Tetrahydrofuran

"THF" redirects here. For other uses, see THF (disambiguation).

Tetrahydrofuran also known as THF is a furan.

Solvent properties

THF is an dielectric constant of 7.6. It is a moderately polar, aprotic solvent that dissolve a wide range of nonpolar and polar compounds.

THF can often be substituted 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 gel permeation chromatography.

THF can be Spandex.^[1].

It is often used industrially to degrease metal parts.

Preparation

THF can be synthesized by catalytic furan^[2].

The major industrial process for making THF is the acid-catalyzed dehydration of maleic anhydride to THF.^[3][4]

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.

• THF usage on Organic Syntheses
• THF info
• U.S. OSHA info on THF

• 2-Methyltetrahydrofuran, An alternative to Tetrahydrofuran and Dichloromethane. Sigma-Aldrich. Retrieved on 2007-05-23.

• Tetrahydrafuran (THF) Storage and Handling. BASF. Retrieved on 2007-05-24.

References

1. ^ "Polyethers, Tetrahydrofuran and Oxetane Polymers by Gerfried Pruckmayr, P. Dreyfuss, M. P. Dreyfuss". Kirk‑Othmer Encyclopedia of Chemical Technology. (1996). John Wiley & Sons, Inc. 
2. ^ Morrison, Robert Thornton; Boyd, Robert Neilson: Organic Chemistry, 2nd ed., Allyn and Bacon 1972, p 569
3. ^ ^{a b} "Ethers, by Lawrence Karas and W. J. Piel". Kirk‑Othmer Encyclopedia of Chemical Technology. (2004). John Wiley & Sons, Inc. Retrieved on 2007-09-05. 
4. ^ Merck Index of Chemicals and Drugs, 9th ed. monograph 8929

• Loudon, G. Mark. Organic Chemistry 4th ed. New York: Oxford University Press. 2002. pg 318.

See also

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