Perfluoroisobutene

Last updated
Perfluoroisobutene
Perfluoroisobutene.svg
Perfluoroisobutene-3D-balls.png
Names
Preferred IUPAC name
1,1,3,3,3-Pentafluoro-2-(trifluoromethyl)prop-1-ene
Other names
Perfluoroisobutene, Perfluoroisobutylene, Octafluoroisobutylene, Octafluoro-sec-butene, PFIB
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.108.743 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 609-533-9
PubChem CID
RTECS number
  • UD1800000
UNII
  • InChI=1S/C4F8/c5-2(6)1(3(7,8)9)4(10,11)12 X mark.svgN
    Key: DAFIBNSJXIGBQB-UHFFFAOYSA-N X mark.svgN
  • InChI=1/C4F8/c5-2(6)1(3(7,8)9)4(10,11)12
    Key: DAFIBNSJXIGBQB-UHFFFAOYAF
  • FC(F)=C(C(F)(F)F)C(F)(F)F
Properties
C4F8
Molar mass 200.030 g/mol
Appearancecolorless gas
Density 8.2 g/l
Melting point −130 °C (−202 °F; 143 K)
Boiling point 7.0 °C (44.6 °F; 280.1 K)
Hazards
GHS labelling:
GHS-pictogram-skull.svg GHS-pictogram-silhouette.svg
Danger
H330, H370
P260, P264, P270, P271, P284, P304+P340, P307+P311, P310, P320, P321, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Perfluoroisobutene (PFIB) is the perfluorocarbon with the formula (CF3)2C=CF2. Classified as a perfluoroalkene, it is the fluorinated counterpart of the hydrocarbon isobutene. This colorless gas is notable for its high toxicity. [1]

Contents

Production and reactions

PFIB is one product of pyrolysis of polytetrafluoroethylene (PTFE). [2] Tetrafluoroethylene thermally dimerizes to octafluorocyclobutane, which above 600 °C degrades to hexafluoropropylene and PFIB. [1]

Perfluoroisobutene is highly reactive toward nucleophiles, e.g. methanol. [1] It also forms addition compounds with thiols, and it is this reactivity that may be related to its toxicity. [3] It hydrolyzes readily to give the relatively innocuous (CF3)2CHCO2H, which readily decarboxylates to give hexafluoropropane.[ citation needed ]

Oxidation of HFIB with potassium permanganate gives hexafluoroacetone. [4]

Safety

Perfluoroisobutene is highly toxic with an LCt = 880 mg⋅min⋅m−3 (mice). [3] It is a Schedule 2 substance of the Chemical Weapons Convention. Its toxicity is comparable to that of phosgene. [1]

References

  1. 1 2 3 4 Siegemund, Günter; Schwertfeger, Werner; Feiring, Andrew; Smart, Bruce; Behr, Fred; Vogel, Herward; McKusick, Blaine (2000). "Fluorine Compounds, Organic". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a11_349. ISBN   978-3-527-30385-4.
  2. ↑ Stewart, Charles E. (2006). Weapons of mass casualties and terrorism response handbook. American Academy of Orthopaedic Surgeons. Sudbury, Mass: Jones and Bartlett. ISBN   978-0-7637-2425-2.
  3. 1 2 Timperley, Christopher M. (2000). "Highly-toxic fluorine compounds". Fluorine Chemistry at the Millennium. pp. 499–538. doi:10.1016/B978-008043405-6/50040-2. ISBN   9780080434056.
  4. ↑ Michael Van Der Puy, Louis G. Anello (1985). "Hexafluoroacetone". Organic Syntheses. 63: 154. doi:10.15227/orgsyn.063.0154.
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