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Specific Features of the Catalytic Hydrogenation of the Norbornadiene-Based Carbocyclic Compounds

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Abstract

The gas- and liquid-phase hydrogenation of bicyclo[2.2.1]hepta-2,5-diene (norbornadiene) in the presence of the Pd/γ-Al2O3 (PK-25) industrial palladium catalyst in an n-heptane medium at 75–200°С is studied. The reaction products are identified, the main reaction routes are established, and the material balance is studied. The effect of preferable adsorption of norbornadiene compared to other components of the system on the palladium active site is confirmed. A relationship between possible modes of norbornadiene coordination and the product structure is considered. A parallel-sequential scheme is proposed for the mechanism of the process on the basis of the obtained experimental and theoretical data.

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REFERENCES

  1. Langmuir, I., J. Am. Chem. Soc., 1918, vol. 40, p. 1361.

    Article  CAS  Google Scholar 

  2. Masel, R., Principles of Adsorption and Reaction on Solid Surfaces, New York: Wiley, 1996.

    Google Scholar 

  3. Nishimura, S., Handbook of Heterogeneous Catalytic Hydrogenation for Organic Synthesis, New York: Wiley, 2001.

    Google Scholar 

  4. Berenblyum, A.S., Danyushevsky, V.Ya., and Katsman, E.A., Kinet. Catal., 2019, vol. 60, no. 4, p. 381.

    Article  CAS  Google Scholar 

  5. Berenblyum, A.S., Al-Wadhaf, H.A., Katsman, E.A., and Flid, V.R., Kinet. Catal., 2011, vol. 52, no. 2, p. 296.

    Article  CAS  Google Scholar 

  6. Tagandurdyyeva, N., Maltseva, N.V., Vishnevskaya, T.A., et al., Fine Chem. Technol., 2020, vol. 15, p. 7.

    Article  Google Scholar 

  7. Katsman, E.A., Danyushevskii, V.Ya., Shamsiev, R.S., and Flid, V.R., Teoriya i praktika geterogennykh katalizatorov i adsorbentov (Theory and Practice of Heterogeneous Catalysts and Adsorbents), Koifman, O.I., Ed., Moscow: URSS, 2020.

    Google Scholar 

  8. Moiseev, I.I. and Vargaftik, M.N., Catalysis with giant palladium clusters, in Perspectives in Catalysis, Thomas, J.M. and Zamaraev, K.I., Eds., Oxford: Blackwell, 1991, p. 91

    Google Scholar 

  9. Moiseev, I.I. and Vargaftik, M.N., Catalysis by Di- and Polynuclear Metal Complexes, New York: Wiley, 1998, no. 4, p. 395.

  10. Moiseev, I.I., Gekhman, A.E., Tsodikov, M.V., et al., in Multimetallic Catalyst in Organic Synthesis, Shibasaki, M.,  and Yamamoto, Y, Eds., Weinheim: Wiley-VHS, 2004, p. 249.

    Google Scholar 

  11. Shamsiev, R.S., Danilov, F.O., and Morozova, T.A., Russ. Chem. Bull., 2017, vol. 66, no. 3, p. 401.

    Article  CAS  Google Scholar 

  12. Shamsiev, R.S., Danilov, F.O., Flid, V.R., and Shmidt, E.Yu., Russ. Chem. Bull., 2017, vol. 66, no. 12, p. 2234.

    Article  CAS  Google Scholar 

  13. Berenblyum, A.S., Al’-Vadkhav, Kh.A., and Katsman, E.A., Neftekhimiya, 2015, vol. 55, no. 2, p. 125.

    Article  Google Scholar 

  14. Berenblyum, A.S., Podoplelova, T.A., Katsman, E.A., et al., Kinet. Catal., 2012, vol. 53, no. 5, p. 595.

    Article  CAS  Google Scholar 

  15. Katsman, E.A., Danyushevsky, V.Ya., Kuznetsov, P.S., et al., Kinet. Catal., 2017, vol. 58, no. 2, p. 147.

    Article  CAS  Google Scholar 

  16. Katsman, E.A., Danyushevsky, V.Ya., and Kuznetsov, P.S., Petroleum Chemistry, 2017, vol. 57, no. 12, p. 1190.

    Article  CAS  Google Scholar 

  17. Basimova, R.A., Pavlov, M.L., and Myachin, S.I., Neftekhimiya, 2009, vol. 5, no. 5, p. 360.

    Google Scholar 

  18. Nazarov, M.V., Laskin, A.I., Il’yasov, I.R., et al., Kataliz v Promyshlennosti, 2013, no. 2, p. 39.

  19. Stytsenko, V.D. and Mel’nikov, D.P., Russ. J. Phys. Chem., 2016, vol. 90, no. 5, p. 932.

    Article  CAS  Google Scholar 

  20. Flid, V.R., Gringolts, M.L., Shamsiev, R.S., and Finkelshtein, E.Sh., Russ. Chem. Rev., 2018, vol. 87, p. 1169.

    Article  CAS  Google Scholar 

  21. Shorunov, S.V., Zarezin, D.P., Samoilov, V.O., et al., Fuel, 2021, vol. 283, p. 118935.

    Article  CAS  Google Scholar 

  22. Catalogue. Redkino Catalyst Company. http:// www.recatalys.ru/katalog/.

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ACKNOWLEDGMENTS

This work was carried out using equipment of the Center for Collective Use of the Russian Technological University MIREA supported by the Ministry of Education and Science of the Russian Federation.

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

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Dedicated to blessed memory of outstanding scientist Il’ya Iosifovich Moiseev

Translated by E. Yablonskaya

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Zamalyutin, V.V., Katsman, E.A., Danyushevsky, V.Y. et al. Specific Features of the Catalytic Hydrogenation of the Norbornadiene-Based Carbocyclic Compounds. Russ J Coord Chem 47, 695–701 (2021). https://doi.org/10.1134/S1070328421100080

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  • DOI: https://doi.org/10.1134/S1070328421100080

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