Abstract
Piperylene mixed with air is converted into a mixture of aromatics containing azulene and naphthalene on contact with bisnuith oxide at -600 °C. The yield of azulene and naphthalene is 6–8 %, The reaction is accompanied by burning of some of the piperylene and by the reduction of Bi2O3 to Bi metal. When the initial mixture is diluted with steam no reduction occurs. The reaction is believed to involve elimination of the allylic hydrogen, formation of dienyl radicals, their dimerization, and subsequent aromatization.
References
K. M. Gitis and M. I. Rozengart,Izv. Akad. Nauk SSSR, Ser. Khim., 1975, 1685 [Bull. Acad. Sci USSR, Div. Chem. Sci., 1975,24 (Engl. Transl.)].
H. E. Swift, I. E. Bosik, and I. A. Ondrey,J. Catal., 1971,21, 212.
K. Ohdan, T. Ogawa, S. Umemura, and K. Jamada,J. Chem. Soc. Jpn, Jnd. Chem. Soc., 1970,73, 842.
T. Sciyama, M. Egishira, T. Sakamoto, and F. A. Rusala,J. Catal., 1972,24, 76.
E. A. Mamedov, G. B. Keulke, and F. A. Rusala,J. Catal., 1981,70, 241.
F. E. Massoth and D. A. Scarpiello,J. Catal., 1971,21, 225.
J. Kaber and B. Orzibowska,J. Catal., 1973,28. 489.
T. Seiyama, T. Uda, and M. Egasbira,J. Catal., 1974,34, 29.
L. M. Kaliberdo, M. L. Tselyutina, A. S. Vaabel', V. M. Kalikman, and V. N. Shvetsov,Zh. Fiz. Khim., 1979,53, 1495 [Russ. J. Phys. Chem., 1979,53 (Engl. Transl.)].
E. G. Galid-Zade, E. A. Mamedov, and R. G. Rizaev,Kinet. Katal., 1979,20, 405 [Kinet. Catal., 1979,20 (Engl. Transl.)]
T. Tomas,Promyshlennye kataliticheskie protsessy i effek-tivnye katalizatory [Industrial Catalytic Processes and Efficient Catalysts], Mir, Moscow, 1973 (Russ. Transl.).
Yu. V. Karyakin and I. I. Angelov,Chistye khimicheskie veshchestva [Pure Chemical Compounds], Khimiya, Moscow, 1974, 181, 296 (in Russian).
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Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 6, pp. 1556–1558, June, 1996.
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Gitis, K.M., Isagulyants, G.V. Formation of azulene and naphthalene from piperylene. Russ Chem Bull 45, 1484–1487 (1996). https://doi.org/10.1007/BF01434239
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DOI: https://doi.org/10.1007/BF01434239