| Identification | More | [Name]
Tetrahydrofuran | [CAS]
109-99-9 | [Synonyms]
ALPHA-HYDRO-OMEGA-HYDROXYPOLY(OXY-1,4-BUTANEDIYL)
POLY(1,4-BUTANEDIOL)
POLY(1,4-OXYBUTYLENE) GLYCOL
POLYETETRAHYDROFURAN, LINEAR-CHAIN POLYMER
POLYLETRAHYDROFURAN, LINEAR CHAIN POLYMER
POLYTETRAHYDROFURAN
POLYTETRAHYDROFURAN 1000
POLYTETRAHYDROFURAN 1000 S
POLYTETRAHYDROFURAN 1400
POLYTETRAHYDROFURAN 1800
POLYTETRAHYDROFURAN 2000
POLYTETRAHYDROFURAN 250
POLYTETRAHYDROFURAN 650 S
POLYTETRAHYDROFURAN, LINEAR-CHAIN POLYMER
POLY(TETRAMETHYLENE ETHER) GLYCOL
POLYTETRAMETHYLENE ETHER GLYCOL 1000
POLYTETRAMETHYLENE ETHER GLYCOL 1000 S
POLYTETRAMETHYLENE ETHER GLYCOL 1400
POLYTETRAMETHYLENE ETHER GLYCOL 1800
POLYTETRAMETHYLENE ETHER GLYCOL 2000 | [EINECS(EC#)]
203-786-5 | [Molecular Formula]
C4H8O | [MDL Number]
MFCD00148879 | [Molecular Weight]
72.11 | [MOL File]
109-99-9.mol |
| Chemical Properties | Back Directory | [Description]
Tetrahydrofuran (THF) is a chemical intermediate used in the manufacture of polymers as well as agricultural, pharmaceutical, and commodity chemicals. Manufacturing activities commonly occur in closed systems or under engineering controls that limit worker exposure and release to the environment. THF is also used as a solvent (e.g., pipe fitting) that may result in more significant exposures when used in confined spaces without sufficient ventilation. Although THF is naturally present in coffee aroma, floured chickpeas, and cooked chicken, natural exposures are not anticipated to pose a significant hazard. | [Appearance]
Tetrahydrofuran is a colorless liquid. Ethereal odor. The Odor Threshold is listed @ 3.8 (3M), 20-50 ppm, and 31 ppm. | [Melting point ]
-108°C | [Boiling point ]
66 °C | [density ]
0.887 g/mL at 20 °C | [vapor density ]
2.5 (vs air)
| [vapor pressure ]
<0.01 mm Hg ( 25 °C)
| [refractive index ]
n20/D 1.465
| [Fp ]
>230 °F
| [storage temp. ]
2-8°C
| [solubility ]
water: soluble | [form ]
Liquid | [color ]
<10(APHA)
| [Specific Gravity]
0.89 | [Odor]
Ethereal, detectable at 2 to 50 ppm | [PH]
7-8 (200g/l, H2O, 20℃) | [PH Range]
7 | [Relative polarity]
0.207 | [Stability:]
Stable. Incompatible with halogens, strong oxidizing agents, strong reducing agents, strong bases, oxygen. May generate explosive peroxides in storage if in contact with air. Highly flammable. Store at room temperature under nitrogen. Hazardous polymerisation may occur. Light sensitive. May contain 2,6-di-tertbutyl-4-methylphenol (BHT) as a s | [explosive limit]
1.5-12.4%(V) | [Water Solubility ]
miscible | [FreezingPoint ]
-108℃ | [Sensitive ]
Air Sensitive & Hygroscopic | [λmax]
λ: 245 nm Amax: ≤0.26
λ: 275 nm Amax: ≤0.046
λ: 315 μm Amax: ≤0.0044 | [Detection Methods]
GC | [Merck ]
14,9211 | [BRN ]
102391 | [Henry's Law Constant]
1.54 (static headspace-GC, Welke et al., 1998) | [Dielectric constant]
11.6（-70℃） | [Exposure limits]
TLV-TWA 200 ppm (590 mg/m3) (ACGIH,
MSHA, and OSHA); STEL 250 ppm
(ACGIH); IDLH 20,000 ppm (NIOSH). | [InChIKey]
WYURNTSHIVDZCO-UHFFFAOYSA-N | [LogP]
0.45 at 25℃ | [Uses]
Tetrahydrofuran is used primarily (80%) to make polytetramethylene ether glycol, the base polymer used primarily in the manufacture of elastomeric fibers (e.g., spandex) as well as polyurethane and polyester elastomers (e.g., artificial leather, skateboard wheels). The remainder (20%) is used in solvent applications (e.g., pipe cements, adhesives, printing inks, and magnetic tape) and as a reaction solvent in chemical and pharmaceutical syntheses. | [CAS DataBase Reference]
109-99-9(CAS DataBase Reference) | [IARC]
2B (Vol. 119) 2019 | [NIST Chemistry Reference]
Furan, tetrahydro-(109-99-9) | [Storage Precautions]
Moisture sensitive;Light sensitive | [EPA Substance Registry System]
109-99-9(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,F,Xn | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R36/37:Irritating to eyes and respiratory system .
