Nitrosylsulfuric_acid

Nitrosylsulfuric acid

Nitrosylsulfuric acid

Chemical compound

Nitrosylsulfuric acid is the chemical compound with the formula HSO4NO. It is a colourless solid that is used industrially in the production of caprolactam,[3] and was formerly part of the lead chamber process for producing sulfuric acid. The compound is the mixed anhydride of sulfuric acid and nitrous acid.

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In organic chemistry, it is used as a reagent for nitrosating, as a diazotizing agent, and as an oxidizing agent.[1]

Synthesis and reactions

A typical procedure entails dissolving sodium nitrite in cold sulfuric acid:[4][5]

HNO2 + H2SO4 → HSO4NO + H2O

It can also be prepared by the reaction of nitric acid and sulfur dioxide.[6]

HSO4NO is used in organic chemistry to prepare diazonium salts from amines, for example in the Sandmeyer reaction. Related NO-delivery reagents include nitrosonium tetrafluoroborate [NO]+[BF4]− and nitrosyl chloride.

In industry, the nitrosodecarboxylation reaction between nitrosylsulfuric acid and cyclohexanecarboxylic acid is used to generate caprolactam:[3]

Safety

Nitrosylsulfuric acid is a hazardous material and precautions are indicated.[1]

References

  1. [1]
    George A. Olah, G. K. Surya Prakash, Qi Wang, Xing-Ya Li (2001). "Nitrosylsulfuric Acid". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rn060. ISBN 978-0471936237. {{cite book}}: |journal= ignored (help)CS1 maint: multiple names: authors list (link)
  2. [2]
    "Nitrosylsulfuric acid solution". Merck.
  3. [3]
    Ritz, J.; Fuchs, H.; Kieczka, H.; Moran, W. C. (2002). "Caprolactam". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a05_031. ISBN 978-3527306732.
  4. [4]
    Hodgson, H. H.; Mahadevan, A. P.; Ward, E. R. (1955). "1,4-Dinitronaphthalene". Organic Syntheses; Collected Volumes, vol. 3, p. 341. (diazodization followed by treatment with nitrite)
  5. [5]
    Sandin, R. B.; Cairns, T. L. (1943). "1,2,3-Triiodo-5-nitrobenzene". Organic Syntheses; Collected Volumes, vol. 2, p. 604. (diazodization followed by treatment with iodide)
  6. [6]
    Coleman, G. H.; Lillis, G. A.; Goheen, G. E. (1939). Nitrosyl Chloride. Inorganic Syntheses. Vol. 1. pp. 55–59. doi:10.1002/9780470132326.ch20. ISBN 9780470132326. This procedure generates the nitrosylsulfuric acid as an intermediate en route to NOCl.
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