Abstract
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.
