# Perfluoroether

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'''Perfluoroethers''' are a class of [organofluorine compound](/source/organofluorine_compound) containing one or more [ether](/source/ether) [functional group](/source/functional_group).  In general these compounds are structurally analogous to the related hydrocarbon ethers, except for the distinctive properties of [fluorocarbon](/source/fluorocarbon)s.

The introduction of an ether function to a perfluoro-polymer chain also provides thermoplastic properties to the polymer, making thermal forming possible. This is a great technological advantage for producing a large variety of shapes (e.g., beakers, funnels, flasks for laboratory uses, etc...) and allows [extrusion](/source/Plastics_extrusion) of highly chemically-resistant tubing. It also confers on the polymer a translucent appearance.<ref>{{cite encyclopedia |author=Günter Siegemund |author2=Werner Schwertfeger |author3=Andrew Feiring |author4=Bruce Smart |author5=Fred Behr |author6=Herward Vogel |author7=Blaine McKusick |title=Fluorine Compounds, Organic|encyclopedia=Ullmann's Encyclopedia of Industrial Chemistry|publisher=Wiley-VCH|place=Weinheim|year=2002|doi=10.1002/14356007.a11_349|isbn=3-527-30673-0}}</ref>

==Low molecular weight fluorinated ethers==
[[Image:pfa tubing.jpeg|thumb|right|[PFA](/source/Perfluoroalkoxy_alkane) tubing is commonly used to handle aggressive chemicals]]
[[Image:Nafion2.svg|thumb|right|[Nafion](/source/Nafion) is a fluoroether with strongly acidic sulfonic acid substituents]]
[Acyclic](/source/Open-chain_compound) perfluoroethers are analogues of [diethylether](/source/diethylether), e.g. O(C<sub>2</sub>F<sub>5</sub>)<sub>2</sub>, such perfluoro(2-ethoxyethane)sulfonic acid	(PFEESA). 

Of practical utility are the fluorinated [epoxide](/source/epoxide)s. [Tetrafluoroethylene oxide](/source/Tetrafluorooxirane) and [hexafluoropropylene oxide](/source/hexafluoropropylene_oxide). These are precursors of [perfluoro(methyl vinyl ether)](/source/perfluoro(methyl_vinyl_ether)) (CF<sub>2</sub>=CFOCF<sub>3</sub>) and perfluoro(propyl vinyl ether),<ref name="PerfluorinatedVinylEtherSynthesisPatent">{{cite patent |country = US |number = 3180895A |invent1 = John Ferguson Harris, Jr. |invent2 = Donald Irwin McCane |status = patent |title = Fluorocarbon Ethers |gdate = 1965-04-27 |fdate = 1960-11-25}}</ref> and are used as [comonomer](/source/monomer)s with [tetrafluoroethylene](/source/tetrafluoroethylene), where they improve the properties of the resulting [polytetrafluoroethylene](/source/polytetrafluoroethylene) (e.g., [Teflon](/source/Teflon)).

==Polymeric perfluoroethers==
[Perfluoroalkoxy alkane](/source/Perfluoroalkoxy_alkane)s (PFAs) are [fluoropolymer](/source/fluoropolymer)s with properties similar to [polytetrafluoroethylene](/source/polytetrafluoroethylene) (PTFE). Methylfluoroalkoxy (MFA) is a polytetrafluoroethylene perfluoro methylvinylether prepared with a different ratio of PTFE and MVE monomers to that used for PFA. In these materials, the ether groups are pendant from the polymer backbone.

[Krytox](/source/Krytox) is a grease generated by the polymerization of hexafluoropropylene oxide.  Its [chemical formula](/source/chemical_formula) is F−(CF(CF<sub>3</sub>)−CF<sub>2</sub>−O)<sub>''n''</sub>−CF<sub>2</sub>CF<sub>3</sub>.  The ether groups are integral to the polymer chain.<ref name=Ullmann>{{cite encyclopedia|title=Fluoroethers and Fluoroamines |author=Michael G. Costello |author2=Richard M. Flynn |author3=John G. Owens |year=2001|publisher=Wiley-VCH|place=Weinstein|encyclopedia=Kirk-Othmer Encyclopedia of Chemical Technology|doi=10.1002/0471238961.0612211506122514.a01.pub2|isbn=0-471-23896-1}}</ref> 

[Nafion](/source/Nafion) is a perfluorinated polyether with pendant [sulfonic acid](/source/sulfonic_acid) groups (RSO<sub>3</sub>H).

== Precautions ==
At high temperatures or in a fire, perfluoroethers decompose and may release [hydrogen fluoride](/source/hydrogen_fluoride). Any residue must be handled using protective equipment.

==References==
{{reflist}}

==External links==
* [https://www.fluorotherm.com/technical-information/materials-overview/pfa-properties/ MFA Properties]

Category:Fluoropolymers
Category:Thermoplastics
Category:Organofluorides
Category:Perfluorinated compounds

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Adapted from the Wikipedia article [Perfluoroether](https://en.wikipedia.org/wiki/Perfluoroether) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Perfluoroether?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.