Structure/activity relationships applied to the hydrogenation of α,β-unsaturated carbonyls: The hydrogenation of 3-butyne-2-one over alumina-supported palladium catalysts

Morisse, C. G.A., McInroy, A. R., Anderson, C., Mitchell, C. J., Parker, S. F. and Lennon, D. (2017) Structure/activity relationships applied to the hydrogenation of α,β-unsaturated carbonyls: The hydrogenation of 3-butyne-2-one over alumina-supported palladium catalysts. Catalysis Today, 283, pp. 110-118. (doi: 10.1016/j.cattod.2016.02.028)

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Abstract

The gas phase hydrogenation of 3-butyne-2-one, an alkynic ketone, over two alumina-supported palladium catalysts is investigated using infrared spectroscopy in a batch reactor at 373 K. The mean particle size of the palladium crystallites of the two catalysts are comparable (2.4 ± 0.1 nm). One catalyst (Pd(NO3)2/Al2O3) is prepared from a palladium(II) nitrate precursor, whereas the other catalyst (PdCl2/Al2O3) is prepared using palladium(II) chloride as the Pd precursor compound. A three-stage sequential process is observed with the Pd(NO3)2/Al2O3 catalyst facilitating complete reduction all the way through to 2-butanol. However, hydrogenation stops at 2-butanone with the PdCl2/Al2O3 catalyst. The inability of the PdCl2/Al2O3 catalyst to reduce 2-butanone is attributed to the inaccessibility of edge sites on this catalyst, which are blocked by chlorine retention originating from the catalyst’s preparative process. The reaction profiles observed for the hydrogenation of this alkynic ketone are consistent with the site-selective chemistry recently reported for the hydrogenation of crotonaldehyde, an alkenic aldehyde, over the same two catalysts. Thus, it is suggested that a previously postulated structure/activity relationship may be generic for the hydrogenation of α,β-unsaturated carbonyl compounds over supported Pd catalysts.

Item Type:Articles
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Lennon, Professor David and Morisse, Mr Clement
Authors: Morisse, C. G.A., McInroy, A. R., Anderson, C., Mitchell, C. J., Parker, S. F., and Lennon, D.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Catalysis Today
Publisher:Elsevier
ISSN:0920-5861
ISSN (Online):1873-4308
Published Online:15 March 2016
Copyright Holders:Copyright © 2017 The Authors
First Published:First published in Catalysis Today 283:110-118
Publisher Policy:Reproduced under a Creative Commons License

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Project CodeAward NoProject NamePrincipal InvestigatorFunder's NameFunder RefLead Dept
548571Acquisition of the INS spectra for a series of C4 molecules relevant to metal catalysed hydrogenation reactions (RB810348)David LennonScience & Technologies Facilities Council (STFC)RB810348CHEM - CHEMISTRY