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 › Article › peer-review

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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.

Original language	English
Pages (from-to)	1-6
Journal	Journal of Molecular Catalysis B: Enzymatic
Volume	54
Issue number	1-2
DOIs	https://doi.org/10.1016/j.molcatb.2007.11.015
Publication status	Published - 2008

Subject classification (UKÄ)

Industrial Biotechnology

Free keywords

lipase
allyl ether
epoxidation
glycidyl ether
peracid

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10.1016/j.molcatb.2007.11.015

Tufvesson2008author_version

1 Doctoral Thesis (compilation)

Lipase catalysed synthesis of speciality chemicals: technical, economical & environmental aspects
Tufvesson, P., 2008
Research output: Thesis › Doctoral Thesis (compilation)

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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.",

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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. (C) 2008 Elsevier B.V. All rights reserved.

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. (C) 2008 Elsevier B.V. All rights reserved.

KW - lipase

KW - allyl ether

KW - epoxidation

KW - glycidyl ether

KW - peracid

U2 - 10.1016/j.molcatb.2007.11.015

DO - 10.1016/j.molcatb.2007.11.015

M3 - Article

SN - 1873-3158

VL - 54

SP - 1

EP - 6

JO - Journal of Molecular Catalysis B: Enzymatic

JF - Journal of Molecular Catalysis B: Enzymatic

IS - 1-2

ER -

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

Abstract

Subject classification (UKÄ)

Free keywords

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Research output

Lipase catalysed synthesis of speciality chemicals: technical, economical & environmental aspects

Cite this