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Liquid-Phase Hydrogenation of Internal and Terminal Alkynes on Pd–Ag/Al2O3 Catalyst

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Abstract

The structure and catalytic properties of a bimetallic Pd–Ag/α-Al2O3 catalyst are studied in the liquid-phase hydrogenation of substituted internal and terminal alkynes using diphenylacetylene, phenylacetylene, 1-phenyl-1-propyne, and 1-phenyl-1-butyne as sample alkynes. IR spectroscopy of adsorbed CO, X‑ray diffraction (XRD), and electron microscopy were used to show that the active sites on the Pd–Ag nanoparticle surface are Pd1 sites. The synthesized Pd–Ag/α-Al2O3 catalyst shows a much higher selectivity in the hydrogenation of internal symmetric and asymmetric alkynes compared to the monometallic Pd/α‑Al2O3 sample. Also, it was found in the hydrogenation of diphenylacetylene and 1-phenyl-1-propyne on Pd–Ag/α-Al2O3 that the rate of the stage of desired olefin hydrogenation substantially decreases, which favors the kinetic control of the process.

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ACKNOWLEDGMENTS

The authors thank the Department of Structural Studies of the Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences for studying samples by electron microscopy.

Funding

The studies of the structure and morphology of catalysts by XRD, IR spectroscopy of adsorbed CO, as well as the study of the catalytic characteristics in the reaction of liquid-phase hydrogenation of alkyne substrates were supported by grant no. 16-29-10788 from the Russian Foundation for Basic Research. The method for synthesizing the Pd–Ag/α-Al2O3 bimetallic catalyst was developed with the financial support by grant no. 17-13-01526 from the Russian Science Foundation.

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Authors and Affiliations

  1. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991, Moscow, Russia

    A. V. Rassolov, G. O. Bragina, G. N. Baeva, N. S. Smirnova, A. V. Kazakov, I. S. Mashkovsky & A. Yu. Stakheev

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  1. A. V. Rassolov
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  2. G. O. Bragina
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  6. I. S. Mashkovsky
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  7. A. Yu. Stakheev
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Correspondence to A. Yu. Stakheev.

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Translated by Andrey Zeigarnik

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Rassolov, A.V., Bragina, G.O., Baeva, G.N. et al. Liquid-Phase Hydrogenation of Internal and Terminal Alkynes on Pd–Ag/Al2O3 Catalyst. Kinet Catal 60, 642–649 (2019). https://doi.org/10.1134/S0023158419050069

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