Fluorocarbon
Fluorocarbons are chemical compounds with carbon-fluorine bonds. Compounds that contain many C-F bonds often have distinctive properties, e.g., enhanced stability, volatility, and hydrophobicity. Several fluorocarbons and their derivatives are commercial polymers, refrigerants, drugs, and anesthetics.[1]
Nomenclature[edit]
Perfluorocarbons or PFCs, are organofluorine compounds with the formula CxFy, meaning they contain only carbon and fluorine.[2] The terminology is not strictly followed and many fluorine-containing organic compounds are also called fluorocarbons.[1] Compounds with the prefix perfluoro- are hydrocarbons, including those with heteroatoms, wherein all C-H bonds have been replaced by C-F bonds.[3] Fluorocarbons includes perfluoroalkanes, fluoroalkenes, fluoroalkynes, and perfluoroaromatic compounds.
Perfluoroalkanes[edit]
Chemical properties[edit]
Perfluoroalkanes are very stable because of the strength of the carbon–fluorine bond, one of the strongest in organic chemistry.[4]
Its strength is a result of the electronegativity of fluorine imparting partial ionic character through partial charges on the carbon and fluorine atoms, which shorten and strengthen the bond (compared to carbon-hydrogen bonds) through favorable covalent interactions. Additionally, multiple carbon–fluorine bonds increase the strength and stability of other nearby carbon–fluorine bonds on the same geminal carbon, as the carbon has a higher positive partial charge.[1] Furthermore, multiple carbon–fluorine bonds also strengthen the "skeletal" carbon–carbon bonds from the inductive effect.[1] Therefore, saturated fluorocarbons are more chemically and thermally stable than their corresponding hydrocarbon counterparts, and indeed any other organic compound. They are susceptible to attack by very strong reductants, e.g. Birch reduction and very specialized organometallic complexes.[5]
Fluorocarbons are colorless and have high density, up to over twice that of water. They are not miscible with most organic solvents (e.g., ethanol, acetone, ethyl acetate, and chloroform), but are miscible with some hydrocarbons (e.g., hexane in some cases). They have very low solubility in water, and water has a very low solubility in them (on the order of 10 ppm). They have low refractive indices.
Perfluoroaromatic compounds contain only carbon and fluorine, like other fluorocarbons, but also contain an aromatic ring. The three most important examples are hexafluorobenzene, octafluorotoluene, and octafluoronaphthalene.
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 °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 °C with a nickel or iron catalyst.[31]
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.