R19:May form explosive peroxides.
R11:Highly Flammable. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S33:Take precautionary measures against static discharges .
S29:Do not empty into drains .
S16:Keep away from sources of ignition-No smoking . | [RIDADR ]
UN 2924 3/PG 2 | [WGK Germany ]
1 | [RTECS ]
MD0916000 | [F ]
3-10-23 | [Autoignition Temperature]
610 °F | [TSCA ]
Yes | [HazardClass ]
3 | [PackingGroup ]
II | [HS Code ]
29321100 | [Safety Profile]
Moderately toxic by ingestion and intraperitoneal routes. Mildly toxic by inhalation. Human systemic effects by inhalation: general anesthesia. Mutation data reported. Irritant to eyes and mucous membranes. Narcotic in high concentrations. Reported as causing injury to liver and kidneys. Flammable liquid. A very dangerous fire hazard when exposed to heat, flames, oxidizers. Explosive in the form of vapor when exposed to heat or flame. In common with ethers, unstabilized tetrahydrofuran forms thermally explosive peroxides on exposure to air. Stored THF must always be tested for peroxide prior to distdlation. Peroxides can be removed by treatment with strong ferrous sulfate solution made slightly acidic with sodium bisulfate. Caustic alkalies deplete the inhibitor in THF and may subsequently cause an explosive reaction. Explosive reaction with KOH, NaAlH2, NaOH, sodium tetrahydroaluminate. Reacts with 2-aminophenol + potassium dioxide to form an explosive product. Reacts with lithium tetrahydroaluminate or borane to form explosive hydrogen gas. Violent reaction with metal halides (e.g., hafnium tetrachloride, titanium tetrachloride, zirconium tetrachloride). Vigorous reaction with bromine, calcium hydride + heat. Can react with oxidizing materials. To fight fire, use foam, dry chemical, COa. When heated to decomposition it emits acrid smoke and irritating fumes. See also 2TETRAHYDROFURYL HYDROPEROXIDE | [Hazardous Substances Data]
109-99-9(Hazardous Substances Data) | [Toxicity]
LD50 oral (rat) 2880 mg/kg
LC50 inhal (rat) 21,000 ppm (3 h)
PEL (OSHA) 200 ppm (590 mg/m3)
TLV-TWA (ACGIH) 200 ppm (590 mg/m3)
STEL (ACGIH) 250 ppm (737 mg/m3) | [IDLA]
2,000 ppm [10% LEL] |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
Hydrogen-->Nickel-->Gamma Butyrolactone-->1,4-Butanediol-->Polychloroprene-->2-chloro-1,3-butadiene-->Metallic oxides-->PALLADIUM-CATALYSTS-->cis-1,4-Dichloro-2-butene-->IRISH MOSS | [Preparation Products]
N-(2-Aminoethyl)piperidine-->Cyclopropylacetic acid-->2,3-Difluorophenylboronic acid-->3-Cyanophenylboronic acid-->(4-AMINO-PYRIDIN-3-YL)-METHANOL-->BENZO[B]THIOPHENE-2-CARBOXALDEHYDE-->(S)-(-)-α,α-Diphenyl-2-pyrrolidinemethanol-->L-Tryptophanol-->2,3,4-Tribromothiophene-->2-(4-tert-Butylphenyl)ethanol-->3-tert-butyl-1H-1,2,4-triazole-5-thiol-->Erythromycin ethylsuccinate-->L(+)-Leucinol-->2-Chloroisonicotinaldehyde-->4-TERT-BUTYLBENZYL ALCOHOL-->Dioctyl(maleate)tin-->Chiral 2，2-Disubstituted thiaprolinol derivatives-->1,4-Butane sultone-->2,2'-DIPYRIDYLAMINE-->Benzyldimethylhexadecylammonium chloride-->4-Amino-5-bromo-2-chloropyrimidine-->SODIUM PHENOLATE TRIHYDRATE-->1-(2-NAPHTHYL)METHANAMINE-->Vinylferrocene-->(R)-TERT-LEUCINOL-->(1,5-DIMETHYL-1H-PYRAZOL-3-YL)METHANOL-->9-Anthracenemethanol-->7-Fluoroindole-->(S)-(-)-4-tert-Butyloxazolidine-2,5-dione-->TERT-BUTYLMAGNESIUM CHLORIDE-->2,5-Dimethylpiperazine-->Allylmagnesium chloride-->Norethindrone-->Levonorgestrel-->4-Chlorobutylbenzoate-->Quinestrol-->Jiuma plate amino-acid surfactant-->1,4-Diiodobutane-->N-methylaminoethanol sodium phosphate-->Tetrahydrothiophene |
| Hazard Information | Back Directory | [General Description]
