Tetrahydrothiophene

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Tetrahydrothiophene
Tetrahydrothiophene.svg
Tetrahydrothiophene3d.png
Names
IUPAC name
Thiolane
Other names
Tetrahydrothiophene,
thiophane, tetramethylene sulfide
Identifiers
3D model (JSmol)
Abbreviations THT
ChEBI
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 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[edit]

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[edit]

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[edit]

References[edit]

  1. ^ [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. ^ a b Jonathan Swanston “Thiophene” in Ullmann’s Encyclopedia of Industrial Chemistry Wiley-VCH, Weinheim, 2006. doi:10.1002/14356007.a26_793.pub2.
  4. ^ 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