GB921554A - Process for the production of halogenourethanes - Google Patents

Abstract

Some low molecular weight polyiminocarbonate hydrohalide chains of low molecular weight are formed when aromatic alcohols containing at least two aliphatic hydroxy groups, or aliphatic compounds containing at least two hydroxy groups separated by more than three carbon atoms, such as butane-1,4-diol, hexane-1,6-diol, diethylene glycol and p-xylylene glycol, are reacted at normal pressure with a cyanogen halide in the presence of hydrogen halide or aluminium chloride. An example is the reaction of butane-1,4-diol with cyanogen chloride: <FORM:0921554/IV(a)/1> Resinous materials are obtained in examples which react cyanogen chloride with butane-1,4-diol and with diethylene glycol.ALSO:Halogenourethanes are prepared by reacting aliphatic or aromatic alcohols containing at least two aliphatic hydroxyl groups with a cyanogen halide at normal pressure in the presence of hydrogen halide or aluminium chloride. The products contain halogen and -OCONH2 in place of two initial hydroxy groups. The cyanogen halide is preferably used in excess. Solvents or dispersing agents may be used, such as ether, benzene, dioxan and carbon tetrachloride; aqueous hydrohalic acid may be used as solvent and catalyst. Examples use as starting materials ethylene glycol, 1,3- and 1,4-butylene glycol and diethylene glycol; other starting materials referred to are 1,6-hexylene glycol and p-xylylene glycol.