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Furfuryl alcohol is clear colorless organic liquid having a furan substituted with a hydroxymethyl group.
Furfuryl alcohol is primarily used for the synthesis of furans resins which are used in thermoset polymer matrix composites, cements, adhesive and coatings.
Furfuryl alcohol plays an essential role in the production of foundry sand binder and has long been used to produce cores and molds for metal casting.
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
Other applications include as a fuel and wood treatment.
In industry, Furfuryl alcohol is manufactured through either direct reduction of furfural, or through the disproportionation via the Cannizaro reaction in NaOH solution.
The basic raw materials for its manufacturing are waste vegetable materials such as rice hulls, sugar cane bagasse, oat hulls or corncobs.
Furfural alcohol is a colorless to amber liquidthat darkens on exposure to light.
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.
Furfuryl alcohol is clear colorless organic liquid having a furan substituted with a hydroxymethyl group.
Furfuryl alcohol is primarily used for the synthesis of furans resins which are used in thermoset polymer matrix composites, cements, adhesive and coatings.
Furfuryl alcohol plays an essential role in the production of foundry sand binder and has long been used to produce cores and molds for metal casting.
Other applications include as a fuel and wood treatment.
In industry, Furfuryl alcohol is manufactured through either direct reduction of furfural, or through the disproportionation via the Cannizaro reaction in NaOH solution.
The basic raw materials for its manufacturing are waste vegetable materials such as rice hulls, sugar cane bagasse, oat hulls or corncobs.
Furfuryl alcohol is an organic compound containing a furan substituted with a hydroxymethyl group.
Furfuryl alcohol is a colorless liquid, but aged samples appear amber.
Furfuryl alcohol possesses a faint odor of burning and a bitter taste.
Furfuryl alcohol is miscible with but unstable in water.
Furfuryl alcohol is soluble in common organic solvents.
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:Furfuryl alcohol(98-00-0)
IARC: 2B (Vol. 119) 2019
EPA Substance Registry System: Furfuryl alcohol (98-00-0)
Chemical Reactivity
Reactivity with Water No reaction; Reactivity with Common Materials: No reactions; Stability During Transport: The product darkens and forms water insoluble material on exposure to air or acids.
This reaction is accelerated at elevated temperatures; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.
Uses
Furfuryl alcohol, produced by Silvateam, is a clear colorless organic liquid when pure, but becomes amber upon prolonged exposure to light and air.
Furfuryl alcohol, produced in Argentina, is produced using a catalytic hydrogenation process at high pressure, starting from furfural.
Furfuryl alcohol has a purity of 98.5%.
Furfuryl alcohol reacts with formaldehyde and leads to the formation of resinous condensation products that are widely used in the production of thermosetting resins and is particularly resistant to chemicals and solvents.
Furfuryl alcohol is also used for:
Manufacture of foundry resins, characterized by low viscosity, good mechanical strength at metal melting temperature and low gas emission.
Production of corrosion resistant resins with a very competitive price.
Production of abrasive wheels and adhesives based on urea-formaldehyde resin due to its wetting - dispersant properties.
Production of tetrahydrofurfuryl alcohol (THFA) used as a solvent in the pharmaceutical industry.
Reactions
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, 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, furfuryl alcohol is converted to a dihydropyran.
