Tetrahydrofuran

Revision as of 16:45, 20 August 2012 by WikiBot (talk | contribs) (Robot: Automated text replacement (-{{SIB}} +, -{{EH}} +, -{{EJ}} +, -{{Editor Help}} +, -{{Editor Join}} +))
(diff) ← Older revision | Latest revision (diff) | Newer revision → (diff)
Jump to navigation Jump to search

Template:Chembox new

WikiDoc Resources for Tetrahydrofuran

Articles

Most recent articles on Tetrahydrofuran

Most cited articles on Tetrahydrofuran

Review articles on Tetrahydrofuran

Articles on Tetrahydrofuran in N Eng J Med, Lancet, BMJ

Media

Powerpoint slides on Tetrahydrofuran

Images of Tetrahydrofuran

Photos of Tetrahydrofuran

Podcasts & MP3s on Tetrahydrofuran

Videos on Tetrahydrofuran

Evidence Based Medicine

Cochrane Collaboration on Tetrahydrofuran

Bandolier on Tetrahydrofuran

TRIP on Tetrahydrofuran

Clinical Trials

Ongoing Trials on Tetrahydrofuran at Clinical Trials.gov

Trial results on Tetrahydrofuran

Clinical Trials on Tetrahydrofuran at Google

Guidelines / Policies / Govt

US National Guidelines Clearinghouse on Tetrahydrofuran

NICE Guidance on Tetrahydrofuran

NHS PRODIGY Guidance

FDA on Tetrahydrofuran

CDC on Tetrahydrofuran

Books

Books on Tetrahydrofuran

News

Tetrahydrofuran in the news

Be alerted to news on Tetrahydrofuran

News trends on Tetrahydrofuran

Commentary

Blogs on Tetrahydrofuran

Definitions

Definitions of Tetrahydrofuran

Patient Resources / Community

Patient resources on Tetrahydrofuran

Discussion groups on Tetrahydrofuran

Patient Handouts on Tetrahydrofuran

Directions to Hospitals Treating Tetrahydrofuran

Risk calculators and risk factors for Tetrahydrofuran

Healthcare Provider Resources

Symptoms of Tetrahydrofuran

Causes & Risk Factors for Tetrahydrofuran

Diagnostic studies for Tetrahydrofuran

Treatment of Tetrahydrofuran

Continuing Medical Education (CME)

CME Programs on Tetrahydrofuran

International

Tetrahydrofuran en Espanol

Tetrahydrofuran en Francais

Business

Tetrahydrofuran in the Marketplace

Patents on Tetrahydrofuran

Experimental / Informatics

List of terms related to Tetrahydrofuran

For other uses of THF, see THF (disambiguation)

Tetrahydrofuran is a heterocyclic organic compound. It is a clear, low-viscosity liquid with a diethyl ether-like smell. It is one of the most polar ethers and is used as a solvent of intermediate polarity in chemical reactions. THF is an aprotic, electron donating solvent with a dielectric constant of 7.6. THF is the fully hydrogenated analog of the aromatic compound furan.

Uses

THF is a moderately polar, aprotic solvent. It is able to dissolve a wide range of compounds.

Diethyl ether can often be substituted with THF, especially 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 atom on 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. 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.

External links

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

References

  1. "Polyethers, Tetrahydrofuran and Oxetane Polymers by Gerfried Pruckmayr, P. Dreyfuss, M. P. Dreyfuss". Kirk‑Othmer Encyclopedia of Chemical Technology. John Wiley & Sons, Inc. 1996.
  2. Morrison, Robert Thornton; Boyd, Robert Neilson: Organic Chemistry, 2nd ed., Allyn and Bacon 1972, p 569
  3. 3.0 3.1 "Ethers, by Lawrence Karas and W. J. Piel". Kirk‑Othmer Encyclopedia of Chemical Technology. John Wiley & Sons, Inc. 2004. |access-date= requires |url= (help)
  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.

de:Tetrahydrofuran it:Tetraidrofurano lv:THF nl:Tetrahydrofuraan fi:Tetrahydrofuraani sv:Tetrahydrofuran

Template:WH Template:WikiDoc Sources Template:Jb1