Tetrahydrofuran = THF = Oxolane
CAS Number: 109-99-9
EC Number: 216-898-4
Molecular Weight: 72.11 G/Mol
Chemical formula: C4H8O
Tetrahydrofuran (THF), or oxolane, is an organic compound with the formula (CH2)4O.
The compound is classified as heterocyclic compound, specifically a cyclic ether.
Tetrahydrofuran is a colorless, water-miscible organic liquid with low viscosity.
Tetrahydrofuran is mainly used as a precursor to polymers.
Being polar and having a wide liquid range, THF is a versatile solvent.
Tetrahydrofuran is a clear colorless liquid with an ethereal odor.
Tetrahydrofuran is used as a polar aprotic solvent and in gel permeation chromatography.
THF tends to form shock sensitive peroxides on storage in air so Tetrahydrofuran often sold inhibited with BHT but is available uninhibited also.
Tetrahydrofuran — CH2CH2CH2CH2O — is a cyclic organic compound known for Tetrahydrofurans solvency and cyclic ether structure.
Tetrahydrofuran is also known as THF, Oxolane, Furan, Butylene oxide, Cyclotetramethylene oxide, Diethylene oxide, and Tetra-methylene oxide.
THF is typically a colorless organic liquid that is both water-miscible and low viscosity.
Because of Tetrahydrofurans polar nature and broad liquid range, THF serves as one of the most useful organic solvents on the market today.
Tetrahydrofuran has an assigned CAS Number of 109-99-9.
Tetrahydrofuran is used to make a variety of products, like plastics and rubbers.
Many people come in contactwith tetrahydrofuran on a regular basis because Tetrahydrofuran is used in common items like adhesives and PVC pipes.
Tetrahydrofuran enters the environment and water through the waste created by manufacturing processes.
Tetrahydrofuran does not break down easily in groundwater and can remain in groundwater at high concentrations.
Tetrahydrofuran has been detected in a small sample of Minnesotadrinking waterat levels below MDH guidance.
Tetrahydrofuran (THF) is a saturated cyclic ether with a potential use as a biofuel.
Tetrahydrofurans combustion studies have been investigated.
Reports suggest that Tetrahydrofuran is a better promoter than 1,3 dioxolane for CO2-hydrate formation.
What is Tetrahydrofuran used for?
Tetrahydrofuran has many industry uses as a solvent including in natural and synthetic resins, high polymers, fat oils, rubber, polymer and protective coating, adhesives, inks, tetramethyl lead, PVC and in the production of nylon and adipic acid.
Tetrahydrofuran is also used as a reaction medium, primarily in the pharmaceutical industry, in processes such as Grignard syntheses or lithium aluminium hydride reductions.
Grignard synthesis examples include butyrolactone and succinic acid.
Tetrahydrofuran is also used as a Grignard reagent in the synthesis of synthetic perfumes, pharmaceuticals, motor fuels and insecticides.
Tetrahydrofuran is a valuable chemical intermediate as Tetrahydrofuran is a precursor to polymers, such as poly (tetramethylene ether) glycol.
The primary use of this polymer is the production of elastomeric polyurethane fibres like Spandex.
Tetrahydrofuran is also an intermediate in the natural gas industry where Tetrahydrofuran is a natural gas odorant.
Other industry uses include in intermediates, processing aids and plasticisers.
Commercial uses of Tetrahydrofuran include in adhesives, paints and coatings and solvents.
Tetrahydrofuran was used as a solvent in the formation of diacetylinic polymers.
Tetrahydrofuran may be used in the following processes:
Formation of butyrolactone (BTL) by green oxidation method.
Aqueous THF solution to modify the polystyrene surface by swelling process.
As a solvent for lignin depolymerization to isolate phenolic monomer.
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.
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.
Due to the strong solubility of vinyl chloride, even at a high degree of polymerization, THF is used as a solvent for synthetic leather coatings.
Taking advantage of excellent solubility and diffusion properties, THF is used as a solvent for vinyl and epoxy adhesives.
THF is used for vinyl chloride heat-shrinkable film and for desiccant.
THF is suitable for printing inks, because slightly soluble inorganic compounds can be dissolved and evaporation is quick.
THF is widely used as a solvent for special resins such as photosensitive resins, because even at room temperature Tetrahydrofuran can dissolve various resins, and Tetrahydrofuran is miscible with water and most organic solvents.
In, addition, Tetrahydrofuran is used as a solvent for Grignard and Wittig reactions.
Also in pharmaceutical and agricultural manufacturing, Tetrahydrofuran is used as a solvent for reaction and purification.
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.
Tetrahydrofuran (THF) solvent is an inert, versatile solvent offering high solvency power for numerous organic substances.
Tetrahydrofuran is used as a starting reagent in many syntheses.
Solvent for PVC, polyurethane, polycarbonate, acetate, thermoplastics for adhesives/cements.
Rapid uniformbit into substrates, hogh volatile, solvency, minimize gelling and contributes to bonding strength
coatings & inks application
magnetic recording media - used as solvent for magnetizable oxide and binder for resin for polyester and cellulose acetate tapes
vinyl fabric and sheeting coatings - solvent for high molecular PVC resins
PVC printing inks - use as co-solvent for promote adhesion of inks
coatings and inks features/benefits
provides uniform coating thickness and rapid drying
forms solution with high solids and practical woking viscosities
provides good viscosity and rheology control, reduces smearing
THF is used as an intermediate for Tetrahydrothiopene for odorizing coal gas.
