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Selective Hydrogenation of 5-Vinyl-2-Norbornene to 2-Vinylnorbornane

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Abstract

The possibility of selective hydrogenation of 5-vinyl-2-norbornene to 2-vinylnorbornane with hydrazine hydrate in the presence of an oxidant (oxygen or air oxygen) and a hydrazine hydrate decomposition catalyst has been investigated. It has been shown that the hydrazine hydrate/oxidant/catalyst system makes it possible to hydrogenate the endocyclic (norbornene) double bond of 5-vinyl-2-norbornene to form 2-vinylnorbornane with a selectivity of up to 95% at the 5-vinyl-2-norbornene conversion above 99%. As catalysts for the oxidative decomposition of hydrazine hydrate, Pd/C and copper salts have been tested. The influence of the conditions of 5-vinyl-2-norbornene hydrogenation to 2-vinylnorbornane on the selectivity of the process and the product yield has been studied. An optimized and preparatively convenient procedure for the selective production of 2-vinylnorbornane has been developed.

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ACKNOWLEDGMENTS

This work was supported by the Ministry of Education and Science of Russia, agreement no 14.604.21.0181 of 26 Sep 2017 (unique project identifier RFMEFI60417X0181).

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Authors and Affiliations

  1. Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences, 119991, Moscow, Russia

    S. V. Shorunov, E. S. Piskunova, V. A. Petrov, V. I. Bykov & M. V. Bermeshev

  2. Mendeleev University of Chemical Technology, Moscow, Russia

    E. S. Piskunova & M. V. Bermeshev

Authors
  1. S. V. Shorunov
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  2. E. S. Piskunova
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  3. V. A. Petrov
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  4. V. I. Bykov
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  5. M. V. Bermeshev
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Corresponding author

Correspondence to M. V. Bermeshev.

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Translated by S. Zatonsky

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Shorunov, S.V., Piskunova, E.S., Petrov, V.A. et al. Selective Hydrogenation of 5-Vinyl-2-Norbornene to 2-Vinylnorbornane. Pet. Chem. 58, 1056–1063 (2018). https://doi.org/10.1134/S0965544118120125

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  • DOI: https://doi.org/10.1134/S0965544118120125

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