4,4′-Dichlorodiphenyl sulfone (DCDPS) is an
organic compound
Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...
with the formula (ClC
6H
4)
2SO
2. Classified as a
sulfone
In organic chemistry, a sulfone is a organosulfur compound containing a sulfonyl () functional group attached to two carbon atoms. The central hexavalent sulfur atom is double-bonded to each of two oxygen atoms and has a single bond to each of ...
, this white solid is most commonly used as a precursor to polymers that are rigid and temperature-resistant such as PES and Udel.
Synthesis and reactions
DCDPS is synthesized via
sulfonation
In organic chemistry, aromatic sulfonation is a reaction in which a hydrogen atom on an arene is replaced by a sulfonic acid () group. Together with nitration and chlorination, aromatic sulfonation is a widely used electrophilic aromatic substi ...
of
chlorobenzene
Chlorobenzene (abbreviated PhCl) is an aryl chloride and the simplest of the chlorobenzenes, consisting of a benzene ring substituted with one chlorine atom. Its chemical formula is C6H5Cl. This colorless, flammable liquid is a common solvent a ...
with
sulfuric acid
Sulfuric acid (American spelling and the preferred IUPAC name) or sulphuric acid (English in the Commonwealth of Nations, Commonwealth spelling), known in antiquity as oil of vitriol, is a mineral acid composed of the elements sulfur, oxygen, ...
, often in the presence of various additives to optimize the formation of the 4,4′-isomer:
:ClC
6H
5 + SO
3 → (ClC
6H
4)
2SO
2 + H
2O
It can also be produced by chlorination of
diphenylsulfone.
With chloride substituents susceptible to substitution, DCDPS is useful in the production of
polysulfone
Polysulfones are a family of high performance thermoplastics. These polymers are known for their toughness and stability at high temperatures. Technically used polysulfones contain an aryl- SO2-aryl subunit. Due to the high cost of raw material ...
s. One such polymer,
victrex
Victrex plc is a United Kingdom, British-based supplier of high performance polymers. It is a constituent of the FTSE 250. The company's headquarters and manufacturing facilities are based in the UK with technical and customer support facilities ...
, is prepared by the reaction of DCDPS with 4,4′-sulfonylbisphenol (
bisphenol S). Similarly DCDPS reacts with
bisphenol-A
Bisphenol A (BPA) is a chemical compound primarily used in the manufacturing of various plastics. It is a colourless solid which is Solubility, soluble in most common organic solvents, but has very poor solubility in water. BPA is produced on a ...
to give the polymer called
Udel. These condensations are represented as follows:
:''n'' (ClC
6H
4)
2SO
2 + ''n'' NaO−X−ONa →
O−X−OC6H4)2SO2sub>''n'' + 2''n'' NaCl
Further reading
*
*
Radel PPSU, Veradel PESU and Acudel modified PPSU Design Guide by Solvay
References
{{DEFAULTSORT:Dichlorodiphenyl Sulfone, 4, 4
Benzosulfones
4-Chlorophenyl compounds