Cyclohexanethiol
(Redirected from Cyclohexyl mercaptan)
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| Names | |
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| Preferred IUPAC name
Cyclohexanethiol | |
| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.014.890 |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C6H12S | |
| Molar mass | 116.22 g·mol−1 |
| Appearance | Colorless liquid |
| Density | 0.95 g/cm3 |
| Boiling point | 158 to 160 °C (316 to 320 °F; 431 to 433 K) |
| Low | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Cyclohexanethiol is a thiol with the formula C6H11SH. It is a colorless liquid with a strong odor.
Preparation
[edit]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 + H2O
It is also obtained by the addition of hydrogen sulfide to cyclohexene in the presence of nickel sulfide.[2]
Safety
[edit]The LD50 (injected, mice) was estimated at 316 mg/kg by the United States Department of Health, Education, and Welfare.[3]
References
[edit]- ^ 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. doi:10.1021/ja01847a508.
- ^ Kathrin-Maria Roy "Thiols and Organic sulphides" in Ullmann's Encyclopedia of Industrial Chemistry, 2002, Wiley-VCH Verlag, Weinheim. doi:10.1002/14356007.a26_767
- ^ Occupational Exposure to N-alkane Mono Thiols, Cyclohexanethiol, and Benzenethiol. U.S. Government Printing Office. 1978.