Distribution of N-Methylimidazole in Ionic Liquids/Organic Solvents Systems

Abstract

The partition coefficients, Kmim, of N-methylimidazole (mim) in two-component systems composed of ionic liquid (IL) and a series of organic solvents immiscible with ILs (butyl acetate, ethyl acetate, tert-butyl methyl ether, diethyl ether and cyclohexane) were determined by a shake-flask method. The influence of different factors such as temperature, solvent polarity, mim concentration, and water content on Kmim by using 1-butyl-3-methylimidazolium chloride {[C4C1im]Cl} as a model compound was comprehensively studied. The calculated thermodynamic functions of transfer (∆trG0, ∆trH0, ∆trS0) showed that the mim migration (IL→organic phase) is a thermodynamically unfavorable and enthalpy-determined process in the temperature range of 298.15 to 328.15K; however, the results suggested that mim partition toward the organic phase can be enhanced by the rational manipulation of the extraction conditions. Experiments conducted with other 1-alkyl-3-methylimidazolim chlorides (CnC1im]Cl (n = 6, 8, 10) revealed that mim possesses similar behavior and can be successfully washed out from the ILs by extraction with organic solvents. The results obtained in this study give some clues toward the choice of an appropriate solvent and conditions to be employed for the purification of halide-based ILs by means of a liquid-liquid extraction.