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Epoxidation of Fatty Acid Methyl Esters with Organic Hydroperoxides and Molybdenum Oxide

✍ Scribed by Ucciani, E. ;Debal, A. ;Rafaralahitsimba, G.

Publisher: John Wiley and Sons
Year: 1993
Weight: 380 KB
Volume: 95
Category: Article
ISSN: 0931-5985
DOI: 10.1002/lipi.19930950608

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✦ Synopsis

d E . U c c i a n i *

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-NMR spectra. Thus, the peracid as well as the catalytic hydroperoxide epoxidation work in the same way.

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