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Sulfuryl chloride

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Title: Sulfuryl chloride  
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Subject: Chlorosulfuric acid, Sulfuryl, Cyanogen halide, Sulfuryl compounds, Hyposulfite
Collection: Oxohalides, Sulfuryl Compounds
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Sulfuryl chloride

Sulfuryl chloride
Structure and dimensions of sulfuryl chloride
Ball-and-stick model of sulfuryl chloride
Names
IUPAC name
Sulfuryl chloride
Other names
Sulfonyl chloride
Sulfuric chloride
Sulfur dichloride dioxide
Identifiers
 Y
ChEBI  Y
ChemSpider  Y
EC number 232-245-6
Jmol-3D images Image
PubChem
Properties
SO2Cl2
Molar mass 134.9698 g mol−1
Appearance Colorless liquid with a pungent odor. Yellows upon standing.
Density 1.67 g cm−3 (20 °C)
Melting point −54.1 °C (−65.4 °F; 219.1 K)
Boiling point 69.4 °C (156.9 °F; 342.5 K)
hydrolyzes
Solubility miscible with benzene, toluene, chloroform, CCl4, glacial acetic acid
1.4437 (20 °C) [1]
Hazards
Corrosive (C)
R-phrases R14, R34, R37
S-phrases (S1/2), S26, S30, S45
NFPA 704
0
3
2
W
Flash point Not flammable
Related compounds
Related sulfuryl halides
Sulfuryl fluoride
Related compounds
Thionyl chloride
Chlorosulfonic acid
Sulfuric acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 Y  (: Y/N?)

Sulfuryl chloride is an inorganic compound with the formula SO2Cl2. 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 rapid 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. An alternative IUPAC name is sulfuroyl dichloride.

Contents

  • Structure 1
  • Synthesis 2
  • Reactions 3
  • Uses 4
  • Precautions 5
  • References 6
  • Further reading 7

Structure

Sulfur is tetrahedral in SO2Cl2, being bound to two oxygen atoms via polarized double bonds (which do not utilize d-orbitals[2]) and to two chlorine atoms via polarized single bonds. The oxidation state of the sulfur atom is +6, as in H2SO4.

Synthesis

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 commercially available. Sulfuryl chloride can also be considered a derivative of sulfuric acid.[3]

Sulfuryl chloride was first prepared in 1838 by the French chemist Henri Victor Regnault.[4]

Reactions

Sulfuryl chloride reacts with water, releasing hydrogen chloride gas and sulfuric acid:

2 H2O + SO2Cl2 → 2 HCl + H2SO4

SO2Cl2 will also decompose when heated to or above 100 °C, about 30 °C above its boiling point.

Upon standing, SO2Cl2 decomposes to sulfur dioxide and chlorine, which gives the older samples a slightly yellowish color.

Uses

Sulfuryl chloride is often used as a 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 alkanes, alkenes, alkynes, aromatics, ethers (such as tetrahydrofuran) and epoxides. Such reactions occur under free radical conditions using an initiator such as AIBN. It can also be used to convert thiols or disulfides into their corresponding sulfenyl chlorides. 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. It can form fuming mixtures with water, as well as donor solvents such as DMSO and DMF.

References

  1. ^ Patnaik, P. (2002). Handbook of Inorganic Chemicals. McGraw-Hill.  
  2. ^ Cunningham, T. P.; Cooper, D. L.; Gerratt, J.; Karadakov, P. B.; Raimondi, M. (1997). "Chemical bonding in oxofluorides of hypercoordinatesulfur". Journal of the Chemical Society, Faraday Transactions 93 (13): 2247–2254.  
  3. ^ Hogan, C. M. (2011). "Sulfur". In Jorgensen, A.; Cleveland, C. J. Encyclopedia of Earth. Washington DC: National Council for Science and the Environment. 
  4. ^ See:
    • Regnault, Victor (1838) "Sur l'acide chlorosulfurique et la sulfamide" (On sulfuryl chloride and sulfamide), Annales de chimie et de physique, series 2, 69 : 170 -184.
    • Reprinted in German as: V. Regnault (1839) "Ueber die Chlorschwefelsäure und das Sulfamid," Journal für Praktische Chemie, 18 : 93–104.
  • "Sulfuryl chloride CAS N°: 7791-25-5" (pdf). OECD SIDS. UNEP Publications. 2004. 
  • Maynard, G. D. (2001). "Sulfuryl Chloride". Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons.  

Further reading

  • Lautens, M.; Bouchain, G. (2002). "[4+3] Cycloaddition in Water. Synthesis of 2,4-endo,endo-Dimethyl-8-Oxabicyclo[3.2.1]oct-6-en-3-one".  
  • McKee, R. H.; Salls, C. M. (1924). "Sulfuryl Chloride".  
  • Moussa, V. N. (2012). "Sulfuryl Chloride: A Versatile Alternative to Chlorine".  
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