Group contribution values for the thermodynamic functions of hydration at 298.15 K, 0.1 MPa. 4. Aliphatic nitriles and dinitriles

Journal of Chemical and Engineering Data

Volumn 51, Issue 5, 2006, Pages 1481-1490

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

^a ARIZONA STATE UNIVERSITY   (United States)

^b CrystalTech Web Hosting Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DIPOLE-DIPOLE INTERACTIONS; PARTIAL MOLAR GIBBS ENERGY; PARTIAL MOLAR VOLUMES;

ENTHALPY; GIBBS FREE ENERGY; HYDRATION; REACTION KINETICS; SPECIFIC HEAT; THERMODYNAMIC PROPERTIES;

NITRILE RESINS;

EID: 33749819632     PISSN: 00219568     EISSN: None     Source Type: Journal    
DOI: 10.1021/je060129+     Document Type: Review

References (98)

1. Pollak, P.; Romeder, G.; Hagedorn, F. Nitriles. In Ullmann's Encyclopedia of Industrial Chemistry, 7th ed.; Wiley-Interscience: New York, 2005; online edition.
2. Plyasunov, A. V.; Plyasunova, N. V.; Shock, E. L. Group contribution values for the thermodynamic functions of hydration of aliphatic esters at 298.15 K, 0.1 MPa. J. Chem. Eng. Data 2004, 49, 1152-1167.
3. Mills, I.; Cvitaš, T.; Homann, K.; Kallay, N.; Kuchitsu, K. Quantities, Units and Symbols in Physical Chemistry; Blackwell Science: Oxford, 1993.
4. Tsonopoulos, C. An empirical correlation of second virial coefficients. AIChE J. 1974, 20, 263-272.
5. Poling, B. E.; Prausnitz, J. M.; O'Connell, J. P. The Properties of Gases and Liquids; McGraw-Hill: New York, 2001.
6. 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.
7. Majer, V.; Svoboda, V.; Pick, J. Heats of Vaporization of Fluids; Elsevier: Amsterdam, 1989.
8. Plyasunova, N. V.; Plyasunov, A. V.; Shock, E. L. Database of thermodynamic properties for aqueous organic compounds. Int. J. Thermophys. 2004, 25, 351-360.
9. Ewing, M. B.; Ochoa, J. C. S. Vapor pressure of acetonitrile determined by comparative ebulliometry. J. Chem. Eng. Data 2004, 49, 486-491.
10. Antosik, M.; Galka, M.; Malanowski, S. K. Vapor-liquid equilibrium for acetonitrile + propanenitrile and 1-pentanamine + 1-methoxy-2-propanol. J. Chem. Eng. Data 2004, 49, 11-17.
11. Owens, J. L.; Brady, C. J.; Freeman, J. R.; Wilding, W. V.; Wilson, G. M. Vapor-liquid equilibrium measurements. AIChE Symp. Ser. 1987, No. 256, 18-41.
12. Dojcansky, J.; Heinrich, J. Saturated vapour pressure of acetonitrile. Chem. Zvesti 1974, 28, 157-159.
13. Putnam, W. E.; MvEachern, D. M., Jr.; Kilpatrick, J. E. Entropy and related thermodynamic properties of acetonitrile (methyl cyanide). J. Chem. Phys. 1965, 42, 749-755.
14. Heim, G. Vapor tensions and latent heat of vaporization of some normal nitriles. Bull. Soc. Chim. Belg. 1933, 42, 467-482 (in French).
15. Hall, H. K.; Baldt, J. H. Thermochemistry of strained-ring bridgehead nitriles and esters. J. Am. Chem. Soc. 1971, 93, 140-145.
16. Dreisbach, R. R.; Shrader, S. A. Vapor pressure-temperature data on some organic compounds. Ind. Eng. Chem. 1949, 41, 2879-2880.
17. Garriga, R.; Sanchez, F.; Perez, P.; Gracia, M. Vapour pressures at several temperatures T and excess functions at T = 298.15 K of (butanenitrile + propan-1-ol or propan-2-ol). J. Chem. Thermodyn. 1995, 27, 887-895.
18. Meyer, E. F.; Hotz, R. D. High-precision vapor-pressure data for eight organic compounds. J. Chem. Eng. Data 1973, 18, 359-362.
