Solvent properties of piperidinium ionic liquids

Chemical Engineering Journal

Volumn 172, Issue 2-3, 2011, Pages 1066-1071

  Lee, Jong Min ^a  

^a Nanyang Technological University   (Singapore)

Author keywords

Ionic liquid; Kamlet Taft parameters; Polarity

Indexed keywords

ALKYL CHAIN; DIPOLARITY; EXPERIMENTAL STUDIES; HYDROGEN-BOND BASICITY; KAMLET-TAFT PARAMETERS; POLARITY; SOLVENT PROPERTIES;

FUNCTIONAL GROUPS; HYDROGEN; POSITIVE IONS;

IONIC LIQUIDS;

EID: 84860389537     PISSN: 13858947     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cej.2011.06.030     Document Type: Article

References (36)

1. Baranchugov V., Markevich E., Pollak E., Salitra G., Aurbach D. Amorphous silicon thin films as a high capacity anodes for Li-ion batteries in ionic liquid electrolytes. Electrochem. Commun. 2007, 9:796-800.
2. Bini R., Chiappe C., Mestre V.L., Pomelli C.S., Welton T. A rationalization of the solvent effect on the Diels-Alder reaction in ionic liquids using multiparameter linear solvation energy relationships. Org. Biomol. Chem. 2008, 6:2522-2529.
3. Dzyuba S.V., Bartsch R.A. Expanding the polarity range of ionic liquids. Tetrahedron Lett. 2002, 43:4657-4659.
4. Fuller J., Breda A.C., Carlin R.T. Ionic liquid-polymer gel electrolytes. J. Electrochem. Soc. 1997, 144:L667.
5. Gordon C.M. New developments in catalysis using ionic liquids. Appl. Catal. 2001, 222:101-117.
6. Hinckley G., Mozhaev V.V., Budde C., Khmelnitsky Y.L. Oxidative enzymes possess catalytic activity in systems with ionic liquids. Biotechnol. Lett. 2002, 24:2083-2087.
7. Lee J.-M., Ruckes S., Prausnitz J.M. Solvent polarities and Kamletâ 'Taft parameters for ionic liquids containing a pyridinium cation. J. Phys. Chem. B 2008, 112:1473-1476.
8. Peter W., Wilhelm K. Ionic liquids-new ldquoSolutionsrdquo for transition metal catalysis. Angew. Chem. 2000, 39:3772-3789.
9. Reichardt C. Polarity of ionic liquids determined empirically by means of solvatochromic pyridinium N-phenolate betaine dyes. Green Chem. 2005, 7:339-351.
10. Salminen J., Papaiconomou N., Kumar R.A., Lee J.-M., Kerr K., Newman J., Prausnitz J.M. Physicochemical properties and toxicities of hydrophobic piperidinium and pyrrolidinium ionic liquids. Fluid Phase Equilib. 2007, 261:421-426.
11. Sheng D., Ju Y.H., Barnes C.E. Solvent extraction of strontium nitrate by a crown ether using room-temperature ionic liquids. J. Chem. Soc. Dalton Trans. 1999, 1201-1202.
12. Visser A.E., Swatloski R.P., Griffin S.T., Hartman D.H., Rogers R.D. Liquid/liquid extraction of metal ions in room temperature ionic liquids. Sep. Sci. Technol. 2001, 36:785-804.
13. Yang J.-Z., Wang B., Zhang Q.-G., Tong T. Study on solid-liquid phase equilibria in ionic liquid: 1. The solubility of alkali chloride (MCl) in ionic liquid EMISE. Fluid Phase Equilib. 2007, 251:68-70.
14. Yuan L.X., Feng J.K., Ai X.P., Cao Y.L., Chen S.L., Yang H.X. Improved dischargeability and reversibility of sulfur cathode in a novel ionic liquid electrolyte. Electrochem. Commun. 2006, 8:610-614.
15. Zhang Q.-Z., Yang J.-Z., Lu X.-M., Gui J.-S., Huang M. Studies on an ionic liquid based on FeCl3 and its properties. Fluid Phase Equilib. 2004, 226:207-211.
16. Dupont J., de Souza R.F., Suarez P.A.Z. Ionic liquid (molten salt) phase organometallic catalysis. Chem. Rev. 2002, 102:3667-3692.
17. Luo H., Dai S., Bonnesen P.V. Solvent extraction of Sr2+ and Cs+ based on room-temperature ionic liquids containing monoaza-substituted crown ethers. Anal. Chem. 2004, 76:2773-2779.