As a solvent
The other main application of THF is as an industrial solvent for polyvinyl chloride (PVC) and in varnishes.
Tetrahydrofuran is an aprotic solvent with a dielectric constant of 7.6.
Tetrahydrofuran 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 Tetrahydrofuran a suitable solvent for biomass pretreatment.
THF is often used in polymer science.
For example, it can be used to dissolve polymers prior to determining their molecular mass using gel permeation chromatography.
THF dissolves PVC as well, and thus Tetrahydrofuran is the main ingredient in PVC adhesives.
THF (Tetrahydrofuran) is a stable compound with relatively low boiling point and excellent solvency.
Tetrahydrofuran is widely-used for dissolution and reaction of various substances.
Also Tetrahydrofuran is used as a starting material for the synthesis of poly(tetramethylene ether) glycol (PTMG), etc.
Since 1982, Mitsubishi Chemical's Yokkaichi plant has produced high-purity, high-quality THF from butadiene using our proprietary technology.
CAS: No. 109-99-9 (T)
EINECS: No. 203-726-8
As a clear liquid, tetrahydrofuran has an ethereal odor and is colorless.
Tetrahydrofuran is highly soluble in water, as well as alcohols, esters, ketones, and ethers.
Tetrahydrofuran has a melting point of -108.5 degrees Celsius and a boiling point of 66 degrees Celsius.
Tetrahydrofuran is highly flammable and has the ability to form explosive peroxides if improperly stored.
Due to Tetrahydrofurans properties as a strong solvent, THF can penetrate the skin — resulting in rapid dehydration.
Tetrahydrofuran can easily dissolve latex, so neoprene or nitrile rubber gloves should be used when handling Tetrahydrofuran.
In addition, THF can cause serious eye and respiratory irritations.
Always employ protective eyewear, respiratory gear, and clothing when working with tetrahydrofuran, and store unused portions of the product in a secure container in a well-ventilated place.
CAS Number: 109-99-9
ECHA InfoCard: 100.003.389
PubChem CID: 8028
RTECS number: LU5950000
CompTox Dashboard (EPA): DTXSID1021328
Tetrahydrofuran 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.
Tetrahydrofuran 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.
Tetrahydrofuran 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.
In the laboratory, THF is a popular solvent when Tetrahydrofurans water miscibility is not an issue.
Tetrahydrofuran is more basic than diethyl ether and forms stronger complexes with Li+, Mg2+, and boranes.
Tetrahydrofuran 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.
Preferred IUPAC name
Systematic IUPAC name
Reaction with hydrogen sulfide
In the presence of a solid acid catalyst, THF reacts with hydrogen sulfide to give tetrahydrothiophene.
THF is a Lewis base that bonds to a variety of Lewis acids such as I2, phenols, triethylaluminum and bis(hexafloroacetylacetonato)copper(II).
THF have been classified in the ECW model and Tetrahydrofuran has been shown that there is no one order of base strengths.
Many complexes are of the stoichiometry MCl3(THF)3.
Chemical formula: C4H8O
Molar mass: 72.107 g·mol−1
Appearance: Colorless liquid
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)
Solubility in water: Miscible
Vapor pressure: 132 mmHg (20 °C)
Refractive index (nD): 1.4073 (20 °C)
Viscosity: 0.48 cP at 25 °C
Tetrahydrofuran (THF) is a colorless, volatile liquid with an ethereal or acetonelike smell and is miscible in water and most organic solvents.
Tetrahydrofuran is highly flammable and may thermally decompose to carbon monoxide and carbon dioxide.
Prolonged storage in contact with air and in the absence of an antioxidant may cause THF to decompose into explosive peroxides.
Tetrahydrofuran is 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.
RCRA waste number U213
Tetrahydrofuran Chemical Properties
Tetrahydrofuran (THF) is an industrial solvent widely recognized for Tetrahydrofurans 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.
THF has an ethereal odor.
The Odor Threshold is listed @ 3.8 (3M), 20-50ppm, and 31ppm.
Tetrahydrofuran is also a common laboratory reagent and an intermediate in chemical syntheses of consumer and industrial products such as nutritionals, pharmaceuticals, and insecticides.
Tetrahydrofuran Physical properties
Tetrahydrofuran is a clear, colourless liquid with a strong ether-like odour.
Odor threshold concentration is 2 ppm.
Tetrahydrofuran 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.
Butylene oxide is used as a fumigant and inadmixture with other compounds.
Tetrahydrofuran is usedto stabilize fuel with respect to color andsludge formation.
Tetrahydrofuran is used as a solvent forresins, vinyls, and high polymers; as a Grignardreaction medium for organometallic,and metal hydride reactions; and in the synthesisof 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.
May be used under Federal Food, Drug & Cosmetic Act for fabrication of articles for packaging, transporting, or storing of foods if residual amount does not exceed 1.5% of the film: Fed. Regist. 27, 3919.
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.
ChEBI: A cyclic ether that is butane in which one hydrogen from each methyl group is substituted by an oxygen.
A clear colorless liquid with an ethereal odor.
Less dense than water.
Flash point 6°F.
Vapors are heavier than air.
