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109-99-9

109-99-9 Structure

109-99-9 Structure
IdentificationMore
[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 PropertiesBack Directory
[Appearance]

Colorless liquid
[Appearance]

Tetrahydrofuran is a colorless liquid. Ethereal odor. The Odor Threshold is listed @ 3.8 (3M), 20-50 ppm, and 31 ppm.
[mp ]

33-36 °C
[bp ]

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
[color ]

<10(APHA)
[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
[Water Solubility ]

miscible
[FreezingPoint ]

-108℃
[Sensitive ]

Air Sensitive & Hygroscopic
[Detection Methods]

GC
[Merck ]

14,9211
[BRN ]

102391
[CAS DataBase Reference]

109-99-9(CAS DataBase Reference)
[NIST Chemistry Reference]

Furan, tetrahydro-(109-99-9)
[Storage Precautions]

Moisture sensitive;Light sensitive
[EPA Substance Registry System]

109-99-9(EPA Substance)
Safety DataBack 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
[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)
Raw materials And Preparation ProductsBack 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-->alpha,alpha-Diphenyl-L-prolinol-->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 InformationBack 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.
[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.
Material Safety Data Sheet(MSDS)Back Directory
[msds information]

1,4-Epoxybutane(109-99-9).msds
Questions And AnswerBack Directory
[Description]

Tetrahydrofuran, the abbreviation of THF, is a heterocyclic organic compound. It belongs to ethers and is the fully hydrogenated product of the aromatic compound furan.
It can be used as an aprotic solvent with moderate polarity in chemical reaction and solvent extraction. Tetrahydrofuran is a colorless, low viscosity liquid with a similar smell as ether. At room temperature, tetrahydrofuran is partially miscible with water. This is exploited by some of the illegal businessmen for mixing water with tetrahydrofuran reagent to earn huge profits. Upon storage, tetrahydrofuran can easily become peroxide, and therefore, the commercialized tetrahydrofuran often used BHT, i.e., 2,6-tert butyl p-cresol for preventing oxidation. Tetrahydrofuran can be placed into sealed bottle through sodium hydroxide for being stored in a dark place.
[Chemical Properties]

It is colorless, transparent liquid with ether odor. It is miscible with water, alcohols, ketones, benzene, esters, ethers, and hydrocarbons.
[Uses]

1. It can be used as the solvent and the raw material of organic synthesis.
2. It can also be used as the chromatography analysis reagents, organic solvents and the intermediate of nylon 66.
3. Tetrahydrofuran is the intermediate for synthetic pesticides fenbutatin. In addition, it can be directly used for synthetic fibers, synthetic resins, synthetic rubber as well as the solvent of many polymeric materials, precision tape and electroplating industry. Moreover, it is also used for preparation of adiponitrile, adipic acid, hexamethylene diamine, succinic acid, butanediol, and γ-butyrolactone. In the pharmaceutical industry, it can be used for the production of carbetapentane, progesterone, rifamycin and pharmaceutical solvents.
4. THF is an important raw material for organic synthesis as well as a solvent with excellent performance, which is especially suitable for dissolution of PVC, polyvinylidene chloride and butyl aniline. It is widely used as surface coating, anti-corrosion coatings, printing inks, the solvent of tapes and films paint, and also being used as the reaction solvent. When being used as the electroplate aluminum solution, it can randomly control the thickness as well as brightness of aluminum layer. THF itself can be subject to condensation (caused by the ring-open reaction induced by cation and further polymerization) to generate poly-tetramethylene ether glycol (PTMEG). PTMEG, together with toluene diisocyanate (TDI) can generate special rubber of wear-resistant, oil resistance, excellent performance at low temperature as well as high strength; it can also generate block polyether/polyester elastic material with dimethyl terephthalate and 1, 4-butanediol. PTMGE of Molecular weight being 2000, together with methylene bis (4-phenyl) diisocyanate (MDI) can generate polyurethane elastic fiber (SPANDEX fiber), special rubber and the raw material of some kinds of coatings of special purpose. In the field of organic synthesis, it can be used for producing tetrahydrothiophene, 1, 4-dichloroethane, 2, 3-dichloro-tetrahydrofuran, valerolactone, butyrolactone and pyrrolidone. In the pharmaceutical industry, THF can be used for the synthesis of carbetapentane, rifamycin, progesterone, and some kinds of hormone drugs. THF, after being subject to hydrogen sulfide treatment, can generate tetrahydrothiophene. It can be used as the odor agent (identification additive) in fuel gas. THF can also be used as the surface treatment agent for synthetic leather.
5. It can also be applied to the paper chromatography of amino acids and peptides. It can be used as solvent; for organic synthesis as well as being applied to HPLC and UV spectrophotometry assay.
[resin solvent]

flexographic inks for plastics
coating deposition for audio and video tapes
PVC and CPVC pipe cements
polyurethane coatings
PVC film casting (food packaging)
[reaction solvent]

