Epoxidation and Baeyer―Villiger oxidation using hydrogen peroxide and a lipase dissolved in ionic liquids

Epoxidation and Baeyer-Villiger oxidation of olefins and (cyclic) ketones were successfully carried out in hydrogen-bond-donating (HBD) ionic liquids, using a lipase-catalysed cascade and hydrogen peroxide as the terminal oxidant. The effect of the ionic liquids turned out to be twofold. The HBD ion...

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Published in:Green chemistry : an international journal and green chemistry resource : GC 2011-01, Vol.13 (8), p.2154-2160
Main Authors: KOTLEWSKA, Aleksandra J, VAN RANTWIJK, Fred, SHELDON, Roger A, ARENDS, Isabel W. C. E
Format: Article
Language:English
Subjects:
Bioconversions. Hemisynthesis
Biological and medical sciences
Biotechnology
Candida antarctica
Chemical process industry
Chemistry
Exact sciences and technology
Fundamental and applied biological sciences. Psychology
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Mechanisms. Catalysis. Electron transfer. Models
Methods. Procedures. Technologies
Molecular biophysics
Organic chemistry
Physical chemistry in biology
Preparations and properties
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description Epoxidation and Baeyer-Villiger oxidation of olefins and (cyclic) ketones were successfully carried out in hydrogen-bond-donating (HBD) ionic liquids, using a lipase-catalysed cascade and hydrogen peroxide as the terminal oxidant. The effect of the ionic liquids turned out to be twofold. The HBD ionic liquids exhibited a substantial positive solvent effect on the second step of the cascade, namely the oxygen transfer by peracid. In addition, we found that the Candida antarctica B lipase (CaLB) dissolved in 1-(3-hydroxypropyl)-3-methyl imidazolium nitrate 1a and 1-butyl-3-methylimidazolium nitrate 2a. This stable enzyme-ionic liquid solution opens the possibility for continuous chemical processing.
doi_str_mv 10.1039/c1gc15255f
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source Royal Society of Chemistry
subjects Bioconversions. Hemisynthesis
Biological and medical sciences
Biotechnology
Candida antarctica
Chemical process industry
Chemistry
Exact sciences and technology
Fundamental and applied biological sciences. Psychology
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Mechanisms. Catalysis. Electron transfer. Models
Methods. Procedures. Technologies
Molecular biophysics
Organic chemistry
Physical chemistry in biology
Preparations and properties
title Epoxidation and Baeyer―Villiger oxidation using hydrogen peroxide and a lipase dissolved in ionic liquids
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