CAS Number: 109-99-9
Molecular Weight: 72.11
Beilstein/REAXYS Number: 102391
EC Number: 203-726-8
MDL number: MFCD00005356
PubChem Substance ID: 57649919
Tetrahydrofuran, Spectrophotometric Grade
Tetrahydrofuran, 99.5+%, for spectroscopy
Furan, tetrahydro-, homopolymer
RCRA waste no. U213
Tetrahydrofuran, 99+%, extra pure, stabilized with BHT
Tetrahydrofuran, 99.5%, for analysis, stabilized with BHT
Tetrahydrofuran, 99.6%, ACS reagent, stabilized with BHT
Tetrahydrofuran, mostly called THF or oxolane, is an organic liquid extensively used as solvent and also as a reagent that acts as precursor of polymerization.
Formula and structure: The chemical formula of thetrahydrofuran is (CH2)4O; the structure is a heterocycle formed by 4 CH2- bond to an oxygen atom.
More specifically, Tetrahydrofuran is cyclic ether.
Tetrahydrofuran molecular mass is 72.11 g mol-1.
The structure is a 5 member cycle which is less flexible than a open chain of 5 member but less rigid than a aromatic ring.
The chemical structures can be written as below, in the common representations used for organic molecules.
Occurrence: Tetrahydrofuran is not found in nature.
Preparation: Tetrahydrofuran can be produced through several methodologies, some of them are:
-Catalytic hydrogenation of maleic anhydride or catalytic hydrogenation of furan using a catalyst of nickel or palladium.
-Decarboxylation of furfural to furan using metal catalyst and then, hydrogenation of furan to THF.
-In industry, Tetrahydrofuran is mainly produced through the reaction between acetylene and formaldehyde to form 2-butyne-1,4-diol, which is hydrogenated to the corresponded saturated diol that is cyclized to THF.
Physical properties: Tetrahydrofuran is a colorless, ether-like smell liquid.
Tetrahydrofurans melting point is -108.3 °C and its boiling point is 66 °C.
The density is 0.88 g mL-1.
Tetrahydrofuran is miscible in water and also soluble in organic solvents as ethyl acetate, ethanol, methanol, benzene and acetone.
Tetrahydrofuran is not used in water-sensitive reaction, due to its capacity to absorb water.
Chemical properties: THF is a weak Lewis base, which means, Tetrahydrofuran can donate electrons to chemical species which are lack of electrons (for example, metals/transition metals), and so THF can react with these metals to form complexes and reagents as the Grignard reagent.
One of the disadvantages of THF is that it mostly contains compounds as butylated hydroxytoluene to avoid the formation of explosive peroxide when storage for long periods or in contact with air or light.
Uses: Tetrahydrofuran is used to polymerized the poly(tetramethylene ether) glycol to polytetramethylene oxide, which is a intermediate in the production of fibers as polyurethane.
However, Tetrahydrofurans more common use is as solvent for many industrial processes and also for polymers as PVC.
In laboratory scale is used in a huge number of reactions, for example to prepare the Grignard reagent.
Tetrahydrofuran, 99.85%, Extra Dry, stabilized, AcroSeal(R)
Tetrahydrofuran, 99.85%, Extra Dry, Unstabilized, AcroSeal(R)
Tetrahydrofuran is an organic, polar, water-miscible, cyclic ether and aprotic solvent with low viscosity.
Available in various quantities, purities, and reagent grades, Tetrahydrofuran has applications including use in polymer science and reversed phase chromatography.
Quality Level: 200
vapor density: 2.5 (vs air)
114 mmHg ( 15 °C)
143 mmHg ( 20 °C)
autoignition temp.: 610 °F
expl. lim.: 1.8-11.8 %
≤20 ppm peroxide (as H2O2)
<0.005% water (100 mL pkg)
evapn. residue: <0.0005%
refractive index: n20/D 1.407 (lit.)
bp: 65-67 °C (lit.)
mp: −108 °C (lit.)
solubility: H2O: soluble
density: 0.889 g/mL at 25 °C (lit.)
SMILES string: C1CCOC1
InChI key: WYURNTSHIVDZCO-UHFFFAOYSA-N
THF is used as a solvent in organic synthesis and chromatographic analysis, and is an intermediate of nylon-6,6.
Tetrahydrofuran is also used as an intermediate for synthetic pesticides, e.g., fenbutatin.
Tetrahydrofuran is directly used for synthetic fibers, synthetic resins, synthetic rubber, as well as a solvent for many polymeric materials.
Tetrahydrofuran is widely used as surface coatings, anticorrosion coatings, and printing inks.
In the pharmaceutical industry, THF is used for the synthesis of carbetapentane, rifamycin, progesterone, and some hormone drugs.
Tetrahydrofuran (THF) and 1,2-dimethoxyethane (glyme) are the most commonly used ether solvents in electrochemistry.
They are very inert, especially toward reducing conditions.
They are fairly non-polar (low dielectric constants), which can make dissolving electrolytes and achieving high conductivity in salt solutions in these solvents difficult.
Organic carbonates such as propylene carbonate (PC) and ethylene carbonate (EC), and lactones such as y-butyrolactone are especially good choices for lithium salts such as LiPF6, LiTriflate, and LiTFSI, which are all widely used in lithium battery technology.
They have not been widely used for other applications in electrochemistry but they should be well suited for such applications.
