Prediction of vapor-liquid equilibria of alcohol+hydrocarbon systems by 1H NMR spectroscopy

Chemical Engineering Science

Volumn 74, Issue , 2012, Pages 211-218

  Xu, Yingjie ^a   Qian, Wu ^a   Gao, Qiongqiong ^a   Li, Haoran ^b  

^a SHAOXING UNIVERSITY   (China)

^b ZHEJIANG UNIVERSITY   (China)

Author keywords

Local composition; Microstructure; NMR; Phase equilibria; Solutions; Thermodynamics

Indexed keywords

ALCOHOL+HYDROCARBON SYSTEM; CONCENTRATION RANGES; CONCENTRATION-DEPENDENT; ENERGY PARAMETERS; H NMR SPECTROSCOPY; ISOBARIC VAPOR-LIQUID EQUILIBRIUM; LOCAL COMPOSITIONS; NMR CHEMICAL SHIFTS; SPECTROSCOPIC INFORMATION; VAPOR-LIQUID EQUILIBRIUM; VLE DATA;

CHEMICAL SHIFT; MICROSTRUCTURE; NUCLEAR MAGNETIC RESONANCE; PHASE EQUILIBRIA; SOLUTIONS; THERMODYNAMICS; VAPORS;

HYDROCARBONS;

EID: 84858729201     PISSN: 00092509     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ces.2012.03.003     Document Type: Article

References (97)