19. Meyer, E. F.; Renner, T. A.; Stec, K. S. Cohesive energies in polar organic liquids. II. The n-alkyl nitriles and the 1-chloroalkanes. J. Phys. Chem. 1971, 75, 642-648.
20. Majer, V.; Svoboda, V. Enthalpies of Vaporization of Organic Compounds; Blackwell: Oxford, 1985.
21. Emel'yanenko, V. N.; Verevkin, S. P.; Koutek, B.; Doubsky, J. Vapour pressures and enthalpies of vapourization of a series of the linear aliphatic nitriles. J. Chem. Thermodyn. 2005, 37, 73-81.
22. Kruif, C. G. de; Miltenburg, J. C. v.; Blok, J. G. Molar heat capacities and vapour pressures of solid and liquid benzophenone. J. Chem. Thermodyn. 1983, 15, 129-136.
23. Ruzicka, K.; Majer, V. Simple and controlled extrapolation of vapor pressures toward the triple point. AIChE J. 1996, 42, 1723-1740.
24. Verevkin, S. P. Improved Benson increments for the estimation of standard enthalpies of vaporization of alkyl ethers, acetals, ketals, and ortho esters. J. Chem. Eng. Data 2002, 47, 1071-1097.
25. Stein, S. E.; Brown, R. L. Structures and properties group additivity model. NIST Chemistry WebBook; MIST Standard Reference Database Number 69; Linstrom, P. J., Mallard, W. G., Eds.; National Institute of Standards and Technology: Gaithersburg, MD, 2005 (http://webbok.nist.gov).
26. 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.
27. Ruzicka, V.; Domalski, E. S. Estimation of the heat capacities of organic liquids as a function of temperature using group additivity. I. Hydrocarbon compounds. J. Phys. Chem. Ref. Data 1993, 22, 597-618.
28. Ruzicka, V.; Domalski, E. S. Estimation of the heat capacities of organic liquids as a function of temperature using group additivity. II. Compounds of carbon, hydrogen, halogens, nitrogen, oxygen, and sulfur. J. Phys. Chem. Ref. Data 1993, 22, 619-657.
29. Woodman, A. L.; Murbach, W. J.; Kaufman, M. H. Vapor pressure and viscosity relationships for a homologous series of α,ω-dinitriles. J. Phys. Chem. 1960, 64, 658-660.
30. Deizenrot, I. V.; Kogan, V. B.; Fridman, V. M. Isolation of pure hexamethylenediamine. Khim. Prom. 1965, 178-180 (in Russian).
31. Wulff, C. A.; Westrum, E. F. Heat capacities and thermodynamic properties of globular molecules. VI. Succinonitrile. J. Phys. Chem. 1963, 67, 2376-2381.
32. Budavari, S.; O'Neil, M. J.; Smith, A.; Heckelman, P. E. The Merck Index. An Encyclopedia of Chemicals, Drugs, and Biologicals, 11th ed.; Merck & Co.: Rahway, NJ, 1989.
33. Smiley, R. A.; Arnold, C. Aliphatic nitriles from alkyl chlorides. J. Org. Chem. 1960, 25, 257-258.
34. Boyd, R. H.; Guha, K. R.; Wuthrich, R. Thermochemistry of cyanocarbons. II. The heats of combustion of pyridinium dicyanomethylide, malononitrile, and fumaronitrile. J. Phys. Chem. 1967, 71, 2187-2191.
35. Beckhaus, H.-D.; Dogan, B.; Pakusch, J.; Verevkin, S.; Ruchardt, C. Geminal substituent effects. 4. The dependence of the inverse anomeric effect of geminal cyano groups on the structure. Chem. Ber. 1990, 123, 2153-2159 (in German).
36. Dove, M. T.; Farelly, G.; Rae, A. I. M.; Wright, L. The re-entrant phase transitions in malononitrile: specific heat capacity measurements. J. Phys. C: Solid State Phys. 1983, 16, L195-L198.
37. Wasiutynski, T.; Olejarczyk, W.; Sciesinski, J.; Witko, W. Phase transition studies of malononitrile. J. Phys. C: Solid State Phys. 1987, 20, L65-L69.
