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Baeyer-Villiger Oxidation of Cyclohexanone in Aqueous Medium with In Situ Generation of Peracid Catalyzed by Perhydrolase CLEA

Chávez, Georgina LU ; Rasmussen, Jo-Anne; Janssen, Michiel; Mamo, Gashaw LU ; Hatti-Kaul, Rajni LU and Sheldon, Roger A. (2014) In Topics in Catalysis 57(5). p.349-355
Abstract
A perhydrolase, immobilized as a cross linked enzyme aggregate (CLEA), was employed to catalyze the in situ formation of peracetic acid (PAA) from ethylene glycol diacetate (EGDA) and hydrogen peroxide. The produced PAA was used for the Baeyer-Villiger oxidation of cyclohexanone, which afforded caprolactone in 63 % yield. The effect of type and amount of acyl donor, solvent, pH, temperature and ratio of cyclohexanone to hydrogen peroxide on the production of caprolactone was studied. The highest caprolactone yield was obtained with 100 mM EGDA as the acyl donor at pH 6 and room temperature using a ratio of cyclohexanone to hydrogen peroxide ratio of 1:4. Interestingly, the perhydrolase CLEA exhibited the highest activity in aqueous medium... (More)
A perhydrolase, immobilized as a cross linked enzyme aggregate (CLEA), was employed to catalyze the in situ formation of peracetic acid (PAA) from ethylene glycol diacetate (EGDA) and hydrogen peroxide. The produced PAA was used for the Baeyer-Villiger oxidation of cyclohexanone, which afforded caprolactone in 63 % yield. The effect of type and amount of acyl donor, solvent, pH, temperature and ratio of cyclohexanone to hydrogen peroxide on the production of caprolactone was studied. The highest caprolactone yield was obtained with 100 mM EGDA as the acyl donor at pH 6 and room temperature using a ratio of cyclohexanone to hydrogen peroxide ratio of 1:4. Interestingly, the perhydrolase CLEA exhibited the highest activity in aqueous medium in contrast to the well studied lipase B from Candida antarctica. The perhydrolase CLEA proved to be a very efficient catalyst; the K (m) and V-max values were 118 mM and 56.3 mu mol min(-1), respectively. (Less)
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
Perhydrolase, CLEA, Baeyer-Villiger, Oxidation, Epoxidation, Aqueous, medium, Caprolactone
in
Topics in Catalysis
volume
57
issue
5
pages
349 - 355
publisher
Kluwer
external identifiers
  • wos:000331698100007
  • scopus:84896560488
ISSN
1572-9028
DOI
10.1007/s11244-013-0190-3
language
English
LU publication?
yes
id
e3425194-bd23-438d-83ba-cfce23baa585 (old id 4417787)
date added to LUP
2014-05-05 11:22:00
date last changed
2017-04-30 11:16:28
@article{e3425194-bd23-438d-83ba-cfce23baa585,
  abstract     = {A perhydrolase, immobilized as a cross linked enzyme aggregate (CLEA), was employed to catalyze the in situ formation of peracetic acid (PAA) from ethylene glycol diacetate (EGDA) and hydrogen peroxide. The produced PAA was used for the Baeyer-Villiger oxidation of cyclohexanone, which afforded caprolactone in 63 % yield. The effect of type and amount of acyl donor, solvent, pH, temperature and ratio of cyclohexanone to hydrogen peroxide on the production of caprolactone was studied. The highest caprolactone yield was obtained with 100 mM EGDA as the acyl donor at pH 6 and room temperature using a ratio of cyclohexanone to hydrogen peroxide ratio of 1:4. Interestingly, the perhydrolase CLEA exhibited the highest activity in aqueous medium in contrast to the well studied lipase B from Candida antarctica. The perhydrolase CLEA proved to be a very efficient catalyst; the K (m) and V-max values were 118 mM and 56.3 mu mol min(-1), respectively.},
  author       = {Chávez, Georgina and Rasmussen, Jo-Anne and Janssen, Michiel and Mamo, Gashaw and Hatti-Kaul, Rajni and Sheldon, Roger A.},
  issn         = {1572-9028},
  keyword      = {Perhydrolase,CLEA,Baeyer-Villiger,Oxidation,Epoxidation,Aqueous,medium,Caprolactone},
  language     = {eng},
  number       = {5},
  pages        = {349--355},
  publisher    = {Kluwer},
  series       = {Topics in Catalysis},
  title        = {Baeyer-Villiger Oxidation of Cyclohexanone in Aqueous Medium with In Situ Generation of Peracid Catalyzed by Perhydrolase CLEA},
  url          = {http://dx.doi.org/10.1007/s11244-013-0190-3},
  volume       = {57},
  year         = {2014},
}