Chlorosulfuric acid

Chlorosulfuric acid

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Encyclopedia
Chlorosulfuric 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 HSO3Cl. It is also known as chlorosulfonic acid. It is a distillable, colorless liquid that should be handled with care. It is a hygroscopic and a powerful lachrymator
Lachrymatory agent
Tear gas, formally known as a lachrymatory agent or lachrymator , is a non-lethal chemical weapon that stimulates the corneal nerves in the eyes to cause tears, pain, and even blindness...

.

Structure and properties


Chlorosulfuric acid is a tetrahedral molecule. The formula is more descriptively written SO2(OH)Cl, but HSO3Cl is traditional. It is an intermediate, chemically and conceptually, between sulfuryl chloride
Sulfuryl chloride
Sulfuryl chloride is an inorganic compound with the formula SO2Cl2. At room temperature, it is a colorless liquid with a pungent odor. Sulfuryl chloride is not found in nature, as can be inferred from its rapid hydrolysis....

 (SO2Cl2) 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...

 (H2SO4). The compound is rarely obtained pure. Upon standing with excess sulfur trioxide, it decomposes to pyrosulfuryl chlorides:
2 ClSO3H + SO3 → H2SO4 + S2O5Cl2

Synthesis


The industrial synthesis entails the reaction of hydrogen chloride
Hydrogen chloride
The compound hydrogen chloride has the formula HCl. At room temperature, it is a colorless gas, which forms white fumes of hydrochloric acid upon contact with atmospheric humidity. Hydrogen chloride gas and hydrochloric acid are important in technology and industry...

 with a solution of 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...

 in sulfuric acid:
HCl + SO3 → ClSO3H

It can also be prepared by chlorination of sulfuric acid, written here for pedagogical purposes as SO2(OH)2, vs. the usual format H2SO4:
PCl5 + SO2(OH)2 → ClSO3H + POCl3 + HCl

The latter method is more suited for laboratory-scale operations.

Applications


ClSO2OH is used to prepare sulfonic acids, which are useful in detergents and as chemical intermediates:
ROH + ClSO3H → ROSO3H + HCl


An early synthesis of saccharin
Saccharin
Saccharin is an artificial sweetener. The basic substance, benzoic sulfilimine, has effectively no food energy and is much sweeter than sucrose, but has a bitter or metallic aftertaste, especially at high concentrations...

 begins with the reaction of toluene with ClSO2OH to give the ortho- and para-toluene sulfonyl chloride derivatives:
CH3C6H5 + 2ClSO2OH → CH3C6H4SO2Cl + H2SO4

Oxidation of the ortho isomer gives the benzoic acid
Benzoic acid
Benzoic acid , C7H6O2 , is a colorless crystalline solid and the simplest aromatic carboxylic acid. The name derived from gum benzoin, which was for a long time the only source for benzoic acid. Its salts are used as a food preservative and benzoic acid is an important precursor for the synthesis...

 derivative that then is cyclized with ammonia and neutralized with base to afford saccharin.

Safety


ClSO3H reacts violently with water to yield sulfuric acid and HCl. Precautions associated with HCl should be observed.

Related halosulfuric acids

  • FSO2OH is a related strong acid with a diminished tendency to evolve HF.
  • Bromosulfonic acid, BrSO2OH, is unstable, decomposing at its melting point of 8°C to give Br2, SO2, and H2SO4.
  • Iodosulfonic acid is unknown.