Hydrogenolysis of symmetrical α, α' - dioxyacetylene

Abstract

Catalytic hydrogenation of 2-butyne-1, 4-diol (I) ,3-hexyne-2, 5-diol (II) and 2, 5-dimethy1-3-hexyne-2, 5-diol (III) was carried out as a mixed methanolic solution under ordinary pressure and temperature with Pd-CaCO3 Catalyst. II which has two hydroxyl groups of secondary was most easily hydrogenolized and gave 2-hexanol in a 26mol% yield. 1-Butanol in a 16% resulted from I which has primary hydroxyl groups. A corresponding monohydric alcohol did not result from III which has tertiary hydroxyl groups, but by the hydrogenation of only III 2, 5-dimethy1-2-hexanol was obtained in a 4% yield.