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Chemo-Enzymatic Epoxidation of Unsaturated Fatty Acids

Orellana Coca Åkerman, Cecilia LU (2006)
Abstract
Epoxy fatty acids are useful molecules and find a number of applications e.g. as PVC plasticisers and stabilisers, additives in polyurethane production, reactive diluents in paints, corrosion protection agents, etc.



Chemo-enzymatic epoxidation of unsaturated fatty acids has been studied; the peracid formation was catalysed by immobilised Candida antarctica lipase B (Novozym 435), and hydrogen peroxide was used as oxygen donor. A method based on HPLC for the analysis and quantification of unsaturated fatty acids and their epoxides was developed. The process of chemo-enzymatic epoxidation was optimised with an aim to minimise solvent use and maximise productivity. Epoxystearic acid and epoxystearic acid methyl ester were... (More)
Epoxy fatty acids are useful molecules and find a number of applications e.g. as PVC plasticisers and stabilisers, additives in polyurethane production, reactive diluents in paints, corrosion protection agents, etc.



Chemo-enzymatic epoxidation of unsaturated fatty acids has been studied; the peracid formation was catalysed by immobilised Candida antarctica lipase B (Novozym 435), and hydrogen peroxide was used as oxygen donor. A method based on HPLC for the analysis and quantification of unsaturated fatty acids and their epoxides was developed. The process of chemo-enzymatic epoxidation was optimised with an aim to minimise solvent use and maximise productivity. Epoxystearic acid and epoxystearic acid methyl ester were synthesised in very good yields in solvent free conditions, and is suggested to be a good alternative to the traditional epoxidation methods for epoxidation of fatty acids and oils.



Subsequently, the effect of the reaction parameters on the epoxidation of linoleic acid was investigated. Hydrogen peroxide was found to have a significant effect on the reaction rate and degree of epoxidation.



The same enzyme was then used to synthesise alkyl esters of epoxystearic acid, the esterification and perhydrolysis reactions being catalysed by the lipase in one pot. Butyl epoxystearate was synthesised with high yields.



The parameters affecting lipase activity and operational lifetime during the chemo-enzymatic epoxidation were investigated. The high concentration of hydrogen peroxide used for the reaction inactivates the enzyme at high temperature, hence limiting recycling of the biocatalyst. Results suggest that temperature control and careful dosage of hydrogen peroxide are among the most important parameters for industrial chemo-enzymatic epoxidation. (Less)
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author
supervisor
opponent
  • Professor Woodley, John, University College London (UCL)
organization
publishing date
type
Thesis
publication status
published
subject
keywords
Bioteknik, Biotechnology, solvent-free process., Candida antarctica lipase B esterification, chemo-enzymatic epoxidation, Unsaturated fatty acids, epoxides
publisher
Biotechnology, Lund University
defense location
Lecture Hall B Centre for Chemistry and Chemical Engineering Getingevägen 60 Lund Institute of Technology
defense date
2006-01-20 10:30
external identifiers
  • other:ISRN: LUTKDH/TKBT--06/1090--SE
ISBN
91-89627-37-7
language
English
LU publication?
yes
id
98d546d9-7f7c-4a67-83be-d5dfe9d7aba5 (old id 546045)
date added to LUP
2007-10-13 11:26:55
date last changed
2016-09-19 08:45:02
@phdthesis{98d546d9-7f7c-4a67-83be-d5dfe9d7aba5,
  abstract     = {Epoxy fatty acids are useful molecules and find a number of applications e.g. as PVC plasticisers and stabilisers, additives in polyurethane production, reactive diluents in paints, corrosion protection agents, etc.<br/><br>
<br/><br>
Chemo-enzymatic epoxidation of unsaturated fatty acids has been studied; the peracid formation was catalysed by immobilised Candida antarctica lipase B (Novozym 435), and hydrogen peroxide was used as oxygen donor. A method based on HPLC for the analysis and quantification of unsaturated fatty acids and their epoxides was developed. The process of chemo-enzymatic epoxidation was optimised with an aim to minimise solvent use and maximise productivity. Epoxystearic acid and epoxystearic acid methyl ester were synthesised in very good yields in solvent free conditions, and is suggested to be a good alternative to the traditional epoxidation methods for epoxidation of fatty acids and oils.<br/><br>
<br/><br>
Subsequently, the effect of the reaction parameters on the epoxidation of linoleic acid was investigated. Hydrogen peroxide was found to have a significant effect on the reaction rate and degree of epoxidation.<br/><br>
<br/><br>
The same enzyme was then used to synthesise alkyl esters of epoxystearic acid, the esterification and perhydrolysis reactions being catalysed by the lipase in one pot. Butyl epoxystearate was synthesised with high yields.<br/><br>
<br/><br>
The parameters affecting lipase activity and operational lifetime during the chemo-enzymatic epoxidation were investigated. The high concentration of hydrogen peroxide used for the reaction inactivates the enzyme at high temperature, hence limiting recycling of the biocatalyst. Results suggest that temperature control and careful dosage of hydrogen peroxide are among the most important parameters for industrial chemo-enzymatic epoxidation.},
  author       = {Orellana Coca Åkerman, Cecilia},
  isbn         = {91-89627-37-7},
  keyword      = {Bioteknik,Biotechnology,solvent-free process.,Candida antarctica lipase B esterification,chemo-enzymatic epoxidation,Unsaturated fatty acids,epoxides},
  language     = {eng},
  publisher    = {Biotechnology, Lund University},
  school       = {Lund University},
  title        = {Chemo-Enzymatic Epoxidation of Unsaturated Fatty Acids},
  year         = {2006},
}