 4.9 6.7 11.9 13.8 18.6 19.4 25.5 32.6

y x 10

1080 1150 1300 1680 2370 2790 3060 3460 870 1290 1950 2320 2880 3560 4200 4560 540 740 1310 1530 2070 2160 2850 3670

5000 313 K 333 K 353 K

6

313

P (bar)

[T-49]

6

y x 10

T (K)

1)

2500

0 150

1: The equilibrium solubility was measured in a quasistatic apparatus. (See the table below.) Synonyms: [2R [2R*(4R*,8R*)]]-3,4-Dihydro-2,8dimethyl-2-(4,8,12-trimethyltridecyl)-2H-benzopyran-6ol; D-d-Tocopherol Source: Johannsen, M. ; Brunner, G. J. Chem. Eng. Data (1997), 42(1), 106-111.

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250 P (bar)

350

770

Solubility in Supercritical Carbon Dioxide

d -Tocopherol (C27H46O2; MW=402.65)

[T-50]

y x 10 T (K) P (bar) 306.1 93.5 180 122.5 310 153.0 490 176.0 600 211.0 630 1600 246.0 830 257.5 870 313.1 96.5 80 124.0 270 1200 153.5 450 210.0 760 239.0 900 800 246.0 880 323.1 90.5 80 119.0 220 150.5 440 400 176.0 710 209.5 1050 237.0 1150 250.5 1220 0 263.0 1210 50 333.1 94.0 120 122.0 160 152.0 400 180.0 530 211.0 810 241.0 910 252.0 1190 264.0 1350 1: The equilibrium solubility was measured in a flow apparatus. (See the table above). Synonyms: [2R [2R*(4R*,8R*)]]-3,4-Dihydro-2,8dimethyl-2-(4,8,12-trimethyltridecyl)-2H-benzopyran-6ol; D-d-Tocopherol Source: Pereira, P. J.; Coto, B.; Menduina, C.; de Azevedo, E. G.; da Ponte, M. N. Fluid Phase Equil.(2004), 216(1), 53-57. 6

y x 10

6

306.1 K 313.1 K 323.1 K 333.1 K

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150 P (bar)

250

Solubility Data T

771

Triacontane (C30H62; MW=422.81) S (g/L)

y x 10

0.033 308.15 90 5.1 0.075 100 10.0 0.122 110 16.5 0.159 120 20.0 0.288 140 35.1 0.319 160 38.2 0.360 180 42.0 0.432 200 50.3 0.482 250 53.6 0.071 318.15 105 13.5 0.161 110 28.3 0.292 115 47.9 0.459 120 72.1 0.801 140 116.3 1.526 160 208.9 1.967 180 258.8 2.038 200 260.1 2.477 250 301.3 Source: Reverchon, E.; Russo, P.; Stassi, A. J. Chem. Eng. Data (1993), 38(3), 458-460.

308.15 K 318.15 K

300

6

P (bar)

y x 10

T (K)

[T-51]

6

200

100

0 50

Tributyl phosphate (C12H27O4P ; MW=266.31) T (K) 303

313

323

P (bar)

M (mol/L)

85 100 150 200 250 85 100 150 200 250 75 85 90 100

1.300 1.400 1.400 1.500 1.400 0.760 1.200 1.300 1.400 1.400 0.009 0.070 0.170 0.730

y1) x 106 72600 73700 67600 68900 62500 83100 76700 68100 68200 65300 2110 12100 25200 75600

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150

250

P (bar)

[T-52]

772

Solubility in Supercritical Carbon Dioxide

y x 10

6

75200 150 1.300 72600 200 1.400 100000 73100 250 1.500 131 333 85 0.001 832 90 0.005 1909 93 0.011 20800 96 0.130 59200 100 0.420 66100 120 0.710 73600 150 1.100 50000 67700 200 1.200 67600 250 1.300 166 338 90 0.001 3270 100 0.020 31600 110 0.240 36100 120 0.330 72900 150 1.000 0 76100 200 1.300 0 74600 250 1.400 162 343 100 0.001 1130 105 0.007 20300 110 0.140 40600 115 0.310 79200 150 1.000 73800 200 1.200 71800 250 1.300 165 353 85 0.001 100 0.002 335 110 0.004 593 120 0.049 7150 150 0.650 62200 200 1.200 81200 250 1.300 76700 363 100 0.002 344 120 0.009 1460 150 0.430 48000 200 1.200 89500 250 1.200 76300 1: Calculated from M. Synonym: Phosphoric acid tributyl ester Source: Meguro, Y.; Iso, S.; Sasaki, T.; Yoshida, Z. Anal. Chem. (1998), 70(4), 774-779.

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303 K 323 K 343 K 363 K

100

200 P (bar)

300

Solubility Data T

773

Tributyrin (C15H26O6; MW=302.36) T (K)

P (bar)

S (g/L)

[T-53]

y1) x 106

60000

1110 101.3 4.92 3210 121.6 16.04 5530 152.0 30.01 10900 202.7 64.15 313 333.15 121.6 0.97 9100 152.0 38.80 16500 202.7 84.20 47300 253.3 270.10 1: Calculated from S. Synonyms: Glycerin tributyrate; Glycerol tributanoate; Tributanoin Source: Chrastil, J. J. Phys. Chem. (1982), 86(15), 3016-3021.

y x 106

313.15

40000

313.15 K 333.15 K

20000 0 100

150

200 P (bar)

Tributyrin (C15H26O6; MW=302.36) 40000 6

y3) x 106 320 34300 26100 22700 20800

[T-54]

y x 10

T (K) P1) (bar) S1) (g/L)2) 313.2 78 0.004 100 0.442 200 0.333 250 0.288 350 0.264

20000

1: Obtained by digitizing the graph in the original article. 2: Solubility unit in gram of solute per liter of CO2 at 293.15 K and 1 atm. 3: Calculated from S. Synonyms: Glycerin tributyrate; Glycerol tributanoate; Tributanoin Source: Hammam, H. J. Supercrit. Fluids (1992), 5(2), 101-106.

0 0

200

400

P (bar)

Tricaprin (C33H62O6; MW=554.84)

1: Obtained by digitizing the graph in the original article. 2: Solubility unit in gram of solute per liter of CO2 at 293.15 K and 1 atm. 3: Calculated from S. Synonyms: Glycerol tricaprate; Glycerin tridecanoate; Tridecanoin Source: Hammam, H. J. Supercrit. Fluids (1992), 5(2), 101-106.

20000 6

y3) x 106 4300 13200 18400 13800

[T-55]

y x 10

T (K) P1) (bar) S1) (g/L)2) 313.2 150 0.099 200 0.304 250 0.427 350 0.319

250

10000 0 100

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200

300 P (bar)

400

774

Solubility in Supercritical Carbon Dioxide

Tricaproin (C21H38O6; MW=386.52) y3) x 106 23200 19400 19300 19100

1: Obtained by digitizing the graph in the original article. 2: Solubility unit in gram of solute per liter of CO2 at 293.15 K and 1 atm. 3: Calculated from S. Synonyms: Glycerin trihexanoate; Glycerol tricaproate; Trihexanoin Source: Hammam, H. J. Supercrit. Fluids (1992), 5(2), 101-106.

30000 y x 106

T (K) P1) (bar) S1) (g/L)2) 313.2 150 0.377 200 0.315 250 0.313 350 0.308

[T-56]

20000 10000 100

200

300

Tricaprylin (C27H50O6; MW=470.68)

1: Obtained by digitizing the graph in the original article. 2: Solubility unit in gram of solute per liter of CO2 at 293.15 K and 1 atm. 3: Calculated from S. Synonyms: Glycerol tricaprylate; Glycerin trioctanoate; Trioctanoin Source: Hammam, H. J. Supercrit. Fluids (1992), 5(2), 101-106.

30000 6

y3) x 106 3160 11300 19300 18500 17800 18500

[T-57]

y x 10

T (K) P1) (bar) S1) (g/L)2) 313.2 100 0.061 125 0.220 150 0.380 200 0.365 250 0.350 351 0.365

15000

0 0

2,4',5-Trichlorobiphenyl (C12H7Cl3; MW=257.54) T (K) P (bar) 313 100 110 120 130 140 150 160 170 180

400

P (bar)

6

y x 10

710 925 1100 1210 1330 1420 1520 1590 1620

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200

400

P (bar)

[T-58]

Solubility Data T

775

313 K 323 K 333 K

y x 10

6

190 1690 200 1780 220 1830 240 1890 260 2020 4000 280 2070 300 2150 323 100 251 110 484 3000 120 754 130 1010 140 1210 150 1370 2000 160 1520 170 1650 180 1830 190 1880 1000 200 1990 220 2190 240 2370 0 260 2570 280 2680 50 300 2810 333 100 211 110 294 120 466 130 682 140 926 150 1170 160 1410 170 1620 180 1800 190 1980 200 2200 220 2510 240 2770 260 3070 280 3260 300 3510 Source: Anitescu, G.; Tavlarides, L. L. J. Supercrit. Fluids (1999), 14(3), 197-211.

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150

250 P (bar)

350

776

Solubility in Supercritical Carbon Dioxide

2,4',5-Trichlorobiphenyl (C12H7Cl3; MW=257.54) P (bar)

313

100 110 120 130 140 150 160 170 180 190 200 220 240 260 280 300 100 110 120 130 140 150 160 170 180 190 200 220 240 260 280 300 100 110 120 130 140 150 160 170 180 190 200 220

323

333

n -Butane (mol%)

5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0

[T-59]

y x 106 992 1270 1450 1590 1730 1840 1940 2010 2050 2110 2160 2250 2340 2420 2490 2580 361 685 1060 1370 1620 1810 1980 2130 2260 2370 2460 2670 2850 3010 3140 3280 314 430 639 971 1290 1590 1870 2100 2290 2470 2680 3000

4000 313 K 323 K 333 K

3000

y x 106

T (K)

1)

2000

1000

0 50

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150

250 P (bar)

350

Solubility Data T

777

5.0 5.0 5.0 5.0

240 260 280 300

3270 3540 3760 3930

1: Cosolvent in CO2. Source: Anitescu, G.; Tavlarides, L. L. J. Supercrit. Fluids (1999), 14(3), 197-211.

2,4',5-Trichlorobiphenyl (C12H7Cl3; MW=257.54) P (bar)

Methanol1) (mol%)

313

100 110 120 130 140 150 160 170 180 190 200 220 240 260 280 300 100 110 120 130 140 150 160 170 180 190 200 220 240 260 280 300

5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0

323

y x 106 930 1170 1350 1490 1600 1680 1760 1820 1870 1910 1960 2050 2120 2200 2270 2340 354 661 1010 1330 1560 1750 1910 2040 2150 2250 2360 2560 2740 2920 3050 3180

4000 313 K 323 K 333 K

3000

y x 106

T (K)

[T-60]

2000

1000

0 50

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150

250 P (bar)

350

778

Solubility in Supercritical Carbon Dioxide

333

100 110 120 130 140 150 160 170 180 190 200 220 240 260 280 300

5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0

302 423 632 941 1260 1550 1820 2030 2250 2440 2630 2950 3210 3440 3670 3860

1: Cosolvent in CO2. Source: Anitescu, G.; Tavlarides, L. L. J. Supercrit. Fluids (1999), 14(3), 197-211.

Tridecafluorooctyl 2,5-dichlorobenzoate (C15H7Cl2F13O2; MW=537.10) P (bar)

y x 106

317.25 96.0 1700 333.45 119.7 1700 354.15 144.6 1700 375.35 158.7 1700 314.95 94.6 9200 330.05 128.2 9200 348.55 162.1 9200 366.05 187.4 9200 365.55 199.8 25800 Synonym: 2,5-Dichlorobenzoic acid 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl ester Source: Shen, Z.; McHugh, M. A.; Lott, K. M.; Wright, M. E. Fluid Phase Equil. (2004), 216(1), 1-12.

250 200 P (bar)

T (K)

[T-61]

y=0.0017 y=0.0092 y=0.0258

150 100 50 300

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330

360 T (K)

390

Solubility Data T

779

1-Tridecanol (C13H28O; MW=200.36) T (K)

P (bar)

[T-62]

6

y x 10

84.1 145 95.1 328 103.7 1651 20000 120.8 4960 135.6 7109 147.3 9012 10000 165.6 11350 172.5 11770 185.2 13900 185.2 14180 0 195.5 14660 50 203.3 16610 224.3 23100 241.2 23070 Synonym: Tridecyl alcohol Source: Artal, M. ; Pauchon, V. ; Embid, J. M.; Jose, J. J. Chem. Eng. Data (1998), 43(6), 983-985.

y x 10

6

323.15

150 P (bar)

Triethylene glycol (C6H14O4; MW=150.17) y x 10

780 1290 6360

Synonyms: 2,2'-(Ethylenedioxy)diethanol; Triglycol Source: Eissler, R; Friedrich, J. P. J. Am. Oil Chem. Soc. (1988), 65(5), 764767.

[T-63]

8000 y x 106

T (K) P (bar) 325.15 344.7 551.6 689.5

6

250

4000 0 300

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500 P (bar)

700

780

Solubility in Supercritical Carbon Dioxide

Triethylene glycol (C6H14O4; MW=150.17)

[T-64]

6

313.2 K 323.2 K 333.2 K

y x 10

6

y x 10 T (K) P (bar) 150 313.2 27.6 0.83 41.4 1.37 55.2 2.72 69.0 11.50 82.7 35.89 100 96.5 85.93 323.2 27.6 2.33 41.4 3.37 55.2 3.58 50 69.0 11.76 82.7 28.37 96.5 71.09 333.2 41.4 5.04 55.2 6.87 0 69.0 15.34 0 82.7 32.19 96.5 69.30 110.3 137.30 Synonyms: 2,2'-(Ethylenedioxy)diethanol; Triglycol Source: Yonemoto, T.; Charoensombut-Amon, T.; Kobayashi, R. Fluid Phase Equil. (1990), 55(1-2), 217229.

Triglycerides1) 2) T (K) P (bar) 202 313.15 256 302 354 401 453 498 557 600 202 323.15 263 300 367 408 448 496 546 602

50

100

P (bar)

[T-65] w2) x 106 350 5320 7450 10300 12800 15800 18100 20200 21900 3500 5780 8820 13400 16900 19300 22700 26200 29500

CAT4240—CHAPTER 20—1/11/2006—19:15—SRAM—XML MODEL C – pp. 735–808

Solubility Data T

353.15

1220 3800 7450 11000 16000 20800 26600 33200 38500 304 2890 5930 10300 15800 21100 29500

541

35700

562 248

39800 1370

299

5170

345

9280

397

15200

453

23700

500

33000

525

39700

40000

30000

313.15 K 323.15 K 333.15 K 343.15 K 353.15 K

6

343.15

202 250 300 343 399 439 496 553 602 200 252 297 352 404 448 503

w x 10

333.15

781

20000

10000

0 100

300

500

700

P (bar)

1: Extracted from soybean oil. 2: Obtained by digitizing the solubility isotherms in the source. The points are arbitrarily selected from the lines as there are no actual data points in the source graph. Source: King, J. W. J. Chromatogr. Sci. (1989), 27(7), 355-364.

Trihexylamine (C18H39N; MW=269.51)

[T-66]

6

60000

6

310 K 320 K

y x 10

y x 10 T (K) P (bar) 310 114.0 20700 134.5 37700 138.0 52500 320 111.5 6600 111.5 6900 141.5 25000 142.0 24400 155.0 44000 Synonym: N,N -Dihexyl-1-hexanamine Source: Schmitt, W. J.; Reid, R. C. Chem. Eng. Comm. (1988), 64, 155-176.

30000

0 100

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120

140 P (bar)

160

782

Solubility in Supercritical Carbon Dioxide

1,5,6-Trihydroxyxanthone (C13H8O5; MW=244.20)

318.15

328.15

338.15

348.15

S (g/L)

y x 10

74 112 152 193 233 274 314 355 74 112 152 193 233 274 314 355 74 112 152 193 233 274 314 355 74 112 152 193 233 274 314 355

0.86 1.25 1.74 2.29 2.53 2.70 3.41 3.67 0.73 0.95 1.65 2.19 2.45 2.91 3.68 4.05 0.56 0.79 1.52 1.99 2.87 3.27 4.47 5.11 0.59 0.80 1.37 2.12 3.32 4.16 5.38 6.28

466 285 371 469 502 523 646 683 650 280 397 489 522 600 739 792 568 329 416 483 651 707 933 1038 660 436 438 563 807 952 1179 1331

74 112 152 193 233

0.53 0.63 1.08 2.36 3.69

649 408 407 698 965

2000 305 K 318 K 328 K 338 K 348 K

1500

6

305.15

P (bar)

[T-67]

6

y x 10

T (K)

1)

1000

500

0 50

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150

250 P (bar)

350

Solubility Data T

783

274 314 355

4.90 6.55 7.60

1190 1509 1684

1: The y value at 305.15 K and 74 bar in the source do not agree with S and thus was re-calculated based on the S value. Synonym: 1,5,6-Trihydroxyxanthen-9-one Source: Ghiasvand, A. R.; Hosseini, M.; Sharghi, H.; Yamini, Y.; Shamsipur, M. J. Chem. Eng. Data (1999), 44(6), 1135-1138.

Triiodomethane (CHI3; MW=393.73) T (K)

P (bar)

4

M x10 (mol/L)

[T-68]

y1) x 106

312.73 K 326.95 K

y x 10

6

312.72 77.8 1.20 20.4 312.73 79.7 1.61 25.4 240 312.73 80.4 1.82 27.8 312.73 81.0 1.99 29.6 312.73 82.1 2.40 33.9 312.73 83.6 3.70 48.3 312.71 83.9 3.40 43.6 160 312.74 84.8 4.70 57.2 312.72 85.2 4.60 54.5 312.71 86.8 6.80 72.3 312.74 87.4 8.60 87.5 312.74 88.6 11.60 108.9 80 312.73 89.5 14.30 127.3 312.74 90.9 18.20 151.8 312.72 94.0 27.00 204.7 326.96 78.3 1.19 26.3 326.95 82.4 1.60 32.2 0 326.93 88.9 2.80 48.4 70 326.94 90.9 3.00 49.4 326.97 94.0 3.80 57.9 326.94 94.3 3.90 59.0 326.97 94.7 4.00 60.0 326.94 99.8 6.30 82.9 1: Calculated from M. Synonym: Iodoform Source: Gutkowski, K.; Japas, M. L.; Fernandez-Prini, R. J. Chem. Thermodyn. (1997), 29(10), 1077-1086.

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80

90 P (bar)

100

784

Solubility in Supercritical Carbon Dioxide

Trilaurin (C39H74O6; MW=639.00) T (K)

P (bar)

[T-69]

6

y x 10

12000

150 609 200 3859 250 4867 350 10520 313 150 481 8000 200 2915 250 5994 300 7890 350 11300 4000 400 11360 323 200 2608 250 3767 350 7736 0 333 200 2582 250 3935 100 350 8557 Synonyms: Glycerin tridodexanoate; Glycerol trilaurate; Tridodecanoin Source: Ashour, I.; Hammam, H. J. Supercrit. Fluids (1993), 6(1), 3-8. (Also, see the graph in Hammam, H. J. Supercrit. Fluids (1992), 5(2), 101-106.)

308 K 313 K 323 K 333 K

y x 10

6

308

200

300 P (bar)

Trilaurin (C39H74O6; MW=639.00) 91 111 151 151 200 253

y x 106

13 228 874 902 1830 3370 Synonyms: Glycerin tridodecanoate; Glycerol trilaurate; Tridodecanoin Source: Bamberger, T.; Erickson, J. C.; Cooney, C. L.; Kumar, S. K. J. Chem. Eng. Data (1988), 33(3), 327-333.

4000 6

313

[T-70]

y x 10

T (K) P (bar)

400

2000

0 50

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150 P (bar)

250

Solubility Data T

785

[T-71]

Trilaurin (1) + Trimyristin (2) Mixture 92 110 151 152 152 152 199 249

y1 x 106 19 144 581 560 567 572 1110 1890

y2 x 106 1.8 29.9 116.0 113.0 131.0 136.0 311.0 486.0

2000 Trilaurin Trimyristin 6

313

P (bar)

y x 10

T (K)

1000

0

Source: Bamberger, T.; Erickson, J. C.; Cooney, C. L.; Kumar, S. K. J. Chem. Eng. Data (1988), 33(3), 327-333.

75

175 P (bar)

[T-72]

Trilaurin (1) + Trimyristin (2) + Tripalmitin (3) Mixture 92 111 150 150 151 151 153 199 250

y1 x 106 17 149 462 476 663 608 528 902 1620

y2 x 106 4.0 41.2 141.0 131.0 87.4 77.5 136.0 325.0 507.0

y3 x 106 0.20 2.78 10.30 10.40 11.10 9.53 11.90 35.50 47.50

Trilaurin Trimyristin Tripalmitin

1500 6

313

P (bar)

y x 10

T (K)

1000 500 0

Source: Bamberger, T.; Erickson, J. C.; Cooney, C. L.; Kumar, S. K. J. Chem. Eng. Data (1988), 33(3), 327333.

50

150

[T-73]

P (bar) 91 111 152 153 200 247

y1 x 10

13 218 868 859 1660 2830

y2 x 10

0.05 0.52 6.09 6.26 24.30 62.00

Source: Bamberger, T.; Erickson, J. C.; Cooney, C. L.; Kumar, S. K. J. Chem. Eng. Data (1988), 33(3), 327-333.

3000 Trilaurin Tripalmitin

6

313

6

y x 10

T (K)

250

P (bar)

Trilaurin (1) + Tripalmitin (2) Mixture 6

275

1500

0 75

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150 P (bar)

225

786

Solubility in Supercritical Carbon Dioxide

Trilinolein (C57H98O6; MW=879.38) T (K)

P (bar)

S (g/L)

1)

y x 10

[T-74] 6

600

6.8 81.1 0.04 40.5 101.3 0.52 73.9 121.6 1.07 176.0 253.3 3.10 8.3 333.15 101.3 0.05 53.2 121.6 0.48 228.0 152.0 2.80 0 504. 202.7 7.35 1: Calculated from S. Synonyms: Glycerin trilinoleate; Glycerol trilinoleate Source: Chrastil, J. J. Phys. Chem. (1982), 86(15), 3016-3021.

y x 10

6

313.15

313.15 K 333.15 K

400 200 0 50

150

250

P (bar)

Trimyristin (C45H86O6; MW=723.16) T (K)

P (bar)

[T-75]

y x 106

6

y x 10

95 12.3 111 55.5 152 192.0 153 215.0 154 200.0 202 343.0 249 422.0 304 495.0 Synonyms: Glycerin trimyristate; Glycerol tritetradecanoate Source: Bamberger, T.; Erickson, J. C.; Cooney, C. L.; Kumar, S. K. J. Chem. Eng. Data (1988), 33(3), 327-333.

600

313

300

0 50

150

250 P (bar)

[T-76]

Trimyristin (1) + Tripalmitin (2) Mixture 92 110 151 152 153 200 250 304

y1 x 10

5.0 55.0 129.0 131.0 135.0 284.0 407.0 483.0

y2 x 10

0.35 3.20 11.30 11.30 10.50 26.90 32.20 38.50

Source: Bamberger, T.; Erickson, J. C.; Cooney, C. L.; Kumar, S. K. J. Chem. Eng. Data (1988), 33(3), 327-333.

600

6

313

P (bar)

6

y x 10

T (K)

6

350

Trimyristin Tripalmitin

400 200 0 0

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100

200 P (bar)

300

400

Solubility Data T

787

Trinitrotoluene (C7H5N3O6; MW=227.13)

303

308

323 338 353

P (bar) 138 379 276 414 483 138 276 414 483 276 414 276 276

W (g/kg)

y x 10

4.9 13.3 17.0 32.3 39.6 9.6 18.4 34.8 50.6 19.4 45.6 19.8 19.4

950 2570 3280 6220 7610 1860 3550 6700 9710 3740 8760 3820 3740

[T-77]

12000

6

293

6

293 K 303 K 308 K 323 K 338 K 353 K

8000

y x 10

T (K)

1)

4000

0 0

200

400 P (bar)

1: Calculated from W. Synonyms: 2,4,6-Trinitrotoluene; TNT Source: Agrawal, P. M.; Rice, B. M.; Sorescu, D. C.; Thompson, D. L. Fluid Phase Equil. (2001), 187-188, 139-153.

Trinitrotoluene (C7H5N3O6; MW=227.13) T (K)

P (bar)

S (g/L)

1)

y x 10

600

6

138 4.27 1031 253 9.97 2130 379 14.43 2886 323.15 138 2.84 820 253 11.55 2660 379 16.51 3481 343.15 138 5.93 2539 253 18.92 4909 379 25.64 5833 1: Calculated form S. Synonyms: 2,4,6-Trinitrotoluene; TNT Source: Ashraf-Khorassani, M.; Taylor, L. T. J. Chem. Eng. Data (1999), 44(6), 1254-1258.

y x 10

6

308.15

[T-78]

6000

4000

2000

308 K 323 K 343 K

0 100

CAT4240—CHAPTER 20—1/11/2006—19:16—SRAM—XML MODEL C – pp. 735–808

200

300 P (bar)

400

788

Solubility in Supercritical Carbon Dioxide

Trioctylamine (C24H51N; MW=353.67) y x 106

10000 6

832 3060 3000 6250 6690 7990 8000

y x 10

T (K) P (bar) 320 110.5 141.5 142.0 201.0 201.0 235.0 235.0

[T-79]

5000

0 100

Synonyms: Tricaprylylamine; Tri-n-octylamine Source: Schmitt, W. J.; Reid, R. C. Chem. Eng. Comm. (1988), 64, 155-176.

150

200

250

P (bar)

Trioctylphosphine (C24H51P; MW=370.64)

[T-80]

6

6

10000 y x 10

y x 10 T (K) P (bar) 320 111 970 141 2830 191 5860 254 8650 Synonym: Tri-n -octylphosphine Source: Schmitt, W. J.; Reid, R. C. Chem. Eng. Comm. (1988), 64, 155-176.

5000

0 100

200

300

P (bar)

Trioctylphosphine oxide (C24H51OP; MW=386.63) T (K)

P (bar)

6

y x 10

2280 111 4740 140 12300 203 510 320 111 2290 140 7870 203 Synonym: Tri-n -octylphosphine oxide Source: Schmitt, W. J.; Reid, R. C. Chem. Eng. Comm. (1988), 64, 155-176.

[T-81]

13000

310

y x 10

6

310 K 320 K

6500

0 100

140

180 P (bar)

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220

Solubility Data T

789

Triolein (C57H104O6; MW=885.43) T (K)

P (bar)

[T-82]

y x 106

313

313 K 333 K

600

y x 10

6

102.4 200 123.7 200 141.6 300 160.5 300 177.4 400 194.0 400 208.3 400 218.8 500 231.4 600 239.9 600 333 101.2 100 123.6 200 141.0 200 159.6 200 179.5 300 200.2 300 211.7 300 223.0 400 230.9 400 242.1 400 Synonyms: Glycerin trioleate; Glycerol triolein Source: Chen, C.-C.; Chang, C.-M. J.; Yang, P.-W.; Fluid Phase Equil. (2000), 175(1-2), 107-115.

400

200

0 50

150

Triolein (C57H104O6; MW=885.43) y x 10

2 60 144 188 245 2 24 292 464 602 6 27 580 1730 2740 12 46 739 2790 5130

6000 313.15 K 323.15 K 343.15 K 353.15 K

4000 6

S (g/L) 0.01 0.78 2.27 3.19 4.35 0.01 0.20 4.16 7.37 10.17 0.02 0.14 6.06 23.25 41.05 0.04 0.21 6.53 33.91 71.86

[T-83] 6

y x 10

T (K) P (bar) 313.15 81.1 101.3 152.0 202.7 253.3 323.15 81.1 101.3 152.0 202.7 253.3 343.15 81.1 101.3 152.0 202.7 253.3 353.15 81.1 101.3 152.0 202.7 253.3

1)

250

P (bar)

2000

0 50

1: Calculated from S. Synonyms: Glycerin trioleate; Glycerol triolein Source: Chrastil, J. J. Phys. Chem. (1982), 86(15), 3016-3021.

CAT4240—CHAPTER 20—1/11/2006—19:16—SRAM—XML MODEL C – pp. 735–808

150 P (bar)

250

790

Solubility in Supercritical Carbon Dioxide

Triolein (C57H104O6; MW=885.43) T (K)

P (bar)

w (wt%)

1)

[T-84]

y x 10

6

6

323.15 K 333.15 K

y x 10

172 0.11 55 206 0.25 124 241 0.41 204 275 0.60 299 309 0.75 374 333.15 172 0.06 30 199 0.12 60 206 0.14 69 241 0.31 154 275 0.53 264 309 0.76 379 1: Calculated from w. Synonyms: Glycerin trioleate; Glycerol triolein Source: Nilsson, W. B.; Gauglitz, E. J. Jr.; Hudson, J. K.J. Am. Oil Chem. Soc. (1991), 68(2), 87-91.

400

323.15

200

0 150

200

250 P (bar)

Triolein (C57H104O6; MW=885.43)

82 85 87 94 97 99 110 115 123 124 128 133 136 145 146 159 170 176 180 185 198 203

W (g/kg CO2) 78 86 90 98 105 112 109 114 112 113 116 109 112 115 117 123 117 118 120 124 129 133

y1) x 106 3860 4260 4450 4850 5190 5540 5390 5630 5540 5590 5730 5390 5540 5680 5780 6080 5780 5830 5930 6130 6370 6570

308 K 313 K 318 K 323 K 328 K

11000

6

308

P (bar)

[T-85]

y x 10

T (K)

300

8000

5000

2000 50

CAT4240—CHAPTER 20—1/11/2006—19:16—SRAM—XML MODEL C – pp. 735–808

100

150 P (bar)

200

Solubility Data T

313

318

791

81

77

3810

84

77

3810

92

96

4750

99

102

5040

108

116

5730

114

117

5780

119

126

6220

123 130 134 140 143 150 151 158 162 172 180 182 190 204 80 85 100 105 120 121 122 130 131 138 139 142 144 149 154 158 167 176 180 188 190 194 200

130 135 137 145 146 151 147 153 155 158 160 158 158 162 127 140 162 164 181 180 171 188 178 177 184 193 199 202 206 212 225 233 234 239 231 241 234

6420 6670 6760 7160 7210 7450 7250 7550 7650 7790 7890 7790 7790 7990 6270 6910 7990 8090 8920 8870 8430 9260 8770 8720 9060 9500 9790 9940 10100 10400 11100 11400 11500 11700 11400 11800 11500

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792

Solubility in Supercritical Carbon Dioxide

323

328

80 90 93 100 110 120 122 129 130

50 86 87 89 91 114 107 107 118

2480 4260 4310 4400 4500 5630 5290 5290 5830

131

115

5680

139

122

6030

140

123

6080

146

136

6710

147

133

6570

148

129

6370

150 155

136 145

6710 7160

164

152

7500

168

145

7160

180

160

7890

187

165

8140

188

166

8180

193

162

7990

199

170

8380

209

166

8180

210

175

8620

100

80

3960

102

87

4310

113

88

4360

114

95

4700

119

98

4850

120

104

5140

125

108

5340

130

117

5780

137

118

5830

138

119

5880

144

144

7110

146

133

6570

150

137

6760

160

135

6670

CAT4240—CHAPTER 20—1/11/2006—19:16—SRAM—XML MODEL C – pp. 735–808

Solubility Data T

793

170

137

6760

177

146

7210

182

131

6470

187

143

7060

195

145

7160

198

142

7010

204

150

7400

1: Calculated from W. Synonyms: Glycerin trioleate; Glycerol triolein Source: Ribeiro, M. A.; Bernardo-Gil, M. G. J. Chem. Eng. Data (1995), 40(6), 1188-1192.

Triolein (C57H104O6; MW=885.43) T (K)

P (bar)

W (g/kg)

1)

y x 10

[T-86] 6

172 2.1 100 207 3.3 160 241 4.9 240 276 6.2 310 310 7.0 350 1: Calculated from W. Synonyms: Glycerin trioleate; Glycerol triolein Source: Nilsson, W. B.; Hudson, J. K. J. Am. Oil Chem. Soc. (1993), 70(8), 749754.

400 y x 10

6

313.15

200

0 150

250 P (bar)

Tripalmitin (C51H98O6; MW=807.32)

[T-87]

y x 106

30 6

3.03 6.71 6.81 6.95 15.00 23.90 27.10 Synonyms: Glycerin tripalmitate; Glycerol trihexadecanoate Source: Bamberger, T.; Erickson, J. C.; Cooney, C. L.; Kumar, S. K. J. Chem. Eng. Data (1988), 33(3), 327-333.

y x 10

T (K) P (bar) 313 122 150 150 150 198 248 297

350

15

0 100

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200 P (bar)

300

794

Solubility in Supercritical Carbon Dioxide

Tripalmitin (C51H98O6; MW=807.32)

[T-88]

6

120 313.15 K 333.15 K 353.15 K

80 6

y x 10 T (K) P (bar) S (g/L) 5.5 313.15 81.1 0.03 36.5 101.3 0.43 47.4 121.6 0.63 54.8 152.0 0.79 64.0 202.7 0.99 69.7 253.3 1.13 5.5 333.15 81.1 0.02 12.7 101.3 0.07 27.8 121.6 0.23 54.1 152.0 0.61 75.4 202.7 1.01 90.2 253.3 1.31 6.6 353.15 81.1 0.02 12.0 101.3 0.05 23.2 121.6 0.13 41.0 152.0 0.33 78.6 202.7 0.87 107.0 253.3 1.36 1: Calculated from S. Synonyms: Glycerin tripalmitate; Glycerol trihexadecanoate Source: Chrastil, J. J. Phys. Chem. (1982), 86(15), 3016-3021.

y x 10

1)

40

0 0

100

200 P (bar)

Tripalmitin (C51H98O6; MW=807.32)

[T-89] 800 313.15 K 373.15 K

6

600 y x 10

y x 106 T (K) P (bar) 313.15 150 2.71 198 10.50 248 27.60 297 33.50 350 43.50 373.15 150 0.01 198 1.06 248 53.70 297 178.0 350 673.0 Synonyms: Glycerin tripalmitate; Glycerol trihexadecanoate Source: Miller, D. J.; Hawthorne, S. B. Anal. Chem. (1995), 67(2), 273-279.

300

400 200 0 100

CAT4240—CHAPTER 20—1/11/2006—19:16—SRAM—XML MODEL C – pp. 735–808

200

300 P (bar)

400

Solubility Data T

795

Tripalmitin (C51H98O6; MW=807.32) T (K)

P (bar)

W (g/kg)

1)

y x 10

[T-90]

6

313.15

172 0.28 15 207 0.32 17 276 0.38 21 310 0.38 21 333.15 172 0.90 49 207 2.30 126 241 4.40 241 276 7.90 434 310 10.80 595 1: Calculated from W. Synonyms: Glycerin tripalmitate; Glycerol trihexadecanoate Source: Nilsson, W. B.; Hudson, J. K. J. Am. Oil Chem. Soc. (1993), 70(8), 749-754.

600

y x 10

6

313.15 K 333.15 K

300

0 150

250 P (bar)

Triphenylamine (C18H15N; MW=245.32) 310 320

204 655 110 36 141 218 201 781 Synonym: N,N-Diphenylbenzenamine Source: Schmitt, W. J.; Reid, R. C. Chem. Eng. Comm. (1988), 64, 155-176.

1000 310 K 320 K

6

P (bar)

[T-91]

y x 106

y x 10

T (K)

350

500

0 100

150

200

P (bar)

Triphenylene (C18H12; MW=228.29) T (K) 308.15

P (bar) 85 91 103 116 132 149 168 192 221 247

y x 106 3.14 5.50 8.38 11.10 13.70 15.70 18.50 20.50 22.70 24.50

CAT4240—CHAPTER 20—1/11/2006—19:16—SRAM—XML MODEL C – pp. 735–808

[T-92]

796

328.15

1.01 3.98 7.86 9.18 12.90 17.60 23.30 25.90 30.10 32.80 1.15 3.05 7.89 15.20 23.50 31.80 37.40 42.20

50 308.15 K 318.15 K 328.15 K

40

6

96 105 116 119 135 152 172 192 223 252 107 117 133 155 177 197 222 251

30

y x 10

318.15

Solubility in Supercritical Carbon Dioxide

20 10 0 50

100

150

200

P (bar)

Synonyms: 9,10-Benzophenanthrene: 1,2,3,4-Dibenznaphthalene Source: Barna, L.; Blanchard, J.-M.; Rauzy, E.; Berro, C. J. Chem. Eng. Data (1996), 41(6), 1466-1469.

Triphenylene (C18H12; MW=228.29) 308.15

121.6 152.0 182.4 212.8 243.2 273.6 304.0 334.4 354.6 121.6 152.0 182.4 212.8 243.2 273.6 304.0 334.4 354.6

318.15

y x 106 12 16 18 21 24 25 27 29 32 10 16 21 26 30 33 36 38 40

100

75

308.15 K 318.15 K 328.15 K 338.15 K 348.15 K

6

P (bar)

[T-93]

y x 10

T (K)

250

50

25

0 100

CAT4240—CHAPTER 20—1/11/2006—19:16—SRAM—XML MODEL C – pp. 735–808

200

300 P (bar)

400

Solubility Data T

328.15

338.15

348.15

797

121.6 152.0 182.4 212.8 243.2 273.6 304.0 334.4 354.6 121.6 152.0 182.4 212.8 243.2 273.6 304.0 334.4 354.6

6 15 23 31 37 43 46 53 55 3 12 23 36 45 54 61 69 72

121.6

2

152.0

10

182.4

22

212.8

40

243.2

53

273.6

64

304.0

77

334.4 354.6

88 95

Synonyms: 9,10-Benzophenanthrene: 1,2,3,4Dibenznaphthalene Source: Yamini, Y.; Bahramifar, N., J. Chem. Eng. Data (2000), 45(1), 53-56.

Triphenylmethane (C19H16; MW=244.33) T(K) P(bar) 303.15 69.9 104.4 118.1 138.8 207.7 276.7 345.6 380.1 414.5

6

y x 10

9.4 699.0 831.0 697.0 1270.0 1400.0 1570.0 1690.0 1500.0

CAT4240—CHAPTER 20—1/11/2006—19:16—SRAM—XML MODEL C – pp. 735–808

[T-94]

798

Solubility in Supercritical Carbon Dioxide

3000

323.15

44.4 551.0 1030.0 1620.0 1950.0 2210.0 111.0 610.0 1170.0 2190.0 2630.0 2680.0 2470.0

2000 6

83.7 104.4 138.8 207.8 276.7 345.6 104.3 138.8 173.3 207.8 345.6 380.1 414.5

y x 10

313.15

Synonym: 1,1',1''-Methylidynetrisbenzene Source: Johnston, K. P.; Ziger, D. H.; Eckert, C. A. Ind. Eng. Chem. Fund.(1982), 21(3), 191-197.

1000 303.15 K 313.15 K 323.15 K

0 50

150

250

350

Triphenylmethane (C19H16; MW=244.33) 308.15

70.5 70.8 73.7 74.7 75.0 75.3 78.1 78.5 82.5 83.1 87.5 96.6 97.5 108.1 108.4 117.9 118.8 127.0 127.5 136.4 137.8 147.0 147.3 162.0 162.0 170.9 171.4 178.5 180.5

6

y x 10

39 55 36 68 61 37 230 315 483 485 568 671 776 789 922 918 1050 1070 1150 1150 1250 1230 1330 1430 1420 1510 1560 1550 1640

4000

308.15 K 318.15 K 328.15 K

3000 6

P (bar)

[T-95]

y x 10

T (K)

450

P (bar)

2000

1000

0

CAT4240—CHAPTER 20—1/11/2006—19:16—SRAM—XML MODEL C – pp. 735–808

50

150 P (bar)

250

Solubility Data T

318.15

799

188.0 188.8 205.6 206.6 244.9 246.5 262.5 263.7 283.7

1630 1640 1750 1690 1940 1930 2030 1980 2050

65.0 65.3 68.9 70.5 74.0 74.7 79.1 79.4 85.3 93.0 93.6 102.2 103.1 111.0 112.5 121.9 122.2 132.0 132.3 140.5 140.8 149.4 150.2 160.1 160.1 167.2 167.7 175.9 178.2 188.6 188.6 204.1 205.1 222.5 222.5 240.6 241.4 259.5 261.4 279.4 280.8

75 61 62 32 110 143 73 46 42 91 91 457 354 670 647 945 906 1110 1130 1370 1310 1560 1580 1810 1650 1890 1790 1970 1940 2160 2110 2320 2370 2460 2570 2820 2780 2980 2960 3070 3040

CAT4240—CHAPTER 20—1/11/2006—19:16—SRAM—XML MODEL C – pp. 735–808

800

328.15

Solubility in Supercritical Carbon Dioxide

66.3 67.0 70.2 70.5 75.3 75.6 79.7 79.7 85.0 85.0 89.9 90.2 96.9 97.5 106.4 107.2 116.8 117.1 128.7 128.4 137.2 145.7 147.0 155.3 155.9 164.3 165.9 173.5 174.0 189.3 189.9 208.5 226.1 226.4 242.5 243.0 262.5 263.1 280.2 280.2

48 76 74 293 85 98 128 75 90 55 75 70 142 174 281 250 460 493 758 738 1070 1340 1360 1630 1660 1840 1890 2200 2050 2310 2460 2760 3080 3170 3520 3500 3770 3880 3890 3980

Synonym: 1,1',1''-Methylidynetrisbenzene Source: Pauchon, V.; Cisse, Z.; Chavret, M.; Jose, J. J. Supercrit. Fluids (2004), 32 (1-3), 115-121.

CAT4240—CHAPTER 20—1/11/2006—19:16—SRAM—XML MODEL C – pp. 735–808

Solubility Data T

801

Triphenylphosphate (C18H15O4P; MW 326 28) T (K)

P (bar)

[T-96]

6

y x 10

310 K 320 K

6

y x 10

112.5 1070 142.5 1760 207.0 2660 281.0 3740 320 112.5 320 142.5 1020 207.0 2280 281.0 3380 Synonym: Phosphoric acid triphenyl ester Source: Schmitt, W. J.; Reid, R. C. Chem. Eng. Comm. (1988), 64, 155-176.

4000

310

2000

0 100

200 P (bar)

Triphenylphosphine (C18H15P; MW=262.29)

[T-97]

6

y x 10

3000

593 823 972 1360 1830 287 633 1030 1670 2400

6

310 K 320 K

y x 10

T (K) P (bar) 310 110.5 126.0 151.0 201.0 281.0 320 110.5 126.0 151.0 201.0 281.0

1500

0 100

Synonym: Triphenylphosphorus Source: Schmitt, W. J.; Reid, R. C. Chem. Eng. Comm. (1988), 64, 155-176.

Triphenylphosphine (C18H15P; MW=262.29) T (K) 300

310

P (bar) 73 91 102 122 153 204 251 291 100 121 152 204 254 304

300

2

M x 10 (mol/L) 0.728 0.947 0.997 1.150 1.330 1.520 1.810 2.120 0.516 1.120 1.860 2.620 3.290 4.040

y1) x 106 442 531 544 605 672 735 849 974 330 653 1010 1340 1610 1920

CAT4240—CHAPTER 20—1/11/2006—19:16—SRAM—XML MODEL C – pp. 735–808

200

300

P (bar)

[T-98]

802

Solubility in Supercritical Carbon Dioxide

320

300 K 310 K 320 K 330 K

y x 10

6

100 0.064 62 121 0.426 292 152 1.380 827 202 2.960 1610 6000 253 3.770 1940 303 4.840 2400 330 79 0.712 1600 85 0.534 1050 4000 90 0.266 469 95 0.181 285 100 0.146 205 102 0.137 183 110 0.107 119 2000 115 0.179 179 120 0.261 238 130 0.503 401 137 1.180 882 0 151 2.420 1660 0 177 5.300 3290 201 6.000 3520 228 8.480 4760 252 10.100 5490 279 10.600 5600 303 11.900 6150 1: Calculated from M. Synonym: Triphenylphosphorus Source: Wagner, K.-D.; Dahmen, N.; Dinjus, E., J. Chem. Eng. Data (2000), 45(4), 672-677.

