4,4'-Dichlorodiphenyl sulfone

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 or Udel.^[2]

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 Y
3D model (JSmol)	Interactive image Interactive image
ChemSpider	6373 Y
ECHA InfoCard	100.001.135
PubChem CID	6625
UNII	5U49794253 Y
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 Y Key: GPAPPPVRLPGFEQ-UHFFFAOYSA-N Y 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). N verify (what is YN ?) Infobox references

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 activated toward substitution, DCDPS is useful in the production of polysulfones:

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

Further reading

• Graybill, Bruce M. (1967). "Synthesis of aryl sulfones". The Journal of Organic Chemistry. 32 (9): 2931–2933. doi:10.1021/jo01284a075.
• Udel Polysulfone Design Guide (Report). Alpharetta, GA: Solvay Advanced Polymers. pp. 7–10.
• Radel PPSU, Veradel PESU and Acudel modified PPSU Design Guide by Solvay

References

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.
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 978-3527306732.
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.