Summary
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1.
A study was made of the character (stagewise or simultaneous) of the hydrogenation of the double bonds of 1,3-cyclohexadiene and its irreversible catalysis over platinum and palladium blacks.
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2.
In presence of platinum or palladium black in alcohol or in heptane at 25° the double bonds of 1,3-cyclohexadiene are hydrogenated successively. The whole of the 1,3-cyclohexadiene is first converted into cyclohexene, and then this product begins to take up hydrogen with formation of cyclohexane.
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3.
The hydrogenation of 1,3-cyclohexadiene is accompanied by a hydrogen-redistribution reaction with formation of cyclohexene and benzene.
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4.
The relative rates of the hydrogenation and irreversible-catalysis reaction depend on the nature of the catalyst. In presence of platinum black hydrogenation predominates, and in presence of palladium black irreversible catalysis predominates.
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Freidlin, L.K., Polkovnikov, B.D. & Egorov, Y.P. Consecutive hydrogenation of the double bonds of 1,3-cyclohexadiene and its irreversible catalysis on platinum and palladium blacks. Russ Chem Bull 8, 876–881 (1959). https://doi.org/10.1007/BF00915919
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DOI: https://doi.org/10.1007/BF00915919