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Issue 5, 2012
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Mechanistic insights in the olefin epoxidation with cyclohexyl hydroperoxide

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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

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Publication details

The article was received on 11 Nov 2011, accepted on 06 Jan 2012 and first published on 06 Jan 2012


Article type: Paper
DOI: 10.1039/C2CY00455K
Catal. Sci. Technol., 2012,2, 951-960

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    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

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