4,4'-Dichlorodiphenyl sulfone

4,4'-Dichlorodiphenyl sulfone

Names
Systematic 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
ChemSpider	6373
Jmol interactive 3D	Image Image
PubChem	6625
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	External MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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 or Udel.^[2]

Synthesis

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]

Uses

DCDPS is the starting material in the polymerization of compounds such as Udel, PES and Radel R. The polymerization occurs through a nucleophilic substitution reaction of DCDPS with difunctional nucleophiles. With bisphenol A in dimethyl sulfoxide, DCDPS forms a material called Udel. This and related condensations adhere to the following stoichiometry:^[2]

(ClC₆H₄)₂SO₂ + HO-X-OH → 1/n [(O-X-OC₆H₄)₂SO₂]_n + 2 HCl

Udel is a high performance amorphous sulfone polymer that can molded into a variety of different shapes. It is both rigid and temperature resistant, and has applications in everything from plumbing pipes, to printer cartridges, to automobile fuses. DCDPS also reacts with bisphenol S to form PES. Like Udel, PES is a rigid and thermally resistant material with numerous applications.

The general polymerization reaction:

Some of the products include:

References

1. Sime, J. G; S. C. Abrahams (1960). "The crystal and molecular structure of 4, 4'-dichlorodiphenyl sulphone". 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 (2002). "Polymers, High‐Temperature". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a21_449.pub3. ISBN 3527306730.
3. Kovacic, Peter; Neal O. Brace (1954). "Chlorination of Aromatic Compounds with Metal Chlorides". Journal of the American Chemical Society 76 (21): 5491–5494. doi:10.1021/ja01650a069.

• 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," Solvay Advanced Polymers LCC, pp 7–10, Alpharetta, GA.

Further Reading

Radel PPSU, Veradel PESU and Acudel modified PPSU Design Guide by Solvay