DSSTox_RID_76084Tetrahydrofuran Ultra LC-MS
Tetrahydrofuran, ACS reagent
Tetrahydrofuran, p.a., 99%
Diethylene oxide 1,4-Epoxybutane
Tetrahydrofuran Reagent Grade ACS
Tetrahydrofuran, UV, HPLC Grade
Tetrahydrofuran, analytical standard
Poly(tetramethylene ether glycol) 650
Tetrahydrofuran, (stabilized with BHT)
Tetrahydrofurans are an important class of five-membered oxygen heterocycles often present in a great variety of natural products and synthetic compounds of biological interests.
This type of heterocyclic compounds is widely used in cosmetic formulations, perfumes, and flavors.
Figure 2 enlists mucoxin, a natural product with high potential as specific antitumor agent against breast carcinoma; furans 9a–c are also known possess flavors with insecticidal activity.
Tetrahydrofuran, for HPLC, >=99.9%
Tetrahydrofuran, purum, >=99.0% (GC)
Structure of THF
THF is composed of four carbon atoms, eight hydrogen atoms, and one oxygen atom and Tetrahydrofuran's most importantly characterized as being a heterocyclic ether.
''-Cyclic'' means Tetrahydrofuran's a ring structure, the prefix ''hetero-'' tells us that at least one of the atoms within the ring is something other than carbon (oxygen in this case), and the ''ether'' portion of the name tells us the functional group.
An ether is an organic functional group in which a central oxygen atom is bonded to two carbon-based groups.
What about the ''-furan'' portion of the name tetrahydrofuran?
This tells us that Tetrahydrofuran's a derivative, or cousin, of its parent molecule, furan.
THF only differs in the fact that the double bonds have been removed and replaced with four hydrogen atoms.
Does the term 'tetra' mean anything to you?
That's right, Tetrahydrofuran means four, for the four hydrogen atoms that have been added!
Another important structural aspect of THF is that Tetrahydrofuran's a polar molecule.
Since oxygen is more electronegative than carbon and hydrogen, the oxygen pulls electron density towards itself in the form of the covalent bonds within the ring structure.
As a consequence of its polarity, THF mixes readily with other polar species like water, methanol, ethanol, and acetonitrile, just to name a few.
Formula: C4H8O / (CH2)3CH2O
Molecular mass: 72.1
Boiling point: 66°C
Melting point: -108.5°C
Relative density (water = 1): 0.89
Solubility in water: freely soluble
Vapour pressure, kPa at 20°C: 19.3
Relative vapour density (air = 1): 2.5
Relative density of the vapour/air-mixture at 20°C (air = 1): 1.28
Flash point: -14.5°C c.c.
Auto-ignition temperature: 321°C
Explosive limits, vol% in air: 2-11.8
Octanol/water partition coefficient as log Pow: 0.46 (estimated)
Viscosity: 0.5 mPa*s at 20°C
Tetrahydrofuran is a popular solvent used in the production of a number of pharmaceuticals and fine chemicals, particularly hydroboration reactions and for reactions involving organometallic compounds such as organic lithium and Grignard reagents.
To allow recycle and reuse, water must be removed to a very low level.
Tetrahydrofuran (THF, oxolane) is a versatile solvent used in laboratory organic synthesis and in industrial products such as varnishes.
Tetrahydrofuran is colorless and miscible in water, with a boiling point of 66 ºC.
Tetrahydrofuran is highly flammable but relatively nontoxic.
When stored in air, Tetrahydrofuran can form explosive peroxides, but this can be prevented by adding an inhibitor such as butylated hydroxytoluene (BHT).
Tetrahydrofuran 4THF5 is a cyclic ether with two primary industrial uses.
The major use is as a monomer in the production of polytetramethylene ether glycol 4PTMEG5, a component of cast and thermoplastic urethane elastomers, polyurethane stretch fibers 4spandex5, and high1performance copolyester1polyether elastomers 4COPE5.
A smaller amount of THF is used as a solvent in polyvinyl chloride 4PVC5 cements, pharmaceuticals, and coatings; precision magnetic tape manufacture; and as a reaction solvent.
Chemical and physical properties of tetrahydrofuran:
Molecular Formula: C4H8O / (CH2)4O / (CH2)3CH2O
Synonyms: THF, oxolane, 1,4-epoxybutane, oxacyclopentane, butylene oxide, cyclo tetramethylene oxide.
Cas Number: 109-99-9
Molecular Weight: 72.11 g/mol
Flashpoint: 6 °F / -14.4 °C
Boiling Point: 151 °F at 760 mm Hg
Melting Point: -163.3 °F / -108.5 °C
Water Solubility: miscible
Density: 0.888 at 68 °F
Tetrahydrofuran is a solvent used for making rubber, resins, plastics, dyes, lacquers, spandex, PVC pipe,adhesives, and food storage and packaging materials.
As of 2004, the world produces about 200,000 tons of tetrahydrofuran each year.
Tetrahydrofuran in Minnesota Waters
Since 2004, eight water utilities in Minnesota have detected tetrahydrofuran in the drinking water they supply.
The levelsranged from 0 to 130 parts per billion (ppb).
The Minnesota Pollution Control Agency has detected tetrahydrofuran in monitoring wells at closed landfill sites throughout the state.
When Tetrahydrofuran is detected, concentrations in the last ten years have averaged 292 ppb.
MDH Guidance Value
The US Environmental Protection Agency (EPA) evaluated the health effects of tetrahydrofuran in 2012.
MDH used information from this review and other available information to develop a guidance value of 600 ppb for tetrahydrofuran in drinking water.
