Group contribution values for the thermodynamic functions of hydration of aliphatic esters at 298.15 K, 0.1 MPa

Journal of Chemical and Engineering Data

Volumn 49, Issue 5, 2004, Pages 1152-1167

  Plyasunov, Andrey V ^a   Plyasunova, Natalia V ^a   Shock, Everett L ^a  

^a ARIZONA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALIPHATIC HYDROCARBONS; DILUTION; GROUP CONTRIBUTIONS; MONOHYDRIC ALCOHOLS;

ADDITIVES; CARBON; DATABASE SYSTEMS; FUNCTIONS; GIBBS FREE ENERGY; HYDRATION; LEAST SQUARES APPROXIMATIONS; NUMERICAL METHODS; THERMODYNAMICS;

ESTERS;

EID: 4644330068     PISSN: 00219568     EISSN: None     Source Type: Journal    
DOI: 10.1021/je049850a     Document Type: Review

References (177)

1. Benson, S.W. Thermochemical Kinetics; John Wiley & Sons: New York, 1976.
2. Domalski, E. S.; Hearing, E. D. Estimation of the Thermodynamic Properties of C-H-N-O-S-Halogen Compounds at 298.15 K. J. Phys. Chem. Ref. Data 1993, 22, 805-1159.
3. Lin, S.-T.; Sandler, S. I. Henry's Law Constant of Organic Compounds in Water from a Group Contribution Model with Multipole Corrections. Chem. Eng. Sci. 2002, 57, 2727-2733.
4. Hovorka, S.; Dohnal, V.; Roux, A. H.; Roux-Desgranges, G. Determination of Temperature Dependence of Limiting Activity Coefficients for a Group of Moderately Hydrophobic Organic Solutes in Water. Fluid Phase Equilib. 2002, 201, 135-164.
5. Cabani, S.; Gianni, P.; Mollica, V.; Lepori, L. Group contributions to the thermodynamic properties of nonionic organic solutes in dilute aqueous solution. J. Solution Chem. 1981, 10, 563-595.
6. Plyasunov, A. V.; Shock, E. L. Thermodynamic functions of hydration of hydrocarbons at 298.15 K and 0.1 MPa. Geochim. Cosmochim. Acta 2000, 64, 439-468.
7. Lin, S.-T.; Sandler, S. I. Multipole corrections to account for structure and proximity effects in group contribution methods: octanol-water partition coefficients. J. Phys. Chem. A 2000, 104, 7099-7105.
8. Guthrie, J. P. Additivity schemes permitting the estimation of partial molar heat capacities of organic compounds in aqueous solution. Can. J. Chem. 1977, 55, 3700-3706.
9. Domalski, E. S. Estimation of enthalpies of formation of organic compounds at infinite dilution in water at 298.15 K. A pathway for estimation of enthalpies of solution. ACS Symposium Series 1998, 677(Computational Thermochemistry), 47-62.
10. Plyasunov, A. V.; Shock, E. L. Group contribution values of the infinite dilution thermodynamic functions of hydration for aliphatic noncyclic hydrocarbons, alcohols and ketones at 298.15 K and 0.1 MPa. J. Chem. Eng. Data 2001, 46, 1016-1019.
11. Mills, I.; Cvitaš, T.; Homann, K.; Kallay, N.; Kuchitsu, K. Quantities, Units and Symbols in Physical Chemistry; Blackwell Science: Oxford, U.K., 1993.
12. Sherman, S. R.; Trampe, D. B., Bush, D. M.; Schiller, M.; Eckert, C. A. Compilation and correlation of limiting activity coefficients of nonelectrolytes in water. Ind. Eng. Chem. Res. 1996, 35, 1044-1058.
13. Voutsas, E. C.; Tassios, D. P. Analysis of the UNIFAC-type group-contribution models at the highly diluted region. 1. Limitations of the combinatorial and residual expressions. Ind. Eng. Chem. Res. 1997, 36, 4965-4972.
14. Majer, V.; Svoboda, V.; Pick, J. Heats of vaporization of fluids; Elsevier: Amsterdam, 1989.
15. Frenkel, M.; Marsh, K. N.; Wilhoit, R. C.; Kabo, G. I.; Roganov, G. N. Thermodynamics of Organic Compounds in the Gas State; Thermodynamics Research Center: Texas A&M University System, College Station, TX, 1994; Vols. I and II.
16. Savage, J. J.; Wood, R. H. Enthalpy of dilution of aqueous mixtures of amides, sugars, urea, ethylene glycol, and Pentaerythritol at 25 °C: enthalpy of interaction of the hydrocarbon, amide, and hydroxy functional groups in dilute aqueous solutions. J. Solution Chem. 1976, 5, 733-750.
17. 2, CONH and C-C functional groups in dilute aqueous solutions. J. Chem. Soc., Faraday Trans. I 1978, 74, 1990-2007.
