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2-Furanmethanol (furfuryl alcohol) is an organic compound containing a furan substituted with a hydroxymethyl group.
2-Furanmethanol (furfuryl alcohol) is a colorless liquid, but aged samples appear amber.
2-Furanmethanol (furfuryl alcohol) possesses a faint odor of burning and a bitter taste.
CAS: 98-00-0
MF: C5H6O2
MW: 98.1
EINECS: 202-626-1
Synonyms
(2-furyl)-methano;2-furanemethanol;2-Furanmethanol (furfuryl alcohol);2-Furanylmethanol;2-Furfurylalkohol;2-furfurylalkohol(czech);2-Hydroxymethyklfuran;2-hydroxymethylfurane
2-Furanmethanol (furfuryl alcohol) is miscible with but unstable in water.
2-Furanmethanol (furfuryl alcohol) is soluble in common organic solvents.
2-Furanmethanol (furfuryl alcohol) is a colorless to amber liquidthat darkens on exposure to light.
2-Furanmethanol (furfuryl alcohol) has a faint, burningodor.
Molecular weight=98.11; Specific gravityFurfuryl alcohol 1371(H2O:1)=1.13; Boiling point: 171℃; Melting point:215℃; Vapor pressure=6 mmHg at 25℃; Flash point =65℃ (cc); 75℃ (oc); Autoignition temperature=491℃.
Explosive limits: LEL=1.8%; UEL=16.3%. HazardIdentification (based on NFPA-704 M Rating System):Health 1, Flammability 2, Reactivity 1. Soluble in water.
A member of the class of furans bearing a hydroxymethyl substituent at the 2-position.
A clear colorless liquid.
Flash point 167°F.
Boiling point 171°F.
Denser than water.
Contact may irritate skin, eyes and mucous membranes.
May be toxic by ingestion and skin contact and moderately toxic by inhalation.
2-Furanmethanol (furfuryl alcohol) Chemical Properties
Melting point: -29 °C (lit.)
Boiling point: 70 °C (lit.)
Density: 1.135 g/mL at 25 °C (lit.)
Vapor density: 3.4 (vs air)
Vapor pressure: 0.5 mm Hg ( 20 °C)
Refractive index: n20/D 1.486(lit.)
FEMA: 2491 | FURFURYL ALCOHOL
Fp: 149 °F
Storage temp.: Store below +30°C.
Solubility alcohol: soluble
Form: Liquid
pka: 14.02±0.10(Predicted)
Color: Clear yellow
PH: 6 (300g/l, H2O, 20℃)
Odor: Mildly irritating. Very mild, warm-oily, “burnt” odor.
Biological source: synthetic
Odor Threshold: 8 ppm
Odor Type: bready
Explosive limit: 1.8-16.3%(V)
Water Solubility: MISCIBLE
FreezingPoint: -29℃
Merck: 14,4305
JECFA Number: 451
BRN: 106291
Exposure limits NIOSH REL: TWA 10 ppm (40 mg/m3), STEL 15 ppm (60 mg/m3), IDLH 75 ppm; OSHA PEL: TWA 50 ppm; ACGIH TLV: TWA 10 ppm, STEL 15 ppm (adopted).
LogP: 0.3 at 25℃
Surface tension: 39.6mN/m at 293.15K
CAS DataBase Reference: 98-00-0(CAS DataBase Reference)
NIST Chemistry Reference: 2-Furanmethanol (furfuryl alcohol)(98-00-0)
IARC: 2B (Vol. 119) 2019
EPA Substance Registry System: 2-Furanmethanol (furfuryl alcohol) (98-00-0)
2-Furanmethanol (furfuryl alcohol) is a colorless to amber liquid that darkens on exposure to light.
2-Furanmethanol (furfuryl alcohol) has a faint, burning odor.
2-Furanmethanol (furfuryl alcohol) has a very mild, warm, oily, “burnt” odor and a cooked sugar taste.
Clear, colorless to pale yellow liquid with an irritating odor.
Darkens to yellowish-brown on exposure to air.
A detection odor threshold concentration of 32 mg/m3 (8.0 ppmv) was determined by Jacobson et al.
Synthesis
2-Furanmethanol (furfuryl alcohol) is manufactured industrially by hydrogenation of furfural, which is itself typically produced from waste bio-mass such as corncobs or sugar cane bagasse.
As such 2-Furanmethanol (furfuryl alcohol) may be considered a green chemical.
One-pot systems have been investigated to produce furfuryl alcohol directly from xylose using solid acid catalysts.
Although hardly a pure source of the compound, the Maillard reaction produces 2-Furanmethanol (furfuryl alcohol) (among many others).
Reactions
2-Furanmethanol (furfuryl alcohol) undergoes many reactions including Diels–Alder additions to electrophilic alkenes and alkynes.
Hydroxymethylation gives 1,5-bis(hydroxymethyl)furan.
Hydrolysis gives levulinic acid.
Upon treatment with acids, heat and/or catalysts, 2-Furanmethanol (furfuryl alcohol) can be made to polymerize 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 a phase transfer catalyst also reported.
In the Achmatowicz reaction, also known as the Achmatowicz rearrangement, 2-Furanmethanol (furfuryl alcohol)l is converted to a dihydropyran.
Uses
2-Furanmethanol (furfuryl alcohol) has been obtained by yeast reduction of furfural.
2-Furanmethanol (furfuryl alcohol) is used as solvent and in the manufacturing of wetting agents, resins.
Resins, composites
The primary use of furfuryl alcohol is as a monomer for the synthesis of furan resins.
These polymers are used in thermoset polymer matrix composites, cements, adhesives, coatings and casting/foundry resins.
Polymerization involves an acid-catalyzed polycondensation, usually giving a black cross-linked product.
A highly simplified representation is shown below.
Because of its low molecular weight, 2-Furanmethanol (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.
Rocket fuel
2-Furanmethanol (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.
The use of hypergolics avoids the need for an igniter.
Mixtures of furfuryl alcohol and aniline in different proportions were used in American MGM-5 Corporal ballistic missile and WAC Corporal and Aerobee sounding rockets.
Mixture of 41% of furfuryl alcohol, 41% of xylidine and 18% of methanol, called Furaline, was used in France for experimental rocket engines for aircraft, developed by SEPR.
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.
Preparation
Usually prepared from 2-Furanmethanol (furfuryl alcohol) that is obtained by the processing of corncobs; oil obtained by steam distillation of roasted coffee bean meal consists of 50% furfuryl alcohol; prepared industrially by the catalytic reduction of furfural using nickel and Cu-CrO catalysts.
