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Chemo-enzymatic epoxidation of linoleic acid: Parameters influencing the reaction

Orellana Coca Åkerman, Cecilia LU ; Camocho, Samuel; Adlercreutz, Dietlind LU ; Mattiasson, Bo LU and Hatti-Kaul, Rajni LU (2005) In European Journal of Lipid Science and Technology 107(12). p.864-870
Abstract
The effect of reaction parameters on lipase-mediated chemo-enzymatic epoxidation of linoleic acid was investigated. Hydrogen peroxide was found to have the most significant effect on the reaction rate and degree of epoxidation. Excess of hydrogen peroxide with respect to the amount of double bonds was necessary in order to yield total conversion within a short time period, as well as at temperatures above 50 °C to compensate for hydrogen peroxide decomposition. However, prolonged incubation with high excess of hydrogen peroxide leads to the accumulation of peracids in the final product. The reaction rate increased also with increasing hydrogen peroxide concentration (between 10 and 50 wt-%); however, at the expense of enzyme inactivation.... (More)
The effect of reaction parameters on lipase-mediated chemo-enzymatic epoxidation of linoleic acid was investigated. Hydrogen peroxide was found to have the most significant effect on the reaction rate and degree of epoxidation. Excess of hydrogen peroxide with respect to the amount of double bonds was necessary in order to yield total conversion within a short time period, as well as at temperatures above 50 °C to compensate for hydrogen peroxide decomposition. However, prolonged incubation with high excess of hydrogen peroxide leads to the accumulation of peracids in the final product. The reaction rate increased also with increasing hydrogen peroxide concentration (between 10 and 50 wt-%); however, at the expense of enzyme inactivation. Linoleic acid was completely epoxidized when used at a concentration of 0.5-2 M in toluene at 30 °C, while in a solvent-free medium, the reaction was not complete due to the formation of a solid or a highly viscous oily phase, creating mass transfer limitations. Increasing the temperature up to 60 °C also improved the rate of epoxide formation. (Less)
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
European Journal of Lipid Science and Technology
volume
107
issue
12
pages
864 - 870
publisher
John Wiley & Sons
external identifiers
  • wos:000234419900004
  • scopus:30144434036
ISSN
1438-7697
DOI
10.1002/ejlt.200500253
language
English
LU publication?
yes
id
00918b45-093a-4b58-b90b-263edfcd3085 (old id 158649)
date added to LUP
2007-07-02 15:50:06
date last changed
2017-07-30 03:32:13
@article{00918b45-093a-4b58-b90b-263edfcd3085,
  abstract     = {The effect of reaction parameters on lipase-mediated chemo-enzymatic epoxidation of linoleic acid was investigated. Hydrogen peroxide was found to have the most significant effect on the reaction rate and degree of epoxidation. Excess of hydrogen peroxide with respect to the amount of double bonds was necessary in order to yield total conversion within a short time period, as well as at temperatures above 50 °C to compensate for hydrogen peroxide decomposition. However, prolonged incubation with high excess of hydrogen peroxide leads to the accumulation of peracids in the final product. The reaction rate increased also with increasing hydrogen peroxide concentration (between 10 and 50 wt-%); however, at the expense of enzyme inactivation. Linoleic acid was completely epoxidized when used at a concentration of 0.5-2 M in toluene at 30 °C, while in a solvent-free medium, the reaction was not complete due to the formation of a solid or a highly viscous oily phase, creating mass transfer limitations. Increasing the temperature up to 60 °C also improved the rate of epoxide formation.},
  author       = {Orellana Coca Åkerman, Cecilia and Camocho, Samuel and Adlercreutz, Dietlind and Mattiasson, Bo and Hatti-Kaul, Rajni},
  issn         = {1438-7697},
  language     = {eng},
  number       = {12},
  pages        = {864--870},
  publisher    = {John Wiley & Sons},
  series       = {European Journal of Lipid Science and Technology},
  title        = {Chemo-enzymatic epoxidation of linoleic acid: Parameters influencing the reaction},
  url          = {http://dx.doi.org/10.1002/ejlt.200500253},
  volume       = {107},
  year         = {2005},
}