Tris(p -fluorophenyl)phosphine (C18H12F3P; MW=316.26) T (K) 300

310

P (bar) 70 73 76 79 83 87 90 95 100 106 110 85 87 89 91 93

M x 102 (mol/L) 5.80 7.30 8.50 10.00 11.30 12.70 14.30 15.80 17.20 18.50 20.20 0.85 1.65 2.41 3.23 3.77

y1) x 106 3600 4410 5030 5820 6470 7160 7980 8690 9340 9910 10700 706 1260 1740 2250 2560

CAT4240—CHAPTER 20—1/11/2006—19:16—SRAM—XML MODEL C – pp. 735–808

100

200

300

P (bar)

[T-99]

Solubility Data T

4.84 6.00 7.90 9.50 10.90 12.90 16.00 18.30 20.50 23.00 24.10 0.44 1.09 1.87 3.25 4.57 6.05 7.48 8.10 9.30 13.10 15.50 20.30 18.20 23.80 25.50 28.60 32.90 35.00

3180 3790 4850 5700 6420 7450 9010 10100 11100 12200 12600 425 916 1410 2320 3130 4000 4840 5140 5760 7820 9140 11800 10500 13500 14300 15800 18100 19100

20000 300 K 310 K 320 K

15000

y x 106

320

96 101 106 111 116 122 131 140 150 160 172 100 105 111 116 121 126 130 134 140 151 155 161 163 170 175 182 186 189

803

10000

5000

0 50

1: Calculated from M. Synonym: Tris(4-fluorophenyl)phosphine Source: Wagner, K.-D.; Dahmen, N.; Dinjus, E., J. Chem. Eng. Data (2000), 45(4), 672-677.

CAT4240—CHAPTER 20—1/11/2006—19:16—SRAM—XML MODEL C – pp. 735–808

100

150 P (bar)

200

804

Solubility in Supercritical Carbon Dioxide

Tris(pentafluorophenyl)phosphine (C18F15P; MW=532.14) T (K)

P (bar)

2

M x 10 (mol/L)

[T-100]

y1) x 106

300

300 K 310 K 320 K

y x 10

6

69 10.30 6440 72 13.80 8370 74 15.00 8970 79 15.30 8880 80 16.80 9700 82 16.50 9450 86 17.90 10100 20000 88 19.90 11100 90 18.70 10400 95 22.00 12100 103 21.50 11600 15000 110 24.00 12700 120 25.90 13500 310 82 0.47 512 10000 83 0.92 904 84 1.64 1460 85 2.40 1990 87 6.95 5270 5000 88 9.93 7300 89 11.30 8110 90 13.20 9280 92 17.40 11800 0 95 22.80 14900 50 320 100 1.58 1520 101 2.42 2260 102 3.36 3040 103 3.90 3430 105 5.52 4620 106 6.42 5260 107 8.80 7050 108 12.80 10000 109 15.00 11600 110 22.10 16700 1: Calculated from M. Source: Wagner, K.-D.; Dahmen, N.; Dinjus, E., J. Chem. Eng. Data (2000), 45(4), 672-677.

CAT4240—CHAPTER 20—1/11/2006—19:16—SRAM—XML MODEL C – pp. 735–808

75

100 P (bar)

125

Solubility Data T

805

Tris(p -trifluoromethylphenyl)phosphine (C21H12F9P; MW=466.29)

310

320

60 61 63 64 65 67 68 82 83 84 85 86 87 88 89 90 91 92 93 73 80 85 87 90 92 94 97 98 99 102 104 106 108 110 105 106 107 110 112 113

M x 10 (mol/L)

0.20 0.30 1.10 1.30 1.60 9.30 47.00 0.10 0.25 0.92 1.76 4.66 5.57 9.40 11.70 16.00 19.90 27.10 41.40 1.57 1.93 2.22 2.67 2.85 2.93 3.42 3.60 3.60 4.20 4.40 4.40 4.60 4.60 5.30 2.50 3.50 3.50 7.60 9.60 11.70

[T-101]

y1) x 106 480 690 2330 2620 3050 15200 29100 110 250 820 1460 3670 4220 6910 8390 11200 13700 18310 27400 3570 3610 3590 4060 3930 3760 4080 3840 3710 4170 3980 3770 3770 3630 4060 2100 2870 2820 5800 7130 8570

300 K 310 K 320 K

30000

6

300

P (bar)

y x 10

T (K)

2

20000

10000

0 50

CAT4240—CHAPTER 20—1/11/2006—19:16—SRAM—XML MODEL C – pp. 735–808

75

100 P (bar)

125

806

Solubility in Supercritical Carbon Dioxide

113 114 115 116 117 119 120

12.10 13.80 16.20 18.60 24.40 30.70 35.10

8860 9980 11600 13100 17000 21000 23700

1: Calculated from M. Source: Wagner, K.-D.; Dahmen, N.; Dinjus, E., J. Chem. Eng. Data (2000), 45(4), 672-677.

Tristearin (C57H110O6; MW=891.48)

333.15

S (g/L)

81.1 101.3 152.0 202.7 101.3 121.6 152.0 202.7 253.3

0.000 0.013 0.110 0.190 0.000 0.002 0.042 0.210 0.490

y x 10

0.00 1.00 6.90 11.10 0.00 0.22 3.37 14.20 30.60

1: Calculated from S. Synonyms: Glycerin tristearate; Glycerol trioctadecanoate Source: Chrastil, J. J. Phys. Chem. (1982), 86(15), 3016-3021.

313.15 K 333.15 K

30 6

313.15

P (bar)

[T-102] 6

y x 10

T (K)

1)

20 10 0 50

Tritriacontane (C33H68; MW=464.89) T (K)

P (bar)

308.2

100 120 140 160 180 200 240

1)

y x 10

6

10.0 14.0 16.0 23.0 24.0 27.0 34.0

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100

150

200

250

P (bar)

[T-103]

Solubility Data T

333.2

3.2 29.0 48.0 72.0 93.0 120.0 150.0 0.5 18.0 77.0 160.0 240.0 320.0 440.0 0.5 11.0 95.0 200.0 350.0 550.0 800.0

900 308.2 K 318.2 K 328.2 K 333.2 K

600 6

328.2

100 120 140 160 180 200 240 100 120 140 160 180 200 240 100 120 140 160 180 200 240

y x 10

318.2

807

300

0 50

100

150

200

250

P (bar)

1: All the data at 100 bar, all the data at 120 bar except for the one at 308.2 K, and the data at 140 bar and 333.2 K (the data in Italics) are the extrapolated values in the original article. Source: Chandler, K.; Pouillot, F. L. L.; Eckert, C. A. J. Chem. Eng. Data (1996), 41, 6-10.

Troeger’s Base (C17H18N2; MW=250.34)

318

328

y x 106 151.0 304.0 501.0 625.0 708.0 45.4 135.0 413.0 551.0 644.0 31.3 48.8 277.0 564.0 800.0

308 K 318 K 328 K

800 600 6

P (bar) 80 100 130 160 190 80 100 130 160 190 80 100 130 160 190

y x 10

T (K) 308

[T-104]

400 200 0 50

Synonym: 2,8-Dimethyl-6H,12H-5,11methanodibenzo[b,f ][1,5]diazocine Source: Ren, Q.; Su, B.; Huang, M. ; Wu, P. J. Chem. Eng. Data (2000), 45(3), 464-466.

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100

150 P (bar)

200

808

Solubility in Supercritical Carbon Dioxide

L -Tryptophan (C11H12N2O2; 1)

1)

2)

T (K) P (bar) S (μg/Nl )

MW=204.23) 3)

y x 10

[T-105]

6

0.06

500 0.297 0.0324 1000 0.398 0.0434 1500 0.455 0.0496 2000 0.450 0.0491 1: Obtained by digitizing the graph in the original article. 2: "Nl" means "Normliter," which is one liter at 273.15 K and 1 atm. 3: Calculated from S. Synonym: (2S)-2-Amino-3-(1H-indol-3-yl) propanoic acid Source: Stahl, E.; Schilz, W. Chem. Ing. Tech. (1978), 50(7), 535-537.

y x 10

6

313.15

0.04

0.02 0

1000

2000

P (bar)

Turmeric1) oil

313 323 333

200 300 400 300 300 300

3.34 7.60 12.60 10.00 5.03 1.93

3330 7540 12400 9900 5000 1930

1: A South Asian herb, Curcuma longa. 2: Obtained by digitizing the graph in the original article. 3: Calculated from W. Source: Gopalan, B.; Goto, M.; Kodama, A.; Hirose, T. Agric. Food Chem. (2000), 48(6), 2189-2192.

14000 6

w3) x 106

w x 10

W (g/kg CO2)

7000 0 100

200

300

400

500

P (bar) 12000 6

313

P (bar)

w x 10

T (K)

[T-106] 2)

6000 0 310

320

330 T (K)

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340

21

Solubility Data U

1-Undecanol (C11H24O; MW=172.31)

[U-1]

y x 106

80000 y x 106

T (K) P (bar) 323.15 95.1 3216 106.4 4114 114.2 6715 131.4 10400 150.2 15040 169.6 30740 187.8 41170 202.2 49860 213.1 55100 233.3 64000 238.5 62120 Synonym: Undecyl alcohol Source: Artal, M. ; Pauchon, V. ; Embid, J. M.; Jose, J. J. Chem. Eng. Data (1998), 43(6), 983-985.

40000

0

0

100 200 P (bar)

Undecanolide (C11H20O2; MW=184.28) yx

[U-2]

106

1660 2310 3410 3940 4360 2710 3190 4800 5900 6630 Synonyms: Oxacyclododecan-2-one; 11-Undecanolactone Source: Mishima, K.; Matsuyama, K.; Baba, M.; Hirabaru, T.; Yamauchi, S.; Tomokage, H.; Takahashi, K.; Yamasaki, N. J. Chem. Eng. Data (2001), 46(1), 69-72.

8000 308.2 K 318.2 K

y x 106

T (K) P (bar) 91 308.2 101 152 203 253 318.2 91 101 151 203 253

300

4000

0 50

150 P (bar)

250

809

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810

Solubility in Supercritical Carbon Dioxide

Uracil (C4H4N2O2; MW=112.09)

[U-3]

106

P (bar)

150

y x 106

Mx y x 106 (mol/L) 313.25 100.0 42 2.9 313.15 125.0 49 2.9 313.35 150.0 150 8.4 313.25 200.0 230 12.0 313.25 249.9 400 20.0 313.15 299.8 740 36.0 333.25 100.0 15 2.3 333.15 125.0 27 2.5 333.15 150.0 75 5.5 333.35 200.1 440 27.0 333.25 250.0 1000 58.0 333.15 299.9 2400 130.0 Synonym: 2,4-Pyrimidinedione Source: Burgos-Solorzano, G. I.; Brennecke, J. F. ; Stadtherr, M. A. Fluid Phase Equil. (2004), 220(1), 57-69. T (K)

100

313 K 333 K

50 0 50

150

250

Uranyl bis(thenoyltrifluoroacetonate) · Phosphate (X) Complex1) (UO2(C8H4F3O2S)2·X;

350

P (bar)

[U-4]

FW=736.402))

M3) x 106 y4) x 106 (mol/L) X = TBP (C12H27O4P; MW=266.31)

T (K) P3) (bar)

313.15

152 178 204 227 253 279 302 330

1100 2500 3300 4000 4700 5200 5400 5800

62 134 172 204 234 254 260 275

TBP TEP TOPO

600 y x106

126 1100 66 152 3400 191 178 5700 306 204 7300 380 227 8600 438 251 10100 504 279 11900 582 302 14600 704 328 16600 789 X = TEP (C6H15O4P; MW=182.15)

900

313.15

300

0 100

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200 P (bar)

300

Solubility Data U

811

X = TOPO (C24H51OP; MW=386.63) 313.15

178 500 27 204 1400 73 227 2400 122 253 3145 157 279 3270 160 302 3899 188 330 4277 203 TBP: Tributyl phosphate TEP: Triethyl phosphate TOPO: Trioctylphosphine oxide 1: UO2 forms a complex with thenoyltrifluoroacetone (H(tta)) and an alkyl phosphate (X). 2: The molecular weight of alkyl phosphate (X) is not included in this formula weight. 3: Obtained by digitizing the graph in the original article. May have large reading errors as the source graph is small. 4: Calculated from M. Source: Wai, C. M.; Waller, B. Ind. Eng. Chem. Res. (2000), 39(12), 4837-4841.

Uranyl bis(trifluoroacetylacetonate) · Pyridine Complex1) (UO2(C5H4F3O2)2·C5H5N; FW=655.29) Additive Amount of S2) (excess Additive y3) x 106 (g U/L) ligand) (mL) 0.000 333.15 303.98 None 0.45 100 4) 0.002 H(tfa) 0.79 175 Pyridine 0.95 210 0.002 1: Uranium was extracted as an adduct of uranyl trifluoroacetylacetonate and pyridine. 2. Solubility is based on grams of uranium per liter. 3: Calculated from S. 4: H(tfa) is trifluoroacetylacetone. Source: Murzin, A. A.; Babain, V. A.; Shadrin, A. Yu.; Smirnov, I. V.; Lumpov, A. A.; Gorshkov, N. I.; Miroslavov, A. E.; Muradymov, M. Z. Radiochem. (2001), 43(2), 177-182. T (K)

P (bar)

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[U-5]

812

Solubility in Supercritical Carbon Dioxide

Uranyl dinitrate · Tributyl phosphate Complex1) (UO2(NO3)2·2(C12H27O4P); FW=926.67) T (K) P2) (bar)

S2) x 106 (g/L)

y3)x 106

[U-6]

800

0.001 0.2 90 0.014 2.0 95 0.15 16.8 103 400 105 1.1 113.4 109 4.5 425.7 116 7.9 663.6 0 124 8.5 659.6 80 137 10.0 712.7 145 10.0 688.0 155 10.0 664.7 1: UO2 forms a complex with nitric acid and tributylphosphate. 2: Obtained by digitizing the graph in the original article. As the authors used only 10 μg of uranyl complex, the solubility appeared nearly constant at pressures above 130 bar. Actual solubility may be higher than those shown here at above 30 bar. 3: Calculated from S. Source: Addleman. R. S.; Carrott. M. J. ; Wai. C. M. Anal. Chem. (2000), 72(17), 4015-4021.

y x 106

323.15

120 P (bar)

160

Uranyl dinitrate · Tributyl phosphate complex1) (UO2(NO3)2 ·2(C12H27O4P); FW=926.67)

313

323

101 126 152 177 182 188 192 203 228 152 177 183 192 203 213 223 233 243 254

M2) (mol/L) 0.003 0.023 0.061 0.170 0.160 0.180 0.450 0.430 0.430 0.023 0.048 0.053 0.071 0.088 0.120 0.148 0.160 0.259 0.286

y3) x 106 210 1400 3400 9100 8500 9500 23000 22000 21000 1400 2800 3000 4000 4900 6500 8100 8500 13600 14800

25000

313 K 323 K 333 K

20000 y x 106

T (K) P2) (bar)

[U-7]

15000 10000 5000

0

50

150

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P (bar)

250

350

Solubility Data U

813

210 152 0.003 640 177 0.010 1800 203 0.030 3900 228 0.068 5400 254 0.098 14000 279 0.260 304 0.290 15000 1: UO2 forms a complex with nitric acid and tributylphosphate(TBP). 2: Obtained by digitizing the graph in the original article. 3. Calculated from M. Source: Carrott, M. J. ; Waller, B. E. ; Smart, N. G. ; Wai, C. M. Chem. Comm. (1998), (3), 373-374. 333

Uranyl thenoyltrifluoroacetylacetonate · Tributyl phosphate complex1) (UO2(C10H6F3O3S)2·2(C12H27O4P); FW=1329.09)

y x 106

T (K) P2) (bar) M2) x 106 y3) x 106 313.15 101 190 13 800 144 1150 65 188 3450 183 231 5630 286 400 273 7280 357 315 8500 407 0 357 10200 475 0 400 12100 554 441 14800 670 485 16900 750 1: UO2 forms a complex with thenoyltrifluoroacetyl acetone(tta) and tributylphosphate(TBP). 2: Obtained by digitizing the graph in the original article. 3: Calculated from M. Source: Carrott, M. J.; Wai, C. M. Anal. Chem. (1998), 70(11), 2421-2425.

[U-8]

200 400 P (bar)

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600

22

Solubility Data V

[V-1]

Vanillic acid (C8H8O4; MW=168.15) y x 106 P (bar) 85 1.43 100 3.55 150 8.52 200 11.47 250 15.13 60 300 16.75 350 18.34 400 22.63 450 24.39 500 26.00 40 323 100 1.69 150 8.57 200 15.71 250 20.49 20 300 25.45 350 29.65 400 34.63 450 36.38 0 500 38.92 0 333 100 0.94 150 8.67 200 19.39 250 26.49 300 33.86 350 39.16 400 47.42 450 55.54 500 60.71 Synonym: 4-Hydroxy-3-methoxybenzoic acid Source: Murga, R.; Sanz, M.- T.; Beltran, S.; Cabezas, J.- L. J. Chem. Eng. Data (2004), 49(4), 779-782. T (K) 313

y × 106

313 K 323 K 333 K

200

400

600

P (bar)

815

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816

Solubility in Supercritical Carbon Dioxide

Vanillic acid (C8H8O4; MW=168.15) 313

328

P (bar) 86 90 120 140 160 200 250 90 120 140 160 200 250

y x 10

30

2.03 6.48 8.54 9.58 9.91 11.60 14.00 0.48 2.97 8.01 12.30 17.00 23.90

313 K 328 K

y × 106

T (K)

[V-2]

6

20

10

0 50

150 P (bar)

250

Synonym: 4-Hydroxy-3-methoxybenzoic acid Source: Stassi, A.; Bettini, R.; Gazzaniga, A.; Giordano, F.; Schiraldi, A. J. Chem. Eng. Data (2000), 45(2), 161-165.

Vanillin1) (C8H8O3; MW=152.15) P (bar) y2) x 106 83 380 87 700 90 740 92 1000 98 1130 109 1390 110 1480 120 1540 132 1760 136 1890 151 2180 157 2270 161 2320 164 2410 172 2420 180 2590 185 2610 190 2790

4000 308.2 K

3000 y × 106

T (K) 308.2

[V-3]

318.2 K

2000

1000

0 50

100

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150 P (bar)

200

Solubility Data V

817

318.2

98 430 104 620 113 1210 115 1310 120 1470 125 1750 131 1970 135 2030 145 2350 155 2510 163 2570 170 2820 178 2970 185 3180 195 3530 1: Referred to as vanillan in the source. 2: The solubility unit "mole fraction" in the source table was misprinted and thus was corrected it to "mol%" based on Figure 4 in the same article. Synonym: 4-Hydroxy-3-methoxybenzaldehyde Source: Wells, P. A.; Chaplin, R. P.; Foster, N. R. J. Supercrit. Fluids (1990), 3(1), 8-14.

Vegetable oil from Buriti fruit1) T (K)

P (bar)

W (g/kg CO2)

[V-4]

w2) x 106

8000

w × 106

200 2.8 2790 200 2.9 2890 300 6.8 6750 300 6.5 6460 300 6.2 6160 300 7.0 6950 328 200 1.7 1700 200 1.5 1500 200 1.8 1800 300 6.0 5960 300 6.1 6060 1: Buriti (Mauritia flexuosa) is a fruit from plam tree that grows in Amazon region (Brazil). 2. Calculated from W. Source: De Franca, L. F.; Reber, G.; Meireles, M. A. A.; Machado, N. T.; Brunner, G. J. Supercrit. Fluids (1999), 14(3), 247-256.

313 K 328 K

313

4000

0 150

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250 P (bar)

350

818

Solubility in Supercritical Carbon Dioxide

cis-Verbenol (C10H16O; MW=152.23) y x 10 60 50 140 130 260 210 230 650 630 1150 1130 1390 1180 1140 2570 3120 3620 4420 5630 20620 20250 27300 29600 52300 53000 140 130 180 160 200 420 410 650 680 1110 1040 700 530 1070 960 2010 1990 2630 2720

60000 313.15 K 323.15 K 328.15 K

40000 y × 106

T (K) P (bar) 313.15 51.9 51.1 60.7 60.8 69.4 70.1 70.6 75.7 75.8 81.2 81.5 82.7 82.8 83.1 83.9 84.0 85.6 85.8 86.3 90.7 91.0 98.5 99.1 107.1 109.4 323.15 51.4 51.6 61.3 61.3 63.0 71.7 71.7 77.1 77.2 80.8 80.8 84.6 85.4 88.6 89.2 93.6 94.6 94.9 97.5

[V-5]

6

20000

0 50

CAT4240—CHAPTER 22—31/10/2006—19:40—KADAMBADI—XML MODEL C – pp. 815–823

100 P (bar)

150

Solubility Data V

819

103.3 4080 5390 103.7 105.4 10750 106.0 11640 108.7 12460 109.4 12640 118.4 30900 128.4 47200 129.8 46400 328.15 51.6 120 62.0 260 62.2 170 73.8 440 74.3 430 82.8 750 82.8 840 88.9 900 88.9 940 96.9 1080 97.1 1020 97.6 1720 107.1 4640 107.7 5350 112.5 10520 120.6 12550 122.1 13270 131.0 28600 135.2 35200 137.8 38500 Synonym: cis-2-Pinen-4-ol Source: Richter, M.; Sovova, H. Fluid Phase Equil. (1993), 85, 285-300.

[V-6]

Vitamin A Palmitate (C36H60O2, MW=524.87)

333

P(bar)

W (g/kg CO2)

1000

y x 106

125 0.24 20 150 0.93 78 200 3.19 267 250 6.20 520 275 8.52 714 300 10.47 877 Synonyms: Retinol hexadecanoate; alltrans-Retinol palmitate Source: Catchpole, O. J.; Grey, J. B.; Noermark, K. A. J. Chem. Eng. Data (1998), 43(6), 1091-1095.

y × 106

T (K)

500

0 100

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200 P (bar)

300

820

Solubility in Supercritical Carbon Dioxide

[V-7]

Vitamin D2 (C28H44O; MW=396.65)

333

353

P (bar) W (g/kg) 200 3.2 220 3.4 240 3.8 260 4.2 280 4.0 300 4.3 320 4.6 200 2.7 220 3.3 240 4.3 260 5.2 280 5.7 300 6.3 200 2.6 220 4.9 240 5.8 250 6.9 260 7.4 280 9.3

y × 106 350 380 420 460 450 480 510 300 370 480 580 640 700 290 540 640 770 830 1040

1100 313 K 333 K 353 K

800 y × 106

T (K) 313

500

200 150

250

350

P (bar)

Synonyms: Calciferol; Ergocalciferol Source: Johannsen, M.; Brunner, G. J. Chem. Eng. Data (1997), 42(1), 106-111.

[V-8]

Vitamin D2 (C28H44O; MW=396.65)

303

313

P (bar)

W (g/kg CO2)

79.8 82.5 90.8 121.8 141.5 182.5 235.5 265.0 287.5 293.0 83.0 102.5 124.8 158.8 186.3 219.5 251.0 255.0 273.5 299.5 302.5

0.48 0.53 0.64 1.14 1.27 2.19 2.03 1.83 2.00 2.22 0.75 0.85 1.03 1.21 1.16 1.50 2.16 1.98 2.24 4.21 4.66

y x 106 53 58 71 126 141 242 225 203 221 246 83 94 114 134 129 167 240 220 248 466 516

1500 303 K 313 K 333 K 353 K

1000 y x 106

T (K)

50

0 50

150

CAT4240—CHAPTER 22—31/10/2006—19:40—KADAMBADI—XML MODEL C – pp. 815–823

250 P (bar)

350

Solubility Data V

821

1.56 84.0 173 6.75 102.0 748 7.45 128.0 825 8.52 129.0 944 11.96 130.0 1325 10.61 131.0 1176 8.23 133.0 912 8.56 155.3 949 6.52 183.0 723 5.24 223.8 581 4.77 255.0 529 2.10 289.0 233 0.38 353 110.5 43 1.70 137.5 189 2.48 160.0 276 2.09 187.0 232 2.75 212.3 305 1.41 250.3 156 281.5 109 0.98 Synonyms: Calciferol; Ergocalciferol Source: Knez, Z.; Skerget, M. J. Supercrit. Fluids (2001), 20(2), 131-144. 333

Vitamin D3 (C27H44O; MW=384.64) 6

6000 313 K 333 K 353 K

4000 y x 106

P (bar) W (g/kg) y x 10 200 5.0 570 220 5.2 600 240 5.0 570 260 5.5 640 280 6.3 720 300 6.4 730 350 6.9 790 333 200 4.0 460 220 5.1 580 240 5.8 670 260 7.3 840 280 9.0 1040 300 11.8 1360 320 26.4 3090 350 43.8 5210 353 200 4.0 460 220 4.1 470 240 5.9 680 260 6.4 730 280 6.9 790 300 9.3 1080 320 11.7 1360 350 25.0 2920 Synonym: Cholecalciferol Source: Johannsen, M.; Brunner, G. J. Chem. Eng. Data (1997), 42(1), 106-111. T (K) 313

[V-9]

2000

0 150

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250 P (bar)

350

822

Solubility in Supercritical Carbon Dioxide

Vitamin D3 (C27H44O; MW=384.64) P(bar)

W (g/kg CO2)

y × 106

313

151.0 3.02 321 203.5 2.52 288 244.0 3.94 451 297.5 4.61 527 333 99.5 4.19 479 152.0 4.00 457 203.5 4.27 489 254.5 4.33 495 298.0 9.31 1083 353 97.5 2.06 235 151.5 2.23 255 201.0 4.02 401 249.0 6.82 779 293.5 12.67 1447 Synonym: Cholecalciferol Source: Knez, Z.; Skerget, M. J. Supercrit. Fluids (2001), 20(2), 131-144.

1600 313 K 333 K 353 K

1200 y × 106

T(K)

[V-10]

800 400 0 50

150

250 P (bar)

Vitamin K1 (C31H46O2; MW=450.70) P (bar) W (g/kg) y × 106 200 13.4 1320 220 15.2 1510 240 17.0 1690 260 20.0 1990 280 22.4 2230 300 27.8 2780 320 32.3 3250 350 35.3 3560 333 200 7.2 710 220 11.2 1110 240 15.3 1510 260 17.2 1700 280 20.5 2040 300 22.6 2250 320 28.1 2810 350 34.8 3510 353 200 3.0 290 220 5.7 560 240 9.1 890 260 11.6 1140 280 16.4 1620 300 20.1 2000 320 24.8 2480 350 29.8 2990 Synonyms: Phylloquinone; Phytomenadione Source: Johannsen, M.; Brunner, G. J. Chem. Eng. Data (1997), 42(1), 106-111.

350

[V-11]

T (K) 313

4000

y × 106

3000

313 K 333 K 353 K

2000

1000

0 150

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250 P (bar)

350

Solubility Data V

823

Vitamin K3 (C11H8O2; MW=172.18) P (bar) W (g/kg) y × 106 220 23.6 6140 240 23.9 6210 260 23.0 5990 280 25.6 6680 300 23.5 6120 320 23.3 6070 Synonyms: Menadione; 2-Methyl-1,4naphthoquinone Source: Johannsen, M.; Brunner, G. J. Chem. Eng. Data (1997), 42(1), 106-111.

[V-12]

T (K) 313

y × 106

7000 6000 5000 200

250

P (bar)

300

Vitamin K3 (C11H8O2; MW=172.18) T (K)

P (bar)

W (g/kg CO2)

350

[V-13]

y × 106

82.0 1.824 466 4500 94.5 4.514 1152 152.0 8.105 2067 197.5 13.439 3423 253.0 15.984 4068 307.0 14.962 3809 3000 333 81.5 9.575 2440 95.0 13.479 3430 108.3 12.631 3220 111.5 11.939 3040 149.0 6.351 1620 1500 196.5 12.241 3120 209.5 13.263 3380 245.0 12.374 3150 303.0 12.841 3270 0 353 81.5 0.617 158 50 123.5 1.896 484 155.5 2.898 740 202.5 5.969 1523 247.5 8.001 2040 299.0 10.547 2688 Synonyms: Menadione; 2-Methyl-1,4-naphthoquinone Source: Knez, Z.; Skerget, M. J. Supercrit. Fluids (2001), 20(2), 131-144.

y × 106

313

313 K 333 K 353 K

150 250 P (bar)

CAT4240—CHAPTER 22—31/10/2006—19:40—KADAMBADI—XML MODEL C – pp. 815–823

350

23

Solubility Data W

Water (H2O; MW=18.02) P (bar) y x 106 40.5 4600 50.6 3600 60.6 3700 70.8 3400 80.8 3400 90.9 4100 100.9 4500 111.0 5000 121.0 5500 141.1 6100 333.2 40.5 6600 50.6 5500 60.6 5500 70.8 5100 80.8 5000 90.9 4700 100.9 4900 111.0 5300 121.0 5800 141.1 7800 353.1 40.5 14300 60.6 10900 70.8 10400 80.8 9700 90.9 9200 100.9 9300 111.0 9000 121.0 9600 131.0 10000 Source: Bamberger, A.; Sieder, G.; Maurer, G. J. Supercrit. Fluids (2000), 17(2), 97-110.

[W-1]

T (K) 323.2

15000

323.2 K 333.2 K 353.1 K

y x 106

10000

5000

0 0

50

100

150

P (bar)

.

825

CAT4240—CHAPTER 23—31/10/2006—19:38—MUGUNTHAN—XML MODEL C – pp. 825–828

826

Solubility in Supercritical Carbon Dioxide

Water (H2O; MW=18.02) T (K)

P (bar)

[W-2]

S (g/L)

1)

6

y x 10

y x 106

101.325 0.75 4480 151.988 1.79 6140 253.313 2.40 6940 353.15 101.325 0.65 6920 151.988 1.80 9910 202.650 3.02 12080 253.313 3.74 13010 1: Calculated from S. Source: Chrastil, J. J. Phys. Chem. (1982), 86(15), 3016-3021.

14000

323.15

323.15 K 353.15 K

9000

4000 50

150

250

P (bar)

[W-3]

Water (H2O; MW=18.02)

298.2

308.2

y x 10

2220 2350 2410 2550 2620 2720 2800 2610 2720 2760 2780 2930 2870 3070 3200 3220 3340 3000 3070 3090 3140 3270 3370 3410 3440 3540 3690 3780 3840 4070 4140 4350 4400

6000

288.2 K 293.2 K 298.2 K 308.2 K 313.2 K

6

293.2

P (bar) 51.7 76.0 101.3 126.7 152.0 177.3 202.7 58.8 70.9 76.0 81.1 101.3 126.7 141.9 152.0 177.3 202.7 65.9 70.9 76.0 91.2 101.3 111.5 126.7 141.9 152.0 177.3 202.7 91.2 101.3 111.5 126.7 136.8

y x 10

T (K) 288.2

6

4000

2000 50

100

CAT4240—CHAPTER 23—31/10/2006—19:38—MUGUNTHAN—XML MODEL C – pp. 825–828

150 P (bar)

200

Solubility Data W

827

152.0 202.7 101.3 111.5 126.7 152.0 177.3 202.7

313.2

4570 4980 4280 4400 4670 5070 5430 5800

Source: King, M. B.; Mubarak, A. J.; Kim, J. D.; Bott, T. R. J. Supercrit. Fluids (1992), 5(4), 296-302.

[W-4]

Water (H2O; MW=18.02) (bar)

y1)

x

106

101 4000 102 4200 103 4400 200 5700 201 5800 202 5600 323 150 6200 151 6400 152 5800 200 6600 202 6900 1: Obtained by digitizing the graph in the original article. Source: Leeke, G.; Gaspar, F.; Santos, R. Ind. Eng. Chem. Res. (2002), 41(8), 2033-2039.

7000 y x 106

T (K) 313

P1)

313 K 323 K

5000

3000 100

150

200

P (bar)

Wax1) T (K)

[W-5] P (bar)

S (g/L)

w2)

x

106

w x 106

138 0.27 340 253 0.36 400 379 0.60 620 328.15 138 0.24 390 253 0.51 630 379 1.09 1210 343.15 138 0.21 470 253 0.58 780 379 1.37 1620 1: An ingredient of propellants whose molecular weight and molecular weight distribution are not known. 2: Calculated from S. Source: Ashraf-Khorassani, M.; Taylor, L. T. J. Chem. Eng. Data (1999), 44(6), 1254-1258.

2000

308.15

308 K 328 K 343 K

1000

0 100

200

CAT4240—CHAPTER 23—31/10/2006—19:38—MUGUNTHAN—XML MODEL C – pp. 825–828

300 P (bar)

400

828

Solubility in Supercritical Carbon Dioxide

Wool wax

305.15 K 318.15 K 333.15 K 358.15 K 423.15 K

w x 10

6

P1) (bar) w1) x 106 305.15 253.3 3720 354.6 4710 456.0 4960 557.3 4710 45000 658.6 3970 318.15 253.3 2730 354.6 5700 456.0 7440 30000 557.3 8430 658.6 7440 333.15 253.3 2730 354.6 5460 456.0 9670 15000 557.3 10200 658.6 10900 358.15 253.3 1980 354.6 5700 0 456.0 9670 200 557.3 13400 658.6 18100 423.15 253.3 2230 354.6 6200 456.0 14100 557.3 25000 658.6 44400 1: Obtained by digitizing the graph in the original article. Source: Jones, F. W.; Bateup, B. O.; Dixon, D. R.; Gray, S. R. J. Supercrit. Fluids (1997), 10(2), 105-111.

[W-6]

T (K)

CAT4240—CHAPTER 23—31/10/2006—19:38—MUGUNTHAN—XML MODEL C – pp. 825–828

400 P (bar)

600

24

Solubility Data X

2,5-Xylenol (C8H10O; MW=122.16) T (K) 308.15

P (bar)

yx

[X-1]

106

14000 y x 106

74 365 87 4880 107 7370 134 8570 164 9800 207 10700 237 11300 267 11600 Synonym: 2,5-Dimethylphenol Source: Iwai, Y.; Yamamoto, H.; Tanaka, Y.; Arai, Y. J. Chem. Eng. Data (1990), 35(2), 174-176.

7000

0 50

150 P (bar)

[X-2]

2,6-Xylenol (C8H10O; MW=122.16) 6

350000 y x 106

1)

P (bar) y x 10 T (K) 308.15 103 310000 207 271000 1: Coexisting liquid phase may be present. Synonym: 2,6-Dimethylphenol Source: Iwai, Y.; Yamamoto, H.; Tanaka, Y.; Arai, Y. J. Chem. Eng. Data (1990), 35(2), 174-176.

250

300000 250000 50

150

250

P (bar)

.

829

CAT4240—CHAPTER 24—31/10/2006—19:42—KADAMBADI—XML MODEL C – pp. 829–830

830

Solubility in Supercritical Carbon Dioxide

[X-3]

3,4-Xylenol (C8H10O; MW=122.16) 106

T (K) 313.15

5000 0 50

150

[X-4]

(C5H10O5; MW=150.13) S1) P1) (bar) ( μg/Nl 2)) y3) x 106

296 1.076 0.160 500 1.455 0.216 1000 2.091 0.310 1491 2.773 0.411 1988 2.939 0.436 1: Obtained by digitizing the graph in the original article. 2: "Nl" means "Normliter," which is one liter at 273.15 K and 1 atm. 3: Calculated from S. Synonym: (+)-Xylose Source: Stahl, E.; Schilz, W. Chem. Ing. Tech. (1978), 50(7), 535-537.

250

P (bar)

0.5 y x 106

D -Xylose

10000 y x 106

yx P (bar) 82 2340 112 5120 163 7190 185 7680 204 8190 233 8650 262 9100 Synonyms: 3,4-Dimethylphenol; 4-Hydroxy-1,2-dimethylbenzene Source: Mori, Y.; Shimizu, T.; Iwai, Y.; Arai, Y. J. Chem. Eng. Data (1992), 37(3), 317-19. T (K) 308.15

0.3

0.1 0

CAT4240—CHAPTER 24—31/10/2006—19:42—KADAMBADI—XML MODEL C – pp. 829–830

1000 P (bar)

2000

25

Solubiliy Data Y

[ Y-1]

Yttrium tris(acetylacetonate) (C15H21O6Y; FW=386.23) T (K)

P (bar)

6

y x 10

y x 106

120 16.5 170 18.0 220 34.0 443.15 120 4.7 170 10.5 220 27.5 Synonyms: Tris(2,4-pentanedionato)yttrium; Tris(acetylacetonato)yttrium Source: M'Hamdi, R.; Bocquet, J.; Chhor, K.; Pommier, C. J. Supercrit. Fluids (1992), 5(1), 55-59.

40

423.15

423 K 443 K

20

0 100

150

200 P (bar)

[ Y-2]

Yttrium tris(hexafluoroacetylacetonate) (C15H3F18O6Y; FW=746.09)

443.15

P (bar) 120 170 220 120 170 220

6

y x 10

725 835 930 310 420 800

Synonyms: Tris(1,1,1,5,5,5-hexafluoro2,4-pentanedionato)yttrium; Yttrium(III) hexafluoroacetylacetonate Source: M'Hamdi, R.; Bocquet, J.; Chhor, K.; Pommier, C. J. Supercrit. Fluids (1992), 5(1), 55-59.

1200

y x 106

T (K) 423.15

250

600

0 100

423 K 443 K

150

200

250

P (bar)

831

CAT4240—CHAPTER 25—31/10/2006—19:43—MUGUNTHAN—XML MODEL C – pp. 831

26

Solubility Data Z [Z-1]

Zinc bis(acetylacetonate) (C10H14O4Zn; FW=263.60) 1)

2)

106

P (bar) S (mg/L) y x T (K) 333 98 0.091 0.054 196 0.754 0.175 294 0.947 0.191 1: Obtained by digitizing the graph in the original article. 2. Calculated from S. Synonym: Bis(2,4-pentanedionato)zinc; Zinc bis(2,4-pentanedionate) Source: Saito, N.; Ikushima, Y.; Goto, T. Bull. Chem. Soc. Japan (1990), 63(5), 1532-1534.

0.2 y x 106

1)

0.1 0 150

50

250 P (bar)

[Z-2]

Zinc dithiocarbamate complexes P (bar)

6

y x 10

Zinc bis(trifluoroethyl)dithiocarbamate (BDC) 333 101 950 233 9000 Zinc diethyldithiocarbamate (DDC1) 333 101 1.1 233 24.0 Zinc dipropyldithiocarbamate (DDC2) 333 101 7.9 233 150 Zinc dibutyldithiocarbamate (DDC3) 333 101 82 233 690 Zinc dipentyldithiocarbamate (DDC4) 333 101 160 233 3200 Zinc dihexyldithiocarbamate (DDC5) 333 101 320 233 5800 Zinc pyrrolidinedithiocarbamate (PDC) 333 101 0.32 233 9.00

10000

BDC DDC1 DDC2 DDC3 DDC4 DDC5 PDC

7500 y x 106

T (K)

350

5000

2500

0 0

100

200

300

P (bar)

Source: Wai, C. M.; Wang, S.; Yu, J.-J. Anal. Chem. (1996), 68(19), 3516-3519.

833

CAT4240—CHAPTER 26—31/10/2006—19:47—KADAMBADI—XML MODEL C – pp. 833–834

834

Solubility in Supercritical Carbon Dioxide

[Z-3]

Zopiclone (C17H17ClN6O3; MW=388.81) T (K)

P (bar)

S×103 (g/L)

y × 106

313

25 313 K 323 K 333 K

6

20

y x 10

100 19.0 3.4 125 39.6 6.1 150 58.7 8.5 175 69.2 9.6 200 85.4 11.5 225 89.1 11.7 250 97.9 12.6 323 100 7.0 2.0 125 31.8 5.8 150 59.6 9.6 175 79.5 12.0 200 98.4 14.2 225 112.0 15.6 250 124.6 16.9 333 100 3.9 1.5 125 27.4 6.3 150 58.6 10.9 175 88.8 14.8 200 116.2 18.1 225 134.0 20.0 250 152.3 21.9 Synonym: 1-Piperazinecarboxylic acid, 4-methyl-6(5-chloro-2-pyridinyl)-6,7-dihydro-7-oxo-5Hpyrrolo[3,4-b]pyrazin-5-yl ester Source: Medina, I.; Bueno, J. L. J. Chem. Eng. Data (2001), 46(5), 1211-1214.

15 10 5 0 50

100

.

CAT4240—CHAPTER 26—31/10/2006—19:47—KADAMBADI—XML MODEL C – pp. 833–834

150

200

P (bar)

250

Appendix A Density Data of Carbon Dioxide

K

8 31

.1

5

. 13

15

K

30

3

K

15 K 30 8 K 29 3.1 8.1 5 5K K 293 .15 K 288.1 5K 283.15 K

100

5K

3.1

32

8.

15

243.15 K

263.15 K

50

273.15 K

30

Pressure (bar)

3

. 33

12

150

4.

1073.1 873.15 5 K 773.15 KK 673.1 573.155 K 523.15 K 473.15 K K 423. 15 K 393 .15 373 K 36 .15 3 .15 K 35 3.1 K 5K 34 3. 15 K

200

0 0

5

10

15

20

25

Density (mol/L)

FIGURE A.1 Density variation of carbon dioxide with temperature and pressure. The bold line shows the saturated liquid line (left) and the saturated vapor line (right). The dashed line represents the density at the critical temperature, i.e., 30.9788C (304.128 K).

835

CAT4240—Appendix A—2/11/2006—19:47—SRIDHAR—15608—XML MODEL C – pp. 835–854

836

Solubility in Supercritical Carbon Dioxide

TABLE A.1 Density of Saturated Carbon Dioxide versus Temperaturea Density (mol/L) T (8C)

T (K)

P (bar)

Sat’d Liq.

Sat’d Vap.

