| Revision as of 04:53, 17 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 477239151 of page Chlorosulfuric_acid for the Chem/Drugbox validation project (updated: ''). |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{chembox |
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| Watchedfields = changed |
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| Watchedfields = changed |
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| verifiedrevid = 476998652 |
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| verifiedrevid = 477315288 |
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| Name = Chlorosulfuric acid |
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| Name = Chlorosulfuric acid |
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| ImageFile = Chlorosulfuric-acid.png |
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| ImageFileL1 = Chlorosulfuric-acid.png |
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| ImageSize = 150px |
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| ImageSizeL1 = 110px |
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| ImageAltL1 = Structural formula of chlorosulfuric acid |
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| ImageName = Chlorosulfuric acid |
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| ImageFile1 = Chlorosulfuric-acid-3D-balls.png |
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| ImageFileR1 = Chlorosulfuric acid molecule ball.png |
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| ImageSize1 = 180px |
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| ImageSizeR1 = 140px |
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| ImageAltR1 = Ball-and-stick model of the chlorosulfuric acid molecule |
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| ImageName1 = Chlorosulfuric acid |
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| IUPACName = Sulfurochloridic acid |
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| ImageFile2 = Chlorosulfuric acid.png |
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| IUPACName = Sulfurochloridic acid |
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| OtherNames = Chlorosulfuric acid,<br>Chlorosulfonic acid,<br>Chlorosulphonic acid,<br>Chlorinesulfonic acid,<br>Chlorinesulphonic acid,<br>Chloridosulfonic acid,<br>Chloridosulphonic acid,<br>Sulfuric chlorohydrin |
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| OtherNames = Chlorosulfuric acid,<br />Chlorosulfonic acid,<br />Chlorosulphonic acid,<br />Chlorinesulfonic acid,<br />Chlorinesulphonic acid,<br />Chloridosulfonic acid,<br />Chloridosulphonic acid,<br />Sulfuric chlorohydrin |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| SMILES = ClS(=O)(=O)O |
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| SMILES = ClS(=O)(=O)O |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 23040 |
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| ChemSpiderID = 23040 |
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| PubChem = 24638 |
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| PubChem = 24638 |
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| InChI = 1/ClHO3S/c1-5(2,3)4/h(H,2,3,4) |
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| InChI = 1/ClHO3S/c1-5(2,3)4/h(H,2,3,4) |
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| InChIKey = XTHPWXDJESJLNJ-UHFFFAOYAO |
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| InChIKey = XTHPWXDJESJLNJ-UHFFFAOYAO |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/ClHO3S/c1-5(2,3)4/h(H,2,3,4) |
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| StdInChI = 1S/ClHO3S/c1-5(2,3)4/h(H,2,3,4) |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = XTHPWXDJESJLNJ-UHFFFAOYSA-N |
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| StdInChIKey = XTHPWXDJESJLNJ-UHFFFAOYSA-N |
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| CASNo = 7790-94-5 |
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| CASNo = 7790-94-5 |
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| CASNo_Ref = {{cascite|changed|??}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| RTECS = FX5730000 |
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| UNII = 2O9AXL1TJ4 |
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| UNNumber = 1754 |
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| RTECS = FX5730000 |
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}} |
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| EC_number = 232-234-6 |
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| Section2 = {{Chembox Properties |
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| UNNumber = 1754 |
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| Formula = HSO<sub>3</sub>Cl |
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}} |
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| MolarMass = 116.52 g mol<sup>−1</sup> |
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|Section2={{Chembox Properties |
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| Appearance = colorless liquid that fumes in air |
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| Density = 1.753 g cm<sup>−3</sup> |
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| Formula = HSO<sub>3</sub>Cl |
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| MolarMass = 116.52 g mol<sup>−1</sup> |
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| Solubility = hydrolysis |
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| Appearance = colorless liquid, but commercial samples usually are pale brown |
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| Solvent = other solvents |
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| Density = 1.753 g cm<sup>−3</sup> |
