Cyclohexanethiol Explained

Cyclohexanethiol is a thiol with the formula C₆H₁₁SH. It is a colorless liquid with a strong odor.

Preparation

It was first prepared by the free-radical reaction of cyclohexane using carbon disulfide as a sulfur source.^[1]

It is produced industrially by the hydrogenation of cyclohexanone in the presence of hydrogen sulfide over a metal sulfide catalyst:

C₆H₁₀O + H₂S + H₂ → C₆H₁₁SH + H₂OIt is also obtained by the addition of hydrogen sulfide to cyclohexene in the presence of nickel sulfide.^[2]

Safety

The (injected, mice) was estimated at 316 mg/kg by the United States Department of Health, Education, and Welfare.^[3]

Notes and References

1. Kharasch . M.S. . Eberly . Kenneth . February 1941 . Reactions of Atoms and Free Radicals in Solution. III. The Introduction of a Mercaptan Group into Cyclohexane . J. Am. Chem. Soc. . 63 . 2 . 625 . 10.1021/ja01847a508 .
2. Kathrin-Maria Roy "Thiols and Organic sulphides" in Ullmann's Encyclopedia of Industrial Chemistry, 2002, Wiley-VCH Verlag, Weinheim.
3. Book: 1978 . Occupational Exposure to N-alkane Mono Thiols, Cyclohexanethiol, and Benzenethiol . U.S. Government Printing Office .