K56.558 K56 K55 K54 K53 K52 K51 K50 K49 K48 K47 K46 K45 K44 K43 K42 K41 K40 K39 K38 K37 K36 K35 K34 K33 K32 K31 K30 K29 K28 K27 K26 K25 K24 K23 K22 K21 K20 K19 K18 K17 K16 K15 K14 K13 K12 K11

216.59 217.15 218.15 219.15 220.15 221.15 222.15 223.15 224.15 225.15 226.15 227.15 228.15 229.15 230.15 231.15 232.15 233.15 234.15 235.15 236.15 237.15 238.15 239.15 240.15 241.15 242.15 243.15 244.15 245.15 246.15 247.15 248.15 249.15 250.15 251.15 252.15 253.15 254.15 255.15 256.15 257.15 258.15 259.15 260.15 261.15 262.15

5.18 5.31 5.54 5.78 6.03 6.29 6.55 6.82 7.10 7.39 7.69 8.00 8.32 8.64 8.98 9.33 9.68 10.05 10.42 10.81 11.20 11.61 12.02 12.45 12.89 13.34 13.80 14.28 14.76 15.26 15.77 16.29 16.83 17.38 17.94 18.51 19.10 19.70 20.31 20.94 21.58 22.24 22.91 23.59 24.29 25.01 25.74

26.777 26.732 26.650 26.568 26.485 26.402 26.318 26.234 26.150 26.065 25.979 25.894 25.807 25.720 25.633 25.545 25.457 25.368 25.278 25.188 25.097 25.006 24.914 24.821 24.727 24.633 24.539 24.443 24.347 24.250 24.152 24.053 23.953 23.853 23.752 23.649 23.546 23.442 23.336 23.230 23.122 23.014 22.904 22.792 22.680 22.566 22.451

0.31268 0.3200 0.3334 0.3473 0.3616 0.3764 0.3916 0.4073 0.4235 0.4402 0.4574 0.4752 0.4935 0.5123 0.5317 0.5517 0.5723 0.5935 0.6154 0.6378 0.6610 0.6848 0.7093 0.7345 0.7605 0.7872 0.8147 0.8430 0.8720 0.9020 0.9328 0.9645 0.9971 1.0306 1.0651 1.1006 1.1371 1.1747 1.2134 1.2532 1.2942 1.3364 1.3799 1.4246 1.4707 1.5182 1.5671 (continued)

CAT4240—Appendix A—2/11/2006—19:48—SRIDHAR—15608—XML MODEL C – pp. 835–854

Appendix A

837

TABLE A.1 —Continued Density (mol/L) T (8C) K10 K9 K8 K6 K5 K4 K3 K2 K1 0 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 30.978

T (K)

P (bar)

Sat’d Liq.

Sat’d Vap.

263.15 264.15 265.15 267.15 268.15 269.15 270.15 271.15 272.15 273.15 274.15 275.15 276.15 277.15 278.15 279.15 280.15 281.15 282.15 283.15 284.15 285.15 286.15 287.15 288.15 289.15 290.15 291.15 292.15 293.15 294.15 295.15 296.15 297.15 298.15 299.15 300.15 301.15 302.15 303.15 304.13

26.49 27.25 28.03 29.63 30.46 31.30 32.16 33.04 33.94 34.85 35.78 36.73 37.70 38.69 39.70 40.72 41.77 42.83 43.92 45.02 46.15 47.30 48.47 49.66 50.87 52.11 53.37 54.65 55.96 57.29 58.65 60.03 61.44 62.88 64.34 65.84 67.36 68.92 70.51 72.14 73.77

22.334 22.216 22.096 21.852 21.727 21.600 21.472 21.341 21.208 21.073 20.936 20.796 20.653 20.508 20.360 20.208 20.054 19.895 19.733 19.567 19.396 19.220 19.039 18.853 18.660 18.460 18.252 18.036 17.810 17.573 17.323 17.059 16.777 16.474 16.144 15.780 15.368 14.889 14.300 13.481 10.625

1.6175 1.6694 1.7230 1.8353 1.8941 1.9548 2.0176 2.0824 2.1494 2.2188 2.2905 2.3648 2.4418 2.5216 2.6044 2.6905 2.7799 2.8730 2.9699 3.0711 3.1767 3.2871 3.4029 3.5244 3.6521 3.7868 3.9293 4.0803 4.2410 4.4127 4.5971 4.7963 5.0130 5.2510 5.5154 5.8138 6.1581 6.5691 7.0900 7.8415 10.625

a

The densities as well as critical properties and the triple point of carbon dioxide were obtained from Chemistry Webbook, NIST (http://webbook.nist.gov/chemistry/ﬂuid/, July 2005).

CAT4240—Appendix A—2/11/2006—19:48—SRIDHAR—15608—XML MODEL C – pp. 835–854

838

Solubility in Supercritical Carbon Dioxide

TABLE A.2 Density of Saturated Carbon Dioxide versus Pressurea Density (mol/L) P (bar) 5.18 5.5 6 7 7 8 8 9 9 10 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45

T (8C)

T (K)

Sat’d Liq.

Sat’d Vap.

K56.558 K55.17 K53.12 K51.19 K49.37 K47.65 K46.01 K44.44 K42.94 K41.50 K40.12 K37.50 K35.06 K32.76 K30.58 K28.52 K26.56 K24.68 K22.89 K21.16 K19.50 K17.90 K16.36 K14.86 K13.42 K12.01 K10.65 K9.32 K8.03 K6.78 K5.55 K4.36 K3.19 K2.05 K0.93 0.16 1.23 2.28 3.30 4.31 5.30 6.27 7.22 8.16 9.08 9.98

216.59 217.98 220.04 221.96 223.78 225.51 227.15 228.71 230.21 231.65 233.03 235.65 238.09 240.39 242.57 244.63 246.59 248.47 250.26 251.99 253.65 255.25 256.79 258.29 259.73 261.14 262.50 263.83 265.12 266.37 267.60 268.79 269.96 271.10 272.22 273.31 274.38 275.43 276.45 277.46 278.45 279.42 280.37 281.31 282.23 283.13

26.777 26.664 26.494 26.334 26.181 26.035 25.894 25.759 25.628 25.501 25.379 25.143 24.919 24.705 24.499 24.300 24.108 23.922 23.740 23.563 23.389 23.219 23.053 22.889 22.727 22.568 22.410 22.255 22.101 21.948 21.796 21.646 21.496 21.347 21.199 21.051 20.904 20.757 20.609 20.462 20.315 20.167 20.019 19.870 19.720 19.570

0.3127 0.3311 0.3599 0.3887 0.4175 0.4463 0.4751 0.5040 0.5329 0.5619 0.5909 0.6492 0.7079 0.7669 0.8264 0.8863 0.9467 1.0076 1.0691 1.1312 1.1938 1.2572 1.3212 1.3859 1.4513 1.5175 1.5846 1.6524 1.7211 1.7908 1.8614 1.9330 2.0056 2.0793 2.1541 2.2301 2.3074 2.3859 2.4658 2.5471 2.6299 2.7142 2.8002 2.8880 2.9775 3.0690 (continued)

CAT4240—Appendix A—2/11/2006—19:48—SRIDHAR—15608—XML MODEL C – pp. 835–854

Appendix A

839

TABLE A.2 —Continued Density (mol/L) P (bar) 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 61 62 63 64 65 66 67 68 69 70 71 72 73 73.77

T (8C) 10.87 11.74 12.60 13.45 14.28 15.11 15.91 16.71 17.50 18.27 19.03 19.78 20.53 21.26 21.98 22.69 23.39 24.08 24.77 25.44 26.11 26.77 27.41 28.05 28.68 29.30 29.92 30.52 30.978

T (K)

Sat’d Liq.

Sat’d Vap.

284.02 284.89 285.75 286.60 287.43 288.26 289.06 289.86 290.65 291.42 292.18 292.93 293.68 294.41 295.13 295.84 296.54 297.23 297.92 298.59 299.26 299.92 300.56 301.20 301.83 302.45 303.07 303.67 304.13

19.418 19.266 19.112 18.956 18.798 18.639 18.477 18.313 18.146 17.976 17.803 17.625 17.444 17.257 17.065 16.867 16.661 16.447 16.223 15.988 15.738 15.470 15.181 14.862 14.504 14.086 13.565 12.812 10.625

3.1626 3.2583 3.3563 3.4568 3.5600 3.6659 3.7749 3.8871 4.0029 4.1225 4.2462 4.3745 4.5078 4.6467 4.7917 4.9437 5.1035 5.2723 5.4514 5.6427 5.8485 6.0720 6.3179 6.5930 6.9083 7.2839 7.7630 8.4780 10.625

a

The densities as well as critical properties and the triple point of carbon dioxide were obtained from Chemistry Webbook, NIST (http://webbook.nist.gov/chemistry/ﬂuid/, July 2005).

CAT4240—Appendix A—2/11/2006—19:48—SRIDHAR—15608—XML MODEL C – pp. 835–854

L56.56 (216.59)

0.3127

P (bar)

1 5 10 15 20 25 30 35 40 45 50 52 54 56 58 60 62 64 66 68 69 70 71 72 73 74 75 76 77 78

0.0559 0.2980 26.672 26.696 26.720 26.744 26.768 26.791 26.815 26.838 26.861 26.87 26.879 26.888 26.897 26.906 26.915 26.924 26.933 26.942 26.946 26.951 26.955 26.96 26.964 26.969 26.973 26.977 26.982 26.986

L55 (218.15)

0.0546 0.2895 26.251 26.278 26.304 26.33 26.356 26.382 26.407 26.433 26.458 26.468 26.478 26.487 26.497 26.507 26.517 26.527 26.536 26.546 26.551 26.556 26.561 26.565 26.57 26.575 26.58 26.585 26.589 26.594

L50 (223.15) L40 (233.15) 0.0522 0.2741 0.5904 25.400 25.432 25.464 25.495 25.526 25.557 25.587 25.617 25.629 25.641 25.653 25.665 25.677 25.688 25.7 25.712 25.723 25.729 25.735 25.74 25.746 25.752 25.758 25.763 25.769 25.775 25.78

L45 (228.15) 0.0534 0.2815 25.817 25.847 25.876 25.904 25.933 25.961 25.989 26.016 26.044 26.055 26.066 26.076 26.087 26.098 26.108 26.119 26.13 26.14 26.146 26.151 26.156 26.161 26.167 26.172 26.177 26.182 26.187 26.193 0.0510 0.2671 0.5714 24.935 24.971 25.006 25.041 25.076 25.11 25.143 25.177 25.19 25.203 25.216 25.229 25.242 25.255 25.268 25.28 25.293 25.3 25.306 25.312 25.318 25.325 25.331 25.337 25.343 25.35 25.356

L35 (238.15)

TABLE A.3 Density of Carbon Dioxide in the Single-Phase Region, mol/L

0.0500 0.2605 0.5540 24.449 24.489 24.529 24.568 24.607 24.645 24.682 24.719 24.734 24.748 24.763 24.777 24.792 24.806 24.82 24.834 24.848 24.855 24.862 24.869 24.876 24.883 24.89 24.897 24.904 24.911 24.918

L30 (243.15)

Temperature (8C) (Temperature (K))

0.0489 0.2544 0.5381 0.8635 23.982 24.028 24.072 24.115 24.158 24.2 24.242 24.258 24.275 24.291 24.307 24.323 24.339 24.355 24.37 24.386 24.394 24.402 24.409 24.417 24.425 24.433 24.44 24.448 24.455 24.463

L25 (248.15) 0.0479 0.2485 0.5233 0.8342 23.445 23.497 23.548 23.597 23.646 23.694 23.741 23.76 23.778 23.797 23.815 23.833 23.851 23.868 23.886 23.904 23.912 23.921 23.93 23.939 23.947 23.956 23.964 23.973 23.981 23.990

L20 (253.15) 0.0470 0.2430 0.5096 0.8077 1.1505 22.929 22.988 23.046 23.103 23.158 23.212 23.233 23.254 23.275 23.296 23.317 23.337 23.357 23.377 23.397 23.407 23.417 23.427 23.437 23.446 23.456 23.466 23.475 23.485 23.495

L15 (258.15) 0.0461 0.2377 0.4968 0.7836 1.1080 1.4886 22.384 22.453 22.52 22.585 22.648 22.673 22.697 22.721 22.745 22.769 22.793 22.816 22.839 22.862 22.873 22.885 22.896 22.907 22.918 22.929 22.94 22.951 22.962 22.973

L10 (263.15) 0.0452 0.2327 0.4848 0.7614 1.0703 1.4247 1.8499 21.804 21.885 21.963 22.039 22.068 22.097 22.126 22.154 22.182 22.21 22.237 22.264 22.291 22.304 22.318 22.331 22.344 22.357 22.369 22.382 22.395 22.408 22.42

L5 (268.15)

0.0443 0.2279 0.4735 0.7409 1.0363 1.3695 1.7572 21.076 21.18 21.277 21.371 21.407 21.442 21.477 21.511 21.545 21.579 21.611 21.644 21.675 21.691 21.707 21.722 21.738 21.753 21.768 21.783 21.798 21.813 21.828

0 (273.15)

840 Solubility in Supercritical Carbon Dioxide

CAT4240—Appendix A—2/11/2006—19:49—SRIDHAR—15608—XML MODEL C – pp. 835–854

79 80 82 84 86 88 90 92 94 96 98 100 105 110 115 120 125 130 135 140 145 150 160 170 180 190 200 210 220 230 240 250 260 270 280 290 300

26.599 26.604 26.613 26.623 26.632 26.641 26.651 26.66 26.669 26.679 26.688 26.697 26.72 26.743 26.765 26.788 26.81 26.832 26.854 26.876 26.898 26.919 26.962 27.004 27.045 27.086 27.127 27.166 27.206 27.245 27.283 27.321 27.359 27.396 27.433 27.469 27.505 26.198 26.203 26.213 26.223 26.234 26.244 26.254 26.264 26.274 26.284 26.294 26.304 26.329 26.354 26.378 26.403 26.427 26.451 26.474 26.498 26.521 26.544 26.59 26.635 26.68 26.723 26.767 26.809 26.852 26.893 26.934 26.975 27.015 27.054 27.093 27.132 27.17 25.786 25.792 25.803 25.814 25.825 25.836 25.847 25.858 25.869 25.88 25.891 25.902 25.929 25.956 25.982 26.009 26.035 26.061 26.086 26.112 26.137 26.162 26.211 26.26 26.308 26.355 26.401 26.447 26.492 26.536 26.58 26.623 26.666 26.708 26.75 26.791 26.831 25.362 25.368 25.381 25.393 25.405 25.417 25.429 25.441 25.453 25.465 25.477 25.489 25.519 25.548 25.577 25.605 25.634 25.662 25.689 25.717 25.744 25.771 25.825 25.877 25.929 25.979 26.029 26.078 26.127 26.174 26.221 26.267 26.313 26.358 26.402 26.446 26.489

24.924 24.931 24.945 24.958 24.972 24.985 24.998 25.012 25.025 25.038 25.051 25.064 25.096 25.128 25.16 25.191 25.222 25.252 25.283 25.313 25.342 25.372 25.429 25.486 25.542 25.597 25.65 25.703 25.755 25.806 25.856 25.906 25.955 26.003 26.05 26.096 26.142 24.471 24.478 24.493 24.508 24.523 24.538 24.553 24.567 24.582 24.596 24.611 24.625 24.661 24.696 24.73 24.765 24.798 24.832 24.865 24.898 24.93 24.962 25.025 25.086 25.147 25.206 25.264 25.321 25.377 25.432 25.486 25.539 25.591 25.642 25.693 25.742 25.791 23.998 24.007 24.024 24.04 24.057 24.073 24.09 24.106 24.122 24.138 24.154 24.17 24.209 24.248 24.286 24.324 24.361 24.398 24.434 24.47 24.506 24.541 24.609 24.676 24.742 24.806 24.869 24.931 24.991 25.05 25.108 25.165 25.221 25.276 25.33 25.383 25.435

23.504 23.514 23.533 23.551 23.570 23.588 23.607 23.625 23.643 23.661 23.679 23.697 23.741 23.784 23.826 23.868 23.909 23.95 23.99 24.029 24.068 24.107 24.182 24.255 24.327 24.397 24.465 24.532 24.597 24.661 24.723 24.785 24.845 24.904 24.962 25.018 25.074 22.984 22.995 23.016 23.038 23.059 23.08 23.101 23.121 23.142 23.162 23.182 23.202 23.251 23.3 23.347 23.394 23.44 23.485 23.529 23.573 23.616 23.659 23.741 23.822 23.9 23.976 24.051 24.123 24.194 24.263 24.331 24.397 24.461 24.525 24.587 24.648 24.708 22.433 22.445 22.47 22.495 22.519 22.543 22.567 22.59 22.614 22.637 22.66 22.682 22.738 22.793 22.847 22.899 22.951 23.001 23.051 23.099 23.147 23.194 23.286 23.375 23.461 23.544 23.625 23.704 23.781 23.856 23.93 24.001 24.071 24.139 24.206 24.271 24.335

Appendix A 841

CAT4240—Appendix A—2/11/2006—19:49—SRIDHAR—15608—XML MODEL C – pp. 835–854 21.843 21.857 21.886 21.915 21.943 21.971 21.999 22.026 22.053 22.08 22.106 22.133 22.197 22.259 22.32 22.38 22.438 22.495 22.551 22.606 22.659 22.712 22.814 22.912 23.007 23.099 23.188 23.274 23.358 23.44 23.519 23.597 23.672 23.746 23.818 23.888 23.957

(continued)

320 340 360 380 400 420 440 460 480 500 550 600 650 700 750 800 850 900 950 1000 1100 1200 1300 1400 1500 1600 1700 1800 1900 2000

P (bar)

L56.56 (216.59)

L55 (218.15)

TABLE A.3 —Continued

27.576

L50 (223.15) 27.245 27.319 27.39 27.461 27.53 27.597 27.663 27.729 27.792 27.855 28.007

L45 (228.15) 26.911 26.989 27.065 27.139 27.212 27.283 27.353 27.421 27.488 27.554 27.714 27.866 28.013 28.154 28.29 28.421

L40 (233.15) 26.574 26.656 26.737 26.815 26.892 26.967 27.041 27.112 27.183 27.252 27.419 27.579 27.732 27.879 28.02 28.156 28.288 28.415 28.538 28.658 28.887

L35 (238.15) 26.232 26.32 26.405 26.488 26.569 26.649 26.726 26.802 26.876 26.949 27.124 27.291 27.45 27.603 27.75 27.892 28.028 28.16 28.288 28.411 28.648 28.871 29.083 29.285

L30 (243.15)

Temperature (8C) (Temperature (K))

25.887 25.98 26.07 26.158 26.244 26.328 26.41 26.489 26.567 26.643 26.827 27.002 27.169 27.328 27.481 27.628 27.769 27.906 28.038 28.166 28.409 28.64 28.858 29.065 29.263 29.453 29.635

L25 (248.15) 25.537 25.636 25.732 25.825 25.916 26.005 26.091 26.175 26.257 26.337 26.529 26.712 26.886 27.052 27.211 27.364 27.511 27.652 27.789 27.921 28.172 28.409 28.634 28.847 29.05 29.244 29.43 29.609 29.781 29.947

L20 (253.15) 25.183 25.288 25.39 25.489 25.585 25.679 25.77 25.858 25.944 26.029 26.231 26.422 26.603 26.776 26.942 27.1 27.252 27.399 27.54 27.676 27.936 28.18 28.411 28.63 28.838 29.037 29.227 29.41 29.586 29.756

L15 (258.15) 24.824 24.936 25.045 25.149 25.251 25.35 25.446 25.539 25.63 25.719 25.931 26.131 26.32 26.5 26.672 26.837 26.995 27.146 27.292 27.433 27.701 27.952 28.189 28.414 28.627 28.831 29.026 29.213 29.393 29.566

L10 (263.15) 24.46 24.579 24.695 24.806 24.914 25.018 25.12 25.218 25.314 25.407 25.629 25.838 26.036 26.224 26.403 26.574 26.737 26.894 27.045 27.19 27.466 27.725 27.968 28.199 28.418 28.627 28.826 29.017 29.201 29.377

L5 (268.15)

24.09 24.218 24.34 24.459 24.573 24.684 24.791 24.895 24.995 25.093 25.327 25.546 25.752 25.948 26.133 26.311 26.48 26.642 26.798 26.948 27.233 27.499 27.749 27.986 28.21 28.424 28.628 28.823 29.01 29.191

0 (273.15)

842 Solubility in Supercritical Carbon Dioxide

CAT4240—Appendix A—2/11/2006—19:50—SRIDHAR—15608—XML MODEL C – pp. 835–854

5 (278.15)

0.0435 0.2233 0.4628 0.7218 1.0054 1.3208 1.6800 2.1044 20.368 20.498 20.619 20.665 20.71 20.754 20.798 20.84 20.881 20.922 20.962 21.001 21.02 21.039 21.058 21.077 21.095 21.114 21.132 21.15 21.168 21.186 21.204 21.221

P (bar)

1 5 10 15 20 25 30 35 40 45 50 52 54 56 58 60 62 64 66 68 69 70 71 72 73 74 75 76 77 78 79 80

0.0427 0.2190 0.4527 0.7040 0.9770 1.2773 1.6135 2.0000 2.4634 3.0679 19.737 19.801 19.863 19.922 19.98 20.036 20.09 20.143 20.195 20.245 20.269 20.293 20.317 20.341 20.364 20.388 20.41 20.433 20.455 20.478 20.499 20.521

10 (283.15)

0.0420 0.2148 0.4431 0.6873 0.9508 1.2379 1.5552 1.9125 2.3266 2.8294 3.5020 18.717 18.813 18.904 18.99 19.072 19.15 19.225 19.296 19.365 19.399 19.432 19.464 19.496 19.527 19.557 19.588 19.617 19.647 19.676 19.704 19.732

15 (288.15) 0.0412 0.2108 0.4340 0.6716 0.9265 1.2020 1.5032 1.8373 2.2152 2.6559 3.1958 3.4563 3.7573 4.1214 17.631 17.783 17.921 18.047 18.163 18.271 18.323 18.373 18.422 18.469 18.515 18.56 18.604 18.646 18.688 18.729 18.768 18.807

20 (293.15) 0.0407 0.2077 0.4270 0.6597 0.9082 1.1753 1.4653 1.7837 2.1388 2.5436 3.0208 3.2406 3.4836 3.7570 4.0731 4.4548 4.9560 16.631 16.868 17.068 17.158 17.243 17.324 17.400 17.473 17.542 17.609 17.673 17.734 17.794 17.851 17.907

24 (297.15) 0.0404 0.2062 0.4236 0.6539 0.8994 1.1627 1.4474 1.7588 2.1039 2.4938 2.9468 3.1523 3.3765 3.6240 3.9025 4.2238 4.6100 5.1107 15.817 16.187 16.335 16.467 16.587 16.697 16.799 16.895 16.984 17.069 17.149 17.226 17.299 17.368

26 (299.15) 0.0401 0.2047 0.4203 0.6483 0.8908 1.1503 1.4302 1.7349 2.0709 2.4474 2.8796 3.0733 3.2823 3.5101 3.7615 4.0438 4.3685 4.7563 5.2509 5.9853 14.925 15.269 15.522 15.728 15.904 16.058 16.196 16.321 16.436 16.543 16.642 16.736

28 (301.15)

Temperature (8C) (Temperature (K))

0.0399 0.2032 0.4170 0.6428 0.8825 1.1384 1.4136 1.7121 2.0395 2.4040 2.8180 3.0016 3.1982 3.4102 3.6411 3.8955 4.1804 4.5067 4.8932 5.3773 5.6809 6.0568 6.5710 7.5414 14.266 14.711 15.022 15.267 15.471 15.648 15.804 15.945

30 (303.15) 0.0396 0.2018 0.4138 0.6374 0.8743 1.1268 1.3975 1.6902 2.0097 2.3632 2.7610 2.9360 3.1221 3.3211 3.5357 3.7690 4.0255 4.3118 4.6380 5.0207 5.2419 5.4910 5.7779 6.1201 6.5514 7.1573 8.3147 12.668 13.673 14.183 14.539 14.818

32 (305.15) 0.0393 0.2004 0.4106 0.6321 0.8664 1.1155 1.3819 1.6691 1.9813 2.3247 2.7082 2.8755 3.0526 3.2408 3.4419 3.6584 3.8934 4.1511 4.4377 4.7621 4.9427 5.1388 5.3540 5.5932 5.8635 6.1764 6.5507 7.0221 7.6694 8.7175 10.758 12.417

34 (307.15) 0.0391 0.1990 0.4075 0.6269 0.8586 1.1045 1.3669 1.6488 1.9541 2.2883 2.6588 2.8195 2.9887 3.1675 3.3575 3.5603 3.7782 4.0141 4.2722 4.5578 4.7133 4.8790 5.0565 5.2480 5.4563 5.6851 5.9396 6.2271 6.5586 6.9517 7.4353 8.0606

36 (309.15) 0.0388 0.1976 0.4045 0.6218 0.8510 1.0938 1.3523 1.6292 1.9281 2.2537 2.6124 2.7672 2.9295 3.1002 3.2806 3.4719 3.6758 3.8946 4.1309 4.3883 4.5265 4.6720 4.8256 4.9887 5.1625 5.3487 5.5496 5.7680 6.0074 6.2728 6.5709 6.9108

38 (311.15)

CAT4240—Appendix A—2/11/2006—19:51—SRIDHAR—15608—XML MODEL C – pp. 835–854

(continued)

0.0386 0.1962 0.4015 0.6168 0.8436 1.0834 1.3381 1.6103 1.9032 2.2208 2.5688 2.7182 2.8743 3.0380 3.2100 3.3915 3.5838 3.7884 4.0075 4.2434 4.3687 4.4995 4.6364 4.7802 4.9315 5.0914 5.2609 5.4415 5.6348 5.8429 6.0684 6.3144

40 (313.15)

Appendix A 843

5 (278.15)

21.256 21.29 21.324 21.357 21.39 21.422 21.454 21.485 21.516 21.546 21.621 21.693 21.764 21.832 21.899 21.964 22.027 22.089 22.149 22.208 22.323 22.432 22.538 22.639 22.737 22.832 22.924 23.013 23.099 23.183 23.265

P (bar)

82 84 86 88 90 92 94 96 98 100 105 110 115 120 125 130 135 140 145 150 160 170 180 190 200 210 220 230 240 250 260

20.564 20.606 20.647 20.687 20.727 20.766 20.804 20.841 20.878 20.915 21.003 21.089 21.171 21.25 21.328 21.402 21.475 21.546 21.614 21.681 21.81 21.933 22.051 22.163 22.272 22.376 22.477 22.575 22.669 22.76 22.849

10 (283.15)

TABLE A.3 —Continued

19.787 19.84 19.893 19.943 19.993 20.041 20.089 20.135 20.181 20.225 20.332 20.435 20.533 20.627 20.718 20.805 20.889 20.971 21.05 21.126 21.273 21.412 21.544 21.67 21.791 21.906 22.017 22.124 22.227 22.327 22.423

15 (288.15) 18.883 18.956 19.026 19.093 19.159 19.222 19.283 19.343 19.401 19.457 19.592 19.719 19.839 19.952 20.061 20.165 20.264 20.359 20.451 20.54 20.708 20.867 21.016 21.157 21.292 21.42 21.543 21.66 21.773 21.882 21.988

20 (293.15) 18.013 18.113 18.208 18.298 18.384 18.466 18.546 18.621 18.695 18.765 18.932 19.086 19.23 19.365 19.493 19.614 19.729 19.838 19.943 20.044 20.233 20.41 20.576 20.731 20.879 21.019 21.152 21.279 21.402 21.519 21.631

24 (297.15) 17.5 17.622 17.736 17.844 17.945 18.042 18.133 18.221 18.304 18.385 18.573 18.745 18.904 19.053 19.192 19.323 19.447 19.565 19.678 19.785 19.987 20.174 20.349 20.513 20.667 20.814 20.953 21.086 21.212 21.334 21.451

26 (299.15) 16.908 17.063 17.206 17.337 17.46 17.575 17.683 17.785 17.882 17.975 18.189 18.383 18.561 18.725 18.878 19.021 19.156 19.283 19.404 19.519 19.735 19.933 20.118 20.29 20.453 20.606 20.751 20.889 21.021 21.147 21.268

28 (301.15)

Temperature (8C) (Temperature (K))

16.191 16.403 16.591 16.759 16.912 17.053 17.184 17.307 17.422 17.53 17.778 17.998 18.198 18.381 18.549 18.706 18.853 18.991 19.121 19.245 19.476 19.687 19.882 20.064 20.234 20.394 20.546 20.69 20.828 20.959 21.084

30 (303.15) 15.245 15.574 15.844 16.075 16.277 16.458 16.622 16.772 16.912 17.041 17.332 17.586 17.812 18.017 18.204 18.377 18.537 18.688 18.829 18.962 19.209 19.434 19.641 19.833 20.012 20.18 20.339 20.489 20.632 20.768 20.898

32 (305.15) 13.728 14.401 14.862 15.217 15.507 15.754 15.970 16.163 16.337 16.496 16.844 17.141 17.4 17.631 17.841 18.032 18.208 18.372 18.526 18.67 18.935 19.175 19.395 19.597 19.786 19.962 20.128 20.285 20.434 20.575 20.71

34 (307.15) 10.119 12.267 13.366 14.032 14.508 14.879 15.185 15.445 15.673 15.875 16.304 16.657 16.957 17.221 17.456 17.669 17.864 18.044 18.211 18.367 18.653 18.909 19.143 19.357 19.556 19.741 19.914 20.078 20.233 20.38 20.52

36 (309.15) 7.7742 9.0382 10.742 12.165 13.086 13.716 14.189 14.567 14.881 15.151 15.696 16.124 16.478 16.782 17.049 17.287 17.503 17.701 17.884 18.054 18.362 18.637 18.885 19.112 19.321 19.516 19.698 19.869 20.03 20.183 20.329

38 (311.15)

6.8860 7.6054 8.5423 9.7501 11.032 12.089 12.869 13.451 13.908 14.283 15 15.531 15.955 16.309 16.614 16.883 17.124 17.343 17.543 17.729 18.062 18.357 18.621 18.862 19.082 19.287 19.478 19.656 19.825 19.984 20.135

40 (313.15)

844 Solubility in Supercritical Carbon Dioxide

CAT4240—Appendix A—2/11/2006—19:51—SRIDHAR—15608—XML MODEL C – pp. 835–854

270 280 290 300 320 340 360 380 400 420 440 460 480 500 550 600 650 700 750 800 850 900 950 1000 1100 1200 1300 1400 1500 1600 1700 1800 1900 2000

23.345 23.422 23.498 23.572 23.714 23.851 23.982 24.108 24.229 24.346 24.459 24.569 24.675 24.778 25.023 25.252 25.467 25.671 25.864 26.048 26.223 26.391 26.552 26.707 27 27.274 27.531 27.773 28.003 28.222 28.43 28.63 28.821 29.005

22.935 23.019 23.1 23.18 23.333 23.479 23.619 23.753 23.882 24.006 24.125 24.241 24.353 24.461 24.718 24.957 25.182 25.394 25.595 25.786 25.967 26.141 26.307 26.467 26.769 27.05 27.314 27.563 27.798 28.022 28.235 28.438 28.634 28.821

22.517 22.607 22.695 22.781 22.946 23.102 23.251 23.394 23.531 23.662 23.788 23.91 24.028 24.142 24.412 24.662 24.897 25.117 25.326 25.523 25.711 25.891 26.063 26.227 26.538 26.827 27.098 27.353 27.594 27.823 28.04 28.248 28.448 28.639

22.089 22.187 22.283 22.375 22.552 22.72 22.879 23.031 23.176 23.315 23.449 23.578 23.702 23.821 24.104 24.366 24.611 24.841 25.057 25.262 25.456 25.642 25.819 25.989 26.309 26.606 26.884 27.145 27.391 27.625 27.848 28.06 28.263 28.458 21.74 21.845 21.946 22.045 22.232 22.41 22.578 22.737 22.89 23.036 23.176 23.31 23.439 23.564 23.858 24.129 24.382 24.619 24.842 25.053 25.253 25.443 25.625 25.799 26.126 26.429 26.713 26.979 27.23 27.468 27.694 27.91 28.116 28.314 21.563 21.672 21.776 21.878 22.071 22.253 22.426 22.59 22.746 22.895 23.038 23.175 23.308 23.435 23.734 24.011 24.268 24.508 24.735 24.948 25.151 25.344 25.528 25.704 26.035 26.342 26.628 26.897 27.15 27.39 27.618 27.835 28.043 28.242

21.385 21.497 21.605 21.71 21.909 22.096 22.273 22.442 22.602 22.754 22.901 23.041 23.176 23.305 23.61 23.892 24.153 24.398 24.627 24.844 25.049 25.245 25.431 25.609 25.944 26.254 26.543 26.814 27.07 27.312 27.542 27.761 27.97 28.171 21.205 21.321 21.432 21.54 21.745 21.938 22.12 22.293 22.457 22.613 22.762 22.906 23.043 23.176 23.487 23.773 24.039 24.287 24.52 24.74 24.948 25.146 25.334 25.514 25.853 26.166 26.458 26.732 26.99 27.234 27.466 27.687 27.898 28.1 21.023 21.143 21.258 21.37 21.581 21.779 21.966 22.143 22.311 22.471 22.624 22.77 22.911 23.046 23.363 23.654 23.924 24.176 24.413 24.636 24.847 25.047 25.238 25.42 25.762 26.079 26.374 26.65 26.911 27.157 27.39 27.613 27.826 28.029 20.84 20.964 21.083 21.198 21.416 21.62 21.812 21.993 22.165 22.329 22.485 22.635 22.778 22.916 23.239 23.535 23.81 24.066 24.306 24.532 24.745 24.948 25.141 25.326 25.672 25.992 26.29 26.569 26.831 27.079 27.315 27.539 27.753 27.959

20.654 20.783 20.906 21.025 21.249 21.459 21.656 21.842 22.019 22.186 22.346 22.499 22.645 22.786 23.115 23.416 23.695 23.955 24.199 24.428 24.644 24.85 25.045 25.232 25.582 25.905 26.206 26.487 26.752 27.002 27.24 27.466 27.682 27.888 20.468 20.6 20.728 20.85 21.082 21.298 21.5 21.691 21.872 22.043 22.206 22.362 22.512 22.655 22.99 23.297 23.581 23.845 24.092 24.324 24.543 24.751 24.949 25.138 25.492 25.818 26.122 26.406 26.673 26.925 27.165 27.393 27.61 27.818

CAT4240—Appendix A—2/11/2006—19:52—SRIDHAR—15608—XML MODEL C – pp. 835–854

(continued)

20.279 20.417 20.548 20.675 20.913 21.135 21.343 21.539 21.724 21.9 22.066 22.226 22.378 22.524 22.866 23.178 23.466 23.734 23.985 24.22 24.442 24.653 24.853 25.044 25.402 25.732 26.038 26.325 26.594 26.849 27.09 27.32 27.539 27.748

Appendix A 845

1 5 10 15 20 25 30 35 40 45 50 52 54 56 58 60 62 64 66 68 69 70 71 72 73 74 75 76 77 78 79 80 82

P (bar)

0.0380 0.1929 0.3942 0.6048 0.8258 1.0585 1.3045 1.5659 1.8449 2.1449 2.4697 2.6078 2.7511 2.9001 3.0554 3.2176 3.3874 3.5657 3.7536 3.9521 4.0558 4.1628 4.2732 4.3874 4.5056 4.6281 4.7553 4.8876 5.0253 5.1691 5.3195 5.4772 5.8172

45 (318.15)

0.0374 0.1897 0.3872 0.5933 0.8089 1.0351 1.2732 1.5248 1.7918 2.0767 2.3823 2.5112 2.6443 2.7819 2.9244 3.0722 3.2257 3.3855 3.5521 3.7262 3.8163 3.9086 4.0031 4.1000 4.1995 4.3016 4.4066 4.5146 4.6258 4.7403 4.8584 4.9803 5.2366

50 (323.15)

TABLE A.3—Continued

0.0368 0.1867 0.3805 0.5823 0.7928 1.0129 1.2438 1.4866 1.7430 2.0148 2.3042 2.4255 2.5502 2.6786 2.8109 2.9474 3.0885 3.2343 3.3853 3.5418 3.6223 3.7044 3.7881 3.8735 3.9607 4.0497 4.1406 4.2336 4.3286 4.4258 4.5253 4.6273 4.8388

55 (328.15) 0.0362 0.1837 0.3741 0.5718 0.7775 0.9920 1.2162 1.4511 1.6979 1.9582 2.2336 2.3484 2.4661 2.5869 2.7108 2.8382 2.9692 3.1041 3.2430 3.3862 3.4595 3.5341 3.6098 3.6868 3.7651 3.8448 3.9259 4.0084 4.0925 4.1781 4.2652 4.3541 4.5371

60 (333.15) 0.0357 0.1808 0.3679 0.5617 0.7629 0.9722 1.1901 1.4178 1.6560 1.9061 2.1692 2.2785 2.3902 2.5045 2.6214 2.7412 2.8640 2.9899 3.1191 3.2518 3.3195 3.3881 3.4577 3.5283 3.5999 3.6725 3.7462 3.8210 3.8970 3.9741 4.0524 4.1319 4.2948

65 (338.15) 0.0352 0.1780 0.3619 0.5521 0.7490 0.9533 1.1655 1.3865 1.6169 1.8578 2.1101 2.2145 2.3210 2.4297 2.5407 2.6541 2.7699 2.8884 3.0096 3.1336 3.1967 3.2606 3.3253 3.3907 3.4570 3.5240 3.5920 3.6608 3.7305 3.8011 3.8726 3.9451 4.0930

70 (343.15) 0.0346 0.1753 0.3561 0.5428 0.7357 0.9353 1.1422 1.3570 1.5803 1.8129 2.0555 2.1556 2.2576 2.3614 2.4672 2.5750 2.6849 2.7971 2.9115 3.0283 3.0876 3.1476 3.2081 3.2694 3.3313 3.3938 3.4571 3.5211 3.5857 3.6511 3.7173 3.7842 3.9204

75 (348.15)

Temperature (8C) (Temperature (K))

0.0342 0.1727 0.3506 0.5338 0.7229 0.9181 1.1200 1.3291 1.5458 1.7709 2.0049 2.1011 2.1990 2.2985 2.3997 2.5027 2.6075 2.7142 2.8228 2.9334 2.9895 3.0462 3.1033 3.1610 3.2192 3.2781 3.3374 3.3974 3.4579 3.5191 3.5808 3.6432 3.7699

80 (353.15) 0.0332 0.1678 0.3400 0.5169 0.6988 0.8860 1.0788 1.2775 1.4826 1.6944 1.9133 2.0030 2.0940 2.1862 2.2797 2.3746 2.4709 2.5685 2.6677 2.7683 2.8192 2.8704 2.9221 2.9742 3.0266 3.0795 3.1327 3.1864 3.2405 3.2950 3.3500 3.4054 3.5175

90 (363.15) 0.0323 0.1631 0.3300 0.5011 0.6765 0.8565 1.0412 1.2308 1.4258 1.6263 1.8326 1.9168 2.0020 2.0882 2.1755 2.2639 2.3533 2.4438 2.5354 2.6282 2.6750 2.7221 2.7696 2.8173 2.8653 2.9136 2.9622 3.0112 3.0604 3.1100 3.1599 3.2101 3.3114

100 (373.15) 0.0315 0.1586 0.3207 0.4864 0.6558 0.8292 1.0066 1.1882 1.3743 1.5650 1.7604 1.8400 1.9204 2.0016 2.0837 2.1666 2.2503 2.3350 2.4205 2.5069 2.5505 2.5942 2.6383 2.6825 2.7270 2.7717 2.8167 2.8619 2.9073 2.9530 2.9989 3.0450 3.1381

110 (383.15) 0.0307 0.1545 0.3120 0.4726 0.6365 0.8039 0.9747 1.1491 1.3273 1.5093 1.6954 1.7709 1.8472 1.9241 2.0017 2.0800 2.1590 2.2387 2.3191 2.4002 2.4411 2.4821 2.5233 2.5647 2.6063 2.6480 2.6900 2.7321 2.7745 2.8170 2.8597 2.9026 2.9890

120 (393.15)

0.0299 0.1505 0.3037 0.4597 0.6185 0.7803 0.9451 1.1130 1.2841 1.4585 1.6362 1.7083 1.7809 1.8541 1.9278 2.0021 2.0770 2.1525 2.2286 2.3052 2.3438 2.3824 2.4213 2.4603 2.4994 2.5387 2.5782 2.6178 2.6575 2.6974 2.7375 2.7777 2.8586

130 (403.15)

846 Solubility in Supercritical Carbon Dioxide

CAT4240—Appendix A—2/11/2006—19:53—SRIDHAR—15608—XML MODEL C – pp. 835–854

84 86 88 90 92 94 96 98 100 105 110 115 120 125 130 135 140 145 150 160 170 180 190 200 210 220 230 240 250 260 270 280 290 300 320 340 360 380

6.1964 6.6238 7.1106 7.6691 8.3094 9.0328 9.8155 10.598 11.321 12.742 13.705 14.403 14.945 15.388 15.761 16.085 16.371 16.627 16.859 17.268 17.622 17.933 18.213 18.466 18.698 18.913 19.113 19.3 19.476 19.642 19.8 19.95 20.093 20.23 20.488 20.726 20.948 21.157

5.5115 5.8075 6.1278 6.4758 6.8550 7.2690 7.7202 8.2092 8.7328 10.124 11.421 12.471 13.286 13.929 14.454 14.894 15.273 15.605 15.9 16.407 16.834 17.203 17.529 17.821 18.085 18.328 18.552 18.76 18.955 19.138 19.31 19.474 19.63 19.778 20.056 20.312 20.549 20.771

5.0613 5.2959 5.5439 5.8065 6.0852 6.3813 6.6962 7.0310 7.3864 8.3618 9.4275 10.494 11.464 12.291 12.982 13.561 14.053 14.477 14.849 15.476 15.992 16.43 16.81 17.146 17.448 17.722 17.973 18.204 18.42 18.621 18.81 18.989 19.158 19.319 19.618 19.893 20.147 20.383

4.7274 4.9258 5.1326 5.3486 5.5744 5.8107 6.0580 6.3171 6.5883 7.3216 8.1299 8.9931 9.8711 10.714 11.483 12.162 12.756 13.273 13.726 14.485 15.101 15.616 16.057 16.444 16.787 17.096 17.376 17.634 17.872 18.094 18.301 18.495 18.679 18.853 19.175 19.47 19.741 19.992 4.4631 4.6370 4.8169 5.0032 5.1960 5.3959 5.6031 5.8179 6.0407 6.6338 7.2791 7.9720 8.6996 9.4402 10.167 10.856 11.491 12.066 12.582 13.46 14.175 14.771 15.277 15.717 16.105 16.452 16.765 17.05 17.313 17.556 17.782 17.994 18.193 18.381 18.728 19.043 19.332 19.599 4.2449 4.4012 4.5618 4.7271 4.8973 5.0724 5.2528 5.4386 5.6299 6.1336 6.6741 7.2506 7.8584 8.4888 9.1286 9.7625 10.375 10.955 11.495 12.446 13.242 13.911 14.482 14.975 15.409 15.794 16.141 16.456 16.744 17.01 17.257 17.486 17.702 17.904 18.277 18.614 18.921 19.204

4.0597 4.2024 4.3485 4.4981 4.6515 4.8086 4.9697 5.1348 5.3040 5.7456 6.2144 6.7101 7.2311 7.7733 8.3304 8.8939 9.4543 10.002 10.528 11.495 12.337 13.062 13.687 14.229 14.706 15.13 15.511 15.855 16.169 16.458 16.726 16.974 17.206 17.424 17.823 18.183 18.509 18.808 3.8991 4.0310 4.1656 4.3031 4.4434 4.5868 4.7332 4.8827 5.0353 5.4312 5.8479 6.2853 6.7425 7.2177 7.7075 8.2073 8.7112 9.2129 9.7059 10.644 11.495 12.249 12.912 13.495 14.01 14.468 14.88 15.253 15.592 15.904 16.192 16.459 16.708 16.942 17.368 17.75 18.096 18.412 3.6314 3.7471 3.8646 3.9841 4.1055 4.2289 4.3542 4.4816 4.6111 4.9438 5.2896 5.6485 6.0202 6.4040 6.7987 7.2027 7.6137 8.0292 8.4459 9.2708 10.064 10.808 11.492 12.115 12.678 13.188 13.649 14.07 14.454 14.807 15.133 15.435 15.717 15.98 16.459 16.887 17.272 17.623 3.4141 3.5181 3.6235 3.7302 3.8382 3.9477 4.0586 4.1709 4.2846 4.5752 4.8747 5.1832 5.5004 5.8260 6.1594 6.4998 6.8462 7.1973 7.5517 8.2638 8.9686 9.6526 10.305 10.919 11.49 12.019 12.506 12.956 13.371 13.755 14.11 14.441 14.75 15.039 15.566 16.036 16.458 16.842

