Destructive Hydrogenation of High-Molecular-Weight Polymers. Isobutene Polymer, Butadiene Polymer, and Natural Rubber
Abstract Destructive hydrogenation under pressure in the presence of nickel oxide and molybdenum oxide has been used to show the presence of naphthenic hydrocarbons in high-boiling olefin polymer. It was of interest to apply this tool to other hydrocarbons having large molecules, especially rubber and synthetic rubber like polymers. The destructive hydrogenation of isobutene polymer yielded only paraffinic hydrocarbons, including isobutane in the gases. Butadiene polymer, on the other hand, gave only naphthenic products, chiefly ethylcyclohexane and a dicyclic hydrocarbon. Similarly, natural rubber yielded only naphthenes, with p-methylisopropylcyclohexane as the major component of the lower boiling portion of the product. Isoprene, under the conditions used for the destructive hydrogenation of the rubber, yielded isopentane and an unsaturated naphthene, i. e., a hydropolymer of isoprene, which was converted into p-methylisopropylcyclohexane by further hydrogenation. Discussion of the relation of these results to the structures of the polymeric substances hydrogenated is reserved for a future publication of further work now in progress undertaken to aid in the proper interpretation of the above indicated experiments.