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Poisoning and Reuse of Supported Precious Metal Catalysts in the Hydrogenation of N-Heterocycles Part I: Ruthenium-Catalysed Hydrogenation of 1-Methylpyrrole

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Abstract

Poisoning phenomena of heterogeneous, supported precious metal catalysts caused by nitrogen were investigated in the liquid-phase hydrogenation of 1-methylpyrrole (MP) to 1-methylpyrrolidine (MPD) over ruthenium on carbon, in non-acidic medium (methanol), at 10 bar and 25–60 °C. Reusing a spent, unregenerated 5% Ru/C catalyst, it was found that the activity of catalyst and the conversion of model substrate were strongly dependent on the amount of catalyst and the number of recycling, respectively. During the first reuse of this ruthenium catalyst, surprisingly, it showed high activity already at room temperature contrary to the fresh catalyst which worked at only 60 °C. This unexpected catalytic behaviour was studied by XRD and XPS methods which revealed the existence of a fine RuO2 layer on the surface of the catalytic metal in the fresh catalyst.

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Acknowledgements

The authors thank Dr. Antal Sárkány for determining the catalyst dispersion, as well as Dr. László Vida for GC–MS measurements.

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Authors and Affiliations

  1. Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Budafoki út 8, Budapest, 1111, Hungary

    László Hegedűs & Kristóf Szőke-Molnár

  2. Environmental Analytical and Geoanalytical Research Group, Szentágothai Research Centre, University of Pécs, Ifjúság út 20, Pécs, 7624, Hungary

    István E. Sajó

  3. Surface Chemistry and Catalysis Department, Institute for Energy Security and Environmental Safety, Centre for Energy Research, Hungarian Academy of Sciences, Konkoly-Thege Miklós út 29-33, 1121, Budapest, Hungary

    Dávid Ferenc Srankó & Zoltán Schay

Authors
  1. László Hegedűs
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  2. Kristóf Szőke-Molnár
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  3. István E. Sajó
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  4. Dávid Ferenc Srankó
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  5. Zoltán Schay
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Correspondence to László Hegedűs.

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The authors declare no competing financial interest.

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Dedicated to the memory of Dr. Tibor Máthé, an excellent researcher and inventor, who passed away 17 years ago.

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Hegedűs, L., Szőke-Molnár, K., Sajó, I.E. et al. Poisoning and Reuse of Supported Precious Metal Catalysts in the Hydrogenation of N-Heterocycles Part I: Ruthenium-Catalysed Hydrogenation of 1-Methylpyrrole. Catal Lett 148, 1939–1950 (2018). https://doi.org/10.1007/s10562-018-2406-4

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  • DOI: https://doi.org/10.1007/s10562-018-2406-4

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