Conte, Marco, Carley, Albert Frederick, Heirene, Clare, Willock, David James  ORCID: https://orcid.org/0000-0002-8893-1090, Johnston, Peter, Herzing, Andrew A., Kiely, Christopher J. ORCID: https://orcid.org/0000-0001-5412-0970 and Hutchings, Graham John ORCID: https://orcid.org/0000-0001-8885-1560
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
|
Abstract
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) Chemistry |
| 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 |
| URI: | https://orca.cardiff.ac.uk/id/eprint/51012 |
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