Tetrahydrofuran

Base Information

• Chemical Name: Tetrahydrofuran
• CAS No.: 109-99-9
• Deprecated CAS: 77392-70-2
• Molecular Formula: C4H8O
• Molecular Weight: 72.1069
• Hs Code.: 2932.11
• European Community (EC) Number: 203-726-8,607-472-2
• ICSC Number: 0578
• NSC Number: 57858
• UN Number: 2056
• UNII: 3N8FZZ6PY4
• DSSTox Substance ID: DTXSID1021328
• Nikkaji Number: J2.878I
• Wikipedia: Tetrahydrofuran
• Wikidata: Q278332
• Metabolomics Workbench ID: 37158
• ChEMBL ID: CHEMBL276521
• Mol file: 109-99-9.mol

Synonyms:tetrahydrofuran

Chemical Property of Tetrahydrofuran

Chemical Property:

• Appearance/Colour: Colorless liquid
• Vapor Pressure: <0.01 mm Hg ( 25 °C)
• Melting Point: 33-36 ºC
• Refractive Index: n20/D 1.465
• Boiling Point: 68.3 ºC at 760 mmHg
• Flash Point: -21 ºC
• PSA: 9.23000
• Density: 0.904 g/cm₃
• LogP: 0.79680
• Storage Temp.: 2-8°C
• Sensitive.: Air Sensitive & Hygroscopic
• Solubility.: water: soluble
• Water Solubility.: miscible
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 72.057514874
• Heavy Atom Count: 5
• Complexity: 22.8
• Transport DOT Label: Flammable Liquid

Purity/Quality:

99.9%, ^*data from raw suppliers

Tetrahydrofuran ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,F
• Hazard Codes: Xi,F,Xn
• Statements: 36/37/38-36/37-19-11-40
• Safety Statements: 26-36-33-29-16-46-37-13

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Solvents -> Ethers (
• Canonical SMILES: C1CCOC1
• Inhalation Risk: A harmful contamination of the air can be reached rather quickly on evaporation of this substance at 20 °C.
• Effects of Short Term Exposure: The substance and the vapour are irritating to the eyes, skin and respiratory tract. The substance may cause effects on the central nervous system at high levels. This may result in narcosis.
• Effects of Long Term Exposure: Repeated or prolonged contact with skin may cause dermatitis. The substance may have effects on the liver and kidneys. This may result in impaired functions. This substance is possibly carcinogenic to humans.
• Description: Tetrahydrofuran (THF) is a colorless, volatile liquid with an ethereal or acetonelike smell and is miscible in water and most organic solvents.It 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.
• 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.
• Uses: Butylene oxide is used as a fumigant and inadmixture with other compounds. It 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 (Apr. 25, 1962). 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.

Technology Process of Tetrahydrofuran

There total 395 articles about Tetrahydrofuran which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

dimethyl cis-but-2-ene-1,4-dioate (624-48-6) → tetrahydrofuran (109-99-9,24979-97-3,77392-70-2) + 2-methoxytetrahydrofuran (13436-45-8) + 4-butanolide (96-48-0) + propan-1-ol (71-23-8) + 2-(4'-hydroxybutoxy)-tetrahydrofuran (64001-06-5) + Butane-1,4-diol (110-63-4) + butan-1-ol (71-36-3)

Guidance literature:

With hydrogen; copper catalyst, T 4489, Sud-Chemie AG, Munich; at 150 - 280 ℃; under 187519 Torr; Neat liquid(s) and gas(es)/vapour(s);

Reference yield: 79.1%

dimethyl cis-but-2-ene-1,4-dioate (624-48-6) → tetrahydrofuran (109-99-9,24979-97-3,77392-70-2) + 2-methoxytetrahydrofuran (13436-45-8) + 4-butanolide (96-48-0) + propan-1-ol (71-23-8) + 1-methoxy-1,4-butanediol + 2-(4'-hydroxybutoxy)-tetrahydrofuran (64001-06-5) + 4-hydroxy-butanoic acid 4-hydroxybutyl ester + Butane-1,4-diol (110-63-4) + 4-hydroxybutyraldehyde (25714-71-0) + methyl 4-hydroxybutanoate (925-57-5) + butan-1-ol (71-36-3)

Guidance literature:

