メルカプタンの合成に関する研究 (第3報) : アルコール系溶媒中での塩化ラウリルと水硫化ナトリウムの反応

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The reaction conditions for the synthesis of lauryl mercaptan (RSH) from lauryl chloride (RCl) and sodium hydrogensulfide (NaSH, flakes, 68% purity) were investigated in alcoholic solvents (mainly in n-butanol). There was no definite relation between the yields of RSH and the dielectric constants or solvent polarity parameters of the alcooholic (hydroxylic) solvents used; methanol, ethanol, propanols, butanols and n-amyl alchol. The yield of RSH in dimethylformamide (a dipolar aprotic solvent) was higher (by 25.1, 21.2, and 28.9%) than in ethanol, n-propanol and n-butanol, respectively. Accordingly, from a viewpoint of reaction mechanism, it was suggested as necessary that the reaction of RCl with NaSH in alcoholic solvents should be investigated in detail. The reactions in n-butanol were markedly influenced by reaction temperature and amount of water, and it was suggested that a side reaction, namely the formation of di-n-dodecyl sulfide (RSR), occurred as follows; 1) 2NaSH _??_ Na2S+H2S Na2S+2RCl→RSR+2NaCl and/or 2) RSH+NaSH _??_ RSNa+H2S RSNa+RCl→RSR+NaCl. Moreover, the effects of some reaction conditions on the yields of RSH and the formations of RSR were investigated, and the results were discussed based on the reaction mechanism previously proposed.
社団法人日本油化学会の論文