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

Pär Tufvesson; Dietlind Adlercreutz; Stefan Lundmark; Mircea Manea; Rajni Hatti-kaul

doi:10.1016/j.molcatb.2007.11.015

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

Pär Tufvesson, Dietlind Adlercreutz, Stefan Lundmark, Mircea Manea, Rajni Hatti-kaul

Research output: Contribution to journal › Journal article › Research › peer-review

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.
Keyword: Allyl ether,Glycidyl ether,Epoxidation,Peracid,Lipase

Original language	English
Journal	Journal of Molecular Catalysis B: Enzymatic
Volume	54
Pages (from-to)	1-6
ISSN	1381-1177
DOIs	https://doi.org/10.1016/j.molcatb.2007.11.015
Publication status	Published - 2008
Externally published	Yes

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title = "Production of glycidyl ethers by chemo-enzymatic epoxidation of allyl ethers",

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. Keyword: Allyl ether,Glycidyl ether,Epoxidation,Peracid,Lipase",

author = "P{\"a}r Tufvesson and Dietlind Adlercreutz and Stefan Lundmark and Mircea Manea and Rajni Hatti-kaul",

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doi = "10.1016/j.molcatb.2007.11.015",

language = "English",

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TY - JOUR

T1 - Production of glycidyl ethers by chemo-enzymatic epoxidation of allyl ethers

AU - Tufvesson, Pär

AU - Adlercreutz, Dietlind

AU - Lundmark, Stefan

AU - Manea, Mircea

AU - Hatti-kaul, Rajni

PY - 2008

Y1 - 2008

N2 - 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. Keyword: Allyl ether,Glycidyl ether,Epoxidation,Peracid,Lipase

AB - 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. Keyword: Allyl ether,Glycidyl ether,Epoxidation,Peracid,Lipase

U2 - 10.1016/j.molcatb.2007.11.015

DO - 10.1016/j.molcatb.2007.11.015

M3 - Journal article

SN - 1381-1177

VL - 54

SP - 1

EP - 6

JO - Journal of Molecular Catalysis B: Enzymatic

JF - Journal of Molecular Catalysis B: Enzymatic

ER -

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

Abstract

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