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Mechanism of the hydrogenation of acetylenic hydrocarbons over raney nickel

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Summary

  1. 1.

    A study was made of the mechanism of the addition of hydrogen at a triple bond by the method of hydrogenating binary mixtures of acetylenic and ethylenic hydrocarbons (C5 and C6).

  2. 2.

    β-Acetylenic hydrocarbons are hydrogenated largely selectively and stereospecifically; the process proceeds in the main through the stage of the formation of the cis olefin. The saturated hydrocarbon and products of cis-trans isomerization and of double-bond migration are formed in the first stage of the hydrogenation only in small amounts and only by the scheme (2).

  3. 3.

    In the first stage of the process anα-acetylenic hydrocarbon is partially hydrogenated to the saturated hydrocarbon, whereas theα-olefin component of the mixture is hydrogenated to a very small extent and is not isomerized. Anα-acetylenic hydrocarbon is therefore hydrogenated by two mechanisms simultaneously: with intermediate formation of the olefin and without formation of an olefin that desorbs into the bulk phase.

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Literature cited

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    L. Kh. Freidlin and Yu. Yu. Kaup, Izv. AN SSSR, Otd. khim. n.1962, 1660.

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    L. Kh. Freidlin, Yu. Yu. Kaup, E. F. Litvin and T. I. Ilomets, Dokl. AN SSSR143, 883 (1962).

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    L. Kh. Freidlin, Yu. Yu. Kaup and E. F. Litvin, Izv. AN SSSR. Otd. khim. n.1962, 1464.

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    G. Egloff. Physical Constants of Hydrocarbons1, 185, 343, 264 (1939).

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Freidlin, L.K., Kaup, Y.Y. Mechanism of the hydrogenation of acetylenic hydrocarbons over raney nickel. Russ Chem Bull 12, 147–150 (1963). https://doi.org/10.1007/BF00846966

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Keywords

  • Hydrogenation
  • Nickel
  • Migration
  • Hydrocarbon
  • Binary Mixture