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Lipase mediated simultaneous esterification and epoxidation of oleic acid for the production of alkylepoxystearates

Orellana Coca Åkerman, Cecilia LU ; Billakanti, Jagan M.; Mattiasson, Bo LU and Hatti-Kaul, Rajni LU (2007) In Journal of Molecular Catalysis B: Enzymatic 44(3-4). p.133-137
Abstract
Epoxy alkylstearates were synthesized by lipase catalysed esterification and perhydrolysis followed by epoxidation of oleic acid in a one-pot process. Immobilized Candida antarctica lipase (Novozym 435) was used as the catalyst. The esterification reaction occurred relatively quickly and was followed by epoxidation of the alkyl ester and the remaining fatty acid. Higher degree of esterification was achieved with n-octanol, n-hexanol and n-butanol as compared to that with ethanol and iso-propanol. The rate and yield of epoxidation was enhanced with iso-propanol but was lowered with the other alcohols. The lipase suffered significant loss in activity during the reaction primarily due to hydrogen peroxide. The presence of alcohols, in... (More)
Epoxy alkylstearates were synthesized by lipase catalysed esterification and perhydrolysis followed by epoxidation of oleic acid in a one-pot process. Immobilized Candida antarctica lipase (Novozym 435) was used as the catalyst. The esterification reaction occurred relatively quickly and was followed by epoxidation of the alkyl ester and the remaining fatty acid. Higher degree of esterification was achieved with n-octanol, n-hexanol and n-butanol as compared to that with ethanol and iso-propanol. The rate and yield of epoxidation was enhanced with iso-propanol but was lowered with the other alcohols. The lipase suffered significant loss in activity during the reaction primarily due to hydrogen peroxide. The presence of alcohols, in particular ethanol. further contributed to the enzyme inactivation. The epoxidation reaction could be improved by step-wise addition of the lipase. (c) 2006 Elsevier B.V All rights reserved. (Less)
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
alkylepoxystearate, lipase, oleic acid, plasticizer
in
Journal of Molecular Catalysis B: Enzymatic
volume
44
issue
3-4
pages
133 - 137
publisher
Elsevier
external identifiers
  • wos:000244382300007
  • scopus:33846539109
ISSN
1873-3158
DOI
10.1016/j.molcatb.2006.09.002
language
English
LU publication?
yes
id
cadeed1d-1eab-4c9c-a82d-0671b46fb5a4 (old id 673641)
date added to LUP
2007-12-17 08:45:10
date last changed
2017-10-01 03:37:14
@article{cadeed1d-1eab-4c9c-a82d-0671b46fb5a4,
  abstract     = {Epoxy alkylstearates were synthesized by lipase catalysed esterification and perhydrolysis followed by epoxidation of oleic acid in a one-pot process. Immobilized Candida antarctica lipase (Novozym 435) was used as the catalyst. The esterification reaction occurred relatively quickly and was followed by epoxidation of the alkyl ester and the remaining fatty acid. Higher degree of esterification was achieved with n-octanol, n-hexanol and n-butanol as compared to that with ethanol and iso-propanol. The rate and yield of epoxidation was enhanced with iso-propanol but was lowered with the other alcohols. The lipase suffered significant loss in activity during the reaction primarily due to hydrogen peroxide. The presence of alcohols, in particular ethanol. further contributed to the enzyme inactivation. The epoxidation reaction could be improved by step-wise addition of the lipase. (c) 2006 Elsevier B.V All rights reserved.},
  author       = {Orellana Coca Åkerman, Cecilia and Billakanti, Jagan M. and Mattiasson, Bo and Hatti-Kaul, Rajni},
  issn         = {1873-3158},
  keyword      = {alkylepoxystearate,lipase,oleic acid,plasticizer},
  language     = {eng},
  number       = {3-4},
  pages        = {133--137},
  publisher    = {Elsevier},
  series       = {Journal of Molecular Catalysis B: Enzymatic},
  title        = {Lipase mediated simultaneous esterification and epoxidation of oleic acid for the production of alkylepoxystearates},
  url          = {http://dx.doi.org/10.1016/j.molcatb.2006.09.002},
  volume       = {44},
  year         = {2007},
}