tetrahydrofuran
Also known as diethylene oxide, 1,4-epoxybutane, tetramethylene oxide, THF, furanidine, butylene oxide, butane alpha,delta-oxide, Tetrahydrofuraan
Tetrahydrofuran (THF), or oxolane, is an organic compound with the formula (CH2)4O. The compound is classified as heterocyclic compound, specifically a cyclic ether. It is a colorless, water-miscible organic liquid with low viscosity. It is mainly used as a precursor to polymers. Being polar and having a wide liquid range, THF is a versatile solvent. It is an isomer of another solvent, butanone.
Chemical data
- Formula
- C4H8O
- Molecular weight
- 72.11 g/mol
- IUPAC name
- oxolane
- SMILES
- C1CCOC1
- InChIKey
- WYURNTSHIVDZCO-UHFFFAOYSA-N
- XLogP
- 0.5
- Polar surface area
- 9.2 Ų
- H-bond donors
- 0
- H-bond acceptors
- 1
- Formal charge
- 0
via PubChem
Article
16 sectionsContents
- Production
- Other methods
- Applications
- Polymerization
- As a solvent
- Laboratory use
- Reaction with hydrogen sulfide
- Lewis basicity
- Precautions
- Related compounds
- Tetrahydrofurans
- Oxolanes
- See also
- References
- General reference
- External links
Tetrahydrofuran (THF), or oxolane, is an organic compound with the formula (CH2)4O. The compound is classified as heterocyclic compound, specifically a cyclic ether. It is a colorless, water-miscible organic liquid with low viscosity. It is mainly used as a precursor to polymers. Being polar and having a wide liquid range, THF is a versatile solvent. It is an isomer of another solvent, butanone.
==Production== About 200,000 tonnes of tetrahydrofuran are produced annually. The most widely used industrial process involves the acid-catalyzed dehydration of 1,4-butanediol. Ashland/ISP is one of the biggest producers of this chemical route. The method is similar to the production of diethyl ether from ethanol. The butanediol is derived from condensation of acetylene with formaldehyde followed by hydrogenation. DuPont developed a process, for producing THF by oxidizing n-butane to crude maleic anhydride, followed by catalytic hydrogenation. A third major industrial route entails hydroformylation of allyl alcohol followed by hydrogenation to 1,4-butanediol.