Abstract
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.
Highlights
The concentration of carbon dioxide (CO2) in the atmosphere continues to increase due to the deforestation and burning of fossil fuels, which makes earth’s environment worse than before (Hunt et al, 2010; Monastersky, 2013)
To investigate the intramolecular synergistic catalytic system of imidazolium and amino functional group in amine-functionalized ionic liquid (AFIL), benzyl3-butylimidazolium bromide (BnBimBr), DEBA and AFIL were applied to catalyze the cycloaddition of CO2 and epichlorohydrin
We report a new synthesized amine-functional ionic liquid (AFIL) which could catalyze the reaction of CO2 and epichlorohydrin to yield cyclic carbonate
Summary
The concentration of carbon dioxide (CO2) in the atmosphere continues to increase due to the deforestation and burning of fossil fuels, which makes earth’s environment worse than before (Hunt et al, 2010; Monastersky, 2013). The rational conversion of CO2 to valuable chemicals has attracted wide attentions all over the world in decades (Rochelle, 2009; Jones, 2011). One of effective methodologies for CO2 conversion is to use high-energy materials such as epoxides to react with CO2 to yield oxidized low-energy synthetic targets (Sakakura et al, 2007). The epichlorohydrin, as one of significant functional epoxides (Padwa and Murphree, 2005; D′Elia et al, 2015), is the main raw material for the synthesis of epoxy resin and glycerol in chemical industry. It is desirable to perform the cycloaddition of CO2 with epoxides to give rise to the valuable chemicals such as cyclic carbonates
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