ゴムの硫黄加硫:1-メチルシクロヘキセンと硫黄の反応

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To decide on the mechanism of the vulcanization of the natural rubber, the reaction of 1-methylcyclohexene, as a low molecular weight model compound for rubber, with sulfur and benzylmercaptane were studied.The mole ratios of 1-methylcyclohexene to sulfur were 100/1.4 and 100/12.5, and in the reaction of 1-methylcyclohexene with mercaptane, equivalent mixture of the reactants in the mole ratio was used. The reactions were carried out at 140°C. in a sealed tube for 24hr. in the dark. The products were isolated by column chromatography on silica gel.From the results of the elemental analpsis and infrared spectra of the isolated products, it was confirmed that hydrogen sulfide, 3-methylcyclohexene and different sulfides shown below, were formed in the reactions.From these results, it was found that in the initial stage, addition of sulfur to olefin went by free radical mechanism, and as mercaptan, formed in subsequent reaction step, coexist with sulfur, ionic addition reaction of mercaptane to double bond in the olefin occured competitively with free radical reaction._??_
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