With hydrogen; at 190 ℃; under 46504.7 Torr; Gas phase;

Reference yield: 77.2%

furan (110-00-9) + methanol (67-56-1) → tetrahydrofuran (109-99-9,24979-97-3,77392-70-2) + 1,4-dimethoxybutane (13179-96-9) + Methyl formate (107-31-3) + Methyl 4-methoxybutyrate (29006-01-7) + butan-1-ol (71-36-3)

Guidance literature:

With palladium on activated charcoal; hydrogen; at 170 ℃; for 2h; under 52505.3 Torr; Autoclave;

DOI:10.1039/c4gc01826e

upstream raw materials:

Tetrahydrofurfuryl alcohol

2,3-dihydro-2H-furan

furan

furfural

Downstream raw materials:

homoalylic alcohol

1,1,1-triphenyl-1-silapropan-3-ol

allyltriphenylsilane

2,5-bis-(triphenylsilanyl-methyl)-[1,4]dioxane

Refernces

• 1、 Cao, Ji,Hasegawa, Jun-Ya,Hosaka, Ryu,Nakagawa, Yoshinao,Nakayama, Akira,Tamura, Masazumi,Tomishige, Keiichi. "Mechanistic Study on Deoxydehydration and Hydrogenation of Methyl Glycosides to Dideoxy Sugars over a ReO x-Pd/CeO2Catalyst". . p. 12040 - 12051. Retrieved 2020.
• 2、 Pino, Natalia,Sitthisa, Surapas,Tan, Qiaohua,Souza, Talita,López, Diana,Resasco, Daniel E.. "Structure, activity, and selectivity of bimetallic Pd-Fe/SiO2 and Pd-Fe/Γ-Al2O3 catalysts for the conversion of furfural". . p. 30 - 40. Retrieved 2017.
• 3、 Ota, Nobuhiko,Tamura, Masazumi,Nakagawa, Yoshinao,Okumura, Kazu,Tomishige, Keiichi. "Hydrodeoxygenation of vicinal OH groups over heterogeneous rhenium catalyst promoted by palladium and ceria support". . p. 1897 - 1900. Retrieved 2015.
• 4、 Nakanishi, Kousuke,Tanaka, Atsuhiro,Hashimoto, Keiji,Kominami, Hiroshi. "Photocatalytic hydrogenation of furan to tetrahydrofuran in alcoholic suspensions of metal-loaded titanium(IV) oxide without addition of hydrogen gas". . p. 20206 - 20212. Retrieved 2017.
• 5、 Bhanushali, Jayesh T.,Prasad, Divya,Patil, Komal N.,Babu, Gurram Venkata Ramesh,Kainthla, Itika,Rao, Kamaraju Seetha Rama,Jadhav, Arvind H.,Nagaraja, Bhari Mallanna. "The selectively regulated vapour phase dehydrogenation of 1,4-butanediol to γ-butyrolactone employing a copper-based ceria catalyst". . p. 11968 - 11983. Retrieved 2019.
• 6、 Hu, Zhun,Mi, Rongli,Yang, Bolun,Yi, Chunhai. "Catalytic Dehydration of 1,4-Butanediol over Mg?Yb Binary Oxides and the Mechanism Study". . . Retrieved 2020.
• 7、 Goodings,Wilson. "-". . p. 4798. Retrieved 1951.
• 8、 Mironenko,Belskaya,Lavrenov,Likholobov. "Palladium–Ruthenium Catalyst for Selective Hydrogenation of Furfural to Cyclopentanol". . p. 339 - 346. Retrieved 2018.
• 9、 Bargon J.,Kandels, J.,Kating, P.,Thomas, A.,Woelk, K.. "NMR-DETECTION OF INTERMEDIATES DURING HOMOGENEOUS HYDROGENATION OF DIENES USING PARAHYDROGEN". . p. 5721 - 5724. Retrieved 1990.
• 10、 Garcia-Suarez, Eduardo J.,Balu, Alina Mariana,Tristany, Mar,Garcia, Ana Beatriz,Philippot, Karine,Luque, Rafael. "Versatile dual hydrogenation-oxidation nanocatalysts for the aqueous transformation of biomass-derived platform molecules". . p. 1434 - 1439. Retrieved 2012.