New Condensation Products of Rubber Hydrocarbons by the Aid of Benzyl Chloride
Abstract The application of the long-known Friedel-Crafts reaction to rubber hydrocarbons led to a new type of condensation products which may be called provisionally aral cyclorubbers (“benzylidene rubbers”), since their benzylidene groups are probably condensed with the polyprene skeleton to cyclic systems. It would not have been foreseen without further work that rubber would form this type of condensation product with aral halides in the presence of aluminum chloride, since on the one hand benzyl chloride is known to form, by the action of aluminum chloride in the Friedel-Crafts reaction, an amorphous, apparently high molecular hydrocarbon of the empirical composition (C7H6)x, and on the other hand rubber in solution is transformed by the metal chlorides, especially aluminum chloride, into amorphous polycyclorubbers. Under definite conditions of condensation with aluminum chloride aral groups are combined with the skeleton of the rubber hydrocarbon with the formation of white to yellowish amorphous bodies which contain, in addition to a small proportion of organically combined chlorine, only carbon and hydrogen, and are therefore to be regarded as hydrocarbons. In their physical and chemical properties these substances resemble the already known amorphous substance of the empirical formula (C7H6)x, which doubtless is polybenzylidene, probably hexabenzylidene.