Patent GB-1023423-A (GB)
Title: Production of adducts of carbon tetrachloride and alkenes
IPC: C07C17/278
Filed: 1962-09-11
Abstract: Adducts of carbon tetrachloride and natural or synthetic rubber containing internal unsaturation, together wirh the alcoholysis product thereof, which adducts contain up to one molecule of carbon tetrachloride for each double-bond bound in the form of one chlorine atom and one trichloromethyl group, are made by a process comprising reacting carbon tetrachloride with the rubber at an elevated temperature in the presence of a chloride of copper or iron as catalyst, if desired, in the presence of a co-solvent for the catalyst and the other components of the reaction mixture, the use of an alcohol as co-solvent allowing an alcoholysis product to be formed by the replacement of the added chlorine atom with the alkoxy group of the alcohol used, and recovering the reaction product from the reaction mixture.  It is preferred to carry out the reaction in the presence of an amine hydrochloride and/or in the presence of, as a reducing agent, of one or more of the compounds: benzoin, hydroquinone, stannous chloride, alkali metal sulfites and aldehydes.ALSO:Adducts of carbon tetrachloride and hydrocarbon compounds having at least one isolated non-aromatic double bond, or at least one pair of conjugated non-aromatic double bonds, which hydrocarbons may be substituted by alkyl, aryl, aralkyl, carboxyl, carbamido, carboxyalkyl, nitrile, hydroxymethyl, acyloxymethyl, halogen or acyloxy radicals, and which may be a natural or synthetic rubber containing internal unsaturation, together with the alcoholysis product thereof, which adducts contain up to one molecule of carbon tetrachloride for each isolated double bond or pair of conjugated double bonds, bound in the form of one chlorine atom and one trichloromethyl group, are made by a process comprising reacting carbon tetrachloride with said hydrocarbon compound at an elevated temperature in the presence of a chloride of copper or iron as catalyst, if desired in the presence of a co-solvent for the catalyst and the other components of the reaction mixture, the use of an alcohol as co-solvent allowing an alcoholysis product to be formed if desired, by the replacement of the added chlorine atom with the alkoxy group of the alcohol used, and recovering the reaction product from the reaction mixture.  It is preferred to carry out the reaction in the presence of an amine hydrochloride and/or in the presence of, as a reducing agent, of one or more of the compounds: benzoin, hydroquinone, stannous chloride, alkali metal sulphites and aldehydes.  The invention also comprises the products of the above reaction.  In the examples the synthesis of the following products are described: 1-1-1-3-tetrachloro - 3 - phenyl propane, 1 - 1 - 1 - 5 - tetrachloropentane - 3, 1 - 1 - 1 - 3 - tetrachlorononane, the carbon tetrachloride adduct of rubber latex, 1-1-1-3-tetrachloro propane, 1-1-1-5 - tetrachloro - n - pentane, 1 - 1 - 1 - 7 - tetrachloro-n-heptane. In further examples are described the reaction of carbon tetrachloride with styrene, acrylonitrile, methyl acrylate, allyl alcohol, ethylene, butene-1, cis-butene-2, and 1-octene, which products include alcoholysis products as well as straight carbon tetrachloride adducts.