Tetrahydrofuran CAS 109-99-9

Tetrahydrofuran CAS 109-99-9

Tetrahydrofuran (THF), or oxolane, is an organic compound with the formula (CH2)4O. The compound is classified as heterocyclic compound, specifically a cyclic ether. It is a colorless, water-miscible organic liquid with low viscosity. It is mainly used as a precursor to polymers.

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What is Tetrahydrofuran CAS 109-99-9

 

 

Tetrahydrofuran (THF), or oxolane, is an organic compound with the formula (CH2)4O. The compound is classified as heterocyclic compound, specifically a cyclic ether. It is a colorless, water-miscible organic liquid with low viscosity. It is mainly used as a precursor to polymers.

 

Benefits of Tetrahydrofuran CAS 109-99-9

Low Viscosity
Tetrahydrofuran has a low viscosity and is a very fluid liquid. Compared with other solvents, it diffuses faster in the reaction mixture, speeding up the reaction rate and increasing the reaction yield. Therefore, tetrahydrofuran is often used as a solvent and plays an important role in organic reactions with high activity.

 

Low Volatility
Tetrahydrofuran is a less volatile solvent. Its volatility is much lower than that of ordinary organic hydrogen compounds, and it is difficult to volatilize even at high temperatures. This low volatility allows THF to be used under general laboratory conditions, while also reducing the risk of solvent residue and ensuring the reliability and accuracy of experiments.

 

High Dielectric Constant
Tetrahydrofuran has a relatively high dielectric constant and is a polar solvent. Its molecules are highly polar and have strong polar bonds and hydrogen bonds, and can effectively dissolve polar molecules and compounds involved in hydrogen bond formation. Tetrahydrofuran has a wide range of applications in the fields of biochemistry, electrochemistry and materials science.

 

Wide Application
Because tetrahydrofuran has the characteristics of low viscosity, low volatility and high dielectric constant, it is possible to use it as a selective solvent in active organic reactions. At the same time, tetrahydrofuran is also widely used in the fields of chemistry, medicine, biology and materials. It can be used as a solvent for synthetic drugs and natural products, for the synthesis of anti-cancer, anti-viral and antibacterial drugs; it can also be used for the synthesis of conductive polymers, battery materials, photonic crystals and other high-tech materials.

 

 

 
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Tetrahydrofuran Chemical Formula Structure

The chemical formula structure of tetrahydrofuran is an oxygen atom connected to a ring composed of four carbon atoms. Each carbon atom is connected to a hydrogen atom. Its molecular formula is C4H8O, which can also be written as (CH2)4O. Tetrahydrofuran is a heterocyclic organic compound, which belongs to the ethers and is the complete hydrogenation product of furan. This compound is a colorless and transparent liquid with an ether-like smell. It is soluble in water, ethanol, ether, acetone, benzene, etc. It is mainly used as a solvent, chemical synthesis intermediate, and analytical reagent. It should be noted that on October 27, 2017, in the list of carcinogens published by the World Health Organization' s International Agency for Research on Cancer, tetrahydrofuran was listed as a Category 2B carcinogen.

 

What Are the Important Applications of Tetrahydrofuran in Medicine

 

Tetrahydrofuran plays an important role in the pharmaceutical field, and its wide range of applications makes it a solvent of great interest. This article will introduce the specific applications of tetrahydrofuran in drugs, including its solubility characteristics, reaction media, and impact on drug synthesis and formulation processes.

 

Tetrahydrofuran is a polar solvent with good solubility properties and can dissolve a variety of compounds, including hydrophobic and polar compounds. This makes it a commonly used reaction medium and solvent of choice in drug synthesis.

 

Tetrahydrofuran is of great significance in drug synthesis. It can be used as a reaction medium to promote chemical reactions and improve product purity and yield. At the same time, tetrahydrofuran can also be used as a solvent to dissolve and transfer reactants during drug synthesis. Its polar characteristics enable it to effectively promote the dissolution and diffusion of reactants, thereby improving reaction efficiency.

