Terephthaloyl chloride

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Terephthaloyl chloride
Skeletal formula
Ball-and-stick model of the terephthaloyl chloride molecule
IUPAC name
Terephthaloyl dichloride
Systematic IUPAC name
Benzene-1,4-dicarbonyl dichloride
Other names
1,4-Benzenedicarbonyl chloride, Benzene-1,4-dicarbonyl chloride, Terephthalic acid dichloride, Terephthaloyl dichloride, p-Phthalyl chloride, TCL
100-20-9 YesY
ChemSpider 7207 YesY
Jmol interactive 3D Image
PubChem 7488
Molar mass 203.02 g/mol
Density 1.34 g/cm3
Melting point 81.5 to 83 °C (178.7 to 181.4 °F; 354.6 to 356.1 K)
Boiling point 265 °C (509 °F; 538 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Terephthaloyl chloride (TCL, 1,4-benzenedicarbonyl chloride) is the acid chloride of terephthalic acid and is one of two monomers used to make Kevlar(R), the other being p-phenylenediamine. Its CAS reference number is 100-20-9 and its chemical formula is C8H4Cl2O2.

TCL is used as a key component in performance polymers and aramid fibers, where it imparts flame resistance, chemical resistance, temperature stability, light weight, and very high strength. TCL is also an effective water scavenger, used to stabilize isocyanates and urethane prepolymers.

TCL is a white crystalline solid at room temperature, soluble in common organic solvents. Its melting point is 81.5-83 °C, its boiling point is 265 °C. It is corrosive.

TCL is used for making various copolymers and aramid polymers such as Heracron, Twaron and Kevlar(R):

The reaction of 1,4-phenyl-diamine (para-phenylenediamine) with terephthaloyl chloride yielding Kevlar(R)

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