Grignard Reagent formation processes
pharmaceutical steroids
preparation of organometallic reagents
[Toxicology]

Oral-rat; LD50: 1650 mg/kg; inhalation LC50: 21000 ppm/3H. Inhalation-mice LCLo: 24000 mg/m3/2H.
It has low toxicity. This product has irritation effect on the skin and mucous membranes. At high concentrations it has an anesthetic effect with the anesthetic concentration being similar as lethal concentrations. High dose also has certain liver toxicity.
Rats, when being inhaled of 590mg/m^ 3, after 3 hours, has their eyelids and nasal become redness; inhalation> 147750mg/m^ 3, corneal edema and opacity, salivation, runny nose and nasal bleeding can occur.
Rats, guinea pigs, rabbits and cats, when being placed in a concentration of 50mg/L concentration for 3 hours, some animals can get side down; deepened anesthesia can appear under a dose of 100mg/L; some animals can directly die after exposure of 1 to 4.5 hours; a dose of 200 mg/ L can cause anesthesia within 1 hour with long term action being able to cause death. Rats, when get the inhaled concentrations> 14000mg/m ^ 3, can sleep, get stiffness, enter into deep coma, get convulsions, and also have epileptic brain waves. For the anesthesia effect, the animals can development certain resistance after repeated inhalation. Animals, when exposed to high doses once or repeated exposure, can get liver fatty infiltration and cell lysis. The oral administration can cause stomach bleeding and ulcers.
Applying 20% aqueous solution directly to the skin of rabbits can cause moderate skin irritation while 50% aqueous solution can cause severe corrosive damage.
Applying 20% aqueous solution to the rabbit eyes can cause severe keratitis.
THF, when touched with air, can form explosive peroxides which can increase the stimulating effect of THF.
According the foreign report, the concentration for causing anesthesia of human is 73800mg/m ^ 3. The threshold of human olfactory is 88.5mg/m ^ 3.
The above information is edited by the Chemicalbook of Dai Xiongfeng.
[Purification of tetrahydrofuran]

Tetrahydrofuran is miscible with water and often contains a small amount of water and peroxide. For making dry tetrahydrofuran, you can make it through flux with lithium aluminium hydride insulting the moisture (typically 1000 mL takes about 2~4 lithium aluminum hydride for removing the water and peroxide inside it, then further go through distillation; when collect the distilling fraction at 66 ℃, don’t totally dry it without the remaining small amount of residue being poured). Add the sodium wire to the refined liquid and further store it in a nitrogen atmosphere. Upon processing of tetrahydrofuran, we should first apply a small amount of it for being subject to testing to make sure that it only contains a small amount of water and peroxide with a relative mild reaction before we can purify it. The peroxide contained in tetrahydrofuran can be determined by the acidified potassium iodide solution. If the peroxides are in relative large amount, it is recommended that it is processed separately.
[Production method]