18. Tsonopoulos, C. An empirical correlation of second virial coefficients. AIChE J. 1974, 20, 263-272.
19. Hayden, J. G.; O'Connell, J. P. A generalized method for predicting second virial coefficients. Ind. Eng. Chem. Proc. Des. Dev. 1975, 14, 209-216.
20. Poling, B. E.; Prausnitz, J. M.; O'Connell, J. P. The Properties of Gases and Liquids; McGraw-Hill: New York, 2001.
21. Li, P.; Ma, P.-S.; Yi, S.-Z.; Zhao, Z.-G.; Cong, L.-Z. A new corresponding-states group-contribution method (CSGC) for estimating vapor pressures of pure compounds. Fluid Phase Equilib. 1994, 101, 101-119.
22. Stull, D. R. Vapor pressure of pure substances. Ind. Eng. Chem. 1947, 39, 517-550.
23. Boublik, T.; Fried, V.; Hala, E. The Vapour Pressures of Pure Substances; Elsevier: Amsterdam, 1984.
24. Wittig, R.; Lohmann, J.; Joh, R.; Horstmann, S.; Gmehling, J. Vapor-liquid equilibria and enthalpies of mixing in a temperature range from 298.15 to 413.15 K for the further development of modified UNIFAC (Dortmund). Ind. Eng. Chem. Res. 2001, 40, 5831-5838.
25. Chyliński, K.; Fraś, Z.; Malanowski, S. W. Vapor-Liquid Equilibrium for Phenol + α-Methyl Benzyl Alcohol and 2-Ethoxyethanol + n-Butyl Formate. J. Chem. Eng. Data 2004, 49, 2-6.
26. Majer, V.; Svoboda, V. Enthalpies of Vaporization of Organic Compounds; Blackwell: Oxford, U.K., 1985.
27. Mathews, J. H.; Faville, K. E. The physical properties of a number of pure esters. J. Phys. Chem. 1918, 22, 1-21.
28. Daubert, T. E. Vapor pressure of 13 pure industrial chemicals. DIPPR Data Series 1991, No. 1, 80-95.
29. Riddick, J. A.; Bunger, W. B.; Sakano, T. K Organic Solvents: Physical Properties and Methods of Purification; Wiley: New York, 1986.
30. Schotsch, K.; Wolf, W. A. Vapour pressures of the system tert-butyl acetate/polystyrene. Makromol. Chem. 1984, 185, 2161-2167.
31. Schumann, O. On vapor pressure of homologous esters (in German). Ann. Phys. 1881, 12, 40-65.
32. Anschütz, R.; Reitter, H. Distillation under diminishing pressure in the laboratory (in German); Verlag von Friedrich Cohen: Bonn, Germany, 1895.
33. Steele, W. V.; Chirico, R. D.; Knipmeyer, S. E.; Nguyen, A. Vapor Pressure of Acetophenone, (±)-1,2-Butanediol, (±)-1,3-Butanediol, Diethylene Glycol Monopropyl Ether, 1,3-Dimethyladamantane, 2-Ethoxyethyl Acetate, Ethyl Octyl Sulfide, and Pentyl Acetate. J. Chem. Eng. Data 1996, 41, 1255-1268.
34. Gardner, G. S. Evaporative index. Ind. Eng. Chem. 1940, 32, 226-231.
35. Verevkin, S. P.; Heintz, A. Determination of Vaporization Enthalpies of the Branched Esters from Correlation Gas Chromatography and Transpiration Methods. J. Chem. Eng. Data 1999, 44, 1240-1244.
36. Shigley, J. W.; Bonhorst, C. W.; Liang, C. C.; Althouse, P. M.; Triebold, H. O. Physical characterization of a) a series of ethylesters and b) a series of ethanoate esters. J. Am. Oil Chem. Soc. 1955, 32, 213-215.
37. Meyer, E. F.; Awe, M. J.; Wagner, R. E. Cohesive Energies in Polar Organic Liquids. 4. n-Alkyl Acetates. J. Chem. Eng. Data 1980, 25, 371-374.
38. Koutek, B.; Cvacka, J.; Streinz, L.; Vrkocova, P.; Doubsky, J.; Simonova, H.; Felts, L.; Svoboda, V. Comparison of methods employing gas chromatography retention data to determine vapour pressures at 298 K. J. Chromatogr., A 2001, 923, 137-152.
39. Farkova, J.; Wichterle, I. Vapour pressures of some ethyl and propyl esters of fatty acids. Fluid Phase Equilib. 1993, 90, 143-148.
40. 4). J. Chem. Eng. Data 1999, 44, 772-783.
41. Gonzalez, C.; Ortega, J. Densities and Isobaric Vapor-Liquid Equilibria of Butyl Esters (Methanoate to Butanoate) with Ethanol at 101.32 kPa. J. Chem. Eng. Data 1995, 40, 1178-1183.
42. Berg, L.; Harrison, J. M.; Montgomery, C. W. Azeotropic purification of styrene. Ind. Eng. Chem. 1946, 38, 1149-1152.
43. Stage, H.; Müller, E.; Faldix, P. Separability of volatile components of alcoholic mashes and crude alcohols by distillation. I. Vapor pressures of components (in German). Chem. Technol. 1954, 6, 31-36.