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| SolubleOther = reacts with alcohols<br/>soluble in chlorocarbons |
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| Solubility = hydrolysis |
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| MeltingPt = −80 °C |
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| Solvent = other solvents |
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| BoilingPt = 151–152 °C<br/>({{convert|755|mmHg|abbr=on|disp=or}}) |
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| SolubleOther = reacts with alcohols<br/>soluble in chlorocarbons |
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| Viscosity = |
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| RefractIndex = 1.433 |
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| MeltingPtC = −80 |
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| BoilingPtC = 151 to 152 |
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}} |
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| BoilingPt_notes = ({{convert|755|mmHg|abbr=on|disp=or}}) |
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| Section3 = {{Chembox Structure |
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| pKa = −5.9 (in ])<ref name=P82db>{{cite book|title=Ionisation Constants of Inorganic Acids and Bases in Aqueous Solution|editor-first=D. D.|editor-last=Perrin|edition=2nd|series=] Chemical Data|issue=29|publisher=Pergamon|location=Oxford|year=1982|publication-date=1984|orig-date=1969|lccn=82-16524|isbn=0-08-029214-3|at=Entry 32}}</ref> |
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| MolShape = tetrahedral |
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| RefractIndex = 1.433 |
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| Dipole = |
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}} |
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}} |
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| Section7 = {{Chembox Hazards |
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|Section3={{Chembox Structure |
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| MolShape = tetrahedral |
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| ExternalMSDS = |
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| Dipole = |
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| EUClass = Corrosive ('''C''') |
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}} |
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| EUIndex = 016-017-00-1 |
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|Section7={{Chembox Hazards |
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| NFPA-H = 4 |
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| ExternalSDS = |
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| NFPA-F = 0 |
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| NFPA-R = 2 |
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| NFPA-H = 3 |
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| NFPA-O = W |
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| NFPA-F = 0 |
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| NFPA-R = 2 |
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| RPhrases = {{R14}}, {{R35}}, {{R37}} |
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| NFPA-S = WOX |
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| SPhrases = {{S2}}, {{S26}}, {{S45}} |
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| GHSPictograms = {{GHS05}}{{GHS07}} |
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}} |
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| GHSSignalWord = Danger |
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| Section8 = {{Chembox Related |
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| HPhrases = {{H-phrases|314|335}} |
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| OtherCpds = ]<br/>] |
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| PPhrases = {{P-phrases|260|261|264|271|280|301+330+331|303+361+353|304+340|305+351+338|310|312|321|363|403+233|405|501}} |
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}} |
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}}<ref>{{Cite web|url=http://www.newenv.com/resources/nfpa_chemicals|title = New Environment Inc. - NFPA Chemicals}}</ref> |
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|Section8={{Chembox Related |
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| OtherCompounds = ]<br/>] |
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}} |
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}} |
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}} |
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'''Chlorosulfuric acid''' (] name: '''sulfurochloridic acid''') is the ] with the formula HSO<sub>3</sub>Cl. It is also known as '''chlorosulfonic acid''', being the ] of ]. It is a distillable, colorless liquid which is ] and a powerful ]. Commercial samples usually are pale brown or straw colored.<ref>{{cite book | last = Cremlyn | first = R. J. | title = Chlorosulfonic Acid | publisher = Royal Society of Chemistry | year = 2002 | isbn = 978-0-85404-498-6}}</ref> |
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] and ]s of chlorosulfuric acid are known as '''chlorosulfates'''. |
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==Structure and properties== |
