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Furfuryl alcohol

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Title: Furfuryl alcohol  
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Subject: Hydrogenolysis, Rocket fuels, White fuming nitric acid, Société d'Etudes pour la Propulsion par Réaction, Robert Truax
Collection: Alcohol Solvents, Alcohols, Furans, Rocket Fuels
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Furfuryl alcohol

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
 Y
ChEBI  Y
ChEMBL  Y
ChemSpider  Y
Jmol-3D images Image
PubChem
UNII  Y
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
2
3
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]
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]
75 ppm[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 Y  (: Y/N?)

Furfuryl alcohol, also called 2-furylmethanol or 2-furancarbinol, is an 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 fall of 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]

Furfuryl alcohol is probably a BK channel agonist.

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]

Uses

The major use of furfuryl alcohol is in the production of resins for bonding foundry sands for production of cores and molds. The binder system contains furfuryl alcohol in monomer or polymer form.

It was also used for the first Lithium-ion batteries.

References

  1. ^ Merck Index, 11th Edition, 4215.
  2. ^ a b c d e f g "NIOSH Pocket Guide to Chemical Hazards #0298".  
  3. ^ a b "Furfuryl alcohol". Immediately Dangerous to Life and Health.  
  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

  • Health hazards
  • CDC - NIOSH Pocket Guide to Chemical Hazards
  • Literature: K.J. Zeitsch,The Chemistry and Technology of Furfural and its Many By-Products, Elsevier, 2000
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