| Tetrahydrofuran | |
|---|---|
 |
 |
| IUPAC name | Oxacyclopentane |
| Other names | THF, tetrahydrofuran, 1,4-epoxybutane, butylene oxide, cyclotetramethylene oxide, oxacyclopentane, diethylene oxide, oxolane, furanidine, hydrofuran, tetra-methylene oxide |
| Identifiers | |
| CAS number | [109-99-9] |
| RTECS number | LU5950000 |
| SMILES | C1CCCO1 |
| Properties | |
| Molecular formula | C4H8O |
| Molar mass | 72. IUPAC Nomenclature is a system of naming Chemical compounds and of describing the science of Chemistry in general CAS registry numbers are unique numerical identifiers for Chemical compounds Polymers biological sequences mixtures and Alloys They are also referred to Registry of Toxic Effects of Chemical Substances ( RTECS) is a Database of Toxicity information compiled from the open scientific literature without reference A chemical formula is a way of expressing information about the Atoms that constitute a particular Chemical compound, and how the relationship between those atoms changes Molar mass, symbol M, is the Mass of one mole of a substance ( Chemical element or Chemical compound) 11 g/mol |
| Appearance | colorless liquid |
| Density | 0. The density of a material is defined as its Mass per unit Volume: \rho = \frac{m}{V} Different materials usually have different 8892 g/cm3 @ 20 °C, liquid |
| Melting point |
-108. The melting point of a solid is the temperature range at which it changes state from solid to Liquid. 4 °C (164. 75 K) |
| Boiling point |
66 °C (339. The boiling point of a liquid is the temperature at which the Vapor pressure of the liquid equals the environmental pressure surrounding the liquid 15 K) |
| Solubility in water | Miscible |
| Viscosity | 0. Solubility is the characteristic Physical property referring to the ability of a given substance the Solute, to dissolve in a Solvent. Water is a common Chemical substance that is essential for the survival of all known forms of Life. Viscosity is a measure of the resistance of a Fluid which is being deformed by either Shear stress or Extensional stress. 48 cP at 25 °C |
| Structure | |
| Molecular shape | envelope |
| Dipole moment | 1. Molecular geometry or molecular structure is the three- Dimensional arrangement of the Atoms that constitute a Molecule. In physics there are two kinds of dipoles ( Hellènic: di(s- = two- and pòla = pivot hinge An electric dipole is a 63 D (gas) |
| Hazards | |
| MSDS | External MSDS |
| EU classification | Flammable (F) Irritant (Xi) |
| NFPA 704 |
 3
2
0
|
| R-phrases | R11, R19, R36/37 |
| S-phrases | S16, S29, S33 |
| Flash point | -14 °C |
| Related compounds | |
| Related heterocycles | Furan Pyrrolidine Dioxane |
| Related compounds | Diethyl ether |
| Supplementary data page | |
| Structure and properties |
n, εr, etc. The debye (symbol D) is a non- SI, CGS unit of electrical dipole moment. A material safety data sheet ( MSDS) is a form containing data regarding the properties of a particular substance This page provides supplementary chemical data on Tetrahydrofuran Council Directive 67/548/EEC of 27 June 1967 on the approximation of laws regulations and administrative provisions relating to the classification packaging and labelling Symbolism The four divisions are typically color-coded with blue indicating level of Health Hazard, red indicating R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. The flash point of a flammable liquid is the lowest Temperature at which it can form an ignitable mixture in air Furan, also known as furane and furfuran, is a heterocyclic Organic compound. Pyrrolidine, also known as tetrahydropyrrole, is an Organic compound with the molecular formula C4H9N Diethyl ether, also known as ether and ethoxyethane, is a clear colorless and highly Flammable liquid with a low Boiling point and a This page provides supplementary chemical data on Tetrahydrofuran This page provides supplementary chemical data on Tetrahydrofuran The refractive index (or index of Refraction) of a medium is a measure for how much the speed of light (or other waves such as sound waves is reduced inside the medium Measurement The relative static permittivity εr can be measured for static Electric fields as follows first the Capacitance of a test |
| Thermodynamic data |
Phase behaviour Solid, liquid, gas |
| Spectral data | UV, IR, NMR, MS |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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- "THF" redirects here. This page provides supplementary chemical data on Tetrahydrofuran This page provides supplementary chemical data on Tetrahydrofuran Ultraviolet-visible spectroscopy or ultraviolet-visible spectrophotometry ( UV/ VIS) involves the Spectroscopy of Photons in the UV-visible Infrared spectroscopy (IR spectroscopy is the subset of Spectroscopy that deals with the Infrared region of the Electromagnetic spectrum. Nuclear magnetic resonance spectroscopy, most commonly known as NMR spectroscopy, is the name given to a technique which exploits the magnetic properties of certain nuclei Mass spectrometry is an analytical technique that identifies the chemical composition of a compound or sample based on the Mass-to-charge ratio of charged particles In Chemistry, the standard state of a material is its state at 1 bar (100 Kilopascals exactly For other uses, see THF (disambiguation).