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Chlorosulfuric acid is a ]. Its structure was debated for many decades until in 1941 Shrinivasa Dharmatti proved by ] that chlorine is directly bonded to sulfur.<ref name=":0">{{Cite book |last1=Kirk |first1=Raymond Eller |url=https://books.google.com/books?id=f8tTAAAAMAAJ&q=Dharmatti |title=Encyclopedia of Chemical Technology |last2=Othmer |first2=Donald Frederick |date=1964 |publisher=Interscience Publishers |language=en}}</ref><ref>{{Cite journal |last=Dharmatti |first=S. S. |date=1941-05-01 |title=Magnetism and Molecular Structure of Sulphur Compounds |url=https://www.ias.ac.in/describe/article/seca/013/05/0359-0370 |journal=Proceedings of the Indian Academy of Sciences - Section A |language=en |volume=13 |issue=5 |pages=359–370 |doi=10.1007/BF03049293 |issn=0370-0089}}</ref> |
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The formula is more descriptively written SO<sub>2</sub>(OH)Cl, but HSO<sub>3</sub>Cl is traditional. It is an intermediate, chemically and conceptually, between ] (SO<sub>2</sub>Cl<sub>2</sub>) and ] (H<sub>2</sub>SO<sub>4</sub>).<ref>{{cite book |last1=Holleman |first1=A. F. |last2=Wiberg |first2=E. | title = Inorganic Chemistry | publisher = Academic Press | location = San Diego | year = 2001 | pages = 549–550 }}</ref> The compound is rarely obtained pure. Upon standing with excess sulfur trioxide, it decomposes to pyrosulfuryl chlorides:<ref name="Ullmann">{{cite encyclopedia |last1=Bergen|first1= Elvira|last2=Maas |first2=J. |last3=Baunack |first3=F. |title = Chlorosulfuric Acid | encyclopedia = Ullmann's Encyclopedia of Industrial Chemistry | year = 2024 | publisher = Wiley-VCH | location = Weinheim | doi = 10.1002/14356007.a07_017.pub2 |isbn=3527306730 }}</ref> |
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:2 ClSO<sub>3</sub>H + SO<sub>3</sub> → H<sub>2</sub>SO<sub>4</sub> + S<sub>2</sub>O<sub>5</sub>Cl<sub>2</sub> |
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==Synthesis== |
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The industrial synthesis entails the reaction of ] with a ] of ] in ]:<ref name=Ullmann/> |
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:HCl + SO<sub>3</sub> → ClSO<sub>3</sub>H |
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It can also be prepared by the method originally used by acid's discoverer ] in 1854,<ref name=":0" /> namely chlorination of sulfuric acid, written here for pedagogical purposes as HSO<sub>3</sub>(OH) vs. the usual format H<sub>2</sub>SO<sub>4</sub>: |
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:] + HSO<sub>3</sub>(OH) → HSO<sub>3</sub>Cl + POCl<sub>3</sub> + HCl |
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The latter method is more suited for laboratory-scale operations. |
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Williamson's discovery disproved then-popular hypothesis that sulfuric acid is a compound of water (which was incorrectly assumed to have formula of HO) and ].<ref>{{cite web | url=https://publishing.cdlib.org/ucpressebooks/view?docId=ft5g500723&chunk.id=d0e3659&toc.depth=100&toc.id=d0e3589&brand=ucpress | title=The Quiet Revolution }}</ref> |
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==Applications== |
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ClSO<sub>2</sub>OH is used to prepare ], which are useful as ]s and as chemical intermediates:<ref name="Ullmann"/> |
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:ROH + ClSO<sub>3</sub>H → ROSO<sub>3</sub>H + HCl |
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One historical synthesis of ] begins with the reaction of ] with ClSO<sub>2</sub>OH to give the ''ortho''- and ] derivatives: |
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:CH<sub>3</sub>C<sub>6</sub>H<sub>5</sub> + 2 ClSO<sub>2</sub>OH → CH<sub>3</sub>C<sub>6</sub>H<sub>4</sub>SO<sub>2</sub>Cl + H<sub>2</sub>SO<sub>4</sub> + HCl |
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Oxidation of the ''ortho'' isomer gives the ] derivative that then is cyclized with ] and neutralized with base to afford saccharin. |
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Chlorosulfonic acid has been used as an anti-] agent in ] reconnaissance drones,<ref>{{cite book | url = https://patentimages.storage.googleapis.com/6c/7c/d2/62398f0fc22989/US3517505.pdf | title = Method and apparatus for suppressing contrails | publisher = United States Patent and Trademark Office | year = 1970}}</ref> and to produce ]s.<ref>{{cite video | title = The Royal Navy at War | medium = DVD | publisher = ] | location = London | date = 2005}}</ref><ref>{{cite web | url = https://www.bbc.com/news/science-environment-43727547 | title = Nazi legacy found in Norwegian trees | date = 2018-04-11 | publisher = ] | first = Jonathan | last = Amos | access-date = 2018-04-17}}</ref> |
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==Safety== |
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ClSO<sub>3</sub>H reacts violently with water to yield sulfuric acid and hydrogen chloride, which are corrosive: |
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:ClSO<sub>3</sub>H + H<sub>2</sub>O → H<sub>2</sub>SO<sub>4</sub> + HCl |
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==Related halosulfuric acids== |
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*], FSO<sub>2</sub>OH, is a related ] with a diminished tendency to evolve ]. |
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*], BrSO<sub>2</sub>OH, is unstable, decomposing at its melting point of 8 °C to give ], ], and ]. |
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*Iodosulfonic acid is not known to occur. |
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==References== |
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{{Reflist|30em}} |
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{{Authority control}} |
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{{DEFAULTSORT:Chlorosulfuric Acid}} |
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] |
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] |