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Nitrosylsulfuric acid

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Nitrosylsulfuric acid
Structural formula of nitrosylsulfuric acid
Ball-and-stick model of the nitrosylsulfuric acid molecule
Names
IUPAC name Nitrosylsulfuric acid
Other names nitrosonium bisulfate, chamber crystals
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.029.058 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/HNO5S/c2-1-6-7(3,4)5/h(H,3,4,5)Key: VQTGUFBGYOIUFS-UHFFFAOYSA-N
  • InChI=1/HNO5S/c2-1-6-7(3,4)5/h(H,3,4,5)Key: VQTGUFBGYOIUFS-UHFFFAOYAM
SMILES
  • O=NOS(=O)(=O)O
Properties
Chemical formula HSO4NO
Molar mass 127.08 g/mol
Appearance Pale yellow crystals
Density 1.865 g/mL in
40% sulfuric acid soln
Melting point 70 °C (158 °F; 343 K)
Boiling point Decomposes
Solubility in water Decomposes
Solubility Soluble in H2SO4
Hazards
Occupational safety and health (OHS/OSH):
Main hazards Oxidizer
Related compounds
Other anions NOCl
Other cations NaHSO4
Related compounds NOBF4
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
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, 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.

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

Synthesis and reactions

A typical procedure entails dissolving sodium nitrite in cold sulfuric acid:

HNO2 + H2SO4 → HSO4NO + H2O

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

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: This is known as the Snia Viscosa process

Safety

Nitrosylsulfuric acid is a hazardous material and precautions are indicated.

References

  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. "Nitrosylsulfuric acid solution". Merck.
  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. 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. 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. 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.
Hydrogen compounds
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