3.2322 3.3272 3.4233 3.5203 3.6184 3.7176 3.8177 3.9189 4.0212 4.2814 4.5480 4.8211 5.1005 5.3859 5.6769 5.9732 6.2741 6.5790 6.8871 7.5091 8.1322 8.7478 9.3481 9.9261 10.477 10.998 11.488 11.947 12.376 12.777 13.152 13.502 13.831 14.14 14.705 15.21 15.665 16.079 3.0762 3.1641 3.2528 3.3423 3.4326 3.5237 3.6155 3.7082 3.8016 4.0386 4.2806 4.5273 4.7786 5.0345 5.2946 5.5586 5.8262 6.0969 6.3704 6.9230 7.4792 8.0335 8.5805 9.1150 9.6329 10.131 10.607 11.059 11.487 11.893 12.275 12.636 12.976 13.297 13.889 14.421 14.903 15.342

CAT4240—Appendix A—2/11/2006—19:53—SRIDHAR—15608—XML MODEL C – pp. 835–854

(continued)

2.9401 3.0222 3.1049 3.1882 3.2722 3.3567 3.4419 3.5277 3.6142 3.8329 4.0553 4.2815 4.5112 4.7444 4.9808 5.2202 5.4624 5.7070 5.9539 6.4525 6.9551 7.4580 7.9575 8.4499 8.9318 9.4005 9.8537 10.29 10.708 11.107 11.487 11.85 12.194 12.521 13.129 13.679 14.18 14.638

Appendix A 847

45 (318.15)

21.353 21.539 21.715 21.883 22.044 22.197 22.555 22.881 23.18 23.458 23.718 23.961 24.191 24.408 24.614 24.811 25.178 25.516 25.83 26.123 26.399 26.658 26.904 27.138 27.361 27.574

P (bar)

400 420 440 460 480 500 550 600 650 700 750 800 850 900 950 1000 1100 1200 1300 1400 1500 1600 1700 1800 1900 2000

20.98 21.176 21.363 21.539 21.708 21.869 22.243 22.583 22.895 23.183 23.452 23.703 23.94 24.164 24.376 24.578 24.955 25.302 25.623 25.923 26.204 26.469 26.72 26.958 27.185 27.402

50 (323.15)

TABLE A.3 —Continued

20.604 20.812 21.008 21.194 21.371 21.54 21.931 22.286 22.61 22.909 23.187 23.446 23.691 23.921 24.139 24.347 24.734 25.089 25.418 25.724 26.011 26.281 26.537 26.779 27.01 27.231

55 (328.15) 20.226 20.446 20.653 20.849 21.034 21.211 21.62 21.989 22.325 22.635 22.922 23.191 23.442 23.679 23.904 24.117 24.514 24.878 25.214 25.527 25.819 26.095 26.355 26.602 26.837 27.061

60 (333.15) 19.847 20.079 20.296 20.502 20.697 20.882 21.309 21.692 22.041 22.362 22.659 22.936 23.195 23.439 23.67 23.888 24.295 24.668 25.011 25.331 25.629 25.91 26.175 26.426 26.665 26.893

65 (338.15) 19.466 19.711 19.94 20.156 20.36 20.553 20.998 21.397 21.759 22.09 22.397 22.682 22.949 23.2 23.437 23.661 24.078 24.459 24.81 25.136 25.44 25.726 25.996 26.252 26.495 26.726

70 (343.15) 19.085 19.342 19.583 19.809 20.023 20.225 20.688 21.102 21.477 21.82 22.136 22.43 22.705 22.962 23.205 23.436 23.862 24.252 24.61 24.943 25.253 25.544 25.819 26.079 26.326 26.561

75 (348.15)

Temperature (8C) (Temperature (K))

18.704 18.975 19.227 19.464 19.687 19.897 20.379 20.809 21.197 21.551 21.877 22.179 22.462 22.726 22.975 23.211 23.648 24.046 24.412 24.751 25.067 25.364 25.643 25.907 26.158 26.397

80 (353.15) 17.944 18.242 18.518 18.776 19.018 19.247 19.766 20.227 20.641 21.018 21.363 21.683 21.98 22.259 22.521 22.768 23.224 23.639 24.02 24.372 24.7 25.007 25.296 25.568 25.827 26.073

90 (363.15) 17.193 17.517 17.817 18.096 18.358 18.604 19.161 19.653 20.093 20.492 20.857 21.194 21.506 21.798 22.073 22.331 22.807 23.239 23.635 23.999 24.339 24.656 24.954 25.235 25.502 25.755

100 (373.15) 16.457 16.806 17.128 17.428 17.708 17.971 18.566 19.088 19.554 19.975 20.359 20.713 21.04 21.346 21.632 21.901 22.397 22.846 23.255 23.633 23.984 24.311 24.618 24.908 25.182 25.442

110 (383.15) 15.744 16.114 16.457 16.775 17.073 17.353 17.983 18.534 19.025 19.468 19.871 20.241 20.583 20.901 21.2 21.48 21.995 22.459 22.883 23.273 23.635 23.972 24.288 24.586 24.867 25.135

120 (393.15)

15.059 15.448 15.808 16.143 16.457 16.751 17.414 17.993 18.508 18.971 19.392 19.778 20.135 20.466 20.776 21.066 21.6 22.08 22.518 22.92 23.292 23.639 23.964 24.27 24.559 24.833

130 (403.15)

848 Solubility in Supercritical Carbon Dioxide

CAT4240—Appendix A—2/11/2006—19:53—SRIDHAR—15608—XML MODEL C – pp. 835–854

1 5 10 15 20 25 30 35 40 45 50 52 54 56 58 60 62 64 66 68 69 70 71 72 73 74 75 76 77 78 79 80

P (bar)

0.0292 0.1467 0.2959 0.4475 0.6015 0.7582 0.9175 1.0795 1.2442 1.4117 1.5820 1.6510 1.7204 1.7903 1.8607 1.9315 2.0029 2.0747 2.1470 2.2197 2.2563 2.2930 2.3298 2.3668 2.4038 2.4410 2.4783 2.5157 2.5533 2.5910 2.6288 2.6667

140 (413.15)

0.0285 0.1432 0.2885 0.4359 0.5856 0.7375 0.8917 1.0483 1.2072 1.3685 1.5322 1.5984 1.6649 1.7319 1.7993 1.8671 1.9352 2.0038 2.0728 2.1422 2.1770 2.2120 2.2470 2.2822 2.3174 2.3528 2.3882 2.4238 2.4595 2.4952 2.5311 2.5671

150 (423.15)

0.0278 0.1398 0.2814 0.4250 0.5706 0.7181 0.8676 1.0191 1.1727 1.3283 1.4860 1.5497 1.6137 1.6781 1.7428 1.8078 1.8732 1.9389 2.0050 2.0713 2.1047 2.1381 2.1716 2.2051 2.2388 2.2726 2.3064 2.3403 2.3743 2.4084 2.4426 2.4768

160 (433.15) 0.0272 0.1365 0.2748 0.4147 0.5563 0.6997 0.8449 0.9918 1.1404 1.2909 1.4432 1.5046 1.5663 1.6283 1.6905 1.7531 1.8159 1.8791 1.9425 2.0062 2.0382 2.0702 2.1023 2.1345 2.1668 2.1991 2.2315 2.2639 2.2965 2.3291 2.3618 2.3945

170 (443.15) 0.0266 0.1335 0.2684 0.4049 0.5429 0.6824 0.8235 0.9661 1.1102 1.2559 1.4032 1.4625 1.5221 1.5819 1.6420 1.7023 1.7629 1.8237 1.8848 1.9461 1.9768 2.0076 2.0385 2.0694 2.1004 2.1314 2.1625 2.1937 2.2249 2.2562 2.2875 2.3189

180 (453.15) 0.0260 0.1305 0.2624 0.3956 0.5301 0.6660 0.8032 0.9418 1.0818 1.2231 1.3657 1.4231 1.4808 1.5386 1.5967 1.6550 1.7135 1.7722 1.8311 1.8902 1.9198 1.9495 1.9793 2.0091 2.0389 2.0688 2.0987 2.1287 2.1588 2.1889 2.2190 2.2492

190 (463.15) 0.0254 0.1277 0.2566 0.3867 0.5180 0.6504 0.7841 0.9190 1.0550 1.1922 1.3306 1.3862 1.4421 1.4981 1.5543 1.6107 1.6673 1.7241 1.7810 1.8382 1.8668 1.8955 1.9242 1.9529 1.9817 2.0106 2.0395 2.0684 2.0974 2.1264 2.1554 2.1845

200 (473.15)

Temperature (8C) (Temperature (K))

0.0244 0.1224 0.2458 0.3701 0.4954 0.6216 0.7487 0.8767 1.0056 1.1355 1.2662 1.3187 1.3714 1.4242 1.4771 1.5302 1.5834 1.6367 1.6902 1.7438 1.7707 1.7975 1.8245 1.8514 1.8784 1.9054 1.9324 1.9595 1.9866 2.0137 2.0409 2.0681

220 (493.15) 0.0235 0.1176 0.2359 0.3550 0.4748 0.5953 0.7166 0.8386 0.9612 1.0846 1.2086 1.2584 1.3083 1.3583 1.4083 1.4585 1.5088 1.5592 1.6097 1.6603 1.6856 1.7110 1.7363 1.7617 1.7872 1.8126 1.8381 1.8636 1.8891 1.9146 1.9402 1.9657

240 (513.15) 0.0226 0.1131 0.2268 0.3411 0.4560 0.5714 0.6874 0.8039 0.9210 1.0385 1.1566 1.2040 1.2514 1.2990 1.3465 1.3942 1.4420 1.4898 1.5377 1.5856 1.6096 1.6336 1.6577 1.6817 1.7058 1.7299 1.7540 1.7781 1.8023 1.8264 1.8506 1.8748

260 (533.15) 0.0218 0.1090 0.2184 0.3283 0.4386 0.5494 0.6606 0.7722 0.8842 0.9966 1.1094 1.1546 1.1999 1.2452 1.2906 1.3360 1.3815 1.4271 1.4727 1.5183 1.5412 1.5640 1.5869 1.6097 1.6326 1.6555 1.6784 1.7014 1.7243 1.7472 1.7702 1.7932

280 (553.15) 0.0210 0.1051 0.2106 0.3164 0.4226 0.5291 0.6360 0.7431 0.8506 0.9583 1.0663 1.1096 1.1529 1.1963 1.2397 1.2831 1.3266 1.3701 1.4136 1.4572 1.4790 1.5008 1.5226 1.5445 1.5663 1.5882 1.6100 1.6319 1.6537 1.6756 1.6975 1.7194

300 (573.15)

CAT4240—Appendix A—2/11/2006—19:55—SRIDHAR—15608—XML MODEL C – pp. 835–854

(continued)

0.0203 0.1015 0.2033 0.3054 0.4078 0.5104 0.6132 0.7163 0.8196 0.9230 1.0267 1.0682 1.1098 1.1514 1.1930 1.2346 1.2763 1.3180 1.3597 1.4014 1.4223 1.4432 1.4640 1.4849 1.5058 1.5267 1.5476 1.5685 1.5895 1.6104 1.6313 1.6522

320 (593.15)

Appendix A 849

140 (413.15)

2.7429 2.8196 2.8969 2.9746 3.0528 3.1315 3.2107 3.2904 3.3706 3.4512 3.6550 3.8617 4.0713 4.2837 4.4988 4.7164 4.9363 5.1585 5.3826 5.6084 6.0642 6.5236 6.9841 7.4430 7.8977 8.3456 8.7845 9.2125 9.6279 10.03 10.417

P (bar)

82 84 86 88 90 92 94 96 98 100 105 110 115 120 125 130 135 140 145 150 160 170 180 190 200 210 220 230 240 250 260

2.6393 2.7119 2.7850 2.8584 2.9323 3.0065 3.0812 3.1562 3.2317 3.3075 3.4988 3.6925 3.8884 4.0866 4.2869 4.4891 4.6933 4.8991 5.1066 5.3154 5.7364 6.1605 6.5858 7.0105 7.4325 7.8499 8.2609 8.6640 9.0577 9.4410 9.8130

150 (423.15)

TABLE A.3 —Continued

2.5456 2.6147 2.6841 2.7539 2.8240 2.8944 2.9651 3.0362 3.1076 3.1793 3.3600 3.5426 3.7270 3.9132 4.1011 4.2907 4.4817 4.6740 4.8677 5.0624 5.4546 5.8494 6.2453 6.6409 7.0347 7.4253 7.8111 8.1910 8.5637 8.9284 9.2841

160 (433.15) 2.4602 2.5262 2.5924 2.6590 2.7258 2.7929 2.8602 2.9278 2.9957 3.0639 3.2354 3.4084 3.5830 3.7590 3.9364 4.1151 4.2949 4.4759 4.6579 4.8408 5.2087 5.5788 5.9498 6.3206 6.6901 7.0572 7.4206 7.7794 8.1326 8.4794 8.8190

170 (443.15) 2.3819 2.4451 2.5086 2.5723 2.6362 2.7003 2.7647 2.8292 2.8940 2.9590 3.1225 3.2873 3.4533 3.6204 3.7887 3.9581 4.1284 4.2996 4.4716 4.6443 4.9915 5.3404 5.6900 6.0395 6.3880 6.7345 7.0781 7.4179 7.7532 8.0833 8.4076

180 (453.15) 2.3097 2.3705 2.4314 2.4925 2.5538 2.6153 2.6770 2.7389 2.8010 2.8632 3.0196 3.1770 3.3355 3.4949 3.6552 3.8164 3.9784 4.1411 4.3045 4.4684 4.7976 5.1282 5.4593 5.7902 6.1203 6.4487 6.7747 7.0976 7.4167 7.7315 8.0414

190 (463.15) 2.2429 2.3014 2.3600 2.4189 2.4778 2.5370 2.5963 2.6557 2.7153 2.7751 2.9251 3.0760 3.2278 3.3804 3.5337 3.6877 3.8423 3.9975 4.1533 4.3095 4.6230 4.9375 5.2524 5.5671 5.8809 6.1933 6.5037 6.8114 7.1159 7.4167 7.7133

200 (473.15)

Temperature (8C) (Temperature (K))

2.1226 2.1772 2.2319 2.2867 2.3416 2.3967 2.4519 2.5071 2.5625 2.6180 2.7572 2.8970 3.0373 3.1782 3.3196 3.4615 3.6037 3.7464 3.8894 4.0326 4.3198 4.6075 4.8953 5.1827 5.4694 5.7549 6.0387 6.3204 6.5997 6.8762 7.1495

220 (493.15) 2.0170 2.0683 2.1196 2.1711 2.2227 2.2743 2.3260 2.3778 2.4297 2.4816 2.6117 2.7423 2.8732 3.0046 3.1362 3.2681 3.4004 3.5328 3.6654 3.7982 4.0641 4.3302 4.5962 4.8617 5.1264 5.3901 5.6523 5.9128 6.1712 6.4274 6.6810

240 (513.15) 1.9232 1.9717 2.0202 2.0688 2.1174 2.1661 2.2149 2.2637 2.3126 2.3615 2.4840 2.6067 2.7298 2.8530 2.9765 3.1001 3.2239 3.3479 3.4719 3.5960 3.8443 4.0926 4.3405 4.5879 4.8345 5.0801 5.3244 5.5672 5.8082 6.0473 6.2842

260 (533.15) 1.8391 1.8851 1.9312 1.9773 2.0234 2.0696 2.1158 2.1620 2.2083 2.2546 2.3704 2.4865 2.6027 2.7191 2.8356 2.9522 3.0688 3.1855 3.3023 3.4190 3.6525 3.8857 4.1184 4.3506 4.5819 4.8123 5.0414 5.2692 5.4955 5.7200 5.9427

280 (553.15) 1.7632 1.8070 1.8509 1.8947 1.9387 1.9826 2.0265 2.0705 2.1145 2.1585 2.2686 2.3789 2.4892 2.5995 2.7100 2.8204 2.9309 3.0414 3.1518 3.2623 3.4829 3.7032 3.9230 4.1421 4.3604 4.5777 4.7938 5.0088 5.2223 5.4343 5.6446

300 (573.15)

1.6941 1.7360 1.7779 1.8198 1.8617 1.9037 1.9457 1.9876 2.0296 2.0716 2.1766 2.2817 2.3868 2.4919 2.5970 2.7021 2.8071 2.9122 3.0171 3.1220 3.3316 3.5406 3.7491 3.9569 4.1638 4.3698 4.5747 4.7784 4.9809 5.1819 5.3815

320 (593.15)

850 Solubility in Supercritical Carbon Dioxide

CAT4240—Appendix A—2/11/2006—19:55—SRIDHAR—15608—XML MODEL C – pp. 835–854

270 280 290 300 320 340 360 380 400 420 440 460 480 500 550 600 650 700 750 800 850 900 950 1000 1100 1200 1300 1400 1500 1600 1700 1800 1900 2000

10.789 11.146 11.488 11.816 12.428 12.988 13.502 13.973 14.408 14.811 15.186 15.535 15.862 16.169 16.861 17.467 18.004 18.487 18.925 19.326 19.696 20.04 20.36 20.661 21.212 21.708 22.159 22.573 22.956 23.312 23.646 23.959 24.255 24.536

10.173 10.521 10.856 11.179 11.788 12.351 12.87 13.35 13.795 14.208 14.593 14.954 15.291 15.609 16.327 16.955 17.513 18.014 18.469 18.885 19.268 19.623 19.954 20.265 20.833 21.344 21.808 22.233 22.626 22.992 23.333 23.655 23.958 24.245

9.6303 9.9665 10.292 10.608 11.208 11.766 12.286 12.77 13.22 13.64 14.033 14.401 14.747 15.073 15.812 16.461 17.038 17.555 18.025 18.454 18.85 19.216 19.558 19.878 20.463 20.987 21.464 21.9 22.303 22.677 23.027 23.356 23.666 23.959

9.1508 9.4745 9.7896 10.096 10.682 11.232 11.748 12.231 12.683 13.107 13.505 13.879 14.231 14.563 15.319 15.985 16.577 17.11 17.594 18.036 18.442 18.82 19.171 19.499 20.1 20.639 21.127 21.574 21.986 22.369 22.727 23.062 23.379 23.678 8.7254 9.0365 9.3403 9.6368 10.207 10.746 11.255 11.734 12.185 12.609 13.009 13.386 13.742 14.079 14.848 15.527 16.133 16.679 17.175 17.629 18.046 18.433 18.794 19.131 19.746 20.298 20.797 21.254 21.676 22.067 22.432 22.775 23.097 23.403 8.3459 8.6447 8.9374 9.2238 9.7768 10.303 10.802 11.275 11.722 12.144 12.544 12.922 13.281 13.621 14.398 15.088 15.706 16.263 16.77 17.234 17.661 18.057 18.426 18.771 19.401 19.965 20.475 20.942 21.372 21.771 22.143 22.493 22.822 23.133

8.0054 8.2925 8.5744 8.8509 9.3866 9.8988 10.387 10.852 11.293 11.712 12.11 12.488 12.846 13.188 13.971 14.669 15.296 15.862 16.379 16.852 17.288 17.692 18.069 18.421 19.064 19.639 20.16 20.636 21.075 21.481 21.861 22.216 22.551 22.867

7.4193 7.6853 7.9473 8.2051 8.7075 9.1913 9.6560 10.102 10.528 10.936 11.326 11.698 12.054 12.394 13.181 13.887 14.525 15.106 15.636 16.124 16.575 16.993 17.384 17.749 18.416 19.012 19.552 20.045 20.499 20.92 21.312 21.68 22.026 22.352 6.9318 7.1796 7.4242 7.6654 8.1372 8.5939 9.0351 9.4605 9.8700 10.264 10.642 11.006 11.355 11.69 12.47 13.178 13.821 14.409 14.948 15.446 15.908 16.337 16.738 17.114 17.801 18.416 18.972 19.481 19.949 20.382 20.786 21.165 21.521 21.857 6.5188 6.7509 6.9804 7.2070 7.6514 8.0834 8.5023 8.9079 9.3002 9.6790 10.045 10.397 10.737 11.065 11.834 12.535 13.178 13.768 14.313 14.817 15.285 15.722 16.131 16.515 17.219 17.849 18.421 18.942 19.423 19.868 20.282 20.671 21.036 21.381 6.1633 6.3818 6.5981 6.8119 7.2321 7.6416 8.0401 8.4272 8.8027 9.1666 9.5191 9.8602 10.19 10.509 11.262 11.954 12.592 13.181 13.726 14.233 14.706 15.148 15.562 15.952 16.668 17.312 17.895 18.429 18.92 19.375 19.8 20.197 20.571 20.924

5.8532 6.0598 6.2645 6.4671 6.8658 7.2552 7.6350 8.0049 8.3647 8.7144 9.0540 9.3835 9.7032 10.013 10.748 11.427 12.057 12.642 13.186 13.693 14.167 14.611 15.029 15.424 16.149 16.802 17.396 17.939 18.44 18.905 19.337 19.743 20.124 20.484

CAT4240—Appendix A—2/11/2006—19:55—SRIDHAR—15608—XML MODEL C – pp. 835–854

(continued )

5.5794 5.7757 5.9702 6.1629 6.5424 6.9138 7.2767 7.6308 7.9761 8.3123 8.6396 8.9579 9.2674 9.5682 10.284 10.949 11.569 12.147 12.687 13.192 13.666 14.111 14.531 14.927 15.659 16.32 16.922 17.473 17.982 18.454 18.894 19.307 19.695 20.061

Appendix A 851

1 5 10 15 20 25 30 35 40 45 50 52 54 56 58 60 62 64 66 68 69 70 71 72 73 74 75 76 77 78 79 80 82

P (bar)

0.0196 0.0982 0.1966 0.2952 0.3940 0.4930 0.5921 0.6914 0.7909 0.8905 0.9902 1.0301 1.0701 1.1101 1.1500 1.1900 1.2301 1.2701 1.3101 1.3502 1.3702 1.3902 1.4103 1.4303 1.4504 1.4704 1.4905 1.5105 1.5306 1.5506 1.5707 1.5908 1.6309

340 (613.15)

0.0190 0.0951 0.1903 0.2856 0.3811 0.4768 0.5725 0.6683 0.7643 0.8603 0.9564 0.9949 1.0334 1.0718 1.1103 1.1488 1.1874 1.2259 1.2644 1.3029 1.3222 1.3415 1.3607 1.3800 1.3993 1.4186 1.4378 1.4571 1.4764 1.4957 1.5150 1.5342 1.5728

360 (633.15)

TABLE A.3—Continued

0.0184 0.0921 0.1844 0.2767 0.3691 0.4616 0.5542 0.6468 0.7395 0.8322 0.9250 0.9621 0.9993 1.0364 1.0735 1.1106 1.1478 1.1849 1.2221 1.2592 1.2778 1.2963 1.3149 1.3335 1.3520 1.3706 1.3892 1.4077 1.4263 1.4449 1.4634 1.4820 1.5191

380 (653.15) 0.0179 0.0894 0.1788 0.2683 0.3579 0.4474 0.5371 0.6267 0.7164 0.8061 0.8958 0.9316 0.9675 1.0034 1.0392 1.0751 1.1110 1.1468 1.1827 1.2185 1.2365 1.2544 1.2723 1.2902 1.3082 1.3261 1.3440 1.3619 1.3798 1.3977 1.4156 1.4336 1.4694

400 (673.15) 0.0166 0.0832 0.1663 0.2494 0.3326 0.4157 0.4987 0.5817 0.6647 0.7476 0.8305 0.8636 0.8968 0.9299 0.9630 0.9961 1.0292 1.0622 1.0953 1.1283 1.1448 1.1614 1.1779 1.1944 1.2109 1.2274 1.2439 1.2604 1.2769 1.2934 1.3098 1.3263 1.3593

450 (723.15) 0.0156 0.0778 0.1555 0.2331 0.3107 0.3882 0.4656 0.5430 0.6203 0.6975 0.7746 0.8054 0.8362 0.8670 0.8977 0.9285 0.9592 0.9900 1.0207 1.0513 1.0667 1.0820 1.0973 1.1127 1.1280 1.1433 1.1586 1.1739 1.1892 1.2045 1.2198 1.2351 1.2657

500 (773.15) 0.0146 0.0730 0.1460 0.2188 0.2915 0.3642 0.4368 0.5092 0.5816 0.6538 0.7260 0.7548 0.7836 0.8124 0.8412 0.8699 0.8987 0.9274 0.9561 0.9847 0.9991 1.0134 1.0277 1.0420 1.0563 1.0706 1.0849 1.0992 1.1135 1.1278 1.1421 1.1564 1.1849

550 (823.15)

Temperature (8C) (Temperature (K))

0.0138 0.0688 0.1375 0.2062 0.2747 0.3431 0.4114 0.4795 0.5476 0.6155 0.6833 0.7104 0.7375 0.7645 0.7916 0.8186 0.8456 0.8726 0.8995 0.9264 0.9399 0.9533 0.9668 0.9802 0.9937 1.0071 1.0205 1.0339 1.0474 1.0608 1.0742 1.0876 1.1143

600 (873.15) 0.0130 0.0651 0.1301 0.1949 0.2597 0.3243 0.3888 0.4532 0.5174 0.5816 0.6456 0.6711 0.6967 0.7222 0.7477 0.7732 0.7987 0.8241 0.8495 0.8749 0.8876 0.9003 0.9130 0.9257 0.9383 0.9510 0.9637 0.9763 0.9890 1.0016 1.0142 1.0269 1.0521

650 (923.15) 0.0124 0.0617 0.1234 0.1849 0.2462 0.3075 0.3686 0.4296 0.4905 0.5513 0.6119 0.6361 0.6603 0.6845 0.7086 0.7327 0.7568 0.7809 0.8050 0.8290 0.8411 0.8531 0.8651 0.8771 0.8891 0.9011 0.9130 0.9250 0.9370 0.9490 0.9609 0.9729 0.9968

700 (973.15) 0.0118 0.0587 0.1173 0.1758 0.2341 0.2924 0.3505 0.4084 0.4663 0.5240 0.5816 0.6046 0.6276 0.6506 0.6735 0.6964 0.7193 0.7422 0.7650 0.7879 0.7993 0.8107 0.8221 0.8335 0.8449 0.8563 0.8676 0.8790 0.8904 0.9018 0.9131 0.9245 0.9472

750 (1023.15)

0.0112 0.0560 0.1118 0.1676 0.2232 0.2787 0.3340 0.3893 0.4444 0.4994 0.5543 0.5762 0.5981 0.6199 0.6418 0.6636 0.6854 0.7072 0.7290 0.7507 0.7616 0.7725 0.7833 0.7942 0.8050 0.8159 0.8267 0.8375 0.8484 0.8592 0.8700 0.8808 0.9024

800 (1073.15)

852 Solubility in Supercritical Carbon Dioxide

CAT4240—Appendix A—2/11/2006—19:56—SRIDHAR—15608—XML MODEL C – pp. 835–854

84 86 88 90 92 94 96 98 100 105 110 115 120 125 130 135 140 145 150 160 170 180 190 200 210 220 230 240 250 260 270 280 290 300 320 340 360 380

1.6711 1.7112 1.7514 1.7915 1.8317 1.8719 1.9120 1.9522 1.9924 2.0929 2.1933 2.2938 2.3942 2.4946 2.5949 2.6952 2.7954 2.8955 2.9956 3.1953 3.3945 3.5930 3.7908 3.9878 4.1839 4.3789 4.5728 4.7655 4.9569 5.1469 5.3355 5.5226 5.7080 5.8919 6.2543 6.6094 6.9570 7.2967

1.6114 1.6499 1.6885 1.7271 1.7656 1.8042 1.8427 1.8813 1.9198 2.0162 2.1125 2.2088 2.3050 2.4012 2.4973 2.5933 2.6892 2.7850 2.8807 3.0717 3.2621 3.4518 3.6408 3.8289 4.0162 4.2024 4.3876 4.5717 4.7545 4.9361 5.1163 5.2952 5.4726 5.6484 5.9955 6.3359 6.6695 6.9961 1.5563 1.5934 1.6305 1.6676 1.7047 1.7418 1.7789 1.8160 1.8530 1.9457 2.0383 2.1308 2.2232 2.3156 2.4078 2.5000 2.5920 2.6839 2.7757 2.9589 3.1414 3.3232 3.5043 3.6845 3.8639 4.0423 4.2197 4.3960 4.5712 4.7452 4.9180 5.0894 5.2595 5.4282 5.7614 6.0885 6.4094 6.7239

1.5052 1.5410 1.5768 1.6125 1.6483 1.6841 1.7198 1.7555 1.7913 1.8805 1.9697 2.0588 2.1478 2.2367 2.3254 2.4141 2.5026 2.5910 2.6793 2.8553 3.0307 3.2054 3.3794 3.5525 3.7248 3.8961 4.0665 4.2358 4.4041 4.5713 4.7372 4.9020 5.0655 5.2278 5.5483 5.8633 6.1725 6.4759 1.3922 1.4251 1.4580 1.4909 1.5238 1.5567 1.5895 1.6223 1.6551 1.7371 1.8189 1.9006 1.9821 2.0636 2.1449 2.2261 2.3071 2.3879 2.4687 2.6296 2.7899 2.9494 3.1082 3.2662 3.4234 3.5798 3.7352 3.8898 4.0434 4.1960 4.3475 4.4981 4.6476 4.7960 5.0894 5.3783 5.6623 5.9416 1.2962 1.3267 1.3572 1.3877 1.4182 1.4487 1.4791 1.5095 1.5399 1.6157 1.6915 1.7671 1.8426 1.9179 1.9931 2.0681 2.1430 2.2177 2.2922 2.4409 2.5888 2.7360 2.8826 3.0283 3.1733 3.3175 3.4609 3.6035 3.7451 3.8860 4.0259 4.1649 4.3029 4.4401 4.7114 4.9787 5.2420 5.5012 1.2134 1.2419 1.2704 1.2988 1.3272 1.3557 1.3840 1.4124 1.4407 1.5115 1.5821 1.6526 1.7229 1.7931 1.8631 1.9330 2.0027 2.0723 2.1417 2.2800 2.4177 2.5547 2.6910 2.8265 2.9614 3.0955 3.2289 3.3615 3.4933 3.6243 3.7545 3.8839 4.0124 4.1401 4.3930 4.6423 4.8882 5.1304

1.1411 1.1678 1.1946 1.2213 1.2479 1.2746 1.3012 1.3278 1.3544 1.4208 1.4870 1.5530 1.6190 1.6847 1.7504 1.8158 1.8812 1.9463 2.0113 2.1409 2.2698 2.3981 2.5257 2.6526 2.7789 2.9044 3.0293 3.1534 3.2769 3.3996 3.5215 3.6427 3.7632 3.8829 4.1201 4.3541 4.5849 4.8126 1.0773 1.1026 1.1277 1.1529 1.1780 1.2032 1.2282 1.2533 1.2784 1.3409 1.4033 1.4655 1.5276 1.5896 1.6514 1.7130 1.7745 1.8359 1.8971 2.0191 2.1404 2.2612 2.3813 2.5007 2.6196 2.7378 2.8553 2.9722 3.0884 3.2039 3.3188 3.4330 3.5465 3.6593 3.8828 4.1036 4.3215 4.5365 1.0206 1.0445 1.0683 1.0921 1.1159 1.1397 1.1634 1.1871 1.2108 1.2700 1.3290 1.3879 1.4466 1.5052 1.5636 1.6220 1.6801 1.7381 1.7960 1.9113 2.0261 2.1402 2.2538 2.3667 2.4791 2.5908 2.7020 2.8125 2.9224 3.0317 3.1404 3.2484 3.3558 3.4626 3.6743 3.8834 4.0899 4.2938

0.9698 0.9925 1.0151 1.0377 1.0603 1.0828 1.1054 1.1279 1.1504 1.2065 1.2626 1.3184 1.3742 1.4298 1.4853 1.5406 1.5958 1.6509 1.7058 1.8152 1.9241 2.0324 2.1402 2.2474 2.3540 2.4601 2.5656 2.6705 2.7748 2.8786 2.9818 3.0844 3.1864 3.2879 3.4890 3.6878 3.8843 4.0784

CAT4240—Appendix A—2/11/2006—19:57—SRIDHAR—15608—XML MODEL C – pp. 835–854

(continued)

0.9240 0.9456 0.9671 0.9886 1.0101 1.0316 1.0531 1.0745 1.0959 1.1494 1.2027 1.2559 1.3090 1.3620 1.4148 1.4674 1.5200 1.5724 1.6247 1.7289 1.8325 1.9357 2.0382 2.1403 2.2418 2.3428 2.4433 2.5432 2.6426 2.7414 2.8398 2.9375 3.0348 3.1315 3.3232 3.5128 3.7003 3.8855

Appendix A 853

CAT4240—Appendix A—2/11/2006—19:57—SRIDHAR—15608—XML MODEL C – pp. 835–854 7.0318 7.3331 7.6278 7.9158 8.1972 8.4720 9.1312 9.7519 10.336 10.887 11.407 11.897 12.361 12.801 13.218 13.614 14.35 15.021 15.636 16.203 16.729 17.217 17.674 18.103 18.507 18.889

7.3155 7.6276 7.9324 8.2299 8.5201 8.8033 9.4807 10.116 10.713 11.274 11.801 12.297 12.766 13.208 13.627 14.024 14.761 15.43 16.043 16.606 17.127 17.611 18.064 18.488 18.887 19.265

7.6285 7.9522 8.2679 8.5755 8.8751 9.1670 9.8632 10.514 11.123 11.692 12.226 12.728 13.199 13.644 14.064 14.461 15.197 15.863 16.471 17.029 17.545 18.023 18.47 18.889 19.283 19.655

400 420 440 460 480 500 550 600 650 700 750 800 850 900 950 1000 1100 1200 1300 1400 1500 1600 1700 1800 1900 2000

450 (723.15) 6.2158 6.4851 6.7493 7.0085 7.2627 7.5118 8.1131 8.6844 9.2272 9.7429 10.233 10.7 11.144 11.568 11.973 12.36 13.084 13.751 14.366 14.937 15.47 15.968 16.435 16.874 17.29 17.683

400 (673.15) 6.7733 7.0646 7.3498 7.6289 7.9019 8.1689 8.8105 9.4165 9.9888 10.53 11.041 11.525 11.984 12.42 12.834 13.228 13.962 14.633 15.25 15.819 16.348 16.841 17.301 17.734 18.142 18.528 5.7562 6.0069 6.2534 6.4956 6.7335 6.9671 7.5328 8.0729 8.5882 9.0801 9.5497 9.9984 10.428 10.838 11.232 11.609 12.319 12.976 13.586 14.154 14.685 15.184 15.654 16.097 16.516 16.914

500 (773.15) 600 (873.15) 5.0371 5.2584 5.4764 5.6911 5.9026 6.1109 6.6175 7.1045 7.5722 8.0216 8.4534 8.8684 9.2675 9.6516 10.021 10.378 11.054 11.684 12.274 12.829 13.35 13.843 14.309 14.751 15.171 15.571

550 (823.15) 5.3690 5.6039 5.8351 6.0626 6.2864 6.5066 7.0410 7.5530 8.0434 8.5131 8.9631 9.3945 9.8083 10.206 10.587 10.954 11.647 12.292 12.893 13.455 13.983 14.479 14.948 15.392 15.813 16.213

Temperature (8C) (Temperature (K))

4.7487 4.9580 5.1644 5.3680 5.5686 5.7664 6.2483 6.7127 7.1599 7.5907 8.0055 8.4052 8.7905 9.1620 9.5205 9.8667 10.525 11.141 11.719 12.264 12.779 13.265 13.727 14.166 14.584 14.983

650 (923.15) 4.4952 4.6939 4.8901 5.0837 5.2747 5.4630 5.9228 6.3668 6.7954 7.2090 7.6083 7.9937 8.3659 8.7256 9.0732 9.4095 10.05 10.652 11.218 11.753 12.259 12.74 13.196 13.631 14.045 14.442

700 (973.15) 4.2701 4.4595 4.6465 4.8312 5.0135 5.1935 5.6332 6.0587 6.4703 6.8682 7.2530 7.6252 7.9852 8.3336 8.6709 8.9977 9.6216 10.209 10.764 11.288 11.786 12.259 12.709 13.139 13.549 13.943

750 (1023.15)

4.0686 4.2496 4.4284 4.6050 4.7795 4.9519 5.3736 5.7822 6.1781 6.5615 6.9329 7.2927 7.6413 7.9792 8.3068 8.6245 9.2323 9.8060 10.349 10.863 11.352 11.817 12.261 12.686 13.092 13.481

800 (1073.15)

Note: Density is given in moles/liter. The densities as well as the saturation properties of carbon dioxide were obtained from Chemistry Webbook, NIST (http://webbook.nist.gov/chemistry/ﬂuid/, July 2005).

