Characterization of room-temperature ionic liquids by the abraham model with cation-specific and anion-specific equation coefficients

Journal of Chemical Information and Modeling

Volumn 47, Issue 3, 2007, Pages 1123-1129

  Sprunger, Laura ^a   Clark, Michael ^a   Acree, William E ^a   Abraham, Michael H ^b  

^a UNIVERSITY OF NORTH TEXAS   (United States)

^b UNIVERSITY COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CORRELATION METHODS; NEGATIVE IONS; POSITIVE IONS;

ABRAHAM MODEL; GAS-TO-RTIL (ROOM-TEMPERATURE IONIC LIQUID) PARTITION COEFFICIENTS; PARTITION COEFFICIENTS;

IONIC LIQUIDS;

EID: 34250865100     PISSN: 15499596     EISSN: 1549960X     Source Type: Journal    
DOI: 10.1021/Ci7000428     Document Type: Article

References (65)

1. Park, S.; Kazlauskas, R. J. Biocatalysis in ionic liquids-advantages beyond green technology. Curr. Opin. Biotechnol. 2003, 14, 432-437.
2. Viswanathan, G.; Murugesan, S.; Pushparaj, V.; Nalamasu, O.; Ajayan, P. M.; Linhardt, R. J. Preparation of Biopolymer Fibers by Electrospinning from Room Temperature Ionic Liquids. Biomacromolecules 2006, 7, 415-418.
3. Murugesan, S.; Linhardt, R. J. Ionic liquids in carbohydrate chemistry - current trends and future directions. Curr. Org. Synth. 2005, 2, 437-451.
4. Jaitely, V.; Florence, A. T. 1-Alkyl-3-methyl-imidazole hexafluorophosphate water-immiscible ionic liquids as reservoirs for controlled release of drugs. Abstracts of Papers, 226th ACS National Meeting, New York, United States, September 7-11, 2003.
5. 2: A case study for deep desulfurization of oil refinery streams by extraction with ionic liquids. Green Chem. 2006, 8, 70-77.
6. Khodadoust, A. P.; Chandrasekaran, S.; Dionysiou, D. D. Preliminary assessment of imidazolium-based room-temperature ionic liquids for extraction of organic contaminants from soils. Environ. Sci. Technol. 2006, 40, 2339-2345.
7. Reetz, M. T.; Wiesenhoefer, W.; Francio, G.; Leitner, W. Biocatalysis in ionic liquids: batchwise and continuous flow processes using supercritical carbon dioxide as the mobile phase. Chem. Commun. 2002, 992-993.
8. Poole, C. F. Chromatographic and spectroscopic methods for the determination of solvent properties of room temperature ionic liquids, J. Chromatogr. A 2004, 1037, 49-82.
9. Chiappe, C.; Pieraccini, D. Ionic liquids: solvent properties and organic reactivity. J. Phys. Org. Chem. 2005, 18, 275-297.
10. Bike, D. M.; Brennecke, J. F.; Maginn, E. J. Predicting infinite-dilution activity coefficients of organic solutes in ionic liquids. Ind. Eng. Chem. Res. 2004, 43, 1039-1048.
11. Tämm, K.; Burk, P. QSPR analysis for infinite dilution activity coefficients of organic compounds. J. Mot. Model. 2006, 12, 417-421.
12. Acree, W. E., Jr.; Abraham, M. H. The analysis of solvation in ionic liquids and organic solvents using the Abraham linear free energy relationship. J. Chem. Technol. Biotechnol. 2006, 81, 1441-1446.
13. [Erratum, 2006, 81, 1722 (2006)].
14. Abraham, M. H.; Acree, W. E.; Jr. Comparative analysis of solvation and selectivity in room temperature ionic liquids using the Abraham linear free energy relationship, Green Chem. 2006, 8, 906-915.
15. Mintz, C.; Acree, W. E., Jr. Partition coefficient correlations for transfer of solutes from the gas phase and from water to room temperature ionic liquids. Phys. Chem. Liq. Manuscript accepted for publication.
16. Abraham, M. H.; Zissimos, A. M.; Huddleston, J. G.; Willauer, H. D.; Rogers, R. D.; Acree, W. E.; Jr. Some novel liquid partitioning systems: water-ionic liquids and aqueous biphasic systems. Ind. Eng. Chem. Res. 2003, 42, 413-418.
