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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| Names | |
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| IUPAC name
Nitrosylsulfuric acid
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| Other names
nitrosonium bisulfate, chamber crystals
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| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.029.058 |
PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| HSO4NO | |
| 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
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Oxidizer |
| Related compounds | |
Other anions
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NOCl |
Other cations
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NaHSO4 |
Related compounds
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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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In organic chemistry, it is used as a reagent for nitrosating, as a diazotizing agent, and as an oxidizing agent.[1]
Synthesis and reactions
editA 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
editNitrosylsulfuric acid is a hazardous material and precautions are indicated.[1]
References
edit- ^ a b c d e 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) - ^ "Nitrosylsulfuric acid solution". Merck.
- ^ 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.
- ^ 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)
- ^ 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)
- ^ 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.