What is Furfuryl alcohol

Furfuryl alcohol is an organic compound containing furans substituted with hydroxymethyl groups.It is a colorless liquid,but aged samples are amber in color.It has a faint burning smell and a bitter taste.It is miscible with water but unstable in water.It is soluble in common organic solvents.

Synthesis

Furfuryl alcohol is produced industrially by the hydrogenation of furfural,which itself is usually produced from waste biomass such as corncobs or bagasse.Therefore,furfuryl alcohol can be regarded as a green chemical.have investigated a one-pot system for the direct production of furfuryl alcohol from xylose using a solid acid catalyst.

Reaction:

It undergoes many reactions including Diels-Alder addition to electrophilic alkenes and alkynes.Hydroxymethylation affords 1,5-bis(hydroxymethyl)furan.Hydrolysis produces levulinic acid.After treatment with acid, heat and/or catalyst,furfuryl alcohol can be polymerized into a resin,poly(furfuryl alcohol).Hydrogenation of furfuryl alcohol yields hydroxymethyl derivatives of tetrahydrofuran and 1,5-pentanediol.The etherification reaction of furfuryl alcohol with alkyl or aryl halides (such as benzyl chloride) in a liquid-liquid-liquid three-phase system with the help of phase transfer catalysts has also been reported.In the Achmatowicz reaction (also known as the Achmatowicz rearrangement),furfuryl alcohol is converted to dihydropyran. 

Applications:

Resin,composite materials

The main use of furfuryl alcohol is as a monomer for the synthesis of furan resin.These polymers are used in thermosetting polymer-based composites,cements,adhesives,coatings,and casting/casting resins.Polymerization involves acid-catalyzed polycondensation reactions,usually resulting in black crosslinked products.A highly simplified representation is shown.Due to its low molecular weight, furfuryl alcohol can impregnate the wood's cells,where it can polymerize and bind to the wood through heat,radiation and/or catalysts or other reactants.Treated wood (eg 'Kebony') has improved moisture dimensional stability,hardness,decay and insect resistance; catalysts can include zinc chloride, citric and formic acids, and borates.

Use as rocket propellant (fuel component):

Furfuryl alcohol, which has been used as a fuel in rocket technology,spontaneously ignites (immediate and vigorous contact) with white-smoking nitric acid or red-smoking nitric acid oxidizer.The use of a self-igniting type avoids the need for an igniter.In late 2012, Copenhagen Suborbital conducted static tests of the Spectra concept liquid rocket engine,which uses white fuming nitric acid as an oxidizer for furfuryl alcohol fuel.

Security:

The LD50 of furfuryl alcohol ranged from 160 to 400 mg/kg (mice or rabbits,orally).