44. Ortega, J.; Galvan S. Vapor-Liquid Equilibria and Densities for Propyl Butanoate + Normal Alcohols at 101.32 kPa. J. Chem. Eng. Data 1995, 40, 699-703.
45. Daubert, T. E. Vapor pressure of 10 pure industrial chemicals. DIPPR Data Series 1994, No. 2, 143-153.
46. Askonas, C. F.; Daubert, T. E. Vapor Pressure Determination of Eight Oxygenated Compounds. J. Chem. Eng. Data 1988, 33, 225-229.
47. Verevkin, S. P.; Beckhaus, H.-D.; Belen'kaja, R. S.; Rakus, K.; Ruchardt, C. Geminal substituent effects. Part 9. Standard enthalpies of formation and strain free increments of branched esters and ethers. Thermochim. Asia 1996, 279, 47-64.
48. Genderen, A. C. G.; van Miltenburg, J. C.; Blok, J. G.; van Bommel, M. J.; van Ekeren, P. J.; van den Berg, G. J. K.; Oonk, H. A. J. Liquid-Vapor Equilibria of the Methyl Esters of Alkanoic Acids: Vapour Pressures as a Function of Temperature and Standard Thermodynamic Function Changes. Fluid Phase Equilib. 2002, 202, 109-120.
49. Ortega, J.; Espiau, F.; Tojo, J.; Canosa, J.; Rodriguez, A. Isobaric Vapor-Liquid Equilibria and Excess Properties for the Binary Systems of Methyl Esters + Heptane. J. Chem. Eng. Data 2003, 48, 1183-1190.
50. Brönsted J. N.; Colman, P. Molecular magnitude and phase distribution. III. (in German). Z. Phys. Chem. Abt. A 1934, 168, 381-390.
51. Hall, H. K.; Baldt, J. H. Thermochemistry of Strained-Ring Bridgehead Nitriles and Esters. J. Am. Chem. Soc. 1971, 93, 140-145.
52. Verevkin, S. P.; Beckhaus, H. D.; Ruechardt, C. Geminal substituent effect. Part 5. Standard enthalpies of formation of alkyl substituted malonic acid and α-aminocarboxylic acid esters (in German). Thermochim. Acta 1992, 197, 27-39.
53. Hancock, C. K.; Watson, G. M.; Gilby, R. F. Heats of Combustion of Five-Carbon Fatty Acids and Their Methyl and Ethyl Esters. J. Phys. Chem. 1954, 58, 127-129.
54. Scott, T. A.; MacMillan, D.; Melvin, E. H. Vapor pressures and distillation of methyl esters of some fatty acids. Ind. Eng. Chem. 1952, 44, 172-175.
55. Buttery, R. G.; Ling, L. C.; Guadagni D. G. Volatilities of Aldehydes, Ketones, and Esters in Dilute Water Solution. J. Agric. Food Chem. 1969, 17, 385-389.
56. 13 Monocyclic Lactones. Strain Energies and Conformations. J. Am. Chem. Soc. 1991, 113, 7697-7705.
57. Suri, S. K.; Wood, R. H. Freezing temperatures of aqueous solutions of methyl formate and ethyl acetate with a variety of nonelectrolytes. Gibbs energy of interaction of the ester group with other functional groups. J. Solution Chem. 1986, 15, 705-715.
58. Segatin, N.; Klofutar, C. Osmotic coefficients of aqueous solutions of some alkyl acetates at the freezing point of the solvent. Monatsh. Chem. 2000, 131, 13-23.
59. Getzen, F.; Hefter, G. Esters with water. Part I. Esters 2-C to 6-C. Solubility Data Series; Pergamon Press: Oxford, U.K., 1992; Vol. 48.
60. Getzen, F.; Hefter, G. Esters with water. Part II. Eaters 7-C to 32-C. Solubility Data Series; Pergamon Press: Oxford, U.K., 1992; Vol. 49.
61. Sorensen, J. M.; Arlt W. Liquid-liquid equilibrium data collection. Binary systems. Chemistry Data Series; DECHEMA: Frankfurt/Main, 1979; Vol. V, Part 1.
62. Suri, S. K.; Spitzer, J. J.; Wood, R. H.; Abel, E. G.; Thompson, P. T. Interactions in aqueous nonelectrolyte systems. Gibbs energy of interaction of the ether group with the hydroxy group and the amide group. J. Solution Chem. 1985, 14, 781-794.
63. Riemenschneider, W. Esters, organic. Ullmann's Encyclopedia of Industrial Chemistry, 7th ed.; Wiley-Interscience, 2003; Online Edition.
64. Stephenson, R.; Stuart, J. Mutual Binary Solubilities: Water-Alcohols and Water-Esters. J. Chem. Eng. Data 1986, 31, 56-70.
65. Nanda, A. K.; Sharma, M. M. Effective interfacial area in liquid-liquid extraction. Chem. Eng. Sci. 1986, 21, 707-714.
