PRODUCTS

THF (TETRAHYDROFURANE)

CAS Number: 109-99-9
EINECS: 203-726-8
Chemical formula: C4H8O
DESCRIPTION:

Tetrahydrofuran (THF), or oxolane, is an organic compound with the formula (CH2)4O.
THF (TETRAHYDROFURANE) is classified as heterocyclic compound, specifically a cyclic ether.
THF (TETRAHYDROFURANE) is a colorless, water-miscible organic liquid with low viscosity.
THF (TETRAHYDROFURANE) is mainly used as a precursor to polymers.
Being polar and having a wide liquid range, THF is a versatile solvent.
Tetrahydrofurane (THF), in the form of a colourless fluid with an ether-like odor, is an organic solvent that can be used in the production of enamels and adhesives.
THF (TETRAHYDROFURANE) is normally an intermediate in the production of polyamide, polyester and polyurethane
Backed by wide industry experience and industry understanding, we have statured ourselves as a well renowned supplier of Tetrahydrofurane (THF).
Widely known for their uses in numerous industries, these offered solvents are prepared by our vendors making use of superior quality chemical compounds and equipments.
THF (TETRAHYDROFURANE) is a cyclic ether that is butane in which one hydrogen from each methyl group is substituted by an oxygen.
THF (TETRAHYDROFURANE) is a clear colorless liquid with an ethereal odor.
THF (TETRAHYDROFURANE) is Less dense than water.

CAS Number: 109-99-9
EINECS: 203-726-8
Chemical formula: C4H8O

CHEMICAL AND PHYSICAL PROPERTIES OF THF (TETRAHYDROFURANE):
Chemical formula:   C4H8O
Molar mass:   72.107 g•mol−1
Appearance:   Colorless liquid
Odor:   Ether-like
Density:   0.8876 g/cm3 at 20 °C, liquid
Melting point:   −108.4 °C (−163.1 °F; 164.8 K)
Boiling point:   66 °C (151 °F; 339 K)[4][3]
Solubility in water:   Miscible
Vapor pressure:   132 mmHg (20 °C)[2]
Refractive index (nD):   1.4073 (20 °C) [3]
Viscosity:   0.48 cP at 25 °C
Structure:
Molecular shape:   Envelope
Dipole moment:   1.63 D (gas)
Flash point:   −14 °C (7 °F; 259 K)
PSA: 9.23
XLogP3: 0.7968
Appearance: Colorless etheric transparent liquid
Density: 0.8892 g/cm3 @ Temp: 20 °C
Melting Point: -108.3 °C
Boiling Point: 65 °C @ Press: 760 Torr
Flash Point: −14 °C
Refractive Index: n20/D 1.465
Water Solubility: Easily miscible
Storage Conditions: Treasury ventilation low temperature drying, and oxidants, acid and alkali separate storage
Henry's Law Constant:   1.54
Vapor Pressure: 7.15E-05mmHg at 25°C
Vapor Density: 2.5 (vs air)
Flammability characteristics: Class IB Flammable Liquid: Fl.P. below 73°F and BP at or above 100°F.
Explosive limit: vol% in air: 21.8
Odor: Ether-like odor
Explosive limits:   2–11.8%
Preferred IUPAC name: Oxolane
Systematic IUPAC name:
1,4-Epoxybutane
1-Oxacyclopentane
Molecular Weight:   144.21
Hydrogen Bond Donor Count:   0
Hydrogen Bond Acceptor Count:   2
Rotatable Bond Count:   0
Exact Mass:   144.115029749
Monoisotopic Mass:   144.115029749
Topological Polar Surface Area:   18.5 Å²
Heavy Atom Count:   10
Formal Charge:   0
Complexity.   22.8
Isotope Atom Count:   0
Defined Atom Stereocenter Count:   0
Undefined Atom Stereocenter Count.   0
Defined Bond Stereocenter Count:   0
Undefined Bond Stereocenter Count:   0
Covalently-Bonded Unit Count:   2
Compound Is Canonicalized:   Yes

CAS Number: 109-99-9
EINECS: 203-726-8
Chemical formula: C4H8O

PRODUCTION OF THF (TETRAHYDROFURANE):
About 200,000 tonnes of tetrahydrofuran are produced annually.
The most widely used industrial process involves the acid-catalyzed dehydration of 1,4-butanediol. Ashland/ISP is one of the biggest producers of this chemical route.
The method is similar to the production of diethyl ether from ethanol.
The butanediol is derived from condensation of acetylene with formaldehyde followed by hydrogenation.
DuPont developed a process for producing THF by oxidizing n-butane to crude maleic anhydride, followed by catalytic hydrogenation.

A third major industrial route entails hydroformylation of allyl alcohol followed by hydrogenation to 1,4-butanediol.

Other methods:
THF can also be synthesized by catalytic hydrogenation of furan.
This allows certain sugars to be converted to THF via acid-catalyzed digestion to furfural and decarbonylation to furan, although this method is not widely practiced.
THF is thus derivable from renewable resources.

