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| Names | |
|---|---|
| Preferred IUPAC name (Furan-2-yl)methanol | |
| Other names Furan-2-ylmethanol Furfuryl alcohol 2-Furanmethanol 2-Furancarbinol 2-(Hydroxymethyl)furan | |
| Identifiers | |
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3D model (JSmol) | |
| ChEBI | |
| ChEMBL | |
| ChemSpider |
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| ECHA InfoCard | 100.002.388 |
| UNII | |
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| 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) | |
| Flash point | 65 °C; 149 °F; 338 K[2] |
| Explosive limits | 1.8% - 16.3%[2] |
| Lethal dose or concentration (LD, LC): | |
LC50 (median concentration) | 397 ppm (mouse, 6 hr) 85 ppm (rat, 6 hr) 592 ppm (rat, 1 hr)[3] |
LCLo (lowest published) | 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 theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Furfuryl alcohol is anorganic compound containing afuran substituted with ahydroxymethyl group. It is a colorless liquid, but aged samples appear amber. It possesses a faint odor of burning and a bitter taste. It ismiscible with but unstable in water. It is soluble in commonorganic solvents.[4]
Furfuryl alcohol is manufactured industrially by hydrogenation offurfural, which is itself typically produced from waste bio-mass such ascorncobs orsugar canebagasse. As such furfuryl alcohol may be considered a green chemical.[5] One-pot systems have been investigated to produce furfuryl alcohol directly fromxylose usingsolid acid catalysts.[6]
Although hardly a pure source of the compound, theMaillard reaction produces furfuryl alcohol (among many others).[7]
It undergoes many reactions includingDiels–Alder additions to electrophilic alkenes and alkynes. Hydroxymethylation gives1,5-bis(hydroxymethyl)furan. Hydrolysis giveslevulinic acid. Upon treatment with acids, heat and/orcatalysts, furfuryl alcohol can be made topolymerize into a resin, poly(furfuryl alcohol). Hydrogenation of furfuryl alcohol can proceed to give hydroxymethyl derivative of tetrahydrofuran and 1,5-pentanediol. The etherification reaction of furfuryl alcohol with alkyl or aryl halide (e.g. benzyl chloride) in the liquid-liquid-liquid triphase system with the help of aphase transfer catalyst also reported.[8] In theAchmatowicz reaction, also known as the Achmatowicz rearrangement, furfuryl alcohol is converted to adihydropyran.
The primary use of furfuryl alcohol is as amonomer for the synthesis offuran resins.[4][9] These polymers are used inthermoset polymer matrix composites, cements,adhesives, coatings and casting/foundryresins. Polymerization involves an acid-catalyzed polycondensation, usually giving a black cross-linked product.[10] 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 includezinc chloride,citric, andformic acid, as well as borates.[11][12]
Furfuryl alcohol has been used in rocketry as a fuel which igniteshypergolically (immediately and energetically in contact) withwhite fuming nitric acid orred fuming nitric acid oxidizer.[13] The use of hypergolics avoids the need for anigniter. Mixtures of furfuryl alcohol andaniline in different proportions were used in AmericanMGM-5 Corporal ballistic missile andWAC Corporal andAerobeesounding rockets.[14] Mixture of 41% of furfuryl alcohol, 41% ofxylidine and 18% ofmethanol, called Furaline, was used in France for experimental rocket engines for aircraft, developed bySEPR.[14]
In late 2012, Spectra, a concept liquid rocket engine using white fuming nitric acid as the oxidizer to furfuryl alcohol fuel was static tested byCopenhagen Suborbitals.[15][16]
Themedian lethal dose for furfuryl alcohol ranges from 160 to 400 mg/kg (mouse or rabbit, oral).[citation needed]
| Authority control databases: National |
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