66. Nanda, A. K.; Sharma, M. M. M. Kinetics of fast alkaline hydrolysis of esters. Chem. Eng. Sci. 1967, 22, 769-775.
67. Trofimov, A. N. Liquid-liquid equilibrium in isoamyl formate-water and isoamyl formate-formic acid-water systems (in Russian). Gidroliz. Lesokhim. Promst. 1969, 22, 9.
68. Anderson, E. Heats of solution of organic substances. International Critical Tables; McGraw-Hill: New York, 1928; pp 148-160; Vol. 5.
69. Hartkopf, A.; Karger, B. L. Study of the Interfacial Properties of Water by Gas Chromatography. Acc. Chem. Res. 1973, 6, 209-216.
70. Bebahani, G. R.; Dunnion, D.; Falvey, P.; Hickey, K.; Meade, M.; McCarthy, Y.; Symons, M. C. R.; Waghorne, W. E. Nonelectrolyte solvation in aqueous dimethyl sulfoxide - a calorimetric and infrared spectroscopic study. J. Solution Chem. 2000, 29, 521-539.
71. Larina, T. V.; Kern, A. P.; Lebed, V. I. Thermochemistry and physicochemical properties of esters solutions in water-dioxane and water-2-propanol mixtures (in Russian). Zh. Fiz. Khim. 1996, 70, 2171-2176.
72. Aleksandrov, V. V.; Kern, A. P.; Larina, T. V.; Lebed, V. I.; Shikhman, E. L. Thermochemistry of esters in water and aqueous dioxane solutions at 298. 15 K (in Russian). Zh. Fiz. Khim. 1991, 65, 212-214.
73. Huyskens P. L.; Vanderheyden L. Comparison between the transfer enthalpies of esters from cyclohexane towards ethanol and water. Fluid Phase Equilib. 1989, 49, 271-279.
74. Nilsson, S.-O.; Wadso, I. Thermodynamic properties of some mono-, di-, and tri-esters. Enthalpies of solution in water at 288.15 to 318.15 K and enthalpies of vaporization and heat capacities at 298.15 K. J. Chem. Thermodyn. 1986, 18, 673-681.
75. Gatta, D. G.; Stradella, L.; Venturello, P. Enthalpies of solvation in cyclohexane and in water for homologous aliphatic ketones and esters. J. Solution Chem. 1981, 10, 209-220.
76. Cross, R. F.; McTigue, P. T. An analysis of the thermodynamics of transfer of polar nonelectrolytes from water to aqueous concentrated salt solutions. Aust. J. Chem. 1977, 30, 2597-2612.
77. Richon, D., Viallard, A. Water/ester systems. I. Calorimetric study of alkyl acetate/water systems (in French). Can. J. Chem. 1976, 54, 2584-2593.
78. Kustov, A. V.; Antonova, O. A.; Korolev, V. P. Enthalpies of 1,4-dioxane, 1,2-dimethoxyethane, and ethyl acetate solutions in the water-1-propanol and water-glycerol binary mixtures. J. Solution Chem. 2002, 31, 671-680.
79. Kustov, A. V.; Volkova, E. Yu.; Korolev, V. P. Enthalpies of dissolution and specific features of interparticle interactions in the system water - alcohol - ether (in Russian). Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol. 2001, 44, 25-28.
80. Guthrie J. P.; Cullimore P. A. Effect of the acyl substituent on the equilibrium constant for hydration of esters. Can. J. Chem. 1980, 58, 1281-1294.
81. Arnett, E. M.; Burke, J. J.; Carter, J. V.; Douty, C. F. Solvent Effects in Organic Chemistry. XV. Thermodynamics of Solution for Nonelectrolytes in Aqueous Acid and Salt Solutions. J. Am. Chem. Soc. 1972, 94, 7837-7852.
82. Stern, J. H.; O'Connor, M. E. Thermodynamics of Transfer of Esters from Water to Aqueous Dimethyl Sulfoxide at 25 °C. J. Chem. Eng. Data 1972, 17, 185-187.
83. Stern, J. H.; Hermann, A. Solute-Solvent Interactions: Ethyl Acetate in Water. J. Phys. Chem. 1968, 72, 364-365.
84. Stern, J. H.; Hermann, A. Thermodynamics of Aqueous Mixtures of Electrolytes and Nonelectrolytes. 1. Ethyl Acetate and Eight 1-1 Alkali Metal Salts at 25 °C. J. Phys. Chem. 1967, 71, 306-309.
85. Arnett, E. M.; Bentrude, W. G.; Burke, J. J.; Duggleby, McC. P. Solvent Effects in Organic Chemistry. V. Molecules, Ions, and tRansition States in Aqueous Ethanol. J. Am. Chem. Soc. 1965, 87, 1541-1553.
86. Wadsö, I. Heats of hydrolysis of acetates and thioacetates in aqueous solution. Acta Chem. Scand. 1962, 16, 487-494.
87. Segatin N.; Klofutar, C. Thermodynamics of solution of some alkyl acetates in water. Monatsh. Chem. 2001, 32, 1451-1460.
