Nitrosylsulfuric acid: Difference between revisions
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|Name = Nitrosylsulfuric acid |
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|ImageFile = Nitrosylsulfuric acid structure.svg |
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|Section1={{Chembox Identifiers |
|Section1={{Chembox Identifiers |
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|SMILES = O=NOS(=O)(=O)O |
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|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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|ChemSpiderID = 74147 |
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|PubChem = 82157 |
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|InChI = 1/HNO5S/c2-1-6-7(3,4)5/h(H,3,4,5) |
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|InChIKey = VQTGUFBGYOIUFS-UHFFFAOYAM |
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|StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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|StdInChI = 1S/HNO5S/c2-1-6-7(3,4)5/h(H,3,4,5) |
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|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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|StdInChIKey = VQTGUFBGYOIUFS-UHFFFAOYSA-N |
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|CASNo_Ref = {{cascite|correct|??}} |
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|CASNo = 7782-78-7 |
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|UNII_Ref = {{fdacite|correct|FDA}} |
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|UNII = 40K942UPM8 |
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|Section2={{Chembox Properties |
|Section2={{Chembox Properties |
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|Formula = {{chem2|HSO4NO}} |
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|MolarMass = 127.08 g/mol |
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|Appearance = Pale yellow crystals<ref name=EROS>{{cite book |chapter= Nitrosylsulfuric Acid |author= George A. Olah, G. K. Surya Prakash, Qi Wang, Xing-Ya Li |title= Encyclopedia of Reagents for Organic Synthesis |doi= 10.1002/047084289X.rn060 |journal= E-EROS Encyclopedia of Reagents for Organic Synthesis |year= 2001 |isbn= 978-0471936237}}</ref> |
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|Density = 1.865 g/mL in<br/> 40% sulfuric acid soln <ref>{{cite web |url=https://www.sigmaaldrich.com/AT/de/product/aldrich/517070 | title=Nitrosylsulfuric acid solution | publisher=Merck}}</ref> |
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|Solubility = Decomposes |
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|SolubleOther = Soluble in [[sulfuric acid|H<sub>2</sub>SO<sub>4</sub>]]<ref name=EROS/> |
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|MeltingPtC = 70 |
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|MeltingPt_ref = <ref name=EROS/> |
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|BoilingPt = Decomposes |
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|Section8={{Chembox Related |
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|OtherAnions = [[Nitrosyl chloride|NOCl]] |
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|OtherCations = [[Sodium bisulfate|NaHSO<sub>4</sub>]] |
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|OtherCompounds = [[Nitrosyl tetrafluoroborate|NOBF<sub>4</sub>]] |
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'''Nitrosylsulfuric acid''' is the [[chemical compound]] with the formula |
'''Nitrosylsulfuric acid''' is the [[chemical compound]] with the formula {{chem2|HSO4NO}}. It is a colourless solid that is used industrially in the production of [[caprolactam]],<ref name=Ullmann>{{cite encyclopedia |author1=Ritz, J. |author2=Fuchs, H. |author3=Kieczka, H. |author4=Moran, W. C. |encyclopedia= Ullmann's Encyclopedia of Industrial Chemistry |publisher= Wiley-VCH |location= Weinheim |year= 2002 |doi= 10.1002/14356007.a05_031 |chapter=Caprolactam |isbn=978-3527306732}}</ref> and was formerly part of the [[lead chamber process]] for producing [[sulfuric acid]]. The compound is the mixed [[inorganic anhydride|anhydride]] of sulfuric acid and [[nitrous acid]]. |
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In organic chemistry, it is used as a reagent for [[nitrosylation|nitrosating]], as a [[diazotization|diazotizing agent]], and as an [[oxidizing agent]].<ref name=EROS/> |
In organic chemistry, it is used as a reagent for [[nitrosylation|nitrosating]], as a [[diazotization|diazotizing agent]], and as an [[oxidizing agent]].<ref name=EROS/> |
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==Synthesis and reactions== |
==Synthesis and reactions== |
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A typical procedure entails dissolving [[sodium nitrite]] in cold sulfuric acid:<ref>{{ |
A typical procedure entails dissolving [[sodium nitrite]] in cold sulfuric acid:<ref>{{OrgSynth |author1=Hodgson, H. H.|author2=Mahadevan, A. P.|author3=Ward, E. R. |title= 1,4-Dinitronaphthalene |collvol= 3 |collvolpages= 341 |prep= cv3p0341 |year= 1955}} (diazodization followed by treatment with nitrite)</ref><ref>{{OrgSynth |author1=Sandin, R. B.|author2=Cairns, T. L. |title= 1,2,3-Triiodo-5-nitrobenzene |collvol= 2 |collvolpages= 604 |year= 1943 |prep= cv2p0604}} (diazodization followed by treatment with iodide)</ref> |
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:{{chem2 | HNO2 + H2SO4 -> HSO4NO + H2O }} |
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| ⚫ | It can also be prepared by the reaction of [[nitric acid]] and [[sulfur dioxide]].<ref>{{Cite book |author1=Coleman, G. H. |author2=Lillis, G. A. |author3=Goheen, G. E. |chapter=Nitrosyl Chloride |title= Inorganic Syntheses |year= 1939 |volume= 1 |pages= 55–59 |doi= 10.1002/9780470132326.ch20 |isbn=9780470132326}} This procedure generates the nitrosylsulfuric acid as an intermediate en route to NOCl.</ref> |
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:HNO<sub>2</sub> + H<sub>2</sub>SO<sub>4</sub> → NOHSO<sub>4</sub> + H<sub>2</sub>O |
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| ⚫ | It can also be prepared by the reaction of [[nitric acid]] and [[sulfur dioxide]].<ref>{{ |
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In industry, the nitrosodecarboxylation reaction between nitrosylsulfuric acid and [[cyclohexanecarboxylic acid]] is used to generate caprolactam:<ref name=Ullmann/> |
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:[[File:Nitrosodecarboxylation_Caprolactam_Synthesis.svg|500px]] |
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==Safety== |
==Safety== |
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[[Category:Hydrogen compounds]] |
[[Category:Hydrogen compounds]] |
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[[Category:Nitrosyl compounds]] |
[[Category:Nitrosyl compounds]] |
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[[Category: |
[[Category:Sulfate esters]] |
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[[Category:Sulfur oxoacids]] |
[[Category:Sulfur oxoacids]] |
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[[Category:Nitrogen(III) compounds]] |
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Latest revision as of 12:59, 22 June 2024
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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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| UNII | |
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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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.
In organic chemistry, it is used as a reagent for nitrosating, as a diazotizing agent, and as an oxidizing agent.[1]
Synthesis and reactions
[edit]A 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
[edit]Nitrosylsulfuric 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.