38. 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.
39. 2, CONH and C=C functional groups in dilute aqueous solutions. J. Chem. Soc., Faraday Trans. 11978, 74, 1990-2007.
40. Kustov, A. V.; Bekeneva, A. V.; Antonova, O. A.; Korolev, V. P. Enthalpic pair-interaction coefficients of benzene, aniline and nitrobenzene with N,N-dimethylformamide and acetonitrile in water at 298.15 K. Thermochim. Acta 2003, 398, 9-14.
41. Hovorka, S.; Donnai, 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 Eauilib. 2002, 201, 135-164.
42. 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.
43. Kulikov, M. V.; Antonova, O. A.; Slyusar, V. P.; Korolev, V. P. Enthalpies of solution of propylene carbonate, acetonitrile, and 1,4-dioxane in mixtures of water with acetone and dimethyl sulfoxide. Izv. Akad. Nauk, Ser. Khim. 1995, 1747-1752 (in Russian).
44. Donnal, V.; Roux, A. H.; Hynek, V. Limiting partial molar excess enthalpies by flow calorimetry: some organic solvents in water. J. Solution Chem. 1994, 23, 889-900.
45. Batov, D. V.; Egorova, N. G.; Svishchev, A. F.; Korolev, V. P. Enthalpies of dissolution of acetonitrile, dimethyl sulfoxide, and propylene carbonate in water-methanol, water-2-propanol, and water-tert-butanol mixtures. Russ. J. Gen. Chem. 1994, 64, 1561 - 1564.
46. Trampe, D. M.; Eckert, C. A. Calorimetric measurement of partial molar excess enthalpies at infinite dilution. J. Chem. Eng. Data 1991, 36, 112-118.
47. Stokes, R. H. Excess partial molar enthalpies for (acetonitrile + water) from 278 to 318 K. J. Chem. Thermodyn. 1987, 19, 977-983.
48. Korolev, V. P.; Batov, D. V.; Krestov, G. A. The isotope effect in the enthalpies of hydration of liquid non-electrolytes. Kuss. J. Phys. Chem. 1985, 59, 123-124.
49. 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.
50. Larsen, J. W.: Magid, L. J. Enthalpies of binding of organic molecules to cetyltrimethylammonium bromide micelles. J. Phys. Chem. 1974, 78, 834-839.
51. Stephenson, R. M. Mutual solubility of water and nitriles. J. Chem. Eng. Data 1994, 39, 225-227.
52. Schreinemakers, F. A. H. Equilibria in the system: water, sodium chloride and succinonitrile. Z. Phys. Chem. 1897, 23, 417-441 (in German).
53. Ashtari, K.; Alizadeh, N. Liquid-liquid equilibria in binary mixtures of water with malonitrile, succinonitrile, and glutaronitrile. J. Chem. Eng. Data 2001, 49, 1494-1498.
54. Serwy, H. The freezing temperature of organic compounds. Bull. Soc. Chim. Belg. 1933, 42, 483-501 (in French).
55. Zilberman, E. N. The water-adiponitrile-ammonia system. J. Appl. Chem. USSR 1953, 26, 867-873.
56. Frenkel, M.; Marsh, K. N.; Wilhoit, R. C.; Kabo, G. I.; Roganov, G. N. Thermodynamics of Organic Compounds in the Gas State, Vols. I and II; Thermodynamics Research Center, Texas A&M University System: College Station, TX, 1994.
57. Hovorka, S.; Roux, A. H.; Roux-Desgranges, G.; Donnai, 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.
58. Benson, G. C.; D'Arcy, P. J.; Handa, Y. P. Thermodynamics of aqueous mixtures of nonelectrolytes. V. Isobaric heat capacities and ultrasonic speeds for water + ethanenitrile mixtures at 25°C. Thermochim. Acta 1981, 46, 295-301.
