Tetrahydrofurfuryl alcohol

Chemical properties

Tetrahydrofurfuryl alcohol is a colorless to light yellow hygroscopic liquid that has a faint, warm, oily, caramellic odor with a coffee and nut-like flavor at very low levels (0.03 to 1 ppm). Miscible with water, ethanol, ether, acetone, chloroform and benzene, insoluble in paraffin hydrocarbons. It has an extensive history of use as a highly versatile, high purity solvent.

Occurrence

Reported found in shoyu (fermented soya hydrolysate), coffee and fresh mango.

The Uses of Tetrahydrofurfuryl alcohol

Tetrahydrofurfuryl alcohol is used extensively in various industries as a high-purity, water miscible solvent, and as a chemical intermediate. It was used as Solvent for vinyl resins; dyes for leather; chlorinated rubber; cellulose esters; solvent softener for nylon; vegetable oils; coupling agent; organic synthesis.

Preparation

Tetrahydrofurfuryl alcohol is produced by catalytic reduction of furfural with Raney-Ni; also by destructive hydrogenation of lignin.

Definition

ChEBI: Tetrahydrofurfuryl alcohol is a primary alcohol that is methanol in which one of the hydrogens of the methyl group has been replaced by a tetrahydrofuran-2-yl group. It has a role as a protic solvent. It is a primary alcohol and a member of oxolanes.

What are the applications of Application

Tetrahydrofurfuryl alcohol (THFA) is generally regarded as a "green" solvent in industrial applications. THFA is a low cost, biodegradable solvent mainly used as a reactive diluent for epoxy resins and is a good solvent for many of the curative and catalysts used in epoxy formulations. It is also used in the following applications:
Tetrahydrofurfuryl alcohol undergoes chemoselective hydrogenolysis catalyzed by Rh/SiO2 modified with ReOx species to yield 1,5-pentanediol. It undergoes lanthanum-mediated Michael-type addition reaction with maleate to form alkoxybutanedioic acid.
Tetrahydrofurfuryl alcohol was used as refractive-index matching solvent to ensure hard sphere suspension of silica particles for rheological measurements.
Tetrahydrofurfuryl alcohol may be used as an analytical reference standard for the quantification of the analyte in rats and smoke flavoring from rice husk using chromatography techniques.

General Description

Tetrahydrofurfuryl alcohol appears as a clear colorless liquid with a mild odor. Vapors are heavier than air.

Air & Water Reactions

Denser than water and soluble in water.

Reactivity Profile

Acetyl bromide reacts violently with alcohols or water [Merck 11th ed. 1989]. Mixtures of alcohols with concentrated sulfuric acid and strong hydrogen peroxide can cause explosions. Example: An explosion will occur if dimethylbenzylcarbinol is added to 90% hydrogen peroxide then acidified with concentrated sulfuric acid. Mixtures of ethyl alcohol with concentrated hydrogen peroxide form powerful explosives. Mixtures of hydrogen peroxide and 1-phenyl-2-methyl propyl alcohol tend to explode if acidified with 70% sulfuric acid [Chem. Eng. News 45(43):73. 1967; J, Org. Chem. 28:1893. 1963]. Alkyl hypochlorites are violently explosive. They are readily obtained by reacting hypochlorous acid and alcohols either in aqueous solution or mixed aqueous- carbon tetrachloride solutions. Chlorine plus alcohols would similarly yield alkyl hypochlorites. They decompose in the cold and explode on exposure to sunlight or heat. Tertiary hypochlorites are less unstable than secondary or primary hypochlorites [NFPA 491 M 1991]. Base-catalysed reactions of isocyanates with alcohols should be carried out in inert solvents. Such reactions in the absence of solvents often occur with explosive violence [Wischmeyer 1969].

Health Hazard

Inhalation or contact with material may irritate or burn skin and eyes. Fire may produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.

Flammability and Explosibility

Not classified

Carcinogenicity

Tetrahydro-2-furanmethanol was not mutagenic to S. typhimurium strains TA100, TA1535, TA1537, or TA98 in an in vitro gene mutation assay or to E. coliWP2uvrA/pKM101 with or withoutmetabolic activation. No chromosomal aberrations or polypoidy were observed when tetrahydro-2-furanmethanol was added to cultured Chinese hamster lung cells with or without metabolic activation .