Diphenyl sulfone

Chemical compound From Wikipedia, the free encyclopedia

Diphenyl sulfone is an organosulfur compound with the formula (C6H5)2SO2. It is a white solid that is soluble in organic solvents. It is a simple example of a molecule with a sulfone functional group.

Quick facts Names, Identifiers ...
Diphenyl sulfone
Names
Preferred IUPAC name
1,1′-Sulfonyldibenzene
Other names
Diphenyl sulphone
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.004.413 Edit this at Wikidata
UNII
  • InChI=1S/C12H10O2S/c13-15(14,11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10H
    Key: KZTYYGOKRVBIMI-UHFFFAOYSA-N
  • InChI=1/C12H10O2S/c13-15(14,11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10H
    Key: KZTYYGOKRVBIMI-UHFFFAOYAU
  • O=S(=O)(c1ccccc1)c2ccccc2
Properties
C12H10O2S
Molar mass 218.27 g·mol−1
Appearance White solid
Melting point 123 °C (253 °F; 396 K)
Boiling point 379 °C (714 °F; 652 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Uses

It is used as a high temperature solvent. Such high temperature solvents are useful for processing highly rigid polymers, such as PEEK, which only dissolve in very hot solvents.[1]

Preparation and reactions

Diphenyl sulfone is produced by the sulfonation of benzene with sulfuric acid and oleum. For typical processes, benzenesulfonic acid is an intermediate.[2] It is also produced from benzenesulfonyl chloride and benzene.[3]

Oxidation of diphenylsulfide with 30% hydrogen peroxide efficiently gives the sulfone in the presence of a tungstate catalyst.[4]

(C6H5)2S + 2 H2O2 → (C6H5)2SO2 + 2 H2O

Diphenyl sulfone reacts with butyllithium to give the dilithio derivative:

(C6H5)2SO2 + 2 C4H9Li → (C6H4Li)2SO2 + 2 C4H10

The dilithio derivative can be quenched with a variety of electrophiles[5]

References

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