Selective Hydrogenation of Diketones on Supported Transition Metal Catalysts

The hydrogenation of α-diketones yields α-hydroxyketones or vic-diols, both compounds of great interest in fine chemistry. The reaction tests were the liquid phase hydrogenation of 2,3-butanedione and 2,3-pentanedione at mild conditions. The objectives of this work were evaluating the effect over th...

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Bibliographic Details
Published in:Catalysis letters 2020-02, Vol.150 (2), p.461-470
Main Authors: Carrara, N., Badano, J. M., Vailard, S., Vera, C., Quiroga, M.
Format: Article
Language:English
Subjects:
Activated carbon
Adsorption
Catalysis
Catalysts
Chemical properties
Chemistry
Chemistry and Materials Science
Diketones
Diols
Enols
Hydrogenation
Industrial Chemistry/Chemical Engineering
Ketones
Liquid phases
Metal catalysts
NMR
Nuclear magnetic resonance
Olefins
Organic chemistry
Organometallic Chemistry
Palladium
Palladium catalysts
Phase transitions
Physical Chemistry
Platinum
Selectivity
Transition metal compounds
Transition metals
X ray photoelectron spectroscopy
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Summary:The hydrogenation of α-diketones yields α-hydroxyketones or vic-diols, both compounds of great interest in fine chemistry. The reaction tests were the liquid phase hydrogenation of 2,3-butanedione and 2,3-pentanedione at mild conditions. The objectives of this work were evaluating the effect over the activity and selectivity of: (a) different transition metallic phase based catalysts supported on activated carbon, (b) the symmetry of the reactants and (c) solvents. The physicochemical characterization of the catalysts was carried out by ICP, XRD, TEM, N 2 adsorption and XPS. The keto-enol equilibrium of diketones was studied by 1H-NMR. All the catalysts were active in both reactions. In terms of activity, Pt and Rh were the best active phases. For both reactants the highest selectivity towards hydroxyketones were achieved with Pd, while Ru was the most selective towards the diol. Both the activity and selectivity followed similar patterns in the hydrogenation of both diketones. The greater activity of Pt was attributed to the high dispersion of the active metal phase in this catalyst and the high efficiency of Pt for C = O bond reduction. The high selectivity of the Pd catalysts towards the intermediate product was attributed to many effects: (i) a lower interaction of the hydroxyketone with the active site as compared to the diketone, (ii) the easy reducibility of the C = C double bond on Pd, provided by the keto-enol tautomerism of diketones. Graphic Abstract
ISSN:1011-372X
1572-879X
DOI:10.1007/s10562-019-02983-5