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Furfuryl alcohol

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Furfuryl alcohol[1]
Structural formula of furfuryl alcohol
Ball-and-stick model of the furfuryl alcohol molecule
Names
Preferred IUPAC name
(Furan-2-yl)methanol
Other names
Furan-2-ylmethanol
Furfuryl alcohol
2-Furanmethanol
2-Furancarbinol
2-(Hydroxymethyl)furan
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.388 Edit this at Wikidata
UNII
  • InChI=1S/C5H6O2/c6-4-5-2-1-3-7-5/h1-3,6H,4H2 checkY
    Key: XPFVYQJUAUNWIW-UHFFFAOYSA-N checkY
  • InChI=1/C5H6O2/c6-4-5-2-1-3-7-5/h1-3,6H,4H2
    Key: XPFVYQJUAUNWIW-UHFFFAOYAV
  • c1cc(oc1)CO
Properties
C5H6O2
Molar mass 98.10 g/mol
Appearance colorless to amber liquid[2]
Odor burning odor[2]
Density 1.128 g/cm3
Melting point −29 °C (−20 °F; 244 K)
Boiling point 170 °C (338 °F; 443 K)
miscible
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
3
2
1
Flash point 65 °C; 149 °F; 338 K [2]
Explosive limits 1.8% - 16.3%[2]
Lethal dose or concentration (LD, LC):
397 ppm (mouse, 6 hr)
85 ppm (rat, 6 hr)
592 ppm (rat, 1 hr)[3]
597 ppm (mouse, 6 hr)[3]
NIOSH (US health exposure limits):
PEL (Permissible)
 TWA 50 ppm (200 mg/m3)[2]
REL (Recommended)
 TWA 10 ppm (40 mg/m3) ST 15 ppm (60 mg/m3) [skin][2]
IDLH (Immediate danger)
 75 ppm[2]
Safety data sheet (SDS) External MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

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).

Synthesis

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.[4]

Applications

Plastics

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.[5]

Other uses

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.[6] 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.[7][8]

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.[9][10]

See also

References

  1. ^ Merck Index, 11th Edition, 4215.
  2. ^ a b c d e f g NIOSH Pocket Guide to Chemical Hazards. "#0298". National Institute for Occupational Safety and Health (NIOSH).
  3. ^ a b "Furfuryl alcohol". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  4. ^ 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.
  5. ^ 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.
  6. ^ 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.
  7. ^ Madsen, Peter. "Spectra-testen". Retrieved September 10, 2012.
  8. ^ http://copenhagensuborbitals.com/public/spectra.pdf The Spectra engine test report pdf
  9. ^ Alfred J., Stamm (1977). "Chapter 9". Wood Technology: Chemical Aspects. Washington: American Chemical Society. pp. 141–149. ISBN 9780841203730.
  10. ^ 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.
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