Nitrosylsulfuric acid

Nitrosylsulfuric acid
Structural formula of nitrosylsulfuric acid
Names
IUPAC name
Nitrosylsulfuric acid
Other names
nitrosonium bisulfate, chamber crystals
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.029.058
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/HNO5S/c2-1-6-7(3,4)5/h(H,3,4,5) checkY
    Key: VQTGUFBGYOIUFS-UHFFFAOYSA-N checkY
  • 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
 NOHSO4
Molar mass 127.08 g/mol
Appearance Pale yellow crystals[1]
Density 1.865 g/mL in
40% sulfuric acid soln [2]
Melting point 70 °C (158 °F; 343 K)[1]
Boiling point Decomposes
Solubility in water
 Decomposes
Solubility Soluble in H2SO4[1]
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 [77 °F], 100 kPa).
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Infobox references

Nitrosylsulfuric acid is the chemical compound with the formula NOHSO4. 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 a salt best described as NO+HSO4− (nitrosonium hydrogensulfate).[4] It is called “lead-chamber crystals”.

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:[5][6]

HNO2 + H2SO4 → NOHSO4 + H2O

It can also be prepared by the reaction of nitric acid and sulfur dioxide.[7]

NOHSO4 is used in organic chemistry to prepare diazonium salts from amines,[5][6] 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] This conversion illustrates the Snia Viscosa process

References

  1. ^ a b c d Olah, George A.; Prakash, G. K. Surya; Wang, Qi; Li, Xing-Ya (2001). "Nitrosylsulfuric Acid". E-EROS Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rn060.
  2. ^ "Nitrosylsulfuric acid solution". Merck.
  3. ^ a b 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. ^ Beck, Daniel; Belz, Anja; In‐Iam, Areenan; Mayer, Peter; Klüfers, Peter (2017-10-04). "NO(HSO4), a Fairly Ionic Solid". Zeitschrift für Anorganische und Allgemeine Chemie. 643 (18): 1191–1194. doi:10.1002/zaac.201700274. ISSN 0044-2313.
  5. ^ a b Hodgson, H. H.; Mahadevan, A. P.; Ward, E. R. (1948). "1,4-Dinitronaphthalene". Organic Syntheses. 28: 52. doi:10.15227/orgsyn.028.0052. (diazodization followed by treatment with nitrite)
  6. ^ a b Sandin, R. B.; Cairns, T. L. (1939). "1,2,3-Triiodo-5-nitrobenzene". Organic Syntheses. 19: 81. doi:10.15227/orgsyn.019.0081. (diazodization followed by treatment with iodide)
  7. ^ Coleman, G. H.; Lillis, G. A.; Goheen, G. E. (2007) [1st pub. 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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