Tetrahydrofurfuryl alcohol

Tetrahydrofurfuryl alcohol Basic information
Product Name:Tetrahydrofurfuryl alcohol
Synonyms:TETRAHYDROFURFURYL ALCOHOL FCC;tetrahydro-2-furylmethanol tetrahydrofurfuryl alcohol;2-Oxolanemethanol;Tetrahydrofuran-2-methanol;Tetrahydrofurfuryl a;Tetrahydrofurfuryl alcohol, 98% 1LT;Tetrahydro furfuryl alcoh;NSC 15434
CAS:97-99-4
MF:C5H10O2
MW:102.13
EINECS:202-625-6
Product Categories:Pharmaceutical intermediates;fine chemical;Solvent for fats, waxes, resins, in organic synthesis.;Building Blocks;C4 to C7;Chemical Synthesis;Heterocyclic Building Blocks;Furan&Benzofuran;Furans
Mol File:97-99-4.mol
Tetrahydrofurfuryl alcohol Structure
Tetrahydrofurfuryl alcohol Chemical Properties
Melting point -80 °C (lit.)
Boiling point 178 °C (lit.)
density 1.054 g/mL at 25 °C (lit.)
vapor density 3.52 (vs air)
vapor pressure 2.3 mm Hg ( 39 °C)
refractive index n20/D 1.452(lit.)
FEMA 3056 | TETRAHYDROFURFURYL ALCOHOL
Fp 183 °F
storage temp. Store below +30°C.
solubility acetone: miscible(lit.)
form Liquid
pka14.44±0.10(Predicted)
color Clear
Odorat 100.00 %. vegetable cauliflower faint warm oily caramel
Odor Typevegetable
explosive limit1.5-9.7%(V)
Water Solubility soluble
Sensitive Hygroscopic
Merck 14,9213
JECFA Number1443
BRN 102723
InChIKeyBSYVTEYKTMYBMK-UHFFFAOYSA-N
LogP-0.14 at 24.7℃
CAS DataBase Reference97-99-4(CAS DataBase Reference)
NIST Chemistry Reference2-Furanmethanol, tetrahydro-(97-99-4)
EPA Substance Registry SystemTetrahydrofurfuryl alcohol (97-99-4)
Safety Information
Hazard Codes Xi,T
Risk Statements 36-62-61
Safety Statements 39-36/37/39
RIDADR NA 1993 / PGIII
WGK Germany 2
RTECS LU2450000
Autoignition Temperature282 °C
TSCA Yes
HS Code 29321300
Hazardous Substances Data97-99-4(Hazardous Substances Data)
ToxicityLD50 orally in Rabbit: 1600 mg/kg
MSDS Information
ProviderLanguage
THFA English
SigmaAldrich English
ACROS English
ALFA English
Tetrahydrofurfuryl alcohol Usage And Synthesis
Chemical PropertiesTetrahydrofurfuryl 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.
OccurrenceReported found in shoyu (fermented soya hydrolysate), coffee and fresh mango.
UsesTetrahydrofurfuryl 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.
ApplicationTetrahydrofurfuryl 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.
PreparationTetrahydrofurfuryl alcohol is produced by catalytic reduction of furfural with Raney-Ni; also by destructive hydrogenation of lignin.
DefinitionChEBI: 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.
General DescriptionTetrahydrofurfuryl alcohol appears as a clear colorless liquid with a mild odor. Vapors are heavier than air.
Air & Water ReactionsDenser than water and soluble in water.
Reactivity ProfileAcetyl 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 HazardInhalation 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 ExplosibilityNotclassified
CarcinogenicityTetrahydro-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 .
D-RIBULOSE DL-ISOCITRIC ACID LACTONE TETRAHYDROFURFURYL ALCOHOL POLYETHYLENEGLYCOL ETHER DIACETONE-D-GLUCOSE Tetrahydro FURFURYL ALCOHOL RESIN Span 20 D-GLUCOHEPTONO-1,4-LACTONE 1,2:3,5-Di-O-isopropylidene-alpha-D-xylofuranose tetrahydrofurfuryl alcohol propionate METHYL TETRAHYDROFURFURYL ETHER D-RIBOFURANOSE-5-PHOSPHORIC ACID SODIUM SALT cis-1,2,3,6-Tetrahydrophthalic anhydride TETRAHYDROFURFURYL RICINOLEATE TETRAHYDROFURAN-2,3,4,5-TETRACARBOXYLIC ACID Glycofurol, Tetrahydrofurfuryl alcohol polyethyleneglycol ether,TETRAHYDROFURFURYL ALCOHOL POLYETHYLENEGLYCOL ETHER 1,2-O-ISOPROPYLIDENE-BETA-L-IDOFURANOSE D-SACCHARIC ACID 1,4-LACTONE Tetrahydrofurfuryl

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