380 (653.15)

360 (633.15)

340 (613.15)

P (bar)

TABLE A.3 —Continued

854 Solubility in Supercritical Carbon Dioxide

Appendix B List of Solutes by Molecular Formula Formula

MW

AsHCuO4 CHI3

203.47 393.73

C2Cl6

236.74

C2H3N

41.05

C2H4O2 C2H5NO2

60.05 75.07

C2H6O2

62.07

C3H6N6O6

222.12

C3H6O C3H8O

58.08 60.10

C3H8O2

76.09

C3H8O3

92.09

C4H10O

74.12

C4H3ClN2

114.53

C4H3FN2O2

130.08

C4H4N2O

96.09

C4H4N2O2

112.09

C4H4N2S

112.15

Solutes Copper(II) hydrogen arsenate Iodoform Triiodomethane Hexachloroethane Perchloroethane Acetonitrile Methyl cyanide Acetic acid 2-Aminoacetic acid Glycine 1,2-Ethanediol Ethylene glycol Cyclotrimethylenetrinitramine RDX 1,3,5-Trinitrohexahydro-s-triazine Acetone 1-Propanol 2-Propanol 1,2-Propanediol Propylene glycol Glycerin Glycerol 1,2,3-Propanetriol 1-Butanol n-Butanol Butyl alcohol 2-Chloropyrimidine 2-Chloro-1,3-pyrimidine 5-Fluoro-2,4-pyrimidinedione 5-Fluorouracil 4-Hydroxypyrimidine 4-Pyrimidone 4(1H)-Pyrimidinone 2,4-Pyrimidinedione Uracil 2-Mercaptopyrimidine

Data Table No. C-190 T-68 T-68 H-16 H-16 A-10 A-10 A-7 G-8 G-8 E-17 E-17 C-215 C-215 C-215 A-8, A-9 P-119 P-120 P-118 P-118 G-6, G-7 G-6, G-7 G-6, G-7 B-69 B-68–B-70 B-68, B-69 C-63 C-63 F-42 F-42 H-90 H-90 H-90 U-3 U-3 M-10 (continued)

855

CAT4240—APPENDIX B —2/11/2006—14:21—SRIDHAR—XML MODEL C – pp. 855–890

856

Solubility in Supercritical Carbon Dioxide

Formula

MW

C4H5N3

95.10

C4H6N2S

114.17

C4H6O3

90.08

C5H4F6NNaS2

N/A

C5H4N2O2

124.10

C5H5ClMoO2

228.48

C5H7LiO2

106.05

C5H10NNaS2 C5H10O5

N/A 150.13

C5H11NS2$C4H11N

222.41

C6Cl6

284.78

C6HCl5O C6H2Cl4O C6H3N3O7

266.34 231.89 229.10

C6H4Cl2 C6H4Cl2O C6H4N2O5

147.00 163.00 184.11

C6H4O2

108.09

C6H5Br C6H5Cl C6H5Cl2N

157.01 112.56 162.02

C6H5ClO

128.56

C6H5CoI2O

405.85

Solutes Pyrimidine-2-thiol 2-Pyrimidinethione 2-Aminopyrazine Pyrazinamine Methimazole 1-Methylimidazole-2-thiol 1-Methyl-4-imidazoline-2-thione 2-Hydroxypropanoic acid Lactic acid Sodium bis(triﬂuoroethyl)dithiocarbamate 2-Carboxypyrazine Pyrazine-2-carboxylic acid 2-Pyrazinoic acid Chloro(h5-cyclopentadienyl)dioxomolybdenum Bis(2,4-pentanedionato)lithium Li(acac) Lithium acetylacetonate Sodium diethyldithiocarbamate D-Xylose (C)-Xylose Diethylamine diethyldithiocarbamate Diethylammonium diethyldithiocarbamate N,N-Diethyldithiocarbamic acid diethylamine salt BHC Hexachlorobenzene Perchlorobenzene Pentachlorophenol 2,3,4,5-Tetrachlorophenol Picric acid 2,4,6-Trinitrophenol 1,2-Dichlorobenzene 2,4-Dichlorophenol 2,4-Dinitrophenol 2,5-Dinitrophenol 1,4-Benzoquinone p-Benzoquinone Quinone p-Quinone Bromobenzene Chlorobenzene 3,4-Dichloraniline 3,4-Dichlorobenzenamine 4-Chlorophenol p-Chlorophenol Carbonyldiiodo(h5-Cyclopentadienyl)cobalt

Data Table No. M-10 M-10 A-34 A-34 M-16 M-16 M-16 L-1 L-1 M-12, M-13 P-128 P-128 P-128 C-213 L-27 L-27 L-27 M-12, M-13 X-4 X-4 D-40 D-40 D-40 H-8–H-10 H-8–H-10 H-8–H-10 P-26–P-30 T-16 P-84 P-84 D-21 D-31 D-77 D-78 Q-2, Q-3 Q-2, Q-3 Q-2, Q-3 H-39, Q-2, Q-3 B-67 C-53 P-43 P-43 C-61 C-61 C-213

(continued)

CAT4240—APPENDIX B —2/11/2006—14:21—SRIDHAR—XML MODEL C – pp. 855–890

Appendix B List of Solutes by Molecular Formula

Formula

MW

C6H5NO2

123.11

C6H5NO3

139.11

C6H6Cl6

290.83

C6H6O C6H6O2

94.11 110.11

C6H8O6

176.12

C6H10O C6H10O4PdS2

98.14 316.69

C6H12O C6H12O2

100.16 116.16

C6H12O3

132.16

C6H12O6

180.16

C6H13NO2

131.17

C6H14O

102.17

C6H14O4

150.17

857

Solutes 3-Carboxypyridine Nicotinic acid 3-Pyridinecarboxylic acid 3-Nitrophenol 4-Nitrophenol m-Nitrophenol p-Nitrophenol g-BHC g-1,2,3,4,5,6-Hexachlorocyclohexane Lindane Phenol 1,2-Benzenediol 1,3-Benzenediol 1,4-Benzenediol Catechol 1,3-Dihydroxybenzene o-Dihydroxybenzene m-Dihydroxybenzene p-Dihydroxybenzene Hydroquinone Pyrocatechol Resorcinol Ascorbic acid Vitamin C Cyclohexanol Bis(methylthioglycolato)palladium Palladium bis(methylthioglycolate) Pd(MTG)2 Cyclohexanone Butyl acetate Caproic acid 1-Hexanoic acid Hexanoic acid 2-Hydroxyhexanoic acid (G)-2-Hydroxycaproic acid Dextrose D-Fructose D-(K)-Fructose D-Glucose D-(C)-Glucose D-(K)-Levulose (S)-2-Amino-4-methylpentanoic acid L-Leucine 4-Methyl-L-norvaline Diethyl methyl carbinol 1-Hexanol 3-Hexanol n-Hexyl alcohol 3-Methyl-3-pentanol 2,2 0 -(Ethylenedioxy)diethanol

Data Table No. N-67, N-68, N-69, N-70, N-71 N-67–N-71 N-67–N-71 N-80 N-81 N-80 N-81 L-23 L-23 L-23 N-34, P-75, P-76 D-50, P-138, P-139 D-50, R-3 D-50, H-34–H-38 P-138, P-139 R-3 D-50 D-50 D-50 D-50, H-34–H-39 D-50, P138, P-139 D-50, R-3 A-70 A-70 C-210 P-2 P-2 P-2 C-211 B-71, B-72 H-26, H-27 H-26, H-27 H-26, H-27 H-83 H-83 G-4, G-5 F-45 F-45 G-4, G-5 G-4, G-5 F-45 L-8 L-8 L-8 M-51 H-28 H-29 H-28 M-51 T-63, T-64 (continued)

CAT4240—APPENDIX B —2/11/2006—14:21—SRIDHAR—XML MODEL C – pp. 855–890

858

Solubility in Supercritical Carbon Dioxide

Formula

MW

C6H15O4P C6MoO6

182.15 264.00

C7H5N

103.12

C7H5N3O6

227.13

C7H6O

106.12

C7H6O2 C7H6O3

122.12 138.12

C7H6O4

154.12

C7H7Cl C7H7NO2

126.58 137.14

C7H7NO3

153.14

C7H8N4O2

180.16

C7H8O

108.14

Solutes Triethylene glycol Triglycol Triethyl phosphate Hexacarbonylmolybdenum Molybdenum hexacarbonyl Benzenecarbonitrile Benzonitrile Cyanobenzene TNT Trinitrotoluene 2,4,6-Trinitrotoluene Benzaldehyde Benzoic aldehyde Benzoic acid Catechaldehyde 3,4-Dihydroxybenzaldehyde 2-Hydroxybenzoic acid 3-Hydroxybenzoic acid 4-Hydroxybenzoic acid o-Hydroxybenzoic acid m-Hydroxybenzoic acid p-Hydroxybenzoic acid Protocatechualdehyde Salicylic acid 2,5-Dihydroxybenzoic acid 3,4-Dihydroxybenzoic acid Gentisic acid 5-Hydroxysalicylic acid Protocatechuic acid 2-Chloro-1-methylbenzene 2-Aminobenzoic acid Anthranilic acid 2-Carboxyaniline 1-Methyl-3-nitrobenzene 3-Nitrotoluene 2-Methoxynitrobenzene 2-Nitroanisole 3,7-Dihydro-3,7-dimethyl-1H-purine2,6-dione 1,3-Dimethylxanthine 3,7-Dimethylxanthine Theobromine Theophylline Anisole Benzenemethanol Benzyl alcohol 4-Cresol p-Cresol Methoxybenzene Methyl phenyl ether

Data Table No. T-63, T-64 T-63, T-64 U-4 M-58 M-58 B-28 B-28 B-28 T-77, T-78 T-77, T-78 T-77, T-78 B-9, B-10 B-9 B-13–B-26, D-8, N-24, P-67 P-126 P-126 H-50–H-62 H-68–H-72 H-73–H-75 H-50–H-66 H-63, H-64, H-66–H-72 H-65–H-67, H-73–H-75 P-126 A-74, H-50–H-62 G-2 P-127 G-2 G-2 P-127 C-60 A-25–A-27 A-25, A-26 A-25, A-26 N-82 N-82 N-76 N-76 T-30–T-34 T-35–T-38 T-30–T-34 T-30–T-34 T-35–T-38 A-38, A-39 B-30, B-31 B-30, B-31 C-202 C-202 A-38, A-39 A-38 (continued)

CAT4240—APPENDIX B —2/11/2006—14:21—SRIDHAR—XML MODEL C – pp. 855–890

Appendix B List of Solutes by Molecular Formula

Formula

MW

C7H8O2

124.14

C7H12ClN5

201.66

C8Cl4N2

265.91

C8H4O3

148.12

C8H5MnO3

204.06

C8H6Cl2O3

221.04

C8H7N

117.15

C8H7NO4

181.15

C8H8I2O2S

422.02

C8H8O2

136.15

C8H8O3

152.15

859

Solutes 4-Methylphenol 2-Hydroxyanisole 2-Methoxyphenol 2-Chloro-4,6-bis(ethylamino)-1,3,5triazine Simazine Chlorothalonil 2,4,5,6-Tetrachloro-1,3-benzenedicarbonitrile Tetrachloroisophthalonitrile 1,3-Isobenzofurandione 1,3-Phthalandione Phthalic anhydride Cyclopentadienylmanganese tricarbonyl Tricarbonyl(h5-cyclopentadienyl)manganese 2,4-D 2,4-Dichlorophenoxy acetic acid 2,4-Dichlorophenoxy ethanoic acid 2,3-Benzopyrrole 1H-Indole Indole Methyl 2-nitrobenzoate Methyl 3-nitrobenzoate Methyl 4-nitrobenzoate Methyl o-nitrobenzoate Methyl m-nitrobenzoate Methyl p-nitrobenzoate 2-Nitrobenzoic acid methyl ester 3-Nitrobenzoic acid methyl ester 4-Nitrobenzoic acid methyl ester Diiodomethyl p-tolyl sulfone p-Tolyl diiodomethyl sulfone p-Anisaldehyde Benzeneacetic acid 4-Methoxybenzaldehyde 2-Methylbenzoic acid 3-Methylbenzoic acid 4-Methylbenzoic acid Phenylacetic acid Phenylethanoic acid o-Anisic acid m-Anisic acid p-Anisic acid 4-Carbomethoxy phenol 2-Hydroxy-2-phenylacetic acid 4-Hydroxy-3-methoxybenzaldehyde a-Hydroxybenzeneacetic acid 2-Hydroxybenzoic acid methyl ester Mandelic acid

Data Table No. C-202 M-26 M-26 S-4 S-4 T-15 T-15 T-15 P-83 P-83 P-83 C-212 C-212 D-32–D-35, P-43 D-32–D-35, P-43 D-32–D-35 I-3 I-3 I-3 M-43 M-44 M-45 M-43, M-46, M-47 M-44, M-46 M-45, M-47 M-43 M-44 M-45 D-56 D-56 A-35 P-79 A-35 M-34 M-35 M-36 P-79 P-79 M-19 M-20 A-37, M-21 M-53 M-1 V-3 M-1 M-52 M-1 (continued)

CAT4240—APPENDIX B —2/11/2006—14:21—SRIDHAR—XML MODEL C – pp. 855–890

860

Solubility in Supercritical Carbon Dioxide

Formula

MW

C8H8O4

168.15

C8H8O5

184.15

C8H9NO2

151.16

C8H9O2N

151.16

C8H10N4O2

194.19

C8H10O

122.16

C8H10O2

138.16

C8H11N

121.18

C8H13Cl2MoO2Si

336.91

C8H14ClN5

215.68

C8H15N2$BF4

226.02

C8H15N2$F6P

284.18

Solutes 2-Methoxybenzoic acid 3-Methoxybenzoic acid 4-Methoxybenzoic acid Methyl 2-hydroxybenzoate Methyl 4-hydroxybenzoate Methyl salicylate Methylparaben Vanillin 4-Hydroxy-3-methoxybenzoic acid Vanillic acid Gallic acid methyl ester Methyl gallate 3,4,5-Trihydroxybenzoic acid methyl ester Acetaminophen 4 0 -Hydroxyacetanilide N-(4-Hydroxyphenyl)acetamide m-Anisamide p-Anisamide 3-Methoxybenzamide 4-Methoxybenzamide Caffeine 1,3,7-Trimethyl-2,6-dioxopurine 1,3,7-Trimethylxanthine 2,5-Dimethylphenol 2,6-Dimethylphenol 3,4-Dimethylphenol 4-Hydroxy-1,2-dimethylbenzene 2,5-Xylenol 2,6-Xylenol 3,4-Xylenol 1,2-Dimethoxybenzene 1,4-Dimethoxybenzene Hydroquinone dimethyl ether 2-Methoxyanisole 4-Methoxyanisole 2,5-Dimethylaniline 2,5-Dimethylbenzenamine 2,5-Xylidine Chloro(h5-Trimethylsilylcyclopentadienyl)dioxomolybdenum Atrazine 2-Chloro-4-ethylamino-6isopropylamino-1,3,5-triazine 1-Butyl-3-methylimidazolium tetraﬂuoroborate Ionic liquid [bmim][BF4] 1-Butyl-3-methylimidazolium hexaﬂuorophosphate

Data Table No. M-19 M-20 A-37, M-21 M-52 M-53 M-52 M-53 V-3 V-1, V-2 V-1, V-2 M-39 M-39 M-39 A-4–A-6 A-4–A-6 A-4–A-6 M-17 M-18 M-17 M-18 C-3–C-11 C-3–C-11 C-3–C-11 X-1 X-2 X-3 X-3 X-1, N-35 X-2 X-3 D-59 D-60 D-60 D-59 D-60 D-63 D-63 D-63 C-214

A-76–A-78 A-76, A-77, A-78 B-79 B-79 B-77, B-78

(continued)

CAT4240—APPENDIX B —2/11/2006—14:22—SRIDHAR—XML MODEL C – pp. 855–890

Appendix B List of Solutes by Molecular Formula

Formula

MW

C8H16O2

144.21

C8H18

114.23

C8H18O C9H6N2S3

130.23 238.36

C9H6O2

146.14

C9H6O3

162.14

C9H6O4

178.14

C9H7NO

145.16

C9H8O2

148.16

C9H8O3

164.16

C9H8O4

180.16

C9H9N

131.17

C9H9N3O2S2

255.32

C9H9NO

147.17

C9H10Cl2N2O2

249.09

C9H10O3

166.17

861

Solutes Ionic liquid [bmim][PF6] a-Ethylcaproic acid 2-Ethylhexanoic acid 2,3-Dimethylhexane Octane n-Octane 2-Ethyl-1-hexanol 2-(Thiocyanatomethylthio) benzo[d]thiazole 2-(Thiocyanomethylthio)benzothiazole 2H-1-Benzopyran-2-one Coumarin 4-Hydroxychromen-2-one 7-Hydroxychromen-2-one 4-Hydroxycoumarin 7-Hydroxycoumarin Aesculetin 6,7-Dihydroxycoumarin Esculetin 8-Hydroxyquinoline 8-Quinolinol trans-Cinnamic acid trans-3-Phenylacrylic acid (E)-3-Phenyl-2-propenoic acid 2-Coumaric acid 3-Coumaric acid 4-Coumaric acid o-Coumaric acid m-Coumaric acid p-Coumaric acid 2-Hydroxycinnamic acid 3-Hydroxycinnamic acid 4-Hydroxycinnamic acid 2-Acetoxybenzoic acid Acetylsalicylic acid Aspirin Caffeic acid 3,4-Dihydroxybenzeneacrylic acid 3,4-Dihydroxycinnamic acid 3-Methylindole Skatole 2-(Sulfanilylamino)thiazole Sulfathiazole N1-(2-Thiazolyl)sulfanilamide 5-Methoxyindole 5-Methoxy-1H-indole 3-(3,4-Dichlorophenyl)-1-methoxy1-methylurea Linuron Ethyl 4-hydroxybenzoate

Data Table No. B-77, B-78 E-19 E-19, E-20 D-66 O-17 B-70, O-17 E-18, E-20 T-40 T-40 C-200, C-201 C-200, C-201 H-77 H-78, C-79 H-77 H-78, H-79 A-21 A-21 A-21 H-91 H-91 C-160 C-160 C-160 C-192, C-193 C-194, C-195 C-196–C-199 C-192, C-193 C-194, C-195 C-196–C-199 C-192, C-193 C-194, C-195 C-196–C-199 A-13, A-72, A-73 A-13, A-72, A-73 A-13, A-72–A-74 C-2 C-2 C-2 S-5 S-5 S-44, S-45 S-44, S-45 S-44, S-45 M-24 M-24 P-43 P-43 H-76 (continued)

CAT4240—APPENDIX B —2/11/2006—14:22—SRIDHAR—XML MODEL C – pp. 855–890

862

Solubility in Supercritical Carbon Dioxide

Formula

MW

C9H10O5

198.17

C9H11NO2

165.19

C9H12O

136.19

C9H13CoI2OSi

477.82

C9H15O6RhS3

418.31

C9H16ClN5

229.71

C9H17N5O

211.26

C9H17N5S

227.33

C9H20O

144.25

C10H2BaF12O4

551.43

C10H2CoF12O4

473.03

C10H2CuF12O4

C10H2CuF12O4.H2O

C10H2F12NiO4

477.65

495.67

N/A

Solutes 4-Hydroxybenzoic acid ethyl ester o-Methoxyphenylacetic acid m-Methoxyphenylacetic acid p-Methoxyphenylacetic acid Gallic acid 3,5-dimethyl ether 4-Hydroxy-3,5-dimethoxybenzoic acid Syringic acid 4-Aminobenzoic acid ethyl ester (S)-2-Amino-3-phenylpropanonic acid Benzocaine Ethyl 4-aminobenzoate L-Phenylalanine 3-Phenyl-L-alanine Benzenepropanol 3-Phenyl-1-propanol Carbonyldiiodo(h5-Trimethylsilyl cyclopentadienyl)cobalt Rh(MTG)3 Rhodium tris(methylthioglycolate) Tris(methylthioglycolato)rhodium 2-Chloro-4,6-bis(isopropylamino)1,3,5-triazine Propazine Atratone 2-Ethylamino-4-isopropylamino6-methoxy-s-triazine Ametryne 2-Ethylamino-4-isopropylamino6-methylthio-1,3,5-triazine 1-Nonanol Nonyl alcohol Barium bis(hexaﬂuoroacetylacetonate) Bis(1,1,1,5,5,5-hexaﬂuoro2,4-pentanedionato)barium Bis(1,1,1,5,5,5-hexaﬂuoro2,4-pentanedionato)cobalt Cobalt bis(hexaﬂuoroacetylacetonate) Co(hfa)2 Copper bis(hexaﬂuoroacetylacetonate) Bis(1,1,1,6,6,6-hexaﬂuoro pentane2,4-dionato)copper Copper bis(1,1,1,6,6,6-hexaﬂuoroacetylacetonate) Cu(hfa)2 Bis(1,1,1,6,6,6-hexaﬂuoro pentane2,4-dionato)copper hydrate Copper bis(1,1,1,6,6,6-hexaﬂuoroacetylacetonate) hydrate Cu(hfa)2$H2O Nickel bis(hexaﬂuoroacetylacetonate)

Data Table No. H-76 M-27 M-27 M-27 S-46 S-46 S-46 B-11, B-12 P-80 B-11, B-12 B-11, B-12 P-80 P-80 P-81 P-81 C-214 R-7 R-7 R-7 P-121 P-121 A-75 A-75 A-23, A-24 A-23, A-24 N-89 N-89 B-1 B-1 C-167 C-167 C-167 M-13 C-180 C-180 C-180 C-181, C-182 C-181, C-182 C-181, C-182 M-13 (continued)

CAT4240—APPENDIX B —2/11/2006—14:22—SRIDHAR—XML MODEL C – pp. 855–890

Appendix B List of Solutes by Molecular Formula

Formula

863

MW

Solutes

C10H5Cl2F5O2 C10H6Cl2O

323.04 213.06

C10H6O2

158.15

C10H7NO2

173.17

C10H8 C10H8CuF12N2S4

128.17 575.95

C10H8CuF6O4

369.71

Pentaﬂuoropropyl 2,5-dichlorobenzoate 2,4-Dichloro-1-naphthalenol 2,4-Dichloro-1-naphthol 1,4-Naphthalenedione 1,4-Naphthoquinone p-Naphthoquinone C. I. Mordant Brown 2-Nitroso-1-naphthol Naphthalene Copper bis[bis(triﬂuoroethyl)dithiocarbamate] Bis(1,1,1-triﬂuoropentane-2,4-dionato)copper Copper bis(1,1,1-triﬂuoroacetylacetonate) Cu(tfa)2 Mercury bis[bis(triﬂuoroethyl)dithiocarbamate] Nickel bis[bis(triﬂuoroethyl)dithiocarbamate] 1-Naphthalenol 2-Naphthalenol 1-Naphthol 2-Naphthol a-Naphthol b-Naphthol 6-Methyl-2H-1-benzopyran-2-one 7-Methyl-2H-1-benzopyran-2-one 6-Methylcoumarin 7-Methylcoumarin 7-Hydroxy-4-methyl-2H-chromen-2-one 7-Hydroxy-4-methylcoumarin 7-Methoxy-2H-1-benzopyran-2-one 7-Methoxycoumarin Methylumbelliferone 4-Methylumbelliferone 2,5-Dichlorobenzoic acid n-propyl ester Propyl 2,5-dichlorobenzoate Dichlorobis(h5-cyclopentadienyl)titanium Titanocene dichloride Dichlorobis(h5-cyclopentadienyl)zirconium Bis(h5-cyclopentadienyl)iron Ferrocene Iron bis(cyclopentadienide) Ferulic acid 4-Hydroxy-3-methoxycinnamic acid 3-(4-Hydroxy-3-methoxyphenyl)acrylic acid

C10H8F12HgN2S4

713.00

C10H8F12N2NiS4

N/A

C10H8O

144.17

C10H8O2

160.17

C10H8O3

176.17

C10H10Cl2O2

233.09

C10H10Cl2Ti

249.00

C10H10Cl2Zr

292.32

C10H10Fe

186.03

C10H10O4

194.18

Data Table No. P-38 D-30 D-30 N-52–N-54 N-52–N-54 N-52–N-54 C-155 C-155 N-1–N-35, P-71 C-189, M-12, M-13, M-15 C-186 C-186 C-186 M-11, M-13, M-15 M-12, M-13, M-15 N-36, N-37 N-39–N-48 N-36, N-37 N-39–N-48 N-36–N-38 N-38–N-51 M-37 M-38 M-37 M-38 H-86 H-86 M-23 M-23 M-23 H-86 P-123 P-123 T-43 T-43 C-213 F-2–F-5 F-2–F-5 F-2–F-5 F-6–F-8 F-6–F-8 F-6–F-8

(continued)

CAT4240—APPENDIX B —2/11/2006—14:22—SRIDHAR—XML MODEL C – pp. 855–890

864

Solubility in Supercritical Carbon Dioxide

Formula

MW

Solutes

C10H11NO3

193.20

C10H11O3 C10H12

193.20 132.20

C10H12O

148.20

C10H12O2

164.20

C10H12O3

180.20

C10H12O5

212.20

C10H14CoO4

257.15

C10H14CoO4$2H2O

293.18

C10H14CuO4

261.76

C10H14MnO4$2H2O

289.19

4 0 -Acetoxyacetanilide p-Acetoxyacetanilide 4-Acetamidophenyl acetate 1,2,3,4-Tetrahydronaphthalene Tetralin 1,2,3,4-Tetrahydro-1-naphthol a-Tetralol 4-Allyl-2-methoxyphenol Eugenol 2-Methoxy-4-(2-propenyl)phenol 4-Hydroxybenzoic acid propyl ester Propyl 4-hydroxybenzoate Gallic acid propyl ester Propyl gallate 3,4,5-Trihydroxybenzoic acid propyl ester Bis(2,4-pentanedionato)cobalt Co(acac)2 Cobalt bis(acetylacetonate) Bis(2,4-pentanedionato)copper dihydrate Copper bis(acetylacetonate) dihydrate Bis(2,4-pentanedionato)copper Copper bis(acetylacetonate) Cu(acac)2 Bis(2,4-pentanedionato)manganese dihydrate Manganese bis(acetylacetonate) dihydrate Mn(acac)2$2H2O 2-tert-Butylphenol Carvacrol L-Carvone (R)-(K)-Carvone 2-(1,1-Dimethylethyl)phenol 5-Isopropyl-2-methylphenol 5-Isopropyl-o-cresol (R)-(K)-p-Mentha-6,8-dien-2-one 5-Methyl-2-(1-methylethyl)phenol Thymol Bis(2,4-pentanedionato)palladium Palladium bis(acetylacetonate) Pd(acac)2 Bis(2,4-pentanedionato)platinum Platinum bis(acetylacetonate) Bis(2,4-pentanedionato)zinc Zinc bis(acetylacetonate) Zinc bis(2,4-pentanedionate) Adamantane 4-Isopropenyl-1-methyl-1-cyclohexene

C10H14O

150.22

C10H14O4Pd

304.64

C10H14O4Pt

393.29

C10H14O4Zn

263.60

C10H16

136.23

Data Table No. A-11, A-12 A-11, A-12 A-11, A-12 T-25, T-26 T-25, T-26 T-27, T-28 T-27, T-28 E-28 E-28 E-28 P-125 P-125 P-124 P-124 P-124 C-166 C-166 C-166 C-177 C-177 C-173–C-176 C-173–C-176 C-173–C-176 M-2 M-2 M-2 B-80 C-41 C-42 C-42 B-80 C-41 C-41 C-42 T-42 T-42 P-1 P-1 P-1 P-90 P-90 Z-1 Z-1 Z-1 A-19, A-20 L-10–L-16, L-18 (continued)

CAT4240—APPENDIX B —2/11/2006—14:22—SRIDHAR—XML MODEL C – pp. 855–890

Appendix B List of Solutes by Molecular Formula

Formula

C10H16CuN2S4 C10H16HgN2S4 C10H16O

MW

356.04 493.08 152.23

C10H18

138.25

C10H18O

154.25

C10H19N5O

225.29

C10H19N5S

241.36

C10H19NO C10H20CuN2S4 C10H20HgN2S4 C10H20N2NiS4 C10H20N2PdS4 C10H20O

169.27 360.07 497.11 N/A N/A 156.27

C10H22 C10H22O

142.28 158.28

C10H22O2

174.28

865

Solutes (4S)-4-Isopropenyl-1-methyl-1cyclohexene Limonene L-Limonene p-Mentha-1,8-diene (S)-(K)-p-Mentha-1,8-diene 2-Pinene a-Pinene Tricyclo[3.3.1.13,7]decane 2,6,6-Trimethylbicyclo[3.1.1]hept-2-ene Copper pyrrolidinedithiocarbamate Mercury pyrrolidinedithiocarbamate 2-Bornanone Camphor Citral 3,7-Dimethyl-2,6-octadienal Fenchone cis-2-Pinen-4-ol 1,3,3-Trimethyl-2-norbornanone 1,7,7-Trimethylbicyclo[2,2,1]heptan-2-one 1,3,3-Trimethylnorcamphor cis-Verbenol Decahydronaphthalene Decalin Cineole 1,8-Cineole 3,7-Dimethyl-1,6-octadien-3-ol 1,8-Epoxy-p-menthane Linalool 2-Methoxy-4,6-bis(isopropylamino)1,3,5-triazine Prometone 2,4-Bis(isopropylamino)-6-methylthio1,3,5-triazine Prometryne 6-Caprolactam Copper bis(diethyldithiocarbamate) Mercury bis(diethyldithiocarbamate) Nickel bis(diethyldithiocarbamate) Palladium bis(diethyldithiocarbamate) Menthol 5-Methyl-2-(1-methylethyl)cyclohexanol Decane Capric alcohol 1-Decanol Decyl alcohol Decamethylene glycol 1,10-Decanediol

Data Table No. L-17 L-10–L-20 L-17 L-10–L-16 L-17 P-85–P-88 P-85–P-88 A-19, A-20 P-85–P-88 C-189 M-11 C-13 C-13 C-163, C-164, L-19 C-163, C-164, L-19 F-1 V-5 F-1 C-13 F-1 V-5 D-2 D-2 C-158, C-159 C-158, C-159 L-21, L-22 C-158, C-159 L-20–L-22 P-115 P-115 P-116, P-117 P-116, P-117 C-15 C-189, M-12, M-13 M-11, M-13 M-12, M-13 M-14 M-7–M-9 M-7–M-9 D-3–D-6 D-9 D-9 D-9 D-7 D-7, D-8 (continued)

CAT4240—APPENDIX B —2/11/2006—14:22—SRIDHAR—XML MODEL C – pp. 855–890

866

Solubility in Supercritical Carbon Dioxide

Formula

MW

Solutes

C11H7Cl2F5O2 C11H7N

337.07 153.18

C11H8O2

172.18

C11H10

142.20

C11H10O

158.20

C11H11N5

213.24

C11H12Cl2N2O5

323.13

C11H12Cl2O2

247.12

C11H12N2O2

204.23

C11H12N4O2S

264.30

C11H12O2

176.21

Pentaﬂuorobutyl 2,5-dichlorobenzoate 2-Cyanonaphthalene 2-Naphthalenenitrile 2-Naphthonitrile 1-Formyl-2-naphthol 2-Hydroxy-1-naphthaldehyde Menadione 2-Methyl-1,4-naphthoquinone Vitamin K3 1-Methylnaphthalene 2-Methylnaphthalene 2-Methoxynapthalene Methyl-2-naphthyl ether 2,6-Diamino-3-phenylazopyridine Phenazopyridine Chloramphenicol 2,2-Dichloro-N-((1R,2R)-1,3-dihydroxy1-(4-nitrophenyl)propan-2-yl)acetamide Butyl 2,5-dichlorobenzoate 2,5-Dichlorobenzoic acid butyl ester (2S)-2-Amino-3-(1H-indol-3-yl)propanoic acid L-Tryptophan N-(4-Methyl-2-pyrimidyl)sulfanilamide Sulfamerazine 3,4-Dihydro-5-methoxy-1(2H)naphthalenone 3,4-Dihydro-6-methoxy-1(2H)naphthalenone 3,4-Dihydro-7-methoxy-1(2H)naphthalenone 5-Methoxy-1-tetralone 6-Methoxy-1-tetralone 7-Methoxy-1-tetralone Oxacyclododecan-2-one 11-Undecanolactone Undecanolide 1-Undecanol Undecyl alcohol 2,2 0 ,3,4,4 0 ,5,5 0 -Heptachlorobiphenyl PCB 180 2,2 0 ,3,3 0 ,4,4 0 -Hexachlorobiphenyl 2,2 0 ,4,4 0 ,5,5 0 -Hexachlorobiphenyl PCB 128 PCB 153 2,2 0 ,4,5,5 0 -Pentachlorobiphenyl PCB 70 PCB 77 2,3 0 ,4 0 ,5-Tetrachlorobiphenyl

C11H20O2

184.28

C11H24O

172.31

C12H3Cl7

395.32

C12H4Cl6

360.88

C12H5Cl5 C12H6Cl4

326.43 291.99

Data Table No. P-37 C-204 C-204 C-204 H-89 H-89 V-12, V-13 V-12, V-13 V-12, V-13 A-39, B-10, M-40, M-42 N-30, M-40–M-42 M-25 M-25 P-74 P-74 C-52 C-52

B-76 B-76 T-105 T-105 S-41 S-41 M-28 M-29 M-30 M-28, M-32 M-29, M-31 M-30–M-32 U-2 U-2 U-2 U-1 U-1 H-2–H-4 H-2–H-4 H-11, H-12 H-13–H-15 H-11, H-12 H-13–H-15 P-23–P-25 T-11 T-12–T-14 T-11 (continued)

CAT4240—APPENDIX B —2/11/2006—14:22—SRIDHAR—XML MODEL C – pp. 855–890

Appendix B List of Solutes by Molecular Formula

Formula

MW

C12H7Cl3 C12H8Cl2

257.54 223.10

C12H8Cl6O

380.91

C12H8N2

180.21

C12H8O

168.19

C12H8S

184.26

C12H9Cl

188.66

C12H9N

167.21

C12H10

154.21

C12H10N2

182.22

C12H10N2O

198.22

C12H10N2O2

214.22

C12H10N4O2

242.24

C12H11N

169.22

C12H12

156.22

C12H13NO6

267.24

C12H14Cl2FNO4S

358.21

867

Solutes 3,3 0 ,4,4 0 -Tetrachlorobiphenyl 2,4 0 ,5-Trichlorobiphenyl 2,2 0 -Dichlorobiphenyl 4,4 0 -Dichlorobiphenyl 2,2 0 -Dichloro-1,1 0 -biphenyl 4,4 0 -Dichloro-1,1 0 -biphenyl PCB 15 Endrin 1,2,3,4,10,10-Hexachloro-6,7-epoxy1,4,4a,5,6,7,8,8a-octahydro-endo1,4-endo-5,8-dimethanonaphthalene 9,10-Diazaanthracene 4,5-Diazaphenanthrene Dibenzopyrazine 1,10-Phenanthroline Phenazine Dibenzofuran Diphenylene oxide Dibenzothiophene Diphenylene sulﬁde 9-Thiaﬂuorene 2-Chlorobiphenyl 4-Chlorobiphenyl 9-Azaﬂuorene Carbazole Dibenzopyrrole Acenaphthene Biphenyl 1,1 0 -Biphenyl 1,2-Dihydroacenaphthylene Azobenzene Diphenyldiazene C. I. Solvent Yellow 7 p-Hydroxyazobenzene 4-(Phenylazo)phenol 2-Nitrodiphenylamine 2-Nitro-N-phenylaniline 4-Amino-4 0 -nitroazobenzene C. I. Disperse Orange 3 4-(4-Nitrophenylazo)aniline Diphenylamine N-Phenylaniline N-Phenylbenzenamine 2,3-Dimethylnaphthalene 2,6-Dimethylnaphthalene 2,7-Dimethylnaphthalene N-Benzyloxycarbonyl-DL-aspartic acid N-Carbobenzoxy aspartic acid Aquafen

Data Table No. T-12–T-14 T-58–T-60 D-22–D-24 D-25–D-28 D-22–D-24 D-25–D-28 D-25–D-28 E-9 E-9

P-73 P-72 P-73 P-72 P-73 D-17 D-17 D-18 D-18 D-18 C-54–C-56 C-57–C-59 C-22, C-23 A-61, A-63, C-22, C-23, P-68 C-22, C-23 A-1–A-3 B-35–B-38, N-25, N-26 B-36, B-38 A-1, A-2 A-80, A-81 A-80, A-81 H-48, H-49 H-48, H-49 H-48, H-49 N-79 N-79 C-113–C-115 C-113–C-115 C-114, C-115 D-86–D-88 D-86–D-88 D-86–D-88 D-67–D-69, N-27, P-69 D-69–D-74, N-28, P-70 D-74, D-75 C-24 C-24 F-32

(continued)

CAT4240—APPENDIX B —2/11/2006—14:23—SRIDHAR—XML MODEL C – pp. 855–890

868

Solubility in Supercritical Carbon Dioxide

Formula

MW

C12H14N4O2S

278.33

C12H14N4O4S

310.33

C12H14O4

222.24

C12H15Cl2NO5S

356.22

C12H18

162.27

C12H18Br6 C12H22 C12H22O11

641.73 166.30 342.30

C12H24O2

200.32

C12H26 C12H27O4P

170.33 266.31

C13H8O

180.20

C13H8O2S

228.27

C13H8O3

212.20

C13H8O4

228.20

C13H8O5

244.20

C13H8OS

212.27

C13H9N

179.22

C13H10

166.22

Solutes 2,2-Dichloro-N-[(1S,2R)-1(ﬂuoromethyl)-2-hydroxy-2[4-(methyl sulfonyl)phenyl]ethyl]acetamide Florfenicol N1-(4,6-Dimethyl-2-pyrimidinyl)sulfanilamide Sulfamethazine 2,6-Dimethoxy-4-sulfanilamidopyrimidine 2,4-Dimethoxy-6-sulfonylamido1,3-diazine Sulfadimethoxine Diethyl 1,2-benzenedicarboxylate Diethyl phthalate Phthalic acid diethyl ester 2,2-Dichloro-N-[2-hydroxy1-(hydroxymethyl)-2-[4(methylsulfonyl) phenyl]ethyl]acetamide Thiamphenicol 1,5,9-Cyclododecatriene Hexamethylbenzene Hexabromocyclododecane Cyclododecene Saccharose Sucrose (C)-Sucrose Dodecanoic acid Lauric acid Dodecane Phosphoric acid tributyl ester Tributyl Phosphate 9-Fluorenone Fluoren-9-one 1-Hydroxy-9H-thioxanthen-9-one 1-Hydroxythioxanthone 1-Hydroxy-9H-xanthen-9-one 1-Hydroxyxanthone 1,6-Dihydroxyxanthen-9-one 1,6-Dihydroxyxanthone 1,5,6-Trihydroxyxanthen-9-one 1,5,6-Trihydroxyxanthone Thioxanthen-9-one Thioxanthone 9-Thioxanthone Acridine 9-Azaanthracene 2,3-Benzoquinoline Fluorene

Data Table No. F-32

F-32 S-42, S-43 S-42, S-43 S-39, S-40 S-39, S-40 S-39, S-40 D-42 D-42 D-42 T-39

T-39 C-209 B-26, H-23–H-25 H-7 C-208 S-35 S-35 S-35 L-4, L-5 L-4, L-5 D-93 T-52 T-52, U-4 F-41 F-41 H-92 H-92 H-93 H-93 D-55 D-55 T-67 T-67 T-41 T-41 T-41 A-14–A-18 A-14–A-17 A-14–A-17 F-27, F-36–F-40 (continued)

CAT4240—APPENDIX B —2/11/2006—14:23—SRIDHAR—XML MODEL C – pp. 855–890

Appendix B List of Solutes by Molecular Formula

Formula

MW

C13H10N3NaO3

279.23

C13H11BrO5

327.13

C13H11N

181.23

C13H12

168.23

C13H12N2O5S

308.31

C13H12O5

284.23

C13H13N3O4

275.26

C13H15NO4

249.26

C13H17NO4

251.28

C13H20N2O2

236.31

C13H24O4

244.33

C13H28O

200.36

C14H8O2

208.21

C14H8O3 C14H8O4

224.21 240.22

C14H9Cl5

354.49

869

Solutes 2,2 0 -Methylenebiphenyl 5-(4-Aminophenylazo)-2-hydroxybenzoic acid sodium salt C. I. Mordant Yellow 12 Dimethyl 6-bromo-2H-1-benzopyran2,3-dicarboxylate Dimethyl 6-bromo-2H-chromene2,3-dicarboxylate 2-Aminoﬂuorene Fluoren-2-amine Benzyl benzene Diphenylmethane Nimesulide 4-Nitro-2-phenoxymethanesulfonanilide Dimethyl 2H-1-benzopyran2,3-dicarboxylate Dimethyl 2H-chromene2,3-dicarboxylate 2-Methyl-5-nitro-1H-imidazole1-ethanol benzoate Metronidazole benzoate N-Benzyloxycarbonyl-DL-proline N-Carbobenzoxyproline N-Carbobenzoxyvaline N-Benzyloxycarbonyl-DL-valine 2-(Diethylamino)ethyl-4-aminobenzoate Procaine Brassylic acid Tridecanedioic acid 1-Tridecanol Tridecyl alcohol 9,10-Anthracenedione Anthraquinone 9,10-Anthraquinone 1-Hydroxyanthraquinone Alizarin C. I. Mordant Red 11 C. I. Solvent Orange 86 Danthron 1,2-Dihydroxyanthraquinone 1,4-Dihydroxyanthraquinone 1,8-Dihydroxyanthraquinone Quinizarin 1,1-Bis(4-chlorophenyl)-2,2,2trichloroethane DDT 4,4 0 -DDT 4,4 0 -Dichlorodiphenyltrichloroethane

Data Table No. F-27, F-36–F-39 C-157 C-157 D-65 D-65 A-31 A-31 D-89 D-89, N-29 N-73 N-73 D-64 D-64 M-54 M-54 C-25 C-25 C-26 C-26 P-111 P-111 B-66 B-66 T-62 T-62 A-64, A-65 A-64, A-65 A-64, A-65 H-40 C-156 C-156 D-44, D-45 D-46–D-48 C-156 D-44, D-45 D-46–D-48 D-44, D-45 B-56 B-56 B-56 D-1

(continued)

CAT4240—APPENDIX B —2/11/2006—14:23—SRIDHAR—XML MODEL C – pp. 855–890

870

Solubility in Supercritical Carbon Dioxide

Formula

C14H9NO2 C14H10

MW

223.23 178.23

Solutes 1,1,1-Trichloro-2,2bis(4-chlorophenyl)ethane 9-Nitroanthracene Anthracene Phenanthrene

C14H10Cl2NNaO2$4H2O C14H10O2S

242.29

C14H10O3

226.23

C14H10O3S

258.29

C14H11Cl2NO2$Na C14H12O2

318.13 212.24

C14H12O3

228.24

C14H14

182.26

C14H14N2O

226.27

C14H14O3

230.26

390.21

C14H15N3

225.29

C14H20

188.31

C14H22N2O

234.34

C14H27N3O3

285.39

Sodium 2-(2,6-dichloroanilino)phenyl acetate 1-Hydroxy-3-methylthioxanthen-9-one 1-Hydroxy-3-methylthioxanthone 1,8-Dihydroxyanthracen-9(10H)-one 1,8-Dihydroxyanthrone 1,8-Dihydroxy-9-anthrone 1-Hydroxy-3-methyl-9H-xanthen-9-one 1-Hydroxy-3-methylxanthone 1,4-Dihydroxy-3-methyl-9Hthioxanthen-9-one 1,4-Dihydroxy-3-methylthioxanthone Diclofenac sodium Benzoin (G)-2-Hydroxy-1,2-diphenylethanone (G)-2-Hydroxy-2-phenylacetophenone Resveratrol (E)-Resveratrol 3,4 0 ,5-Stilbenetriol 3,4 0 ,5-Trihydroxy-trans-stilbene Bibenzyl 1,2-Diphenylethane N,N-Dimethylindoaniline Phenol Blue (S)-2-(6-Methoxy-2-naphthyl)propionic acid Naproxen (C)-Naproxen (C)-(S)-Naproxen 4-Dimethylaminoazobenzene p-Dimethylaminoazobenzene Decahydro-3,5,1,7-[1,2,3,4]butanetetraylnaphthalene Diadamantane Diamantane 2-(Diethylamino)-2 0 ,6 0 -acetoxylidide 2-(Diethylamino)-N-(2,6-dimethylphenyl)acetamide Lidocaine rac-Boc-Piperazine (S)-Boc-Piperazine (S)-tert-Butyl 3-(tert-butylcarbamoyl)piperazine-1-carboxylate

Data Table No. B-56, D-1 N-77, N-78 A-18, A-27, A-40–A-63, F-40, N-49, P-65, P-66 A-62, A-63, N-31–N-33, N-50, N-51, P-44–P-71 D-36 H-87 H-87 D-49 D-49 D-49 H-88 H-88 D-53 D-53 D-36 B-27 B-27 B-27 R-4 R-4 R-4 R-4 B-34 B-34 P-77, P-78 P-77, P-78 N-55–N-62 N-55–N-62 N-55–N-62 N-55–N-62 D-61, D-62 D-61, D-62 D-12 D-12 D-12 L-9 L-9 L-9 B-65 B-64 B-64

(continued)

CAT4240—APPENDIX B —2/11/2006—14:23—SRIDHAR—XML MODEL C – pp. 855–890

Appendix B List of Solutes by Molecular Formula

Formula C14H28CuN2S4 C14H28HgN2S4 C14H28N2PbS4 C14H28N2PdS4

871

MW

Solutes

416.18 553.22 559.83 559.83 459.07

Copper bis(dipropyldithiocarbamate) Mercury bis(dipropyldithiocarbamate) Bis(diisopropyldithiocarbamato)lead Lead bis(diisopropyldithiocarbamate) Bis(diisopropyldithiocarbamato)palladium Palladium bis(diisopropyldithiocarbamate) Myristic acid Tetradecanoic acid Chromium tris(hexaﬂuoroacetylacetonate) Tris(1,1,1,5,5,5-hexaﬂuoro-2,4pentanedionato)yttrium Yttrium(III) hexaﬂuoroacetylacetonate Yttrium tris(hexaﬂuoroacetylacetonate) Pentadecaﬂuorooctyl 2,5-dichlorobenzoate 2,5-Dichlorobenzoic acid 3,3,4,4,5,5,6,6,7,7,8,8,8tridecaﬂuorooctyl ester Tridecaﬂuorooctyl 2,5-dichlorobenzoate Flavone 2-Phenyl-4-chromone Flavon-3-ol 1-Hydroxy-2-methylanthraquinone 3-Hydroxy-2-phenylchromone 3-Hydroxyﬂavone 7,8-Dihydroxyﬂavone 7,8-Dihydroxy-2-phenyl-4-benzopyrone Emodin 1,3,8-Trihydroxy-6-methylanthraquinone 3,3 0 ,4 0 ,5,7-Pentahydroxyﬂavone Quercetin 1-Amino-2-methylanthraquinone C. I. Disperse Orange 11 C. I. Disperse Red 9 1-(Methylamino)anthraquinone 2-Methylanthracene Arsenic tris[bis(triﬂuoroethyl)dithiocarbamate] 4,4 0 -Isopropylidenebis[2,6-dibromophenol] Tetrabromobisphenol-A 2,2 0 ,6,6 0 -Tetrabromobisphenol A Diclofop 2-[4-(2,4-Dichlorophenoxy)phenoxy]propanoic acid C. I. Modiﬁed Yellow 119

459.07 C14H28O2

228.37

C15H3CrF18O6

N/A

C15H3F18O6Y

746.09

C15H5Cl2F15O2

573.09

C15H7Cl2F13O2

537.10

C15H10O2

222.24

C15H10O3

238.24

C15H10O4

254.24

C15H10O5

270.24

C15H10O7

302.24

C15H11NO2

237.25

C15H12 C15H12AsF18N3S6

192.26 N/A

C15H12Br4O2

543.87

C15H12Cl2O4

327.16

C15H12ClN5O4

361.74

Data Table No. C-189 M-11 L-6 L-6 P-4 M-14, P-4 M-65–M-67 M-65–M-67 M-13 Y-2 Y-2 Y-2 P-33 T-61

T-61 F-30, F-31 F-30, F-31 H-82 H-84 H-82 H-82 D-52 D-52 E-8 E-8 P-39, Q-1 P-39, Q-1 A-32, C-116, C-117 A-32, C-116, C-117 C-126 C-126 M-33, N-78 M-15 T-10 T-10 T-10 P-43 P-43 C-154 (continued)

CAT4240—APPENDIX B —2/11/2006—14:23—SRIDHAR—XML MODEL C – pp. 855–890

872

Solubility in Supercritical Carbon Dioxide

Formula

MW

C15H12CoF18N3S6

N/A

C15H12CrF9O6

511.24

C15H12F18BiN3S6

N/A

C15H12N2O

236.27

C15H12N2O2

252.27

C15H12N2O3

268.27

C15H12O2

224.25

C15H13FO2

244.26

C15H13N3O4S

331.35

C15H13O4N5

327.30

C15H14O6

290.27

Solutes 5-(4-Chloro-2-nitrophenylazo)3-cyano-1-ethyl-6-hydroxy4-methyl-1H-pyridin-2-one Cobalt tris[bis(triﬂuoroethyl)dithiocarbamate] Chromium cis-tris(1,1,1triﬂuoroacetylacetonate) Chromium trans-tris(1,1,1triﬂuoroacetylacetonate) cis-Cr(tfa)3 trans-Cr(tfa)3 cis-Tris(1,1,1-triﬂuoropentane2,4-dionato)chromium trans-Tris(1,1,1-triﬂuoropentane2,4-dionato)chromium Bismuth tris[bis(triﬂuoroethyl)dithiocarbamate] Carbamazepine Carbamazepine Polymorph I Carbamazepine Polymorph III 5H-Dibenz[b,f]azepine-5-carboxamide 5,5-Diphenylhydantoin 5,5-Diphenyl-2,4-imidazolidinedione Phenytoin C. I. Disperse Red 11 1,4-Diamino-2-methoxyanthraquinone 2-Benzoylacetophenone Dibenzoylmethane 1,3-Diphenyl-1,3-propanedione 1-Hydroxy-2-methylanthracen9(10H)-one 1-Hydroxy-2-methylanthrone 2-Fluoro-a-methyl-4-biphenylacetic acid Flurbiprofen 4-Hydroxy-2-methyl-N-2-pyridinyl2H-1,2-benzothiazine-3-carbox amide 1,1-dioxide Piroxicam C. I. Disperse Yellow 119 1-Ethyl-6-hydroxy-4-methyl-5-(2-nitrophenylazo)-2-oxo-1,2-dihydropyridine-3-carbonitrile Catechin (C)-Catechin Epicatechin Epicatechol (C)-(2R,3S)-5,7,3 0 ,4 0 -Tetrahydroxyﬂavan-3-ol (K)-(2R,3R)-5,7,3 0 ,4 0 -Tetrahydroxyﬂavan-3-ol