88. Kieckbush, T. G.; King, C. J. An improved method of determining vapor-liquid equilibria for dilute organics in aqueous solution. J. Chromatogr. Sci. 1979, 17, 273-276.
89. Cox, B. G. Free energies, enthalpies, and entropies of transfer of nonelectrolytes from water to mixtures of water and dimethyl sulphoxide, water and acetonitrile, and water and dioxan. J. Chem. Soc., Perkin Trans. II 1973, 607-610.
90. Skrzecz, A. Mutual solubility of water and n-alkyl acetates. Pol. J. Chem. 1980, 54, 1101-1104.
91. Skrzecz, A. Mutual solubility of water and iso-alkyl acetates. Pol. J. Chem. 1981, 55, 1177-1180.
92. Stephenson, R. Mutual Solubilities: Water-Ketones, Water-Ethers, and Water-Gasoline-Alcohols. J. Chem. Eng. Data 1992, 37, 80-95.
93. Larsen, J. W.; Magid, L. J. Enthalpies of binding of organic molecules to cetyltrimethylammonium bromide micelles. J. Phys. Chem. 1974, 78, 834-839.
94. Reid, R. C.; Prausnitz, J. M.; Poling, B. E. The Properties of Gases and Liquids; McGraw-Hill: New York, 1987.
95. Hovorka, S.; Roux, A. H.; Roux-Desgranges, G.; Dohnal, V. Limiting partial molar excess heat capacities and volumes of selected organic compounds in water at 25 °C. J. Solution Chem. 1999, 28, 1289-1305.
96. Costas, M.; Patterson, D. Heat capacities of water + organic-solvent mixtures. J. them. Soc., Faraday Trans. 1 1985, 81, 2381-2398.
97. Roux, G.; Perron, G.; Desnoyers, J. E. The heat capacities and volumes of some low molecular weight amides, ketones, esters, and ethers in water over the whole solubility range. Can. J. Chem. 1978, 56, 2808-2814.
98. Cabani, S.; Conti, G.; Matteoli, E.; Tani, A. Apparent molal heat capacities of organic compounds in aqueous solution. Part 3, ω-amino acids and related compounds. J. Chem. Soc., Faraday Trans. 1 1977, 73, 476-486.
99. Tasker, I. R.; Suri, S. K.; Wood, R. H. Heat Capacities of Some Binary and Ternary Aqueous Nonelectrolyte Systems. J. Chem. Eng. Data 1984, 29, 193-199.
100. Dallas, A. J. Solvatochromic and Thermodynamic Studies of Chromatographic Media. Ph.D. Thesis, University of Minnesota, Minneapolis, MN, 1993 (quoted from ref 101).
101. Trampe, D. B. Limiting Activity Coefficients for Aqueous Solutions. Ph.D. Thesis. University of Illinois at Urbana-Champaign, 1993.
102. Hoff, J. T.; Mackay, D.; Gillham, R.; Shiu, W. Y. Partitioning of Organic Chemicals at the Air-Water Interface in Environmental Systems. Environ. Sci. Technol. 1993, 27, 2174-2180.
103. Kühne, R.; Bocek, K.; Scharfenberg, P.; Frank, R. Hydrophobicity and hydrophobic interactions. II. Differentiation of surface area effects on several thermodynamic transfer data on hydrophobic solutes. Eur. J. Med. Chem. 1981, 16, 7-12.
104. Mash, C. J.; Pemberton, R. C. Activity coefficients at very low concentrations for organic solutes in water determined by an automatic Chromatographic method. NPL Rep. Chem. 1980, 111, pp 1-23.
105. Pecsar, R. E.; Martin, J. J. Solution Thermodynamics from Gas-Liquid Chromatography. Anal. Chem. 1966, 38, 1661-1669.
106. Linek, J.; Wichterle, I.; Marsh, K. N. Vapor-Liquid Equilibria for Water + Diacetone Alcohol, Ethyl Methanoate + Water, and Ethyl Methanoate + Phenol. J. Chem. Eng. Data 1996, 41, 1219-1222.
107. Sorrentino, F.; Voilley, A.; Richon, D. Activity coefficients of aroma compounds in model food systems. AIChE J. 1986, 32, 1988-1993.
108. Richon, D.; Sorrentino, F.; Voilley, A. Infinite dilution activity coefficients by inert gas stripping method: extension to the study of viscous and foaming mixtures. Ind. Eng, Chem. Process Des. Dev. 1985, 24, 1160-1165.
109. Bidner, M. S.; Santiago, D. M. Solubility of nonelectrolyte liquids in an aqueous electrolyte solution (in French). Chem. Eng. Sci. 1971, 26, 1484-1488.
110. Kakovsky, I. A. Physicochemical Properties of Some Flotation Reagents and Their Salts with Ions of Heavy Nonferrous Metals. Proceedings of the Second International Congress of Surface Activity, London, 1957; pp 225-237.
111. Traube, J. Capillary phenomena in relation to constitution and molecular weight (in German). Ber. 1884, 17, 2294-2316.
