Epoxidation of methyl oleate with molecular oxygen in the presence of aldehydes

✍ Scribed by Angela Köckritz; Michael Blumenstein; Andreas Martin

• Publisher: John Wiley and Sons
• Year: 2008
• Tongue: English
• Weight: 248 KB
• Volume: 110
• Category: Article
• ISSN: 1438-7697
• DOI: 10.1002/ejlt.200700279

✦ Synopsis

Abstract

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.