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

• 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
• ISSN: 1463-9262; 1463-9270
• DOI: 10.1039/c1gc15255f

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.