Patent GB-473653-A (GB)
Title: Improvements in the manufacture and production of carbon compounds of high molecularweight
IPC: C07C2/86
Filed: 1936-04-15
Abstract: Compounds of the general formula R--(A--B)n where R is the radicle of an aromatic hydrocarbon having at least four condensed rings, A is --CO-- or --CH2--, B is the radicle of an aliphatic or cycloaliphatic hydrocarbon containing at least 7 carbon atoms, and n is a whole number, are manufactured by reacting hydrocarbons containing at least four condensed rings with aliphatic or cycloaliphatic compounds containing at least 8 carbon atoms, the initial materials being so chosen that one of them contains at least one halogen atom which permits of the connection of the initial materials by an open carbon bridge.  The reaction may be effected by reacting hydrocarbons having at least four condensed rings, e.g. benzanthrene, pyrenes, chrysenes, perylenes, benzpyrenes, triphenylenes, coronenes, naphthanthracenes, pyranthrenes, or hydropyrenes with aliphatic or cycloaliphatic compounds containing at least 8 carbon atoms and a halogen atom attached to a carbon atom not combined in a ring, e.g. alkyl halides such as octyl chloride, dodecyl bromide, octodecyl chloride or octodecenyl chloride, halogen compounds of abietene or of compounds of the naphthene series containing at least 8 carbon atoms, halogen derivatives of cycloaliphatic compounds such as ethyl-, propyl- or hexylcyclohexanes, or halogen derivatives of cycloaliphatic compounds containing a plurality of aliphatic side chains such as dipropylcyclopentanes or -hexanes. Alternatively, the halogen atoms may be in the hydrocarbons having at least four condensed rings, in which case the reaction is preferably effected in the presence of a condensing agent of the Friedel-Crafts type.  Instead of the halogenated hydrocarbons there may be used the corresponding carboxylic acid halides, the --CO.halogen groups being contained either in the hydrocarbon having at least four condensed rings or in the compounds containing at least 8 carbon atoms.  The reaction is effected with or without heating, preferably in the presence of solvents or diluents, e.g. halogen hydrocarbons or carbon disulphide, and of substances promoting the reaction, e.g. anhydrous halides of metals such as aluminium, iron or zinc.  The products are suitable for colouring or rendering fluorescent hydrocarbons, fats, waxes, natural and synthetic oils, natural and synthetic plastic masses, synthetic resins and lacquers.  In examples: (1) pyrene or chrysene is heated with n-octyl chloride in the presence of aluminium chloride; (2) perylene is stirred with stearic acid chloride and aluminium chloride in chlorobenzene; (3) the stearic acid chloride is replaced by lauric or oleic acid chloride; (4) perylene is stirred with stearic acid chloride and aluminium chloride in dichlorobenzene, and then with benzoyl chloride; (5) perylene is heated with stearic acid chloride; the perylene may be replaced by chrysene, benzperylenes, hydroperylenes or coronene, and the stearic acid chloride by the mixture of chlorides of the fatty acids of palm kernel oil or the chlorides of undecane-, heptadecane- or heptadecylene-carboxylic acids.  Specifications 401,341, 416,379, and 453,778 are referred to.