Fluorosulfuric acid
Encyclopedia
Fluorosulfuric acid is the inorganic compound
Inorganic compound
Inorganic compounds have traditionally been considered to be of inanimate, non-biological origin. In contrast, organic compounds have an explicit biological origin. However, over the past century, the classification of inorganic vs organic compounds has become less important to scientists,...

 with the formula
Chemical formula
A chemical formula or molecular formula is a way of expressing information about the atoms that constitute a particular chemical compound....

 HSO3F. It is one of the strongest acids commercially available and is a superacid
Superacid
According to the classical definition superacid is an acid with an acidity greater than that of 100% pure sulfuric acid, which has a Hammett acidity function of −12. According to the modern definition, superacid is a medium, in which the chemical potential of the proton is higher than in pure...

. The formula HFSO3 emphasizes its relationship to sulfuric acid
Sulfuric acid
Sulfuric acid is a strong mineral acid with the molecular formula . Its historical name is oil of vitriol. Pure sulfuric acid is a highly corrosive, colorless, viscous liquid. The salts of sulfuric acid are called sulfates...

, H2SO4; HSO3F is a tetrahedral molecule.

Chemical properties

Fluorosulfuric acid is a free-flowing colorless liquid. It is soluble in polar organic solvents (e.g. nitrobenzene
Nitrobenzene
Nitrobenzene is an organic compound with the chemical formula C6H5NO2. It is a water-insoluble pale yellow oil with an almond-like odor. It freezes to give greenish-yellow crystals. It is produced on a large scale as a precursor to aniline. Although occasionally used as a flavoring or perfume...

, acetic acid
Acetic acid
Acetic acid is an organic compound with the chemical formula CH3CO2H . It is a colourless liquid that when undiluted is also called glacial acetic acid. Acetic acid is the main component of vinegar , and has a distinctive sour taste and pungent smell...

, and ethyl acetate
Ethyl acetate
Ethyl acetate is the organic compound with the formula CH3COOCH2CH3. This colorless liquid has a characteristic sweet smell and is used in glues, nail polish removers, and cigarettes...

), 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. FSO3H hydrolyze
Hydrolysis
Hydrolysis is a chemical reaction during which molecules of water are split into hydrogen cations and hydroxide anions in the process of a chemical mechanism. It is the type of reaction that is used to break down certain polymers, especially those made by condensation polymerization...

s slowly to HF and sulfuric acid
Sulfuric acid
Sulfuric acid is a strong mineral acid with the molecular formula . Its historical name is oil of vitriol. Pure sulfuric acid is a highly corrosive, colorless, viscous liquid. The salts of sulfuric acid are called sulfates...

. The related triflic acid (CF3SO3H) retains the high acidity of FSO3H but is more hydrolytically stable.

Production

Fluorosulfuric acid is prepared by the reaction of HF and sulfur trioxide
Sulfur trioxide
Sulfur trioxide is the chemical compound with the formula SO3. In the gaseous form, this species is a significant pollutant, being the primary agent in acid rain. It is prepared on massive scales as a precursor to sulfuric acid.-Structure and bonding:Gaseous SO3 is a trigonal planar molecule of...

:
SO3 + HF → FSO3H

Alternatively, KHF2 or CaF2 can be treated with oleum
Oleum
Oleum , or fuming sulfuric acid refers to a solution of various compositions of sulfur trioxide in sulfuric acid or sometimes more specifically to disulfuric acid ....

 at 250 °C. Once freed from HF by sweeping with an inert gas, FSO3H can be distilled in a glass apparatus.

Super-acids

FSO3H is one of the strongest known simple Brønsted acids, although recent work on carborane
Carborane
A carborane is a cluster composed of boron and carbon atoms. Like many of the related boranes, these clusters are polyhedra and are similarly classified as closo-, nido-, arachno-, hypho-, etc...

-based acids have led to still stronger acids. It has an H0 value of −15.1 compared to −12 for sulfuric acid. The combination of FSO3H and the Lewis acid
Lewis acid
]The term Lewis acid refers to a definition of acid published by Gilbert N. Lewis in 1923, specifically: An acid substance is one which can employ a lone pair from another molecule in completing the stable group of one of its own atoms. Thus, H+ is a Lewis acid, since it can accept a lone pair,...

 antimony pentafluoride
Antimony pentafluoride
Antimony pentafluoride is the inorganic compound with the formula SbF5. This colourless, viscous liquid is a valuable Lewis acid and a component of the superacid fluoroantimonic acid, the strongest known acid...

 produces "Magic acid
Magic acid
Magic acid , is a superacid consisting of a mixture, most commonly in a 1:1 molar ratio, of fluorosulfonic acid and antimony pentafluoride...

," which is a far stronger protonating agent. These acids all fall into the category of "superacids", acids stronger than 100% sulfuric acid.

Applications

FSO3H is useful for regenerating mixtures of HF and H2SO4 for etching lead glass
Lead glass
Lead glass is a variety of glass in which lead replaces the calcium content of a typical potash glass. Lead glass contains typically 18–40 weight% lead oxide , while modern lead crystal, historically also known as flint glass due to the original silica source, contains a minimum of 24% PbO...

.

FSO3H isomerizes alkanes and 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.

Safety

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. Addition of fluorosulfuric acid to water is much more violent process than addition of sulfuric acid.
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