17. Sumartschenkowa, I. A.; Verevkin, S. P.; Vasiltsova, T. V.; Bich, E.; Heintz, Andreas;, Shevelyova, M. P.; Kabo, G. J. Experimental study of thermodynamic properties of mixtures containing ionic liquid 1-ethyl-3-methylimidazolium ethyl sulfate using gas-liquid chromatography and transpiration method. J. Chem. Eng. Data 2006, 51, 2138-2144.
18. Shiflett, M. B.; Yokozeki, A. Gaseous absorption of fluoromethane, fluoroethane, and 1,1,2,2-tetrafluoroethane in 1-butyl-3-methylimidazolium hexafluorophosphate. Ind. Eng. Chem. Res. 2006, 45, 6375-6382.
19. Zhou, Q.; Wang, L.-S. Activity coefficients at infinite dilution of alkanes, alkenes, and alkylbenzenes in 1-butyl-3-methylimidazolium tetrafluoroborate using gas-liquid chromatography. J. Chem. Eng. Data 2006, 51, 1698-1701.
20. Foco, G. M.; Bottini, S. B.; Quezada, N.; De la Fuente, J. C.; Peters, C. J. Activity coefficients at infinite dilution in 1-alkyl-3-methylimidazolium tetrafluoroborate ionic liquids. J. Chem. Eng. Data 2006, 51, 1088-1091.
21. Shiflett, M. B.; Yokozeki, A. Solubility and diffusivity of hydrofluorocarbons in room-temperature ionic liquids. AIChE J. 2006, 52, 1205-1219.
22. Safarov, J.; Verevkin, S. P.; Bich, E.; Heintz, A. Vapor pressures and activity coefficients of n-alcohols and benzene in binary mixtures with 1-methyl-3-butylimidazolium octylsulfate and 1-methyl-3-octylimidazolium tetrafluoroborate. J. Chem. Eng. Data 2006, 51, 518-525.
23. Heintz, A.; Verevkin, S. P.; Ondo, D. Thermodynamic properties of mixtures containing ionic liquids. 8. Activity coefficients at infinite dilution of hydrocarbons, alcohols, esters, and aldehydes in 1-hexyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide using gas-liquid chromatography. J. Chem. Eng. Data 2006, 51, 434-437.
24. Heintz, A.; Vasiltsova, T. V.; Safarov, J.; Bich, E.; Verevkin, S. P. Thermodynamic properties of mixtures containing ionic liquids. 9. Activity coefficients at infinite dilution of hydrocarbons, alcohols, esters, and aldehydes in trimethylbutylammonium bis(trifluoromethylsulfonyl)imide using gas-liquid chromatography and static method. J. Chem. Eng. Data 2006, 51, 648-655.
25. Vasiltsova, T. V.; Verevkin, S. P.; Bich, E.; Heintz, A.; Bogel-Lukasik, R.; Domanska, U. Thermodynamic properties of mixtures containing ionic liquids. 7. Activity coefficients of aliphatic and aromatic esters and benzylamine in 1-methyl-3-ethylimidazolium bis(trifluoromethylsulfonyl)imide using the transpiration method. J. Chem. Eng. Data 2006, 51, 213-218.
26. Letcher, T. M.; Marciniak, A.; Marciniak, M.; Domanska, U. Activity coefficients at infinite dilution measurements for organic solutes in the ionic liquid 1-hexyl-3-methyl-imidazolium bis(trifluoromethylsulfonyl)-imide using g.l.c. at T = (298.15, 313.15, and 333.15) K. J. Chem. Thermodyn. 2005, 37, 1327-1331.
27. Heintz, A.; Verevkin, S. P. Thermodynamic properties of mixtures containing ionic liquids. 6. Activity coefficients at infinite dilution of hydrocarbons, alcohols, esters, and aldehydes in 1-methyl-3-octylimidazolium tetrafluoroborate using gas-liquid chromatography. J. Chem. Eng. Data 2005, 50, 1515-1519.
28. Heintz, A.; Casas, L. M.; Nesterov, I. A.; Emel'yanenko, V. N.; Verevkin, S. P. Thermodynamic properties of mixtures containing ionic liquids. 5. Activity coefficients at infinite dilution of hydrocarbons, alcohols, esters, and aldehydes in 1-methyl-3-butylimidazolium bis-(trifluoromethylsulfonyl)imide using gas-liquid chromatography. J. Chem. Eng. Data 2005, 50, 1510-1514.
29. Kato, R.; Gmehling, J. Systems with ionic liquids: Measurement of VLB and data and prediction of their thermodynamic behavior using original UNIFAC, mod. UNIFAC(Do) and COSMO-RS(Ol). J. Chem. Thermodyn. 2005, 37, 603-619.
30. 4] and oxygenated organic compounds respectively water. Fluid Phase Equilib. 2005, 237, 38-43.