 

Tetrahydrofuran also has an important impact on the preparation process. In the development and production of pharmaceutical preparations, tetrahydrofuran is often used to dissolve pharmaceutical raw materials and excipients for subsequent mixing, granulation, and packaging. Its solubility and polarity properties make it an ideal solvent choice for pharmaceutical manufacturing processes.

 

As an important solvent, tetrahydrofuran plays an invisible heroic role in the field of medicine. It plays an important role in drug synthesis and formulation through its solubility properties and reaction medium properties. In the future, with the continuous development of pharmaceutical technology, the application prospects of tetrahydrofuran will be broader, providing more possibilities for drug development and production.

What Is Tetrahydrofuran Used For
 

Organic Synthesis
THF is a commonly used organic synthesis solvent and is widely used in many organic synthesis reactions, such as Grignard reaction, metal catalyzed reaction, esterification reaction, etc. It is able to dissolve many organic compounds, making them easier to react with.

 

Polymerization Reaction
THF can be used as a reaction solvent for some polymerization reactions, especially in the process of synthesizing polymer materials such as polyurethane and polyacrylate.

 

Dissolution Of Metal Ion Complexes
Because THF has good solubility for many metal ion complexes, it is widely used to synthesize metal organic compounds or perform organometallic chemical reactions.

 

Solvent Extraction
THF can be used in chemical separation and extraction processes, such as for extracting natural products, separating compounds in mixtures, etc.

 

Polymer Dissolution
THF is a solvent with strong solubility and can be used to dissolve and process some high molecular polymers, such as polyacrylate and polycaprolactone.

 

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What Are the Physical and Chemical Properties of Tetrahydrofuran CAS 109-99-9

Tetrahydrofuran is one of the most polar ethers. It is used as a medium polar solvent in chemical reactions and extractions. It is a colorless and volatile liquid at room temperature, with an ether-like smell. Soluble in most organic solvents such as water, ethanol, ether, acetone, and benzene, it is called a "universal solvent". It is partially miscible with water at room temperature. Some unscrupulous reagent dealers take advantage of this fact to make huge profits by mixing tetrahydrofuran reagent with water.

 

Oxidation Method of Tetrahydrofuran
 

Oxidation reaction with hydrogen peroxide

The oxidation reaction of tetrahydrofuran using hydrogen peroxide is a common method, and the reaction conditions are usually carried out at room temperature. In this reaction, hydrogen peroxide can be promoted by a catalyst, making the oxidation reaction more likely to occur. Different catalysts affect reaction rate and selectivity. Common catalysts include transition metal ions and alkali metal ions.


Using hydrogen peroxide and copper acetate as catalysts, tetrahydrofuran can be oxidized to tetrahydrofuran-1,4-dione. The reaction mechanism is mainly through the decomposition of hydrogen peroxide by a catalyst to generate hydroxyl radicals, which then attack the double bonds of tetrahydrofuran and finally form tetrahydrofuran-1,4-dione.

Use phosphorus trichloride peroxide for oxidation reaction

In addition to hydrogen peroxide, phosphorus trichloride peroxide can also be used in the oxidation reaction of tetrahydrofuran. This method has advantages in both reaction rate and selectivity, and is also widely used in organic synthesis.


Phosphorus peroxide trichloride is commonly used as hydrogen peroxide with various properties. It can initiate free radical reactions and oxidize tetrahydrofuran. During the reaction, phosphorus trichloride peroxide decomposes into phosphorus trichloride and oxygen. Oxygen and tetrahydrofuran react to form the target product.

