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Tetrafluoroethylene

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Tetrafluoroethylene

Tetrafluoroethylene (TFE) is a fluorocarbon with the chemical formula C2F4. It is a colorless gas. Its structure is F2C=CF2. It is used primarily in the industrial preparation of fluoropolymers. It is the simplest perfluorinated alkene.

Tetrafluoroethylene was first obtained by the French chemist fr:Camille Chabrié by heating tetrachloroethylene with silver(II) fluoride:

It was named "dicarbon tetrafluoride" based on its composition, analogous to "dicarbon tetrachloride" for tetrachloroethylene which it was first made from.

Tetrafluoroethylene is a synthetic colorless, odorless gas that is insoluble in water. Like all unsaturated fluorocarbons, it is susceptible to nucleophilic attack. It is unstable towards decomposition to carbon and carbon tetrafluoride (CF4) and prone to form explosive peroxides in contact with air.

Polymerization of tetrafluoroethylene produces fluoropolymers 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, the precursor of TFE (R-22). Pyrolysis of chlorodifluoromethane (at 550–750 °C) yields TFE, with difluorocarbene as an intermediate.

Alternatively, it can be prepared by pyrolysis of fluoroform, which is also produced from chloroform and HF:

A convenient, safe method for generating TFE is the pyrolysis of the sodium salt of pentafluoropropionic acid:

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