4,4'-Dichlorodiphenyl sulfone
Encyclopedia
4,4'-Dichlorodiphenyl sulfone, abbreviated as DCDPS, is an organic sulfone with the formula (ClC6H4)2SO2. It is most commonly used as a precursor to polymers that are rigid and temperature resistant such as Victrex or Udel. The compound is readily available through chemical suppliers in its powdered form.
with sulfuric acid
at a temperature of 200-250 °C. The reaction can be done in the presence of boric acid
or trifluoromethanesulfonic acid
, which increase the yield DCDPS by reducing the formation of the 2,4 and 3,4 isomers. The reaction goes to completion in approximately 10 hours and produces a high yield of 4,4'-dichlorodiphenyl sulfone.
, 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. 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 Victrex. Like Udel, Victrex is a rigid and thermally resistant material with numerous applications.
The general polymerization reaction:
Some of the products include:
Synthesis
DCDPS can be synthesized by treating chlorobenzeneChlorobenzene
Chlorobenzene is an aromatic organic compound with the chemical formula C6H5Cl. This colorless, flammable liquid is a common solvent and a widely used intermediate in the manufacture of other chemicals.-Uses:...
with sulfuric acid
Sulfuric acid
Sulfuric acid is a strong mineral acid with the molecular formula . Its historical name is oil of vitriol. Pure sulfuric acid is a highly corrosive, colorless, viscous liquid. The salts of sulfuric acid are called sulfates...
at a temperature of 200-250 °C. The reaction can be done in the presence of boric acid
Boric acid
Boric acid, also called hydrogen borate or boracic acid or orthoboric acid or acidum boricum, is a weak acid of boron often used as an antiseptic, insecticide, flame retardant, as a neutron absorber, and as a precursor of other chemical compounds. It exists in the form of colorless crystals or a...
or trifluoromethanesulfonic acid
Trifluoromethanesulfonic acid
Trifluoromethanesulfonic acid, also known as triflic acid, TFMS, TFSA, HOTf or TfOH, is a sulfonic acid with the chemical formula CF3SO3H. It is one of the strongest acids. Triflic acid is mainly used in research as a catalyst for esterification.-Properties:Triflic acid is a hygroscopic, colorless...
, which increase the yield DCDPS by reducing the formation of the 2,4 and 3,4 isomers. The reaction goes to completion in approximately 10 hours and produces a high yield of 4,4'-dichlorodiphenyl sulfone.
Uses
DCDPS is used as a starting material in the polymerization of compounds such as Udel, VictrexVictrex
Victrex plc is a leading British-based producer of high performance polymers. It is a constituent of the FTSE 250.-History:The company was established in 1993 by way of a management buyout of the PEEK polymer business of Imperial Chemical Industries plc. It was first listed on the London Stock...
, and Radel R. The polymerization occurs through a nucleophilic substitution reaction of DCDPS with difunctional nucleophiles. With bisphenol A
Bisphenol A
Bisphenol A is an organic compound with two phenol functional groups. It is used to make polycarbonate plastic and epoxy resins, along with other applications....
in dimethyl sulfoxide
Dimethyl sulfoxide
Dimethyl sulfoxide is an organosulfur compound with the formula 2SO. This colorless liquid is an important polar aprotic solvent that dissolves both polar and nonpolar compounds and is miscible in a wide range of organic solvents as well as water...
, DCDPS forms a material called Udel. 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
Bisphenol S
Bisphenol S is an organic compound with the formula 2SO2. It has two phenol functional groups on either side of a sulfonyl group...
to form Victrex. Like Udel, Victrex is a rigid and thermally resistant material with numerous applications.
The general polymerization reaction:
Some of the products include: