Editing Fluorocarbon (section)

==Perfluoroaromatic compounds==
Perfluoroaromatic compounds contain only carbon and fluorine, like other fluorocarbons, but also contain an aromatic ring. The three most important examples are [[hexafluorobenzene]], [[Perfluorotoluene|octafluorotoluene]], and octafluoronaphthalene.
<gallery caption="Perfluoroaromatic compounds" widths="150px" heights="120px" perrow="5">
File:hexafluorobenzene.svg|[[Hexafluorobenzene]]
</gallery>

Perfluoroaromatic compounds can be manufactured via the Fowler process, like fluoroalkanes, but the conditions must be adjusted to prevent full fluorination. They can also be made by heating the corresponding perchloroaromatic compound with potassium fluoride at high temperature (typically 500&nbsp;°C), during which the chlorine atoms are replaced by fluorine atoms. A third route is defluorination of the fluoroalkane; for example, octafluorotoluene can be made from [[perfluoromethylcyclohexane]] by heating to 500&nbsp;°C with a nickel or iron catalyst.<ref>{{cite book |last=Banks|first=RE|date=1970|title=Fluorocarbons and their Derivatives, Second Edition|location=London|publisher=MacDonald & Co. (Publishers) Ltd.|pages=203–207|isbn=978-0-356-02798-2}}</ref>

Perfluoroaromatic compounds are relatively volatile for their molecular weight, with melting and boiling points similar to the corresponding aromatic compound, as the table below shows. They have high density and are non-flammable. For the most part, they are colorless liquids. Unlike the perfluoralkanes, they tend to be [[miscible]] with common solvents.{{citation needed|date=May 2017}}

{| class="wikitable"
|-
! Compound
! Melting point (°C)
! Boiling point (°C)
|-
| Hexafluorobenzene
| 5.3
| 80.5
|-
| [[Benzene]]
| 5.5
| 80.1
|-
|-
| Octafluorotoluene
| <−70
| 102–103
|-
| [[Toluene]]
| −95
| 110.6
|-
| Perfluoro(ethylbenzene)
|
| 114–115
|-
| [[Ethylbenzene]]
| −93.9
| 136.2
|-
| Octafluoronaphthalene
| 86–87
| 209<ref>{{cite web|url=http://www.chemspider.com/Chemical-Structure.60886.html|title=Octafluoronaphthalene|publisher=ChemSpider}}</ref>
|-
| [[Naphthalene]]
| 80.2
| 217.9
|}