18. Papaiconomou N., Lee J.-M., Salminen J., Stosch M.V., Prausnitz J.M. Selective extraction of copper, mercury, silver, and palladium ions from water using hydrophobic ionic liquids. Ind. Eng. Chem. Res. 2007, 47:5080-5086.
19. Tiwari S., Khupse N., Kumar A. Intramolecular Dielsâ Alder reaction in ionic liquids: effect of ion-specific solvent friction. J. Org. Chem. 2008, 73:9075-9083.
20. van Rantwijk F., Sheldon R.A. Biocatalysis in ionic liquids. Chem. Rev. 2007, 107:2757-2785.
21. Wilkes J.S. Properties of ionic liquid solvents for catalysis. J. Mol. Catal. A: Chem. 2004, 214:11-17.
22. Kamlet M.J., Abboud J.L.M., Abraham M.H., Taft R.W. Linear solvation energy relationships. 23. A comprehensive collection of the solvatochromic parameters, pi, alpha, and beta, and some methods for simplifying the generalized solvatochromic equation. J. Org. Chem. 1983, 48:2877-2887.
23. Kamlet M.J., Taft R.W. The solvatochromic comparison method. I. The beta-scale of solvent hydrogen-bond acceptor (HBA) basicities. J. Am. Chem. Soc. 1976, 98:377-383.
24. Kosower E.M. The effect of solvent on spectra. I. A new empirical measure of solvent polarity: z-values. J. Am. Chem. Soc. 1958, 80:3253-3260.
25. Reichardt C. Solvatochromic dyes as solvent polarity indicators. Chem. Rev. 1994, 94:2319-2358.
26. Taft R.W., Kamlet M.J. The solvatochromic comparison method. 2. The alpha-scale of solvent hydrogen-bond donor (HBD) acidities. J. Am. Chem. Soc. 1976, 98:2886-2894.
27. Persson I. Solvation and complex formation in strongly solvating solvents. Pure Appl. Chem. 1986, 58:1153-1161.
28. Reichardt C. Solvent Effects in Organic Chemistry 2003, Wiley-VCH, Weinheim. 3rd ed.
29. Baker S.N., Baker G.A., Bright F.V. Temperature-dependent microscopic solvent properties of 'dry' and 'wet' 1-butyl-3-methylimidazolium hexafluorophosphate: correlation with ET(30) and Kamlet-Taft polarity scales. Green Chem. 2002, 4:165-169.
30. Crowhurst L., Mawdsley P.R., Perez-Arlandis J.-M., Salter P.A., Welton T. Solvent-solute interactions in ionic liquids. Phys. Chem. Chem. Phys. 2003, 5:2790-2794.
31. Khupse N.D., Kumar A. Contrasting thermosolvatochromic trends in pyridinium-, pyrrolidinium-, and phosphonium-based ionic liquids. J. Phys. Chem. B 2009, 114:376-381.
32. Lee J.-M., Prausnitz J.M. Polarity and hydrogen-bond-donor strength for some ionic liquids: effect of alkyl chain length on the pyrrolidinium cation. Chem. Phys. Lett. 2010, 492:55-59.
33. Zhao Q., Eichhorn J., Pitner W., Anderson J. Using the solvation parameter model to characterize functionalized ionic liquids containing the tris(pentafluoroethyl)trifluorophosphate (FAP) anion. Anal. Bioanal. Chem. 2009, 395:225-234.
34. Papaiconomou N., Salminen, Lee J.-M., Prausnitz J.M. Physicochemical properties of hydrophobic ionic liquids containing 1-octylpyridinium, 1-octyl-2-methylpyridinium, or 1-octyl-4-methylpyridinium cations. J. Chem. Eng. Data 2007, 52:833-840.
35. Papaiconomou N., Yakelis N., Salminen J., Bergman R., Prausnitz J.M. Synthesis and properties of seven ionic liquids containing 1-methyl-3-octylimidazolium or 1-butyl-4-methylpyridinium cations. J. Chem. Eng. Data 2006, 51:1389-1393.
36. Zhang Q., Li Z., Zhang J., Zhang S., Zhu L., Yang J., Zhang X., Deng Y. Physicochemical properties of nitrile-functionalized ionic liquids. J. Phys. Chem. B 2007, 111:2864-2872.