Jump to main content
Jump to site search
Access to RSC content Close the message box

Continue to access RSC content when you are not at your institution. Follow our step-by-step guide.


Issue 5, 2012
Previous Article Next Article

Mechanistic insights in the olefin epoxidation with cyclohexyl hydroperoxide

Author affiliations

Abstract

Olefin epoxidation with cyclohexyl hydroperoxide offers great perspective in increasing the yield from industrial cyclohexane oxidation and the production of epoxides in an apolar medium. Two competing hydroperoxide conversion routes, namely direct epoxidation and thermal decomposition, were identified. The formation of radicals seemed to play a role in both mechanisms. However, olefin epoxidation was found to solely take place at the catalyst. Allylic oxidation of cyclohexene occurs under reaction conditions primarily by molecular oxygen and only constitutes a minor route. The presence of molecular oxygen was found to increase the overall yield of the process by solvent oxidation yielding new cyclohexyl hydroperoxide. Hydrolysis and isomerization of the epoxide were found to be negligible reactions, although the epoxide gets converted at higher concentrations, presumably by the radical initiated polymerization. UV-Vis spectroscopy provided proof for the formation of titanium-hydroperoxide species as the active catalytic site in the direct epoxidation reaction.

Graphical abstract: Mechanistic insights in the olefin epoxidation with cyclohexyl hydroperoxide

Back to tab navigation

Supplementary files

Article information


Submitted
11 Nov 2011
Accepted
06 Jan 2012
First published
06 Jan 2012

Catal. Sci. Technol., 2012,2, 951-960
Article type
Paper

Mechanistic insights in the olefin epoxidation with cyclohexyl hydroperoxide

B. P. C. Hereijgers, R. F. Parton and B. M. Weckhuysen, Catal. Sci. Technol., 2012, 2, 951
DOI: 10.1039/C2CY00455K

Social activity

Search articles by author

Spotlight

Advertisements