Tetrahydrothiophene
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| Names | |||
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| IUPAC name
Thiolane
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| Other names
Tetrahydrothiophene,
thiophane, tetramethylene sulfide | |||
| Identifiers | |||
3D model (JSmol)
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| Abbreviations | THT | ||
| ChEBI | |||
| ChEMBL | |||
| ChemSpider | |||
| ECHA InfoCard | 100.003.391 | ||
CompTox Dashboard (EPA)
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| Properties | |||
| C4H8S | |||
| Molar mass | 88.17 g·mol−1 | ||
| Density | 0.997 g/mL[1] | ||
| Melting point | −96 °C (−141 °F; 177 K) | ||
| Boiling point | 119 °C (246 °F; 392 K) | ||
| Hazards | |||
| Occupational safety and health (OHS/OSH): | |||
Main hazards
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Stench, flammable, irritant | ||
| Safety data sheet (SDS) | Oakwood | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Tetrahydrothiophene is an organosulfur compound with the formula (CH2)4S. It consists of a five-membered ring containing four carbon atoms and a sulfur atom. It is the saturated analog of thiophene. It is a volatile, colorless liquid with an intensely unpleasant odor. It is also known as thiophane, thiolane or THT.
Synthesis and reactions
It is prepared by the reaction of tetrahydrofuran with hydrogen sulfide. This vapor-phase reaction is catalyzed by alumina and other heterogenous acid catalysts.[2][3]
This compound is a ligand in coordination chemistry, an example being the complex chloro(tetrahydrothiophene)gold(I).[4]
Oxidation of THT gives the solvent called sulfolane, a polar solvent with almost no odor. Sulfolane is more conventionally prepared from butadiene.
Applications
Because of its smell, tetrahydrothiophene has been used as an odorant in LPG,[3] albeit no longer in North America. It is also used as an odorant for natural gas, usually in mixtures containing tert-butylthiol.
See also
References
- ^ [1] Wilfred L.F. Armarego, Christina Li Lin Chai, Purification of Laboratory Chemicals (Fifth Edition), 2003, p. 361
- ^ Bernard Loev and John T. Massengale, U. S. Patent 2,899,444, "Synthesis of Tetrahydrothiophene", 8/11/1959
- ^ a b Jonathan Swanston “Thiophene” in Ullmann’s Encyclopedia of Industrial Chemistry Wiley-VCH, Weinheim, 2006. doi:10.1002/14356007.a26_793.pub2.
- ^ Rafael Uson, Antonio Laguna, Mariano Laguna, "(Tetrahydrothiophene)Gold(I) or Gold(III) Complexes" Inorganic Syntheses, 1989, Volume 26, pp. 85–91. doi:10.1002/9780470132579.ch17