Perfluoro(methyl vinyl ether)
Chemical compound
From Wikipedia, the free encyclopedia
Perfluoro(methyl vinyl ether) is a perfluorinated compound with the formula CF3OCF=CF2. It is the simplest unsaturated perfluoroether. It is a precursor to fluoropolymers.
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| Names | |
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| IUPAC name
1,1,2-trifluoro-2-(trifluoromethoxy)ethene | |
Other names
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| Identifiers | |
3D model (JSmol) |
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| Abbreviations | PMVE, PFMVE |
| ChemSpider | |
| ECHA InfoCard | 100.013.367 |
| EC Number |
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PubChem CID |
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| UNII | |
| UN number | 3153 |
CompTox Dashboard (EPA) |
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| Properties | |
| C3F6O | |
| Molar mass | 166.022 g·mol−1 |
| Appearance | colourless gas |
| Boiling point | −29 °C (−20 °F; 244 K) |
| Hazards[1] | |
| GHS labelling: | |
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| 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).
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Preparation
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. Decarboxylation via pyrolysis then yields the ether.[2]
Sulfuryl fluoride adds across the double bond to give CF3OCF(CF3)SO2F. [3]