Tetrahydrofuran, also known as THF, is a heterocyclic organic compound with the formula (CH2)4O). An organic compound is any member of a large class of Chemical compounds whose Molecules contain Carbon. It is a colourless low-viscosity liquid with a smell similar to diethyl ether. Viscosity is a measure of the resistance of a Fluid which is being deformed by either Shear stress or Extensional stress. Diethyl ether, also known as ether and ethoxyethane, is a clear colorless and highly Flammable liquid with a low Boiling point and a It is one of the most polar ethers. "Polar molecule" and "Non-polar" redirect here Ether is a class of Organic compounds which contain an ether group — an Oxygen Atom connected to two (substituted Alkyl THF is the fully hydrogenated analog of the aromatic compound furan. Hydrogenation is the Chemical reaction that results in addition of Hydrogen (H2 Furan, also known as furane and furfuran, is a heterocyclic Organic compound.
Contents |
Solvent properties
THF is an aprotic solvent with a dielectric constant of 7. In Chemistry a protic solvent is a Solvent that has a Hydrogen atom bound to an Oxygen as in a Hydroxyl group or a Nitrogen A solvent is a liquid or gas that dissolves a solid liquid or gaseous Solute, resulting in a Solution. Measurement The relative static permittivity εr can be measured for static Electric fields as follows first the Capacitance of a test 6. It is a moderately polar, aprotic solvent that dissolves a wide range of nonpolar and polar compounds.
Diethyl ether can often be substituted by THF when a higher-boiling solvent is required. Diethyl ether, also known as ether and ethoxyethane, is a clear colorless and highly Flammable liquid with a low Boiling point and a Thus THF, like diethyl ether, is often used for hydroborations used to synthesize primary alcohols. In Organic chemistry, the hydroboration-oxidation reaction is a two-step organic chemical reaction that converts an Alkene into a neutral Alcohol Both ethers have an oxygen atom which can coordinate to the electron-deficient boron atom, forming an adduct. See also Adduction, one of the Anatomical terms of motion. An adduct (from the Latin adductus, "drawn toward" is Similarly, THF or diethyl ether are often used as solvents for Grignard reagents because of the oxygen atom's ability to coordinate to the magnesium ion component of the Grignard reagent. The Grignard reaction, named for the French chemist François Auguste Victor Grignard, is an organometallic Chemical reaction in which Alkyl - In addition, the oxygen atom has no acid hydrogen that can undergo acid-base reaction with the Grignard reagent. 2-methyltetrahydrofuran has become a popular THF alternative, based on its similar properties to THF, but having a lower melting point (useful for lower temperature reactions), as well as having a higher boiling point (useful for solvent retention under reflux).
THF is often used in polymer science. For example, it can be used to dissolve rubber prior to determining its molecular mass using gel permeation chromatography. Size exclusion chromatography (SEC is a chromatographic method in which particles are separated based on their size or in more technical terms their Hydrodynamic volume THF dissolves PVC as well, and is the main ingredient in PVC adhesives. It can be used to liquefy old PVC cement.
THF can be polymerized by strong acids to give a linear polymer called poly(tetramethylene ether) glycol (PTMEG), CAS Registry Number [25190-06-1], also known as PTMO, polytetramethylene oxide. A polymer is a large Molecule ( Macromolecule) composed of repeating Structural units typically connected by Covalent Chemical bonds Poly(tetramethylene ether glycol is a Polyether polyol. It is also known as PTMEG or polytetrahydrofuran and various tradenames such as "Terathane" CAS registry numbers are unique numerical identifiers for Chemical compounds Polymers biological sequences mixtures and Alloys They are also referred to The primary use of this polymer is to make elastomeric polyurethane fibers like Spandex. An elastomer is a Polymer with the property of Elasticity. The term which is derived from elastic polymer, is often used interchangeably with the term A polyurethane, commonly abbreviated PU, is any Polymer consisting of a chain of organic units joined by urethane links Spandex or elastane is a Synthetic fiber known for its exceptional elasticity. [1].
