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).
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).
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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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
- Binary Mixture