| Revision as of 19:12, 9 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 469705575 of page Sulfuryl_chloride for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 20:15, 1 January 2025 edit 91.139.213.126 (talk) →Legacy routes |
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{{short description|Chemical compound}} |
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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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| verifiedrevid = 450898795 |
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|verifiedrevid = 470482530 |
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| Name = Sulfuryl chloride |
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| ImageFile = Sulfuryl-chloride-2D-dimensions.png |
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|Name = Sulfuryl chloride |
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|ImageFile = Sulfuryl-chloride-2D-dimensions.png |
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| ImageSize = 160px |
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|ImageSize = 160px |
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| ImageName = Structure and dimensions of sulfuryl chloride |
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|ImageName = Structure and dimensions of sulfuryl chloride |
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| ImageFile1 = Sulfuryl-chloride-3D-vdW.png |
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|ImageFile1 = Sulfuryl-chloride-3D-vdW.png |
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| ImageSize1 = 140px |
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|ImageSize1 = 140px |
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| ImageName1 = Ball-and-stick model of sulfuryl chloride |
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|ImageName1 = Ball-and-stick model of sulfuryl chloride |
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| ImageFile2 = Sulphuryl chloride 25ml.jpg |
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|ImageFile2 = Sulphuryl chloride 25ml.jpg |
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| IUPACName = Sulfuryl chloride |
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|IUPACName = Sulfuryl chloride |
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| OtherNames = Sulfonyl chloride<br />Sulfuric chloride |
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|OtherNames = Sulfonyl chloride<br />Sulfuric chloride<br />Sulfur dichloride dioxide |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 23050 |
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|ChemSpiderID = 23050 |
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| PubChem = 24648 |
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|PubChem = 24648 |
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| InChI = 1/Cl2O2S/c1-5(2,3)4 |
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|InChI = 1/Cl2O2S/c1-5(2,3)4 |
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| InChIKey = YBBRCQOCSYXUOC-UHFFFAOYAD |
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|InChIKey = YBBRCQOCSYXUOC-UHFFFAOYAD |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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|ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 29291 |
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|ChEBI = 29291 |
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|ChEMBL = 3186735 |
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| SMILES = ClS(Cl)(=O)=O |
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|SMILES = ClS(Cl)(=O)=O |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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|StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/Cl2O2S/c1-5(2,3)4 |
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|StdInChI = 1S/Cl2O2S/c1-5(2,3)4 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = YBBRCQOCSYXUOC-UHFFFAOYSA-N |
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|StdInChIKey = YBBRCQOCSYXUOC-UHFFFAOYSA-N |
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| CASNo = 7791-25-5 |
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|CASNo = 7791-25-5 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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|CASNo_Ref = {{cascite|correct|CAS}} |
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| EINECS = 232-245-6 |
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|UNII_Ref = {{fdacite|correct|FDA}} |
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}} |
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|UNII = JD26K0R3J1 |
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| Section2 = {{Chembox Properties |
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|EINECS = 232-245-6 |
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| Formula = SO<sub>2</sub>Cl<sub>2</sub> |
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|RTECS = WT4870000 |
