Tetrahydrofuran

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

Tetrahydrofuran also known as THF is a heterocyclic organic compound with the formula (CH₂)₄O). This 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.

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Solvent properties

THF is an aprotic solvent with a 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 diethyl ether 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 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.^[1].

It is often used industrially to degrease metal parts.

Preparation

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

The major industrial process for making THF is the acid-catalyzed dehydration of 1,4-butanediol.^[3]. 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.^[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.