Data Table No. C-154

M-12, M-13, M-15 C-83 C-84 C-83 C-84 C-83 C-84 M-12, M-13 C-19, C-20 C-21 C-21 C-19–C-21 P-82 P-82 P-82 C-127 C-127 D-19 D-19 D-19 H-85 H-85 F-43 F-43 P-89

P-89 C-153 C-153

C-44 C-44 E-10 E-10 C-44 E-10

(continued)

CAT4240—APPENDIX B —2/11/2006—14:23—SRIDHAR—XML MODEL C – pp. 855–890

Appendix B List of Solutes by Molecular Formula

Formula

873

MW

Solutes

C15H18Br3CrO6

586.01

C15H19N5O4S

365.41

C15H20Cl2O2 C15H21CoO6

303.23 356.26

C15H21CrO6

349.32

C15H21FeO6

353.17

C15H21GaO6

367.05

C15H21InO6

412.15

C15H21MnO6

352.27

C15H21O6Y

386.23

C15H22O5

282.33

C15H26O6

302.36

C15H28O2

240.38

C15H30BiN3S6 C15H30CoN3S6 C15H30N3RhS6 C15H30O4

N/A N/A N/A 274.40

C15H33O C16H8CuF6O4S2

229.42 505.89

Chromium tris(3-bromoacetylacetonate) Cr(acac-Br)3 Tris(3-bromopentane-2,4dionato)chromium C. I. Disperse Blue 102 3-[Ethyl[3-methyl-4-[(5-nitro2-thiazolyl)azo]phenyl]amino]1,2-propanediol Octyl 2,5-dichlorobenzoate Co(acac)3 Cobalt tris(acetylacetonate) Tris(2,4-pentanedionato)cobalt Chromium tris(acetylacetonate) Cr(acac)3 Tris(pentane-2,4-dionato)chromium Fe(acac)3 Iron tris(acetylacetonate) Tris(2,4-pentanedionato)iron Gallium tris(acetylacetonate) Tris(2,4-pentanedionato)gallium Indium tris(acetylacetonate) Tris(2,4-pentanedionato)indium Manganese tris(acetylacetonate) Mn(acac)3 Tris(2,4-pentanedionato)manganese Tris(acetylacetonato)yttrium Tris(2,4-pentanedionato)yttrium Yttrium tris(acetylacetonate) Artemisinin (3R,5aS,6R,8aS,9R,12S,12aR)Octahydro-3,6,9-trimethyl-3,12epoxy-12H-pyrano[4,3-j]-1,2benzodioxepin-10(3H)-one Glycerin tributyrate Glycerol tributanoate Tributanoin Tributyrin Oxacyclohexadecan-2-one Pentadecanolactone 15-Pentadecanolide Bismuth tris(diehtyldithiocarbamate) Cobalt tris(diethyldithiocarbamate) Rhodium tris(diethyldithiocarbamate) Glycerin monolaurate Glycerol monododecanoate Monolaurin 1-Pentadecanol Bis[4,4,4-triﬂuoro-1-(2-thienyl)-1,3butanedionato]copper Copper bis(thenoyltriﬂuoroacetonate)

Data Table No. C-81 C-81 C-81 C-105 C-105

O-18 C-168 C-168 C-168 C-80, M-13 C-80 C-80 I-4, I-5 I-4, I-5 I-4, I-5 G-1 G-1 I-2 I-2 M-3 M-3 M-3 Y-1 Y-1 Y-1 A-69 A-69

T-53, T-54 T-53, T-54 T-53, T-54 T-53, T-54 P-35 P-35 P-35 M-12, M-13 M-12, M-13 M-14 M-62 M-62 M-62 P-34 C-185 C-185 (continued)

CAT4240—APPENDIX B —2/11/2006—14:23—SRIDHAR—XML MODEL C – pp. 855–890

874

Solubility in Supercritical Carbon Dioxide

Formula

MW

Solutes

C16H10

202.25

C16H11N3O3

293.28

C16H12O4

268.26

C16H13ClN2O

284.74

C16H13N3O C16H13NO2

263.30 251.28

C16H14Cl2O4

341.19

C16H14N2O2

266.30

C16H14N4

262.31

C16H14N4O

278.31

C16H14O2

238.28

Benzo[j,k]ﬂuorene Benzo[def]phenanthrene Fluoranthene Pyrene C. I. Pigment Red 1 1-(4-Nitrophenylazo)-2-naphthol Para red 1-Hydroxy-2(methoxymethyl)anthraquinone 7-Chloro-1-methyl-5-phenyl-3H1,4-benzodiazepin-2(1H)-one Diazepam 1-((4-Aminophenyl)azo)-2-naphthol 1-Amino-2,3-dimethylanthraquinone 1-Amino-2,4-dimethylanthraquinone 1-Amino-2-ethylanthraquinone Diclofopmethyl Methyl 2-[4-(2,4dichlorophenoxy)phenoxy]propanoate 1,4-Bis(methylamino)anthraquinone C. I. Disperse Blue 14 C. I. Solvent Brown 1 Fat Brown RR 4-(1-Naphthalenylazo)-1,3-benzenediamine C. I. Disperse Yellow 16 3-Methyl-1-phenyl-4-(phenylazo)pyrazol-5-ol 2-Ethyl-1-hydroxyanthracen-9(10H)-one 4-Hydroxy-1,3-dimethylanthracen10(9H)-one 1-Hydroxy-2,4-dimethylanthrone 1-Hydroxy-2-ethylanthrone m-Benzoylhydratropic acid 2-(3-Benzoylphenyl)propionic acid Ketoprofen DMDT Methoxychlor 1,1,1-Trichloro-2,2-bis(4-methoxyphenyl)ethane N,N 0 -Bis(salicylidene)-1,2-ethanediamine a,a 0 -Ethylenedinitrilodi-o-cresol Salen C. I. Disperse Red 13 4-Nitro-2-chloro-4 0 -[ethyl(2-hydroxyethyl)amino]azobenzene C. I. Disperse Red 30 2,2 0 -[[4-[(2-Chloro-4-nitrophenyl)azo]phenyl]imino]bisethanol

C16H14O3

254.28

C16H15Cl3O2

345.65

C16H16N2O2

268.31

C16H17ClN4O3

348.79

C16H17ClN4O4

364.78

Data Table No. F-33–F-35 P-129–P-137 A-3, F-33–F-35 P-129–P-137 P-18 P-18 P-18 H-44 D-13 D-13 A-33 A-28 A-29 A-30 P-43 P-43 B-46, C-92, C-93 B-46, C-92, C-93 C-162 C-162 C-162 C-108, C-147 C-147 H-81 H-80 H-80 H-81 K-1–K-3 K-1–K-3 K-1–K-3 M-22 M-22, P-43 M-22, P-43 S-1 S-1 S-1 C-128 C-128 C-129 C-129

(continued)

CAT4240—APPENDIX B —2/11/2006—14:24—SRIDHAR—XML MODEL C – pp. 855–890

Appendix B List of Solutes by Molecular Formula

Formula

875

MW

Solutes

C16H18N2O4S

334.39

C16H18N2O5S

350.39

C16H18N4O3

314.35

C16H19N3O5S

365.40

C16H20N4O2

300.36

C16H21NO2

259.35

C16H22ClN3O

307.82

C16H22O11

390.34

C16H23NO6 C16H26Cl2Si2Zr

325.36 434.00

C16H26CuO4

345.93

Benzylpenicillin Penicillin G Penicillin V Phenoxymethylpenicillin C. I. Disperse Red 1 N-Ethyl-N-(2-hydroxyethyl)-4[(p-nitrophenyl)azo]aniline C. I. Disperse Yellow 86 4-(4-Ethoxyanilino)-N,N-dimethyl3-nitrobenzenesulfonamide 4-Amino-4 0 -[bis(2hydroxyethyl)amino]azobenzene C. I. Disperse Black 9 1-(Isopropylamino)-3-(1-naphthyloxy)2-propanol Propranolol 1-(4-Chlorophenyl)-4,4-dimethyl-3(1,2,4-triazol-1-ylmethyl)pentan-3-ol Tebuconazole b-D-Galactopyranose pentaacetate b-D-Galactose pentaacetate D-Glucopyranose pentaacetate D-Glucose pentaacetate 1,2,3,4,6-Pentaacetyl-D-galactose 1,2,3,4,6-Pentaacetyl-D-glucose Monocrotaline Dichlorobis[h5-(trimethylsilyl)cyclopentadienyl]zirconium Bis(5,5-dimethylhexane-2,4-dionato)copper Copper bis(5,5-dimethylhexane2,4-dionate) Cu(dmhd)2 Ethyl myristate Hexadecanoic acid Myristic acid ethyl ester Palmitic acid Tetradecanoic acid ethyl ester Hexadecane Rape seed oil Cetyl alcohol Dicaprylyl ether Dioctyl ether 1-Hexadecanol Octyl ether Palmityl alcohol Bis(2-ethylhexyl) phosphate Di-(2-ethylhexyl)phosphoric acid

C16H32O2

256.42

C16H34

226.44

C16H34O

242.44

C16H35O4P

322.42

Data Table No. P-19 P-19 P-20 P-20 C-123–C-125 C-123–C-125 C-151 C-151 C-89

C-89 P-122 P-112 T-3 T-3 P-21 P-21 P-22 P-22 P-21 P-22 M-60, M-61 C-214 C-179 C-179 C-179 E-21 P-6–P-13 E-21 P-6–P-13 E-21 H-19–H-21 R-1 C-47–C-51 D-83 D-83 C-47–C-51 D-83 C-47–C-51 D-41 D-41 (continued)

CAT4240—APPENDIX B —2/11/2006—14:24—SRIDHAR—XML MODEL C – pp. 855–890

876

Solubility in Supercritical Carbon Dioxide

Formula C17H12O4

MW

Solutes

280.27

1-Hydroxy-4-(prop-2-enyloxy)anthraquinone 1-Hydroxy-8-(prop-2-enyloxy)anthraquinone 1,8-Dihydroxy-2-(prop-2 0 -enyl)anthracen-9-one 1,8-Dihydroxy-2-(prop-2 0 -enyl)anthrone 1-Hydroxy-2-(ethoxymethyl)anthraquinone Dimethyl 3H-benzo[f]chromene-2,3dicarboxylate Dimethyl 3H-naphtho[2,1-b]pyran-2,3dicarboxylate C. I. Disperse Blue 3 1,4-Diaminoanthraquinone, N,N 0 -mixed 2-hydroxyethyl and methyl derivatives 4-Methyl-6-(5-chloro-2-pyridinyl)6,7-dihydro-7-oxo-5H-pyrrolo[3,4-b]pyrazin-5-yl ester 1-Piperazinecarboxylic acid Zopiclone 7-Chloro-2 0 ,4,6-trimethoxy-6 0 methylspiro[benzofuran-2(3H),1 0 -[2] cyclohexene]-3,4 0 -dione Griseofulvin C. I. Disperse Orange 25 4-[N-(2-Cyanoethyl)-N-ethylamino]4 0 -nitroazobenzene 2,8-Dimethyl-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine Troeger’s Base Nifedipine 4-(2-Nitrophenyl)-2,6-dimethyl-3,5dicarbomethoxy-1,4-dihydropyridine N,N 0 -Diethylcarbanilide N,N-Diethyl-N,N 0 -diphenylurea Ethyl centralite Atropine Tropine tropate Decyl 2,5-dichlorobenzoate Heptadecane Tris(pentaﬂuorophenyl)phosphine C. I. Disperse Yellow 54 C. I. Solvent Yellow 114 2-(3-Hydroxy-2-quinolyl)-1,3indanedione 1,2-Benzophenanthrene 9,10-Benzophenanthrene Chrysene 1,2,3,4-Dibenznaphthalene

C17H14O3

266.30

C17H14O4

282.29

C17H14O5

298.29

C17H16N2O3

296.32

C17H17ClN6O3

388.81

C17H17ClO6

352.77

C17H17N5O2

323.35

C17H18N2

250.34

C17H18N2O6

346.33

C17H20N2O

268.35

C17H23NO3

289.37

C17H24Cl2O2 C17H36 C18F15P C18H11NO3

331.28 240.47 532.14 289.28

C18H12

228.29

Data Table No. H-45 H-46 D-54 D-54 H-42 D-76 D-76 C-90, C-91 C-90, C-91 Z-3

Z-3 Z-3 G-10

G-10 C-113, C-119 C-113, C-119 T-104 T-104 N-72 N-72 E-16 E-16 E-16 A-79 A-79 D-10 H-6 T-100 C-149 C-149 C-149 C-85–C-88 T-92, T-93 C-85–C-88 T-92, T-93 (continued)

CAT4240—APPENDIX B —2/11/2006—14:24—SRIDHAR—XML MODEL C – pp. 855–890

Appendix B List of Solutes by Molecular Formula

Formula

MW

C18H12F3P

316.26

C18H14

230.30

C18H14Cl4N2O

416.12

C18H15N

245.32

C18H15N3O4S

369.39

C18H15N5SCl2

404.32

C18H15O4P

326.28

C18H15P

262.29

C18H16O4

293.23

C18H18N2O2

294.35

C18H20N2O6

360.36

C18H21NO3

299.36

C18H24O2

272.38

C18H27NO3

305.41

C18H30CuO4

373.98

C18H32O2

280.45

C18H36CuN2S4

472.28 609.33 N/A N/A

C18H36N2PdS4

C18H36O2

284.48

877

Solutes Triphenylene Tris(4-ﬂuorophenyl)phosphine Tris(p-ﬂuorophenyl)phosphine 1,3-Diphenylbenzene m-Terphenyl 1-[2-(2,4-Dichlorophenyl)-2-[(2,4dichlorophenyl)methoxy]ethyl]1H-imidazole Miconazole N,N-Diphenylbenzenamine Triphenylamine 4-Anilino-3-nitrobenzenesulfonanilide C. I. Disperse Yellow 42 C. I. Disperse Red 153 3-[[4-[[5,6(or 6,7)-Dichloro-2-benzothiazolyl]azo]phenyl]ethylamino] propanenitrile Phosphoric acid triphenyl ester Triphenylphosphate Triphenylphosphine Triphenylphosphorous 1-Hydroxy-2(1-propoxymethyl)anthraquinone 1,4-Bis(ethylamino)anthraquinone C. I. Solvent Blue 105 1,4-Dihydro-2,6-dimethyl-4(3-nitrophenyl)-3,5-pyridinedicarboxylic acid ethyl methyl ester Nitrendipine Codeine Methylmorphine b-Estradiol Estra-1,3,5(10)-triene-3,17-diol Capsaicin (E)-8-Methyl-N-vanillyl-6-nonenamide Bis(2,6-dimethylheptane3,5-dionato)copper Copper bis(2,6-dimethylheptane3,5-dionate) Cu(dibm)2 Linoleic Acid (Z)-9-Octadecenoic acid Oleic acid Copper bis(dibutyldithiocarbamate) Mercury bis(dibutyldithiocarbamate) Palladium bis(dibutydithiocarbamate) Palladium bis(diisobutylldithiocarbamate) Ethyl hexadecanoate Ethyl palmitate

Data Table No. A-3, T-92, T-93 T-99 T-99 T-6 T-6 M-55

M-55 T-91 T-91 C-148 C-148 C-139 C-139

T-96 T-96 T-97, T-98 T-97, T-98 H-47 B-43 B-43 N-75

N-75 C-171 C-171 E-14, E-15 E-14, E-15 C-16–C-18 C-16–C-18 C-178 C-178 C-178 L-24, L-25 O-21–O-26 O-21–O-27 C-189 M-11 M-14 M-14 E-24, E-25 E-24, E-25 (continued)

CAT4240—APPENDIX B —2/11/2006—14:24—SRIDHAR—XML MODEL C – pp. 855–890

878

Solubility in Supercritical Carbon Dioxide

Formula

C18H38 C18H38NO4P

MW

254.49 363.47

C18H38O

270.49

C18H38O6

350.49

C18H38S

268.56

C18H39N

269.51

C19H16

244.33

C19H16N4O

316.36

C19H17Cl2N5O4

450.27

C19H17Cl2N5S

418.34

C19H18O4

310.34

C19H19N7O5

425.40

C19H21BrN6O6

509.31

C19H24N2HCl

316.87

C19H26O7

366.41

Solutes Octadecanoic acid Palmitic acid ethyl ester Stearic acid Octadecane Dihexyl(diethylcarbamoyl)methylphosphonate Dihexyl-(N,N-diethylcarbamoyl)methylphosphonate 1-Octadecanol n-Octadecyl alcohol Stearyl alcohol 1-Stearyl alcohol Octyl pentaethylene glycol ether Octylpentaglycol Pentaethylene glycol n-octyl ether 1-Octadecanethiol Octadecylmercaptan Stearyl mercaptan N,N-Dihexyl-1-hexanamine Trihexylamine 1,1 0 ,1 00 -Methylidynetrisbenzene Triphenylmethane C. I. Disperse Yellow 7 2-Methyl-4-[[4-(phenylazo)phenyl]azo]phenol C. I. Disperse Orange 30 4-[(2,6-Dichloro-4-nitrophenyl)azo]-N(cyanoethyl)-N-(acetoxyethyl) aniline C. I. Disperse Red 152 3-[[4-[[5,6(or 6,7)-Dichloro-2benzothiazolyl]azo]-3-methylphenyl] ethylamino]propanenitrile 1-Hydroxy-2-(1-butoxymethyl)anthraquinone 1-Hydroxy-2-(isobutoxymethyl)anthraquinone C. I. Disperse Blue 165:1 N-[2-[(2-Cyano-4,6-dinitrophenyl)azo]5-(diethylamino)phenyl] acetamide N-[2-[(2-Bromo-4,6-dinitrophenyl)azo]5-(diethylamino)-4-methoxy phenyl]acetamide C. I. Disperse Blue 291 5-[3-(Dimethylamino)propyl]-10,11dihydro-5H-dibenz[b,f]azepine hydrochloride Imipramine hydrochloride Anguidin Diacetoxyscirpenol

Data Table No. S-15–S-29 E-24, E-25 S-16–S-29 O-10, O-11 D-43 D-43 O-12–O-15, S-30–S-32 O-12–O-15, S-30–S-32 S-30–S-32 O-12–O-15 P-36 P-36 P-36 O-16 O-16 O-16 T-66 T-66 T-94, T-95 T-94, T-95 C-145, C-146 C-145, C-146 C-113, C-120, C-121 C-113, C-120, C-121 C-138 C-138

H-41 H-43 C-109 C-109 C-110

C-110 I-1

I-1 D-11 D-11 (continued)

CAT4240—APPENDIX B —2/11/2006—14:24—SRIDHAR—XML MODEL C – pp. 855–890

Appendix B List of Solutes by Molecular Formula

Formula

MW

C19H28O2

288.42

C19H30O5

338.44

C19H37N

279.50

C19H38O

282.50

C19H40 C20H12

268.53 252.31

C20H12CuF6O4

493.85

C20H12N2O6

376.32

C20H13NO4

331.33

C20H14N2O4

346.34

C20H16O4

320.34

C20H17N3O5

379.37

C20H19N3O2

333.38

C20H22N2O2

322.41

C20H28O3

316.43

C20H30O

286.45

879

Solutes 12,13-Epoxytrichothec-9-ene-3a,4b,15triol 4,15-diacetate 17b-Hydroxyandrost-4-en-3-one Testosterone Dodecyl gallate Dodecyl 3,4,5-trihydroxybenzoate Gallic acid dodecyl ester 1-Cyanooctadecane Nonadecanenitrile Octadecyl cyanide Heptadecyl methyl ketone 2-Nonadecanone Nonadecane Dibenz[de,kl]anthracene Perylene a-Perylene Bis(4,4,4-triﬂuoro-1-phenylbutane1,3-dionato)copper Copper bis(1,1,1-triﬂuoro-4-phenylbutane-2,4-dionate) Cu(tfbzm)2 1-Anilino-4,5-dihydroxy-8-nitroanthraquinone C. I. Disperse Blue 77 1-Amino-4-hydroxy-2-phenoxyanthraquinone C. I. Disperse Red 60 1-Amino-4,5-dihydroxy-8(phenylamino)anthraquinone C. I. Disperse Blue 118 1,4-Bis(allyloxy)anthraquinone 1,4-Bis(prop-2 0 -enyloxy)anthraquinone 1,8-Bis(prop-2 0 -enyloxy)anthraquinone 1,8-Dihydroxy-2,7-bis (prop-1 0 -enyl)anthraquinone C. I. Disperse Blue 60 C. I. Disperse Blue 99 1,4-Diamino-N-(3-methoxypropyl)anthraquinone-2,3-dicarboximide 3-(2-Benzimidazolyl)-7-(diethylamino)coumarin C. I. Disperse Yellow 82 1,4-Bis(isopropylamino)anthraquinone 1,4-Bis(propylamino)anthraquinone C. I. Disperse Blue 134 Cafesterol Cafestol (all-E)-3,7-Dimethyl-9-(2,6,6-trimethyl1-cyclohexen-1-yl)-2,4,6,8nonatetraen-1-ol

Data Table No. D-11 T-7, T-8 C-79, P-114, T-7, T-8 D-94 D-94 D-94 N-87 N-87 N-87 N-88 N-88 N-85, N-86 P-40–P-42 P-40–P-42 P-40–P-42 C-187 C-187 C-187 C-99 C-99 C-113, C-130–C-135 C-113, C-130–C-135 C-106 C-106 B-53, B-54 B-53 B-54 D-51 C-95–C-97 C-95–C-97 C-95–C-97 C-150 C-150 B-45, C-107 B-55 B-45, C-107, C-108 C-1 C-1 R-5

(continued)

CAT4240—APPENDIX B —2/11/2006—14:24—SRIDHAR—XML MODEL C – pp. 855–890

880

Solubility in Supercritical Carbon Dioxide

Formula

MW

C20H38O2

310.51

C20H40O2

312.53

C20H42 C20H42O

282.55 298.55

C20H42O5

362.54

C20H43O4P

378.53

C21H12F9P C21H20O9

466.29 416.38

C21H21N5O6

439.43

C21H22F2O8

440.40

C21H24O8

404.42

C21H26N2O7

418.44

C21H26O5

358.43

C21H28O5

360.44

C21H30O2

314.46

C21H30O5

362.46

Solutes Retinol all-trans-Retinol Vitamin A Ethyl oleate (Z)-9-Octadecenoic acid ethyl ester Oleic acid ethyl ester Arachidic acid Eicosanoic acid Ethyl octadecanoate Ethyl stearate Stearic acid ethyl ester Eicosane Arachidyl alcohol 1-Eicosanol Tetraethylene glycol lauryl ether Tetraethylene glycol monododecyl ether Bis(8-methylnonyl) hydrogen phosphate Diisodecyl phosphoric acid Tris(p-triﬂuoromethylphenyl)phosphine 3-[(6-Deoxy-a-L-mannopyranosyl)oxy]1,8-dihydroxy-6-methyl anthaquinone Frangulin A C. I. Disperse Red 82 3-Nitro-6-[4-[N,N-di(acetoxyethyl)amino]phenyl]azobenzonitrile 3(6),3 0 (6 0 )-Diﬂuorodibenzo-16-crown -5-oxyacetic acid Lariat ether carboxylic acid, ringﬂuorinated Dibenzo-16-crown-5-oxyacetic acid Lariat ether carboxylic acid, non-ﬂuorinated 1,4-Dihydro-2,6-dimethyl-4(3-nitrophenyl)-3,5-pyridinedicarboxylic acid 2-methoxyethyl 1-methylethyl ester Nimodipine 1,2-Dehydrocortisone 17,21-Dihydroxy-1,4-pregnadiene3,11,20-trione Prednisone 1,2-Dehydrohydrocortisone Prednisolone 11b,17,21-Trihydroxy-1,4-pregnadiene3,20-dione Pregn-4-ene-3,20-dione Progesterone Cortisol Hydrocortisone

Data Table No. R-5 R-5 R-5 E-22, E-23 E-22, E-23 E-22, E-23 E-4 E-4 E-26 E-26 E-26 E-2, E-3 A-67, E-5 A-67, E-5 T-29 T-29 D-57 D-57 T-101 F-44 F-44 C-136 C-136 L-2 L-2 L-2 L-2 N-74

N-74 P-110 P-110 P-110 P-109 P-109 P-109 P-112 P-112–P-114 H-33 H-33 (continued)

CAT4240—APPENDIX B —2/11/2006—14:24—SRIDHAR—XML MODEL C – pp. 855–890

Appendix B List of Solutes by Molecular Formula

Formula

MW

C21H36O2

296.49

C21H38O6

386.52

C21H40O4

356.55

C21H42N3RhS6

631.87

C21H44 C22H12

296.58 276.33

C22H16N2O7

420.37

C22H16N4O

352.39

C22H19NO4

361.39

C22H22N4Ni

401.15

C22H24N6O9

516.46

C22H26N2O2

350.46

C22H29FO5

392.46

C22H32O3

344.49

C22H34O2

330.50

C22H36N4O3

404.55

881

Solutes 11b,17a,21-Trihydroxypregn-4-ene3,20-dione Methyl oleate (Z)-9-Octadecenoic acid methyl ester Oleic acid methyl ester Glycerin trihexanoate Glycerol tricaproate Tricaproin Trihexanoin Glycerin monooleate Glycerol monooleate Monoolein Rhodium tris(diisopropyldithiocarbamate) Tris(diisopropyldithiocarbamato)rhodium Heneicosane Benzo[ghi]perylene 1,12-Benzoperylene C. I. Disperse Blue 27 1,8-Dihydroxy-4-(p-2-hydroxyethylanilino)-5-nitroanthraquinone C. I. Disperse Orange 13 4-[4-(Phenylazo)-1-naphthylazo]phenol Bisacodyl 4,4 0 -(2-Pyridylmethylene)bisphenol diacetate Nickel complex (5,7,12,14-Tetramethyl-2,3:9,10dibenzo-[b,i][1,4,8,11]tetraaza cyclotetradecine)nickel (II). N-[5-[Bis[2-(acetyloxy)ethyl] amino]-2[(2,4-dinitrophenyl)azo] phenyl]acetamide C. I. Disperse Violet 91 1,4-Bis(butylamino)anthraquinone C. I. Solvent Blue 35 Sudan Blue II Betamethasone 9a-Fluoro-16b-methylprednisolone 17b-(1-Oxopropoxy)-androst-4-en-3-one Testosterone-17-propionate Eicosapentaenoic acid ethyl ester (all Z)-5,8,11,14,17-Eicosapentaenoic acid ethyl ester Ethyl eicosapentaenoate 4-(Hexadecylamino)-7-nitrobenz-2-oxa1,3-diazole

Data Table No. H-33 M-48–M-50 M-48–M-50 M-48–M-50 T-56 T-56 T-56 T-56 M-63, M-64 M-63, M-64 M-63, M-64 M-14, R-6 R-6 H-1 B-29 B-29 C-94 C-94

C-118 C-118 B-39 B-39 N-64–N-66 N-64–N-66

C-144

C-144 B-40, B-41, C-161 B-40, B-41, C-161 C-161 B-32 B-32 T-9 T-9 E-6 E-6 E-6 H-22

(continued)

CAT4240—APPENDIX B —2/11/2006—14:24—SRIDHAR—XML MODEL C – pp. 855–890

882

Solubility in Supercritical Carbon Dioxide

Formula

MW

C22H36O2

332.52

C22H38CuO4

430.09

C22H38O2 C22H38O4Pd

334.54 472.94

C22H38O7

414.53

C22H44CuN2S4 C22H44HgN2S4 C22H44N2PdS4 C22H44O2

528.39 665.43 N/A 340.58

C22H46 C23H25BrN6O10

310.60 625.38

C23H26ClN5O7

519.93

C23H26O5

382.46

C23H30O6

402.48

Solutes N-Hexadecyl-7-nitro-4benzofurazanamine NBD Arachidonic acid ethyl ester (all Z)-5,8,11,14-Eicosatetraenoic acid ethyl ester Ethyl arachidonate Bis(2,2,6,6-tetramethylheptane-3,5dionato)copper Bis(2,2,7-trimethyloctane-3,5dionato)copper Copper bis(2,2,6,6-tetramethylheptane3,5-dionate) Copper bis(2,2,7-trimethyloctane-3,5dionate) Cu(thd)2 Cu(tod)2 Eicosatrienoic acid ethyl ester Bis(2,2,6,6-tetramethyl-3,5heptanedionato)palladium Palladium bis(2,2,6,6-tetramethyl-3,5heptanedionate) Pd(thd)2 L-Ascorbic acid 6-hexadecanoate Ascorbyl palmitate Ascorbic acid 6-palmitate Copper bis(dipentyldithiocarbamate) Mercury bis(dipentyldithiocarbamate) Palladium bis(dipentyldithiocarbamate) Behenic acid Docosanoic acid Docosane N-[5-[Bis[2-(acetyloxy)ethyl]amino]2-[(2-bromo-4,6-dinitrophenyl) azo]4-methoxyphenyl]acetamide 4-(6-Bromo-2,4-dinitrophenylazo)3-acetylamino-6-methoxy-N-bis (acetoxyethyl)aniline C. I. Disperse Blue 79:1 N-[5-[Bis[2-(acetyloxy)ethyl] amino]2-[(2-chloro-4-nitrophenyl)azo] phenyl]propanamide C. I. Disperse Red 167 Di-tert-butyl 3H-benzo[f]chromene2,3-dicarboxylate Di-tert-butyl 3H-naphtho[2,1-b]pyran2,3-dicarboxylate 21-Acetoxy-17a-hydroxypregn-4-ene3,11,20-trione Cortisone acetate

Data Table No. H-22 H-22 A-66 A-66 A-66 C-183, C-184 C-188 C-183, C-184 C-188 C-183, C-184 C-188 E-7 P-3 P-3 P-3 A-71 A-71 A-71 C-189 M-11 M-14 B-4–B-7 B-4–B-7 D-92 C-103, C-104

C-103, C-104

C-103, C-104 C-140

C-140 D-20 D-20 C-191 C-191 (continued)

CAT4240—APPENDIX B —2/11/2006—14:25—SRIDHAR—XML MODEL C – pp. 855–890

Appendix B List of Solutes by Molecular Formula

Formula

C24H20CoOP

MW

413.31

C24H27BrN6O10

639.42

C24H29ClO4

416.94

C24H30N2O2

378.51

C24H32O4

384.51

C24H32O8

448.51

C24H34O4

386.52

C24H36O2

356.54

C24H38O4

390.56

C24H42NO2P

407.57

C24H50 C24H50S

338.65 370.72

C24H51N

353.67

C24H51OP

386.63

C24H51P

370.64

C25H32O2 C25H52 C26H36O9

280.45 352.68 492.56

883

Solutes Cortisone 21-acetate Carbonyl-p-cyclopentadienyl(triphenylphosphine)cobalt Carbonyl(h5-cyclopentadienyl)(triphenylphosphine)cobalt N-[5-[Bis[2-(acetyloxy)ethyl]amino]2-[(2-bromo-4,6-dinitrophenyl) azo]4-ethoxyphenyl]acetamide C. I. Disperse Blue 79 6-Chloro-1,2a-methylene-6-dehydro17a-hydroxyprogesterone acetate Cyproterone acetate 1,4-Bis(pentylamino)anthraquinone C. I. Solvent Blue 14 17a-Acetoxy-6-dehydro-6-methylprogesterone Megestrol acetate Dibenzo-24-Crown-8 6,7,9,10,12,13,20,21,23,24,26,27Dodecahydrodibenz[b,n] [1,4,7,10,13,16,19,22]octaoxacyclotetracosin 17a-Acetoxy-6a-methylprogesterone Medroxyprogesterone acetate Docosahexaenoic acid ethyl ester (all-Z)-4,7,10,13,16,19Docosahexaenoic acid ethyl ester Ethyl docosahexaenoate Bis(2-ethylhexyl) phthalate Dioctyl phthalate Octyl(phenyl)(N,N-diisobutylcarbamoyl)methylphosphine oxide Tetracosane Didodecylsulfane Didodecylthioether Didodecylamine Di-n-dodecylamine Dilaurylamine Tricaprylylamine Trioctylamine Tri-n-octylamine Trioctylphosphine oxide Tri-n-octylphosphine oxide Didodecylphosphine Dilaurylphosphine Trioctylphosphine Tri-n-octylphosphine (Z,Z)-9,12-Octadecadienoic acid Pentacosane Dibenzo-27-Crown-9

Data Table No. C-191 C-27 C-27 C-100–C-102

C-100–C-102 C-216 C-216, M-5 B-52 B-52 M-6 M-6 D-14 D-14

M-4 M-4, M-5 D-90, D-91 D-90, D-91 D-90, D-91 D-84 D-84 O-19 T-17–T-22 D-39 D-39 D-37 D-37 D-37 T-79 T-79 T-79 T-81, U-4 T-81 D-38 D-38 T-80 T-80 L-24, L-25 P-31, P-32 D-15 (continued)

CAT4240—APPENDIX B —2/11/2006—14:25—SRIDHAR—XML MODEL C – pp. 855–890

884

Solubility in Supercritical Carbon Dioxide

Formula

MW

C26H42O4

418.61

C26H52CuN2S4 C26H52HgN2S4 C26H54 C27H44O

584.50 721.54 366.71 384.64

C27H46O

386.65

C27H46O2

402.65

C27H50O6

470.68

C27H52O5

456.70

C27H54N3RhS6 C27H56 C28H24O4

N/A N/A 380.73 424.49

C28H37ClO7

521.04

C28H37FO7 C28H40O10

504.59 536.61

C28H44O

396.65

C28H58 C29H26F6O8

394.76 616.51

Solutes 6,7,9,10,12,13,15,16,23,24,26,27,29, 30-Tetradecahydrodibenzo [b,n] [1,4,7,10,13,16,19,22,25]nonaoxacycloheptacosin Dinonyl 1,2-benzenedicarboxylate Dinonyl phthalate Copper bis(dihexyldithiocarbamate) Mercury bis(dihexyldithiocarbamate) Hexacosane Cholecalciferol Vitamin D3 Cholest-5-en-3b-ol Cholesterol [2R[2R*(4R*,8R*)]]-3,4-Dihydro-2,8dimethyl-2-(4,8,12-trimethyl tridecyl)-2H-benzopyran-6-ol d-Tocopherol Dd-Tocopherol Glycerin trioctanoate Glycerol tricaprylate Tricaprylin Trioctanoin Didodecanoyl glycerol Dilaurin Glycerol dilaurate Rhodium tris(dibutyldithiocarbamate) Rhodium tris(diisobutyldithiocarbamate) Heptacosane Calix[4]arene Calix[4]arene-25,26,27,28-tetrol Beclomethasone-17,21-dipropionate 9a-Chloro-16b-methylprednisolone 17,21-dipropionate Betamethasone-17,21-dipropionate Dibenzo-30-Crown-10 6,7,9,10,12,13,15,16,23,24,26,27,29, 30,32,33-Hexadecahydro dibenzo[b,q][1,4,7,10,13,16,19,22,25,28]decaoxacyclotriacontin Calciferol Ergocalciferol (3b,22E)-Ergosta-5,7,22-trien-3-ol Ergosterol 24-Methylcholesta-5,7,22-trien-3b-ol Vitamin D2 Octacosane [3,5-Di(triﬂuoromethyl)phenyl]dibenzo16-crown-5-oxyacetic acid Lariat ether carboxylic acid, ﬂuorinecontaining

Data Table No. D-15

D-79–D-82 D-79–D-82 C-189 M-11 H-17, H-18 V-9, V-10 V-9, V-10 C-64–C-74 C-64–C-74, C-79, P-113 T-49, T-50

T-49, T-50 T-49, T-50 T-57 T-57 T-57 T-57 D-58 D-58 D-58 M-14 M-14 H-5 C-12 C-12 B-2 B-2 B-33 D-16 D-16

V-7, V-8 V-7, V-8 E-11, E-12 E-11, E-12, S-34 E-11, E-12 V-7, V-8 O-1–O-9 L-2 L-2

(continued)

CAT4240—APPENDIX B —2/11/2006—14:25—SRIDHAR—XML MODEL C – pp. 855–890

Appendix B List of Solutes by Molecular Formula

Formula

885

MW

Solutes

C29H43NO2S

469.72

C29H48O

412.69

C29H48O2

428.69

C29H50O2

430.71

(S)-2-(Dodecylthio)-N-(4-hydroxy-2,3,5trimethylphenyl)-2-phenyl acetamide Eﬂucimibe (3b,22E)-Stigmasta-5,22-dien-3-ol Stigmasterol Cholesterol acetate Cholesteryl acetate (2R)-3,4-Dihydro-2,5,7,8-tetramethyl2-[(4R,8R)-4,8,12-trimethyl tridecyl]2H-1-benzopyran-6-ol a-Tocopherol DL-a-Tocopherol Vitamin E Nonacosane 1,4-Bis(octylamino)anthraquinone (all E)-2,6,10,15,19,23-Hexamethyl2,6,10,14,18,22-tetracosahexaene Squalene 2,6,10,15,19,23-Hexamethyltetracosane Squalane Triacontane C. I. Disperse Blue 354 [2-[[4-(Dihexylamino)-2-methylphenyl] methylene]-1,1-dioxidobenzo [b]thien-3(2H)-ylidene] propanedinitrile Phylloquinone Phytomenadione Vitamin K1 Cholesterol butanoate Cholesterol butyrate Cholesteryl butyrate N,N 0 -Bis(4,6-di-tert-butylsalicylidene)ethylenediamine tert-Butyl-salen Dotriacontane 18b-Hydroxy-11,17a-dimethoxy3b,20a-yohimban-16b-carboxylic acid methyl ester 3,4,5-trimethoxybenzoate Reserpine Carbonyl-p-cyclopentadienyl(tris(4-trimethylsilylphenyl)phosphine) cobalt Carbonyl(h5-cyclopentadienyl) [tris(4-trimethylsilylphenyl)phosphine] cobalt Chromium tris(2,2,6,6tetramethylheptane-3,5-dionate) Cr(thd)3

C29H60 C30H42N2O2 C30H50

408.79 462.67 410.72

C30H62

422.81

C31H37N3O2S

515.71

C31H46O2

450.70

C31H52O2

456.74

C32H48N2O2

492.74

C32H66 C33H40N2O9

450.87 608.68

C33H45CoOPSi3

630.87

C33H57CrO6

601.81

Data Table No. E-1 E-1 S-33, S-34 S-33, S-34 C-75 C-75 T-44–T-48

T-44–T-48 T-44–T-48 T-44–T-48 N-83, N-84 B-48–B-51 S-13, S-14 S-13, S-14 S-7–S-12 S-7–S-12 T-51 C-111 C-111

V-11 V-11 V-11 C-78 C-78 C-78 B-81 B-81 D-95–D-98 R-2

R-2 C-28

C-28

C-82 C-82 (continued)

CAT4240—APPENDIX B —2/11/2006—14:25—SRIDHAR—XML MODEL C – pp. 855–890

886

Solubility in Supercritical Carbon Dioxide

Formula

C33H57FeO6

C33H57O6Rh

C33H57O6Tb

MW

605.65

652.72

708.74

C33H62O6

554.84

C33H68 C34H50O2

464.90 490.76

C34H53NaO8 C34H68N2PdS4 C34H74O10 C35H72O10 C36H30Cl2NiP2

612.78 N/A 638.92 652.95 654.20

C36H60O2

524.87

C36H61NaO11 C36H74 C36H74O10 C37H67NO13 C38H58N2O2 C38H76O2

692.86 506.97 666.98 733.93 574.88 565.01

Solutes Tris(2,2,6,6-tetramethylheptane-3,5dionato)chromium Fe(thd)3 Fe(tod)3 Iron tris(2,2,6,6-tetramethyl-3,5heptanedionate) Iron tris(2,2,7-trimethyl-3,5octanedionate) Tris(2,2,6,6-tetramethyl-3,5heptanedionato)iron Tris(2,2,7-trimethyl-3,5octanedionato)iron Rhodium tris(2,2,6,6-tetramethyl-3,5heptanedionate) Tris(2,2,6,6-tetramethyl-3,5heptanedionato)rhodium Tb(thd)3 Tb(tod)3 Terbium tris(2,2,6,6-tetramethyl-3,5heptanedionate) Terbium tris(2,2,7-trimethyl-3,5octanedionate) Tris(2,2,6,6-tetramethyl-3,5heptanedionato)terbium Tris(2,2,7-trimethyl-3,5octanedionato)terbium Glycerin tridecanoate Glycerol tricaprate Tricaprin Tridecanoin Tritriacontane Cholesterol benzoate Cholesteryl benzoate Lasalocid sodium salt Palladium bis(dioctyldithiocarbamate) Surfactant Ls-54 Surfactant Ls-45 Dichlorobis(triphenylphosphine)nickel(II) Retinol hexadecanoate all-trans-Retinol palmitate Vitamin A Palmitate Monensin sodium salt Hexatriacontane Surfactant Ls-36 Erythromycin 1,4-Bis(dodecylamino)anthraquinone Cetyl behenate Hexadecyl docosanoate Palmityl behenate

Data Table No. C-82 I-6 I-7 I-6 I-7 I-6 I-7 R-8 R-8 T-4 T-5 T-4 T-5 T-4 T-5 T-55 T-55 T-55 T-55 T-103 C-76, C-77 C-76, C-77 L-3 M-14 S-38 S-37 D-29 V-6 V-6 V-6 M-59 H-30–H-32 S-36 E-13 B-42 P-14 P-14 P-14 (continued)

CAT4240—APPENDIX B —2/11/2006—14:25—SRIDHAR—XML MODEL C – pp. 855–890

Appendix B List of Solutes by Molecular Formula

Formula

MW

C39H72O5

620.99

C39H74O6

639.00

C39H78N3RhS6 C40H56

N/A 536.87

C42H69NaO11 C43H71NaO11

772.99 787.02

C44H10F20N4

974.55

C44H56O4 C44H68O13

648.94 805.00

C44H76CeO8

873.20

C44H88O2

649.17

C45H86O6

723.16

C46H74N2O2 C47H51NO14

687.09 853.91

C50H82N2O2 C51H98O6

743.21 807.32

C51H102N3RhS6 C52H22F24N4

N/A 1158.73

C57H98O6

879.38

C57H104O6

885.43

887

Solutes Diolein Glycerol dioeate Glycerin tridodexanoate Glycerol trilaurate Tridodecanoin Trilaurin Rhodium tris(dihexyldithiocarbamate) b-Carotene b,b-Carotene C. I. Food Orange 5 Salinomycin sodium salt (4S)-4-Methylsalinomycin sadium salt Narasin sodium salt 5,10,15,20-Tetrakis(pentaﬂuorophenyl)porphine 5,10,15,20-Tetrakis(pentaﬂuorophenyl)porphyrin p-tert-Butylcalix[4]arene 9,10-Deepithio-9,10-didehydroacanthifolicin Okadaic acid Ce(thd)4 Ce(tod)4 Cerium tetrakis(2,2,6,6-tetramethyl3,5-heptanedionate) Cerium tetrakis(2,2,7-trimethyl-3,5octanedionate) Tetrakis(2,2,6,6-tetramethyl-3,5heptanedionato)cerium Tetrakis(2,2,7-trimethyl-3,5octanedionato)cerium Behenyl behenate Docosyl docosanoate Glycerin trimyristate Glycerol tritetradecanoate Trimyristin 1,4-Bis(hexadecylamino)anthraquinone Paclitaxel Taxol 1,4-Bis(octadecylamino)anthraquinone Glycerin tripalmitate Glycerol trihexadecanoate Tripalmitin Rhodium tris(dioctyldithiocarbamate) 5,10,15,20-Tetrakis(3,5-bis(triﬂuoromethyl)phenyl)porphyrin Glycerin trilinoleate Glycerol trilinoleate Trilinolein Glycerin trioleate

Data Table No. D-85 D-85 T-69, T-70 T-69, T-70 T-69, T-70 T-69–T-73 M-14 C-29–C-40 C-29–C-40 C-29–C-40 S-2 N-63 N-63 T-24 T-24 B-73 O-20 O-20 C-45 C-46 C-45 C-46 C-45 C-46 B-8 B-8 T-75 T-75 T-71, T-72, T-75, T-76 B-44 T-1, T-2 T-1, T-2 B-47 T-87–T-90 T-87–T-90 T-72, T-73, T-76, T-87–T-90 M-14 T-23 T-74 T-74 T-74 T-82–T-86 (continued)

CAT4240—APPENDIX B —2/11/2006—14:25—SRIDHAR—XML MODEL C – pp. 855–890

888

Solubility in Supercritical Carbon Dioxide

Formula

MW

C57H110O6

891.48

C59H90O4

863.34

C66H84O6 C72H96O48

973.40 1729.50

C84H112O56

2017.75

C88H112O8 C96H128O64

1297.87 2306.03

H2O UO2(C5H4F3O2)2$ C5H5N UO2(C8H4F3O2S)2$ X UO2$(C10H6 F3O3S)2$ 2(C12H27O4P) UO2(NO3)2$ 2(C12H27O4P) N/A

18.02 655.29 736.40 1329.09

926.67 N/A N/A 326.50 N/A N/A N/A 201.00 304.00 572.00 N/A N/A N/A N/A N/A 379.00 399.00 N/A N/A 430.00 426.00

Solutes

Data Table No.

