Sulfur dichloride dioxide
3D model (JSmol)
|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)|
|Solubility||miscible with benzene, toluene, chloroform, CCl4, glacial acetic acid|
Refractive index (nD)
|1.4437 (20 °C)|
|R-phrases (outdated)||R14, R34, R37|
|S-phrases (outdated)||(S1/2), S26, S30, S45|
|Flash point||Not flammable|
Related sulfuryl halides
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
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.
- 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 H2O + SO2Cl2 → 2 HCl + H2SO4
SO2Cl2 will also decompose when heated to or above 100 °C, about 30 °C above its boiling point.
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. 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.
- Patnaik, P. (2002). Handbook of Inorganic Chemicals. McGraw-Hill. ISBN 0-07-049439-8.[page needed]
- Hogan, C. M. (2011). "Sulfur". In Jorgensen, A.; Cleveland, C. J. Encyclopedia of Earth. Washington, DC: National Council for Science and the Environment.
- 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.
- 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.
- 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.