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| MolarMass = 134.965 g mol<sup>−1</sup> |
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|UNNumber = 1834 |
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| Density = 1.667 g cm<sup>−3</sup> (20 °C) |
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|Gmelin = 2256 |
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| Appearance = Colorless liquid with a pungent odor. Yellows upon standing. |
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| Solubility = hydrolyzes |
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| SolubleOther = miscible with ], ], ], ], glacial ] |
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| MeltingPt = −54.1 °C, 219.1 K |
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| BoilingPt = 69.4 °C, 342.6 K |
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| RefractIndex = 1.4437 (20 °C) <ref>Pradyot Patnaik. ''Handbook of Inorganic Chemicals''. McGraw-Hill, 2002, ISBN 0070494398</ref> |
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}} |
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| Section7 = {{Chembox Hazards |
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| ExternalMSDS = |
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| EUClass = Corrosive ('''C''') |
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| EUIndex = 016-016-00-6 |
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| NFPA-H = 3 |
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| NFPA-F = 0 |
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| NFPA-R = 2 |
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| NFPA-O = |
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| RPhrases = {{R14}}, {{R34}}, {{R37}} |
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| SPhrases = {{S1/2}}, {{S26}}, {{S45}} |
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| FlashPt = Non-flammable |
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| PEL = |
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}} |
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| Section8 = {{Chembox Related |
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| OtherFunctn = ] |
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| Function = sulfuryl halides |
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| OtherCpds = ]<br />]<br />] |
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}} |
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}} |
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}} |
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|Section2={{Chembox Properties |
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|Formula = SO<sub>2</sub>Cl<sub>2</sub> |
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|MolarMass = 134.9698 g mol<sup>−1</sup> |
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|Density = 1.67 g cm<sup>−3</sup> (20 °C) |
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|Appearance = Colorless liquid with a pungent odor. Yellows upon standing. |
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|Solubility = hydrolyzes |
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|SolubleOther = miscible with ], ], ], ], glacial ] |
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|MeltingPtC = −54.1 |
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|BoilingPtC = 69.4 |
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|RefractIndex = 1.4437 (20 °C)<ref>{{ cite book | last = Patnaik | first = P. | title = Handbook of Inorganic Chemicals | publisher = McGraw-Hill | year = 2002 | isbn = 978-0-07-049439-8 }}{{page needed|date=September 2017}}</ref> |
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}} |
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|Section3={{Chembox Hazards |
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|GHSPictograms = {{GHS05}}{{GHS07}} |
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|GHSSignalWord = Danger |
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|HPhrases = {{H-phrases|314|335}} |
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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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|NFPA-H = 3 |
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|NFPA-F = 0 |
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|NFPA-R = 2 |
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|NFPA-S = W |
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|FlashPt = Not flammable |
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}} |
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|Section4={{Chembox Related |
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|OtherFunction = ] |
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|OtherFunction_label = sulfuryl halides |
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|OtherCompounds = ]<br />]<br />] |
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}} |
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}} |
