|Jmol-3D images||Image 1
|Molar mass||287.16 g/mol|
|Melting point||143 °C (289 °F; 416 K)|
|Boiling point||250 °C (482 °F; 523 K)|
|Solubility in water||Insoluble|
|Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)|
|(what is: / ?)|
4,4'-Dichlorodiphenyl sulfone, abbreviated as DCDPS, is an organic compound with the formula (ClC6H4)2SO2. Classified as a sulfone, this white solid is most commonly used as a precursor to polymers that are rigid and temperature resistant such as PES or Udel.
- ClC6H5 + SO3 → (ClC6H4)2SO2 + H2O
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:
- (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:
- 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.
- 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.
- 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.