4,4'-Dichlorodiphenyl sulfone

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4,4'-Dichlorodiphenyl sulfone
4,4'-Dichlorodiphenyl sulfone.svg
Identifiers
CAS number 80-07-9
PubChem 6625
ChemSpider 6373 YesY
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C12H8Cl2O2S
Molar mass 287.16 g mol−1
Appearance White solid
Melting point 143 °C (289 °F; 416 K)
Boiling point 250 °C (482 °F; 523 K)
Solubility in water Insoluble
Hazards
MSDS External MSDS
Except where noted otherwise, 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[edit]

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[edit]

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:

Generalrxn.png

Some of the products include:

PES

References[edit]

  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. ^ a b 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[edit]