Herein, an ionic liquid, 1-[1-(ethoxycarbonyl)-2-oxopropyl]-3-methylimidazolium chloride (1,3-(CO)2IL-HCl), was synthesized and used as a donor of hydrogen chloride (HCl) to participate in an organic reaction. Interestingly, the simultaneously generated 1-[1-(ethoxycarbonyl)-2-oxopropyl]-3-methylimidazolium inner salt (1,3-(CO)2IL) can then capture HCl from another reaction that produces HCl as a waste. This allowed us to use IL as a shuttle to transfer waste HCl from the first reaction to the second one that needs HCl as one of the reactants. In a proof-of-concept experiment, a ring-opening reaction of glycidyl phenyl ether with released HCl was selected; and the waste HCl comes from an alcoholysis of benzoyl chloride with ethanol. 1,3-(CO)2IL can be used as a shuttle for transferring HCl five times without evident decline of its performance. Mechanism investigation revealed that the interconversion of keto and enol forms in 1,3-(CO)2IL and a moderate pKa value are keys to ensuring the release and capture of HCl.
You have access to this article
Please wait while we load your content…
Something went wrong. Try again?