59. Visser C. D.; Heuvelsland, W. J. M.; Dunn, L. A.; Somsen, G. Some properties of binary aqueous liquid mixtures. Apparent molar volumes and heat capacities at 298.15 K over the whole mole fraction range. J. Chem. Soc. Faraday Trans. 1 1978, 74, 1159-1169.
60. Lisi, R. D.; Milioto, S.; Triolo, R. Volumes, heat capacities and solubilities of amyl compounds in decyltrimethylammonium bromide aqueous solutions. J. Solution Chem. 1989, 18, 905-925.
61. Sorensen, J. M.; Arlt, W. Liquid-Liquid Equilibrium Data Collection. Binary Systems. Chemistry Data Series, Vol. V, Part 1; DECHEMA: Frankfurt/Main, 1979.
62. Abbott, S. M.; Elder, J. B.; Spanel, P.; Smith, D. Quantification of acetonitrile in exhaled breath and urinary headspace using selected ion flow tube mass spectrometry. Int. J. Mass Spectrom. 2003, 228, 655-665.
63. Bebahani, G. R. R.; Hogan, P.; Waghorne, W. E. Ostwald concentration coefficients of acetonitrile in aqueous mixed solvents: a new, rapid method for measuring the solubilities of volatile solutes. J. Chem. Eng. Data 2002, 47, 1290-1292.
64. Nikolova, P. V.; Duff, S. J. B.; Westh, P.; Haynes, C. A.; Kasahara, Y.; Nishikawa, K.; Koga, Y. A Thermodynamic study of aqueous acetonitrile: excess chemical potentials, partial molar enthalpies, entropies and volumes, and fluctuations. Can. J. Chem. 2000, 78, 1553-1560.
65. Welke, B.; Ettlinger, K.; Riederer, M. Sorption of volatile chemicals in plant surfaces. Environ. Sci. Technol. 1998, 32, 1099-1104.
66. Park, S.-J.; Oh, J. H.; Choi, H. J.; Paek, S. K.; Fisher, K.; Gmehling, J. Phase equilibria and the excess molar volume for the systems acrylonitrile + water, acetonitrile + water, and acrylonitrile + acetonitrile. Hwahak Konghak 1997, 35, 678-683 (in Korean).
67. Benkelberg, H.-J.; Hamm, S.; Warneck, P. Henry's law coefficients for aqueous solutions of acetone, acetaldehyde and acetonitrile, and equilibrium constants for the addition compounds of acetone and acetaldehyde with bisulfite. J. Atmos. Chem. 1995, 20, 17-34.
68. Li, J.; Carr, P. W. Measurement of water-hexadecane partition coefficients by headspace gas chromatography and calculation of limiting activity coefficients in water. Anal. Chem. 1993, 05, 1443-1450.
69. Dallas, A. J. Solvatochromic and thermodynamic studies of Chromatographic media. Ph.D. Thesis, University of Minnesota, Minneapolis, MN, 1993.
70. French, H. T. Vapour pressure and activity coefficients of (acetonitrile + water) at 308.15 K. J. Chem. Thermodyn. 1987, 19, 1155-1161.
71. Snider, J. R.; Dawson, G. A. Tropospheric light alcohols, carbonyls, and acetonitrile: concentrations in the Southwestern United States and Henry's law data. J. Geophys. Res. 1985, 90, 3797-3805.
72. E for ethylene glycol/acetone/water and for ethylene glycol/acetonitrile/ water at 50°C. J. Chem. Eng. Data 1984, 29, 293-296.
73. Hamm, S.; Hahn, J.; Helas, G.; Warneck, P. Acetonitrile in the troposphere: residence time due to rainout and uptake by the ocean. Geophys. Res. Lett. 1984, 11, 1207-1210.
74. Wilson, S. R.; Patel, R. B.; Abbott, M. M.; Ness, H. C. V. Excess thermodynamic functions for ternary systems. 4. Total-pressure data and GE for acetonitrile-ethanol-water at 50°C. J. Chem. Eng. Data 1979, 24, 130-132.
75. Sugi, H.; Katayama, T. Ternary liquid-liquid and miscible binary vapor-liquid equilibrium data for the two systems n-hexanes-ethanol-acetonitrile and water-acetonitrile-ethyl acetate. J. Chem. Eng. Jpn. 1978, 11, 167-172.
