メルカプタンの合成に関する研究 (第2報) : α-オレフィンと硫化水素から生成するメルカプタンの尿素付加物法による精製

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The purification of mercaptans prepared from α-olefins and hydrogen sulfide by urea-adduction was investigated. Because α-olefin contains its isomers, the mercaptans prepared by radical addition of hydrogen sulfide to α-olefins are the mixture of straight-chain n-alkylmercaptans and their branched-chain isomers. As a result, it was found that the best method for separation of n-alkylmercaptans from these mixtures was the urea-adduction by reaction of solid urea with mercaptans dissolved in toluene containing a small amount of methanol. In various experimental conditions, the separations were carried out selectively, and the purified mercaptans contained over 98% of n-C10 or n-C12 mercaptan independently of the yields. The yields of n-alkylmercaptans were markedly dependent on the temperature of adduct-formation and on the solvent for the decomposition of urea-adduct. And it was suggested that the mercaptan itself might be an activator for the adduct-formation. In the case of this experimental condition, urea-adduct seemed to be not formed over 40°C and the urea-adduct of n-C8 mercaptan was hardly formed. And over the temperature range from -10°C to 30°C the rate of adduct-formation was accelerated almost linearly with lowering of temperature. The ratios of urea (moles) to the number of carbon atoms of n-mercaptans in the urea-adducts were not constant and decreased with increase of the number of carbon atoms of n-mercaptans from C8 to C18. This probably reflects the steric and polar effects of SH groups of n-mercaptans. Moreover, it was found that the formation of urea-adduct could be identified by IR spectrum. And it was qualitatively confirmed by NMR and mass spectra that the branched-chain isomers of n-mercaptans were derived from those of α-olefins.
社団法人日本油化学会の論文

メルカプタンの合成に関する研究 (第2報) : α-オレフィンと硫化水素から生成するメルカプタンの尿素付加物法による精製

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