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Fluorosulfuric acid

Fluorosulphonic acid, Fluorinesulfonic acid, Fluorinesulphonic acid, Fluoridosulfonic acid, Fluoridosulphonic acid, Sulfuric fluorohydrin, Epoxysulfonyl fluoride | NFPA-H = 4 | NFPA-F = 0 | NFPA-R = 3 | NFPA-S = W+OX Trifluoromethanesulfonic acid Hydrofluoric acid Sulfurous acid Sulfuric acid Sulfur hexafluoride

Fluorosulfuric acid (IUPAC name: sulfurofluoridic acid) is the inorganic compound with the chemical formula . It is one of the strongest acids commercially available. It is a tetrahedral molecule and is closely related to sulfuric acid, , substituting a fluorine atom for one of the hydroxyl groups. It is a colourless liquid, although commercial samples are often yellow due to impurities.

Properties

Fluorosulfuric acid is a free-flowing colorless liquid. It is soluble in polar organic solvents (e.g. nitrobenzene, acetic acid, and ethyl acetate), but poorly soluble in nonpolar solvents such as alkanes.

is one of the strongest known simple Brønsted acids. It has an H0 value of −15.1 compared to −12 for sulfuric acid. The combination of and the Lewis acid antimony pentafluoride produces "Magic acid", which is a far stronger protonating agent. These acids are categorized as "superacids", acids stronger than 100% sulfuric acid.

Reflecting its strong acidity, dissolves almost all organic compounds that are even weak proton acceptors. hydrolyzes slowly to hydrogen fluoride (HF) and sulfuric acid. The related triflic acid () retains the high acidity of but is more hydrolytically stable. The self-ionization of fluorosulfonic acid also occurs: : K = 4.0 × 10−8 (at 298 K)

isomerizes alkanes and catalyzes the alkylation of hydrocarbons with alkenes, although it is unclear if such applications are of commercial importance. It can also be used as a laboratory fluorinating agent.

Production

Fluorosulfuric acid is prepared by the reaction of HF and sulfur trioxide: : Alternatively, or can be treated with oleum at 250 °C. Once freed from HF by sweeping with an inert gas, HSO3F can be distilled in a glass apparatus.

Safety

Fluorosulfuric acid is considered to be highly toxic and extremely corrosive. It hydrolyzes to release HF. Addition of water to is similar to, and even more violent than, the addition of water to sulfuric acid.

References

References

  1. {{Sigma-Aldrich
  2. Erhardt Tabel, Eberhard Zirngiebl, Joachim Maas "Fluorosulfuric Acid" in "Ullmann's Encyclopedia of Industrial Chemistry" 2005, Wiley-VCH, Weinheim. {{doi. 10.1002/14356007.a11_431
  3. Christopher A. Reed "Myths about the Proton. The Nature of H+ in Condensed Media" Acc. Chem. Res., 2013, 46 (11), pp 2567–2575. {{doi. 10.1021/ar400064q
  4. (2001). "Encyclopedia of Reagents for Organic Synthesis". John Wiley & Sons.
  5. (1991). "Superacid HSO3F/HF-Catalyzed Butane Isomerisation". Catalysis Letters.
  6. (1980). "Advanced Inorganic Chemistry". Wiley.
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sulfuryl-compounds fluoro-complexes superacids mineral-acids fluorinating-agents sulfur-oxoacids
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