1. Abrams D.S., Prausnitz J.M. Statistical thermodynamic of liquid mixture: a new expression for the excess Gibbs energy of partly or complete miscible systems. AIChE J. 1975, 21:116-128.
2. Ahlers J., Gmehling J. Development of a universal group contribution equation of state. 2. Prediction of vapor-liquid equilibria for asymmetric systems. Ind. Eng. Chem. Res. 2002, 41:3489-3498.
3. Allen B.B., Lingo S.P., Felsing W.A. Total and partial pressures of binary solutions of the butyl alcohols in benzene at 25°C. J. Phys. Chem. 1939, 43:425-430.
4. Asprion N., Hasse H., Maurer G. FT-IR spectroscopic investigations of hydrogen bonding in alcohol-hydrocarbon solutions. Fluid Phase Equilib. 2001, 186:1-25.
5. Asprion N., Hasse H., Maurer G. Application of IR-spectroscopy in thermodynamic investigations of associating solutions. Fluid Phase Equilib. 2003, 205:195-214.
6. Asprion N., Hasse H., Maurer G. Thermodynamic and IR spectroscopic studies of slutions with simultaneous association and solvation. Fluid Phase Equilib. 2003, 208:23-51.
7. 1H NMR spectroscopic and thermodynamic studies of hydrogen bonding in liquid n-butanol+cyclohexane, tert-butanol+cyclohexane, and n-butanol+pyridine mixtures. Phys. Chem. Chem. Phys. 2002, 4:5827-5832.
8. Brown I., Smith F. Liquid-vapor equilibriums. IX. The systems propanol+benzene and butanol+benzene at 45°C. Aust. J. Chem. 1959, 12:407-412.
9. Brown I., Fock W., Smith F. The thermodynamic properties of solutions of normal and branched alcohols in benzene and n-hexane. J. Chem. Thermodyn. 1969, 1:273-291.
10. Brzostowski W., Warycha S. Thermodynamics of cyclohexane-propanol mixtures (ii) vapor pressures and activity coefficients. Bull. Acad. Pol. Sci. Ser. Sci. Chim. 1963, 11:539-544.
11. Cabezas J.L., Arranz J.C., Berrueta J. Binary vapor-liquid equilibria of benzene-alcohol systems. Rev. Roum. Chim. 1985, 30:903-908.
12. Chen G.H., Wang Q., Ma Z.M., Yan X.H., Han S.J. Phase equilibria at superatmospheric pressures for systems containing halohydrocarbon, aromatic hydrocarbon, and alcohol. J. Chem. Eng. Data 1995, 40:361-366.
13. Choi K., Tedder D.W. Molecular interactions in tri-n-butyl phosphate-diluent mixtures. Ind. Eng. Chem. Res. 1996, 35:2048-2059.
14. Choi K., Tedder D.W. Molecular interaction in chloroform-diluent mixtures. AIChE J. 1997, 43:196-211.
15. Coto B., Pando.C., Rubio R.G., Renuncio A.R. Vapour-liquid equilibrium of the ethanol-propanol system. J. Chem. Soc. Faraday Trans. 1995, 91:273-278.
16. D'Agostino C., Mantle M.D., Gladden L.F., Moggridge G.D. Prediction of binary diffusion coefficients in non-ideal mixtures from NMR data: hexane-nitrobenzene near its consolute point. Chem. Eng. Sci. 2011, 66:3898-3906.
17. Dealfonso C., Canovas A.A., Lianas B., Pintado M., Delatorre A.F.S. Isobaric vapor-liquid equilibrium. 5. Thermodynamic study of binary-systems-ethanol+cyclohexane (i), cyclohexane+toluene (ii), carbon-tetrachloride+n-heptane (iii) and carbon-tetrachloride+isooctane (iv). An. Quim. Ser. A 1986, 82:320-330.
18. 1H NMR chemical shift of mixtures. Chem. Phys. Lett. 2003, 276:125-129.
19. Ding T., Huber T., Middelberg A.P.J., Falconer R.J. Characterization of low-frequency modes in aqueous peptides using far-infrared spectroscopy and molecular dynamics simulation. J. Phys. Chem. A 2011, 115:11559-11565.
20. 1H NMR data and mixing enthalpy for systems with complex formation by hydrogen bonding. J. Phys. Chem. B 2002, 106:12307-12310.
21. Dominguez M., Mainar A.M., Artigas H., Royo F.M., Urieta J.S. Isobaric VLE data of the ternary system (1-butanol+n-hexane+1-butylamine) and the three constituent binary mixture at 101.3kPa. J. Chem. Eng. Jpn. 1997, 30:484-490.
22. Eblinger F., Schneider H.J. Self-association of water and water-solute association in chloroform studied by NMR shift titrations. J. Phys. Chem. 1996, 100:5533-5537.
23. Eckert C.A., Newman B.A., Nicolaides G.L., Long T.C. Measurement and application of limiting activity-coefficients. AIChE J. 1981, 27:33-40.
