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Hydrochlorination of acetylene using a supported gold catalyst: A study of the reaction mechanism

Conte, Marco, Carley, Albert Frederick, Heirene, Clare, Willock, David James ORCID:, Johnston, Peter, Herzing, Andrew A., Kiely, Christopher J. ORCID: and Hutchings, Graham John ORCID: 2007. Hydrochlorination of acetylene using a supported gold catalyst: A study of the reaction mechanism. Journal of Catalysis 250 (2) , pp. 231-239. 10.1016/j.jcat.2007.06.018

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A detailed study of the hydrochlorination of acetylene and higher alkynes using a supported gold catalyst is described and discussed. A series of reactions using sequential exposure of the catalysts to C2H2 and HCl demonstrate that exposure to HCl before reaction of C2H2/HCl leads to enhanced activity, whereas exposure to C2H2 leads to deactivation. The reaction of higher alkynes is affected by steric factors, with the following trend in activity: acetylene (ca. 40% conversion) ≫ hex-1-yne (10%) > phenyl acetylene (7%) > hex-2-yne (2%). Using 1H NMR spectroscopy, we found that for hex-1-yne and phenyl acetylene, the anti-Markovnikov product is formed by anti-addition of HCl, but the Markovnikov products are equivalent for syn- and anti-addition of HCl. Thus, we investigated the reaction using deuterated substrates and confirmed that the products are formed by the anti-addition of HCl. The reaction mechanism is discussed in detail.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Cardiff Catalysis Institute (CCI)
Subjects: Q Science > QD Chemistry
Uncontrolled Keywords: Gold catalysis; Catalyst reactivation; Acetylene hydrochlorination
Publisher: Elsevier
ISSN: 0021-9517
Last Modified: 25 Oct 2022 07:59

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