Solvent-free aerobic epoxidation of Dec-1-ene using gold/graphite as a catalyst

Gupta, Upendra Nath, Dummer, Nicholas Frank ORCID: https://orcid.org/0000-0002-0946-6304, Pattisson, Samuel, Jenkins, Robert Leyshon, Knight, David William, Bethell, Donald and Hutchings, Graham John ORCID: https://orcid.org/0000-0001-8885-1560 2015. Solvent-free aerobic epoxidation of Dec-1-ene using gold/graphite as a catalyst. Catalysis Letters 145 (2) , pp. 689-696. 10.1007/s10562-014-1425-z

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Abstract

The oxidation of dec-1-ene has been investigated using gold nanoparticles supported on graphite in the presence of a radical initiator (α,α-azobisisobutyronitrile) using oxygen from air as oxidant. We have investigated the influence of the reaction temperature (70–100 °C), catalyst mass and reaction time on the epoxide yield. In the absence of a radical initiator the reaction does not proceed, although auto-oxidation can occur at higher temperatures in the range studied. However, in the presence of an initiator, selective oxidation occurs and the initiator propagates the reaction through the formation of a peroxy-radical at the allylic C3 position. Graphite enhances the formation of the allylic products dec-1-en-3-ol, dec-1-en-3-one, and dec-2-en-1-ol; however, the addition of gold nanoparticles to the graphite, enhances formation of 1,2-epoxydecane. It is suggested that gold suppresses the formation of allylic products via a Russell termination.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Cardiff Catalysis Institute (CCI) Chemistry
Subjects:	Q Science > QD Chemistry
Publisher:	Kluwer
ISSN:	1011-372X
Last Modified:	06 May 2023 01:33
URI:	https://orca.cardiff.ac.uk/id/eprint/87750

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