24. Eckert C.A., McNiel M.M., Scott B.A., Halas L.A. NMR measurements of chemical theory equilibrium constants for hydrogen bonded solutions. AIChE J. 1986, 32:820-828.
25. Fan D.F., Li J.L., Shi J.B., Peng C.J., Liu H.L., Hu Y., Paricaud P. Vapor-liquid equilibria in the propyl acetate+ethanoic acid binary system from (323.15 to 353.15)K: measurement with a static method and modeling with the NRTL, Wilson, UNIQUAC, and COSMO-SAC approaches. J. Chem. Eng. Data 2011, 56:1323-1329.
26. Fu H., Mo X.K., Han S.J., Li H.R., Deng F.J. Study on isothermal vapor-liquid equilibria for ethanol-benzene, chloroform-benzene and ethanol-chloroform binary systems. Acta Petrol. Sin. 1995, 11:87-92. (China).
27. Ghosh P., Taraphdar T. Prediction of vapor-liquid equilibria of binary systems using PRSV equation of state and Wong-Sandler mixing rules. Chem. Eng. J. 1998, 70:15-24.
28. Gmehling J.G., Onken U. Vapour-liquid equilibrium data collection. DECHEMA Chemistry Data Series 1977, vol. 1. DECHEMA Frankfurt, Germany.
29. Gmehling J., Li J.D., Schiller M. A modified UNIFAC model. 2. Present parameter matrix and results for different thermodynamic properties. Ind. Eng. Chem. Res. 1993, 32:178-193.
30. Govindaswamy S., Andiappan A., Lakshmanan S. Vapor-liquid equilibrium data at atmospheric-pressure for ternary and sub-binary systems containing n-hexane-benzene-1-butanol. J. Chem. Eng. Data 1976, 21:366-369.
31. Góral M., Skrzecz A., Bok A., Maczyńsk A. Recommended vapor-liquid equilibrium data. Part 3. Binary alkanol-aromatic hydrocarbon systems. J. Phys. Chem. Ref. Data 2004, 33:959-997.
32. Gracia M., Sánchez F., Pérez P., Valero J., Gutierréz L.C. Vapour pressures of (butanol-1-ol+hexane) at temperature between 283.10K and 323.12K. J. Chem. Thermodyn. 1992, 24:463-471.
33. Gupta R.B., Brinkley R.L. Hydrogen-bond cooperativity in 1-alkanol+n-alkane binary mixtures. AIChE J. 1998, 44:207-213.
34. Gupta V., Maken S., Kalra K.C., Sinch K.C. Molar excess Gibbs free energy of 1-propanol or 2-propanol+aromatic hydrocarbons at 298.15K in terms of an association model with a Flory contribution term. Thermochim. Acta 1996, 277:187-198.
35. Haghtalab A., Mahmoodi P. Vapor-liquid equilibria of asymmetrical systems using UNIFAC-NRF group contribution activity coefficient model. Fluid Phase Equilib. 2010, 289:61-71.
36. Hiaki T., Tochigi K., Kojima K. Measurement of vapor-liquid equilibria and determination of azeotropic point. Fluid Phase Equilib. 1986, 26:83-102.
37. Holderbaum T., Gmehling J. PSRK-a group contribution equation of state based on UNIFAC. Fluid Phase Equilib. 1991, 70:251-265.
38. Hwang S.C., Robinson R.L. Vapor-Liquid equilibriums at 25°C for nine alcohol-hydrocarbon binary systems. J. Chem. Eng. Data 1977, 22:319-325.
39. Johnston K.P., Meredith J.C., Harrison K.L. Spectroscopy: the fourth vertex on the molecular thermodynamics tetrahedron. Fluid Phase Equilib. 1996, 116:385-394.
40. Karachewski A.M., McNiel M.M., Eckert C.A. A study of hydrogen bonding in alcohol solutions using NMR spectroscopy. Ind. Eng. Chem. Res. 1989, 28:315-324.
41. Karachewski A.M., Howell W.J., Eckert C.A. Development of the AVEC model for associating mixtures using NMR spectroscopy. AIChE J. 1991, 37:65-73.
42. 1H NMR spectroscopy on a neat organosiloxan-esolvent mixture. Phys. Chem. Phys. Chem. 2011, 13:10661-10669.
43. Kurihara K., Uchiyama M., Kojima K. Isothermal vapor-liquid equilibria for benzene+cyclohexane+1-propanol and for three constituent binary systems. J. Chem. Eng. Data 1997, 42:149-154.
44. Lee S.C. Partial pressure isotherms II. J. Phys. Chem. 1931, 35:3558-3582.
45. Liu H.L., Hu Y. Equation of state for systems containing chainlike molecules. Ind. Eng. Chem. Res. 1998, 37:3058-3066.
46. Luo C., Weber J.H., Tao L.C. Vapor-liquid equilibria of (methanol+methylcyclopentane). J. Chem. Thermodyn. 1985, 17:1097-1101.
47. Loblen G.M., Prausnitz J.M. Infinite-dilution activity-coefficients from differential ebulliometry. I&EC Fundam. 1982, 21:109-113.
