Nitrosylsulfuric acid

Nitrosylsulfuric acid
Names
IUPAC name
Nitrosylsulfuric acid
Other names
nitrosonium bisulfate, chamber crystals
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.029.058
UNII
  • InChI=1S/HNO5S/c2-1-6-7(3,4)5/h(H,3,4,5) Y
    Key: VQTGUFBGYOIUFS-UHFFFAOYSA-N Y
  • InChI=1/HNO5S/c2-1-6-7(3,4)5/h(H,3,4,5)
    Key: VQTGUFBGYOIUFS-UHFFFAOYAM
  • O=NOS(=O)(=O)O
Properties
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
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).
Y verify (what is YN ?)
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.
This article is issued from Wikipedia. The text is available under Creative Commons Attribution-Share Alike 4.0 unless otherwise noted. Additional terms may apply for the media files.