- Fluorosulfuric acid
Name = Fluorosulfuric acid
ImageFile = Fluorosulfuric-acid-2D.png
ImageName = Fluorosulfuric acid
ImageFile1 = Fluorosulfuric-acid-3D-vdW.png
ImageName1 = Fluorosulfuric acid
OtherNames = Fluorosulfonic acid,
Section1 = Chembox Identifiers
CASNo = 7789-21-1
EINECS = 232-149-4
RTECS = LP0715000
Section2 = Chembox Properties
Formula = FSO3H.
MolarMass = 100.0645 g/mol
Appearance = Colorless liquid
Density = 1.84 g/cm-3, liquid
Solubility = Soluble
MeltingPt = -87.3 °C
BoilingPt = 165.5 °C
pKa = -10
Section3 = Chembox Structure
MolShape = tetrahedral
Dipole = N/A
Section7 = Chembox Hazards
EUClass = 1777 Corrosive material
RPhrases = 20-35
SPhrases = 26-45
Section8 = Chembox Related
Fluorosulfuric acid is FSO3H; it is one of the strongest acids commercially available. It is also known by the alternative name, fluorosulfonic acid. The molecule is better described by the formula FSO2OH, which emphasizes its relationship to
sulfuric acid, H2SO4. FSO3H is a tetrahedral molecule.
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. Reflecting its strong acidity, it dissolves almost all organic compounds that are even weak proton acceptors. [ Encyclopedia of Reagents for Organic Synthesis 2001 John Wiley & Sons, Ltd] FSO3H hydrolyzes slowly to HF and sulfuric acid. The related triflic acidCF3SO3H retains the high acidity of FSO3H but is hydrolytically stable.
Fluorosulfuric acid is prepared by the reaction of HF and
sulfur trioxide::SO3 + HF → FSO3HAlternatively, KHF2 or CaF2 can be treated with oleumat 250 °C. Once freed from HF by sweeping with an inert gas, FSO3H can be distilled in a glass apparatus.Cotton, F.A.; Wilkinson, G. (1980) "Advanced Inorganic Chemistry: A Comprehensive Text", 4th Edition, p.246, Wiley-Interscience Publications.]
FSO3H is one of the strongest known simple
Brønsted acids, although recent work on carborane-based acids have led to still stronger acids. [M. Juhasz, S. Hoffmann, E. Stoyanov, K.-C. Kim, C. A. Reed, Angewandte Chemie International Edition43 5352 - 5355 2004.] It has an "H"0 value of −15.1 compared to −12 for sulfuric acid. The combination of FSO3H and the Lewis acid antimony pentafluorideproduces " Magic acid," which is a far stronger protonating agent. These acids all fall into the category of " superacids", acids stronger than 100% sulfuric acid.
alkanesand the alkylation of hydrocarbons with alkenes. [Olah, G.; Farooq, O.; Husain, A.; Ding, N.; Trivedi, N.; Olah, J. (1991) Superacid FSO3H/HF-Catalyzed Butane Isomerisation. Catalysis Letters 10, 239-248.] It can also be used as a laboratory fluorinating agent.
Fluorosulfuric acid is considered to be highly toxic and corrosive. It hydrolyzes to release HF. Addition of water to FSO3H can be violent, similar to the addition of water to sulfuric acid.
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