APPLICATIONS OF THF (TETRAHYDROFURANE):
Polymerization:
In the presence of strong acids, THF converts to a linear polymer called poly(tetramethylene ether) glycol (PTMEG), also known as polytetramethylene oxide (PTMO):

n C4H8O → −(CH2CH2CH2CH2O)n−
This polymer is primarily used to make elastomeric polyurethane fibers like Spandex.

As a solvent:
The other main application of THF is as an industrial solvent for polyvinyl chloride (PVC) and in varnishes.
THF is an aprotic solvent with a dielectric constant of 7.6.
THF is a moderately polar solvent and can dissolve a wide range of nonpolar and polar chemical compounds.
THF is water-miscible and can form solid clathrate hydrate structures with water at low temperatures.

THF has been explored as a miscible co-solvent in aqueous solution to aid in the liquefaction and delignification of plant lignocellulosic biomass for production of renewable platform chemicals and sugars as potential precursors to biofuels.
Aqueous THF augments the hydrolysis of glycans from biomass and dissolves the majority of biomass lignin making it a suitable solvent for biomass pretreatment.

THF is often used in polymer science.
For example, THF can be used to dissolve polymers prior to determining their molecular mass using gel permeation chromatography.
THF dissolves PVC as well, and thus THF is the main ingredient in PVC adhesives.
THF can be used to liquefy old PVC cement and is often used industrially to degrease metal parts.
THF is used as a component in mobile phases for reversed-phase liquid chromatography.
THF has a greater elution strength than methanol or acetonitrile, but is less commonly used than these solvents.

THF is used as a solvent in 3D printing when using PLA plastics.
It can be used to clean clogged 3D printer parts, as well as when finishing prints to remove extruder lines and add a shine to the finished product.
Recently THF is used as co-solvent for lithium metal batteries, helping to stabilize the metal anode.

Laboratory use:
In the laboratory, THF is a popular solvent when its water miscibility is not an issue.
THF is more basic than diethyl ether and forms stronger complexes with Li+, Mg2+, and boranes.
THF is a popular solvent for hydroboration reactions and for organometallic compounds such as organolithium and Grignard reagents.
Thus, while diethyl ether remains the solvent of choice for some reactions (e.g., Grignard reactions), THF fills that role in many others, where strong coordination is desirable and the precise properties of ethereal solvents such as these (alone and in mixtures and at various temperatures) allows fine-tuning modern chemical reactions.

Commercial THF contains substantial water that must be removed for sensitive operations, e.g. those involving organometallic compounds.
Although THF is traditionally dried by distillation from an aggressive desiccant, molecular sieves are superior.

Reaction with hydrogen sulfide:
In the presence of a solid acid catalyst, THF reacts with hydrogen sulfide to give tetrahydrothiophene

Lewis basicity:
THF is a Lewis base that bonds to a variety of Lewis acids such as I2, phenols, triethylaluminum and bis(hexafluoroacetylacetonato)copper(II).
THF has been classified in the ECW model and it has been shown that there is no one order of base strengths.
Many complexes are of the stoichiometry MCl3(THF)3.

Precautions:
THF is a relatively acutely nontoxic solvent, with the median lethal dose (LD50) comparable to that for acetone.
However, chronic exposure is suspected of causing cancer.
Reflecting its remarkable solvent properties, it penetrates the skin, causing rapid dehydration.
THF readily dissolves latex and thus should be handled with nitrile rubber gloves.
It is highly flammable.

RELATED COMPOUNDS:
Tetrahydrofurans:
The tetrahydrofuran ring is found in diverse natural products including lignans, acetogenins, and polyketide natural products
Diverse methodology has been developed for the synthesis of substituted THFs.
Oxolanes:
Tetrahydrofuran is one of the class of pentic cyclic ethers called oxolanes.
There are seven possible structures, namely,
•   Monoxolane, the root of the group, synonymous with tetrahydrofuran
•   1,3-dioxolane
•   1,2-dioxolane
•   1,2,4-trioxolane
•   1,2,3-trioxolane
•   tetroxolane
•   pentoxolane

CAS Number: 109-99-9
EINECS: 203-726-8
Chemical formula: C4H8O

USES OF THF (TETRAHYDROFURANE):
Butylene oxide is used as a fumigant and inadmixture with other compounds.
THF is used to stabilize fuel with respect to color and sludge formation.
Tetrahydrofuran is used as a solvent for resins, vinyls, and high polymers; as a Grignard reaction medium for organometallic,and metal hydride reactions; and in the synthesis of succinic acid and butyrolactone.
Solvent for high polymers, especially polyvinyl chloride.
As reaction medium for Grignard and metal hydride reactions.
In the synthesis of butyrolactone, succinic acid, 1,4-butanediol diacetate.
Solvent in histological techniques.
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.
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.

