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Regularities of the heterogeneous catalytic hydrogenation of 5-vinyl-2-norbornene

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Abstract

The liquid-phase hydrogenation of 5-ethenylbicyclo[2.2.1]hept-2-ene (5-vinyl-2-norbornene, VNE) in the presence of the palladium catalyst Pd/γ-Al2O3 (PC-25) in an n-heptane medium at 76 °C was studied. The hydrogenation proceeds via a complicated mechanism through (exo/endo)-2-vinylnorbornanes and (Z/E)-2-ethylidenenorbornanes to form (exo/endo)-2-ethylnorbornanes. The reaction products were identified, the main reaction routes were determined, and the material balance was studied. The isomerization of (exo/endo)-2-vinylnorbornanes to (Z/E)-2-ethylidenenorbornanes with the conversion close to 100% was found for the reaction in a hydrogen atmosphere. The molar ratios of the stereoisomers of the substrate and of the intermediate and final hydrogenation products are retained at all steps of the process. The parallel-sequential mechanism was proposed for the process. The zero kinetic time order with respect to VNE was established in a wide range of its initial concentrations.

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Authors and Affiliations

  1. MIREA - Russian Technological University, 86 prosp. Vernadskogo, 119571, Moscow, Russia

    V. V. Zamalyutin, A. V. Ryabov, A. I. Nichugovskii, A. Yu. Skryabina, O. Yu. Tkachenko & V. R. Flid

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  1. V. V. Zamalyutin
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  2. A. V. Ryabov
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  3. A. I. Nichugovskii
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  4. A. Yu. Skryabina
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  5. O. Yu. Tkachenko
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  6. V. R. Flid
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Corresponding authors

Correspondence to V. V. Zamalyutin or V. R. Flid.

Additional information

Dedicated to Academician of the Russian Academy of Sciences O. M. Nefedov on the occasion of his 90th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 70–75, January, 2022.

This work was performed using equipment of the Center for Collective Use of the Russian Technological University and financially supported by the Ministry of Science and Higher Education of the Russian Federation.

No human or animal subjects were used in this research.

The authors declare no competing interests.

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Zamalyutin, V.V., Ryabov, A.V., Nichugovskii, A.I. et al. Regularities of the heterogeneous catalytic hydrogenation of 5-vinyl-2-norbornene. Russ Chem Bull 71, 70–75 (2022). https://doi.org/10.1007/s11172-022-3378-5

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  • DOI: https://doi.org/10.1007/s11172-022-3378-5

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