Sulfolane

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Sulfolane
Names
IUPAC name
6-Thiolane-1,1-dione
Other names
Tetrahydrothiophene 1,1-dioxide
Tetramethylene sulfone
Properties
C4H8O2S
Molar mass 120.17 g/mol
Appearance Colorless solid
Odor Odorless (pure)
Density 1.261 g/cm3 (25 °C)
Melting point 27.5 °C (81.5 °F; 300.6 K)
Boiling point 285 °C (545 °F; 558 K)
Miscible
Solubility Miscible with acetone, benzene, ethanol, toluene
Vapor pressure 0.0062 mmHg at 27.6 °C
Hazards
Safety data sheet Sigma-Aldrich
Flash point 165 °C (329 °F; 438 K)
Lethal dose or concentration (LD, LC):
1,900 mg/kg (mouse, oral)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Sulfolane or tetramethylene sulfone, is an organosulfur compound, formally a cyclic sulfone, with the formula (CH2)4SO2.

Properties

Chemical

Sulfolane resists oxidation by many oxidizing agents.

Physical

Sulfolane is a colorless solid at standard conditions, miscible with water.

Sulfolane is one of the most efficient industrial solvents for separating aromatics from hydrocarbon mixtures.

Availability

Sulfolane is sold by chemical suppliers.

Preparation

Sulfolane is prepared by reacting butadiene with sulfur dioxide via a cheletropic reaction to give sulfolene, which is hydrogenated using Raney nickel as a catalyst to give sulfolane. Purification is done via separation and vacuum distillation.

Oxidizing tetrahydrothiophene with hydrogen peroxide at high temperatures yields sulfolane.

Projects

  • Extraction of aromatic hydrocarbons from hydrocarbon mixtures
  • Vapor suppressant for hydrofluoric acid

Handling

Safety

Sulfolane has low toxicity and it's difficult to ignite.

Storage

In closed bottles.

Disposal

Should be burned in a special incinerator, with SOx scrubbers.

References

Relevant Sciencemadness threads