Nitrosylsulfuric acid
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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UNII | |
CompTox Dashboard (EPA)
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Properties | |
HNO5S | |
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). | |
what is ?) | (|
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 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]
- HNO2 + H2SO4 → NOHSO4 + H2O
It can also be prepared by the reaction of nitric acid and sulfur dioxide.[6]
NOHSO4 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[]
Nitrosylsulfuric acid is a hazardous material and precautions are indicated.[1]
References[]
- ^ Jump up to: a b c d e George A. Olah, G. K. Surya Prakash, Qi Wang, Xing-Ya Li (2001). Nitrosylsulfuric Acid. E-EROS Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rn060. ISBN 978-0471936237.CS1 maint: multiple names: authors list (link)
- ^ https://www.sigmaaldrich.com/AT/de/product/aldrich/517070. Missing or empty
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(help) - ^ Jump up to: 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.; Collective Volume, 3, p. 341 (diazodization followed by treatment with nitrite)
- ^ Sandin, R. B.; Cairns, T. L. (1943). "1,2,3-Triiodo-5-nitrobenzene". Organic Syntheses.; Collective Volume, 2, p. 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.
- Acid anhydrides
- Acids
- Hydrogen compounds
- Nitrosyl compounds
- Sulfate esters
- Sulfur oxoacids
- Nitrogen(III) compounds