48. Ma L., Li H.R., Wang C.M., Xu Y.J., Han S.J. Prediction of vapor-liquid equilibria data from C-H band shifts of Raman spectra and activity coefficients at infinite dilution in some aqueous. Ind. Eng. Chem. Res. 2005, 44:6883-6887.
49. Maciel M.R.W., Francesconi A.Z. Excess Gibbs free energies of (n-hexane+propanol-1-ol) at 338.15 and 348.15K and of (n-hexane+propan-2-ol) at 313.15, 338.15 and 348.15K. J. Chem. Thermodyn. 1988, 20:539-544.
50. Maciel M.R.W., Francesconi A.Z. Vapor-liquid equilibrium measurements for the n-hexane-1-butanol system at 323.15, 338.15 and 348.15K. Fluid Phase Equilib. 1989, 50:201-208.
51. Mann R.S., Shemilt L.W., Waldichuk M. Vapor-liquid equilibria at atmospheric pressure. ii. 1-butanol-benzene system. J. Chem. Eng. Data 1963, 8:502-504.
52. Maripuri V.O., Ratcliff G.A. Measurement of isothermal vapor-liquid equilibriums for acetone-n-heptane mixtures using modified Gillespie still. J. Chem. Eng. Data 1972, 17:366-369.
53. Maurer G., Prausnitz J.M. Derivation and extension of UNIQUAC equation. Fluid Phase Equilib. 1978, 2:91-99.
54. Miyano Y., Hayduk W. Solubilities of butane, vapor pressures, and densities for benzene+cyclohexane, benzene+methanol, and methanol+cyclohexane solutions at 298K. J. Chem. Eng. Data 1993, 38:277-281.
55. Mizuno K., Mabuchi K., Miyagawa T., Matsuda Y., Kita S., Kaida M., Shindo Y. IR study of hydrogen bonds in halogenoalcohol-water mixtures. J. Phys. Chem. A 1997, 101:1366-1369.
56. Nicolaides G.L., Eckert C.A. Optimal representation of binary-liquid mixture non-idealities. I&EC Fundam. 1978, 17:331-340.
57. Ocon J., Tojo G., Bao M., Arce A. Liquid-vapor equilibrium.14. Normal cyclohexane-propanol and cyclohexane-isopropanol binary-systems at 760mm Hg. An. Quim. 1973, 69:1169-1176.
58. Ohta T., Koyabu J., Nagata I. Vapor-liquid equilibriums for ternary ethanol-2-butanone-benzene systems at 298.15K. Fluid Phase Equilib. 1981, 7:65-73.
59. Oracz P., Kolasinska G. Vapour-liquid equilibria-III. Total vapor pressure measurements for binary mixtures of methanol, ethanol, 1-propanol and 1-butanol with benzene, toluene and p-xylene at 313.15K. Fluid Phase Equilib. 1987, 35:253-278.
60. Orye R.V., Prausnitz J.M. Multicomponent equilibria-the Wilson equation. Ind. Eng. Chem. 1965, 57:18-26.
61. Ovejero G., Romero M.D., Díez E., Lopes T., Díaz I. Isobaric vapor-liquid equilibrium for the binary systems 1-pentanol+cyclohexane and 1-pentanol+n-hexane at low alcohol compositions. J. Chem. Eng. Data 2007, 52:1984-1987.
62. Prabhu P.S., Van Winkle M. Effect of polar components on the relative volatility of the binary system n-hexane-benzene. J. Chem. Eng. Data 1963, 8:210-214.
63. Rath P., Suryanarayana A., Nailc S.C. Salt effect in vapor-liquid equilibria at atmospheric pressure. J. Inst. Eng. 1983, 64:6-8. (India).
64. Renon H., Prausnitz J.M. Local compositions in thermodynamic excess functions for liquid mixtures. AIChE J. 1968, 14:135-144.
65. Rhodes J.M., Griffin T.A., Lazzaroni M.J., Bhethanabotla V.R., Campbell S.W. Total pressure measurements for benzene with 1-propanol, 2-propanol, 1-pentanol, 3-pentanol, and 2-methyl-2-butanol at 313.15K. Fluid Phase Equilib. 2001, 179:217-229.
66. Richardson M.J., Johnston J.H., Northcote P.T. NMR determination of high temperature acetic acid/water vapor phase equilibria. AIChE J. 2006, 52:422-424.
67. Ronc M., Ratcliff G.R. Measurement of vapor-liquid equilibria using a semi-continuous total pressure static equilibrium still. Can. J. Chem. Eng. 1976, 54:326-332.
68. Schmelzer J., Alekseeva M.V. Vapor-liquid and liquid-liquid equilibria in systems of hexane, perfluorhexane, 1-propanol.1. Binary-systems. Chem. Technol. 1982, 34:424-426.
69. Schreibe L.B., Eckert C.A. Use of infinite dilution activity coefficients with Wilsons equation. I&EC Proc. Des. Dev. 1971, 10:572-576.
70. Shekaari H., Modarress H., Hadipour N. Thermodynamic investigation on self-association of alcohol in carbon tetrachloride by FT-NMR spectroscopy. J. Phys. Chem. A 2003, 107:1891-1895.