A person drinking water at or below the guidance value would have little or no risk of health effects.
Potential Exposure to Tetrahydrofuran
People can be exposed to tetrahydrofuran through the air they breathe, food they eat, water they drink, or through touching products that have tetrahydrofuran in them.
Many people come in contact with tetrahydrofuran on a regular basis because Tetrahydrofuran is used in common items like adhesives and PVC pipes.
People who work somewhere that uses or produces tetrahydrofuran can inhale tetrahydrofuran from the air or get Tetrahydrofuran on their skin.
How is Tetrahydrofuran produced?
Tetrahydrofuran was traditionally produced using the Furfural process where furfural, extracted from corn husks, is used as the raw material in production.
However, the disadvantage of this method is that supply depended on agricultural conditions and could not therefore be relied upon, so a move was made to the fully synthetic Reppe process.
In the Reppe process, ethyne and formaldehyde are used as the raw materials that produce 1,4-butanediol, at the first step.
Tetrahydrofuran can then be obtained via the acid-catalyzed dehydration of 1,4-butanediol in the presence of an acidic ion exchange resin.
This is currently the main method of extraction employed throughout the world.
A second major industrial method of manufacturing THF is the hydroformylation of allyl alcohol followed by the subsequent hydrogenation to resulting in 1,4-butanediol.
Oxidisation of n-butane
Another method is a two-step butadiene chlorination process that yields 70-75% THF.
Developed by DuPont, Tetrahydrofuran involves oxidising n-butane to create maleic anhydride followed by catalytic hydrogenation over a palladium catalyst.
Tetrahydrofuran is a relatively simple process and one that is of interest to chemical producers.
Catalytic hydrogenation of furan
Tetrahydrofuran can also be produced, or synthesised, via catalytic hydrogenation of furan.
This process involves converting certain sugars into THF by digesting to furfural.
An alternative to this method is the catalytic hydrogenation of furan with a nickel catalyst.
Other methods include the decarboxylation of furfural and the oxidisation of butadiene.
The world annual production of tetrahydrofuran is approximately 200,000 tonnes and Tetrahydrofuran is predicted that demand and production will grow as the Chinese economy continues to expand.
Tetrahydrofuran (THF) is a colorless, water-miscible organic liquid with low viscosity.
Acetones and THF odor is very similar.
Tetrahydrofuran is mainly used as a precursor to polymers.
Being polar and having a wide liquid range, THF is a versatile solvent.
There are many applications and uses for tetrahydrofuran (THF).
As an industrial solvent Tetrahydrofuran can be most commonly found in PVC and in varnishes.
Molecular weight: 72.11
Boiling point: 66°C
Vapor pressure: 142 Torr at 20°C
Freezing point: -108.5°C
Refractive index: 1.4072 at 20°C
0.888 g/mL (7.41 lb/gal) at 20°C
0.881 g/mL (7.35 lb/gal) at 25°C
Dielectric constant: 7.58 at 25°C
Dipole moment: 1.75 D at 25°C
Solvent group: 3
Polarity index (P'): 4.0
Eluotropic value on alumina: 0.45
Eluotropic value on octadecylsilane: 3.7
Viscosity: 0.55 cP at 20°C
Surface tension: 26.4 dyn/cm at 25°C
Solubility in water: Miscible in all proportions
Tetrahydrofuran is often used as an additive in reverse phase chromatography, and as a mobile phase for size exclusion chromatography (SEC).
Tetrahydrofuran may be used with an LC/MS detector, but Tetrahydrofurans use should be limited for the following reasons:
1. THF is highly flammable and should be used in combination with an aqueous solvent if possible.
Particular care should be exercised when using THF with APCI due to the presence of a corona (electrical discharge) in the source.
2. THF is an aprotic solvent and cannot donate a proton for ionization.
THF should be paired with a protic mobile phase (i.e. 20-50% water) when possible.
The addition of 0.2% acetic acid, 0.1% formic acid or 10-20 mM NH-4OAc to the mobile phase will assist positive mode ionization.
The addition of 1% chloroform to the mobile phase will assist in negative mode ionization.
3. THF tends to polymerize in APCI mode.
Tetrahydrofuran will cause a loss of sensitivity and fouling of the corona needle.
Tetrahydrofuran will not damage the instrument, but corona needles will have to be replaced or cleaned more often compared with alcohol/water mobile phases.
4. THF attacks PEEK tubing. Because the pressures in the LC/MSD sample path are generally below 10-15 bars, the softening of the PEEK tubing with THF is generally not a problem, particularly if the percentage of THF is kept low.
However, Tetrahydrofuran is possible to replace the PEEK tubing in the LC/MSD sample path with stainless steel tubing by ordering the following part numbers:
-Inlet to selection valve (SSV), 180 mm. Part No. G1313-87304
-SSV to nebulizer, 400 mm. Part No. 01040-87602 (380 mm)
-Manual Injection Valve to SSV, 140 mm. Part No. G1315-87312 (150 mm)*
Average molecular weight is an important property of polymers and is an indication of strength and flexibility.
