|Preferred IUPAC name
3D model (JSmol)
CompTox Dashboard (EPA)
|Molar mass||98.10 g/mol|
|Melting point||−29 °C (−20 °F; 244 K)|
|Boiling point||170 °C (338 °F; 443 K)|
|Safety data sheet||External MSDS|
|Flash point||65 °C; 149 °F; 338 K |
|Explosive limits||1.8% - 16.3%|
|Lethal dose or concentration (LD, LC):|
LC50 (median concentration)
|397 ppm (mouse, 6 hr)|
85 ppm (rat, 6 hr)
592 ppm (rat, 1 hr)
LCLo (lowest published)
|597 ppm (mouse, 6 hr)|
|US health exposure limits (NIOSH):|
|TWA 50 ppm (200 mg/m3)|
|TWA 10 ppm (40 mg/m3) ST 15 ppm (60 mg/m3) [skin]|
IDLH (Immediate danger)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
Furfuryl alcohol is an organic compound containing a furan substituted with a hydroxymethyl group. It is a colorless liquid, but aged samples appear amber. It possesses a faint odor of burning and a bitter taste. It is miscible with but unstable in water. It is soluble in common organic solvents.
Furfuryl alcohol is manufactured industrially by hydrogenation of furfural, which is itself typically produced from waste bio-mass such as corncobs or sugar cane bagasse. As such furfuryl alcohol may be considered a green chemical.
It undergoes many reactions including Diels-Alder additions to electrophilic alkenes and alkynes. Hydroxymethylation gives 1,5-bis(hydroxymethyl)furan. Hydrolysis gives levulinic acid. Upon treatment with acids, heat and/or catalysts, furfuryl alcohol can be made to polymerize into a resin, poly(furfuryl alcohol). Hydrogenation of furfuryl alcohol can proceed to give hydroxymethyl derivative of tetrahydrofuran and 1,5-pentanediol.
The primary use of furfuryl alcohol is as a monomer for the synthesis of furan resins. These polymers are used in thermoset polymer matrix composites, cements, adhesives, coatings and casting/foundry resins. Polymerization involves an acid-catalyzed polycondensation, usually giving a black cross-linked product. A highly simplified representation is shown below.
Furfuryl alcohol has been used in rocketry as a fuel which ignites hypergolically (immediately and energetically in contact) with white fuming nitric acid or red fuming nitric acid oxidizer. The use of hypergolics avoids the need for an igniter. In late 2012, Spectra, a concept liquid rocket engine using white fuming nitric acid as the oxidizer to furfuryl alcohol fuel was static tested by Copenhagen Suborbitals.
Because of its low molecular weight, furfuryl alcohol can impregnate the cells of wood, where it can be polymerized and bonded with the wood by heat, radiation, and/or catalysts or additional reactants. The treated wood has improved moisture-dimensional stability, hardness, and decay and insect resistance; catalysts can include zinc chloride, citric, and formic acid, as well as borates.
- Furfurylamine - corresponding amine
- 2-Furonitrile - corresponding nitrile
- Furan-2-ylmethanethiol - corresponding thiol
- 2-Furoic acid - corresponding carboxylic acid
- Choura, Mekki; Belgacem, Naceur M.; Gandini, Alessandro (January 1996). "Acid-Catalyzed Polycondensation of Furfuryl Alcohol: Mechanisms of Chromophore Formation and Cross-Linking". Macromolecules. 29 (11): 3839–3850. doi:10.1021/ma951522f.
- Merck Index, 11th Edition, 4215.
- NIOSH Pocket Guide to Chemical Hazards. "#0298". National Institute for Occupational Safety and Health (NIOSH).
- "Furfuryl alcohol". Immediately Dangerous to Life and Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
- Hoydonckx, H. E.; Van Rhijn, W. M.; Van Rhijn, W.; De Vos, D. E.; Jacobs, P. A. "Furfural and Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a12_119.pub2.
- Mariscal, R.; Maireles-Torres, P.; Ojeda, M.; Sádaba, I.; López Granados, M. (2016). "Furfural: a renewable and versatile platform molecule for the synthesis of chemicals and fuels". Energy Environ. Sci. 9 (4): 1144–1189. doi:10.1039/C5EE02666K. ISSN 1754-5692.
- Brydson, J. A. (1999). "Furan Resins". In J. A. Brydson (ed.). Plastics Materials (Seventh Edition). Oxford: Butterworth-Heinemann. pp. 810–813. doi:10.1016/B978-075064132-6/50069-3. ISBN 9780750641326.
- MUNJAL, N. L. (May 1970). "Ignition catalysts for furfuryl alcohol - Red fuming nitric acid bipropellant". AIAA Journal. 8 (5): 980–981. doi:10.2514/3.5816.
- Madsen, Peter. "Spectra-testen". Retrieved September 10, 2012.
- "Archived copy" (PDF). Archived from the original (PDF) on 2013-03-17. Retrieved 2013-05-01.CS1 maint: Archived copy as title (link) The Spectra engine test report pdf
- Alfred J., Stamm (1977). "Chapter 9". Wood Technology: Chemical Aspects. ACS Symposium Series. 43. Washington: American Chemical Society. pp. 141–149. doi:10.1021/bk-1977-0043.ch009. ISBN 9780841203730.
- Baysal, Ergun; Ozaki, S.Kiyoka; Yalinkilic, MustafaKemal (21 August 2004). "Dimensional stabilization of wood treated with furfuryl alcohol catalysed by borates". Wood Science and Technology. doi:10.1007/s00226-004-0248-2.