Glycerol trioleate Triolein Glycerin tristearate Glycerol trioctadecanoate Tristearin Coenzyme Q10 (all-E)-2-(3,7,11,15,19,23, 27,31,35, 39-Decamethyl-2,6,10,14,18, 22,26,30,34,38-tetracontadecaenyl)5,6-dimethoxy-3-methyl-pbenzoquinone Ubiquinone Q10 p-tert-Butylcalix[6]arene a-Cyclodextrin octadecaacetate 2,3,6-Triacetyl-a-cyclodextrin b-Cyclodextrin heneicosaacetate 2,3,6-Triacetyl-b-cyclodextrin p-tert-Butylcalix[8]arene g-Cyclodextrin tetracosaacetate 2,3,6-Triacetyl-g-cyclodextrin Water Uranyl bis(triﬂuoroacetylacetonate) pyridine complex Uranyl bis(thenoyltriﬂuoroacetonate) phosphate complexes Uranyl thenoyltriﬂuoroacetylacetonate tributyl phosphate complex

T-82–T-86 T-82–T-86 T-102 T-102 T-102 C-172 C-172

Uranyl dinitrate tributyl phosphate complex Albumin Aniseed Essential Oil Aroclor 1254 Beef shank fat Bisphenol A-type epoxy resin Bitumen Bitumen Cut 1 Bitumen Cut 2 Bitumen Cut 3 Black pepper essential oil Blackcurrant seed oil Canola oil Castor oil Chlorophyllian pigments C. I. Disperse Blue 60S C. I. Disperse Brown 22 C. I. Disperse Orange 1 C. I. Disperse Orange 33 C. I. Disperse Red 137 C. I. Disperse Red 324

U-6, U-7

C-172 B-74 C-205 C-205 C-206 C-206 B-75 C-207 C-207 W-1–W-4 U-5 U-4 U-8

A-22 A-36 A-68 B-3 P-102 B-57, B-58 B-59 B-60 B-61 B-63 B-62 C-14 C-43 C-62 C-98 C-112 C-113 C-122 C-137 C-141, C-142 (continued)

CAT4240—APPENDIX B —2/11/2006—14:26—SRIDHAR—XML MODEL C – pp. 855–890

Appendix B List of Solutes by Molecular Formula

Formula

889

MW

Solutes

469.00 429.00 N/A N/A N/A N/A N/A N/A N/A N/A N/A N/A N/A N/A N/A N/A N/A N/A N/A N/A N/A N/A N/A N/A N/A N/A N/A

C. I. Disperse Red W-4BS C. I. Disperse Yellow 108 Clove buds extract Cocoa butter Cupuacu seed fat Eucalyptus leaves extract Ewe’s milk fat Fish liver oil (cod) Fish liver oil (deep sea shark) Fish liver oil (orange roughy ﬁsh) Fish liver oil (spiny dogﬁsh) Fish oil (sand eel) Fish oil ethyl esters (EE-1) Fish oil ethyl esters (EE-2) Fish oil ethyl esters (EE-3) Fish oil ethyl esters (EE-4) Fish oil ethyl esters (EE-5) Fish oil ethyl esters (EE-6) Fish oil ethyl esters (EE-7) Fish oil ethyl esters (EE-8) Fish oil ethyl esters (EE-9) Fish oil ethyl esters (EE-10) Fish oil ethyl esters (EE-11) Fish oil ethyl esters (EE-12) Fish oil ethyl esters (EE-13) Fish oil fatty acid ethyl ester Fish oil fatty acid ethyl ester, Omega 3 concentrate Fish oil fatty acid ethyl ester, original FAEE Fish oil fatty acid ethyl ester, urea fractionated Fungal oil Ginger rhizomes extract Grape seed oil Jojoba bean oil Jojoba wax Krytox dithiol Krytox picolyl amine Lecithin S20 Lipids Milk fat triglyceride Milk thistle seed oil 4-(N-Phenylamino)-4 0 -nitroazobenzene Olive oil Orange peel oil Palladium diimine BArF complex Palm kernel oil Palm oil PCB 1254

N/A N/A N/A N/A N/A N/A N/A N/A N/A N/A N/A N/A N/A N/A N/A N/A N/A N/A N/A 326.50

Data Table No. C-143 C-152 C-165 C-169, C-170 C-203 E-27 E-30 F-9, F-10 F-13 F-11 F-12, F-13 F-14 F-15 F-16 F-17 F-18 F-19 F-20 F-21 F-22 F-23 F-24 F-25 F-26 F-27 F-28 F-28 F-28 F-28, F-29 F-46 G-3 G-9 J-1 J-1 K-4 K-5 L-7 L-26 M-56 M-57 C-113 O-27 O-28 P-5 P-15, P-16 P-17 A-68 (continued)

CAT4240—APPENDIX B —2/11/2006—14:26—SRIDHAR—XML MODEL C – pp. 855–890

890

Solubility in Supercritical Carbon Dioxide

Formula

MW

Solutes

N/A N/A 90,000–1,20,000 1!106 1,000–7,500 N/A

PEG Pesticides PMMA Poly(1,1-dihydroperﬂuorooctyl acrylate) Polyethylene glycol Poly(ethylene glycol-block-propylene glycol) Poly(ethylene glycol) dimethylether Poly(ethylene glycol) diol Poly(ethylene glycol) monomethylether Poly(ethylene glycol-ran-propylene glycol) Poly(ethyl vinyl ether) Poly(FOEMA-co-PPGMA) Poly(b-hydroxybutyrate) Poly(methyl methacrylate) Poly(oxyalkylene) alkylphenyl ether Poly(propylene glycol) diol Poly(propylene glycol) monobutylether Poly(propylene glycol) monomethylether Poly(styrene) Poly(tetraﬂuoroethylene-co-vinyl acetate) Poly(vinyl butyral) PS-b-(PMMA-co-PGMA) Rosemary oil Shale oil Soybean oil Triglycerides Turmeric oil Vegetable oil from Buriti fruit Wax Wool wax Zinc bis(triﬂuoroethyl)dithiocarbamate Zinc dibutyldithiocarbamate Zinc diethyldithiocarbamate Zinc dihexyldithiocarbamate Zinc dipentyldithiocarbamate Zinc dipropyldithiocarbamate Zinc dithiocarbamate complexes Zinc pyrrolidinedithiocarbamate

500 200–600 350–1,000 970–1,700 1,500 N/A 8,00,000 5,40,000 N/A 400–2,000 1,000 1,000, 1,200 N/A 1,40,000–1,66,000 N/A N/A N/A N/A N/A N/A N/A N/A N/A N/A N/A N/A N/A N/A N/A N/A N/A N/A

CAT4240—APPENDIX B —2/11/2006—14:26—SRIDHAR—XML MODEL C – pp. 855–890

Data Table No. P-102 P-43 P-102 P-91 P-92, P-93 P-94 P-95 P-96 P-97 P-98 P-99 P-100 P-101 P-103 P-102 P-104 P-105 P-106 P-102 P-107 P-108 P-102 R-9 S-3 S-6 T-65 T-106 V-4 W-5 W-6 Z-2 Z-2 Z-2 Z-2 Z-2 Z-2 Z-2 Z-2

Index A Acenaphthene, 19–21 ﬂuoranthene (2)C triphenylene (3), 21 1,2-dihydrocacenaphthylene, 19–20 4-Acetamidophenyl acetate, p-Acetoxyacetanilide, 25–26 Acetaminophen, 4 0 hydroxyacetanilide, 22–23 N-(4-hydroxyphenyl)acetamide, 22–23 Acetic acid, 23 Acetone, 24 21-Acetoxy-17a-hydroxypregn-4-ene-3,11,20trione, 258 4 0 -Acetoxyacetanilide, p-Acetoxyacetanilide, 25–26 2-Acetoxybenzoic acid, aspirin, 68–69 Acetronitrile, methyl cyanide, 25 Acetylsalicylic acid, 2-acetoxybenzoic acid, 26 aspirin, 68–69 2-Acetylsalicylic acid, aspirin, 26 Acridine, 26–29 2,3-benzoquinoline, 26–29 9-azaanthracene, 26–29 anthracene(2) mixture, 29 Adamantane, 29–31 tricyclo[3.3.1.13,7]decane, 31 Aesculetin 6-7-dihydroxycourmarin, 31 esculetin, 31 Albumin, 32 All-trans-Retinol, 703 palmitate, 819 4-Allyl-2-methoxyphenol, 349 Ametryne, 32–33 2-ethylamino-4-isopropylamino-6-methylthio1,3,5-triazine, 33 4-Aminobenzoic acid ethyl ester, benzocaine, 82–84 2-Aminoacetic acid, 384 2-Aminobenzoic acid, 35 2-carboxyaniline, 34 anthralilic acid, 34 2-Aminoﬂuorene, Fluoren-2-amine, 38 2-Aminopyrazine, pyrazinamine, 40 Analytical method, 5 17b-(1-oxopropoxy)-androst-4-en-3-one, 741–742 Aniseed essential oil, 41

Anisole, 42–43 (1) 1-methylnaphthalene (2) mixture, 43 methoxybenzene, 42–43 9,10-Anthracenedione, 9,10-Anthraquinone, 64–65 Anthracene, 43–64 phenanthrene, 632 C carbazole mixture, 63, 64 Anthralilic acid, 2-Aminobenzoic acid, 34 Anthraquinone 1,4-bis(prop-2 0 -enyloxy)anthraquinone, 130–132 1,4-bis(propylamino)anthraquinone, 132–134 1,4-bix(allyloxy)anthraquinone, 1,4-Bis(prop-2 0 enyloxy)anthraquinone, 131–132 1,8-dihydroxy-2,7-bis(prop-1 0 -enyl) anthraquinone, 305 1,8-dihydroxyanthraquinone, 302–304 1-hydroxy-2-(1-butoxymethyl)anthraquinone, 413 1-hydroxy-2-(1-propoxymethyl)anthraquinone, 419–420 1-hydroxy-2-(ethoxymethyl)anthraquinone, 414–415 1-hydroxy-2-(isobutoxymethyl)anthraquinone, 415–416 1-hydroxy-2-(methoxymethyl)anthraquinone, 416–417 1-hydroxy-4-(prop-2-enyloxy)anthraquinone, 417–418 1-hydroxy-8-(prop-2-enyloxy)anthraquinone, 418–419 1-hydroxyanthraquinone, 412–413 9,10-anthraquinone, 64–65 10-Anthraquinone, 9,10-Anthracenedione, 64–65 1,8-Dihydroxy-2-(prop-2 0 -enyl)anthrone, 308–309 1,4-Bis(prop-2 0 -enyloxy)anthraquinone, 1,4-bix(allyloxy)anthraquinone, 131–132 Anuidin, 277–278 Aquafen, 369 Arachidic acid, 337 Arachidonic acid ethyl ester, 65 (all Z)-5,8,11, 14-eicosatetraenoic acid ethyl ester, 65 ethyl arachidonate, 65 Arachidyl alcohol, 65, 338 1-eicosanol, 65 Aroclor, 66 PCB1254, 66 Artemisinin, 66–67 891

CAT4240—INDEX —6/11/2006—15:38—SRIDHAR—XML MODEL C – pp. 891–909

892 Ascorbic acid, 67 6-palmitate, asorbyl palmitate, 67 vitamin C, 67 Asorbyl palmitate, 67 ascorbic acid 6-palmitate, 67 L-ascorbic acid 6-hexadenanoate, 67 Aspirin, 26, 68–69 2-acetoxybenzoic acid, 68–69 acetylsalicylic acid, 68–69 salicylic acid mixture, 69 Atratone, 69 2-ethylamino-4-isopropylamino-6-methoxy-striazine, 69 Atrazine, 70–71 2-chloro-4-ethylamino-6-isopropylamino-striazine, 70–71 Atropine, 72 tropine tropate, 72 9-Azaanthracene, acridine, 26–29 9-Azaﬂurorene, carbazole, 166 Azobenzene, 73 diphenyldizene, 73

B BArF complex, 589 Barium bis(hexaﬂuorroacetylacetonte), 75 Beclomethasone-17, 21-dipropionate, 75–76 Beef shank fat, 76 Behenic acid, 77–80 docosanoic acid, 77–80 Behenyl behante, 81 docosyl docosanoate, 81 1,2-Benzophenanthrene, 203–205 Benzaldehyde C1-methylnaphthalene mixture, 82 Benzaldehyde, 81–82 benzoic aldehyde, 81–82 1,3-Benzenediol, 701–702 Benzeneacetic acid, 640 Benzenecarbonitrile, benzonitrile, 92 1,2-Benzenediol, 692–693 Benzenemethanol, benzyl alcohol, 93–95 Benzenepropanol, 641 Benzo[def]phenanthrene, 675–691 Benzo[ghi]perylene, 92–93 1,12-benzoperylene, 92–93 Benzo[j,k]ﬂuorene, 370 Benzocaine, 4-aminobenzoic acid ethyl ester, 82–84 Benzocaine, ethyl 4-aminobenzoate, 82–84 Benzoic acid, 84–90 mixture, 276, 529 hexamethylbenzene, 91 phenathrene and, 632

Solubility in Supercritical Carbon Dioxide Benzoic aldehyde, benzaldehyde, 81–82 Benzoin, 91 (G)-2-hydroxy-2-phenylacetophenone, 91 (G)-2-hydroxy-1,2-diphenylethanone, 91 Benzonitrile, 92 benzenecarbonitrile, 92 cyanobenzene, 92 1,12-Benzoperylene, Benzo[ghi]perylene, 92–93 2HK1-Benzopyran-2-one, 262–263 2,3-Benzopyrrole, 452 2,3-Benzoquinoline, acridine, 26–29 2-(Thiocyanatomethylthio)benzo[d]thiazole, 763 2-(Thiocyanomethylthio)benzothiazole, 763 2-Benzoylacetophenone, 384 Benzyl alcohol, 93–95 benzenemethanol, 93–95 Benzylbenzene, 329 Benzylpenicillin, 597 Betamethasone 17, 95 21-dipropionate, 95–96 9a-ﬂuoro-16b-methylprednisolone, 95 g-BHC, 473 BHC, 392–393 Bibenzyl 1,2-diphenylethane, 96 mixture, 530 1,1 0 -Biphenyl, biphenyl, 97–99 Biphenyl, 1,1 0 -biphenyl, 97–99 Bis (1,1,1,5,5,5-hexaﬂuoro-2,4-pentanedionato) barium, barium, 75 (1,1,1,5,5,5-hexaﬂuoro-2,4-pentanedionato) cobalt, 248 (1,1,1,6,6,6-hexaﬂuoropentane-2,4-dionato) copper, 253 (2,2,6,6-tetramethyl-3,5-heptanedionato) palladium, 588 (2,4-pentanedionato) lithium, 475 (2,4-pentanedionato) manganese dihydrate, 478 (2,4-pentanedionato) palladium, 587 (2,4-pentanedionato) zinc, 833 (2,4-pentanedionato)cobalt, 248 (2,4-pentanedionato)copper dehydrate, 252 (2,4-pentanedionato)copper, 251–252 (2,4-pentanedionato)platinum, 647 (2,6-dimethylheptane-3,5-dionato)copper, 253 (2-ethylhexyl) phosphate, 300 (2-ethylhexyl) phthalate, 326 (5,5-dimethylhexane-2-4-dionato)copper, 253 (8-methylnonyl) hydrogen phosphate, 311 (diisopropyldithiocarbamato) palladium, 589 (dissopropyldithiocarbamato)lead, 463–464 (methylthioglycolato) palladium, 587–588 (h5-cyclopentadienyl) iron, 351–354

CAT4240—INDEX —6/11/2006—15:38—SRIDHAR—XML MODEL C – pp. 891–909

Index Bisacodyl, 100 4,4 0 -(2-pyridylmethylene)bisphenol diacetate, 100 Bitumen cut 1, 136 cut 2, 137 cut 3, 137 Bitumen, 135–136 Black pepper essential oil, 138 Blackcurrant seed oil, 138 2-Bomanone, camphor, 159 Brassylic acid, 140 tridecanedioic acid, 140 Bromobenzene, 140 Buriti fruit, 817 1-Butanol, n-butanol, 141 Butyl 2,5-dichlorabenzoate, 145–146 2,5-dichlorobenzoic acid butyl ester, 145–146 acetate, 142–143 alcohol, n-butanol, 141 1,4-Bis(butylamino)anthraquinone, 101–104 C.I. solvent blue 35, 101–104 2-tert-butylphenol, 148–149 2-(1,1-dimethylethyl)phenol, 148–149

C C.I. disperse black 9, 205 blue CC.I. disperse yellow 16 mixture, 214 blue, 1,4-bis(methylamino)anthraquinone, 111–114 blue 3, 206 blue 14, 207 blue 27, 208 blue 60, 208–210 blue 60S, 210 blue 77, 211 blue 79, 211–212 blue 79:1, 213 blue 102, 213 blue 118, 214 blue 134, 1,4-bis(isopropylamino)anthraquinone, 110–111 blue 134, 214 blue 165:1, 215 blue 291, 215–216 blue 354, 216 brown 22, 217 dyes, 217 orange 11, 219 orange 25, 221

893 orange 3, 218 orange, 13, 220 orange 30, 221–222 orange 33, 223 red 1, 224–225 red 9, 225 red 11, 226–227 red 13, 227 red 30, 228 red 60, 228–233 red 82, 234 red 137, 234 red 152, 236 red 153, 236 red 167, 236 red 324, 236–237 red W-4BS, 237 violet 91, 238 yellow 7, 238 yellow 16, 239 yellow 42, 239 yellow 54, 240 yellow 82, 241 yellow 86, 241 yellow 108, 241 yellow 119, 242 food orange 5, b-carotene, 169–176 mordant brown, 243 red 11, 243 yellow 12, 243 solvent blue 14, 1,4-bis(pentylamino)anthraquinone, 128–130 blue 35, 245 blue 35, sudan blue II, 245 blue 35, 1,4-bis(butylamino)anthraquinone, 101–104 blue 105, 1,4-bis(ethylamino)anthraquinone, 106–108 brown 1, 246 orange, 301–302 yellow 7, 420 Cafestol, 151 Caffeic acid, 152 3,4-dihydroxybenzeneacrylic acid, 152 3,4-dihydroxycinnamic acid, 152 Caffeine, 152 1,3,7-trimethyl-2,6-dioxopurine, 152–158 1,3,7-trimethylxanthine, 152–158 Calciferol, 820–821 Calix[4]arene, 158 calix[4]arene-25,26,27,28-tetrol, 158 Camphor, 159 2-bornanome, 159

CAT4240—INDEX —6/11/2006—15:38—SRIDHAR—XML MODEL C – pp. 891–909

894 Canola oil, 160 Capric alcohol, 276 Caproic acid, 402–403 6-Caprolactam, 160–161 Capsaicin, 161–163 (E)-8-methyl-N-vanillyl-6-nonenamide, 161–163 Carbamazepine, 164–165 Carbazole, 166 9-azaﬂuorene, 166 dibenzopyrrole, 166 phenathrene and, 633 4-(Carbomethoxy)phenol, 502–503 Carbon dioxide saturated, vs. pressure, density of, 838–839 saturated, vs. temperature, density of, 836–737 single phase region, mol/l, density of, 840–854 supercritical, 2–3 Carbonyl-p-cyclopentadienyl(triphenylphosphine)cobalt, 168 Carbonyl-p-cyclopentadienyl(tris(4-trimethylsilyphenyl)phospine)cobalt, 168 2-Carboxyaniline, 2-Aminobenzoic acid, 34 3-Carboxypyridine, 555–557 2-Carboxypyrazine, 675 b-Carotene, 168–176 C.I. food orange 5, 169–176 Carvacrol, 176, 5-isopropyl-2-methylphenol, 176 (R)-(K)-Carvone, L-carvone, 177 Castor oil, 177 Catechaldehyde, 674 Catechin, 178 (C)-catechin, 178 Catechol, 692–693 Cavacrol, 5-isopropyl-o-cresol, 176 Cerium tetrakis (2,2,6,6-tetramethyl-3,5-heptanedionate), 178–179 (2,2,6,6-tetramethyl-3,5-heptanedionate), tetrakis(2,2,6,6-tetramethyl-3-5-heptanedionato)cerium, 178–179 (2,2,7-trimethyl-3,5-octanedionate), 179 (2,2,7-trimethyl-3,5-octanedionate), tetrakis(2,2,7-trimethyl-3,5-octanedionato)cerium, 179 Cetyl alcohol, 179–182 1-hexadecanol, 179–182 palmity alcohol, 179 behenate, 594 Chloramphenicol, 182 4,4 0 -DDT, 1,1-Bis(4-chlorophenyl)-2,2,2-trichloroethane, 134–135 4-Chlorobiphenyl, 186–190 4-Chlorophenol, 191

Solubility in Supercritical Carbon Dioxide 9a-Chloro-16b-methylprednisolone 17,21-dipropionate, Beclomethasone-17, 21-dipropionate, 75–76 Chlorobenzene, 183 2-Chlorobiphenyl, 183–186 2-Chloropyrimidine, 191 2-chloro-1,3-pyrimidine, 191 Cholecalciferol, 821–822 Cholest-5-en-3b-ol, 192–199 Cholesterol, 192–199 acetate, 199 cholesteryl acetate, 199 benzoate, 199–200 cholesteryl benzoate, 199–200 butanaoate, 201 butyrate, 201 cholesterol butanoate, 201 cholesteryl butyrate, 201 cholest-5-en-3b-ol, 192–199 progesterone and, 666 testosterone and, 201 Cholesteryl acetate, 199 benzoate, 199–200 butyrate, 201 Chromium cis-tris (1,1,1-triﬂuoroacetylacetonate), 203 (1,1,1-triﬂuoroacetylacetonate), cis-tris(1,1,1triﬂuoropentane-2,4-dionato)chromium, 203 (2,2,6,6-tetramethylheptane-3,5-dionate), 202 (2,2,6,6-tetramethylheptane-3,5-dionate), tris(2,2,6,6-tetramethylheptane-3,5-dionato)chromium, 202 (3-bromoacetylacetonate), 202 (3-bromoacetylacetonate), tris(3-bromopentane2,4-dionato)chromium, 202 (acetylacetonate) 202 (acetylacetonate), tris(pentane-2,4-dionato)chromium, 202 Chromium trans-tris (1,1,1-triﬂuoroacetylacetonate), 203 (1,1,1-triﬂuoroacetylacetonate), trans-Tris(1,1,1triﬂuoropentane-2,4-dionato)chromium, 203 Chrysene, 203–205 1,2-benzophenanthrene, 203–205 Cichlorophenol* 2,4-Dichlorophenol, 294 Cineole, 244 1,8-cineole, 244 1,8-epoxy-p-menthane, 244 cis-2-Pinen-4-ol, 818–819 cis-tris(1,1,1-triﬂuoropentane-2,4-dionato)chromium, 203 cis-Verbenol, 818–819 cisK2-Pinen-4-ol, 818–819

CAT4240—INDEX —6/11/2006—15:38—SRIDHAR—XML MODEL C – pp. 891–909

Index Citral, 246–247 3,7-dimethyl-2,6-octadienal, 246–247 Clove buds extract, 247 Cobalt bis(acetylacetonate), 248 bis(acetylacetonate), Bis(2,4-pentanedionato)cobalt, 248 bis(hexaﬂuoroacetylacetonate), 248 bis(hexaﬂuoroacetylacetonate), bis(1,1,1,5,5,5hexaﬂuoro-2,4-pentanedionato)cobalt, 248 tris(acetylacetonate), 248 tris(acetylacetonate), tris(2,4-pentanedionato) donato, 248 Cocoa butter, 249 Cod, 357 Codeine, 250 methylmorphine, 250 Coenzyme Q10, 251 Copper bis(1,1,1,6,6,6-hexaﬂuoracetylacetonate)hydrate, 254 bis(1,1,1,6,6,6-hexaﬂuoroacetylacetonate), 253 bis(1,1,1,6,6,6-hexaﬂuoroacetylacetonate), bis(1,1,1,6,6,6-hexaﬂuoropentane-2,4-dionato)copper, 253 bis(1,1,1,6,6,6-hexaﬂuoroacetylacetonate)hydrate, 254 bis(1,1,1-triﬂuoro-4-phenylbutane-2,4-dionate), 256 bis(1,1,1-triﬂuoroacetylacetonate), 255 bis(2,2,6,6-tetramethylheptane-3,5-dionate), 254 bis(2,2,6,6-tetramethylheptane-3,5-dionate), 255 bis(2,2,7-trimethyloctane-3,5-dionate), 256 bis(2,6-dimethylheptane-3,5-dionate), 253 bis(2,6-dimethylheptane-3,5-dionate), bis(2,6dimethylheptane-3,5-dionato)copper, 253 bis(5,5-dimethylhexane-2-4-dionate), 253 bis(5,5-dimethylhexane-2-4-dionate), bis(5,5dimethylhexane-2-4-dionato)copper, 253 bis(acetylacetonate) dihydratex, 252 bis(acetylacetonate) dihydratex, bis(2,4-pentanedionato)copper dehydrate, 252 bis(acetylacetonate), 251 bis(acetylacetonate), bis(2,4-pentanedionato) copper, 251–252 bis(thenoyltriﬂuoroacetonate), 255 dithiocarbamate complexes, 256–257 Copper(II) hydrogen arsenate, 257 Cortisol, 407 Cortisone acetate, 257–258 21-acetoxy-17a-hydroxypregn-4-ene-3,11,20trione, 258 Cortisone acetate, 257–258 Coumarin, 262–263 2H-1-benzopyran-2-one, 262–263

895 2-Courmaric acid, 258–259 3-Courmaric acid, 259–260 4-Courmaric acid, 260–262 4-Cresol, 263–264 Critical constants, supercritical ﬂuids and, 2 Cupuacu seed fate, 264 Cyanobenzene, benzonitrile, 92 2-Cyanonaphthalene, 264 2-naphthalenenitrile, 264 2-naphthonitrile, 264 1-Cyanooctadecane, 567 a-Cyclodextrin octadecaacetate, 2,3,6-triacetyl-acyclodextrin, 265 b-Cyclodextrin heneicosaacetate, 2,3,6-Triacetylb-cyclodextrin, 265 g-Cyclodextrin tetracosaacetate, 2,3,6-triacetylg-cyclodextrin, 266 1,5,9-Cyclododecatriene, 266 Cyclododecene, 266 Cyclohexanol, 267 Cyclohexanone, 267 Cyclopentadienyl metal complexes, 268 Cyclopentadienyl trimethylsilyl metal complexes, 268 Cyclopentadienylmanganese tricarbonyl, 268 tricarbonyl(h5-cyclopentadienyl) manganese, 268 Cyclotrimethylenetrinitramine, 269 1,3,5-trinitrohexahydro-s-triazine, 269 RDX, 269 Cyproterone acetate, 270

D D-(K)-Fructose,

380 380 D-Fructose, 380 1,8-Dihydroxyanthraquinone, danthron, 302–304 Danthron, 302–304 DDT, 1,1-Bis(4-chlorophenyl)-2,2,2-trichloroethane, 134–135 Decahydro 3,5,1,7-[1,2,3,4]butanetetrayinaphthalene, 278 Decahydronaphthalene, 271 Decalin, 271 decahydronaphthalene, 271 Decamethylene glycol, 275 Decane, 272–275 1,10-Decanediol, 275 benzoic acid mixture, 276 1-Decanol, 276 capric alcohol, 276 decyl alcohol, 276 Decyl alcohol, 276 2,5-dichlorobenzoate, 277 D-(K)-levulose,

CAT4240—INDEX —6/11/2006—15:38—SRIDHAR—XML MODEL C – pp. 891–909

896 9,10-Deepithio-9,10-didehydroacanthifolicin, 580 1,2-Dehydrocortisone, 663 1,2-Dehydrohydrocortisone, 663 Dextrose, 382–383 D-Glucopyranose pentaacetate, 599 D-Glucose pentaacetate, 599 Di-(2-ethylhexyl)phosphoric acid, 300 bis(2-ethylhexyl) phosphate, 300 Diacetoxyscirpenol, 277–278 12,13-epoxytrichothec-9-ene-3a, 4b, 15-triol 4,15-diacetate, 277–278 anuidin, 277–278 Diadamantane, 278 Diamantane, 278 decahydro 3,5,1,7-[1,2,3,4]butanetetrayinaphthalene, 278 diadamantane, 278 9,10-Diazaanthracene, 635 Diazepam, 278 Dibenzo -24-crown-8, 279–280 -27-crown-9, 280–281 -30-crown-10, 281–282 Dibenzofuran, 282–283 diphenylene oxide, 282–283 Dibenzopyrazine, 635 Dibenzopyrrole, carbazole, 166 Dibenzothiophene, 283 9-thiaﬂuorene, 283 diphenylene sulﬁde, 283 Dibenzoylmethane, 284 1,3-diphenyl-1,3-propanedione, 284 2-benzoylacetophenone, 384 Dicaprylyl ether, 326 4,4 0 -Dichloro-1,1 0 biphenyl, 289–293 4,4 0 -Dichlorobiphenyl, 289–293 4,4 0 -dichlorobiphenyl, 4,4 0 -Dichloro1,1 0 biphenyl, 289–293 0 4,4 -dichlorobiphenyl, PCB 15, 289–293 1,2-Dichlorobenzene, 285–286 2,5-Dichlorobenzoic acid butyl ester, butyl 2,5-dichlorabenzoate, 145–146 2,5-Dichlorobenzoic acid n-propyl ester 672 2,2 0 -Dichlorobiphenyl, 2,2 0 -Dichloro-1,1 0 -biphenyl, 289 2,2 0 -Dichlorobiphenyl, 286–289 Dichlorobis(triphenylphosphine)nickel(II), 293 2,4-Dichlorophenoxyacetic acid, 295–297 Diclofenac sodium, 297 sodium 2-(2,6-dichloranilino)phenyl, 297 Didodecanoyl glycerol, 311 Didodecylamine, 297 Didodecylphosphine, 298 Didodecylphosphine, dilaurylphosphine, 298 Didodecylsulfane, 298

Solubility in Supercritical Carbon Dioxide Didodecylthioether, 298 Didodecylthioether, didodecylsulfane, 298 Diethyl 1,2-benzenedicarboxylate, 300 methyl carbinol, 501 phthalate, 300 diethyl 1,2-benzenedicarboxylate, 300 phthalic acid diethyl ester, 300 Diethylamine diethyldithiocarbamate, 298–299 Diethylammonium diethyldithiocarbamate, diethylamine diethyldithiocarbamate, 299 Dihexyl (diethylcarbamoyl)methylphosphonate, 300 -(N,N-diethylcarbamoyl)methylphosphonate, 300 1,2-Dihydrocacenaphthylene, aceneaphthene, 19–20 1,3-Dihydroxybenzene, 701–702 1,4-Dihydroxyanthraquinone, 301–302 C.I. solvent orange 86, 301–302 quinizarin, 301 1,6-Dihydroxyxanthone, 309–310 6-7-Dihydroxycourmarin, aesculetin, 31 1,8-Dihydroxyanthrone, 1,8-Dihydroxyanthracen9(10H)-one, 304–305 Dihydroxybenzenes, 305 3,4-dihydroxybenzeneacrylic acid, caffeic acid, 152 2,5-Dihydroxybenzoic acid, 381 3,4-Dihydroxybenzoic acid, 675 3,4-Dihydroxycinnamic acid, caffeic acid, 152 7,8-Dihydroxyﬂavone, 306 Diiodomethyl p-toyl sulfone, 310 p-toyl diimodomethyl sulfone, 310 Diisodecyl phosphoric acid, 311 bis(8-methylnonyl) hydrogen phosphate, 311 Dilaurin, 311 didodecanoyl glycerol, 311 glycerol dilaurate, 311 Dilaurylamine, 297 Dilaurylphosphone, 298 1,2-Dimethoxybenzene, 2-Methoxyanisole, 311–312 1,4-Dimethoxybenzene 4-methoxyanisole, 312 hydroquinone dimethyl ether, 312 4-Dimethylaminoazobenzene, 313 Dimethyl 2HK1-benzopyran-2,3-dicarboxylate, 314 dimethyl 2H-chromene-2,3-dicarboxylate, 314 2H-chromene-2,3-dicarboxylate, 314 6-bromo-2H-1-benzopyran-2,3-dicarboxylate, 315 dimethyl 6-bromo-2H-chromene-2,3-dicarboxylate, 315 2,8-dimethyl-6H, 12HK5,11-methanodibenzo [b,f][1,5]diazocine, 807

CAT4240—INDEX —6/11/2006—15:38—SRIDHAR—XML MODEL C – pp. 891–909

Index 3,7-dimethyl-1, 6-octadien-3-ol, 472–473 3,7-dimethyl-2,6-octadienal, 246–247 Dimethyl-3H-naphtho[2,1-b]pyran-2,3-dicarboxylate, 320 2,5-Dimethylaniline 2,5-dimethylbenzenamine, 313–314 2,5-dimethylaniline, 2,5-Xylidine, 313–314 3-Dimethylanthraquinone, 1-Amino, 35–38 1-Amino-2, 3-dimethylanthraquinone, 35–38 1-Hydroxy-2,4-dimethylanthrone, 4-Hydroxy-1, 3dimethylanthrace-10(9H)-one, 437–438 2,3-Dimethylhexane, 2,3-dimethylnaphthalene C2,6-dimethylnaphthalene mixture, 317 2,3-dimethylnaphthalene mixture, phenathrene and, 633 2,3-dimethylnaphthalene, 315–317 2,3-dimethylnapthalene (2) mixture, 531 2,6-Dimethylnaphthalene (2) mixture, Phenathrene (1) and, 633 2,6-Dimethylnaphthalene, 318–320 2,6-Dimethylphenol, 829 2,6-Xylenol, 2,6-Dimethylphenol, 829 3,4-Dimethylphenol, 830 1,3-Dimethylxanthine, 760–762 3,7-Dimethylxanthine, 757–760 Di-n-dodecylamine, 297 dilaurylamine, 297 2,4-Dinitrophenol, 321–322 2,5-Dinitrophenol, 322–323 Dinonyl 1,2-benzenedicarboxylate, 324 phthalate, 323–325 Dioctyl ether, 325 dicaprylyl ether, 326 octyl ether, 326 Dioctyl phthalate, 326 bis(2-ethylhexyl) phthalate, 326 Diolein, 326 glycerol dioeate, 326 5,5-Diphenylhyclantoin, 641 1,3-Diphenyl-1,3-propanedione, 284 Diphenylamine, 327–329 N-phenylaniline, 327, 329 N-phenylbenzeneamine, 327 1,3-Diphenylbenzene, 739 Diphenyldiazene, azobenzene, 73 Diphenylene oxide, 282–283 sulﬁde, 283 Diphenylmethane, 329 benzylbenzene, 329 mixture, 532 Di-tert-butyl 3H-naphtho[2,1-b]pyran-2,3-dicarboxylate, 284–285

897 4,5-Diazaphenanthrene, 634 DL-a-Tocopherol, 766–769 DMDT, 489 1-Hydroxy-2,4-dimethylanthrone, 437–438 Docosahexaenoic acid ethyl ester, Ethyl docosahexaenoate, 330 Docosane, 331 Docosanoic acid, behenic acid, 77–80 Docosyl docosanoate, behenyl behante, 81 Dodecane, 331–332 Dodecanoic acid, 463 Dodecyl gallate, 332 gallic acid dodecyl ester, 332 1,4-Bis(dodecylamino)anthraquinone, 105–106 Dotriacontane, 332–334 D-Xylose, 830 (C)-xylose, 830 Dynamic method, 9–11 D-d-Tocopherol, 769–770

E Eﬂucimibe, 335–336 Eicosane, 336–337 Eicosanoic acid, 337 arachidic acid, 337 1-Eicosanol, 338 arachidyl alcohol, 65, 338 Eicosapentaenoic acid ethyl ester, 338–339 ethyl eicosapentaenoate, 338–339 Emodin, 339 1,3,8-trihydroxy-6-methylanthraquinone, 340 Endrin, 340 Epicatechin, 340–341 epicatechol, 340–341 Epicatechol, 340–341 Equation of states, 11–13 Ergocalciferol, 820–821 Ergosterol, 341–342 Erythromycin, 342 Esculetin, aesculetin, 31 b-Estradiol, 342–343 estra-1,3,5(10)-triene-3, 17-diol, 342–343 Estra-1,3,5(10)-triene-3, 17-diol, 342–343 1,2-Ethanediol, 343 a’Ethylenedinitrilodi-o-cresol, 707 Ethyl 4-aminobenzoate, benzocaine, 82–84 arachidonate, arachidonic acid ethyl ester, 65 centralite, 343 docosahexaenoate, 330 eicosapentaenoate, 338–339 esters ﬁsh oil and, 360–367 ﬁsh oil fatty acid, 367

CAT4240—INDEX —6/11/2006—15:38—SRIDHAR—XML MODEL C – pp. 891–909

898 hexadecanoate, 347 myristate, 345 myristic acid ethyl ester, 345 tetradecanoic acid ethyl ester, 345 octadecanoate, 348 oleate, 346 (Z)-9-octadecenoic acid ethyl ester, 346 oleic acid ethyl ester, 346 palmitate, 347 ethyl hexadecanoate, 347 palmitic acid ethyl ester, 347 Ethyl stearate, 348 ethyl octadecanoate, 348 stearic acid ethyl ester, 348 2-Ethyl-1-hexanol, 344 2-ethylhexanoic acid mixture, 345 2-Ethyl-1-hydroxyanthracen-9-(10H)-one, 439–440 a-Ethylcaproic acid, 344–345 1,4-Bis(ethylamino)anthraquinone, 106–108 C.I. solvent blue 105–108 2-chloro-4,6-bis(ethylamino)-1,3,5-triazine, 709 2-chloro-4-ethylamino-6-isopropylamino-striazine, atrazine, 70–71 2-thylamino-4-isopropylamino-6-methoxy-s-triazine, atratone, 69 2-ethylamino-4-isopropylamino-6-methylthio1,3,5-triazine, ametryne, 33 Ethylene glycol, 343 1,2-ethanediol, 343 2-Ethylhexanoic acid, 344–345 a-ethylcaproic acid, 344–345 Eucalyptus leaves extract, 348 Eugenol, 349 2-methoxy-4-(2-propenyl)phenol, 349 4-allyl-2-methoxyphenol, 349 Ewe’s milk fat, 349

F Fenchone, 351 1,3,3-trimethylnorcamphor, 351 Ferrocene, 351 bis(h5-cyclopentadienyl) iron, 351–354 iron bis(cyclopentadienide), 351–354 Ferulic acid, 354 3-(4-hydroxy-3-methoxyphenyl) acrylic acid, 354–356 4-hydroxy-3-methoxycinnamic acid, 354–356 Fish liver oil, cod, 357 orange roughy ﬁsh, 358 spiny dogﬁsh C deep sea shark, 359 spiny dogﬁsh, 358

Solubility in Supercritical Carbon Dioxide oil ethyl esters, 360–367 fatty acid ethyl ester, 367 urea fractionated, 368 sand eel, 359–360 Flavone, 368–369 2-phenyl-4-chromone, 368–369 Florfenicol, 369 aquafen, 369 9-Fluorenone, 377 ﬂuoren-9-one, 377 Fluoranthene, 370–372 benzo[j,k]ﬂuorene, 370 triphenylene (3), acenaphthene and, 21 Fluoren-2-amine, 2-Aminoﬂuorene, 38 Fluoren-9-one, 377 Fluorene, 372–376 2,2 0 -methylenebiphenyl, 372–376 anthracene mixture and, 377 2-Fluoro-a-methyl-4-biphenylacetic acid, 379 5-Fluoro-2,4-pyrimidinedione, 378 5-Fluorouracil, 378 5-ﬂuoro-2,4-pyrimidinedione, 378 9a-Fluoro-16b-methylprednisolone betamethasone, 95 Flurbiprofen, 378–379 2-ﬂuoro-a-methyl-4-biphenylacetic acid, 379 Flurbiprofen, 378–379 Frangulin A, 379 Fructose, 380 D-(K)-levulose, 380 D-fructose, 380 Fungal oil, 380

G b-D-Galactopyranose pentaacetate, 598 b-D-Galactose, 598 Gallic acid 3,5-dimethyl ether, 734 dodecyl ester, 332 methyl ester, 496 propyl ester, 673 Gallium tris(acetylacetonate), 381 tris(2,4-pentanedionato) gallium, 381 Gentisic acid, 381 2,5-dihydroxybenzoic acid, 381 5-hydroxysalicylic acid, 381 Ginger rhizomes extract, 382 glucose, 382–383 dextrose, 382 D-glucose, 382–383 Glycerin, 383–384 monolaurate, 510 monooleate, 510

