Diphenyl sulfone

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Diphenyl sulfone
Diphenyl sulfone.svg
Names
Preferred IUPAC name
1,1′-Sulfonyldibenzene
Other names
Diphenyl sulphone
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.004.413 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
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
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).

Diphenyl sulfone is an organosulfur compound with the formula (C6H5)2S2. It is a white solid that is soluble in organic solvents. It is a simple example of a molecule with a sulfone functional group.

Contents

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

  1. ↑ Parker, David; Bussink, Jan; Van De Grampel, Hendrik T.; Wheatley, Gary W.; Dorf, Ernst-Ulrich; Ostlinning, Edgar; Reinking, Klaus; Schubert, Frank; Jünger, Oliver; Wagener, Reinhard (2012). "Polymers, High-Temperature". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a21_449.pub4. ISBN   978-3-527-30673-2.
  2. ↑ Otto Lindner, Lars Rodefeld "Benzenesulfonic Acids and Their Derivatives" in Ullmann's Encyclopedia of Industrial Chemistry 2005, Wiley-VCH, Weinheim. doi : 10.1002/14356007.a03_507
  3. ↑ Roger Adams, C. S. Marvel, H. T. Clarke, G. S. Babcock, and T. F. Murray (1921). "Benzenesulfonyl chloride". Organic Syntheses . 1: 21{{cite journal}}: CS1 maint: multiple names: authors list (link); Collected Volumes, vol. 1, p. 84.
  4. ↑ Sato, Kazuhiko; Hyodo, Mamoru; Aoki, Masao; Zheng, Xiao-Qi; Noyori, Ryoji (2001). "Oxidation of sulfides to sulfoxides and sulfones with 30% hydrogen peroxide under organic solvent- and halogen-free conditions". Tetrahedron. 57 (13): 2469–2476. doi:10.1016/s0040-4020(01)00068-0.
  5. ↑ Chopra, Anu; Dorton, Donna C.; Ogle, Craig A. (1997). "Directed Ortho Dilithiation of Diaryl Compounds: Facile Synthesis of Tricyclic Compounds Based on Heterocycles Fused to Two Benzene Rings". Main Group Metal Chemistry. 20 (12): 783–786. doi:10.1515/mgmc.1997.20.12.783.


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