Sulfuryl chloride
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{{Chembox new
| Name = Sulfuryl chloride
| ImageFile = Sulfuryl-chloride-2D-dimensions.png
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| ImageName = Sulfuryl chloride
| ImageFile1 = Sulfuryl-chloride-3D-vdW.png
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| 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]]