CAT4240—INDEX —6/11/2006—15:38—SRIDHAR—XML MODEL C – pp. 891–909

Index tridecanoate, 773 tridodexanoate, 784 trihexanoate, 773 trilinoleate, 786 trimyristate, 786 trioctanoate, 774 trioleate, 789–793 tripalmitate, 793–795 tristerate, 806 tributyrate, 773 Glycerol, 383–384 dilaurate, 311 dioeate, 326 monododecanoate, 510 monooleate, 510 tributanoate, 773 tricaprate, 773 tricaproate, 77 tricaprylate, 774 trihexadecanoate, 793–795 trilaurate, 784 trilinoleate, 786 trioctadacanoate, 806 triolein, 789–793 tritetradecanoate, 786 1,2,3-propanetriol, 383–384 Glycine, 384 2-aminoacetic acid, 384 Grape seed oil, 385 Gravimetric method, 7–9 Griseofulvin, 385

H 1,4-Haphthalenedione, 545–546 1,4-Naphthoquinone, 1,4-Haphthalenedione, 545–546 Henicosane, 387 2,2 0 3,4,4 0 5,5 0 -heptachlorobiphenyl, 387–391 Heptacosone, 391 Heptadacane, 391 Heptadecyl methyl ketone, 567 g-1,2,3,4,4,6-Hexachlorocyclohexane, 473 Hexabromocyclododecane, 392 Hexacarbonylmolybdenum, 505 Hexachlorobenzene, 392–393 BHC, 392–393 perchlorobenzene, 392 2,2 0 ,3,3 0 ,4,4 0 -Hexachlorobiphenyl, 394 PCB 128, 394 2,2 0 ,4,4 0 ,5,5 0 -Hexachlorobiphenyl, 395–398 PCB 153, 395–398 Hexachloroethane, 398 perchloroethane, 398 Hexaconsane, 398–399

899 Hexadecane, 399–400 Hexadecanoic acid, 590–594 1-Hexadecanol, 179–182 4-(Hexadecylamino)-7-nitrobenz-2-oxa-1,3-diazole, 400 NBD-HAD, 400 N-hexadecyl-7-nitro-4-benzofurazanamine, 400 Hexadecyl docosanoate, 594 Hexadecylamino* 1,4-Bis(hexadecylamino)anthraquinone, 108–110 1-Butyl-3-methylimidazolium hexaﬂuorophosphate, 146–147 1-Butyl-3-methylimidazolium hexaﬂuorophosphate, ionic liquid[bmim][PF6], 146–147 2,6,10,15,19,23-Hexamethyltetracosane, 710–715 Hexamethylbenzene, 401–402 Hexanoic acid, 402–403 1-hexanoic acid, 402–403 caproic acid, 402–403 1-Hexanoic acid, 402–403 1-Hexanol, 403 n-hexyl alcohol, 403 3-Hexanol, 403–404 Hexatriacontane, 404–406 Hydrocortisone, 407 cortisol, 407 Hydroquinone, 407–411 1,4-benzenediol, 407–411 dimethyl ether, 312 p-quinone mixture, 411–412 2-Hydroxbenzoic acid methyl ester, 502 (G)-2-Hydroxycaproic acid, 441 2-Hydroxy-1-naphthaldehyde, 1-Formyl-2-napthol, 446 2-Hydroxy-2-phenylacetic acid, 477 3-Hydroxoxyﬂavone, 440 4 0 Hydroxyacetanilide, acetaminophen, 22–23 4-Hydroxy-1, 3-dimethylanthrace-10(9H)-one, 437–438 4-Hydroxy-3-methoxybenzaldehyde, 816–817 4-Hydroxy-3-methoxycinnamic acid, 354–356 4-Hydroxybenzoic acid ethyl ester, 435 4-hydroxybenzoic acid ethyl ester, 435 4-Hydroxybenzoic acid propyl ester, 673 4-Hydroxychromen-2-one, 436 4-Hydroxycinnamic acid, 260–262 4-Hydroxycoumarin, 436 4-Hydroxychromen-2-one, 436 4-Hydroxypyrimidine, 447 4(1H)-pyrimidone, 447 4-pyrimidone, 447 5-Hydroxysalicylic acid, 381 7-Hydroxy-4-methylcourmarin, 444 4-methylumbelliferone, 444 7-Hydroxychromen-2-one, 436–437

CAT4240—INDEX —6/11/2006—15:38—SRIDHAR—XML MODEL C – pp. 891–909

900 7-Hydroxycoumarin, 436–437 7-hydroxychromen-2-one, 436–437 8-Hydroxyquinoline, 447 8-quinolinol, 447 a-Hydroxybenzeneacetic acid, 477 17b-Hydroxyandrost-4-en-3-one, 739–741 2-Hydroxyanisole, 490 2-Hydroxybenzoic acid, 421–429 2-Hydroxycinnamic acid, 258–259 2-Hydroxyhexanoic acid, (G)-2-Hydroxycaproic acid, 441 2-Hydroxypropanoic acid, 461 3-(4-Hydroxy-3-methoxyphenyl) acrylic acid, 354–356 3-Hydroxycinnamic acid, 259–260 4-Hydroxy-3-methoxybenzoic acid, 815 1-Hydroxythioxanthone, 1-Hydroxy-9H-thioxanthen-9-one, 448 1-Hydroxyxanthone, 1-Hydroxy-9H-xanthen-9-one, 449 Hydroxyy* 4-Hydroxy-3,5-dimethoxybenzoic acid, 734

I Imipramine hydrochloride, 451 Indium tris(acetylacetonate), 451 tris(2,4-pentanedionato)indium, 451 1H-Indole, 452 Indole, 452 1H-indole, 452 2,3-benzopyrrole, 452 Iodoform, 783 Ionic liquid[bmim][PF4], 1-Butyl-3-methylimidazolium tetraﬂuoroborate, 147 Iron bis(cyclopentadienide), 351–354 Iron tris (2,2,6,6-tetramethyl-3, 5-heptanedionate), 454 (2,2,6,6-tetramethyl-3, 5-heptanedionate), tris(2,2,6,6-tetramethyl-3, 5-heptanedionato)iron, 454 (2,2,7-trimethyl-3,5-octanedionate, 454 tris(2,2,7-trimethyl-3,5-octanedionato)iron, 454 (acetylacetonate), 452–453 tris(2,4-pentanedionato)iron, 452–453 1,3-Isobenzofuranidione, 642 4-Isopropenyl-1-methyl-1-cyclohexene, 467–471 5-Isopropyl-2-methylphenol, carvacrol, 176 5-Isopropyl-o-cresol, cavacrol, 176 1,4-Bis(isopropylamino)anthraquinone, 110–111 C.I. disperse blue 134, 110–111 2,4-Bis(isopropylamino)-6-methylthio-1,3,5-triazine, 667–668 2-Chlor-4–6-bis(isopropylamino)-1,3-5-trazine, 671

Solubility in Supercritical Carbon Dioxide

J Jojoba bean oil, 455 wax, 455

K Keteprofen, 457–458 2-(3-benzoylphenyl)propionic acid, 457–458 m-benzoylhydratoropic acid, 457–458 Krytox dithiol, 458 picolyl amine, 459

L Lactic acid, 461 2-hydroxypropanoic acid, 461 Lariat ether carboxylic acid, 462 Lasalocid sodium salt, 462 L-Ascorbic acid 6-hexadenanoate, asorbyl palmitate, 67 Lauric acid, 463 dodecanoic acid, 463 L-carvone, 177 (R)-(K)-carvone, 177 (R)-(K)-p-mentha-6,8-dien-2-one, 177 Lead bis(dissopropyldithiocarbamate), 463–464 Lecithin S20, 464–465 Li(acac), 475 Lidocaine, 466 Limonene, 467–471 4-isopropenyl-1-methyl-1-cyclohexene, 467–471 citral, 471 linalool, 472 p-mentha-1,8-diene, 467–471 Linalool, 472–473 3,7-dimethyl-1, 6-octadien-3-ol, 472–473 Lindane, 473 gK1,2,3,4,4,6-hexachlorocyclohexane, 473 g-BHC, 473 Linoleic acid, 474 (Z,Z)-9,12-octadecadienoic acid, 474 Lipids, 475 Lithium acetylacetonate, 475 bis(2,4-pentanedionato) lithium, 475 li(acac), 475 L-Leucine, 465 4-methyl-L-norvaline, 465 L-Limonene, 470 (4S)-4-isopropenyl-1-methyl-1-cyclohexene, 470 (S)-(K)-mentha-1,8-diene, 470

CAT4240—INDEX —6/11/2006—15:38—SRIDHAR—XML MODEL C – pp. 891–909

Index L-Phenylalanine,

640 (S)-2-amino-3-phenylpropanoic acid, 640 3-phenyl-L-alanine, 640 L-Tryptophan, 808 (2S)-2-amino-3-(1H-indol-3-yl)propanoic acid, 808

M Madelic acid 2-hydroxy-2-phenylacetic acid, 477 a-hydroxybenzeneacetic acid, 477 Mandelic acid, 477 Manganese bis(acetylacetonate) dehydrate, 478 bis(2,4-pentanedionato) manganese digydrate, 478 tris(acetylacetonate), 478 tris(2,4-pentanedionato) manganese, 478 m-Anisamide, 486 m-Anisic acid, 488 m-Benzoylhydratoropic acid, 457–458 m-Coumaric acid, 259–260 3-courmaric acid, 259–260 3-hydroxycinnamic acid, 259–260 Medroxyprogesterone acetatem 478–479 17a-acetoxy-6a-methylprogesterone, 478–479 cyproterone acetate mixture, 479 Megestrol acetate, 480 17a-acetoxy-6-dehydro-6-methylprogesterone, 481 Menadione, 823 Menthol, 481–482 5-methyl-2-(1-methylethyl) cyclohexanol, 481–482 2-Mercaptopyrimidine, 483 2-pyrimidinethione, 483 pyrimidine-2-thiol, 483 Mercury dithiocarbamate complexes, 483 Metal diethyldithiocarbamate complexes, 484 b-diketone and metal dithiocarbamate complexes, 484 dithiocarbamate complexes, 485 triﬂuoroethyldithiocarbamates, 485 Methimazole, 485–486 1-methylimidazole-2-thiol, 486 Methoxphenylacetic acid, 491 2-Methoxy-4-(2-propenyl)phenol, 349 2-Methoxy-4,6-bis(isopropylamino)-1,3,5-triazine, 667 3-Methoxybenzamide, 486 m-anisamide, 486 3-Methoxybenzoic acid, 488 m-anisic acid, 488

901 4-Methoxyanisole, 312 4-Methoxybenzaldehyde, p-Anisaldehyde, 40 4-Methoxybenzamide, 486 p-anisamide, 486 4-Methoxybenzoic acid, 488 p-anisic acid, 41, 488 5-Methoxy-1H-indole, 489 5-Methoxy-1-tetralone, 491 5-Methoxyindole, 489 5-methoxy-1H-indole, 489 6-Methoxy-1-tetralone (1)C7-Methoxy-1-tetralone (2) mixture, 491 6-Methylcourmarin, 6-Methyl-2H-1-benzopyran2-one, 495–496 7-Methoxy-1-tetralone (1)C5-Methoxy-1-tetralone (2) mixture, 491 7-Methoxycourmarin, 489 methylumbelliferone, 489 2-Methoxyanisole, 311–312 Methoxybenzene, anisole, 42 1-methylnaphthalene (2) mixture, 43 2-Methoxybenzoic acid, 487 o-anisic acid, 487 Methoxychlor, 489 DMDT, 489 2-Methoxynapthalene, methyl-2-naphthyl ether, 490 2-Methoxynitrobenzene, 560 2-Methoxyphenol, 2-Hydroxyanisole, 490 3-Methylindole, 709 Methyl cyanide, acetronitrile, 25 gallate, 496 gallic acid methyl ester, 496 m-nitrobenzoate, 498 3-nitrobenzoic acid methyl ester, 498 oleate, 499–500 oleic acid methyl ester, 499 o-nitrobenzoate, Methyl p-nitrobenzoate mixture, 498 2-nitrobenzoic acid methyl ester, 498 p-nitrobenzoate, 4-Nitrobenzoic acid methyl ester, 498 salicylate, 501–502 2-hydroxbenzoic acid methyl ester, 502 (E)-8-Methyl-N-vanillyl-6-nonenamide, capsaicin, 161–163 2-Methyl-5-nitro-1H-imidazole-1-ethanol benzoate, 504 2-Methylanthracene, 493 2-Methylbenzoic acid, 494 2-Methylnaphthalene, 497 mixture, 532 3-Methyl-3-pentanol, 501 diethyl methyl carbinol, 501

CAT4240—INDEX —6/11/2006—15:38—SRIDHAR—XML MODEL C – pp. 891–909

902 3-Methylbenzoic acid, 494 4-Methyl-L-norvaline, 465 4-Methylbenzoic acid, 494 4-Methylphenol, 263–264 4-Methylumbelliferone, 444 5-Methyl-2-(1-methylethyl) cyclohexanol, 481–482 phenol, 765 6-Methylcourmarin, 495–496 Methyl-2-naphthyl ether, 490 1,4-Bis(methylamino)anthraquinone, 111–114 C.I. disperse blue 14, 111–114 1-Amino-2-methylanthraquinone, C.I. Disperse Orange 11, 39 2-Chloro-1-methylbenzene, 190 1,1 0 1 00 -Methylidynetrisbenzene, 798–800 1-Methylimidazole-2-thiol, 486 Methylmorphine, 250 1-Methylnaphthalene, 2-Methylnaphthalene mixture, 497 Methylparaben, 4-(Carbomethoxy)phenol, 502–503 17a-Acetoxy-6a-methylprogesterone, 478–479 17a-Acetoxy-6-dehydro-6-methylprogesterone, 481 (4 S)-4-Methylsalinomycin monosodium salt, 552–553 1,4-Dihydroxy-3-methylthioxanthone, 307 1-Hydroxy-3-methylthioxanthone, 444–446 1-Hydroxy-3-methylthixanthen-9-one, 444–446 Methylumbelliferone, 489 Metronidazole benzoate, 503–504 2-methyl-5-nitro-1H-imidazole-1-ethanol benzoate, 504 m-Hydroxybenzoic acid, 431–434 3-hydroxybenzoic acid, 431–434 p-hydroxybenzoic acid and, 431 Miconazole, 504 Milk fat triglyceride, 504 thistle seed oil, 505 m-Nitrophenol, 563–564 3-nitrophenol, 563–564 Modeling equation of states, 11–13 simple density correlation and, 13–15 solubility and, 11–15 Molecular formula, solutes by, 855–890 Molybdenumhexacarbonyl, 505 hexacarbonylmolybdenum, 505 Monensin sodium salt, 506 Monocrotaline, 506–509 Monolaurin, 510 glycerin monolaurate, 510 glycerol monododecanoate, 510

Solubility in Supercritical Carbon Dioxide Monoolein, 510–511 glycerin monooleate, 510 glycerol monooleate, 510 m-Terphenyl, 739 1,3-diphenylbenzene, 739 Myristic acid, 511–512 ethyl ester, 345 tetradecanoic acid, 511–512

N N-(4-Hydroxyphenyl)acetamide, acetaminophen, 22–23 N-(4-Methyl-2-pyrimidyl)sulfanilamide, 731 N,N 0 -Bis(4,6-di-tert-butylsalicylidene)ethylenediamine, tert-butyl-salen, 149 N,N 0 -Bis(salicylidene)-1,2-ethanediamine, 707 N,N-Dihexyl-1-hexanamine, 781 N,N-Dimethylindoaniline, 639 N,N-Diphenylbenzenamine, 795 N1-(2-Thiazoly)sulfanilamide, 733 N1-(4,6-Dimethyl-2-pyrimidinyl)sulfanilamide, 732 4-Naphthoquinone, 823 a-Naphthol, 534–536 1-naphthalenol, 534–536 1-naphthol, 534–536 b-naphthol mixture, 536 b-Naphthol 2-naphthalenol, 537–542 2-naphthol, 537–542 anthracene mixture, 543 phenanthrene mixture, 543–544 2-Naphthalenenitrile, 264 2-Naphthalenol, 537–542 Naphthalene, 513–529 2,3-dimethylnapthalene mixture, 531 2,5-xylenol mixture, 534 2,6-dimethylnaphtalene mixture, 531 2-methylnaphthalene mixture, 532 benzoic acid mixture, 529 biphenyl mixture, 530 diphenylmethane mixture, 532 phenanthrene mixture, 532–533 phenathrene and, 634 phenol mixture, 534 1-Naphthalenol, 534–536 2,4-Dichloro-1-naphthalenol, 294 1,4-Naphthoquinone, 545–546 p-naphthoquinone, 545–546 1-((4-Aminophenyl)azo)-2-naphthol, 40 1-Formyl-2-naphthol, 446 1-Naphthol, 534–536 2,4-Dichloro-1-naphthol, 2,4-dichloro-1naphthalenol, 294

CAT4240—INDEX —6/11/2006—15:38—SRIDHAR—XML MODEL C – pp. 891–909

Index 2,4-Dichloro-1-naphthol, 294 2-Naphthol, 537–542 b-Naphthol, 537–542 2-Naphthonitrile, 264 (S)-(C)-Naproxen, 547–552 Naproxen, (S)-(C)-Naproxen, 547–552 Naproxen, 547–552 Narasin sodium salt, 552–553 (4 S)-4-methylsalinomycin monosodium salt, 552–553 NBD-HAD, 400 N-Benzyloxycarbonyl-DL-aspartic acid, N-carbobenzoxy aspartic acid, 166 N-Benzyloxycarbonyl-DL-proline, N-carbobenzoxyproline, 167 n-Butanol, 141 1-butanol, 141 butyl alcohol, 141 n-octane mixture, 142 N-Carbobenzoxy aspartic acid, 166 N-benzyloxycarbonyl-DL-aspartic acid, 166 N-Carbobenzoxyproline, 167 N-benzyloxycarbonyl-DL-proline, 167 N-Carbobenzoxyvaline, 167 N-benzyloxycarbonyl-DL-valine, 167 N-Hexadecyl-7-nitro-4-benzofurazanamine, 400 n-Hexyl alcohol, 403 Nickel complex, 553–554 Nicotinic acid. 555–557 3-carboxypyridine, 555–557 3-pyridinecarboxylic acid, 555–557 Nifedipine, 558 Nimesulide, 558 Nimodipine, 559 Nitrendipine, 560 2-Nitro-N-phenylaniline, 563 3-Nitrobenzoic acid methyl ester, 498 3-Nitrophenol, 563–565 3-Nitrotoluene, 1-Methyl-3-nitrobenzene, 565 4-Nitrobenzoic acid methyl ester, 498 4-Nitrophenol, 565 2-Nitroanisole, 2-Methoxynitrobenzene, 560 2-nitroanisole, 560 9-Nitroanthracene (1)C2-Methyl anthracene (2) mixture, 562 9-Nitroanthracene, 561 1-Methyl-3-nitrobenzene, 565 2-Nitrobenzoic acid methyl ester, 498 2-Nitrodiphenylamine, 2-Nitro-N-phenylaniline, 563 n-Octadecyl alcohol, 725–726 n-Octane, 578 Nonacosane, 566 Nonadecanenitrile, 1-Cyanooctadecane, 567 Nonadecanenitrile, octadecyl cyanide, 567

903 2-Nonadecanone, 567 heptadecyl methyl ketone, 567 1-Nonanol, 568 nonyl alcohol, 568 Nonedecane, 566–567 Nonyl alcohol, 568 N-Phenylaniline, 327, 329 N-Phenylaniline, N-Phenylbenzenamine, 329 N-Phenylbenzeneamine, 327

O o-, m- & p- Methoxphenylacetic acid, 491 o-Anisic acid, 487 o-Coumaric acid, 258–259 2-courmaric acid, 258–259 2-hydroxycinnamic acid, 258–259 Octacosane, 569–574 (Z,Z)-9,12-Octadecadienoic acid, 474 Octadecane, 574–575 1-Octadecanethiol, 578 Octadecanoic acid, 716–724 1-Octadecanol, 575–578, 725–726 (Z)-9-Octadecenoic acid, 580–583 ethyl ester, 346 Octadecyl cyanide, 567 1,4-Bis(octadecylamino)anthraquinone, 114–116 Octadecylmercaptan, 578 1-octadecanethiol, 578 stearyl mercaptan, 578 Octane, 578 Octyl 2,5-dichlorobenzoate, 579 ether, 326 pentaethylene glycol ether, 607–608 (phenyl)(N,N-diisobutylcarbamoyl)methylphosphine oxide, 579 1,4-Bis(octylamino)anthraquinone, 116–128 Octylpentaglycol, 607–608 o-hydroxybenzoic acid, 421–420 2-hydroxybenzoic acid, 421–429 m-hydroxybenzoic acid mixture, 429–430 m-hydroxybenzoic acid, p-hydroxybenzoic acid mixture, 431 p-hydroxybenzoic acid mixture, 430 salicylic acid, 421–429 Okadaic acid, 580 9,10-deepithio-9,10-didehydroacanthifolicin, 580 Oleic acid, 580–583 (Z)-9-octadecenoic acid, 580–583 ethyl ester, 346 methyl ester, 499 olive oil mixture, 583 Olive oil, 583

CAT4240—INDEX —6/11/2006—15:38—SRIDHAR—XML MODEL C – pp. 891–909

904 Orange peel oil, 584–585 roughy ﬁsh, 358 Oxacyclhexadecan-2-one, 607, 809

P p-Acetoxyacetanilide 4 0 -acetoxyacetanilide, 25–26 4-acetamidophenyl acetate, 25–26 Paclitaxel, 735 Palladium bis(2,2,6,6-tetramethyl-3,5-heptanedionate), 588 bis(2,2,6,6-tetramethyl-3,5-heptanedionato) palladium, 588 bis(acetylacetonate), 587 bis(2,4-pentanedionato) palladium, 587 bis(diisopropyldithiocarbamate), 589 bis(diisopropyldithiocarbamato) palladium, 589 bis(methylthioglycolate), 587–588 bis(methylthioglycolato) palladium, 587–588 diimine BArF complex, 589 Palm kernel oil 595 oil, 595–596 Palmitic acid 590–594 ethyl ester, 347 hexadecanoic acid, 590–594 Palmityl alcohol, 179 behenate, 594 cetyl behenate, 594 hexadecyl docosanoate, 594 p-Anisaldehyde, 40 4-methoxybenzaldehyde, 40 p-Anisamide, 486 p-Anisic acid, 41, 488 4-methoxybenzoic acid, 41 Para red, 596–597 C.I. pigment red 1, 596–597 PCB 15, 70, 77, 153, 289, 395–398, 743–747, PCB1254, Aroclor, 66 p-Chlorophenol, 191 4-chlorophenol, 191 p-Coumaric acid, 4-courmaric acid, 260–262 4-hydroxycinnamic acid, 260–262 p-Cresol, 4-cresol, 263–264 4-methylphenol, 263–264 p-Dimethylaminoazobenzene, 313 4-dimethylaminoazobenzene, 313 1,2,3,4,6-Penaacetyl-d-galactose, b-D-galactose, 598 b-D-galactopyranose pentaacetate, 598

Solubility in Supercritical Carbon Dioxide 1,2,3,4,6-Pentaacetyl-d-glucose, 599 Penicillin G, 597 benzylpenicillin, 597 Penicillin V, 598 phenoxymethylpenicillin, 598 1,2,3,4,6-Penaacetyl-d-galactose, 598 1,2,3,4,6-Pentaacetyl-d-glucose D-glucopyranose pentaacetate, 599 D-glucose pentaacetate, 599 Pentachlorophenol, 603–605 Pentacosane, 605 Pentadecaﬂuorooctyl 2,5-dichlorobenzoate, 606 1-Pentadecanol, 606 Pentadecanolactone, 607 15-pentadecanolide, 607 oxacyclhexadecan-2-one, 607 15-Pentadecanolide, 607 Pentaethylene glucol n-octyl ether, 607–608 octyl pentaethylene glycol ether, 607–608 octylpentaglycol, 607–608 Pentaﬂuorobutyl 2,5-dichlorobenzoate, 608 Pentaﬂuoropropyl 2,5-dichlorobenzoate, 608 Pentahydroxy* 3,3 0 ,4 0 ,5,7-Pentahydroxyﬂavone, 609, 695 1,4-Bis(pentylamino)anthraquinone, 128–130 C.I. solvent blue 14, 128–130 Perchlorobenzene, 392 Perchloroethane, 398 a-Perylene, 609–611 Perylene, 609–611 dibenz[de,kl] anthracene, 609–611 a-perylene, 609–611 Pesticides, 612 2,2 0 ,4,5,5 0 -Pentachlorobiphenyl, 599–602 1,10-Phenanthroline, 4,5-Diazaphenanthrene, 634 1,10-Phenanthroline, 634 Phenathrene, 532–533 2,3-dimethylnaphthalene mixture, 633 2,6-dimethylnaphthalene mixture, 633 anthracene mixture, 632 benzoic acid mixture, 632 carbazole mixture, 633 naphthalene mixture, 634 Phenazine, 635 9,10-diazaanthracene, 635 dibenzopyrazine, 635 Phenol, 636–638 2-(1,1-dimethylethyl)phenol, 2-tert-butylphenol, 148–149 4-(phenylazo)phenol, 420 blue, 638–639 N,N-dimethylindoaniline, 639 mixture, 534

CAT4240—INDEX —6/11/2006—15:38—SRIDHAR—XML MODEL C – pp. 891–909

Index Phenoxymethylpenicillin, 598 Phenthrene, 612–631 (E)-3-Phenyl-2-propenoic acid, 245 2-Phenyl-4-chromone, 368–369 3-Phenyl-1-propanol, 641 3-Phenyl-1-propanol, Benzenepropanol, 641 3-Phenyl-L-alanine, 640 Phenylacetic acid, 640 benzeneacetic acid, 640 phenylethanoic acid, 640 Phenylethanoic acid, 640 (S)-2-Amino-3-phenylpropanoic acid, 640 Phenytoin, 641 5,5-diphenylhyclantoin, 641 Phosphoric acid tributyl ester, 771–772 triphenyl ester, 801 1,3-Phtalandione, 642 Phtalic anhydride, 642 1,3-isobenzofurandione, 642 1,3-phthalandione, 642 Phthalic acid diethyl ester, 300 p-Hydroxyazobenzene 4-(phenylazo)phenol, 420 C.I. solvent yellow 7, 420 p-Hydroxybenzoic acid, 434–435 4-hydroxybenzoic acid, 434–435 Phylloquinone, 822 Phytomenadione, 822 Picric acid, 642–643 2,4,6-trinitrophenol, 643 a-Pinene, 643–646 2-pinene, 643–646 2-Pinene, 643–646 (S)-Boc-Piperazine, 139 (S)-tert-butyl 3-(tert-butylcarbamoyl)piperazine1-carboxylate, (S)-Boc-Piperazine, 139 (S)-Boc-Piperazine, (S)-tert-butyl 3-(tert-butylcarbamoyl)piperazine-1-carboxylate, 139 Piroxicam, 646 Platinum bis(acetylacetonate), 647 bis(2,4-pentanedionato)platinum, 647 p-Mentha-1,8-diene, 467–471 p-Naphthoquinone, 545–546 p-Nitrophenol, 4-Nitrophenol, 564–565 Poly (1,1-digydroperﬂuorooctyl acrylate) 647–648 (ethyl vinyl ether), 655 (ethylene glycol) dimethylether, 650 diol, 651 monomethylether, 652–653 (ethylene glycol-block-propylene glycol, 649–650 (ethylene glycol-ran-propylene glycol), 654

905 (b-hydroxybutyrate), 656–657 (FOEMA-co-PPGMA), 655–656 (methyl methacrylate), 658 (propylene glycol) diol, 658–659 monobutylether, 660–661 (tetraﬂuoroethylene-co-vinyl acetate), 661–662 (vinyl butyral), 662 Polyethylene glycol, 648–649 Polymers, 657 p-Quinone, 696–697 Prednisolone, 662–663 1,2-dehydrohydrocortisone, 663 Prednisone, 663 1,2-dehydrocortisone, 663 Pregn-4-ene-3, 20-dione, 664–665 Procaine, 2-(Diethylamino)ethyl-4-aminobenzoate, 664 Progesterone, 664–665 cholesterol mixture, 666 pregn-4-ene-3, 20-dione, 664–665 testosterone mixture, 666 Prometone, 667 2-methoxy-4,6-bis(isopropylamino)-1,3,5triazine, 667 Prometryne, 667–668 2,4-bis(isopropylamino)-6-methylthio-1,3,5triazine, 667–668 1,2-Propanediol, 669 propylene glycol, 669 1,2,3-Propanetriol, 383–384 (2S)-2-Amino-3-(1H-indol-3-yl)propanoic acid, 808 1-(Isopropylamino)-3-(1-napthyloxy)-2-propanol, 672 1-Propanol, 669–670 2-Propanol, 670 Propazine, 671 2-chlor-4-6-bis(isopropylamino)-1,3-5-trazine, 671 2-(3-Benzoylphenyl)propionic acid, 457–458 Propranolol, 671–672 1-(isopropylamino)-3-(1-napthyloxy)-2-propanol, 672 Propyl 2,5-dichlorobenzoate, 2,5-dichlorobenzoic acid npropyl ester 672 4-hydroxybenzoate, 4-hydroxybenzoic acid propyl ester, 673 gallate, 673 gallic acid propyl ester, 673 Propylene glycol, 669 Protocatechualdehyde, 674 catechaldehyde, 674 Protocatechuic acid, 674–675 3,4-dihydroxybenzoic acid, 675

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906 p-tert-butylcalix[4]arene, 143 p-tert-butylcalix[6]arene, 144 p-tert-butylcalix[7]arene, 144–145 p-toyl diimodomethyl sulfone, 310 Pyrazinamine, 2-aminopyrazine, 40 Pyrazine-2-carboxylic acid, 675 2-carboxypyrazine, 675 2-pyrazinoic acid, 675 2-Pyrazinoic acid, 675 Pyrene, 675–691 benzo[def]phenanthrene, 675–691 3-Pyridinecarboxylic acid, 555–557 4-Pyrimidone, 447 4(1H)-Pyrimidone, 447 2,4-Pyrimidinedione, 810 2-Chloro-1,3-pyrimidine, 191 Pyrimidine-2-thiol, 483 2-Pyrimidinethione, 483 Pyrocatechol, 692–693 1,2-benzenediol, 692–693 catechol, 692–693

Q Quercetin, 695 3,3 0 ,4 0 ,5,7-Pentahydroxyﬂavone, 695 Quinizarin, 301 8-Quinolinol, 447

R rac-Boc-Piperazine, 139 Rape seed oil, 699–700 RDX, 269 Reserpine, 701 Resorcinol, 701–702 1,3-benzenediol, 701–702 1,3-dihydroxybenzene, 701–702 Resveratrol, 702 (E)-resveratrol, 702 3,4 0 ,5-stilbenetriol, 702 Retinol, 703 all-trans-retinol, 703 hexadecanoate, 819 vitamin A, 703 Rhodium tris(2,2,6,6-tetramethyl-3,5-heptanedionate), 705 tris(2,2,6,6-tetramethyl-3,5-heptanedionato) rhodium, 704–705 tris(diisopropyldithiocarbamate), 703–704 tris(methylthioglycoalate), 704 tris(methylthioglycolato)rhodium, 704 Rosemary oil, 705

Solubility in Supercritical Carbon Dioxide

S Saccharose, 728 Safety data, supercritical ﬂuids and, 2 Salen, 707 N,N 0 -bis(salicylidene)-1,2-ethanediamine, 707 a, a’ethylenedinitrilodi-o-cresol, 707 Salinomycin sodium salt, 707 Sand eel, 359–360 Saturated carbon dioxide vs. pressure, density of, 838–839 vs. temperature, density of, 836–837 Shale oil, 708 Simazine, 708–709 2-chloro-4,6-bis(ethylamino)-1,3,5-triazine, 709 Simple density correlation, 13–15 Skatole, 709 3-methylindole, 709 Sodium 2-(2,6-dichloranilino)phenyl, 297 Solubility, 3–5 Solubility measurement of, analytical method, 5 dynamic method, 9–11 gravimetric method, 7–9 static method, 5 synthetic method, 6–7 modeling equation of states, 11–13 simple density correlation, 13–15 supercritical carbon dioxide and, measurement of, 5–11 modeling of, 11–15 Solutes by molecular formula, 855–890 Soybean oil, 709 Spiny dogﬁsh, 358 deep sea shark, 359 Squalane, 710–715 2,6,10,15,19,23-hexamethyltetracosane, 710–715 Static method, 5 Stearic acid, 716–724 ethyl ester, 348 octadecanoic acid, 716–724 Stearyl alcohol, 725–726 1-octadecanol, 725–726 n-octadecyl alcohol, 725–726 mercaptan, 578 Stigmasterol, 726–728 (3b,22E)-sigmasta-5,22-dien-3-ol), 726–728 3,4 0 ,5-Stilbenetriol, 702 (C)-Sucrose, 728 Sucrose (C)-sucrose, 728 saccharose, 728 Sudan blue II, 245

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Index Sulfadimethoxine, 730–731 Sulfamerazine, 731 N-(4-methyl-2-pyrimidyl)sulfanilamide, 731 Sulfamethazine, 732 N1-(4,6-dimethyl-2-pyrimidinyl)sulfanilamide, 732 Sulfathiazole, 733–734 2-(sulfanilylamino)thiazole, 733–734 N1-(2-thiazoly)sulfanilamide, 733 Supercritical carbon dioxide, 2–3 solubility, 3–5 measurement of, 5–11 modeling of, 11–15 ﬂuids, critical constants, safety data, 2 ﬂuids, technology, 1–16 Surfactant Ls-36, 729 Ls-45, 729 Ls-54, 730 Synthetic method, 6–7 Syringic acid, 734 4-acid, 734 gallic acid 3,5-dimethyl ether, 734

T Taxol, 735 paclitaxel, 735 Tebuconazole, 736–737 Terbium tris(2,2,6,6-tetramethyl-3,5-heptanedionate), 737 tris(2,2,6,6-tetramethyl-3,5-heptanedionato)terbium, 737 tris(2,2,7-trimethyl-3,5-octanedionate), 738 Tert-butyl-salen, 149 N,N 0 -bis(4,6-di-tert-butylsalicylidene)ethylenediamine, 149 Testosterone 739–741 17-propionate, 17b-(1-oxopropoxy)-androst4-en-3-one, 741–742 17b-hydroxyandrost-4-en-3-one, 739–741 mixture, progesterone and, 666 a-Tetralol, 1,2,3,4-Tetrahydro-1-naphthol, 754–755 2,2 0 6,6 0 -Tetrabromobisphenol A, 742 Tetrabromobisphenol-A, 2,2 0 6,6 0 -Tetrabromobisphenol A, 742 3,3 0 ,4,4 0 -Tetrachlorobiphenyl, 743–747 PCB 77, 743–747 2,3 0 ,4 0 ,5-Tetrachlorobiphenyl, 743 PCB 70, 743 2,3,4,5-Tetrachlorophenol, 748 Tetracosane, 749–751 Tetradecanoic acid, 511–512 ethyl ester, 345

907 Tetraethylene glycol monododecyl ether, 756 1-Butyl-3-methylimidazolium tetraﬂuoroborate, 147 ionic liquid[bmim][PF4], 147 1,2,3,4-Tetrahydro-1-naphthol, 754–755 1,2,3,4-Tetrahydronaphtalene, 752–753 Tetrakis(2,2,6,6-tetramethyl-3-5-heptanedionato) cerium cerium tetrakis(2,2,6,6-tetramethyl-3,5-heptanedionate), 178–179 cerium tetrakis(2,2,7-trimethyl-3,5-octanedionate), 179 5,10,15,20-Tetrakis(3,5-bis(triﬂuoromethyl)phenyl)porphyrin, 751 5,10,15,20-Tetrakis(pentaﬂuorophenyl)porphyrin, 752 Tetralin, 752–753 1,2,3,4-tetrahydronaphtalene, 752–753 Theobromine, 757–760 3,7-dimethylxanthine, 757–760 Theophylline, 760–762 1,3-dimethylxanthine, 760–762 9-Thiaﬂuorene, 283 Thiamphenicol, 762 2-(sulfanilylamino)thiazole, 733–734 9-Thioxanthone, 764 1-Hydroxy-9H-thioxanthen-9-one, 448 Thioxanthen-9-one, 764 Thioxanthone, 764 9-thioxanthone, 764 thioxanthen-9-one, 764 Thymol, 765 5-methyl-2-(1-methylethyl)phenol, 765 Titanocene dichloride, 765 dichlorobis(h5-cyclopentadienyl) titanium, 765 TNT, 787 a-Tocopherol, 766–769 DL-a-Tocopherol, 766–769 vitamin E, 766–769 d-Tocopherol, D-d-Tocopherol, 769–770 trans-3-phenylacrylic acid, 245 Trans-cinnamic acid, 245 (E)-3-phenyl-2-propenoic acid, 245 trans-3-phenylacrylic acid, 245 Trans-Tris(1,1,1-triﬂuoropentane-2,4-dionato) chromium, 203 2,3,6-Triacetyl a-cyclodextrin, 265 b-cyclodextrin, 265 g-cyclodextrin, 266 Triacontane, 771 Tributanoin, 773 Tributyin, tributanoin, 773 Tributyl phosphate, 771–772 phosphoric acid tributyl ester, 771–772

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908 Tributyrin, 773 glycerine tributyrate, 773 glycerol tributanoate, 773 Tricaprin, 773 glycerin tridecanoate, 773 glycerol tricaprate, 773 tridecanoin, 773 Tricaproin glycerin trihexanoate, 774 glycerol tricaproate, 77 Tricaprylin, 774 glycerin trioctanoate, 774 glycerol tricaprylate, 774 trioctanoin, 774 Tricaprylylamine, 788 Tricarbonyl(h5-cyclopentadienyl) manganese, 268 1,1-Bis(4-chlorophenyl)-2,2,2-trichloroethane, 134–135 1,1,1-trichloro-2,2-bis(4-chlorophenyl)ethane, 134–135 1,1,1-trichloro-2,2-bis(4-chlorophenyl)ethane, 1,1-bis(4-chlorophenyl)-2,2,2Trichloroethane, 134–135 Trichlorobyphenyl* 2,4 0 ,5-Trichlorobiphenyl, 774–778 1,1-Bis(4-chlorophenyl)-2,2,2-trichloroethane, DDT, 134–135 1,1-Bis(4-chlorophenyl)-2,2,2-trichloroethane, 4,4 0 -DDT, 134–135 Tricyclo[3.3.1.13,7]decane, adamantane, 31 Tridecaﬂuorooctyl 2,5-dichlorobenzoate, 778 Tridecanedioic acid, brassylic acid, 140 Tridecanoin, 773 1-Tridecanol, 779 tridecyl alcohol, 779 Tridecyl alcohol, 779–780 Tridodecanoin, 784 Triethylene glycol, 779–780 triglycol, 779–780 Triglycerides, 780–781 Triglycol, 779–780 Trihexylamine, 781 N,N-dihexyl-1-hexanamine, 781 1,5,6-Trihydroxyxanthen-9-one, 782–783 1,5,6-trihydroxyxanthen-9-one, 782–783 1,5,6-trihydroxyxanthone, 782–783 Triiodomethane, 783 iodoform, 783 Trilaurin, 784 glycerin tridodexanoate, 784 glycerol trilaurate, 784 tridodecanoin, 784 trimyristin mixture, 785 tripalmitin mixture, 785

Solubility in Supercritical Carbon Dioxide Trilinolein, 786 glycerin trilinoleate, 786 1,3,7-Trimethyl-2,6-dioxopurine, caffeine, 152–158 1,3,7-Trimethylxanthine, caffeine, 152–158 1,3,3-Trimethylnorcamphor, 351 1,3,5-Trimitrohexahydro-s-triazine, 269 Trimyristin, 786 glycerin trimyristate, 786 glycerol tritetradecanoate, 786 2,4,6-Trinitroltoluene, 787 Trinitrololuene, 2,4,6-Trinitrotoluene, 787 2,4,6-Trinitrophenol, 643 Trinitrotoluene, 787 TNT, 787 Tri-n-octylamine, 788 Tri-n-octylphosphine oxide,788 Trioctanoin, 774 Trioctylamine, 788 tricaprylylamine, 788 tri-n-octylamine, 788 Trioctylphosphine, 788 tri-n-octylphosphine, 788 Triolein, 789–793 glycerin trioleate, 789–793 glycerol triolein, 789–793 Tripalmitin, 793–795 glycerin tripalmitate, 793–795 glycerol trihexadecanoate, 793–795 mixture trilaurin and trimyristin and, 785 trilaurin and, 785 trimyristin and, 786 Triphenylamine, 795 N,N-diphenylbenzenamine, 795 Triphenylene, 795–797 Triphenylmethane, 797–800 1,1 0 1 00 -methylidynetrisbenzene, 798–800 Triphenylphosphate, 801 phosphoric acid triphenyl ester, 801 Triphenylphosphine, 801–802 triphenylphosphorus, 801–802 Triphenylphosphorus, 801–802 Tristearin, 806 glycerin tristearate, 806 glycerol trioctadacanoate, 806 Tritriacontane, 806–807 Troctylphosphine oxide, 788 tri-n-octylphosphine oxide,788 Troeger’s base, 807 2,8-dimethyl-6H, 12H-5,11-methanodibenzo[b,f] [1,5]diazocine, 807 Tropine tropate, atropine, 72 Turmeric oil, 808

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Index

U Ubiquinone, 10 Undecanol, 809 undecyl alcohol, 809 Undecanolide, 809, 11-undecanolactone, 809 oxacyclododeacan-2-one, 809 Undecyl alcohol, 809 Uracil, 810 2,4-pyrimidinedione, 810 Uranyl bis(thenoyltriﬂuoroacetonate) Phosphate (X) Complex, 810–811 bis(triﬂuoracetylacetonate) Pyridine Complex, 811 dinitrate Tributyl phosphate complex, 812–813 thenoyltriﬂuoroacetylacetonate Tributyl phosphate complex, 813 Urea fractionated, ﬁsh oil fatty acid ethyl ester, 368

V Vanillic acid, 815–816 4-hydroxy-3-methoxybenzoic acid, 815 Vanillin, 816–817 4-hydroxy-3-methoxybenzaldehyde, 816–817 Vegetable oil from Buriti fruit, 817 Vitamin A, 703 palmitate, 819 all-trans-retinol palmitate, 819 retinol hexadecanoate, 819 Vitamin C, ascorbic acid, 67 Vitamin D2, 820–821 calciferol, 820–821 cholecalciferol, 821–822 ergocalciferol, 820–821 Vitamin E, 766–769

909 Vitamin K1, 822–823 phylloquinone, 822 phytomenadione, 822 Vitamin K3 2-methyl-1,4-naphthoquinone, 823 menadione, 823

W Water, 825–827 Wax, 827 Wool wax, 828

X 1-Hydroxy-9H-xanthen-9-one, 449 2,5-Xylenol, 829 mixture, 534 2,6-Xylenol, 829 3,4-Xylenol, 830 3,4-dimethylphenol, 830 2,5-Xylidine, 313–314 (C)-Xylose, 830

Y Yttrium tris(acetylacetonate), 831 tris(2,4-pentanedionato)yttrium, 831 tris(acetylacetonato)yttrium, 831 tris(hexaﬂuoroacetylacetonate), 831 tris(1,1,1,5,5,5-hexaﬂuoro-2,4-pentanedionato) yttrium, 831

Z Zinc bis(acetylacetonate), 833 bis(2,4-pentanedionato) zinc, 833 dithiocarbamate complexes, 833 Zopicione, 834

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