Cyclic Carbonates Obtained by Reactions of Alkali Metal Carbonates with Epihalohydrins

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Abstract
A study has been carried out on the reaction of alkali metal carbonates with epihalohydrins in the presence of cation complexing agents e.g. crown ethers. 3-Glycidyloxypropylene carbonate was found to be formed as the main product of the reaction of epichlorohydrin with potassium carbonate promoted by 18-crown-6. The effect of various epihalohydrins and alkali metal carbonates on the reaction course was examined. It was found that the reaction of potassium hydrogencarbonate with epichlorohydrin gives 4-hydroxymethyl-1,3-dioxolan-2-one. When the reaction of epihalohydrins with potassium carbonates was carried out in the atmosphere of carbon dioxide the products contained linear carbonate linkage apart from cyclic one. From these results, a plausible mechanism was proposed for the reaction of alkali metal carbonates with epihalohydrins in the presence of crown ethers.

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