After use, the waste THF is contaminated with:
Physical State :Liquid
Storage :Store at 4° C
Melting Point :-106° C
Boiling Point :65-66° C
Density :0.99 g/mL at 25° C
CAS No: 109-99-9
Purity %: 99.9%
Packaging Details: 160 Kg Drum
Grade Standard: Industrial Grade
HS Code: 29321100
EC No.: 216-898-4
Physical State: Liquid
Molecular Weight: 72.11 G/Mol
Density: 0. 889 G/Ml
Melting Point: -108.4 Deg C
Boiling Point: 66 Deg C
Solubility in water: more or equall to 100 mg/mL
Vapor pressure: 114 Mm Hg
Shelf Life: 1 years
Refractive index: 1.405
Flash Point: 6 Deg F
Ignition Temperature: 610 Deg f
Surface tension: 26.4 Dynes/Cm
Precautions: Keep Away From Heat
pH Value: 7 to 8
Specific Gravity: 0.888
Chemical Formula: C4h8o
Tetrahydrofuran (THF) is produced by dehydration of 1,4-butanediol.
Tetrahydrofuran is a neutral, colorless, volatile cycloaliphatic ether.
Tetrahydrofuran is highly polar and miscible with water.
As an aprotic and medium polarity solvent, tetrahydrofuran is an excellent solvent for many organic substances.
The chemical formula of this cyclic ether is (CH2)4O.
Tetrahydrofuran analytical grade.
Synonyms: THF, tetrahydrofuran, 1,4-epoxybutane, butylene oxide, cyclotetramethylene oxide, Oxolane, oxacyclopentane, diethylene oxide, furanidine, hydrofuran, tetra-methylene oxide.
Appearance colourless, clear liquid
Assay (GC) min. 99,5 %
Colour max. 20 Hazen
Density (20°C) 0,887 - 0,89 g/cm3
Water max. 0,05 %
Acids (as CH3COOH) max. 0,003 %
Peroxides (as H2O2) max. 0,015 %
Residue on evaporation max. 0,005 %
Tetrahydrofuran (THF) is a contaminant of exposure and appears in human biofluids.
The Food and Drug Administration (FDA) has announced recommendations to revise the permitted daily exposures for THF, and so has the International Conference on Harmonisation. THF oxidizes readily, which can lead to instability and result in cytotoxicity.
Tetrahydrofuran is a colourless low-viscosity liquid with a smell similar to diethyl ether and is one of the most polar ethers.
Tetrahydrofuran is essentially considered in occupational toxicology, and acute poisoning cases are extremely rare.
THF is often used for hydroborations used to synthesize primary alcohols.
THF is often used as a solvent for Grignard reagents because of the oxygen atom's ability to coordinate to the magnesium ion component of the Grignard reagent (an organometallic chemical reaction involving alkyl- or aryl-magnesium halides).
THF is often used in polymer science.
For example, Tetrahydrofuran can be used to dissolve rubber prior to determining Tetrahydrofurans molecular mass using gel permeation chromatography.
THF tends to form peroxides on storage in air.
In sequential deposition method of lead-halide perovskite material, the PbI2 layer morphology and remnant PbI2 play an important role in enhancing the power conversion efficiency (PCE) of the perovskite solar cell.
However, humidity levels affect the PbI2 and perovskite film morphology, resulting in defect sites and recombination centers on the surface and within the bulk of the material, thus impeding the overall device performance and stability.
To address this, incorporation of tetrahydrofuran (THF) additive in PbI2–dimethylformamide (DMF) precursor solution is reported, to improve the quality of PbI2 thin films and to prevent the water interaction directly with PbI2 under high humidity environments.
The O-donor THF interacts with PbI2, resulting in a homogeneous, dense, and pinhole-free layer as compared with the PbI2 layer without additive.
The perovskite layer so obtained from the pinhole-free PbI2 layer is compact, resulting in a significant reduction of defects/traps.
The device is fabricated with modified perovskite in ≈50% humidity atmosphere, resulting in 15% efficiency with high reproducibility.
Moreover, the THF-modified non-encapsulated perovskite device retains 80% PCE after exposure to 50% relative humidity for 20 days.
A strategy to fabricate perovskite solar cells, with reproducible efficiency in high humidity atmosphere viable for large-scale production, is demonstrated.
Tetrahydrofuran (THF) is a versatile chemical that has commercial application as a solvent for the manufacture of plastics and is closely related to 1,4-butanediol (BDO) and γ-butyrolactone (GBL).
Since THF polymers (PolyTHF and PTMEG) are also major commercial products, further investigation into the application of these products will be of great interest, particularly for the potential production of THF from furfural in this co-solvent strategy.
THF owes its excellent solvent properties to the polar oxygen in its ring and dispersive character from the four methylene groups.
In a binary mixture with water, the dispersive character of THF increases with increasing THF content in the aqueous phase.
THF is also an excellent extracting solvent for furfural and 5-hydroxymethylfurfural (HMF), and its affinity for these aldehydes may play a key role in its ability to improve their yields in our single-phase system.
THF can also be used to solubilize extracted lignin products from organosolv or ionic-liquid pretreatment strategies or directly used to fractionate raw biomass as with our single-phase process.
Furfural is typically synthesized by acid-catalyzed dehydration of C5 sugars (arabinoseand xylose) whereas levulinic acid (LA) can be derived from either C529 or C6 sugars1 15 (glucose, galactose, and mannose).
Water-soluble Brønsted acids such as HCl and H2SO4 have typically been used to catalyze such dehydration reactions, but homogeneous and heterogeneous solid acid catalysts have also been applied successfully.
Furfural is targeted in this paper as one of the only natural precursors to furan-based chemicals.
