Transesterification of dialkyl carbonates with fluorine-containing alcohols

Reactions of transesterification of dimethyl, diethyl and dibutyl carbonates with 2,2,3,3-tetrafluoroethyl-, 2,2,3,3,4,4,5,5-octafluorobutyl- and 2,2,3,3,4,4,5,5,6,6,7,7-dodecafluorohexyl-carbinols were investigated in the presence of various catalysts. It was found that the conversion of starting dialkyl carbonate increases upon increasing the length of fluorine-containing radical in the presence of sodium alkoxide. It was shown that the maximum conversion of dimethyl carbonate (90%) was achieved in its reaction with 2,2,3,3,4,4,5,5-octafluoropentan-1-ol upon using catalysts such as K2CO3, NaOH, and sodium alkoxide. To achieve similar values of the conversion, Ti(OEt)4 and Ti(OiPr)4 should be used in the cases of diethyl and dibutyl carbonates, respectively.