Furfuryl alcohol

Source: Wikipedia, the free encyclopedia.
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 liquid
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).
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Furfuryl alcohol is an

organic solvents.[4]

Synthesis

Furfuryl alcohol is manufactured industrially by hydrogenation of

sugar cane bagasse. As such furfuryl alcohol may be considered a green chemical.[5] One-pot systems have been investigated to produce furfuryl alcohol directly from xylose using solid acid catalysts.[6]

Reactions

It undergoes many reactions including

phase transfer catalyst also reported.[7] In the Achmatowicz reaction, also known as the Achmatowicz rearrangement, furfuryl alcohol is converted to a dihydropyran
.

Applications

Resins, composites

The primary use of furfuryl alcohol is as a

resins. Polymerization involves an acid-catalyzed polycondensation, usually giving a black cross-linked product.[9]
A highly simplified representation is shown below.

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 (e.g. "Kebony") has improved moisture-dimensional stability, hardness, and decay and insect resistance; catalysts can include zinc chloride, citric, and formic acid, as well as borates.[10][11]

Use as rocket propellant (fuel component)

Furfuryl alcohol has been used in rocketry as a fuel which ignites

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.[13][14]

Safety

The median lethal dose for furfuryl alcohol ranges from 160 to 400 mg/kg (mouse or rabbit, oral).[citation needed]

See also

References

  1. ^ Merck Index, 11th Edition, 4215.
  2. ^ a b c d e f 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. ^
    ISBN 978-3527306732
    .
  5. S2CID 101343477
    .
  6. doi:10.3390/catal10101101
    .
  7. ^ Katole DO, Yadav GD. Process intensification and waste minimization using liquid-liquid-liquid triphase transfer catalysis for the synthesis of 2-((benzyloxy)methyl)furan. Molecular Catalysis 2019;466:112–21. https://doi.org/10.1016/j.mcat.2019.01.004
  8. ISBN 9780750641326
    .
  9. doi:10.1021/ma951522f
    .
  10. ISBN 9780841203730
    .
  11. S2CID 33699990
    .
  12. doi:10.2514/3.5816
    .
  13. ^ Madsen, Peter. "Spectra-testen" (in Danish). Archived from the original on September 12, 2012. Retrieved September 10, 2012.
  14. ^ Madsen, Peter. "Project SPECTRA: Experimental evaluation of a liquid storable propellant" (PDF). Copenhagen Suborbitals. Archived from the original (PDF) on 2013-03-17. Retrieved 2013-05-01.

External links

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