Perfluorovinyl methyl ether

Copolymers from tetrafluoroethylene and 40% perfluorovinyl methyl ether are also elastomers (glass-transition temperature — 12°C). The copolymerization is carried out in aqueous emulsion with ammonium perfluoro-octanoate as emulsifier. Vulcanization is possible with hexamethylene diamine via the small amount of perfluoro(4-carboxy methyl butyl vinyl ether) also polymerized into the copolymer. This ether is produced from perfluoroglutaryl fluoride and hexafluoropropylene oxide. 

Souzy et al. [106] studied the radical homo-, co-, and teipolymerization of 4-[(a,, -tiifluorovinyl)oxy]bromobenzene with commercially available fluoroalkenes such as vinyUdene fluoride (VDF), chlorotrifluoroethylene (CTFE), hexafluoropropylene (IffP), and/or perfluorovinyl methyl ether (PMVE) (Fig- 2.24). 

The preparation and use of these nucleophilic organometallic reagents in the presence of electrophilic fluorinated olefins was a surprising result and prompted us to explore theoretical support for their stability. Upon calculating (at the ab initio level) deprotonation energies of trifluorovinyloxy substituted benzene and pyridine model compounds vs. the corresponding methyl ether, we found that perfluorovinyl... 

The synthesis of carboxylated perfluorovinyl ether was very difficult and no preparative method had been known before. Recently, however, several synthetic methods have been proposed. An example of the synthetic route to methyl perfluoro-5-oxa-6-heptenoate (M ) and methyl perfluoro-5,8-dioxa-6-methyl-9-decenoate (M2) is shown in the following scheme. 

---