Issue 12, 2009

Efficient epoxidation of alkenes with hydrogen peroxide, lactone, and lipase

Abstract

A green and efficient oxidation system containing hydrogen peroxide, lactone, and lipase was developed for the epoxidation of alkenes. A variety of alkenes was oxidized with this system, giving 87–95% analytical yield of the corresponding epoxides. The epoxidation occurred vialipase-catalyzed formation of hydroxy peroxy acid from lactone, without release of any harmful short-chain acid and alcohol, and in situ chemical oxidation of alkenes. Both hydrophilic ε-caprolactone and hydrophobic δ-decanolactone were shown to be good substrates to produce hydroxy peracids and good reaction solvents, and the method is suitable for the oxidation in either single phase or two-liquid phase. In comparison with other lipase-mediated oxidation systems, the new oxidation system gave higher yield, higher efficiency, and higher enzyme stability.

Graphical abstract: Efficient epoxidation of alkenes with hydrogen peroxide, lactone, and lipase

Supplementary files

Article information

Article type
Paper
Submitted
02 Jul 2009
Accepted
28 Aug 2009
First published
30 Sep 2009

Green Chem., 2009,11, 2047-2051

Efficient epoxidation of alkenes with hydrogen peroxide, lactone, and lipase

Y. Xu, N. R. B. J. Khaw and Z. Li, Green Chem., 2009, 11, 2047 DOI: 10.1039/B913077B

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