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'''Sulfuryl chloride''' is an inorganic compound with the formula SO<sub>2</sub>Cl<sub>2</sub>. At ], it is a colorless liquid with a pungent odor. Sulfuryl chloride is not found in nature, as can be inferred from its rapid ]. |
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Sulfuryl chloride is commonly confused with ], SOCl<sub>2</sub>. The properties of these two sulfur oxychlorides are quite different: sulfuryl chloride is a source of ] whereas thionyl chloride is a source of ] ions. An alternative IUPAC name is '''sulfuryl dichloride'''. |
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Sulfur is tetrahedral in SO<sub>2</sub>Cl<sub>2</sub> and the ] of the sulfur atom is +6, as in ]. |
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==Synthesis== |
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SO<sub>2</sub>Cl<sub>2</sub> is prepared by the reaction of ] and ] in the presence of a ], such as ].<ref name=Brauer>{{cite book|author=F. Fehér|chapter=Sulfuryl Chloride|title=Handbook of Preparative Inorganic Chemistry, 2nd Ed.|editor=G. Brauer|publisher=Academic Press|year=1963|place=NY, NY|volume=1|pages=382–384}}</ref> |
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:SO<sub>2</sub> + Cl<sub>2</sub> → SO<sub>2</sub>Cl<sub>2</sub> |
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The product can be purified by ]. |
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===Legacy routes=== |
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Sulfuryl chloride was first prepared in 1838 by the French chemist ].<ref>{{cite journal|last=Regnault|first=Victor|author-link=Henri Victor Regnault|date=1838|url=https://books.google.com/books?id=oSdCAAAAcAAJ&pg=PA170|title=Sur l'acide chlorosulfurique et la sulfamide|trans-title=On sulfuryl chloride and sulfamide|language=fr|journal=Annales de Chimie et de Physique |series=Série 2|volume=69|pages=170–184}} |
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* Reprinted as: {{cite journal|last=Regnault|first=Victor|author-link=Henri Victor Regnault|date=1839|url=https://books.google.com/books?id=MdEPAAAAQAAJ&pg=PA93|title=Ueber die Chlorschwefelsäure und das Sulfamid|trans-title=On sulfuryl chloride and sulfamide|language=de|journal=Journal für Praktische Chemie|volume=18|pages=93–104|doi=10.1002/prac.18390180104}}</ref> |
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Older routes include oxidation of thionyl chloride: |
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:5 SOCl<sub>2</sub> + HgO → ClSSCl + HgCl<sub>2</sub> + 3 SO<sub>2</sub>Cl<sub>2</sub> |
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:2 SOCl<sub>2</sub> + MnO<sub>2</sub> → SO<sub>2</sub> + MnCl<sub>2</sub> + SO<sub>2</sub>Cl<sub>2</sub> |
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==Reactions== |
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Sulfuryl chloride reacts with ], releasing ] gas and ]: |
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:2 H<sub>2</sub>O + SO<sub>2</sub>Cl<sub>2</sub> → 2 HCl + H<sub>2</sub>SO<sub>4</sub> |
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For sulfuryl chloride, this happens at room temperature, but the related ] does not hydrolyse at temperatures up to 150 °C. |
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SO<sub>2</sub>Cl<sub>2</sub> will also ] when heated to or above 100 °C, about 30 °C above its boiling point. |
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Upon standing, SO<sub>2</sub>Cl<sub>2</sub> decomposes to ] and ], which gives the older samples a slightly yellowish color.<ref name=Brauer/> |
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SO<sub>2</sub>Cl<sub>2</sub> can be used as a source of chlorine in alkane chlorination, initiated by chemicals (usually a peroxide) or light:<ref>{{cite book |title=Basic Principles of Organic Chemistry |vauthors=Roberts JD, Caserio MC |section=Practical Halogenations and Problems of Selectivity |section-url=https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Book%3A_Basic_Principles_of_Organic_Chemistry_(Roberts_and_Caserio)/04%3A_Alkanes/4.06%3A_Practical_Halogenations_and_Problems_of_Selectivity }}</ref> |
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:CH<sub>4</sub> + SO<sub>2</sub>Cl<sub>2</sub> → CH<sub>3</sub>Cl + SO<sub>2</sub> + HCl |
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==Uses== |
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Sulfuryl chloride is used as a source of Cl<sub>2</sub>. Because it is a pourable liquid, it is considered more convenient than Cl<sub>2</sub> to dispense. |
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Sulfuryl chloride is used in the conversion of C−H to C−Cl adjacent to activating substituents such as carbonyls and sulfoxides:<ref>{{cite journal |doi=10.15227/orgsyn.079.0251 |title=[4+3] Cycloaddition in Water. Synthesis of 2,4-endo,endo-Dimethyl-8-oxabicyclo[3.2.1]oct-6-en-3-one |journal=Organic Syntheses |date=2002 |volume=79 |page=251|author=Mark Lautens, Giliane Bouchain }}</ref><ref>{{cite journal |doi=10.15227/orgsyn.040.0054 |title=3-Hydroxyquinoline |journal=Organic Syntheses |date=1960 |volume=40 |page=54|first1=Edward J. |last1=Cragoe, Jr |first2=Charles M.|last2=Robb }}</ref> |
