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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.
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 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.
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.
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.
|This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Tetrahydrofuran". A list of authors is available in Wikipedia.|