 

How Is Tetrahydrofuran Produced Industrially

Tetrahydrofuran (THF), referred to as THF, has a molecular formula of C4H8O, a boiling point of 66°C, a specific gravity of D20 40.886~0.888, and a refractive index n20 of D1.4060~1.4080. Due to its fast dissolution speed, good diffusion performance, good fluidity, low toxicity, and low boiling point, it has good dissolving properties for both organic and inorganic substances. Known as the "universal solvent", it can be used for resins, polyethers, etc. Used as solvent in rubber and polyurethane synthesis. In pharmaceutical engineering, it is the basic raw material for the synthesis of Kebiqing, rifamycin, progesterone, prednisone, Naofukang, etc. Tetrahydrofuran can also be used to produce tetramethylene glycol ether (PTMEG), adipic acid, butylene glycol, dichlorobutane, tetrahydrothiophene, butyrolactone, pyrrolidone, 2.3-dichlorotetrahydrofuran and other chemical products. THF can also be used as acetylene extraction solvent, tape cleaning agent, synthetic leather surface coating agent, polymer material light stabilizer, etc. At present, the world's THF production capacity is about 500,000 tons, which is mainly used to synthesize polytetramethylene alcohol ether (PTMEG) and used as a solvent. Due to different national conditions in various countries, the consumption distribution of THF is also different.

 

Tetrahydrofuran Storage Conditions
Storage Temperature

Tetrahydrofuran is a flammable liquid, and its storage temperature should be controlled at or below room temperature, preferably not higher than 30 degrees Celsius. Excessively high temperatures can easily decompose tetrahydrofuran, producing harmful gases and precipitates, which can lead to explosions in severe cases.

Light

Tetrahydrofuran should be stored in a dark, dry place away from direct sunlight. Ultraviolet rays in sunlight will destroy the molecular structure of THF, causing it to produce harmful oxidation products, affecting its chemical properties and solubility.

Ventilation

Tetrahydrofuran has strong volatility and peculiar smell. It should be stored in a well-ventilated place to avoid mixing with other items and polluting the environment. When using tetrahydrofuran, a chemical fume hood or supporting ventilation equipment should be used to prevent harmful gases from causing damage to the human body.

Container Selection

Tetrahydrofuran should be stored in glass bottles or plastic bottles with good airtight performance. Avoid using metal or plastic transparent containers. Metal containers are easily corroded by the oxidation of tetrahydrofuran to produce harmful gases, and plastic transparent containers are easily affected by ultraviolet rays and produce harmful oxidation products.

 

Effect of Tetrahydrofuran on Enzyme Activities in Activated Sludge

 

 

Tetrahydrofuran is an important solvent widely used in industrial and laboratory research work. However, little is known about the effects and fate of tetrahydrofuran (THF) in the environment. Some attempts to enrich microorganisms in activated sludge to degrade THF have failed. The effect of THF on the activities of dehydrogenase, protease, phosphatase, urease and catalase in activated sludge was studied. The activated sludge was taken from the secondary sedimentation tank of Sibao Wastewater Treatment Plant in Hangzhou, China, and the changes in enzyme activity in the presence of tetrahydrofuran were observed. The results showed that within the selected concentration range, tetrahydrofuran completely inhibited dehydrogenase activity during culture, on the contrary, did not inhibit protease activity, and strongly affected phosphatase, urease and catalase activities, and with increasing tetrahydrofuran concentration , phosphatase, urease and catalase activities decreased. . Calculate the EC10, EC50 and EC90 of tetrahydrofuran on the phosphatase, urease and catalase activities based on the equations obtained from the dose-response curve regression model. Understanding the impact of THF on enzyme diversity in activated sludge can help us understand the impact and fate of THF in the environment, and help us enrich THF degradation pure isolates or activated sludge. 

 

 

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FAQ
 

Q: What is tetrahydrofuran used for?

A: THF is widely used as a solvent for special resins such as photosensitive resins, because even at room temperature it can dissolve various resins, and it is miscible with water and most organic solvents. In, addition, it is used as a solvent for Grignard and Wittig

Q: What is the formula of tetrahydrofuran?

A: Tetrahydrofuran (THF) is a clear, colourless, organic compound with an ether-like odour and the formula (CH2)4O

Q: What kind of waste is tetrahydrofuran?

A: Tetrahydrofuran has to be disposed as hazardous waste in the appropriate organic waste container, which has to be kept closed at all times. THF is a peroxide generator and can form peroxide upon contact with air. Peroxides can be contact explosive.

Q: Where is tetrahydrofuran found?

