Swarts fluorination
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Swarts fluorination is a process whereby the
chlorine Chlorine is a chemical element with the symbol Cl and atomic number 17. The second-lightest of the halogens, it appears between fluorine and bromine in the periodic table and its properties are mostly intermediate between them. Chlorine i ...
atom Every atom is composed of a nucleus and one or more electrons bound to the nucleus. The nucleus is made of one or more protons and a number of neutrons. Only the most common variety of hydrogen has no neutrons. Every solid, liquid, gas, ...
s in a compound – generally an organic compound, but experiments have been performed using
silane Silane is an inorganic compound with chemical formula, . It is a colourless, pyrophoric, toxic gas with a sharp, repulsive smell, somewhat similar to that of acetic acid. Silane is of practical interest as a precursor to elemental silicon. Sila ...
s – are replaced with fluorine, by treatment with
antimony trifluoride Antimony trifluoride is the inorganic compound with the formula SbF3. Sometimes called Swarts' reagent, is one of two principal fluorides of antimony, the other being SbF5. It appears as a white solid. As well as some industrial applications, i ...
in the presence of chlorine or of
antimony pentachloride Antimony pentachloride is a chemical compound with the formula SbCl5. It is a colourless oil, but typical samples are yellowish due to dissolved chlorine. Owing to its tendency to hydrolyse to hydrochloric acid, SbCl5 is a highly corrosive substa ...
. Some metal fluorides are particularly more useful than others, including silver(I) fluoride, mercurous fluoride, cobalt(II) fluoride and aforementioned antimony. Heating the mixture of the metal fluoride and the haloalkane (chlorine and bromine are replaced readily) yields the desired fluoro-alkane. In some particularly reactive cases, heating is unnecessary; shaking or stirring the reaction mixture is sufficient. This reaction has a good yield. The active species is antimony trifluorodichloride, which is produced
in situ ''In situ'' (; often not italicized in English) is a Latin phrase that translates literally to "on site" or "in position." It can mean "locally", "on site", "on the premises", or "in place" to describe where an event takes place and is used in ...
; this compound can also be produced in bulk, according to a patent of John Weaver. The process was initially described by Frédéric Jean Edmond Swarts in 1892.Acad. Roy. Belg 3(24) p.474 (1892)


References

Halogenation reactions Substitution reactions Name reactions {{Chem-stub