|Jmol-3D images||Image 1|
|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, 219.1 K|
|Boiling point||69.4 °C, 342.6 K|
|Solubility in water||hydrolyzes|
|Solubility||miscible with benzene, toluene, chloroform, CCl4, glacial acetic acid|
|Refractive index (nD)||1.4437 (20 °C) |
|EU classification||Corrosive (C)|
|R-phrases||R14, R34, R37|
|S-phrases||(S1/2), S26, S30, S45|
|Flash point||Not flammable|
|Related sulfuryl halides||Sulfuryl fluoride|
|Related compounds||Thionyl chloride
|Except where noted otherwise, 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.
Sulfur is tetrahedral in SO2Cl2, being bound to two oxygen atoms via bonds intermediate of a dative bond and a polarized double bond (which does not utilize d-orbitals) and to two chlorine atoms via polarized single bonds. The oxidation state of the sulfur atom is +6, as in H2SO4.
- 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 → C-Cl adjacent to activating substituents such as carbonyls and sulfoxides. It also chlorinates alkanes, alkenes, alkynes, aromatics, and epoxides. Such reactions occur under free radical conditions using an initiator such as AIBN. It can also be used to convert 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.
- Patnaik, P. (2002). Handbook of Inorganic Chemicals. McGraw-Hill. ISBN 0-07-049439-8.
- 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. doi:10.1039/A700708F.
- 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 choride 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. doi:10.1002/047084289X.rs140.
- 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", Org. Synth. 79: 251; Coll. Vol. 10: 336
- McKee, R. H.; Salls, C. M. (1924). "Sulfuryl Chloride". Industrial and Engineering Chemistry 16 (4): 351–353. doi:10.1021/ie50172a008.