Chemistry:Nitrosylsulfuric 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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PubChem CID
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| Properties | |
| HSO 4NO | |
| 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 | |
| Main hazards | 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). | |
 verify (what is   ?)
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| Infobox references | |
Nitrosylsulfuric acid is the chemical compound with the formula HSO
4NO. 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.
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]
- HNO
2 + H
2SO
4 → HSO
4NO + H
2O
It can also be prepared by the reaction of nitric acid and sulfur dioxide.[6]
HSO
4NO 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]+
[BF
4]−
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
- ↑ 1.0 1.1 1.2 1.3 1.4 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.
- ↑ "Nitrosylsulfuric acid solution". Merck. https://www.sigmaaldrich.com/AT/de/product/aldrich/517070.
- ↑ 3.0 3.1 Ritz, J.; Fuchs, H.; Kieczka, H.; Moran, W. C. (2002). 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. http://www.orgsyn.org/demo.aspx?prep=cv3p0341.; Collective Volume, 3, pp. 341 (diazodization followed by treatment with nitrite)
- ↑ Sandin, R. B.; Cairns, T. L. (1943). "1,2,3-Triiodo-5-nitrobenzene". Organic Syntheses. http://www.orgsyn.org/demo.aspx?prep=cv2p0604.; Collective Volume, 2, pp. 604 (diazodization followed by treatment with iodide)
- ↑ Coleman, G. H.; Lillis, G. A.; Goheen, G. E. (1939). Nitrosyl Chloride. Inorganic Syntheses. 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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