Perfluoro(methyl vinyl ether)

Perfluoro(methyl vinyl ether)

Names
IUPAC name 1,1,2-trifluoro-2-(trifluoromethoxy)ethene
Other names Trifluoromethyl trifluorovinyl ether Trifluoromethoxy trifluoroethylene
Identifiers
CAS Number	1187-93-5
3D model (JSmol)	Interactive image
Abbreviations	PMVE, PFMVE
ChemSpider	13820
ECHA InfoCard	100.013.367
EC Number	214-703-7
PubChem CID	14474
UNII	6II375V3XG
UN number	3153
CompTox Dashboard (EPA)	DTXSID3051599
InChI InChI=1S/C3F6O/c4-1(5)2(6)10-3(7,8)9 Key: BLTXWCKMNMYXEA-UHFFFAOYSA-N
SMILES C(=C(F)F)(OC(F)(F)F)F
Properties
Chemical formula	C3F6O
Molar mass	166.022 g·mol−1
Appearance	colourless gas
Boiling point	−29 °C (−20 °F; 244 K)
Hazards [1]
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H220, H221, H280, H315, H319, H332, H335
Precautionary statements	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). Infobox references

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.

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]

Safety and environmental

Its derivatives are included in the PFAS pollutants emitted by manufacturers of fluorocarbons. ^[4]

References

1. "Perfluoro(methyl vinyl ether)". PubChem . National Center for Biotechnology Information . Retrieved 2025-04-25.
2. Sullivan, Raymond (1969). "Synthesis of perfluoroalkyl vinyl ether acids and derivatives". The Journal of Organic Chemistry. 34 (6): 1841–1844. doi:10.1021/jo01258a067.
3. Böttcher, T.; Duda, B.; Kalinovich, N.; Kazakova, O.; Ponomarenko, M.; Vlasov, K.; Winter, M.; Röschenthaler, G.-V. (2014). "Syntheses of novel delocalized cations and fluorinated anions, new fluorinated solvents and additives for lithium ion batteries". Progress in Solid State Chemistry. 42 (4): 202–217. doi:10.1016/j.progsolidstchem.2014.04.013.
4. d'Ambro, Emma L.; Pye, Havala O. T.; Bash, Jesse O.; Bowyer, James; Allen, Chris; Efstathiou, Christos; Gilliam, Robert C.; Reynolds, Lara; Talgo, Kevin; Murphy, Benjamin N. (2021). "Characterizing the Air Emissions, Transport, and Deposition of Per- and Polyfluoroalkyl Substances from a Fluoropolymer Manufacturing Facility". Environmental Science & Technology. 55 (2): 862–870. Bibcode:2021EnST...55..862D. doi:10.1021/acs.est.0c06580. PMC   7887699 . PMID   33395278.