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Sulfuryl chloride



Sulfuryl chloride
General
Systematic name Sulfuryl chloride
Other names Sulfonyl Chloride
Sulfuric chloride
Molecular formula SO2Cl2
CAS number [7791-25-5]
Molar mass 134.9648 g/mol
Appearance Colorless liquid with
a pungent odor.
yellows upon standing.
Properties
Density, phase 1.667 g/cm3, liquid
Solubility in water hydrolyzes
Solubility
in other solvents
miscible in most
organic solvents
solvent incompatibility DMSO, alcohols
DMF, ethers
Melting point -54.1 °C
Boiling point 69.1 °C
Vapour Pressure 511hPa (20 ° C)
Purification Process Fractional distillation
Main Hazards Lachrymatory agent
Related compounds Thionyl chloride (SOCl2)
Chlorosulfonic acid
Sulfuric acid
Infobox disclaimer and references

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.

Additional recommended knowledge

Contents

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.

Structure

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.

Synthesis 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 → SO2Cl2

The 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.

 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Sulfuryl_chloride". A list of authors is available in Wikipedia.
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