CAS Number: 109-99-9
EINECS: 203-726-8
Chemical formula: C4H8O

SAFETY INFORMATION ABOUT THF (TETRAHYDROFURANE):

Air & Water Reactions:
THF is Highly flammable.
THF Oxidizes readily in air to form unstable peroxides that may explode spontaneously.
THF is Soluble in water.
Reactivity Profile:
Tetrahydrofuran reacts violently with oxidizing agents leading to fires and explosions
Subject to peroxidation in the air.
Peroxides or their products react exothermically with lithium aluminum hydride
Thus, use as a solvent for lithium aluminum hydride has led to fires.
Using potassium hydroxide or sodium hydroxide to dry impure Tetrahydrofuran 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
THF forms explosive products with 2-aminophenol

Health Hazard:
The toxicity of tetrahydrofuran is of low order in animals and humans.
The target organs are primarily the respiratory system and central nervous system.
THF is an irritant to the upper respiratory tract and eyes.
At high concentrations THF exhibits anesthetic properties similar to those of many lower aliphatic ethers.
Exposure to concentrations above 25,000 ppm in air can cause anesthesiain humans.
Other effects noted were strong respiratory stimulation and fall in blood pressure
Kidney and liver injuries occurred in experimental animals exposed to 3000 ppm for 8 hours/day for20 days
Inhalation of high concentrations of vapors or ingestion of the liquid also causes nausea, vomiting, and severe headache.
The acute oral toxicity is low; the LD50 value in rats is in the range of 2800 mg/kg.
The inhalation LC50value in rats is 21,000 ppm/3 h.
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.
Safety Profile:
THF is Moderately toxic by ingestion and intraperitoneal routes.
THF is Mildly toxic by inhalation.
Human systemic effects by inhalation: general anesthesia.
THF is Irritant to eyes and mucous membranes.
THF is Narcotic in high concentrations.
Reported as causing injury to liver and kidneys.
THF is Flammable liquid.
THF is 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.
THF Reacts with 2-aminophenol + potassium dioxide to form an explosive product.
THF 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.
THF Can react with oxidizing materials.
To fight fire, use foam, dry chemical, COa.
When heated to decomposition THF emits acrid smoke and irritating fumes.
Potential Exposure:
The primary use of tetrahydrofuran is as a solvent to dissolve synthetic resins, particularly polyvinyl chloride and vinylidene chloride copolymers.
THF 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.
Carcinogenicity THF showed little evidence of mutagenic activity in a variety of in vitro and in vivo assays.
Shipping:
Purification Methods:
THF is obtained commercially by catalytic hydrogenation of furan from pentosan-containing agricultural residues.
THF was purified by refluxing with, and distilling from LiAlH4 which removes water, peroxides, inhibitors and other impurities
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.

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.
THF irritates the skin, eyes and mucous membranes, and the vapour should never be inhaled.
THF is HIGHLY FLAMMABLE, and the necessary precautions should be taken.
Rapid purification: Purification as for diethyl ether.
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.

CAS Number: 109-99-9
EINECS: 203-726-8
Chemical formula: C4H8O

SYNONYMS OF THF (TETRAHYDROFURANE):
Depositor-Supplied Synonyms:
tetrahydrofuran THF

THF tetrahydrofuran

tetrahydrofurane THF

THF tetrahydrofurane

tetrahydrofuran tetrahydrofuran

SCHEMBL378197

AKOS015900825
1,4-epoxy-Butane
102391 [Beilstein]
109-99-9 [RN]
203-726-8 [EINECS]
butane α,δ-oxide
Butane α,δ-oxide
butylene oxide
Furan, tetrahydro- [ACD/Index Name]
MFCD00005356 [MDL number]
Oxolane
Tetrahidrofurano [Spanish]
Tetrahydrofuraan [Dutch]
Tetrahydrofuran [ACD/IUPAC Name] [Wiki]
Tetrahydrofuran [German] [ACD/IUPAC Name]
tetrahydrofurane
Tétrahydrofurane [French] [ACD/IUPAC Name]
Tetraidrofurano [Italian]
Τετραϋδροφουράνιο [Modern Greek (1453-)]
Тетрагидрофуран [Russian]
テトラヒドロフラン [Japanese]
تتراهیدروفوران [Persian]
四氢呋喃 [Chinese]
1,4-Diethylene oxide
1,4-epoxybutane
14044-65-6 [RN]
203-726-8MFCD00005356
20665-63-8 [RN]
Butane, 1,4-epoxy-
Butane, α,δ-oxide
Cyclotetramethylene oxide
diethylene oxide
Diethylene oxide 1,4-Epoxybutane
Dynasolve 150 [Trade name]
furanidine
Hydrofuran
oxacyclopentane
STR02306
T5OTJ [WLN]
Tetrahydrofuranne
Tetraidrofurano
THF203-726-8MFCD00005356
WLN: T5OTJ