Production of glycidyl ethers by chemo-enzymatic epoxidation of allyl ethers

Production of glycidyl ethers is industrially carried Out by reacting alcohols with epichlorhydrin, a potentially carcinogenic compound. This paper investigates a less hazardous alternative-that of a chemo-enzymatic process in which Candida antarctica lipase B catalysed generation of peracid from a...

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Bibliographic Details
Published in:Journal of Molecular Catalysis B: Enzymatic
Main Authors: Tufvesson, Pär, Adlercreutz, Dietlind, Lundmark, Stefan, Manea, Mircea, Hatti-Kaul, Rajni
Format: Article in Journal/Newspaper
Language:English
Published: Elsevier 2008
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Online Access:https://lup.lub.lu.se/record/1254666
https://doi.org/10.1016/j.molcatb.2007.11.015
https://portal.research.lu.se/files/2825436/1268339.pdf
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Summary:Production of glycidyl ethers is industrially carried Out by reacting alcohols with epichlorhydrin, a potentially carcinogenic compound. This paper investigates a less hazardous alternative-that of a chemo-enzymatic process in which Candida antarctica lipase B catalysed generation of peracid from a carboxylic acid is followed by a Prileshajev epoxidation of the corresponding allyl ether. Trimethylolpropane monoallyl ether (TMPME) was used as a model substrate. A maximal epoxide product yield of 77% was achieved through the optimization of temperature. acid concentration and hydrogen peroxide concentration. Peracid formation was considerably faster than the subsequent epoxidation step, and accumulation of the peracid was Found to be important to drive the epoxidation forward. (C) 2008 Elsevier B.V. All rights reserved.