4,4'-Dichlorodiphenyl sulfone
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Names | |
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Other names
bis(4-chlorophenyl) sulfone; bis(p-chlorophenyl) sulfone; 4,4'-Dichlorodiphenylsulfone; DCDPS
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Identifiers | |
3D model (JSmol)
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ChemSpider | |
ECHA InfoCard | 100.001.135 |
CompTox Dashboard (EPA)
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Properties | |
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) |
Insoluble | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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:
![](http://upload.wikimedia.org/wikipedia/en/thumb/1/16/Generalrxn.png/800px-Generalrxn.png)
Some of the products include:
![PES](http://upload.wikimedia.org/wikipedia/commons/thumb/3/3c/Products_of_DCDPS.png/500px-Products_of_DCDPS.png)
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}}
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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=
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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}}
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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.