|Preferred IUPAC name
3D model (JSmol)
|Molar mass||98.10 g/mol|
|Appearance||colorless to amber liquid|
|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, also called 2-furylmethanol or 2-furancarbinol, is an organic compound containing a furan substituted with a hydroxymethyl group. It is a clear colorless liquid when pure, but becomes amber colored upon prolonged standing. 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. Upon treatment with acids, heat and/or catalysts, furfuryl alcohol can be made to polymerize into a resin, poly(furfuryl alcohol).
Furfuryl alcohol is manufactured industrially from 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 is produced either by the direct reduction of furfural, or by its disproportionation via the Cannizaro reaction in an aqueous NaOH solution; this latter route also produces furoic acid.
The primary use of furfuryl alcohol is as a monomer for the synthesis of furan resins. These are used in thermoset polymer matrix composites, cements, adhesives, coatings and casting/foundry resins. Synthesis involves acid-catalyzed polycondensation, usually giving a black cross-linked product. A simplified example is shown below but the actual reaction mechanism is known to be exceedingly complex.
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 or formic acid, or borates.
- Furfurylamine - corresponding amine
- 2-Furonitrile - corresponding nitrile
- Furan-2-ylmethanethiol - corresponding thiol
- 2-Furoic acid - corresponding carboxylic acid
- 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. National Institute for Occupational Safety and Health (NIOSH).
- 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. ISSN 1754-5692. doi:10.1039/C5EE02666K.
- 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.
- 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.
- http://copenhagensuborbitals.com/public/spectra.pdf The Spectra engine test report pdf
- Alfred J., Stamm (1977). "Chapter 9". Wood Technology: Chemical Aspects. Washington: American Chemical Society. pp. 141–149. 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.