- Sulfuryl chloride
Chembox new
Name = Sulfuryl chloride
ImageFile = Sulfuryl-chloride-2D-dimensions.png
ImageName = Sulfuryl chloride
ImageFile1 = Sulfuryl-chloride-3D-vdW.png
ImageName1 = Sulfuryl chloride
IUPACName = Sulfuryl chloride
OtherNames = Sulfonyl Chloride
Sulfuric chloride
Section1 = Chembox Identifiers
CASNo = 7791-25-5
Section2 = Chembox Properties
Formula = SO2Cl2
MolarMass = 134.9648 g/mol
Density = 1.665 g ml-1 at 20 °C
Appearance = Colorless liquid with
a pungent odor.
yellows upon standing.
Solubility = hydrolyzes
MeltingPt = -54.1 °C
BoilingPt = 69.1 °C
Section8 = Chembox Related
OtherCpds =Thionyl chloride (SOCl2)Chlorosulfonic acid Sulfuric acid Sulfuryl fluoride Sulfuryl chloride is SO2Cl2, a compound composed of
sulfur ,oxygen , andchlorine . 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 hydrolysisSulfuryl chloride is commonly confused with
thionyl chloride , SOCl2. The properties of these two sulfur oxychlorides are quite different: sulfuryl chloride is a source ofchlorine whereas thionyl chloride is a source ofchloride ions.Properties
Sulfuryl chloride reacts violently with water, releasing
hydrogen chloride gas::2 H2O + SO2Cl2 → 2 HCl + H2SO4
SO2Cl2 will also decompose when heated to or above 100 °C, about 40 ° above its boiling point.
Upon standing, SO2Cl2 decomposes to
sulfur dioxide andchlorine , which gives the older samples a slightly yellowish color.tructure
Sulfur is tetrahedral in SO2Cl2, being bound to two oxygen atoms via double bonds and to two chlorine atoms via single bonds. The oxidation state of the sulfur atom is +6, as in H2SO4.
ynthesis of sulfuryl chloride
SO2Cl2 is prepared by the reaction of
sulfur dioxide andchlorine in the presence of acatalyst , such asactivated carbon .:SO2 + Cl2 → SO2Cl2The crude product can be purified byfractional distillation . It is uncommon to prepare SO2Cl2 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 Cl2. Because it is a pourable liquid, it is considered more convenient than Cl2 to measure, store, and dispense. SO2Cl2 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 asalkane s,alkene s,alkyne s, aromatics, andepoxide s. Such reactions occur underfree radical conditions using an initiator such asAIBN . SO2Cl2 can also convertalcohol s toalkyl chloride s. In industry, sulfuryl chloride is most used in producing pesticides.SO2Cl2 can also be used to treat wool to prevent shrinking.
Precautions
SO2Cl2 is toxic, corrosive, and acts as a lachrymator. As described above, it can form explosive mixtures with water, as well as donor solvents such as DMSO and DMF.
References
http://chemfinder.cambridgesoft.com
http://www.chem.unep.ch/irptc/sids/OECDSIDS/7791255.pdf
http://www.mrw.interscience.wiley.com/eros/articles/rs140/frame.htmlFurther 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.
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