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Selective oxidation of alkenes using graphite-supported gold-palladium catalysts

Bawaked, Salem Mohammed, He, Qian ORCID:, Dummer, Nicholas ORCID:, Carley, Albert Frederick, Knight, David William, Bethell, Donald, Kiely, Christopher John ORCID: and Hutchings, Graham John ORCID: 2011. Selective oxidation of alkenes using graphite-supported gold-palladium catalysts. Catalysis Science & Technology 1 (5) , pp. 747-759. 10.1039/c1cy00122a

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Oxidation is an important route for the activation of chemical feedstocks for the synthesis of chemical intermediates. Alkene epoxidation by the electrophilic addition of oxygen to a carbon–carbon double bond is a major challenge in oxidation catalysis. In particular it is important to use molecular oxygen as the oxidant to avoid the formation of reagent by-products. We report the oxidation with air using graphite-supported gold-palladium catalysts of two alkenes, cis-cyclooctene, which gives mainly the epoxide, and crotyl alcohol (trans-but-2-en-1-ol). With cyclooctene, the reaction requires catalytic amounts of t-butyl hydroperoxide. The Au–Pd ratio has a major effect on the conversion with very low activities being associated with Au:Pd ratios of ca. 4:1 and 1:4 by weight. The selectivity to the epoxide is not affected by the Au:Pd ratio. With crotyl alcohol, t-butyl hydroperoxide was not required for activity. In the absence of Pd, crotonaldehyde was formed, but the introduction of Pd leads to an isomerisation pathway to 3-buten-1-ol being favoured over epoxidation and crotonaldehyde was a minor product.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Cardiff Catalysis Institute (CCI)
Subjects: Q Science > QD Chemistry
Publisher: Royal Society of Chemistry
ISSN: 2044-4753
Last Modified: 06 May 2023 01:26

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