A clear colorless liquid with an ethereal odor. Less dense than water. Flash point 6°F. Vapors are heavier than air. | [Reactivity Profile]
TETRAHYDROFURAN(109-99-9) reacts violently with oxidizing agents leading to fires and explosions [Handling Chemicals Safely 1980. p. 891]. Subject to peroxidation in the air. Peroxides or their products react exothermically with lithium aluminum hydride [MCA Guide for Safety 1973]. Thus, use as a solvent for lithium aluminum hydride has led to fires. Using potassium hydroxide or sodium hydroxide to dry impure TETRAHYDROFURAN(109-99-9) that contains peroxides has resulted in explosions. A violent explosion occurred during the preparation of sodium aluminum hydride from sodium and aluminum in a medium of TETRAHYDROFURAN(109-99-9) [Chem. Eng. News 39(40):57. 1961]. THF forms explosive products with 2-aminophenol [Lewis 3227]. | [Air & Water Reactions]
Highly flammable. Oxidizes readily in air to form unstable peroxides that may explode spontaneously [Bretherick, 1979 p.151-154, 164]. Soluble in water. | [Health Hazard]
Vapors cause nausea, dizziness, headache, and anesthesia. Liquid can de-fat the skin and cause irritation. Liquid also irritates eyes. | [Potential Exposure]
The primary use of tetrahydrofuran is as a solvent to dissolve synthetic resins, particularly polyvinyl chloride and vinylidene chloride copolymers. It is also used to cast polyvinyl chloride films, to coat substrates with vinyl and vinylidene chloride; and to solubilize adhesives based on or containing polyvinyl chloride resins. A second large market for THF is as an electrolytic solvent in the Grignard reaction-based production of tetramethyl lead. THF is used as an intermediate in the production of polytetramethylene glycol. | [First aid]
If this chemical gets into the eyes, remove any contact lenses at once and irrigate immediately for at least 15 minutes, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts the skin, remove contaminated clothing and wash immediately with soap and water. Seek medical attention immediately. If this chemical has been inhaled, remove from exposure, begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR if heart action has stopped. Transfer promptly to a medical facility. When this chemical has been swallowed, get medical attention. Give large quantities of water and induce vomiting. Do not make an unconscious person vomit. | [Shipping]
UN2056 Tetrahydrofuran, Hazard Class: 3; Labels: 3-Flammable liquid. | [Incompatibilities]
Forms thermally explosive peroxides in air on standing (in absence of inhibitors). Peroxides can be detonated by heating, friction, or impact. Reacts violently with strong oxidizers, strong bases and some metal halides. Attacks some forms of plastics, rubber and coatings. | [Chemical Properties]
Tetrahydrofuran (THF) is an industrial solvent widely recognized for its unique combination of useful properties. DuPont THF is better than 99.9% pure with a small (0.025-0.040 wt % ) amount of butylated hydroxytoluene (BHT, 4-methyl-2,6-di-tertbutyl phenol) added as an antioxidant. Tetrahydrofuran is a cycloaliphatic ether and is not "photochemically reactive" as defined in Section k of Los Angeles County's Rule 66 (equivalent to Rule 442 of the Southern California Air Pollution Control District). THF has an ethereal odor. The Odor Threshold is listed @ 3.8 (3M), 20-50ppm, and 31ppm. It is also a common laboratory reagent and an intermediate in chemical syntheses of consumer and industrial products such as nutritionals, pharmaceuticals, and insecticides (HSDB, 2011).