However, Tetrahydrofurans low commercial yields (~50% of theoretical) from xylan-rich lignocellulosic residues23 20 hinder Tetrahydrofurans economic potential, and new approaches are needed to make it economically viable as a fuel precursor.
HMF is an important platform chemical that can be produced from the acid-catalyzed dehydration of hexoses.
HMF will readily hydrolyze to form equimolar amounts of LA and formic acid (FA)1 23 in the presence of
Electronic Supplementary Material (ESI) for Green Chemistry This journal is © The Royal Society of Chemistry 2013 a strong acid.
Since LA is more stable than HMF in an aqueous environment,1 1 higher final yields 2 of LA were observed in single phase reactions with sulfuric acid.
Room temperature liquid densities after the 40 min reactions (0.989 kg L-1 3 with 1:1 THF and 1.015 kg L-1 4 without THF at 21 °C) accounted for a 3% difference in the maximum furfural yield.
For both solvent and non-solvent reactions in Table 1, the highest furfural yield was achieved much sooner (40 min) than the highest LA yield (120 min).
Due to the more acid labile amorphous structure of hemicellulose, the rate of hydrolysis of xylan from hemicellulose was much greater than that of glucan from crystalline cellulose.
By increasing the ratio of THF to 3:1 (density: 0.935 kg L-1 9 ), co-production yields of furfural, HMF, and LA improved with increased solubilisation of biomass without significant furfural losses.
Tetrahydrofuran is a flammable liquid that is also an irritant, and should be treated with care by researchers.
Tetrahydrofuran is also a peroxide forming chemical and care should be taken when handling Tetrahydrofuran as it may become shock sensitive.
Tetrahydrofuran is generally used as a reaction solvent.
This compound should be inspected prior to use for peroxide crystals that may have collected around the cap, on the inside, or on the outside of the bottle.
Tetrahydrofuran is an organic compound of the ether family and C4H8O is Tetrahydrofurans chemical formula.
Tetrahydrofurans appearance is a liquid with low viscosity and colorless, this solvent is compatible with water and can dissolve polar and non-polar compounds.
Tetrahydrofuran has low reactivity and is often used as a solvent in organic reactions.
Tetrahydrofuran is also used as an initiator in polymerization reactions.
other names of THF are butylene oxide and diethylene oxide.
Tetrahydrofuran in the presence of strong acids can be converted to a linear polymer called polyether methylene ether glycol.
Tetrahydrofuran is used to make elastic polyurethane fibers and high-consumption solvents in the PVC industry.
Tetrahydrofuran is also used in resin manufacturing industries.
A similar solvent to this substance is benzene.
Name: Tetrahydrofuran (THF)
Molecular weight (g/mol): 72.11
Density (g/cm³ at 20 °C): 0.89
Viscosity (cp): 0.48
Boiling point (°C): 65-67
Melting point (°C): -108
Flash point (°C): -17.2
Dielectric Constant: 7.52
Vapor Pressure (mmhg): 143
Vapor density (vs air): 2.5
Synthesis and production of butylene oxide by 1،4 butane diols in the presence of acid catalysts and dehydration can be done.
In this method of producing tetrahydrofuran is the conversion of n-butane to maleic anhydride during the oxidation process and then by catalytic dehydrogenation can produce tetrahydrofuran.
another method of production of diethylene oxide is catalytic dehydration of furan as an available compound.
Tetrahydrofuran is a widely used solvent in the industry of PVC, natural and synthetic resins, vinyl films and cellophane, polymer coatings, protective coatings, and magnetic tapes.
Tetrahydrofuran is used in the pharmaceutical industry in the synthesis of drugs and vitamins and also in perfumery.
This material is also used in the production of synthetic leather coatings.
A special application of diethylene oxide is Tetrahydrofurans role in the formulation of PVC cement.
Cement solvents and additional solvents and mineral fillers can be used to adjust the performance time of cement.
Tetrahydrofuran can also act as a suitable cleaner for all types of PVC before forming the connection This solvent is also used in the production of nylon.
In many cases, the use of THF in the reaction allows higher efficiencies and faster reaction rates.
Also, the volatility and high purity of this solvent make Tetrahydrofuran easy to remove Tetrahydrofuran from the final product.
Tetrahydrofuran can also act as a corrosion inhibitor.
Tetrahydrofuran Storage and Handling
THF is classified under the Japanese Fire Services Act as a hazardous material, Class 4, Petroleums No.1, water soluble, Hazardous Rank II.
Since Tetrahydrofuran is highly volatile and flammable, the storage container should be tightly sealed and stored in a well-ventilated place.
When handling take precautions against fire.
Like other ethers, explosive peroxides will be generated if THF is exposed to oxygen or air.
For this reason the container should be sealed with dry nitrogen.
THF is irritating to the membranes and skin of the eyes, nose, and throat.
Exposure to the vapor for long time periods may cause organic solvent poisoning symptoms such as nausea and dizziness.
Use adequate ventilation to avoid high concentrations of vapor.
When using or handling, always use proper safety equipment such as protective gloves and goggles.
Tetrahydrofuran (THF) is an extremely valuable solvent that can also be polymerized into polytetramethylene ether glycol (PTMEG), which is the precursor for spandex fibers.
Thus, the INVISTA Company has increased the production capabilities of their Gulf Coast Lycra® plant and has commissioned another THF production plant to be built on the same premises.
The proposed plant will utilize a maleic acid byproduct from an internal upstream plant and will produce 100 million tons of THF per year.