112. Kaneko, T.; Wang, P.-Y.; Sato, A. Partition coefficients of some acetate esters and alcohols in water, blood, olive oil, and rat tissues. Occup. Environ. Med. 1994, 51, 68-72.
113. Djerki, R. A.; Laub, R. J. Solute retention in column liquid chromatography. X. Determination of solute infinite-dilution activity coefficients in methanol, water, and their mixtures, by combined gas-liquid and liquid-liquid chromatography. J. Liq. Chromatogr. 1988, 11, 585-612.
114. Ioffe, B. V.; Kostkina, M. I.; Vitenberg, A. G. Preparation of Standard Vapor-Gas Mixtures for Gas Chromatography: Discontinuous Gas Extraction. Anal. Chem. 1984, 56, 2500-2503.
115. E for Water/Methyl Acetate at 50 °C. J. Chem. Eng. Data 1983, 28, 405-407.
116. Melder, L. I.; Ebber, A. V. Activity coefficients of esters in hexadecane and water (in Russian). Tr. Tallin. Politechn. Inst. 1978, 449, 3-11.
117. Butler, J. A. V.; Ramchandani, C. N. The solubility of nonelectrolytes. Part II. The influence of the polar group on the free energy of hydration of aliphatic compounds. J. Chem. Soc. 1935, 952-955.
118. McKeown, A.; Stowell, F. P. The vapour pressures of mixtures of (a) methyl acetate and water; (b) methyl acetate, sucrose, and water. J. Chem. Soc. 1927, 97-103.
119. Philippe, E.; Seuvre, A.-M.; Colas, B.; Langendorf, V.; Schippa, C.; Voilley, A. Behavior of Flavor Compounds in Model Food Systems: A Thermodynamic Study. J. Agric. Food Chem. 2003, 51, 1393-1398.
120. Ruth, S. M. v.; Vries, G. d.; Geary, M.; Giannouli, P. Influence of composition and structure of oil-in-water emulsions on retention of aroma compounds. J. Sci. Food Agric. 2002, 82, 1028-1035.
121. Hong, G.-B.; Lee, M.-J.; Lin, H.-m. Multiphase coexistence for mixtures containing water, 2-propanol, and ethyl acetate. Fluid Phase Equilib. 2002, 203, 227-245.
122. Ruth, S. M. v.; Grossmann, I.; Geary, M.; Delahunty, C. M. Interactions between Artificial Saliva and 20 Aroma Compounds in Water and Oil Model Systems. J. Agric. Food Chem. 2001, 49, 2409-2413.
123. Nahon, D. F.; Harrison, M.; Roozen, J. P. Modeling Flavor Release from Aqueous Sucrose Solutions, Using Mass Transfer and Partition Coefficients. J. Agric. Food Chem. 2000, 48, 1278-1284.
124. Segatin, N.; Klofutar, C. Salting-out of some alkyl acetates in aqueous sodium chloride solutions. Monatsh. Chem. 2000, 131, 131-144.
125. Dewulf, J.; Langenhove, H. V.; Everaert, P. Determination of Henry's law coefficients by combination of the equilibrium partitioning in closed systems and solid-phase microextraction techniques. J. Chromatogr., A 1999, 830, 353-363.
126. Al-Sahhaf, T. A.; Kapetanovic, E.; Kadhem, Q. Salt effect on liquid-liquid equilibria in the partially miscible systems water + 2-butanone and water + ethyl acetate. Fluid Phase Equilib. 1999, 157, 271-283.
127. Druaux, C.; Thanh, M. L.; Seuvre, A.-M.; Voilley, A. Application of headspace analysis to the study of aroma compounds - lipid interactions. J. Am. Oil Chem. Soc. 1998, 75, 127-130.
128. Welke, B.; Ettlinger, K.; Riederer, M. Sorption of Volatile Chemicals in Plant Surfaces. Environ. Sci. Technol. 1998, 32, 1099-1104.
129. Harvey, B. A.; Druaux, C.; Voilley, A. Effect of Protein on the Retention and Transfer of Aroma Compounds at the Lipid-Water Interface. In Food Macromolecules and Colloids; Dickinson, E., Lorient, D., Eds.; The Royal Society of Chemistry: Cambridge, England, 1995; pp 154-163.
130. Landy, P.; Druaux, C.; Voilley, A. Retention of aroma compounds by proteins in aqueous solution. Food Chem. 1995, 54, 387-392.
131. Senol, A.; Sayar, A. Liquid-liquid equilibria of some water + tetrahydrofurfuryl alcohol + solvent ternaries at 293.2 ° 0.1 K and 101.3 ° 0.8 kPa. Fluid Phase Equilib. 1995, 106, 169-183.
132. Thanh, M. L.; Lamer, T.; Voilley, A.; Jose, J. Determination of vapor-liquid partition coefficients, activity coefficients of aromatic compounds and their physicochemical characteristics (in French). J. Chim. Phys. 1993, 90, 545-560.