71. Smirnova N.A., Kurtynina L.M. Experimental study of thermodynamic function of mixing for a series of binary alcohol-hydrocarbon solution. Zh. Fiz. Khim. 1969, 43:1883-1885.
72. Strubl K., Svoboda V., Holub R., Pick J. Liquid-vapor equilibrium in benzene-normal-propanol system.71. Collect. Czech. Chem. Commun. 1975, 40:1647-1656.
73. Svoboda V., Holub R., Pick J. Liquid-vapour equilibrium. XLVII. The system cyclohexane-1-hexanol. Collect. Czech. Chem. Commun. 1971, 36:2331-2338.
74. Tamir A., Apelblat A., Wagner M. A new device for measuring isothermal vapor-liquid equilibriums. Fluid Phase Equilib. 1981, 6:237-259.
75. 1H NMR spectroscopy. Can. J. Chem. 1995, 73:1406-1411.
76. 1H NMR and thermodynamic study of self-association and complex formation equilibria by hydrogen bonding. Methanol with chloroform or halothane. Phys. Chem. Chem. Phys. 1999, 1:1479-1486.
77. Toghiani H., Toghiani R.K., Viswanath D.S. Vapor-liquid equilibria for the methanol-benzene and methanol-thiophene systems. J. Chem. Eng. Data 1994, 39:63-67.
78. Tojo B., Bao M., Arce A. Liquid-vapor equilibrium.15. Normal benzene-propanol and benzene-isopropanol binary-systems at 760mm Hg. An. Quim. 1973, 69:1177-1185.
79. Vijayaraghavan S.V., Deshpande P.K., Kuloor N.R. Vapour liquid equilibrium data for benzene-n-butyl alcohol system. Indian J. Technol. 1965, 3:267.
80. E models: results with the Peng-Robinson EoS and a UNIFAC model. Fluid Phase Equilib. 2006, 241:216-228.
81. Wang Q., Chen G.H., Han S.J. Study on the vapor-liquid equilibria under pressure for binary systems. J. Fuel Chem. Technol. 1990, 18:185-192. (China).
82. Wang S.Y., Zhao C.P. VLE data for benzene-n-propanol-lithium chloride system. Chem. Eng. 1991, 19:72-76. (China).
83. ∞. Ind. Eng. Chem. Res. 1987, 26:1372-1381.
84. Wieczorek S.A., Stecki J. Vapour pressures and thermodynamic properties of hexan-1-ol+n-hexane between 198.230 and 342.824K. J. Chem. Thermodyn. 1978, 10:177-186.
85. Wilson G.M. Vapor-liquid equilibrium. XI. A new expression for the excess free energy of mixing. J. Am. Chem. Soc. 1964, 86:127-130.
86. Xu, Y.J., 2005. Studying Solution Thermodynamic Properties of Associating Systems by 1H NMR Chemical Shift. Dissertation, Zhejiang University, Hangzhou, PR China.
87. 1H NMR and activity coefficients at infinite dilution. Chem. Eng. Sci. 2005, 60:3621-3627.
88. 1H NMR and activity coefficients at infinite dilution. Ind. Eng. Chem. Res. 2005, 44:408-415.
89. 1H NMR and azeotropic point. Chin. J. Chem. Eng. 2010, 18:455-461.
90. Xu Z., Li H.R., Wang C.M., Wu T., Han S.J. Is the blue shift of C-H vibration in DMF-water mixture mainly caused by C-H...O interaction?. Chem. Phys. Lett. 2004, 394:405-409.
91. Yerazunis S., Plowright J.D., Smola F.M. Vapor-liquid equilibrium determination by a new apparatus. AIChE J. 1964, 10:660-665.
92. Yuan K.S., Ho J.C.K., Keshpande A.K., Lu B.C.-Y. Vapor-liquid equilibria. J. Chem. Eng. Data 1963, 8:549-559.
93. Zhang R., Li H.R., Lei Y., Han S.J. Different weak C-H...O contacts in N-methylacetamide-water system: molecular dynamics simulations and NMR experimental study. J. Phys. Chem. B 2004, 108:12596-12601.
94. Zhu X., Yao J., Li H.R., Han S.J. Prediction among different spectroscopic properties for aqueous systems. J. Phys. Chem. 2006, 124(244501):1-5.
95. Zhu X., Yao J., Li H.R., Han S.J. Prediction of vapor-liquid equilibrium data from C-H band shift of IR spectra in some binary systems. Chin. J. Chem. Eng. 2007, 15:97-101.
96. Zieikiwicz J., Oracz P., Warycha S. Total vapor pressure measurements and excess Gibbs energies for the binary systems methanol+ethanol, ethanol+2-propanol, benzene+cyclohexane, benzene+carbon tetrachloride and benzene+ethanol at 303.15 and 313.15K. Fluid Phase Equilib. 1990, 58:191-209.
97. Zielkewicz J. (Vapour+liquid) equilibria in (propanol-1-ol+n-hexane+n-heptane) at the temperature 313.15K. J. Chem. Thermodyn. 1991, 23:605-612.