The earliest industrial production use uronic as raw material and put the mixture of uronic and steam into the reactor containing zinc-chromium-manganese metal oxide (or palladium) catalyst for stripping the carbonyl group at 400-420 ℃ to obtain furan; then take the raney nickel as the catalyst, perform furan hydrogenation reaction at 80-120 ℃ to obtain tetrahydrofuran. Applying this method for the production of one ton of tetrahydrofuran will cost about three tons of polysaccharide aldehyde. There are many kinds of production process developed later. Industrial methods include 1, 4-butanediol catalytic dehydration method; because butanediol is produced from acetylene and formaldehyde, this method is called as Reppe method; another method taking the byproduct of neoprene monomer chloroprene, 1, 4-dichloro-butene for production of tetrahydrofuran. This method is called dichloro butene method. In recent years, it was developed of the catalytic hydrogenation using maleic anhydride as the raw material.
There are mainly five kinds of approaches for production of tetrahydrofuran, as below:
1. Furfural method
It can be made through the decarbonylation of furfural can generate furan, and then have hydrogenation to obtain it.
This is one of the earliest ways of production of tetrahydrofuran on industrial process. Furfural is mainly produced through the hydrolysis of corn cob and other agricultural products. The pollution is serious and is not suitable for large-scale production and has been gradually eliminated.
2. Catalytic hydrogenation of maleic anhydride
Maleic anhydride and hydrogen gas were put into the reactor containing nickel catalyst inside of it from the bottom; the ratio between tetrahydrofuran and γ-butyrolactone in the product can be controlled by adjusting the operating parameters. The reaction product and the raw material hydrogen gas were cooled to about 50 ℃ and enter into the bottom of the scrubber to separate the unreacted hydrogen and gaseous product from liquid product; The unreacted hydrogen and the gaseous products were recycled to the reactor after washing while the liquid product was subject to distillation to obtain tetrahydrofuran.
This technology can randomly adjust the ratio of γ-butyrolactone and tetrahydrofuran at the range of 0 to (5:1) with the conversion rate of maleic anhydride in single round being 100%. The selectivity of tetrahydrofuran ranges from 85% to 95% with the product content being 99.97%. The process has good catalyst performance, simple process, and less investment.
3. 1, 4-butanediol dehydration cyclization
This process is that: ad 1087 kg of 22% aqueous sulfuric acid to the reactor, add 1,4-butanediol at 100 ℃ at a rate of 110kg/h with the overhead temperature being maintained at 80 °C. By doing this, we can obtain the 80% tetrahydrofuran anhydrous solution from the top of the tower at a speed of 110 kg/h speed. After adding 50 t of 1, 4-butanediol, you should further exclude approximately 70kg coke from the reactor. The coke was further filtered with the resulting aqueous sulfuric acid solution being able to be recycled. The tetrahydrofuran yield of this process can reach 99%.
Sulfuric acid is the earliest catalyst applied in the industrial production of tetrahydrofuran, and it also has a lot of applications in current production. This technology is mature with simple process, lower reaction temperatures, and high yield of tetrahydrofuran. However, the sulfuric acid is corrosive to equipment and can cause environmental pollution.
4. dichloro-butene method
This method takes 1, 4-dichloro-butene as raw material to produce butylene glycol through hydrolysis and further go through catalytic hydrogenation to obtain it.
1, 4-dichloro-butene can be hydrolyzed in sodium hydroxide solution with generating butylene glycol at 110°C. Centrifuge to remove the sodium chloride; the filtrate was concentrated in an evaporator crystallizer and the alkali metal carboxylate slat can be separated out; then remove the high-boiling matter in distillation column. Put the refined butenediol into the reactor; tae nickel as catalyst and have butenediol undergone hydrogenation reaction to generate butanediol at 80~120 ℃ and certain pressure. After distillation, the resulting product further entered into cyclization reactor to generate crude tetrahydrofuran in acidic medium at atmospheric pressure and at 120~140 ℃; Further conduct distillation and dehydration and remove high-boiling substance; finally distill again to obtain highly pure tetrahydrofuran.
This method is simple with mild conditions, high yield and less catalyst which can be used continuously.
5. Oxidation of butadiene
Use butadiene as raw material; it generate furan after oxidation; furan further generate the tetrahydrofuran through hydrogenation. This method has been industrialized in foreign countries.
Spectrum DetailBack Directory
[Spectrum Detail]

Tetrahydrofuran(109-99-9)MS
Tetrahydrofuran(109-99-9)1HNMR
Tetrahydrofuran(109-99-9)13CNMR
Tetrahydrofuran(109-99-9)Raman
Tetrahydrofuran(109-99-9)IR1
Well-known Reagent Company Product InformationBack Directory
[Acros Organics]

Tetrahydrofuran, stabilized with BHT, for analysis ACS, 99.6%(109-99-9)
[Alfa Aesar]

Tetrahydrofuran, UV, HPLC Grade, 99.7+% min, unstab.(109-99-9)
[Sigma Aldrich]

109-99-9(sigmaaldrich)
[TCI AMERICA]

Tetrahydrofuran  Anhydrous (stabilized with BHT),>98.0%(GC)(109-99-9)
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