The Preparation of Mercaptans from Alcohols¹

Abstract

Notes 2103 perchloric acid4 and 0.5 g. of 5% palladium-on-charcoal (Wilkens-Anderson Co.). The still warm solution was shaken with hydrogen at 30-35 lb. pressure until 0.2 mole had been absorbed, about one hour. After removal of the catalyst the solution was heated to 75°and diluted with water until cloudy. Upon seeding and cooling, finally to 15°, the acid generally precipitated as an oil which later solidified. After drying in vacuo over solid sodium hydroxide the granular product weighed 20 g. It was dissolved in 130 ml. of petroleum ether (b. p. 60-70°) and treated with Norit to yield 19.8 g. (82.5%) of white needles, m. p. 74.5-75°( reported3, 75°).Four additional reductions were run as above and the reaction mixtures were combined and worked up to give the acid in 89% yield.(4) The efficacy of perchloric acid in promoting hydrogenolysis was first recognized by Karg and Marcus, Ber., 75, 1850 (1942).

Rates of reaction of n-butanethiol with some conjugated heteroenoid compounds

“…Moreover, no record could be found of the isolation of an adduct arising from the addition of a thiol to the conjugated system of a cinnamonitrile with a second functional group on the a carbon atom. In some instances, reaction proceeds without a catalyst (3,4,9) but in general, catalysts such as dry hydrogen chloride (7,8), piperidine (1, 2, 7, 8, lo), or sodium ethoxide are employed.…”

The effect of switchable additives on colloidal interactions found in oil sands as measured by chemical force spectrometry

“…The synthesis of 12-phenyldodecanethiol was accomplished using previously published literature methods [10][11][12]. The 1 H-NMR, 13 C-NMR and mass spectra (high res, EI + ) match those reported in the literature [10].…”

Thiomers of Chitosan and Cellulose: Effective Biosorbents for Detection, Removal and Recovery of Metal Ions from Aqueous Medium

“…A facile strategy for direct thiolation of alcohols is reported in 1946 by Frank et al [75] It involves treatment of alcohols by thiourea in the presence of HBr or HCl following by alkaline hydrolysis. This strategy was used by Chauhan et al with assisting of microwave irradiation for producing thiolated CTS with high degree of mercaptan groups ( CTS‐SH14 , Figure 2a) as an effective colorimetric sensor and adsorbent for Hg(II) in very low concentrations [76] .…”