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
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.001.135
UNII
  • InChI=1S/C12H8Cl2O2S/c13-9-1-5-11(6-2-9)17(15,16)12-7-3-10(14)4-8-12/h1-8H checkY
    Key: GPAPPPVRLPGFEQ-UHFFFAOYSA-N checkY
  • 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
  • O=S(=O)(c1ccc(Cl)cc1)c2ccc(Cl)cc2
  • O=S(=O)(c1ccc(Cl)cc1)c2ccc(Cl)cc2
Properties
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)
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 checkY☒N ?)
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. "Polymers, High‐Temperature". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a21_449.pub3.
  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.
This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.