Diethyl Carbonate → Ethylene carbonate

Participants

Reaction Steps

U.S. Pat. No. 3,426,042 discloses a process of synthesis of cyclic carbonic esters from glycol and diethyl carbonate using sodium hydroxide as a catalyst. But this literature fails to refer to its yield, not describing in further detail. Further, Journal of American Chemical Society, vol. 68 (1946), p.783 discloses a process in which ethylene carbonate is formed from ethylene glycol and diethyl carbonate using potassium carbonate as a catalyst and from which a cyclic carbonic ester is isolated by crystallization. In this method, however, the yield of the object compound is low (51 to 55%) and such low yield is not sufficient for practical commercial operation. Furthermore, although the isolation by crystallization is effective for ethylene carbonate (melting point: 37 to 39° C.), not all object compounds are covered by this method. In the case where the object product is a cyclic carbonic ester having a low melting point, for example, a 6-membered-ring cyclic carbonic ester (propylene carbonate), the isolation by crystallization is not effective due to the melting point as low as -55° C., and rather difficult. A product having a low melting point can be isolated by distillation, for example, by flash evaporation or thin film evaporation. The distillation of the reaction product according to the above-mentioned method, however, leads to the hydrolysis or reverse reaction of the reaction product and thus results in the decomposition of the object compound. Particularly, the use of an optically active substance as a reactant leads to the loss of its optical activity and racemization thereof.

Provenance & Evidence