Issue 10, 2006
From the journal:

Green Chemistry

Lipase-mediated epoxidation utilizing urea–hydrogen peroxide in ethyl acetate†

Emanuel G. Ankudey,a   Horacio F. Olivo*b  and  Tonya L. Peeplesa  

* Corresponding authors

a Department of Chemical and Biochemical Engineering, The University of Iowa, Iowa City, IA 52242, USA

b Division of Medicinal and Natural Products Chemistry The University of Iowa, Iowa City, IA 52242, USA
E-mail: horacio-olivo@uiowa.edu
Fax: +1 (319) 335-8766
Tel: +1 (319) 335-8849

Abstract

A green method for alkene epoxidation based on the chemo-enzymatic perhydrolysis of carboxylic acids and esters has been optimized using Novozyme 435, the immobilized form of Candida antarctica lipase B, and the complex urea–hydrogen peroxide (UHP). UHP, an anhydrous form of hydrogen peroxide, has the potential of releasing hydrogen peroxide in a controlled manner and thus avoids the need to add the aqueous hydrogen peroxide slowly to the reaction mixture. The absence of water in the reaction media was also beneficial, because it minimized undesired reactions of the oxidized products. A minimum amount of enzyme was necessary to show the catalytic effect. On recycling, the enzyme maintained its activity up to six rounds of epoxidations. A range of alkenes was epoxidized by this method providing yields ranging from 75 to 100 percent.

Graphical abstract: Lipase-mediated epoxidation utilizing urea–hydrogen peroxide in ethyl acetate

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Article information

DOI
https://doi.org/10.1039/B604984B
Article type
Paper
Submitted
07 Apr 2006
Accepted
18 Jul 2006
First published
08 Aug 2006

Green Chem., 2006,8, 923-926

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Lipase-mediated epoxidation utilizing urea–hydrogen peroxide in ethyl acetate

E. G. Ankudey, H. F. Olivo and T. L. Peeples, Green Chem., 2006, 8, 923 DOI: 10.1039/B604984B

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