76. Cox, B. G.; Parker, A. J.; Waghorne, W. E. Liquid junction potentials between electrolyte solution in different solvents. J. Am. Chem. Soc. 1973, 95, 1010-1014.
77. Grande, M. d. C.; Marschoff, C. M. Liquid-liquid equilibria of water + benzonitrile + acetonitrile or + propionitrile. J. Chem. Eng. Data 2000, 45, 686-688.
78. Taramasso, M.; Malde, M. D. Vapor-liquid equilibria in binary systems: acrylonitrile-propionitrile-acetonitrile-water. Chim. Ind. (Milan, Italy) 1967, 49, 820-825 (in Italian).
79. Prokhorova, V. V.; Serafimov, L. A.; Novoselova, R. I.; Takhtamysheva, L. S. Solubility in the systems acrylonitrile-propionitrile-water and acrylonitrile-acetonitrile-water. Russ. J. Phys. Chem. 1964, 38, 809-811.
80. Booth, H. S.; Everson, H. E. Hydrotropic solubilities. Solubilities in 40 percent sodium xylenesulfonate. Ind. Eng. Chem. 1948, 40, 1491 1493.
81. 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.
82. Ramachandran, B. R.; Allen, J. M.; Halpern, A. M. Air-water partitioning of environmentally important organic compounds. An environmental chemistry or integrated laboratory experiment. J. Chem. Educ. 1996, 73, 1058-1061.
83. Mellan, I. Industrial Solvents Handbook', Noyes Data Corporation: Park Ridge, NJ, 1977 (quoted from the Materials of Union Carbide Corporation).
84. Kakovsky, I. A. Physicochemical properties of some flotation reagents and their salts with ions of heavy non-ferrous metals. Proceedings of the Second International Congress of Surface Activity, London, 1957; pp 225-237.
85. Sayar, A. A. Liquid-liquid equilibria of some water + 2-propanol + solvent ternaries. J. Chem. Eng. Data 1991, 36, 61-65.
86. Letcher, T. M.; Naicker, P. N. Liquid-liquid equilibria for mixtures + an alkanol + a nitrile compound at T = 298.15 K. J. Chem. Eng. Data 2001, 46, 1436-1441.
87. Zil'berman, E. N.; Fedoseeva, G. T. Separation of adiponitrile from adipic acid and ammonia reaction products. Khim. Prom. 1958, 377-379 (in Russian).
88. Meurs, N. v.; Somsen, G. Excess and apparent molar volumes of mixtures of water and acetonitrile between 0 and 25°C. J. Solution Chem. 1993, 22, 427-436.
89. Sakurai, M. Partial molar volumes for acetonitrile + water. J. Chem. Eng. Data 1992, 37, 358-362.
90. 6 n-alkanenitriles and octanenitrile in dilute aqueous solutions at 298.16 K. J. Chem. Eng. Data 1984, 29, 266-269.
91. 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.
92. 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.
93. Benson, S. W. Thermochemical Kinetics; John Wiley & Sons: New York, 1976.
94. McMillan, W. G.; Mayer J. E. The statistical thermodynamics of multicomponent systems. J. Chem. Phys. 1945, 13, 276-305.
95. Milioto, S.; De Lisi, R. Enthalpies of mixing of some nitriles aqueous solutions with dodecyl surfactants micellar solutions. J. Solution Chem. 1988, 17, 937-952.
96. Indelli, A.; Pancaldi, G. Molecular interactions of organic substances in aqueous solution: acetamide and acetonitrile. Ann. Chim. (Rome) 1956, 46, 387-395 (in Italian).
97. Funk, C. E. Partial pressure of acrylonitrile over water. Ind. Eng. Chem. 1951, 43, 1152-1154.
98. 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.