4,4'-Dichlorodiphenyl sulfone

4,4'-Dichlorodiphenyl sulfone
Names
	Other names bis(4-chlorophenyl) sulfone; bis(p-chlorophenyl) sulfone; 4,4'-Dichlorodiphenylsulfone; DCDPS
Identifiers
CAS Number	80-07-9;
3D model (JSmol)	Interactive image; Interactive image;
ChemSpider	6373 ;
ECHA InfoCard	100.001.135
CompTox Dashboard (EPA)	DTXSID9024986 ;
	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 Key: GPAPPPVRLPGFEQ-UHFFFAOYSA-N ; 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	287.16 g/mol
Appearance	White solid
Melting point	143 °C (289 °F; 416 K)
Boiling point	250 °C (482 °F; 523 K)
Solubility in water	Insoluble
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

4,4'-Dichlorodiphenyl sulfone, abbreviated as 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

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

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:

Some of the products include:

References

^ Sime, J. G (1960). "The crystal and molecular structure of 4, 4'-dichlorodiphenyl sulphone". Acta Crystallographica. 13 (1): 1–9. doi:10.1107/S0365110X60000017. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)
^ ^a ^b Parker, David (2002). "Polymers, High‐Temperature". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a21_449.pub3. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)
^ Kovacic, Peter (1954). "Chlorination of Aromatic Compounds with Metal Chlorides". Journal of the American Chemical Society. 76 (21): 5491–5494. doi:10.1021/ja01650a069. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)

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.

Synthesis

Uses

References

Further Reading