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Chlorosulfuric acid
Chlorosulfuric acid is ClSO2OH. This tetrahedral molecule is an intermediate, chemically and conceptually, between SO2Cl2 and H2SO4. It is also known as chlorosulfonic acid. It is a distilable, colorless liquid that should be handled with care. It is a hygroscopic and a powerful lachrymator. Additional recommended knowledge
SynthesisThe industrial synthesis entails the reaction of hydrogen chloride with a solution of sulfur trioxide in sulfuric acid:
It can also be prepared by chlorination of sulfuric acid, written here for pedagogical purposes as SO2(OH)2, vs. the usual format H2SO4:
The latter method is more suited for laboratory-scale operations. Related compounds
ApplicationsClSO2OH is used to prepare sulfonic acids, which are useful in detergents and as chemical intermediates.
An early synthesis of saccharin begins with the reaction of toluene with ClSO2OH to give the ortho- and para-toluene sulfonyl chloride derivatives:
Oxidation of the ortho isomer gives the benzoic acid derivative that then is cyclized with ammonia and neutralized with base to afford saccharin. Safety considerationsClSO2OH reacts violently with water to release HCl. Inhalation of ClSO2OH would generate HCl in the lungs, which is very dangerous. Thus, precautions associated with HCl should be observed. References
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This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Chlorosulfuric_acid". A list of authors is available in Wikipedia. |