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Facile synthesis of fatty acid esters in high yields

Bloomer, Scott ; Adlercreutz, Patrick LU orcid and Mattiasson, Bo LU (1992) In Enzyme and Microbial Technology 14(7). p.546-552
Abstract

The facile synthesis of esters by lipase-catalysed esterification of fatty acids and ethanol is demonstrated. Evaporation of the water generated in the reaction allowed the rapid production of esters of >99% yield in refluxing pentane or hexane. Water was trapped by condensing the refluxing vapor phase and passing it over activated molecular sieves in a reflux trap. High yields were rapidly obtained in synthesis of ethyl esters of oleic, linoleic, α-linolenic, and arachidonic acids without peroxidation of double bonds. The wax ester oleyl oleate was also synthesized rapidly with little peroxidation. A molar excess of 1.25 to 1.5 of ethanol allowed the most rapid ester synthesis. Synthesis of ethyl stearate was carried out on a... (More)

The facile synthesis of esters by lipase-catalysed esterification of fatty acids and ethanol is demonstrated. Evaporation of the water generated in the reaction allowed the rapid production of esters of >99% yield in refluxing pentane or hexane. Water was trapped by condensing the refluxing vapor phase and passing it over activated molecular sieves in a reflux trap. High yields were rapidly obtained in synthesis of ethyl esters of oleic, linoleic, α-linolenic, and arachidonic acids without peroxidation of double bonds. The wax ester oleyl oleate was also synthesized rapidly with little peroxidation. A molar excess of 1.25 to 1.5 of ethanol allowed the most rapid ester synthesis. Synthesis of ethyl stearate was carried out on a preparative scale (50 g). Greater than 99% conversion was obtained in 50 min.

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author
; and
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
Ester synthesis, lipase, peroxidation, reflux trap, water removal
in
Enzyme and Microbial Technology
volume
14
issue
7
pages
7 pages
publisher
Elsevier
external identifiers
  • scopus:0026898076
ISSN
0141-0229
DOI
10.1016/0141-0229(92)90125-8
language
English
LU publication?
yes
id
74e3f2c6-4ac4-4cd0-b1c4-c5996a6c315b
date added to LUP
2019-06-22 18:39:38
date last changed
2021-09-05 04:09:05
@article{74e3f2c6-4ac4-4cd0-b1c4-c5996a6c315b,
  abstract     = {{<p>The facile synthesis of esters by lipase-catalysed esterification of fatty acids and ethanol is demonstrated. Evaporation of the water generated in the reaction allowed the rapid production of esters of &gt;99% yield in refluxing pentane or hexane. Water was trapped by condensing the refluxing vapor phase and passing it over activated molecular sieves in a reflux trap. High yields were rapidly obtained in synthesis of ethyl esters of oleic, linoleic, α-linolenic, and arachidonic acids without peroxidation of double bonds. The wax ester oleyl oleate was also synthesized rapidly with little peroxidation. A molar excess of 1.25 to 1.5 of ethanol allowed the most rapid ester synthesis. Synthesis of ethyl stearate was carried out on a preparative scale (50 g). Greater than 99% conversion was obtained in 50 min.</p>}},
  author       = {{Bloomer, Scott and Adlercreutz, Patrick and Mattiasson, Bo}},
  issn         = {{0141-0229}},
  keywords     = {{Ester synthesis; lipase; peroxidation; reflux trap; water removal}},
  language     = {{eng}},
  month        = {{01}},
  number       = {{7}},
  pages        = {{546--552}},
  publisher    = {{Elsevier}},
  series       = {{Enzyme and Microbial Technology}},
  title        = {{Facile synthesis of fatty acid esters in high yields}},
  url          = {{http://dx.doi.org/10.1016/0141-0229(92)90125-8}},
  doi          = {{10.1016/0141-0229(92)90125-8}},
  volume       = {{14}},
  year         = {{1992}},
}