Carboxylic acid functionalized imidazolium-based ionic liquids: efficient catalysts for cycloaddition of CO2 and epoxides

Abstract

In this study, a series of imidazolium-based ionic liquids (ILs) having carboxylic acid moieties were synthesized and used as new homogeneous catalysts to synthesize cyclic carbonates from CO2 and epoxides. Even in the absence of any co-catalyst and organic solvent, carboxylic-acid-functionalized ILs showed better catalytic activity in the coupling reaction of CO2 and styrene oxide for the production of styrene carbonate than did hydroxyl-functionalized ILs and conventional ILs without any functional moieties. A detailed investigation was carried out on a variety of factors that affected the reactivity, such as the alkyl chain length and the molecular composition of IL molecules including the halide ions. The effect of various reaction parameters such as reaction time, temperature, CO2 pressure and catalyst amount was also investigated in detail. The mechanism underlying the enhanced rate of the cycloaddition reaction in the presence of carboxylic-acid-functionalized ILs was proposed.