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Change in the selectivity of the action of catalysts in the hydrogenation of the dienone group

Communication 7. Modification of nickel catalysts with lead

Conclusions

  1. 1.

    The addition of metallic lead and treatment with a solution of lead acetate changed the selectivity of the acticn of Ni-Al2O3 and Ni-ZnO catalysts in the hydrogenation of dienones. In the presence of a modified catalyst, hydrogen is preferentially added at the 3,4-double bond, while on an unmodified catalyst it is preferentially added at the 5,6-double bond.

  2. 2.

    Intermediate enol formation (registered by deutero-exchange) shows that the change in the direction of the process is associated with a change in its mechanism. On the modified catalyst, 1,2-addition of hydrogen is reduced, and the 3,4-bond is saturated to a substantial degree by 1,4-addition of hydrogen to the C=C C=O group.

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Literature cited

  1. 1.

    L. Kh. Freidlin, N. V. Borunova, and L. I. Gvinter, Dokl. Akad. Nauk SSSR,163, 1173 (1965).

  2. 2.

    L. Kh. Freidlin, N. V. Borunova, L. I. Gvinter, and S. S. Daniélova, Zh. Fiz, Khimii,37, 98 (1968).

  3. 3.

    L. Kh. Freidlin, N. V. Borunova, G. I. Samokhvalov, M. A. Miropol'skaya, M. Ts. Yanotovskii, L. I. Gvinter, and N. I. Fedotova, Izv. Akad. Nauk SSSR, Ser. Khim., 996 (1964).

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    L. Kh. Freidlin, N. V. Borunova, I. E. Neimark, and L. I. Gvinter, Izv. Akad. Nauk SSSR, Ser. Khim., 1328 (1966).

  5. 5.

    L. Kh. Freidlin, L. I. Gvinter, N. V. Borunova, S. F. Dymova, and I. M. Kustanovich, Izv. Akad. Nauk SSSR, Ser. Khim., 1052 (1972).

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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 6, pp. 1299–1304, June, 1972.

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Borunova, N.V., Freidlin, L.K., Gvinter, L.I. et al. Change in the selectivity of the action of catalysts in the hydrogenation of the dienone group. Russ Chem Bull 21, 1254–1257 (1972). https://doi.org/10.1007/BF00854539

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Keywords

  • Hydrogen
  • Acetate
  • Enol
  • Lead Acetate
  • Enol Formation