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Issue 15, 2017
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Kinetic investigation into the chemoselective hydrogenation of α,β-unsaturated carbonyl compounds catalyzed by Ni(0) nanoparticles

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Abstract

A series of Ni(0) nanocatalysts was prepared from a Ni(COD)2 complex in the presence of different stabilizers (hexadecylamine, polyvinylpyrrolidone (PVP), PVP/triphenylphosphine, octanoic acid and stearic acid) for their evaluation in the selective hydrogenation reaction of α,β-unsaturated carbonyl compounds by H2 under mild reaction conditions, i.e., low H2 pressure, temperature and catalyst loading. All nanocatalysts were active in reducing only the C[double bond, length as m-dash]C bond and this chemoselectivity was attributed to the reduced nature of the Ni-NPs surface. Moreover, the hydrogenation reaction rate appeared to be sensitive to ligand type, with the carboxylic acid-stabilized systems showing the best performances. A full kinetic investigation into the t-chalcone chemoselective reduction of the C[double bond, length as m-dash]C bond, with the best catalyst (Ni-octanoic acid) revealed that the rate-determining step is the hydrogenation of the adsorbed substrate on the NPs surface, following a Horiuti–Polanyi type of mechanism. Regarding sustainable chemistry concerns, the best catalyst could be reused up to 10 times without significant loss of activity.

Graphical abstract: Kinetic investigation into the chemoselective hydrogenation of α,β-unsaturated carbonyl compounds catalyzed by Ni(0) nanoparticles

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Publication details

The article was received on 21 Feb 2017, accepted on 17 Mar 2017 and first published on 17 Mar 2017


Article type: Paper
DOI: 10.1039/C7DT00649G
Citation: Dalton Trans., 2017,46, 5082-5090
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    Kinetic investigation into the chemoselective hydrogenation of α,β-unsaturated carbonyl compounds catalyzed by Ni(0) nanoparticles

    L. Zaramello, B. L. Albuquerque, J. B. Domingos and K. Philippot, Dalton Trans., 2017, 46, 5082
    DOI: 10.1039/C7DT00649G

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