Diphenyl sulfone

Diphenyl sulfone
Names
	Preferred IUPAC name 1,1′-Sulfonyldibenzene
	Other names Diphenyl sulphone
Identifiers
CAS Number	127-63-9 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:78360;
ChemSpider	29117;
ECHA InfoCard	100.004.413
PubChem CID	31386;
UNII	V25W2CFS3M ;
CompTox Dashboard (EPA)	DTXSID6041892 ;
	InChI 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;
	SMILES O=S(=O)(c1ccccc1)c2ccccc2;
Properties
Chemical formula	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). Infobox references

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.

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

^ 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.
^ 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
^ 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.
^ 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.
^ 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.

[Parker-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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