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

Gupta, Upendra Nath, Dummer, Nicholas Frank ORCID:, Pattisson, Samuel, Jenkins, Robert Leyshon, Knight, David William, Bethell, Donald and Hutchings, Graham John ORCID: 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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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)
Subjects: Q Science > QD Chemistry
Publisher: Kluwer
ISSN: 1011-372X
Last Modified: 06 May 2023 01:33

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