Sulfuryl chloride

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Sulfuryl chloride
Names
IUPAC name
Sulfuryl chloride
Other names
Sulfonyl chloride
Sulfur dichloride dioxide
Sulfuric chloride
Sulfuroyl dichloride
Properties
SO2Cl2
Molar mass 134.9698 g/mol
Appearance Colorless liquid with a strong pungent odor
Yellowish upon standing
Odor Pungent, suffocating
Density 1.67 g/cm3 (at 20 °C)
Melting point −54.1 °C (−65.4 °F; 219.1 K)
Boiling point 69.4 °C (156.9 °F; 342.5 K)
Reacts
Solubility Reacts with alcohols, amines, esters
Miscible with glacial acetic acid, benzene, carbon tetrachloride, chloroform, dichloromethane, toluene
Soluble in HCN, liq. SO2, SnCl4
Immiscible with conc. sulfuric acid
Vapor pressure 106.5 mmHg (at 20 °C)
Thermochemistry
393 kJ/mol
Hazards
Safety data sheet ScienceLab
Flash point Non-flammable
Related compounds
Related compounds
Thionyl chloride
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Sulfuryl chloride is a water sensitive inorganic compound with the formula SO2Cl2. Sulfuryl chloride is sometimes confused with thionyl chloride (SOCl2), however the properties of the two chemicals are very different, as sulfuryl chloride is a source of chlorine, while thionyl chloride is a source of chloride ions.

Properties

Chemical

Sulfuryl chloride reacts exothermically with water to form hydrogen chloride and sulfuric acid:

2 H2O + SO2Cl2 → 2 HCl + H2SO4

It will chlorinate various organic compounds, such as alkanes, alkenes, alkynes, aromatics, ethers. It will also chlorinate the metal center from organometallic compounds, when it is in a lower oxidation state.

Physical

Sulfuryl chloride is a colorless to yellowish liquid, with a strong poignant smell reminiscent of burned matches. It readily hydrolyzes in water.

Availability

Sulfuryl chloride is sold by various chemical suppliers, but it is extremely difficult for the amateur chemist to acquire it.

Preparation

Sulfuryl chloride can be made by reacting sulfur dioxide and chlorine. The reaction is generally done without a solvent. Activated carbon is used as a catalyst, though UV light can speed up the reaction.

It can also be prepared by reacting disulfur dichloride with sulfur dioxide, at 170°C. Elemental sulfur is produced as a byproduct.

Projects

  • Make chlorobenzene
  • Make alkyl chlorides

Handling

Safety

Sulfuryl is extremely corrosive and toxic. It hydrolyzes in water.

Storage

Sulfuryl chloride should be stored in glass bottles, preferably amber glass, away from any moisture, best in a corrosive chemicals cabinet.

Disposal

Sulfuryl chloride can be neutralized with an alkaline solution. The reaction will release plenty of corrosive fumes, so it's best to do this outside.

References

Relevant Sciencemadness threads