|Preferred IUPAC name
3D model (JSmol)
CompTox Dashboard (EPA)
|Molar mass||100.02 g/mol|
|Density||1.519 g/cm3 at -76 °C|
|Melting point||−142.5 °C (−224.5 °F; 130.7 K)|
|Boiling point||−76.3 °C (−105.3 °F; 196.8 K)|
|NFPA 704 (fire diamond)|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
Tetrafluoroethylene (TFE) is a fluorocarbon with the chemical formula C2F4. It is the simplest perfluorinated alkene. This gaseous species is used primarily in the industrial preparation of fluoropolymers.
Tetrafluoroethylene is a colorless, odorless gas. Like all unsaturated fluorocarbons, it is susceptible to nucleophilic attack. It is unstable towards decomposition to carbon and carbon tetrafluoride (CF
4) and prone to form explosive peroxides in contact with air.
Polymerization of tetrafluoroethylene produces polytetrafluoroethylene (PTFE) polymers such as Teflon and Fluon. PTFE is one of the two fluorocarbon resins composed wholly of fluorine and carbon. The other resin composed purely of carbon and fluorine is the copolymer of TFE with typically 6–9% hexafluoropropene (HFP), which is known as FEP (fluorinated ethylene propylene copolymer). TFE is also used in the preparation of numerous copolymers that also include hydrogen and/or oxygen, including both fluoroplastics and fluoroelastomers. Typical TFE-based fluoroplastics include ETFE, the alternating 1:1 copolymer with ethylene, and PFA, which is a random copolymer similar to FEP but with a minor amount of a perfluoroalkyl vinyl ether (PAVE) rather than HFP. DuPont uses primarily perfluoro(methylvinylether), whereas Daikin uses primarily perfluoro(propylvinylether) in manufacturing PFA. There are numerous other fluoropolymers that contain tetrafluoroethylene, but usually not at greater than 50% by weight.
TFE is manufactured from chloroform. Chloroform is fluorinated by reaction with hydrogen fluoride to produce chlorodifluoromethane (R-22). Pyrolysis of chlorodifluoromethane (at 550-750 °C) yields TFE, with difluorocarbene as an intermediate.
- CHCl3 + 2 HF → CHClF2 + 2 HCl
- 2 CHClF2 → C2F4 + 2 HCl
Alternatively, it can be prepared by pyrolysis of fluoroform:
- 2 CHF3 → C2F4 + 2 HF
The reverse polymerization reaction – vacuum pyrolysis of PTFE at 650–700 °C (1,200–1,290 °F) in a quartz vessel – is a convenient laboratory synthesis of TFE. The PTFE polymer cracks, and at a pressure below 5 Torr (670 Pa) exclusively C2F4 is obtained. At higher pressures the product mixture contains hexafluoropropylene and octafluorocyclobutane.
The main hazard associated with TFE is that of explosion, especially if oxygen is present. TFE reacts with oxygen at low temperatures to form an explosive oxide, the detonation of which is usually sufficient to trigger explosive decomposition of TFE to C and CF4. Explosions can also be caused by adiabatic compression if the TFE is being handled under high pressure. If pressurised TFE is allowed into a vessel/pipework at a lower pressure then the atmosphere in the vessel will be compressed by the TFE, causing it to heat up, potentially to the point where it might detonate the TFE. This has been known to cause explosions. In industry, pipework is flushed with pressurized nitrogen, before the introduction of TFE, both to exclude oxygen and prevent adiabatic compression.
- Gozzo, F.; Camaggi, G. (January 1966). "Oxidation reactions of tetrafluoroethylene and their products—I". Tetrahedron. 22 (6): 1765–1770. doi:10.1016/S0040-4020(01)82248-1.
- Siegemund, Günter; Schwertfeger, Werner; Feiring, Andrew; Smart, Bruce; Behr, Fred; Vogel, Herward; McKusick, Blaine (2002). "Fluorine Compounds, Organic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a11_349.
- R. J. Hunadi & K. Baum (1982). "Tetrafluoroethylene: A Convenient Laboratory Preparation". Synthesis. 39: 454. doi:10.1055/s-1982-29830.
- "The Explosive Decomposition of Tetrafluoroethylene: Large Scale Tests and Simulations | Request PDF". ResearchGate. Retrieved 2018-11-01.
- Reza, Ali; Christiansen, Erik (March 2007). "A case study of a TFE explosion in a PTFE manufacturing facility". Process Safety Progress. 26 (1): 77–82. doi:10.1002/prs.10174.
- NIH Substance Profile for TFE
- "TETRAFLUOROETHYLENE" (PDF). International Agency for Research on Cancer. Retrieved 20 May 2020.
- National Toxicology Program Chemical Repository
- Tetrafluoroethylene, hexafluoropropylene and vinylidene fluoride terpolymer -- aka THV, melt-processable members of the fluorocarbon family
- Sleeuwenhoek, Anne; Cherrie, John (2012). "Exposure assessment of tetrafluoroethylene and ammonium perfluorooctanoate 1951-2002". Journal of Environmental Monitoring.