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Catalysts 2017, 7(7), 193; doi:10.3390/catal7070193

Chiral Catalyst Deactivation during the Asymmetric Hydrogenation of Acetophenone

1
Department of Process Engineering, Universidad Autónoma Metropolitana—Iztapalapa, San Rafael Atlixco # 186, Ciudad de México C.P. 09340, Mexico
2
Facultad de Ciencias Químico Biológicas, Universidad Autónoma de Sinaloa, Josefa Ortiz de Domínguez S/N, Ciudad Universitaria, Culiacán Sinaloa C.P. 80013, Mexico
*
Author to whom correspondence should be addressed.
Academic Editor: Morris D. Argyle
Received: 18 May 2017 / Revised: 14 June 2017 / Accepted: 20 June 2017 / Published: 23 June 2017
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Abstract

Asymmetric hydrogenation in solution catalyzed by chiral catalysts is a powerful tool to obtain chiral secondary alcohols. It is possible to reach conversions and enantiomeric excesses close to 99%, but that frequently requires the use of non-optimal amounts of catalysts or long reaction times. That is in part caused by the lack of kinetic information needed for the design of large-scale reactors, including few reported details about catalyst deactivation. In this work, we present a kinetic model for the asymmetric hydrogenation in solution of acetophenone, a prochiral substrate, catalyzed by different bisphosphine-diamine Ru complexes. The experimental data was fitted with a first order model that includes first order deactivation of the catalyst and the presence of residual activity. The fit of the experimental data is very good, and an analysis of the kinetic and deactivation parameters gives further insight into the role of each ligand present in the Ru catalysts. This is the first report of a kinetic analysis of homogenous complexes’ catalysis including an analysis of their deactivation. View Full-Text
Keywords: asymmetric hydrogenation; deactivation; Ru complexes; kinetic modeling asymmetric hydrogenation; deactivation; Ru complexes; kinetic modeling
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Ruelas-Leyva, J.P.; Fuentes, G.A. Chiral Catalyst Deactivation during the Asymmetric Hydrogenation of Acetophenone. Catalysts 2017, 7, 193.

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