EPOXIDATION OF FATTY-ACID METHYL-ESTERS WITH ORGANIC HYDROPEROXIDES AND MOLYBDENUM OXIDE

Epoxidation of monounsaturated fatty acid methyl esters with an hydroperoxide and a catalyst was undertaken. Methyl oleate, elaidate, petroselinate, erucate, ricinoleate and 10-undecenoate were tested with cumyl- and tert-butylhydroperoxide. The heterogeneous alumina supported molybdenum oxide was used as a catalyst. In most cases, the reaction proceeded smoothly, giving only the expected epoxide in high yield. 10-Undecenoate, in which the double bond is less nucleophilic, exhibited lower selectivity and conversion rate. Methyl esters with a disubstituted double bond gave rise to pure stereoisomeric epoxide, corresponding to a syn-addition mechanism, as shown by the H-1-NMR spectra. Thus, the peracid as well as the catalytic hydroperoxide epoxidation work in the same way.