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
3D model (Jmol)	Interactive image Interactive image
ChemSpider	6373^Y
ECHA InfoCard	100.001.135
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^Y Key: GPAPPPVRLPGFEQ-UHFFFAOYSA-N^Y 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).
Y (what is ^YN ?)
Infobox references

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.

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:

It can also be produced by chlorination of diphenylsulfone.

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:

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:

...
Wikipedia