| [Waste Disposal]
Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform with EPA regulations governing storage, transportation, treatment, and waste disposal. Concentrated waste containing peroxides-perforation of a container of the waste from a safe distance followed by open burning. | [Physical properties]
Tetrahydrofuran is a clear, colourless liquid with a strong ether-like odour. Odor threshold concentration is 2 ppm (quoted, Amoore and Hautala, 1983). It is highly flammable. Contact of tetrahydrofuran with strong oxidising agents may cause explosions. Tetrahydrofuran may polymerise in the presence of cationic initiators. Contact with lithium–aluminium hydride, with other lithium–aluminium alloys, or with sodium or potassium hydroxide can be hazardous. | [Definition]
ChEBI: A cyclic ether that is butane in which one hydrogen from each methyl group is substituted by an oxygen. | [Flammability and Explosibility]
THF is extremely flammable (NFPA rating = 3), and its vapor can travel a
considerable distance to an ignition source and "flash back." A 5% solution of THF
in water is flammable. THF vapor forms explosive mixtures with air at
concentrations of 2 to 12% (by volume). Carbon dioxide or dry chemical
extinguishers should be used for THF fires.
THF can form shock- and heat-sensitive peroxides, which may explode on
concentration by distillation or evaporation. Always test samples of THF for the
presence of peroxides before distilling or allowing to evaporate. THF should never
be distilled to dryness. | [Chemical Reactivity]
Reactivity with Water No reaction; Reactivity with Common Materials: No data; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: May occur when the product is in contact with strong acids and bases; Inhibitor of Polymerization: No data. | [Industrial uses]
Tetrahydrofuran (THF), the saturated derivative of furan,
when used as a solvent for high molecular weight polyvinyl chloride (PVC), vinyl
chloride copolymers, and polyvinylidene chloride copolymers at ambient
temperatures yields solutions of high solids content. Blends of THF and methyl
ethyl ketone are often used for increased solvency in certain polymer compositions.
Applications for THF polymer solutions include PVC top coatings of automotive
upholstery, audio tape coatings of polyurethane/metal oxides on polyester tape,
polyurethane coatings for fabric finishes, water-vapor barrier film coatings of PVC,
and polyvinylidene chloride copolymers onto cellophane film. Tetrahydrofuran is
an excellent solvent for many inks used for printing on PVC film and on PVC
plastic articles. Polyvinyl chloride pipe welding cements are made by dissolving the
resin in THF solvent. Other adhesive applications include cements for leather,
plastic sheeting, and for molded plastic assemblies. Other uses of THF are as a
chemical intermediate and as a complexing solvent for various inorganic,
organometallic, and organic compounds. These THF complexes are important as
Grignard reagents, catalysts for organic reactions, and in stereo-specific
polymerizations. Tetrahydrofuran is the solvent of choice in many pharmaceutical
reactions and applications. The excellent solvency of THF makes this solvent ideal
for solvent cleaning of polymer manufacturing and processing equipment. | [Carcinogenicity]
THF showed little evidence of mutagenic
activity in a variety of in vitro and in vivo
assays. | [Source]
Leaches from PVC cement used to join tubing (Wang and Bricker, 1979) | [Environmental Fate]
Photolytic. The rate constants for the reaction of tetrahydrofuran and OH radicals in the
atmosphere are 1.67 x 10-11 cm3/molecule?sec at 298 K (Moriarty et al., 2003) and 8.8 x 10-12
cm3/molecule?sec at 300 K (Hendry and Kenley, 1979). Atkinson et al. (1988) reported a rate
constant of 4.875 x 10-15 cm3/molecule?sec for the reaction with NO3 radicals in air. | [storage]
THF should be
used only in areas free of ignition sources, and quantities greater than 1 liter should
be stored in tightly sealed metal containers in areas separate from oxidizers.
