The homogeneous cycloaddition reaction of CO2 and epichlorohydrin catalyzed by amine-functionalized ionic liquid (AFIL) to yield cyclic carbonate is reported in this study. The AFIL has the dual function of ionic liquid and organic base. The experimental study indicates that AFIL can efficiently catalyze the conversion of CO2 and epichlorohydrin to the product 3-chloro-1,2-propylene. The mechanistic study based on DFT calculations reveals that the imidazolium ring in AFIL primarily catalyzes the ring-opening reaction of epichlorohydrin, while the protonated amine group is responsible for stabilizing the Br− anion in the nucleophilic attack. This study provides a deep insight into the catalytic roles of AFIL and also inspires us to design efficient dual function catalysts for CO2 utilization.
The one‐pot reactions of CO2, epibromohydrin, and phenols, thiophenols, or carboxylic acids catalyzed by 1‐butyl‐3‐[(3‐hydroxyphenyl)methyl]imidazolium bromide were investigated. Three kinds of cyclic carbonates with ether, thioether, or ester groups were synthesized under mild reaction conditions in good‐to‐high yields. Reaction‐mechanism studies indicated that the proton exchange between the alkoxide formed through the ring‐opening reaction of epibromohydrin with 1‐bromo‐3‐phenoxy‐2‐propanol plays a crucial role in this synthetic route. The catalyst 1‐butyl‐3‐[(3‐hydroxyphenyl)methyl]imidazolium bromide was transformed to the corresponding cyclic‐carbonate‐functionalized ionic liquid during the reaction. This transformation did not affect its catalytic performance in the reaction.
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