Nitrosylsulfuric acid
{{Chembox
|Watchedfields = changed
|verifiedrevid = 434912557
|Name = Nitrosylsulfuric acid
|ImageFile = Nitrosylsulfuric acid structure.svg
|ImageAlt = Structural formula of nitrosylsulfuric acid
|ImageFile1 = Nitrosylsulfuric acid molecule ball.png
|ImageSize1 = 190px
|ImageAlt1 = Ball-and-stick model of the nitrosylsulfuric acid molecule
|IUPACName = Nitrosylsulfuric acid
|OtherNames = nitrosonium bisulfate, chamber crystals
|Section1={{Chembox Identifiers
|SMILES = O=NOS(=O)(=O)O
|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
|ChemSpiderID = 74147
|PubChem = 82157
|InChI = 1/HNO5S/c2-1-6-7(3,4)5/h(H,3,4,5)
|InChIKey = VQTGUFBGYOIUFS-UHFFFAOYAM
|StdInChI_Ref = {{stdinchicite|correct|chemspider}}
|StdInChI = 1S/HNO5S/c2-1-6-7(3,4)5/h(H,3,4,5)
|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
|StdInChIKey = VQTGUFBGYOIUFS-UHFFFAOYSA-N
|CASNo_Ref = {{cascite|correct|??}}
|CASNo = 7782-78-7
|UNII_Ref = {{fdacite|correct|FDA}}
|UNII = 40K942UPM8
}}
|Section2={{Chembox Properties
|Formula = {{chem2|HSO4NO}}
|MolarMass = 127.08 g/mol
|Appearance = Pale yellow crystals{{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}}
|Density = 1.865 g/mL in
40% sulfuric acid soln {{cite web |url=https://www.sigmaaldrich.com/AT/de/product/aldrich/517070 | title=Nitrosylsulfuric acid solution | publisher=Merck}}
|Solubility = Decomposes
|SolubleOther = Soluble in H2SO4
|MeltingPtC = 70
|BoilingPt = Decomposes
}}
|Section7={{Chembox Hazards
|MainHazards = Oxidizer
}}
|Section8={{Chembox Related
|OtherAnions = NOCl
|OtherCations = NaHSO4
|OtherCompounds = NOBF4
}}
}}
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,{{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}} 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.
Synthesis and reactions
A typical procedure entails dissolving sodium nitrite in cold sulfuric acid:{{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){{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)
:{{chem2 | HNO2 + H2SO4 -> HSO4NO + H2O }}
It can also be prepared by the reaction of nitric acid and sulfur dioxide.{{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.
{{chem2|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 {{chem2|[NO]+[BF4]-}} and nitrosyl chloride.
In industry, the nitrosodecarboxylation reaction between nitrosylsulfuric acid and cyclohexanecarboxylic acid is used to generate caprolactam: This is known as the Snia Viscosa process
Safety
References
{{Reflist}}
{{Hydrogen compounds}}