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
Langmuir, I., J. Am. Chem. Soc., 1918, vol. 40, p. 1361.
Masel, R., Principles of Adsorption and Reaction on Solid Surfaces, New York: Wiley, 1996.
Nishimura, S., Handbook of Heterogeneous Catalytic Hydrogenation for Organic Synthesis, New York: Wiley, 2001.
Berenblyum, A.S., Danyushevsky, V.Ya., and Katsman, E.A., Kinet. Catal., 2019, vol. 60, no. 4, p. 381.
Berenblyum, A.S., Al-Wadhaf, H.A., Katsman, E.A., and Flid, V.R., Kinet. Catal., 2011, vol. 52, no. 2, p. 296.
Tagandurdyyeva, N., Maltseva, N.V., Vishnevskaya, T.A., et al., Fine Chem. Technol., 2020, vol. 15, p. 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.
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
Moiseev, I.I. and Vargaftik, M.N., Catalysis by Di- and Polynuclear Metal Complexes, New York: Wiley, 1998, no. 4, p. 395.
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.
Shamsiev, R.S., Danilov, F.O., and Morozova, T.A., Russ. Chem. Bull., 2017, vol. 66, no. 3, p. 401.
Shamsiev, R.S., Danilov, F.O., Flid, V.R., and Shmidt, E.Yu., Russ. Chem. Bull., 2017, vol. 66, no. 12, p. 2234.
Berenblyum, A.S., Al’-Vadkhav, Kh.A., and Katsman, E.A., Neftekhimiya, 2015, vol. 55, no. 2, p. 125.
Berenblyum, A.S., Podoplelova, T.A., Katsman, E.A., et al., Kinet. Catal., 2012, vol. 53, no. 5, p. 595.
Katsman, E.A., Danyushevsky, V.Ya., Kuznetsov, P.S., et al., Kinet. Catal., 2017, vol. 58, no. 2, p. 147.
Katsman, E.A., Danyushevsky, V.Ya., and Kuznetsov, P.S., Petroleum Chemistry, 2017, vol. 57, no. 12, p. 1190.
Basimova, R.A., Pavlov, M.L., and Myachin, S.I., Neftekhimiya, 2009, vol. 5, no. 5, p. 360.
Nazarov, M.V., Laskin, A.I., Il’yasov, I.R., et al., Kataliz v Promyshlennosti, 2013, no. 2, p. 39.
Stytsenko, V.D. and Mel’nikov, D.P., Russ. J. Phys. Chem., 2016, vol. 90, no. 5, p. 932.
Flid, V.R., Gringolts, M.L., Shamsiev, R.S., and Finkelshtein, E.Sh., Russ. Chem. Rev., 2018, vol. 87, p. 1169.
Shorunov, S.V., Zarezin, D.P., Samoilov, V.O., et al., Fuel, 2021, vol. 283, p. 118935.
Catalogue. Redkino Catalyst Company. http:// www.recatalys.ru/katalog/.
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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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