Photochemical method of producing cycloalkanoneoxime hydrochlorides

In the manufacture of cycloalkanone oxime hydrochlorides by reacting a cycloalkane with nitrosyl chloride in the presence of hydrogen chloride and under actinic radiation, the nitrosyl chloride is used in admixture with chlorine, the molar ratio of nitrosyl chloride to chlorine being from 1:1 to 200:1. The hydrogen chloride may be included in the gas mixture or it may be added to the cycloalkane before the gas mixture is introduced. The gas mixture may contain an inert gas, e.g. hydrogen, nitrogen or carbon dioxide, and the cycloalkane may be mixed with an inert diluent, e.g. benzene or carbon tetrachloride. The reaction is preferably effected under the conditions described in Specification 922,364. Examples are given of the manufacture of oxime hydrochlorides from cyclohexane and cyclooctane. The treatment of cycloheptane is also mentioned.