It is often used industrially to degrease metal parts. Although the word grease originally described the rendered fat of animals the term is now applied more broadly to mean a Lubricant of higher initial Viscosity
Preparation
THF can be synthesized by catalytic hydrogenation of furan[2]. Hydrogenation is the Chemical reaction that results in addition of Hydrogen (H2 Furan, also known as furane and furfuran, is a heterocyclic Organic compound.
The major industrial process for making THF is the acid-catalyzed dehydration of 1,4-butanediol. [3] Du Pont developed a process for producing THF by oxidizing n-butane to crude maleic anhydride, followed by catalytic hydrogenation of maleic anhydride to THF. E I du Pont de Nemours and Company (,) is an American chemical company that was founded in July 1802 as a Gunpowder mill by Eleuthère Irénée Redox (shorthand for reduction-oxidation reaction describes all Chemical reactions in which atoms have their Oxidation number ( Oxidation state Butane, also called n -butane, is the unbranched Alkane with four Carbon Atoms CH3CH2CH2CH3 Maleic anhydride ( cis -butenedioic anhydride toxilic anhydride dihydro-25-dioxofuran is an Organic compound with the formula C4H2O3 Hydrogenation is the Chemical reaction that results in addition of Hydrogen (H2 Maleic anhydride ( cis -butenedioic anhydride toxilic anhydride dihydro-25-dioxofuran is an Organic compound with the formula C4H2O3 [3][4]
Precautions
THF tends to form peroxides on storage in air. Organic peroxides are Organic compounds containing the Peroxide Functional group (ROOR' As a result, THF should not be distilled to dryness, which can leave a residue of highly-explosive peroxides. Commercial THF is therefore often inhibited with BHT. Butylated hydroxytoluene (BHT also known as Butylhydroxytoluene, is a Lipophilic (fat-soluble Organic compound that is primarily used as an
See also
- The Trapp mixture extends the temperature range applicability of THF as a solvent. The Trapp mixture is a specific Mixture of organic Solvents for Chemical reactions taking place at very low Temperatures The mixture THF
References
- ^ "Polyethers, Tetrahydrofuran and Oxetane Polymers by Gerfried Pruckmayr, P. Dreyfuss, M. P. Dreyfuss". Kirk‑Othmer Encyclopedia of Chemical Technology. (1996). John Wiley & Sons, Inc.
- ^ Morrison, Robert Thornton; Boyd, Robert Neilson: Organic Chemistry, 2nd ed. , Allyn and Bacon 1972, p 569
- ^ a b "Ethers, by Lawrence Karas and W. J. Piel". Kirk‑Othmer Encyclopedia of Chemical Technology. (2004). John Wiley & Sons, Inc. Retrieved on 2007-09-05. Year 2007 ( MMVII) was a Common year starting on Monday of the Gregorian calendar in the 21st century. Events 1590 - Alexander Farnese 's army forces Henry IV of France to raise the siege of Paris.
- ^ Merck Index of Chemicals and Drugs, 9th ed. monograph 8929
- Loudon, G. Mark. Organic Chemistry 4th ed. New York: Oxford University Press. 2002. pg 318.
External links
- THF usage on Organic Syntheses
- THF info
- U.S. OSHA info on THF
- 2-Methyltetrahydrofuran, An alternative to Tetrahydrofuran and Dichloromethane. Sigma-Aldrich. Retrieved on 2007-05-23. Year 2007 ( MMVII) was a Common year starting on Monday of the Gregorian calendar in the 21st century. Events 1430 - Siege of Compiègne: Joan of Arc is captured by the Burgundians while leading an army to relieve Compiègne
- Tetrahydrafuran (THF) Storage and Handling. BASF. Retrieved on 2007-05-24. Year 2007 ( MMVII) was a Common year starting on Monday of the Gregorian calendar in the 21st century. Events 1218 - The Fifth Crusade leaves Acre for Egypt. 1276 - Magnus Ladulås is crowned
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