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Title: Tetrahydrofuran  
Author: World Heritage Encyclopedia
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Subject: Ether, Adduct, Furan, Grignard reaction, Holton Taxol total synthesis
Collection: Ether Solvents, Tetrahydrofurans
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Space-filling model of the THF molecule
IUPAC name
Other names
THF, tetrahydrofuran, 1,4-epoxybutane, butylene oxide, cyclotetramethylene oxide, oxacyclopentane, diethylene oxide, furanidine, hydrofuran, tetra-methylene oxide
ChemSpider  Y
Jmol-3D images Image
RTECS number LU5950000
Molar mass 72.11 g·mol−1
Appearance colorless liquid
Odor ether-like[1]
Density 0.8892 g/cm3 @ 20 °C, liquid
Melting point −108.4 °C (−163.1 °F; 164.8 K)
Boiling point 66 °C (151 °F; 339 K)
Vapor pressure 132 mmHg (20°C)[1]
Viscosity 0.48 cP at 25 °C
1.63 D (gas)
Safety data sheet See: data page
Flammable (F)
Irritant (Xi)
R-phrases R11, R19, R20/21/22, R36/37
S-phrases S16, S29, S33
NFPA 704
Flash point −14 °C (7 °F; 259 K)
Explosive limits 2%-11.8%[1]
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)[2]
21000 ppm (rat, 3 hr)[2]
US health exposure limits (NIOSH):
PEL (Permissible)
TWA 200 ppm (590 mg/m3)[1]
REL (Recommended)
TWA 200 ppm (590 mg/m3) ST 250 ppm (735 mg/m3)[1]
2000 ppm[1]
Related compounds
Related heterocycles
Related compounds
Diethyl ether
Supplementary data page
Refractive index (n),
Dielectric constantr), etc.
Phase behaviour
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 N  (: Y/N?)

Tetrahydrofuran (THF) is an viscosity. It is mainly used as a precursor to polymers.[4] Being polar and having a wide liquid range, THF is a versatile solvent.


  • Production 1
    • Other methods 1.1
  • Applications 2
    • As a solvent 2.1
    • Purification 2.2
    • Potential uses and research 2.3
    • Other uses 2.4
  • 2-MethylTHF 3
  • Precautions 4
  • See also 5
  • References 6
  • General reference 7
  • External links 8


About two hundred thousand tonnes of tetrahydrofuran are produced annually.[5] The most widely used industrial process involves the acid-catalyzed dehydration of 1,4-butanediol. 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.[4] Du Pont developed a process for producing THF by oxidizing n-butane to crude maleic anhydride followed by catalytic hydrogenation.[6] A third major industrial route entails hydroformylation of allyl alcohol followed by hydrogenation to the butanediol.

Other methods

THF can also be synthesized by catalytic hydrogenation of furan.[7][8] Certain sugars can be converted to THF although this method is not widely practiced. Furan is thus derivable from renewable resources.


In the presence of strong acids, THF converts to a linear polymer called poly(tetramethylene ether) glycol (PTMEG), also known as PTMO, polytetramethylene oxide:

n C4H8O → -(CH2CH2CH2CH2O)n-

This polymer is primarily used to make elastomeric polyurethane fibers like Spandex.[9]

As a solvent

The other main application of THF is as an industrial solvent for PVC and in varnishes.[4] It is an aprotic solvent with a dielectric constant of 7.6. It is a moderately polar solvent and can dissolve a wide range of nonpolar and polar chemical compounds.[10] THF is water-miscible, and can form solid clathrate hydrate structures with water at low temperatures.[11]

In the laboratory, THF is a popular solvent when its water miscibility is not an issue. It is more Grignard reagents.[12] Although similar to diethyl ether, THF is a stronger base.[13] Thus, while diethyl ether remains the solvent of choice for some reactions (e.g., Grignard reactions), THF fills that role in many others where strong coordination is desirable, and the precise properties of ethereal solvents such as these (alone and in mixtures and at various temperatures) allows for fine-tuning modern chemical reactions.


Commercial THF contains substantial water that must be removed for sensitive operations, e.g. those involving distillation from an aggressive desiccant, molecular sieves are far superior.[14]

Drying of THF
Drying agent Duration of drying water content
none 0 hours 108 ppm
Sodium/benzophenone 48 h 43 ppm
3 A molecular sieves (20% by volume) 72 h 4 ppm

Potential uses and research

THF has been explored as a miscible co-solvent in aqueous solution to aid in the liquefaction and delignification of plant [15] Aqueous THF augments the hydrolysis of glycans from biomass and dissolves the majority of biomass lignin making it a suitable solvent for biomass pretreatment.