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:{{chem2|RC(O)CH2R' + SO2Cl2 -> RC(O)CHClR' + HCl + SO2}} |
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It also chlorinates ]s, ]s, ]s, ], ethers (such as ]) and ]s. Such reactions occur under ] conditions using an initiator such as ]. It convert ]s or ]s into the corresponding ]s:<ref>{{cite journal |doi=10.15227/orgsyn.068.0008 |title=(Phenylthio)Nitromethane |journal=Organic Syntheses |date=1990 |volume=68 |page=8|first1=Anthony G. M. |last1=Barrett|first2=Dashyant |last2=Dhanak|first3=Gregory G. |last3=Graboski|first4=Sven J.|last4=Taylor }}</ref> |
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:{{chem2|RSH + SO2Cl2 -> RSCl + HCl + SO2}} |
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Occasionally, ]s result from such reactions.<ref>{{cite book|pages = |chapter = Alkyl Chalcogenides: Sulfur-based Functional Groups|chapter-url = https://books.google.com/books?id=BPcxrmIgLKMC&pg=PA173|title = Synthesis: Carbon with One Heteroatom Attached by a Single Bond|editor-first = Steven V.|editor-last = Ley|editor-link = Steven V. Ley|publisher = ]|year = 1995|series = Comprehensive Organic Functional Group Transformations|isbn = 9780080423234|last1 = Page|first1 = P. C. B.|last2 = Wilkes|first2 = R. D.|last3 = Reynolds|first3 = D.|url = https://archive.org/details/comprehensiveorg0000unse/page/113}}</ref> SO<sub>2</sub>Cl<sub>2</sub> can also convert ]s to ]s. In industry, sulfuryl chloride is most used in producing pesticides. ] is prepared by the reaction of ] with sulfuryl chloride. |
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Sulfuryl chloride can also be used to treat wool to prevent shrinking. |
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==Precautions== |
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Sulfuryl chloride is toxic, corrosive, and acts as a ]. It releases hydrogen chloride upon contact with water, as well as donor solvents such as ] and ]. |
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==References== |
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{{Reflist}} |
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{{Refbegin}} |
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* {{cite web | publisher = UNEP Publications | title = Sulfuryl chloride CAS No.: 7791-25-5 | url = http://www.chem.unep.ch/irptc/sids/OECDSIDS/7791255.pdf | work = OECD SIDS | year = 2004 | url-status = dead | archive-url = https://web.archive.org/web/20070228150726/http://www.chem.unep.ch/irptc/sids/OECDSIDS/7791255.pdf | archive-date = 2007-02-28 }} |
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* {{ cite encyclopedia | last = Maynard | first = G. D. | encyclopedia = Encyclopedia of Reagents for Organic Synthesis | publisher = John Wiley & Sons | year = 2001 | doi = 10.1002/047084289X.rs140 | chapter-url = http://onlinelibrary.wiley.com/o/eros/articles/rs140/frame.html | isbn = 978-0471936237 | chapter = Sulfuryl Chloride }} |
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{{Refend}} |
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==Further reading== |
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{{Refbegin}} |
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* {{OrgSynth |journal=Org. Synth. |last1 = Lautens | first1 = M. | last2 = Bouchain | first2 = G. | title = Cycloaddition in Water. Synthesis of 2,4-''endo'',''endo''-Dimethyl-8-Oxabicyclooct-6-en-3-one | year = 2002 | volume = 79 | pages = 251 | doi=10.15227/orgsyn.079.0251}} |
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* {{cite journal | title = Sulfuryl Chloride |last1=McKee |first1=R. H. |last2=Salls |first2=C. M. | journal = ] | year = 1924 | volume = 16 | issue = 4 | pages = 351–353 | doi = 10.1021/ie50172a008 }} |
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* {{cite journal | title = Sulfuryl Chloride: A Versatile Alternative to Chlorine | last = Moussa | first= V. N. | journal = ] | year = 2012 | volume = 65 | issue = 1 | pages = 95–96 | doi = 10.1071/CH11367 }} |
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* {{cite journal | title = The Action of Thionyl and Sulphuryl Chlorides on Mercury and Mercury Oxide | last = North| first= H. B. | journal = ] | year = 1910 | volume = 32 | issue = 2| pages = 184–187 | doi = 10.1021/ja01920a004 | url = https://zenodo.org/record/2166706}} |
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* {{cite journal | title = Some New Reactions with Thionyl Chloride | last1 = North| first1 = H. B. |last2 = Hageman| first2 = A. G. | journal = ] | year = 1913 | volume = 35 | issue = 5| pages = 543–546 | doi = 10.1021/ja02194a004 }} |
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{{Refend}} |
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] |
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] |