31. Vasiltsova, T. V.; Verevkin, S. P.; Bich, E.; Heintz, A.; Bogel-Lukasik, R.; Domanska, U. Thermodynamic properties of mixtures containing ionic liquids. Activity coefficients of ethers and alcohols in 1-methyl-3-ethylimidazolium bis(trifluoromethylsulfonyl)imide using the transpiration method. J. Chem. Eng. Data 2005, 50, 142-148.
32. -. Fluid Phase Equilib. 2004, 226, 37-44.
33. Deenadayalu, N.; Letcher, T. M.; Reddy, P. Determination of activity coefficients at infinite dilution of polar and nonpolar solutes in the ionic liquid 1-ethyl-3-methyl-imidazolium bis(trifluoromethylsulfonyl)-imidate using gas-liquid chromatography at the temperature 303.15 K or 318.15 K. J. Chem. Eng. Data 2005, 50, 105-108.
34. Letcher, T. M.; Soko, B.; R., P.; Deenadayalu, N. Determination of activity coefficients at infinite dilution of solutes in the ionic liquid 1-hexyl-3-methylimidazolium tetrafluoroborate using gas-liquid chromatography at the temperatures 298.15 K and 323.15 K. J. Chem. Eng. Data 2003, 48, 1587-1590.
35. Letcher, T. M.; Soko, B.; Ramjugernath, D.; Deenadayalu, N.; Nevines, A.; Naicker, P. K. Activity coefficients at infinite dilution of organic solutes in 1-hexyl-3-methylimidazolium hexafluorophosphate from gas-liquid chromatography. J. Chem. Eng. Data 2003, 48, 708-711.
36. Krummen, M.; Wasserscheid, P.; Gmehling, J. Measurement of activity coefficients at infinite dilution in ionic liquids using the dilutor technique. J. Chem. Eng. Data 2002, 47, 1411-1417.
37. Heintz, A.; Kulikov, D. V.; Verevkin, S. P. Thermodynamic properties of mixtures containing ionic liquids. Activity coefficients at infinite dilution of polar solutes in 4-methyl-N-butylpyridinium tetrafluoroborate using gas-liquid chromatography. J. Chem. Thermodyn. 2002, 34, 1341-1347.
38. Heintz, A.; Kulikov, D. V.; Verevkin, S. P. Thermodynamic properties of mixtures containing ionic liquids. 2. Activity coefficients at infinite dilution of hydrocarbons and polar solutes in 1-methy 1-3-ethylimidazolium bis(trifluoromethylsulfonyl)amide and in 1,2-dimethyl-3-ethylimidazolium bis(trifluoromethylsulfonyl) amide using gas-liquid chromatography. J. Chem. Eng. Data 2002, 47, 894-899.
39. Heintz, A.; Kulikov, D. V.; Verevkin, S. P. Thermodynamic properties of mixtures containing ionic liquids. 1. Activity coefficients at infinite dilution of alkanes, alkenes, and alkylbenzenes in 4-methyl-N-butylpyridinium tetrafluoroborate using gas-liquid chromatography. J. Chem. Eng. Data 2001, 46, 1526-1529.
40. Camper, D.; Becker, C.; Koval, C.; Noble, R. Diffusion and solubility measurements in room temperature ionic liquids. Ind. Eng. Chem. Res. 2006, 45, 445-450.
41. Camper, D.; Becker, C.; Koval, C.; Noble, R. Low pressure hydrocarbon solubility in room temperature ionic liquids containing imidazolium rings interpreted using regular solution theory. Ind. Eng. Chem. Res. 2005, 44, 1928-1933.
42. 2 solubility in ionic liquids. J. Phys. Chem. B 2006, 110, 15059-15062.
43. 6]. J. Chem. Eng. Data 2006, 51, 1802-1807.
44. Lee, B.-C.; Outcalt, S. L. Solubilities of gases in the ionic liquid 1-n-butyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide. J. Chem. Eng. Data 2006, 51, 892-897.
45. Jacquemin, J.; Costa, Gomes, M. F.; Husson, P.; Majer, V. Solubility of carbon dioxide, ethane, methane, oxygen, nitrogen, hydrogen, argon, and carbon monoxide in 1-butyl-3-methylimidazolium tetrafluoroborate between temperatures 283 K and 343 K and at pressures close to atmospheric. J. Chem. Thermodyn. 2006, 38, 490-502.
46. Jacquemin, J.; Husson, P.; Majer, V.; Gomes, M. F. C. Low-pressure solubilities and thermodynamics of solvation of eight gases in 1-butyl-3-methylimidazolium hexafluorophosphate. Fluid Phase Equilib. 2006, 240, 87-95.