THF is often used in polymer science. For example, it can be used to dissolve polymers prior to determining their molecular mass using gel permeation chromatography. THF dissolves PVC as well, and thus it is the main ingredient in PVC adhesives. It can be used to liquefy old PVC cement, and is often used industrially to degrease metal parts.

THF is used as a component in mobile phases for reversed-phase liquid chromatography. It has a greater elution strength than methanol or acetonitrile, but is less commonly used than these solvents.

Other uses

THF is also a starting material for the preparation of tetrahydrothiophene. In the presence of a solid acid catalyst, it reacts with hydrogen sulfide.[16]


2-Methyltetrahydrofuran (2MeTHF) has been promoted as an ecologically friendler alternative to THF.[17] Whereas 2-MeTHF is more expensive, it may provide for greater overall process economy. 2MeTHF has solvating properties that are intermediate between diethyl ether and THF, has limited water-miscibility, and forms an azeotrope with water on distillation. Its lower melting point makes it useful for lower temperature reactions, and its higher boiling point allows procedures under reflux at higher temperatures (relative to THF).


THF is considered a relatively nontoxic solvent, with the median lethal dose (LD50) comparable to that for acetone. However, it is suspected to cause cancer. [18] Reflecting its remarkable solvent properties, it penetrates the skin causing rapid dehydration. THF readily dissolves latex and is typically handled with nitrile or neoprene rubber gloves. It is highly flammable.

One danger posed by THF follows from its tendency to form highly-explosive peroxides on storage in air. To minimize this problem, commercial samples of THF are often inhibited with BHT. THF should not be distilled to dryness, because the explosive peroxides concentrate in the residue.

See also


  1. ^ a b c d e f "NIOSH Pocket Guide to Chemical Hazards #0602".  
  2. ^ a b "Tetrahydrofuran". Immediately Dangerous to Life and Health.  
  3. ^
  4. ^ a b c Herbert Müller, "Tetrahydrofuran" in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. doi:10.1002/14356007.a26_221
  5. ^ "Ethers, by Lawrence Karas and W. J. Piel". Kirk‑Othmer Encyclopedia of Chemical Technology. John Wiley & Sons, Inc. 2004. 
  6. ^ Merck Index of Chemicals and Drugs, 9th ed.
  7. ^ Morrison, Robert Thornton; Boyd, Robert Neilson: Organic Chemistry, 2nd ed., Allyn and Bacon 1972, p. 569
  8. ^ Donald Starr and R. M. Hixon (1943). "Tetrahydrofuran".  
  9. ^ "Polyethers, Tetrahydrofuran and Oxetane Polymers by Gerfried Pruckmayr, P. Dreyfuss, M. P. Dreyfuss". Kirk‑Othmer Encyclopedia of Chemical Technology. John Wiley & Sons, Inc. 1996. 
  10. ^ "Chemical Reactivity". Retrieved 2010-02-15. 
  11. ^ "" (PDF). Retrieved 2010-02-15. 
  12. ^ Elschenbroich, C.; Salzer, A. ”Organometallics : A Concise Introduction” (2nd Ed) (1992) Wiley-VCH: Weinheim. ISBN 3-527-28165-7
  13. ^ Lucht, B.L.; Collum, D.B. (1999). "Lithium Hexamethyldisilazide: A View of Lithium Ion Solvation through a Glass-Bottom Boat". Accounts of Chemical Research 32: 1035–1042.  , and references therein.
  14. ^ Williams, D. B. G., Lawton, M., "Drying of Organic Solvents: Quantitative Evaluation of the Efficiency of Several Desiccants", The Journal of Organic Chemistry 2010, vol. 75, 8351. doi:10.1021/jo101589h
  15. ^ Cai, Charles; Zhang, Taiying; Kumar, Rajeev; Wyman, Charles (13 August 2013). "THF co-solvent enhances hydrocarbon fuel precursor yields from lignocellulosic biomass". Green Chemistry 15: 3140–3145.  
  16. ^ Jonathan Swanston "Thiophene" in Ullmann’s Encyclopedia of Industrial Chemistry Wiley-VCH, Weinheim, 2006. doi:10.1002/14356007.a26_793.pub2.
  17. ^ "Greener Solvent Alternatives – Brochure" (PDF). Retrieved 2010-02-15. 
  18. ^

General reference

External links

  • International Chemical Safety Card 0578
  • NIOSH Pocket Guide to Chemical Hazards
  • THF usage
  • U.S. OSHA info on THF
  • "2-Methyltetrahydrofuran, An alternative to Tetrahydrofuran and Dichloromethane". Sigma-Aldrich. Retrieved 2007-05-23. 
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