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

Tufvesson, Pär LU ; Adlercreutz, Dietlind LU ; Lundmark, Stefan; Manea, Mircea and Hatti-Kaul, Rajni LU (2008) In Journal of Molecular Catalysis B: Enzymatic 54(1-2). p.1-6
Abstract
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... (More)
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. (Less)
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
lipase, allyl ether, epoxidation, glycidyl ether, peracid
in
Journal of Molecular Catalysis B: Enzymatic
volume
54
issue
1-2
pages
1 - 6
publisher
Elsevier
external identifiers
  • wos:000257590000001
  • scopus:44649189738
ISSN
1873-3158
DOI
10.1016/j.molcatb.2007.11.015
language
English
LU publication?
yes
id
19d07118-98c0-414a-9a3a-e4958af8a624 (old id 1254666)
date added to LUP
2008-10-29 15:42:41
date last changed
2017-01-01 04:56:04
@article{19d07118-98c0-414a-9a3a-e4958af8a624,
  abstract     = {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.},
  author       = {Tufvesson, Pär and Adlercreutz, Dietlind and Lundmark, Stefan and Manea, Mircea and Hatti-Kaul, Rajni},
  issn         = {1873-3158},
  keyword      = {lipase,allyl ether,epoxidation,glycidyl ether,peracid},
  language     = {eng},
  number       = {1-2},
  pages        = {1--6},
  publisher    = {Elsevier},
  series       = {Journal of Molecular Catalysis B: Enzymatic},
  title        = {Production of glycidyl ethers by chemo-enzymatic epoxidation of allyl ethers},
  url          = {http://dx.doi.org/10.1016/j.molcatb.2007.11.015},
  volume       = {54},
  year         = {2008},
}