Containers of THF should be dated when opened and tested periodically for the
presence of peroxides. | [Purification Methods]
It is obtained commercially by catalytic hydrogenation of furan from pentosan-containing agricultural residues. It was purified by refluxing with, and distilling from LiAlH4 which removes water, peroxides, inhibitors and other impurities [Jaeger et al. J Am Chem Soc 101 717 1979]. Peroxides can also be removed by passage through a column of activated alumina, or by treatment with aqueous ferrous sulfate and sodium bisulfate, followed by solid KOH. In both cases, the solvent is then dried and fractionally distilled from sodium. Lithium wire or vigorously stirred molten potassium have also been used for this purpose. CaH2 has also been used as a drying agent. Several methods are available for obtaining the solvent almost anhydrous. Ware [J Am Chem Soc 83 1296 1961] dried it vigorously with sodium-potassium alloy until a characteristic blue colour was evident in the solvent at Dry-ice/cellosolve temperatures. The solvent is kept in contact with the alloy until distilled for use. Worsfold and Bywater [J Chem Soc 5234 1960], after refluxing and distilling from P2O5 and KOH, in turn, refluxed the solvent with sodium-potassium alloy and fluorenone until the green colour of the disodium salt of fluorenone was well established. [Alternatively, instead of fluorenone, benzophenone, which forms a blue ketyl, can be used.] The tetrahydrofuran was then fractionally distilled, degassed and stored above CaH2. p-Cresol or hydroquinone inhibit peroxide formation. The method described by Coetzee and Chang [Pure Appl Chem 57 633 1985] for 1,4-dioxane also applies here. Distillations should always be done in the presence of a reducing agent, e.g. FeSO4. [Beilstein 17 H 10, 17 I 5, 17 II 15, 17 III/IV 24, 17/1 V 27.] It irritates the skin, eyes and mucous membranes, and the vapour should never be inhaled. It is HIGHLY FLAMMABLE, and the necessary precautions should be taken. Rapid purification: Purification as for diethyl ether. | [Toxicity evaluation]
The principal target organs in rodents receiving repeated
exposures to THF are the central nervous system (CNS),
kidney, and liver. The CNS effects caused by THF are thought
to be mediated via the THF metabolites tetrahydro-2-furanone
and 4-hydroxybutanoic acid. This is consistent with the CNS
effects associated with these metabolites as well as the higher
narcotic potency of THF in mice than in comparably exposed
rats and the shorter half-life of THF in the presence of mouse
versus rat hepatic microsomes. In contrast to the CNS effects,
the male rat kidney tumors and female mouse liver tumors
appear to be induced by the parent compound, not a metabolite.
Lifetime exposures of rodents to tetrahydro-2-furanone,
4-hydroxybutanoic acid, and sodium succinate have not
resulted in treatment-related carcinogenic effects, and a mechanistic
study demonstrated that hepatocellular proliferation in
female mice exposed to THF is actually enhanced by CYP450
inhibition, not decreased as one would predict if proliferation
is mediated by a THF metabolite. The THF database has been
reviewed against potential mode of action (MoA) candidates
including direct DNA reactivity, cytotoxicity followed by
regenerative cell proliferation, excessive accumulation of alpha
2u-globulin, exacerbation of rat chronic progressive
nephropathy (CPN), and nuclear receptor (e.g., constitutive
androstane receptor) activation leading to enzyme induction
and enhanced cell proliferation. While the tumorigenic MoAs
have not been identified, exacerbation of CPN (rat kidney)
and nuclear receptor activation (mouse liver) are currently the
more favored. BothMoAs are thought to involve nongenotoxic
(i.e., threshold) events. CPN has no known counterpart in
humans. |
|
|