Octafluorocyclobutane

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.

Octafluorocyclobutane
Structural formula of octafluorocyclobutane
Ball-and-stick of the octafluorocyclobutane molecule
Names
Preferred IUPAC name
Octafluorocyclobutane
Other names
Freon-C-318, perfluorocyclobutane
Identifiers
3D model (JSmol)
1909266
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.705
EC Number
  • 204-075-2
E number E946 (glazing agents, ...)
131113
UNII
  • InChI=1S/C4F8/c5-1(6)2(7,8)4(11,12)3(1,9)10 ☒N
    Key: BCCOBQSFUDVTJQ-UHFFFAOYSA-N ☒N
  • InChI=1/C4F8/c5-1(6)2(7,8)4(11,12)3(1,9)10
    Key: BCCOBQSFUDVTJQ-UHFFFAOYAW
  • C1(C(C(C1(F)F)(F)F)(F)F)(F)F
Properties
C4F8
Molar mass 200.03 g/mol
Appearance colourless gas
Density 1.637 g/cm3 at −5.8 °C (liquid)

9.97 kg/m3 at −6 °C and 1 atm (gas)
8.82 kg/m3 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)
0.016 vol/vol (1.013 bar and 20 °C)
Viscosity 109e-6 Poise (1.013 bar and 0 °C)
Hazards
GHS labelling:
GHS04: Compressed GasGHS09: Environmental hazard
Warning
H280, H411
P273, P391, P410+P403, 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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Infobox references

Production

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

Applications

In the production of semiconductor materials and devices, octafluorocyclobutane serves as a deposition gas and etchant.[2] 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.

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..
  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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