133. Thanh, M. L.; Thibeaudeau, P.; Thibaut, M. A.; Voilley, A. Interactions between volatile and nonvolatile compounds in the presence of water. Food Chem. 1992, 43, 129-135.
134. Pividal, K. A.; Birtigh, A.; Sandler S. I. Infinite Dilution Activity Coefficients for Oxygenate Systems Determined Using a Differential Static Cell. J. Chem. Eng. Data 1992, 37, 484-487.
135. Kolb, B.; Welter, C.; Bichler, C. Determination of partition coefficients by automatic equilibrium headspace gas chromatography by vapor phase calibration. Chromatographia 1992, 34, 235-240.
136. Ratkovics, F.; Palagyi-Fenyes, B.; Hajos-Szikszay, E.; Dallos, A. (Liquid + liquid) equilibria of (ethanoic acid + an alcohol or a ketone or an ester or an aromatic hydrocarbon + water) at the temperature 293.15 K. J. Chem. Thermodyn. 1991, 23, 859-865.
137. Guitart, R.; Puigdemont, A.; Arboix, M, Rapid headspace gas Chromatographic method for the determination of liquid/gas partition coefficients. J. Chromatogr. 1989, 491, 271-280.
138. Jones, W. J.; Egoville, M. J.; Strolle, E. O.; Dellamonica, E. S. Determination of partition coefficients by headspace gas chromatography. J. Chromatogr. 1988, 485, 45-51.
139. Staroske, J.; Schuberth, H. VLE data of the binary systems furfural - ethyl acetate, furfural - water and ethyl acetate -water at 25 °C (in German). Wiss. Z. Univ. Halle. Math.-Naturwiss. Reiche 1988, 37, 85-88.
140. Voilley, A.; Bosset, J. O. New method for rapid determination of the volatility of flavor components in high viscosity media (in French). Lebensm.-Wiss. U. - Technol. 1986, 19, 47-52.
141. Janini, G. M.; Qaddora, L. A. Determination of activity coefficients of oxygenated hydrocarbons by liquid-liquid chromatography. J. Liq. Chromatogr. 1986, 9, 39-53.
142. Bocek, K. Relationships among activity coefficients, partition coefficients and solubilities. Experientia, Suppl. 1976, 23, 231-240.
143. Shaffer, D. L.; Daubert, T. E. Gas-Liquid Chromatographic Determination of Solution Properties of Oxygenated Compounds in Water. Anal. Chem. 1969, 41, 1585-1589.
144. Nelson, P. E.; Hoff, J. E. Food volatiles: gas Chromatographic determination of partition coefficients in water-lipid systems. J. Food Sci. 1968, 33, 479-482.
145. Hong, G.-B.; Lee, M.-J.; Lin, H.-m. Multiphase coexistence for mixtures containing water, 2-propanol, and isopropyl acetate. Ind. Eng. Chem. Res. 2003, 42, 987-944.
146. Gandhi, N. N.; Kumar, M. D.; Sathyamurthy, N. Effect of Hydrotropes on Solubility and Mass-Transfer Coefficient of Butyl Acetate. J. Chem. Eng. Data 1998, 43, 695-699.
147. Sharma, S.; Pandya, G.; Chakrabarti, T.; Khanna, P. Liquid-Liquid Equilibria for 2,3-Butanediol + Water + Organic Solvents at 303.15 K. J. Chem. Eng. Data 1994, 39, 823-826.
148. Weller, R.; Schuberth, H.; Leibnitz, E. Vapor-liquid-phase equilibria of the system phenol - n-butyl acetate - water at 44.4° (in German). J. Prakt. Chem. 1963, 21, 234-249.
149. Solimo, H. N.; Arreguez, N. G. B. d. Liquid-Liquid Equilibria for Water + Ethanol + 2-Methylpropyl Ethanoate and Water + Ethanol + 1,2-Dibromoethane at 298.15 K. J. Chem. Eng. Data 1994, 39, 8-11.
150. Meynier, A.; Garillon, A.; Lethuaut, L.; Genot, C. Partition of five aroma compounds between air and skim milk, anhydrous milk fat or full-fat cream. Lait 2003, 83, 223-235.
151. Lee, M.-J.; Tsai, L.-H.; Hong, G.-B.; Lin, H. Multiphase coexistence for aqueous systems with amyl alcohol and amyl acetate. Ind. Eng. Chem. Res. 2002, 41, 3247-3252.
152. Jouenne, E.; Crouzet, J. Effect of pH on Retention of Aroma Compounds by β-Lactoglobulin. J. Agric. Food Chem. 2000, 48, 1273-1277.
153. Karl, T.; Yeretzian, C.; Jordan, A.; Lindinger, W. Dynamic measurements of partition coefficients using proton-transfer-reaction mass spectrometry (PTR-MS). Int. J. Mass Spectrom. 2003, 223-224, 383-395.
154. Filippov, N. A.; Zayata, V. I.; Miloserdov, P. N.; Serafimov, L. A. Solubility and phase equilibrium in the systems methanol -water - methyl esters of aliphatic acids (in Russian). Neftepererab. Neftekhim. (Moscow) 1972, 7, 37-38.
