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Noun

tetrahydrofuran
  1. a heterocyclic ether having a five-membered ring with four carbon atoms and one carbon; it is a colourless liquid with an ether-like smell, and is used as a polar solvent

Extensive Definition

"THF" redirects here. For other uses, see THF (disambiguation).
Tetrahydrofuran, also known as THF, is a heterocyclic organic compound with the formula (CH2)4O). It is a colourless low-viscosity liquid with a smell similar to diethyl ether. It is one of the most polar ethers. THF is the fully hydrogenated analog of the aromatic compound furan.

Solvent properties

THF is an aprotic solvent with a dielectric constant of 7.6. It is a moderately polar, aprotic solvent that dissolves a wide range of nonpolar and polar compounds.
Diethyl ether can often be substituted by THF when a higher-boiling solvent is required. Thus THF, like diethyl ether, is often used for hydroborations used to synthesize primary alcohols. Both ethers have an oxygen atom which can coordinate to the electron-deficient boron atom, forming an adduct. Similarly, THF or diethyl ether are often used as solvents for Grignard reagents because of the oxygen atom's ability to coordinate to the magnesium ion component of the Grignard reagent. In addition, the oxygen atom has no acid hydrogen that can undergo acid-base reaction with the Grignard reagent. 2-methyltetrahydrofuran has become a popular THF alternative, based on its similar properties to THF, but having a lower melting point (useful for lower temperature reactions), as well as having a higher boiling point (useful for solvent retention under reflux).
THF is often used in polymer science. For example, it can be used to dissolve rubber prior to determining its molecular mass using gel permeation chromatography. THF dissolves PVC as well, and is the main ingredient in PVC adhesives. It can be used to liquefy old PVC cement.
THF can be polymerized by strong acids to give a linear polymer called poly(tetramethylene ether) glycol (PTMEG), CAS Registry Number [25190-06-1], also known as PTMO, polytetramethylene oxide. The primary use of this polymer is to make elastomeric polyurethane fibers like Spandex..
It is often used industrially to degrease metal parts.

Preparation

THF can be synthesized by catalytic hydrogenation of furan.
The major industrial process for making THF is the acid-catalyzed dehydration of 1,4-butanediol. Du Pont developed a process for producing THF by oxidizing n-butane to crude maleic anhydride, followed by catalytic hydrogenation of maleic anhydride to THF.

Precautions

THF tends to form peroxides on storage in air. As a result, THF should not be distilled to dryness, which can leave a residue of highly-explosive peroxides. Commercial THF is therefore often inhibited with BHT.

See also

  • The Trapp mixture extends the temperature range applicability of THF as a solvent.

References

  • Loudon, G. Mark. Organic Chemistry 4th ed. New York: Oxford University Press. 2002. pg 318.
tetrahydrofuran in German: Tetrahydrofuran
tetrahydrofuran in Spanish: Tetrahidrofurano
tetrahydrofuran in French: Tétrahydrofurane
tetrahydrofuran in Italian: Tetraidrofurano
tetrahydrofuran in Latvian: THF
tetrahydrofuran in Dutch: Tetrahydrofuraan
tetrahydrofuran in Japanese: テトラヒドロフラン
tetrahydrofuran in Polish: Tetrahydrofuran
tetrahydrofuran in Portuguese: Tetraidrofurano
tetrahydrofuran in Russian: Тетрагидрофуран
tetrahydrofuran in Finnish: Tetrahydrofuraani
tetrahydrofuran in Swedish: Tetrahydrofuran
tetrahydrofuran in Chinese: 四氢呋喃
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