The THF must be at least 99.95% by mass THF, since lower purity THF contains more –OH groups that would terminate the polymerization reaction required to synthesize spandex fibers.
Trade name of the product: tetrahydrofuran (THF)
Chemical name of the compound: oxolan, tetrahydrofuran
Synonyms: diethylene oxide; butylenoxide; 1,4-epoxybutane; cyclotetramethylene oxide; furanidine; oxacyclopentane; oxolane; tetramethylene oxide; butane, alpha, delta-oxide; alpha-hydro-omega-hydroxypoly(oxy-1,4-butanediyl)
Tetrahydrofuran Chemical and physical properties: a colorless liquid with a low viscosity and strong acetate- or ether-like odor; mixes well with water
Application of the substance: Depending on Tetrahydrofurans concentration, tetrahydrofuran can be used among others as the industrial solvent of natural and synthetic resins and polymers (first of all polyvinyl chloride – PVC).
Tetrahydrofuran is also widely used in the production varnishes, adhesives, inks and paints, and also in the synthesis of fuels, vitamins, hormones and pharmaceuticals, synthetic perfume and insecticides.
Tetrahydrofuran can also be used as a solvent of oils, fats and uncured rubber.
In Tetrahydrofurans polymerized form as poly(tetrahydromethylethyl) glycol (PTMEG), Tetrahydrofuran is used as the main component to produce Spandex-type elastomer polyurethane fibers.
Tetrahydrofuran, 99.8%, for biochemistry, unstabilized, AcroSeal(R)
Tetrahydrofuran, contains 250 ppm BHT as inhibitor, ACS reagent, >=99.0%
Tetrahydrofuran, 99.5%, Extra Dry over Molecular Sieve, Stabilized, AcroSeal(R)
Tetrahydrofuran, for luminescence, >=99.5% (GC)
Tetrahydrofuran, inhibitor-free, for HPLC, =99.9%
TETRAHYDROFURAN-2,2,5,5-D4,98 ATOM % D
Tetrahydrofuran, anhydrous, >=99.9%, inhibitor-free
Tetrahydrofuran, for HPLC, >=99.9%, inhibitor-free
Tetrahydrofuran, inhibitor-free, for HPLC, >=99.9%
Tetrahydrofuran, HPLC grade, >=99.9%, inhibitor-free
Tetrahydrofuran, non-UV, HPLC grade stabilized with BHT
Tetrahydrofuran, biotech. grade, >=99.9%, Inhibitor-free
Tetrahydrofuran, for amino acid analysis, without stabilizer
Tetrahydrofuran, p.a., 99%, contains 200-300 ppm BHT
Tetrahydrofuran solution, contains 20 % (v/v) 1,2-Propanediol
Tetrahydrofuran, HPLC, UV-IR, isocratic grade, unstabilized
Tetrahydrofuran, 99.9%, extra pure, anhydrous, stabilized with BHT
Tetrahydrofuran, anhydrous, inhibitor-free, ZerO2(TM), >=99.9%
Tetrahydrofuran, AR, contains 250 ppm BHT as stabilizer, 99.5%
Tetrahydrofuran, LR, contains 250 ppm BHT as stabilizer, >=99%
Tetrahydrofuran, spectrophotometric grade, >=99.5%, inhibitor-free
Tetrahydrofuran, ACS reagent, >=99.0%, contains 250 ppm BHT as inhibitor
Tetrahydrofuran, anhydrous, >=99.9%, contains 250 ppm BHT as inhibitor
Tetrahydrofuran, anhydrous, contains 250 ppm BHT as inhibitor, >=99.9%
Tetrahydrofuran, anhydrous, contains 250 ppm BHT as stabilizer, >=99.5%
Tetrahydrofuran, UV HPLC spectroscopic, 99.8%, contains 200-300 ppm BHT
Tetrahydrofuran, 99.85%, Extra Dry, stabilized, AcroSeal(R), package of 4x25ML bottles
Tetrahydrofuran, Pharmaceutical Secondary Standard; Certified Reference Material
Tetrahydrofuran, ReagentPlus(R), >=99.0%, contains 250 ppm BHT as inhibitor
Tetrahydrofuran, absolute, over molecular sieve (H2O <=0.005%), contains ~0.025% 2,6-di-tert-butyl-4-methylphenol as stabilizer, >=99.5% (GC)
Tetrahydrofuran, contains 250 ppm BHT as inhibitor, puriss. p.a., ACS reagent, Reag. Ph. Eur., >=99.9%
Tetrahydrofuran, Vetec(TM) reagent grade, anhydrous, contains 100 ppm BHT as inhibitor, >=99.8%
Tetrahydrofuran Air & Water Reactions
Oxidizes readily in air to form unstable peroxides that may explode spontaneously.
Tetrahydrofuran Solubles in water.
Tetrahydrofuran 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.
Tetrahydrofuran, SAJ first grade, >=99.0%
Tetrahydrofuran, Selectophore(TM), >=99.5%
Tetrahydrofuran [UN2056] [Flammable liquid]
Tetrahydrofuran HPLC grade stabilized with BHT
Tetrahydrofuran, JIS special grade, >=99.5%
Tetrahydrofuran, for HPLC, contains No stabilizer
Tetrahydrofuran, inhibitor-free, purification grade
Tetrahydrofuran, puriss. p.a., >=99.9% (GC)