GB654764A - Hydroxylation of olefinic compounds - Google Patents

Abstract

Compounds having at least two hydroxyl groups attached to two adjacent carbon atoms are manufactured by the hydroxylation of compounds with one olefinic link with aqueous hydrogen peroxide in the presence of a catalyst, initially in the form of tungsten oxide and/or molybdenum oxide, at a temperature between 50 DEG and 100 DEG C. The reaction may be carried out with or without the presence of an inert organic water-miscible diluent, e.g. acetone, tertiary butanol, dioxane or acetic acid. Olefinic compounds which may be used as starting materials are hydrocarbons such as n-oct-1-ene cyclohexene, but-1-ene, 2 : 4 : 4-trimethyl-pent-1-ene, 2 : 4 : 4-trimethyl-pent-2-ene and 4-ethyl-pent-2-ene; alcohols such as allyl alcohol, crotyl alcohol, but-3-en-2-ol, pent-3-en-2-ol and 4-methyl-pent-4-en-2-ol and olefinic acids such as acrylic acid, crotonic acid and maleic acid. Olefinic aldehydes such as acrolein and crotonaldehyde may also be hydroxylated in this way but they may be oxidized simultaneously to the corresponding acids. When acetic acid is used as a diluent it is desirable to react it first with the hydrogen peroxide, dissolve the tungstic and/or molybdic oxide therein and then react the mixture with the olefinic compound. In the examples: (a) glycerol is prepared from allyl alcohol; (b) butane-1,2,3-triol is prepared from crotyl alcohol; (c) 1.2-dihydroxybutyric acid is prepared from crotonic acid; (d) octane-1.2-diol is prepared from n-oct-1-ene; (e) trans-cyclohexane-1.2-diol is prepared from 3-ethyl-pent-2-ene by the action of aqueous hydrogen peroxide in the presence of a catalyst as described above. Specification 508,526 is referred to.