4,4'-Dichlorodiphenyl sulfone

4,4′-Dichlorodiphenyl sulfone
Names
	Preferred IUPAC name 1,1′-Sulfonylbis(4-chlorobenzene)
	Other names Bis(4-chlorophenyl) sulfone; Bis(p-chlorophenyl) sulfone; p,p′-Dichlorodiphenyl sulfone; DCDPS;
Identifiers
CAS Number	80-07-9 ;
3D model (JSmol)	Interactive image; Interactive image;
ChemSpider	6373 ;
ECHA InfoCard	100.001.135
PubChem CID	6625;
UNII	5U49794253 ;
CompTox Dashboard (EPA)	DTXSID9024986 ;
	InChI InChI=1S/C12H8Cl2O2S/c13-9-1-5-11(6-2-9)17(15,16)12-7-3-10(14)4-8-12/h1-8H Key: GPAPPPVRLPGFEQ-UHFFFAOYSA-N ; InChI=1/C12H8Cl2O2S/c13-9-1-5-11(6-2-9)17(15,16)12-7-3-10(14)4-8-12/h1-8H Key: GPAPPPVRLPGFEQ-UHFFFAOYAQ;
	SMILES O=S(=O)(c1ccc(Cl)cc1)c2ccc(Cl)cc2; O=S(=O)(c1ccc(Cl)cc1)c2ccc(Cl)cc2;
Properties
Chemical formula	C12H8Cl2O2S
Molar mass	287.15 g·mol−1
Appearance	White solid
Melting point	148 °C (298 °F; 421 K)
Boiling point	397 °C (747 °F; 670 K)
Solubility in water	Insoluble
Hazards
Safety data sheet (SDS)	External MSDS
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

4,4′-Dichlorodiphenyl sulfone (DCDPS) is an organic compound with the formula (ClC₆H₄)₂SO₂. Classified as a sulfone,^[1] this white solid is most commonly used as a precursor to polymers that are rigid and temperature-resistant such as PES and Udel.^[2]

Synthesis and reactions

DCDPS is synthesized via sulfonation of chlorobenzene with sulfuric acid, often in the presence of various additives to optimize the formation of the 4,4′-isomer:

ClC₆H₅ + SO₃ → (ClC₆H₄)₂SO₂ + H₂O

It can also be produced by chlorination of diphenylsulfone.^[3]

With chloride substituents susceptible to substitution, DCDPS is useful in the production of polysulfones. One such polymer, victrex, is prepared by the reaction of DCDPS with 4,4′-sulfonylbisphenol (bisphenol S). Similarly DCDPS reacts with bisphenol-A to give the polymer called Udel. These condensations are represented as follows:

n (ClC₆H₄)₂SO₂ + n NaO−X−ONa → [(O−X−OC₆H₄)₂SO₂]_n + 2n NaCl

References

^ Sime, J. G; Abrahams, S. C. (1960). "The crystal and molecular structure of 4,4′-dichlorodiphenyl sulphone" (PDF). Acta Crystallographica. 13 (1): 1–9. doi:10.1107/S0365110X60000017.
^ Parker, David; Bussink, Jan; Grampel, Hendrik T.; Wheatley, Gary W.; Dorf, Ernst‐Ulrich; Ostlinning, Edgar; Reinking, Klaus; Schubert, Frank; Jünger, Oliver. "Polymers, High‐Temperature". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a21_449.pub3. ISBN 978-3-527-30673-2.
^ Kovacic, Peter; Brace, Neal O. (1954). "Chlorination of Aromatic Compounds with Metal Chlorides". Journal of the American Chemical Society. 76 (21): 5491–5494. doi:10.1021/ja01650a069.

[1] Sime, J. G; Abrahams, S. C. (1960). "The crystal and molecular structure of 4,4′-dichlorodiphenyl sulphone" (PDF). Acta Crystallographica. 13 (1): 1–9. doi:10.1107/S0365110X60000017.

[Ullmann-2] Parker, David; Bussink, Jan; Grampel, Hendrik T.; Wheatley, Gary W.; Dorf, Ernst‐Ulrich; Ostlinning, Edgar; Reinking, Klaus; Schubert, Frank; Jünger, Oliver. "Polymers, High‐Temperature". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a21_449.pub3. ISBN 978-3-527-30673-2.

[3] Kovacic, Peter; Brace, Neal O. (1954). "Chlorination of Aromatic Compounds with Metal Chlorides". Journal of the American Chemical Society. 76 (21): 5491–5494. doi:10.1021/ja01650a069.

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[2]

[3]

Synthesis and reactions

Further reading

References