Prediction of infinite-dilution activity coefficients of organic solutes in ionic liquids using temperature-dependent quantitative structure-property relationship method

Chemical Engineering Journal

Volumn 163, Issue 3, 2010, Pages 195-201

  Xi, Lili ^a   Sun, Huijun ^a   Li, Jiazhong ^a   Liu, Huanxiang ^b   Yao, Xiaojun ^a   Gramatica, Paola ^c  

^a LANZHOU UNIVERSITY   (China)

^b LANZHOU UNIVERSITY   (China)

^c UNIVERSITY OF INSUBRIA   (Italy)

Author keywords

Genetic algorithm variables subset selection; Infinite dilution activity coefficient; Ionic liquid; Ordinary least square regression; Temperature dependent quantitative structure property relationship

Indexed keywords

DILUTION ACTIVITY COEFFICIENTS; GREEN SOLVENTS; INFINITE-DILUTION ACTIVITY COEFFICIENT; LEAST SQUARE REGRESSION; MOLECULAR DESCRIPTORS; ORGANIC SOLUTES; PREDICTION MODEL; PREDICTIVE ABILITIES; QUANTITATIVE STRUCTURE PROPERTY RELATIONSHIPS; QUANTITATIVE STRUCTURE-PROPERTY RELATIONSHIP MODELS; SUBSET SELECTION; TEMPERATURE DEPENDENT; TEMPERATURE-DEPENDENT QUANTITATIVE STRUCTURE-PROPERTY RELATIONSHIP;

ACTIVITY COEFFICIENTS; DILUTION; FORECASTING; GENETIC ALGORITHMS; IONS; MATHEMATICAL MODELS; REGRESSION ANALYSIS; STRUCTURAL PROPERTIES;

IONIC LIQUIDS;

EID: 77956652517     PISSN: 13858947     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cej.2010.07.023     Document Type: Article

References (40)

