Formula C12H8Cl2O2S Appearance White solid | Molar mass 287.16 g/mol | |
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4,4'-Dichlorodiphenyl sulfone (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.
Contents
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 + H2OIt can also be produced by chlorination of diphenylsulfone.
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:
(ClC6H4)2SO2 + HO-X-OH → 1/n [(O-X-OC6H4)2SO2]n + 2 HClUdel 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: