Sulfuryl chloride

Sulfuryl chloride
Names
IUPAC name
Sulfuryl chloride
Other names
Sulfonyl chloride
Sulfuric chloride
Sulfur dichloride dioxide
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.029.314
EC Number 232-245-6
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R-phrases (outdated) R14, R34, R37
S-phrases (outdated) (S1/2), S26, S30, S45
NFPA 704
Flammability code 0: Will not burn. E.g., waterHealth code 3: Short exposure could cause serious temporary or residual injury. E.g., chlorine gasReactivity code 2: Undergoes violent chemical change at elevated temperatures and pressures, reacts violently with water, or may form explosive mixtures with water. E.g., phosphorusSpecial hazard W: Reacts with water in an unusual or dangerous manner. E.g., cesium, sodiumNFPA 704 four-colored diamond
0
3
2
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).
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Infobox references

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.

Structure

Sulfur is tetrahedral in SO2Cl2 and the oxidation state of the sulfur atom is +6, as in sulfuric acid.

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.[2]

Sulfuryl chloride was first prepared in 1838 by the French chemist Henri Victor Regnault.[3]

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 to 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, though sulfinyl chlorides result from thiols in some cases.[4] 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 dimethyl sulfoxide and dimethylformamide.

References

  1. ↑ Patnaik, P. (2002). Handbook of Inorganic Chemicals. McGraw-Hill. ISBN 0-07-049439-8.
  2. ↑ Hogan, C. M. (2011). "Sulfur". In Jorgensen, A.; Cleveland, C. J. Encyclopedia of Earth. Washington, DC: National Council for Science and the Environment.
  3. ↑ Regnault, Victor (1838). "Sur l'acide chlorosulfurique et la sulfamide" [On sulfuryl chloride and sulfamide]. Annales de chimie et de physique, séries 2 (in French). 69: 170–184.
    • Reprinted as: Regnault, Victor (1839). "Ueber die Chlorschwefelsäure und das Sulfamid" [On sulfuryl chloride and sulfamide]. Journal für Praktische Chemie (in German). 18: 93–104. doi:10.1002/prac.18390180104.
  4. ↑ Page, P. C. B.; Wilkes, R. D.; Reynolds, D. (1995). "Alkyl Chalcogenides: Sulfur-based Functional Groups". In Ley, Steven V. Synthesis: Carbon with One Heteroatom Attached by a Single Bond. Comprehensive Organic Functional Group Transformations. Elsevier. pp. 113–276. ISBN 9780080423234.

  • "Sulfuryl chloride CAS No.: 7791-25-5" (PDF). OECD SIDS. UNEP Publications. 2004. Archived from the original (pdf) on 2007-02-28.
  • Maynard, G. D. (2001). "Sulfuryl Chloride". Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons. doi:10.1002/047084289X.rs140.

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". Organic Syntheses. 79: 251. ; Collective Volume, 10, p. 336
  • McKee, R. H.; Salls, C. M. (1924). "Sulfuryl Chloride". Industrial and Engineering Chemistry. 16 (4): 351–353. doi:10.1021/ie50172a008.
  • Moussa, V. N. (2012). "Sulfuryl Chloride: A Versatile Alternative to Chlorine". Australian Journal of Chemistry. 65 (1): 95–96. doi:10.1071/CH11367.
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