Sulfuryl chloride 2682431 225576323 2008-07-14T11:34:41Z Puppy8800 5404759 iw {{Chembox new | Name = Sulfuryl chloride | ImageFile = Sulfuryl-chloride-2D-dimensions.png <!-- | ImageSize = 150px --> | ImageName = Sulfuryl chloride | ImageFile1 = Sulfuryl-chloride-3D-vdW.png <!-- | ImageSize1 = 150px --> | ImageName1 = Sulfuryl chloride | IUPACName = Sulfuryl chloride | OtherNames = Sulfonyl Chloride<br />Sulfuric chloride<br /> | Section1 = {{Chembox Identifiers | CASNo = 7791-25-5 }} | Section2 = {{Chembox Properties | Formula = SO<sub>2</sub>Cl<sub>2</sub> | MolarMass = 134.9648 g/mol | Density = 1.665 g ml<sup>-1</sup> at 20 °C | Appearance = Colorless liquid with<br />a pungent odor.<br />yellows upon standing. | Solubility = hydrolyzes | MeltingPt = -54.1 °C | BoilingPt = 69.1 °C }} | Section8 = {{Chembox Related | OtherCpds = [[Thionyl chloride]] (SOCl<sub>2</sub>)<br />[[Chlorosulfonic acid]]<br />[[Sulfuric acid]]<br />[[Sulfuryl fluoride]]}} }} '''Sulfuryl chloride''' is SO<sub>2</sub>Cl<sub>2</sub>, a compound composed of [[sulfur]], [[oxygen]], and [[chlorine]]. At room temperature, it is a colorless liquid with a pungent odor. Sulfuryl chloride is not found in nature, as can be inferred from its speedy hydrolysis Sulfuryl chloride is commonly confused with [[thionyl chloride]], SOCl<sub>2</sub>. The properties of these two sulfur oxychlorides are quite different: sulfuryl chloride is a source of [[chlorine]] whereas thionyl chloride is a source of [[chloride]] ions. ==Properties== Sulfuryl chloride reacts violently with water, releasing [[hydrogen chloride]] gas: :2 [[Water (molecule)|H<sub>2</sub>O]] + SO<sub>2</sub>Cl<sub>2</sub> → 2 [[Hydrochloric acid|HCl]] + [[Sulfuric acid|H<sub>2</sub>SO<sub>4</sub>]] SO<sub>2</sub>Cl<sub>2</sub> will also [[Decomposition|decompose]] when heated to or above 100 °C, about 40 ° above its boiling point. Upon standing, SO<sub>2</sub>Cl<sub>2</sub> decomposes to [[sulfur dioxide]] and [[chlorine]], which gives the older samples a slightly yellowish color. ==Structure== Sulfur is tetrahedral in SO<sub>2</sub>Cl<sub>2</sub>, being bound to two oxygen atoms via double bonds and to two chlorine atoms via single bonds. The [[Oxidation number|oxidation state]] of the sulfur atom is +6, as in H<sub>2</sub>SO<sub>4</sub>. ==Synthesis of sulfuryl chloride== SO<sub>2</sub>Cl<sub>2</sub> is prepared by the reaction of [[sulfur dioxide]] and [[chlorine]] in the presence of a [[catalyst]], such as [[activated carbon]]. :[[Sulfur dioxide|SO<sub>2</sub>]] + [[Chlorine|Cl<sub>2</sub>]] → SO<sub>2</sub>Cl<sub>2</sub> The crude product can be purified by [[fractional distillation]]. It is uncommon to prepare SO<sub>2</sub>Cl<sub>2</sub> in the laboratory because it is supplied by many chemical companies, including FisherChemicals, AcrosOrganics, SFChem, Sigma-Aldrich. ==Uses== Sulfuryl chloride is often used as source of Cl<sub>2</sub>. Because it is a pourable liquid, it is considered more convenient than Cl<sub>2</sub> to measure, store, and dispense. SO<sub>2</sub>Cl<sub>2</sub> is widely used as a [[reagent]] in the conversion of C-H --> C-Cl adjacent to activating substituents such as carbonyls and sulfoxides. It also chlorinates as [[alkane]]s, [[alkene]]s, [[alkyne]]s, [[Aromatic ring|aromatics]], and [[epoxide]]s. Such reactions occur under [[free radical]] conditions using an initiator such as [[AIBN]]. SO<sub>2</sub>Cl<sub>2</sub> can also convert [[alcohol]]s to [[alkyl chloride]]s. In industry, sulfuryl chloride is most used in producing pesticides. SO<sub>2</sub>Cl<sub>2</sub> can also be used to treat wool to prevent shrinking. ==Precautions== SO<sub>2</sub>Cl<sub>2</sub> is toxic, corrosive, and acts as a [[Lachrymatory agent|lachrymator]]. As described above, it can form explosive mixtures with water, as well as donor solvents such as [[Dimethyl sulfoxide|DMSO]] and [[Dimethylformamide|DMF]]. ==References== http://chemfinder.cambridgesoft.com<br /> http://www.chem.unep.ch/irptc/sids/OECDSIDS/7791255.pdf<br /> http://www.mrw.interscience.wiley.com/eros/articles/rs140/frame.html ==Further reading== Lautens, M.; Bouchain, G. "[4+3] Cycloaddition in Water. endo,endo-Dimethyl-8-Oxabicyclo[8-Oxabicyclo[3.2.1]oct-6-en-3-one" Organic Syntheses, ; Vol. 79, p.251 (2002) (Coll. Vol. 10, p.336 (2004)). α-Chlorination of 3-pentanone. [[Category:Chlorides]] [[Category:Sulfuryl compounds]] [[Category:Acyl chlorides]] [[de:Sulfurylchlorid]] [[it:Cloruro di solforile]] [[ja:塩化スルフリル]] [[pl:Chlorek sulfurylu]] [[ru:Хлористый сульфурил]] [[zh:硫酰氯]]