GB1352441A - Oxidation of vicinal diol groups - Google Patents

Abstract

1352441 Oxidation of vicinal diols DEUTSCHE GOLDUND SILBER-SCHEIDEANSTALT 14 July 1971 [17 July 1970] 33043/71 Heading C2C Carboxylic, dicarboxylic, polycarboxylic or partly esterified carboxylic acids are prepared by the oxidation of vicinal diol groups to carboxyl groups with a percarboxylic acid in the presence of an organic solvent and ions or ion mixtures of iron, nickel, palladium, cobalt or manganese. The diols may be 1,2-octane diol, 1,2-decane diol, 1,2-dodecanediol, 1,2-octadecane diol, 1,2-cyclooctane diol, 1,2-cyclododecane diol, 7,8-tetradecane diol, α-monoalkyl glycerine ethers, 1,2-dihydroxytetralin, hydrindendiol, camphorglycol, 9,10-dihydroxystearic acid and esters and 9,10-dihydroxyoctadecanol, and solvents may be acetic acid, esters and benzene. Peracetic, perproprionic, perbutyric, and perbenzoic acids may be used with salts of the metals, preferably, acetates such as lead (II) or lead (IV). Examples describe the oxidation of 1,2-dodecane diol with peracetic acid in the presence of Co, Mn (II), Ni (II), Fe (III), Pd (II), Pb (II) and Co (II) acetates to undecanoic acid; 7,8-tetradecane diol with peracetic acid and a Co (II) acetate catalyst to oenanthic acid; 1,2-cyclohexane diol with peracetic acid and Pb (II) and Co acetate catalyst to adipic acid; 9,10-dihydroxy stearic acid with peracetic acid and Co (II) acetate to azelaic and pelargonic acids; and a hydroxylated mixture of oleic and stearic acid with peracetic acid and Co acetate to a mixture of azelaic and pelargonic acids.