Tetrahydrofuran (THF) is a colorless organic compound. It is commonly used as a solvent in various industries due to its ability to dissolve a wide range of substances.
| IUPAC Name | Oxolane |
| Molecular Formula | C4H8O |
| CAS Number | 109-99-9 |
| Synonyms | THF, Oxacyclopentane, Butylene oxide, Diethylene oxide, Cyclotetramethylene oxide |
| InChI | InChI=1S/C4H8O/c1-2-4-5-3-1/h1-4H2 |
Tetrahydrofuran Properties
Tetrahydrofuran Formula
Tetrahydrofuran (THF) has a chemical formula of C4H8O. It is a cyclic ether with a five-membered ring containing four carbon atoms and one oxygen atom. THF has a low boiling point and is commonly used as a solvent in various industries.
Tetrahydrofuran Molar Mass
The molar mass of THF is approximately 72.11 g/mol. This value is calculated by adding the atomic masses of the constituent atoms in the molecular formula. THF’s relatively low molar mass contributes to its low boiling point and volatility, making it an effective solvent for a wide range of organic compounds.
Tetrahydrofuran Boiling Point
The boiling point of THF is 66°C (151°F) at standard atmospheric pressure. The low boiling point of THF makes it useful as a solvent for chemical reactions that require high temperatures, such as Grignard reactions. However, the low boiling point also means that THF is highly volatile, so care must be taken when handling it.
Tetrahydrofuran Melting Point
The melting point of THF is approximately −108.5°C (−163.3°F). THF is a liquid at room temperature, but it can solidify at low temperatures. The low melting point of THF makes it useful as a cryogenic solvent for low-temperature applications.
Tetrahydrofuran Density g/mL
The density of THF is approximately 0.889 g/mL at 20°C (68°F). This value is relatively low compared to other common solvents. The low density of THF makes it useful as a solvent for density-sensitive reactions, as it can decrease the overall density of the reaction mixture.
Tetrahydrofuran Molecular Weight
The molecular weight of THF is approximately 72.11 g/mol. This value is calculated by adding the atomic masses of the constituent atoms in the molecular formula. The relatively low molecular weight of THF contributes to its low boiling point and volatility.
Tetrahydrofuran Structure
THF has a five-membered ring structure with four carbon atoms and one oxygen atom. The carbon atoms are arranged in a tetrahedral geometry, with each carbon atom bonded to two other carbon atoms and one hydrogen atom. The oxygen atom is bonded to one carbon atom and one hydrogen atom.
Tetrahydrofuran Solubility
THF is a polar aprotic solvent that can dissolve a wide range of organic compounds. THF is miscible with water and is commonly used as a co-solvent in various chemical reactions. However, THF may not be compatible with certain materials, so it is important to check its compatibility before using it.
| Appearance | Colorless liquid |
| Specific gravity | 0.889 |
| Color | Colorless |
| Odor | Ether-like odor |
| Molar mass | 72.11 g/mol |
| Density | 0.889 g/mL |
| Melting point | −108.5°C (−163.3°F) |
| Boiling point | 66°C (151°F) |
| Flash point | −14°C (7°F) |
| Water solubility | Miscible |
| Solubility | Soluble in ethanol, ether, acetone, benzene |
| Vapour pressure | 200 mmHg at 20°C |
| Vapour density | 2.5 (air = 1) |
| pKa | 25.3 |
| pH | Neutral (7) |
Tetrahydrofuran Safety and Hazards
Tetrahydrofuran (THF) poses several safety and health hazards. THF is highly flammable and can ignite at room temperature. It can also release toxic fumes when heated or burned. Exposure to THF can cause skin and eye irritation, and prolonged exposure can lead to liver and kidney damage. THF is also known to cause dizziness and headaches, and repeated inhalation can lead to respiratory problems. Care must be taken when handling THF, and protective equipment such as gloves and safety glasses should be worn. THF should be stored in a cool, well-ventilated area away from heat sources and incompatible materials.
| Hazard symbols | Flammable, Toxic |
| Safety description | Highly flammable liquid and vapor. Causes serious eye irritation. May cause drowsiness or dizziness. May be harmful if swallowed or inhaled. |
| UN IDs | UN2056 |
| HS Code | 29321100 |
| Hazard class | 3 (Flammable Liquids) |
| Packing group | II |
| Toxicity | LD50 (oral, rat) – 5,410 mg/kg |
Tetrahydrofuran Synthesis Methods
Several methods can synthesize Tetrahydrofuran (THF).
One common method involves the catalytic hydrogenation of furan. This involves passing furan vapor over a nickel or palladium catalyst in the presence of hydrogen gas. The resulting reaction produces THF and water as byproducts.
Another method involves the reaction of 1,4-butanediol with sulfuric acid, followed by distillation to produce THF. Concentrated sulfuric acid’s hazards make this method less common for use.
The acid-catalyzed dehydration of 1,4-butanediol is another way to synthesize THF. This method involves heating the 1,4-butanediol with a strong acid, such as sulfuric acid, to remove water and produce THF.
Furthermore, one can obtain THF through catalytic hydrogenolysis of cellulose or other biomass-derived sugars. This method is of increasing interest due to the potential for renewable sources of THF production.
Each method has its advantages and disadvantages, and the specific method chosen will depend on factors such as cost, availability of starting materials, and desired purity of the final product.
Tetrahydrofuran Uses
Tetrahydrofuran (THF) has a variety of industrial and laboratory applications, including:
- Solvent: Commonly used as a solvent for various organic compounds due to its high solvency power and low boiling point.
- Polymerization: Used as a co-solvent in the polymerization of polystyrene and polyvinyl chloride, as well as in the production of polyurethane foams.
- Chemical synthesis: Used as a reaction solvent in organic chemical synthesis, such as in the preparation of Grignard reagents.
- Extraction: Used as an extraction solvent for various natural products, such as alkaloids and steroids.
- Adhesives: Used as a component in adhesive formulations, such as those used in shoe and leather manufacturing.
- Coatings: Used in the production of coatings and varnishes, as well as in the formulation of paints and lacquers.
- Analytical chemistry: Used as a mobile phase solvent in high-performance liquid chromatography (HPLC) and gas chromatography (GC) analyses.
Questions:
Q: What is the major organic product formed when tetrahydrofuran is treated with excess HBr?
A: When THF is treated with excess HBr, the major organic product formed is 3-bromo-1,4-dioxane.
Q: Is tetrahydrofuran miscible in water?
A: Yes, THF is miscible in water. It has a high solubility in polar solvents, including water.
Q: Will tetrahydrofuran damage rubber?
A: Yes, THF can damage the rubber. It can cause swelling, softening, and cracking of rubber materials.
Q: Is tetrahydrofuran polar or nonpolar?
A: THF is a polar solvent. It has a dipole moment due to the oxygen atom in its ring structure, which makes it a good solvent for polar compounds.
Q: Will tetrahydrofuran explode in water?
A: No, THF will not explode in water. However, it can form an explosive peroxide if it is exposed to air for extended periods of time. Proper storage and handling are necessary to prevent the formation of peroxides.
Q: What is the SDS for tetrahydrofuran?
A: The SDS (Safety Data Sheet) for THF provides information on its physical and chemical properties, handling and storage instructions, health and safety precautions, and emergency response procedures. It is important to review and follow the information provided in the SDS when working with THF.