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Epoxidation of methyl oleate with molecular oxygen in the presence of aldehydes
Author(s) -
Köckritz Angela,
Blumenstein Michael,
Martin Andreas
Publication year - 2008
Publication title -
european journal of lipid science and technology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.614
H-Index - 94
eISSN - 1438-9312
pISSN - 1438-7697
DOI - 10.1002/ejlt.200700279
Subject(s) - epoxide , chemistry , hexanal , aldehyde , yield (engineering) , organic chemistry , solvent , catalysis , materials science , metallurgy
The epoxidation of methyl oleate with molecular oxygen in the presence of aldehydes was investigated and optimized. Epoxide yields up to 99% were observed in organic solvents. The preponderant radical reaction was started by a single organic radical chain initiator, without using a metal catalyst. The radical character of the reaction was revealed by the concurrent occurrence of trans and cis epoxides and by the prevention of epoxide formation through a radical scavenger. Both branched aldehydes and the linear aldehyde n ‐hexanal were well suited in organic solvents. The linear n ‐hexanal enabled also a superior epoxide yield of 78% in the green solvent water. The oxidation of high‐oleic sunflower oil under the same conditions with n ‐hexanal yielded 39% epoxide groups.