GB927048A - Process for the epoxidation of compounds with olefinic double bonds - Google Patents

Abstract

Epoxy compounds are made by the epoxidation of an organic compound containing at least one aliphatic or cycloaliphatic double bond, not more than 30 carbon atoms per double bond, and which boils at not less than 50 DEG C. at atmospheric pressure with an epoxidizing agent which is a mixture of a mono-, oligo or polysaccharide or a polyalcohol or mixture thereof and hydrogen peroxide in the presence of an acid activator and distilling off reaction water during the reaction at temperatures below 100C. In a further embodiment, the epoxidation is effected with a percarboxylic acid in the presence of a water soluble inorganic or organic acid or halide as activator, distilling off during the reaction the reaction water at temperatures below 100 DEG C. and maintaining the concentration of the activator within the reaction mixture by neutralisation during the reaction water distillation. Similar acid activators may be used in the first embodiment, examples being sulphuric, nitric, phosphoric, and perchloric acids, boron trifluoride-water adducts, acid phosphoric acid esters, sulphonic acids, and organic baseexchangers. To neutralise the acids in both of the above embodiments, oxides, hydroxides, carbonates and bicarbonates of sodium, potassium, ammonium or the alkaline earth metals, or an anion-exchange compounds, may be used. According to a further embodiment, the epoxidation may be effected using a percarboxylic acid in the presence of an aluminium compound prepared by dehydration of aluminium hydroxide, of composition and/or crystal structure lying in the range Al2O3 .2H2O to g -Al2O3, and distilling off reaction water during the reaction at temperatures below 100 DEG C. In the last two embodiments the percarboxylic acid may be formed in situ from a mono- or polycarboxylic acid and hydrogen peroxide. Examples of suitable carboxylic acids are given. The removal of water in all embodiments may take place at reduced pressure, preferably with the aid of an inert organic solvent as entrainer such as an aliphatic, cycloaliphatic or aromatic hydrocarbon, a halogenated hydrocarbon, an ether or ester. A wide variety of olefinic compounds is specified including straight-chain or branched-chain olefines, unsaturated alcohols, aldehydes, ethers, esters, and carboxylic acids, unsaturated natural products and polymers. Detailed examples describe the epoxidation of soya bean oil, oleic acid, diallyl terephthalate, and a C11-olefine-paraffin mixture. Specifications 864,300 and 865,271 are referred to. Reference has been directed by the Comptroller to Specification 868,890.