Furfuryl alcohol

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Furfuryl alcohol[1]
Structural formula of furfuryl alcohol
Ball-and-stick model of the furfuryl alcohol molecule
Names
IUPAC name
2-furanmethanol
Other names
2-furancarbinol
Identifiers
98-00-0 YesY
3D model (Jmol) Interactive image
ChEBI CHEBI:207496 YesY
ChEMBL ChEMBL308187 YesY
ChemSpider 7083 YesY
ECHA InfoCard 100.002.388
PubChem 7361
UNII D582054MUH YesY
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
Safety data sheet External MSDS
NFPA 704
Flammability code 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 fuel Health code 3: Short exposure could cause serious temporary or residual injury. E.g., chlorine gas 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 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]
US health exposure limits (NIOSH):
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]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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 burning odor 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 by the catalytic reduction of furfural which is obtained from corncob and sugar cane bagasse. It finds use as a solvent, but is primarily used as an ingredient in the manufacture of various chemical products such as foundry resins, adhesives, and wetting agents.

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.[4] 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.[5][6]

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.[7][8]

References[edit]

  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 and Health. National Institute for Occupational Safety and Health (NIOSH). 
  4. ^ Ignition Catalysts for Furfuryl Alcohol—Red Fuming Nitric Acid Bipropellant AIAA Journal Vol 8, No. 5 Pg 988.
  5. ^ Madsen, Peter. "Spectra-testen". Retrieved September 10, 2012. 
  6. ^ http://copenhagensuborbitals.com/public/spectra.pdf The Spectra engine test report pdf
  7. ^ Stamm, Alfred (June 1, 1977). "Dimensional Stabilization of Wood with Furfuryl Alcohol Resin". Wood Technology: Chemical Aspects. AMERICAN CHEMICAL SOCIETY. pp. 141–149. 
  8. ^ Ergun Baysal et al. (21 Aug 2004). "Dimensional stabilization of wood treated with furfuryl alcohol catalysed by borates". Wood Science & Technology. 38 (6). 

External links[edit]