1. Welton T. Room-temperature ionic liquids. solvents for synthesis and catalysis. Chem. Rev. 1999, 99:2071-2084.
2. Sheldon R. Catalytic reactions in ionic liquids. Chem. Commun. 2001, 23:2399-2407.
3. Huddleston J.G., Visser A.E., Reichert W.M., Willauer H.D., Broker G.A., Rogers R.D. Characterization and comparison of hydrophilic and hydrophobic room temperature ionic liquids incorporating the imidazolium cation. Green Chem. 2001, 3:156-164.
4. Earle M.J., Seddon K.R. Ionic liquids. Green solvents for the future. Pure Appl. Chem. 2000, 72:1391-1398.
5. Freemantle M. Ionic liquids show promise for clean separation technology. Chem. Eng. News 1998, 76.
6. 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.
7. Park S., Kazlauskas R.J. Biocatalysis in ionic liquids - advantages beyond green technology. Curr. Opin. Biotechnol. 2003, 14:432-437.
8. Jaitely V., Florence A.T. 1-Alkyl-3-methyl-imidazole hexafluoro-phosphate water-immiscible ionic liquids as reservoirs for controlled release of drugs. Abstracts of Papers, 226th ACS National Meeting 2003, 7-11.
9. 2: a case study for deep desulfurization of oil refinery streams by extraction with ionic liquids. Green Chem. 2006, 8:70-77.
10. 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.
11. Letcher T.M., Reddy P. Determination of activity coefficients at infinite dilution of organic solutes in the ionic liquid, trihexyl(tetradecyl)-phosphonium tris(pentafluoroethyl)trifluorophosphate, by gas-liquid chromatography. Fluid Phase Equilibr. 2005, 235:11-17.
12. 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.
13. Warren D., Letcher T.M., Ramjugernath D., Raal J.D. Activity coefficients of hydrocarbon solutes at infinite dilution in the ionic liquid, 1-methyl-3-octyl-imidazolium chloride from gas-liquid chromatography. J. Chem. Thermodyn. 2003, 35:1335-1341.
14. 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-methyl-3-ethyl-imidazolium bis(trifluoromethyl-sulfonyl) amide and in 1,2-dimethyl-3-ethyl-imidazolium bis(trifluoromethyl-sulfonyl) amide using gas-liquid chromatography. J. Chem. Eng. Data 2002, 47:894-899.
15. Marsh K., Deev A., Wu A., Tran E., Klamt A. Room temperature ionic liquids as replacements for conventional solvents - a review. Korean J. Chem. Eng. 2002, 19:357-362.
16. Vasiltsova T.V., Verevkin S.P., Bich E., Heintz A., Lukasik R.B., Domanska U. Thermodynamic properties of mixtures containing ionic liquids. Activity coefficients of ethers and alcohols in 1-methyl-3-ethyl-imidazolium bis(trifluoromethyl-sulfonyl)imide using the transpiration method. J. Chem. Eng. Data 2004, 50:142-148.
17. Kato R., Krummen M., Gmehling J. Measurement and correlation of vapor-liquid equilibria and excess enthalpies of binary systems containing ionic liquids and hydrocarbons. Fluid Phase Equilibr. 2004, 224:47-54.
18. Diedenhofen M., Eckert F., Klamt A. Prediction of infinite dilution activity coefficients of organic compounds in ionic liquids using COSMO-RS. J. Chem. Eng. Data 2003, 48:475-479.
19. Freire M.G., Santos L.M.N.B.F., Marrucho I.M., Coutinho J.A.P. Evaluation of COSMO-RS for the prediction of LLE and VLE of alcohols+ionic liquids. Fluid Phase Equilibr. 2007, 255:167-178.
20. Eike 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.
21. http://www.oecd.org/document/23/0,2340,en_2649_201185_33957015_1_1_1_1,00.html.
22. Gramatica P. Principles of QSAR models validation: internal and external. QSAR Comb. Sci. 2007, 26:694-701.
23. Tropsha A., Gramatica P., Gombar V.K. The importance of being earnest: validation is the absolute essential for successful application and interpretation of QSPR models. QSAR Comb. Sci. 2003, 22:69-77.
24. Revelli A.L., Sprunger L.M., Gibbs J., Acree W.E., Baker G.A., Mutelet F. Activity coefficients at infinite dilution of organic compounds in trihexyl(tetradecyl)phosphonium bis(trifluoromethylsulfonyl)imide using inverse gas chromatography. J. Chem. Eng. Data 2009, 54:977-985.
25. A.R. Katritzky, V.S. Lobanov, M. Karelson, Reference Manual, Semichem and the Comprehensive Descriptors for Structural and Statistical Analysis, Version 2.0 (Workstation) and 2.13 (PC), CODESSA, University of Florida, 1995-1997.
26. Efron B. The Jackknife, the Bootstrap, and Other Resampling Plans 1982, Society for Industrial Mathematics, Philadelphia, PA.
27. Gramatica P., Giani E., Papa E. Statistical external validation and consensus modeling: a QSPR case study for KOC prediction. J. Mol. Graph. Model. 2007, 25:755-766.
28. Letcher T.M., Ramjugernath D., Laskowska M., Królikowski M., Naidoo P., Domańska U. Determination of activity coefficients at infinite dilution of solutes in the ionic liquid, trihexyltetradecylphosphonium bis(trifluoromethylsulfonyl)imide, using gas-liquid chromatography at T=(303.15, 308.15, 313.15, and 318.15)K. J. Chem. Eng. Data 2008, 53:2044-2049.
29. HyperChem 7.0, Hypercube Inc., 2002.
30. Stewart J.P.P. MOPAC 6.0, Quantum Chemistry Program Exchange (QCPE) 1989, Indiana University, Bloomington, IN, Program 455.
31. Li J.Z., Lei B.L., Liu H.X., Li S.Y., Yao X.J., Liu M.C., Gramatica P. QSAR study of malonyl-CoA decarboxylase inhibitors using GA-MLR and a new strategy of consensus modeling. J. Comput. Chem. 2008, 29:2636-2647.
32. Liu H.X., Papa E., Gramatica P. QSAR prediction of estrogen activity for a large set of diverse chemicals under the guidance of OECD principles. Chem. Res. Toxicol. 2006, 19:1540-1548.
33. Xi L.L., Du J., Li S.Y., Li J.Z., Liu H.X., Yao X.J. A combined molecular modeling study on gelatinises and their potent inhibitors. J. Comput. Chem. 2010, 31:24-42.
34. Ghasemi J.B., Abdolmaleki A., Mandoumi N. A quantitative structure property relationship for prediction of solubilization of hazardous compounds using GA-based MLR in CTAB micellar media. J. Hazard. Mater. 2009, 161:74-80.
35. Todeschini R., Consonni V., Pavan M. MOBYDIGS, Version 1.2 for Windows, Software for Multilinear Regression Analysis and Variable Subset Selection by Genetic Algorithm 2002, Talete SRL, Milan, Italy.
36. Lindgren F., Hansen B., Karcher W., Sjöström M., Eriksson L. Model validation by permutation tests: applications to variable selection. J. Chemometr. 1996, 10:521-532.
37. Baumann K. Cross-validation as the objective function for variable-selection techniques, TrAC. Trends Anal. Chem. 2003, 22:395-406.
38. Eriksson L., Jaworska J., Worth A.P., Cronin M.T.D., McDowell R.M., Gramatica P. Methods for reliability and uncertainty assessment and for applicability evaluations of classification- and regression-based QSARs. Environ. Health Perspect. 2003, 111:1361-1375.
39. Gramatica P., Papa E. QSAR modeling of bioconcentration factor by theoretical molecular descriptors. QSAR Comb. Sci. 2003, 22:374-385.
40. George R.F., Carl A.P., Leland Y.W. Using theoretical descriptors in quantitative structure activity relationships: some physicochemical properties. J. Phys. Org. Chem. 1992, 5:395-408.