Abstract

AbstractEpoxidation 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 1H‐NMR spectra. Thus, the peracid as well as the catalytic hydroperoxide epoxidation work in the same way.

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