Patent GB-652768-A (GB)
Title: Improvements in coupling of non-aromatic compounds
IPC: C07C17/26
Filed: 1948-04-16
Abstract: Linear polymers are obtained from bodies containing more than one trihalomethyl radical, e.g. 1,6-bis-(trichlormethyl)-2,5-dibromohexane, by hydrogenating in presence of a hydrogen halide acceptor.ALSO:A mixture of compounds R-CX3 and R1-CX3, where X is chlorine or bromine and R and R1 are similar or dissimilar non-aromatic and non-heterocyclic groups, each p  containing at least two carbon atoms, is subjected to the action of hydrogen in presence of a hydrogenation catalyst and a hydrogen halide acceptor to eliminate at least two molecular proportions of hydrogen halide and give a compound of the formula R.CX2.CX2.R1, which with more hydrogen will give R.CHX.CHX.R1, R.CH2. CH2.R1, R.CX=CX.R1, or R.CH=CH.R1. R and R1 may be hydrocarbon radicals (lists of alkyl and cycloalkyl groups are given) or may be substituted by fluorine, chlorine, bromine, carboxy, carbalkoxy, nitrilo, carbamido, hydroxy, alkoxy, acyloxy, formaldehydo, amino, alkylmercapto, sulpho, phosphato, or silicyl. The usual acid binding agents and hydrogenation catalysts may be used.  The starting materials may contain more than one trihalomethyl group, linear polymeric materials being obtained (see Group IV (a)).  Diluents specified are water, ethanol, methanol.  In examples, the following substances are hydrogenated in presence of alcoholic ammonia and a pre-reduced suspension of platinum oxide in ethanol or methanol, sometimes with a little glacial acetic acid: (1) 1.1.1.5-tetrachlorpentane to give 1.5.5.6.6.10-hexachlordecane, which is further hydrogenated to 1.10-dichlordecane, or 1.5.6.10-tetrachlordecene; (2) 1.1.1.3-tetrachlorpropane to give 1.3.3.4.4.6-hexachlorhexane and 1.3.4.6 - tetrachlor - 3 - hexene; (3) 1.1.1 - trichloro - 3 - bromopropane to give 1.6 - dibromo - 3.3.4.4 - tetrachlorhexane and 1.6 - dibromo - 3.4 - dichlorhexane; (4) 1.1.1.3-tetrachlorbutane to give 2.4.4.5.5.7-hexachloroctane; (5) 1.1.1.3 - tetrachloro - 3 - methyl butane to give 2.4.4.5.5.7-hexachloro-2.7 - dimethyloctane; (6) 1 - trichlorononane to give 9.9.10.10-tetrachlorooctadecane or 9.10-dichlorooctadecane; (7) 1.1.1.7 - tetrachloroheptane to give 1.7.7.8.8.14 - hexachlorotetradecane and 1.14-dichlorotetradecane; (8) 1.1.1-trichloro - 2 - hydroxy - 2 - methylpropane to give 3.3.4.4 - tetrachloro - 2.5 - dimethylhexanediol - 2.5; (9) 4 - trichlorobutyl acetate to give the diacetate of 4.4.5.5-tetrachlorooctane - 1.8 - diol; (10) the methyl ester of 12-trichlorododecanoic acid to give dimethyl 12.12.13.13 - tetrachlorotetracosanedioate; (11) 3.3.3 - trichloro - propane - 1 to give 3.3.4.4-tetrachlorhexadiene - 1.5; (12) methyl 4.4.4-trichlorobutyrate with 1.1.1.7 - tetrachlorheptane to give methyl 11-chlorohendecanoate, together with 1.14-dichlorotetradecane and dimethyl suberate; (13) 2.4-dibromo-4.4-dichlorobutyl acetate to give the diacetate of 2.7-dibromo - 4.4.5.5 - tetrachloro - 1.8 - octanediol; (14) 1.1.1 - tribromo - 2 - hydroxy - 2 - methylpropane to give 3.4-dibromo-2.5-dimethyl-3-hexenediol - 2.5; (15) 6 - trichlorhexane nitrile to give 6.6.7.7-tetrachlordodecane dinitrile.  A list of starting materials is given.