Sulfuryl chloride


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, 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, SOCl2. 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 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 and chlorine, 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 and chlorine in the presence of a catalyst, such as activated carbon.:SO2 + Cl2 → SO2Cl2The crude product can be purified by fractional 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 as alkanes, alkenes, alkynes, aromatics, and epoxides. Such reactions occur under free radical conditions using an initiator such as AIBN. SO2Cl2 can also convert alcohols to alkyl chlorides. 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.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.


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