155. Landy, P.; Courthaudon, J.-L.; Dubois, C.; Voilley, A. Effect of Interface in Model Food Emulsions on the Volatility of Aroma Compounds. J. Agric. Food Chem. 1996, 44, 526-530.
156. Fühner, H. Aqueous solubility in homologous series (in German). Chem. Ber. 1924, 57, 510-515.
157. Bomshtein, A. L.; Trofimov, A. N.; Serafimov, L. A. Liquid-liquid equilibrium in the systems separating agent - water and separating agent - water - acetic acid. J. Appl. Chem. USSR 1978, 51, 1227-1229.
158. Doolittle, A. K. Lacquer solvents in commercial use. Ind. Eng. Chem. 1935, 27, 1169-1179.
159. Amoore, J. E.; Buttery, R. G. Partition coefficients and comparative oflactometry. Chem. Senses Flavour 1978, 3, 57-71.
160. Kato, S.; Matsuda, M.; Nagahama, K. Solubility of fatty acid methyl esters in water. Solvent Extr. 1992, 7A, 141-146.
161. Pustyl'nik, T. M.; Remizov, G. P.; Perelygin, V. M. Mutual solubility of water and ethyl esters of aliphatic acids (in Russian). Izv. Vyssh. Uchebn. Zaved., Pishch. Tekhnol. 1978, 54-56.
162. Chang, Y.-C.; Moulton, R. W. Quaternary liquid systems with two immiscible liquid pairs. Ind. Eng. Chem. 1953, 45, 2350-2361.
163. Pollien, P.; Jordan, A.; Lindinger, W.; Yeretzian, C. Liquid-air partitioning of volatile compounds in coffee: dynamic measurements using proton-transfer-reaction mass spectrometry. Int. J. Mass Spectrom. 2003, 228, 69-80.
164. Roberts, D. D.; Pollien, P. Analysis of Aroma Release during Microwave Heating. J. Agric. Food Chem. 1997, 45, 4388-4392.
165. Lebosse, R.; Ducruet, V.; Feigenbaum, A. Aqueous solubility determination of volatile organic compounds by capillary gas chromatography. J. High Resolut. Chromatogr. 1998, 19, 413-416.
166. Mohammadzadeh-K., A.; Feeney, R. E.; Smith, L. M. Hydrophobic binding of hydrocarbons by proteins. I. Relations of hydrocarbon structure. Biochim. Biophys. Acta 1969, 194, 246-255.
167. Sobotka, H.; Kahn, J. Determination of Solubility of Sparingly Soluble Liquids in Water. J. Am. Chem. Soc. 1931, 53, 2935-2938.
168. Chubarov, G. A.; Danov, S. M.; Logutov, V. I.; Obmelyukhina, T. N. Liquid-liquid equilibrium in ternary systems formed during extraction of acrylic acid from aqueous solutions by aliphatic carboxylic acids of their methyl esters. J. Appl. Chem. USSR 1984, 57, 1671-1673.
169. Tewari, Y. B.; Miller, M. M.; Wasik, S. P.; Martire, D. E. Aqueous Solubility and Octanol/Water Partition Coefficient of Organic Compounds at 25,0 °C. J. Chem. Eng. Data 1982, 27, 451-454.
170. Tasker, I. R.; Spitzer, J. J.; Suri, S. K.; Wood, R. H. Volumetric Properties of Some Aqueous Nonelectrolyte Solutions. J. Chem. Eng. Data 1983, 28, 266-275.
171. Edward, J. T.; Farrell, G.; Shahidi, F. Partial Molar Volumes of Organic Compounds in Water. Part 1. Ethers, Ketones, Esters, and Alcohols. J. Chem. Soc., Faraday Trans. 1 1973, 77, 705-714.
172. Segatin, N.; Klofutar, C. Apparent molar volumes and expansibilities of some alkyl acetates in aqueous solution. Acta Chim. Slov. 1997, 44, 303-316.
173. Sakurai, M.; Nakamura, K.; Nitta, K. Partial Molar Volumes of Alkyl Acetates in Water. J. Chem. Eng. Data 1996, 41, 1171-1175.
174. Plyasunova, N. V.; Plyasunov, A. V.; Shock, E. L. Database of thermodynamic properties for aqueous organic compounds. Int. J. Thermophys. 2004, 25, 351-360.
175. Pierotti, R. A. A Scaled Particle Theory of Aqueous and Non-aqueous Solutions. Chem. Rev. 1976, 76, 717-726.
176. Criss, C. M.; Wood, R. H. Apparent molar volumes of aqueous solutions of some organic solutes at the pressure 28 MPa and temperatures to 598 K. J. Chem. Thermodyn. 1996, 28, 723-741.
177. Wagner, W.; Pruss, A. The IAPWS formulation for the thermodynamic properties of ordinary water substances for general and scientific use. J. Phys. Chem. Ref. Data 2002, 31, 387-535.