47. Anthony, J. L.; Anderson, J. L.; Maginn, E. J.; Brennecke, J. F. Anion effects on gas solubility in ionic liquids. J. Phys. Chem. B 2005, 109, 6366-6374.
48. Ohlin, C. A.; Dyson, P. J.; Laurenczy, G. Carbon monoxide solubility in ionic liquids: determination, prediction and relevance to hydroformylation. Chem. Commun. 2004, 1070-1071.
49. 2N]. J. Chem. Thermodyn. 2006, 38, 1396-1401.
50. Baltus, R. E.; Culbertson, B. H.; Dai, S.; Luo, H.; DePaoli, D. W. Low-pressure solubility of carbon dioxide in room-temperature ionic liquids measured with a quartz crystal microbalance. J. Phys. Chem. B 2004, 108, 721-727.
51. Zhou, Q.; Wang, L.-S.; Wu, J.-S.; Li, M.-Y. Activity coefficients at infinite dilution of polar solutes in 1-butyl-3-methylimidazolium tetrafluoroborate using gas-liquid chromatography. J. Chem. Eng. Data 2007, 52, 131-134.
52. Letcher, T. M.; Soko, B.; Ramjugernath, D.; Deenadayalu, N.; Nevines, A.; Naicker, P. K. Activity coefficients at infinite dilution of organic solutes in 1-hexyl-3-methylimidazolium hexafluorophosphate from gas-liquid chromatography. J, Chem. Eng. Data 2003, 48, 708-711.
53. Verevkin, S. P.; Vasiltsova, T. V.; Bich, E.; Heintz, A. Thermodynamic properties of mixtures containing ionic liquids Activity coefficients of aldehydes and ketones in 1-methyl-3-ethyl-imidazolium bis- (trifluoromethylsulfonyl)imide using the transpiration method. Fluid Phase Equilib. 2004, 218, 165-175.
54. Abraham, M. H. Scales of hydrogen bonding: Their construction and application to physicochemical and biochemical processes. Chem. Soc. Rev. 1993, 22, 73-83.
55. Abraham, M. H.; Ibrahim, A.; Zissimos, A. M. The determination of sets of solute descriptors from Chromatographic measurements. J. Chromatogr. A 2004, 1037, 29-47.
56. Abraham, M. H.; Acree, W. E., Jr. Correlation and prediction of partition coefficients between the gas phase and water, and the solvents dodecane and undecane. New J. Chem. 2004, 28, 1538-1543.
57. Abraham, M. H.; Acree, W. E., Jr. The correlation and prediction of butane/water and gas/butane partition coefficients. Can. J. Chem. Eng. 2005, 83, 362-365.
58. PharmaAlgorithms Inc. PharmaAlgorithms, ADME Boxes, Version 2.2; PharmaAlgorithms Inc.: Toronto, Ontario, Canada.
59. Abraham, M. H.; Green, C. E.; Acree, W. E., Jr.; Hernandez, C. E.; Roy, L. E. Descriptors for solutes from the solubility of solids: transstilbene as an example. J. Chem. Soc., Perkin Trans. 2 1998, 2677-2682.
60. Green, C. E.; Abraham, M. H.; Acree, W. E., Jr.; De Fina, K. M.; Sharp, T. L. Solvation descriptors for pesticides from the solubility of solids: diuron as an example. Pest Manage. Sci. 2000, 56, 1043-1053.
61. Zissimos, A. M.; Abraham, M. H.; Du, C. M.; Valko, K.; Bevan, C.; Reynolds, D.; Wood, J.; Tam, K. Y. Calculation of Abraham descriptors from experimental data from seven HPLC systems; evaluation of five different methods of calculation. J. Chem. Soc., Perkin Trans. 2 2002, 2001-2010.
62. Zissimos, A. M.; Abraham, M. H.; Barker, M. C.; Box, K. J.; Tam, K. Y. Calculation of Abraham descriptors from solvent-water partition coefficients in four different systems; evaluation of different methods of calculation. J. Chem. Soc., Perkin Trans. 2 2002, 470-477.
63. McGowan, J. C.; Abraham, M. H. The use of characteristic volumes to measure cavity terms in reversed phase liquid chromatography. Chromatographia 1987, 23, 243-246.
64. SPSS, Data Mining, Statistical Analysis Software, Predictive Applications, Predictive Analytics, Decision Support Systems. http://www.spss.com (accessed March 6, 2007).
65. Abraham, M. H.; Zhao, Y. H. Determination of solvation descriptors for ionic species: hydrogen bond acidity and basicity. J. Org. Chem. 2004, 69, 4677-4685.