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Butylene oxide

Tetrahydrofuran
Skeletal formula of tetrahydrofuran
Ball-and-stick model of the tetrahydrofuran molecule
Photograph of a glass bottle of tetrahydrofuran
Names
Preferred IUPAC name
Oxolane
Other names
Tetrahydrofuran
1,4-Epoxybutane
Butylene oxide
Cyclotetramethylene oxide
Oxacyclopentane
Diethylene oxide
Tetra-methylene oxide
Identifiers
3D model (JSmol)
Abbreviations THF
ChEBI
ChemSpider
ECHA InfoCard 100.003.389
PubChem CID
RTECS number LU5950000
Properties
C4H8O
Molar mass 72.11 g·mol−1
Appearance colorless liquid
Odor ether-like
Density 0.8892 g/cm3 at 20 °C, liquid
Melting point −108.4 °C (−163.1 °F; 164.8 K)
Boiling point 66 °C (151 °F; 339 K)
Miscible
Vapor pressure 132 mmHg (20 °C)
Viscosity 0.48 cP at 25 °C
Structure
envelope
1.63 D (gas)
Hazards
Safety data sheet See: data page
Flammable (F)
Irritant (Xi)
R-phrases (outdated) R11, R19, R20/21/22, R36/37
S-phrases (outdated) S16, S29, S33
NFPA 704
Flammability code 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g., gasoline) Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform Reactivity code 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g., calcium Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point −14 °C (7 °F; 259 K)
Explosive limits 2%–11.8%
Lethal dose or concentration (LD, LC):
LD50 (median dose)
1650 mg/kg (rat, oral)
2300 mg/kg (mouse, oral)
2300 mg/kg (guinea pig, oral)
21000 ppm (rat, 3 hr)
US health exposure limits (NIOSH):
PEL (Permissible)
TWA 200 ppm (590 mg/m3)
REL (Recommended)
TWA 200 ppm (590 mg/m3) ST 250 ppm (735 mg/m3)
IDLH (Immediate danger)
2000 ppm
Related compounds
Related heterocycles
Furan
Pyrrolidine
Dioxane
Related compounds
Diethyl ether
Supplementary data page
Refractive index (n),
Dielectric constantr), etc.
Thermodynamic
data
Phase behaviour
solid–liquid–gas
UV, IR, NMR, MS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YesYN ?)
Infobox references

Tetrahydrofuran (THF), whose preferred IUPAC name was changed in 2013 to 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.

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 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 the butanediol.

THF can also be synthesized by catalytic hydrogenation of furan.Certain sugars can be converted to THF, although this method is not widely practiced. Furan is thus derivable from renewable resources.


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Wikipedia

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