Perfluoro(methyl vinyl ether) is a

perfluorinated compound A perfluorinated compound (PFC) or perfluoro compound is an Organofluorine chemistry, organofluorine compound that lacks C-H bonds. Many perfluorinated compounds have properties that are quite different from their C-H containing analogues. Common ...

used as a precursor to

fluoropolymer A fluoropolymer is a fluorocarbon-based polymer with multiple carbon–fluorine bonds. It is characterized by a high resistance to solvents, acids, and bases. The best known fluoropolymer is polytetrafluoroethylene under the brand name "Teflon, ...

s. It is the simplest unsaturated

perfluoroether Perfluoroethers are a class of organofluorine compound containing one or more ether functional group. In general these compounds are structurally analogous to the related hydrocarbon ethers, except for the distinctive properties of fluorocarbons. ...

Preparation

Preparation begins with hexafluoropropylene oxide (HFPO) and carbonyl fluoride over a metal

fluoride Fluoride (). According to this source, is a possible pronunciation in British English. is an Inorganic chemistry, inorganic, Monatomic ion, monatomic Ion#Anions and cations, anion of fluorine, with the chemical formula (also written ), whose ...

catalyst. The fluoride reacts with the carbonyl, forming a perfluoro

alkoxide In chemistry, an alkoxide is the conjugate base of an alcohol and therefore consists of an organic group bonded to a negatively charged oxygen atom. They are written as , where R is the organyl substituent. Alkoxides are strong bases and, whe ...

anion. The anion attacks the

electrophilic In chemistry, an electrophile is a chemical species that forms bonds with nucleophiles by accepting an electron pair. Because electrophiles accept electrons, they are Lewis acids. Most electrophiles are positively charged, have an atom that carr ...

central carbon atom of HFPO in a nucleophilic ring-opening reaction similar to anionic polymerization. Elimination of

regenerates the catalyst and yields perfluoro(2-methoxy propionyl fluoride). The acyl fluoride is then treated with

potassium hydroxide Potassium hydroxide is an inorganic compound with the formula K OH, and is commonly called caustic potash. Along with sodium hydroxide (NaOH), KOH is a prototypical strong base. It has many industrial and niche applications, most of which utili ...

to produce the perfluorocarboxylate. The carboxylate is then heated, causing

decarboxylation Decarboxylation is a chemical reaction that removes a carboxyl group and releases carbon dioxide (CO2). Usually, decarboxylation refers to a reaction of carboxylic acids, removing a carbon atom from a carbon chain. The reverse process, which is ...

followed by elimination of

to form the vinyl ether.

References

{{reflist Trifluoromethyl ethers Vinyl ethers Perfluorinated compounds