Tetrahydrothiophene

Tetrahydrothiophene
Names
IUPAC name
Thiolane
Other names
Tetrahydrothiophene,
thiophane, tetramethylene sulfide
Identifiers
3D model (JSmol)
Abbreviations THT
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.391
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
Main hazards Stench, flammable, irritant
Safety data sheet 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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Infobox references

Tetrahydrothiophene is an organosulfur compound with the formula (CH2)4S. It contains a five-membered ring consisting of 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
  2. ↑ Bernard Loev and John T. Massengale, U. S. Patent 2,899,444, "Synthesis of Tetrahydrothiophene", 8/11/1959
  3. 1 2 Jonathan Swanston “Thiophene” in Ullmann’s Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2006. doi:10.1002/14356007.a26_793.pub2
  4. ↑ . doi:10.1002/9780470132579.ch17. Missing or empty |title= (help)
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