Perfluoro(methyl vinyl ether)
.png) | |
| Names | |
|---|---|
| IUPAC name 1,1,2-trifluoro-2-(trifluoromethoxy)ethene | |
Other names
| |
| Identifiers | |
3D model (JSmol) | |
| Abbreviations | PMVE, PFMVE |
| ChemSpider | |
| ECHA InfoCard | 100.013.367 |
PubChem CID | |
CompTox Dashboard (EPA) | |
| |
| |
| Properties | |
| C3F6O | |
| Molar mass | 166.022 g·mol−1 |
| Appearance | colourless gas |
| Hazards[1] | |
| GHS labelling: | |
   | |
| Danger | |
| H220, H221, H280, H315, H319, H332, H335 | |
| P203, P210, P222, P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P332+P317, P337+P317, P362+P364, P377, P381, P403, P403+P233, P405, P410+P403, P501 | |
| Related compounds | |
Related compounds | Methyl vinyl ether |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
Perfluoro(methyl vinyl ether) is a perfluorinated compound used as a precursor to fluoropolymers. It is the simplest unsaturated perfluoroether.
Preparation
[edit]Preparation begins with hexafluoropropylene oxide (HFPO) and carbonyl fluoride over a metal fluoride catalyst. The fluoride reacts with the carbonyl, forming a perfluoroalkoxide anion. The anion attacks the electrophilic central carbon atom of HFPO in a nucleophilic ring-opening reaction similar to anionic polymerization. Elimination of fluoride regenerates the catalyst and yields perfluoro(2-methoxy propionyl fluoride). The acyl fluoride is then treated with potassium hydroxide to produce the perfluorocarboxylate.[2]
The carboxylate is then heated, causing decarboxylation followed by elimination of fluoride to form the vinyl ether.[3]
References
[edit]- ^ "Perfluoro(methyl vinyl ether)". PubChem. National Center for Biotechnology Information. Retrieved 2025-04-25.
- ^ Sullivan, Raymond (1969). "Synthesis of perfluoroalkyl vinyl ether acids and derivatives". The Journal of Organic Chemistry. 34 (6): 1841–1844. doi:10.1021/jo01258a067.
- ^ Trang, Brittany; Li, Yuli; Xue, Xiao-Song; Ateia, Mohamed; Houk, K. N.; Dichtel, William R. (2022). "Low-temperature mineralization of perfluorocarboxylic acids". Science. 377 (6608): 839–845. Bibcode:2022Sci...377..839T. doi:10.1126/science.abm8868. PMID 35981038.