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Octafluorocyclobutane

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(Redirected from Perfluorocyclobutane)
Octafluorocyclobutane
Structural formula of octafluorocyclobutane
Ball-and-stick of the octafluorocyclobutane molecule
Names
Preferred IUPAC name Octafluorocyclobutane
Other names Freon-C-318, perfluorocyclobutane
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference 1909266
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.705 Edit this at Wikidata
EC Number
  • 204-075-2
E number E946 (glazing agents, ...)
Gmelin Reference 131113
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C4F8/c5-1(6)2(7,8)4(11,12)3(1,9)10Key: BCCOBQSFUDVTJQ-UHFFFAOYSA-N
  • InChI=1/C4F8/c5-1(6)2(7,8)4(11,12)3(1,9)10Key: BCCOBQSFUDVTJQ-UHFFFAOYAW
SMILES
  • C1(C(C(C1(F)F)(F)F)(F)F)(F)F
Properties
Chemical formula C4F8
Molar mass 200.03 g/mol
Appearance colourless gas
Density 1.637 g/cm at −5.8 °C (liquid)

9.97 kg/m at −6 °C and 1 atm (gas)
8.82 kg/m 15 °C and 1 atm (gas)

Melting point −40.1 °C (−40.2 °F; 233.1 K)
Boiling point −5.8 °C (21.6 °F; 267.3 K)
Solubility in water 0.016 vol/vol (1.013 bar and 20 °C)
Viscosity 109e-6 Poise (1.013 bar and 0 °C)
Hazards
GHS labelling:
Pictograms GHS09: Environmental hazard
Signal word Warning
Hazard statements H411
Precautionary statements P273, P391, P410+P403, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Octafluorocyclobutane, or perfluorocyclobutane, C4F8, is an organofluorine compound which enjoys several niche applications. Octafluorocyclobutane is a colourless gas and shipped as a liquefied gas. It is the perfluorinated analogue of cyclobutane whereby all C–H bonds are replaced with C–F bonds.

Production

Octafluorocyclobutane is produced by the dimerization of tetrafluoroethylene and the reductive coupling of 1,2-dichloro-1,1,2,2-tetrafluoroethane.

Applications

In the production of semiconductor materials and devices, octafluorocyclobutane serves as a deposition gas and etchant. It has also been investigated as a refrigerant in specialised applications, as a replacement for ozone depleting chlorofluorocarbon refrigerants. Exploiting its volatility and chemical inertness, octafluorocyclobutane may be found in some aerosolized foods. It is listed by the Codex Alimentarius under number 946 (E946 for EU). It is investigated as a possible replacement for sulfur hexafluoride as a dielectric gas.

Gallery

  • PFC-318 measured by the Advanced Global Atmospheric Gases Experiment (AGAGE) in the lower atmosphere (troposphere) at stations around the world. Abundances are given as pollution free monthly mean mole fractions in parts-per-trillion. PFC-318 measured by the Advanced Global Atmospheric Gases Experiment (AGAGE) in the lower atmosphere (troposphere) at stations around the world. Abundances are given as pollution free monthly mean mole fractions in parts-per-trillion.

References

  1. Siegemund, Günter; Schwertfeger, Werner; Feiring, Andrew; Smart, Bruce; Behr, Fred; Vogel, Herward; McKusick, Blaine (2002). "Fluorine Compounds, Organic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a11_349. ISBN 978-3527306732..
  2. "Octafluorocyclobutane (RC318)". Gas Encyclopaedia. Air Liquide. Retrieved May 15, 2013.

Appendix

Its critical point is at 115.3 °C and 2.79 MPa.

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