Abstract
Hydrogenation of cyclohexene has been studied under pressure in a flow reactor on the following catalysts: Na- and H-forms of Y-type zeolites, erionite, magnesium and lanthanum oxides, palladium on silica and aluminum oxide. This reaction is accompanied by skeletal isomerization to give methylcyclopentane and methylcyclopentenes. The differences in activation energies for isomerization and hydrogenation reactions were estimated as 83–96 kJ/mole for NaY and Na,K-erionite, 33–50 kJ/mole for the H-forms of the zeolites, 33–37 kJ/mole on the Pd catalysts, and 25–33 kJ/mole on magnesium and lanthanum oxides. It is suggested that the cyclohexyl complex, formed as an intermediate during hydrogenation of cyclohexene on Na-forms of the zeolites, is neither a carbocation nor a radical.
Similar content being viewed by others
Literature cited
Kh. M. Minachev, V. I. Garanin, V. V. Kharlamov, T. A. Isakova, and É. É. Senderov,Izv. Akad. Nauk SSSR, Ser. Khim., No. 8, 1737 (1969).
V. V. Kharlamov, V. I. Garanin, D. B. Tagiev, and Kh. M. Minachev, in: All-Union Conf. on the Mechanism of Heterogeneous Catalytic Reactions [in Russian], Preprint No. 41, Moscow (1974).
Kh. M. Minachev, V. V. Kharlamov, and N. G. Kharatishvili,Izv. Akad. Nauk SSSR, Ser. Khim., No. 1, 97 (1979).
V. V. Kharlamov, N. G. Kharatishvili, and Kh. M. Minachev,Izv. Akad. Nauk SSSR, Ser. Khim., No. 10, 2396 (1981).
Kh. M. Minachev, V. I. Garanin, V. V. Kharlamov, and M. A. Kapustin,Izv. Akad. Nauk SSSR, Ser. Khim., No. 12, 2673 (1975).
R. A. Karakhanov, V. I. Garanin, V. V. Kharlamov, M. A. Kapustin, B. B. Blinov, and Kh. M. Minachev,Izv. Akad. Nauk SSSR, Ser. Khim., No. 2, 445 (1975).
K. V. Topchieva, O. L. Shakhnovskaya, and E. N. Rosolovskaya,Kinet. Katal.,10, No. 6, 1381 (1969).
Z. V. Gryaznova, G. V. Tsitsishvili, and N. N. Naskidashvili,React. Kinet. Catal. Lett.,7, No. 1, 59 (1977).
F. A. Chernyshkova, D. V. Mushenko, and L. A. Blandina,Neftekhimiya,14, No. 2, 188 (1974).
T. Sano, K. Okabe, H. Shoji, K. Saite, Y. Yasumoto, H. Hagiwara, and H. Takaya,Bull. Chem. Soc. Jpn.,58, No. 11, 3371 (1985).
T. Sano, H. Hagiwara, K. Okabe, H. Okado, K. Saito, and H. Takaya,Sekiyu Gakkai Shi,29, No. 1, 89 (1986).
T. Sano, H. Shoji, K. Okabe, K. Matsuzaki, H. Hagiwara, and H. Takaya, in: 7th Intern. Zeolite Conf., Tokyo (1986), p. 233.
T. Sano, K. Okabe, H. Hagiwara, H. Takaya, H. Shoji, and K. Matsuzaki,J. Mol. Catal.,40, No. 1, 113 (1987).
N. Y. Chen and W. E. Garwood,J. Catal.,50, 252 (1977).
Kh. M. Minachev, V. V. Kharlamov, V. I. Garanin, and D. B. Tagiev,Izv. Akad. Nauk SSSR, Ser. Khim., No. 11, 2410 (1975).
V. V. Kharlamov, V. I. Garanin, D. B. Tagiev, and Kh. M. Minachev,Izv. Akad. Nauk SSSR, Ser. Khim., No. 11, 2406 (1975).
V. V. Kharlamov, N. G. Kharatishvili, Yu. A. Borisov, P. I. Slyunyaev, and Kh. M. Minachev,Izv. Akad. Nauk SSSR, Ser. Khim., No. 7, 1497 (1980).
N.D. Chuvylkin and G. M. Zhidomirov,Kinet. Katal.,18, 903 (1977).
Kh. M. Minachev, V. V. Kharlamov, and V. I. Garanin,Catalysis on Zeolites, D. Kallo and Kh. M. Minachev (eds.), Akademiai Kiado, Budapest (1988), p. 490.
H. Hattori, Y. Tanaka, and K. Tanabe,J. Am. Chem. Soc.,98, No. 15, 4652 (1976).
K. Tanaka and T. Okuhara,J. Catal.,65, 1 (1980).
K. I. Tanaka, K. Aomura, T. Okuhara, and K. Miyahara,J. Chem. Soc. Faraday Trans. I,77, No. 7, 1697 (1981).
F. Weygand and G. Hilgetag (eds.),Experimental Methods in Organic Chemistry, 3rd edn. [in German], Barth, Leipzig (1964).
A. A. Potekhin (ed.),Properties of Organic Compounds [in Russian], Khimiya, Leningrad (1984), p. 422.
N. E. Zlotina and S. L. Kiperman,Kinet. Katal.,8, No. 2, 393 (1967).
H. Kubicka,J. Catal.,12, 223 (1968).
P. Z. C. Van Meerten and J. W. F. Coenen,J. Catal.,37, No. 1, 37 (1975).
H. Kubicka,Rhenium, Technetium, and Platinum Metals as Catalysts for Reactions Involving Hydrogen, Zaklad Narodowy Imienia Ossolinskich Polskiij Akademii Nauk, Wroclaw—Warszawa—Krakow—Gdansk (1978), p. 24.
M. Tezuka, Y. Inoue, and I. Yasumori,Bull. Chem. Soc. Jpn.,54, No. 8, 2515 (1981).
Kh. M. Minachev, V. V. Kharlamov, V. I. Garanin, and D. B. Tagiev,Izv. Akad. Nauk SSSR, Ser. Khim., No. 8, 1709 (1976).
V. V. Kharlamov, T. S. Starostina, and Kh. M. Minachev,Izv. Akad. Nauk SSSR, Ser. Khim., No. 10, 2291 (1982).
Chemical Bond Energies. Ionization Potentials and Electron Affinities. Reference Book [in Russian], Izd. Akad. Nauk SSSR, Moscow (1962).
Additional information
Deceased.
N. D. Zelinskii Institute of Organic Chemistry, Russian Academy of Sciences, Moscow 117913. Translated from Izvestiya Akademii Nauk, Seriya Khimicheskaya, No. 4, pp. 791–799, April, 1992.
Rights and permissions
About this article
Cite this article
Kharlamov, V.V., Garanin, V.I., Karakhotin, S.N. et al. Hydrogenation of cyclohexene on different types of catalysts. Russ Chem Bull 41, 612–618 (1992). https://doi.org/10.1007/BF01150879
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF01150879