A: THF is a solvent used in the preparation of resins, adhesives, paints, printing inks, and plastics composites and is also used as a wetting agent for textiles. It can be found in the indoor air, resulting from emissions of various consumer products containing composite plastics, polymers, and adhesives.

Q: What is the alternative to tetrahydrofuran?

A: When used as an organometallic solvent, 2-MeTHF offers both economical and environmentally friendly advantages over Tetrahydrofuran.

Q: What is the first aid of tetrahydrofuran?

A: In case of contact, immediately flush eyes or skin with plenty of water for at least 15 minutes. Remove contaminated clothing and shoes. Wash clothing before reuse. In all cases, get medical attention.

Q: What is the medicinal use of tetrahydrofuran?

A: In the pharmaceutical industry, THF is used for the synthesis of carbetapentane, rifamycin, progesterone, and some hormone drugs.

Q: How long does tetrahydrofuran last?

A: Containers of Tetrahydrofuran should be protected from physical damage, direct sunlight, and ignition sources. Test open containers every 3 months with peroxide test strips. Dispose one year after purchase. Be sure there are no white crystals forming on the outside of the bottle, around the cap.

Q: Does tetrahydrofuran melt plastic?

A: Another common cause of weakening of plastics is exposure to certain solvents and chemicals. Solvents and chemicals can be absorbed by the plastic causing the plastic to soften and lose rigidity and strength. Tetrahydrofuran (THF) is co the most universal and common solvent for many plastics.

Q: What does THF smell like?

A: Of the other common lab solvents, THF has a rather pungent ethereal smell - not something you'd line up for, by any means, and diethyl ether itself fills up your nose with great speed and thoroughness.

Q: What is the function of THF?

A: Tetrahydrofolic acid (THF) acts as the carrier for one-carbon groups, necessary for many biosynthetic pathways such as amino acid and nucleic acid metabolism. Notably, THF is an essential precursor in the thymidine synthesis pathway.

Q: Is THF flammable?

A: Extremely flammable liquid and vapor. Vapor may cause flash fire. Vapors are heavier than air and may travel to a source of ignition and flash back. Vapors can spread along the ground and collect in low or confined areas.

Q: Where is tetrahydrofuran used?

A: Tetrahydrofuran (THF) is a chemical intermediate used in the manufacture of polymers as well as agricultural, pharmaceutical, and commodity chemicals. Manufacturing activities commonly occur in closed systems or under engineering controls that limit worker exposure and release to the environment.

Q: How is THF made?

A: Tetrahydrofuran (THF) is made by hydrogenation of furan. With furan being made from furfural, THF is a "second generation descendant" of furfural. The process is commonly carried out at 100 °C and 20 bar, using a catalyst consisting of 5 % palladium on microporous carbon.

Q: What are the benefits of tetrahydrofuran?

A: Tetrahydrofuran is a commonly used solvent, having the advantage that it is a relatively inert water-miscible ether. It is often used as a solvent in organometallic chemistry and it is particularly useful in the preparation of Grignard reagents from chlorobenzenes and vinyl chlorides.

Q: How is Tetrahydrofuran CAS 109-99-9 produced?

A: 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.

Q: What are the safety precautions when handling Tetrahydrofuran CAS 109-99-9?

A: The following recommendations are only guidelines and may not apply to every situation. * Avoid skin contact with Tetrahydrofuran. Wear solvent- resistant gloves and clothing. Safety equipment suppliers/ manufacturers can provide recommendations on the most protective glove/clothing material for your operation.

Q: How does Tetrahydrofuran CAS 109-99-9 interact with other chemicals?

A: It 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.

Q: What are the storage requirements for Tetrahydrofuran CAS 109-99-9?

A: P403 + P233: Store in a well-ventilated place. Keep container tightly closed. Strongly contaminated halogen-free organic solvents: container A. Store at +2°C to +30°C.

Q: How is Tetrahydrofuran CAS 109-99-9 disposed of after use?

A: Tetrahydrofuran has to be disposed as hazardous waste in the appropriate organic waste container, which has to be kept closed at all times. THF is a peroxide generator and can form peroxide upon contact with air. Peroxides can be contact explosive.

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