Sulfolane

Names

IUPAC name

Tetrahydrothiophene 1,1-dioxide

Other names

sulfolane
tetramethylene sulfone

Identifiers

CAS Number

126-33-0^N

3D model (Jmol)

CHEBI:74794^N

29080^Y

Y5L06AH4G5^Y

InChI=1S/C4H8O2S/c5-7(6)3-1-2-4-7/h1-4H2^Y

Key: HXJUTPCZVOIRIF-UHFFFAOYSA-N^Y
InChI=1/C4H8O2S/c5-7(6)3-1-2-4-7/h1-4H2

Key: HXJUTPCZVOIRIF-UHFFFAOYAA

SMILES

C1CCS(=O)(=O)C1

Properties

Chemical formula

C₄H₈O₂S

Molar mass

120.17 g/mol

Appearance

clear colorless liquid

Density

1.261 g/cm³, liquid

Melting point

27.5 °C (81.5 °F; 300.6 K)

Boiling point

285 °C (545 °F; 558 K)

Solubility in water

miscible

Viscosity

0.01007 Pa·s at 25 °C

Structure

Dipole moment

4.35 D

Hazards

S23, S24, S25

165 °C (329 °F; 438 K)

Autoignition
temperature

528 °C (982 °F; 801 K)

Related compounds

Methylsulfonylmethane

Tetrahydrothiophene
Sulfolene

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

Tetrahydrothiophene
Sulfolene

Sulfolane (also tetramethylene sulfone, systematic name: 2,3,4,5-tetrahydrothiophene-1,1-dioxide) is an organosulfur compound, formally a cyclic sulfone, with the formula (CH₂)₄SO₂. It is a colorless liquid commonly used in the chemical industry as a solvent for extractive distillation and chemical reactions. Sulfolane was originally developed by the Shell Oil Company in the 1960s as a solvent to purify butadiene. Sulfolane is a polar aprotic solvent, and it is readily soluble in water.

Sulfolane is classified as a sulfone, a group of organosulfur compounds containing a sulfonyl functional group. The sulfone group is a sulfur atom doubly bonded to two oxygen atoms and singly bonded to two carbon centers. The sulfur-oxygen double bond is polar, conferring good solubility in water, while the four carbon ring provides non-polar stability. These properties allow it to be miscible in both water and hydrocarbons, resulting in its widespread use as a solvent for purifying hydrocarbon mixtures.

The original method developed by the Shell Oil Company was to first allow butadiene to react with sulfur dioxide via a cheletropic reaction to give sulfolene. This was then hydrogenated using Raney nickel as a catalyst to give sulfolane.

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