Terephthaloyl chloride

Terephthaloyl chloride
Names
	Preferred IUPAC name Benzene-1,4-dicarbonyl dichloride[1]
	Other names Terephthaloyl dichloride[1]; 1,4-Benzenedicarbonyl chloride; Benzene-1,4-dicarbonyl chloride; Terephthalic acid dichloride; Terephthaloyl dichloride; p-Phthalyl chloride; TCL
Identifiers
CAS Number	100-20-9 ;
3D model (JSmol)	Interactive image;
ChemSpider	7207 ;
ECHA InfoCard	100.002.572
PubChem CID	7488;
UNII	G247CO9608 ;
CompTox Dashboard (EPA)	DTXSID7026653 ;
	InChI InChI=1S/C8H4Cl2O2/c9-7(11)5-1-2-6(4-3-5)8(10)12/h1-4H Key: LXEJRKJRKIFVNY-UHFFFAOYSA-N ; InChI=1/C8H4Cl2O2/c9-7(11)5-1-2-6(4-3-5)8(10)12/h1-4H Key: LXEJRKJRKIFVNY-UHFFFAOYAY;
	SMILES O=C(Cl)c1ccc(C(Cl)=O)cc1;
Properties
Chemical formula	C8H4Cl2O2
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.

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.

Properties

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.

Preparation

Terephthalic acid dichloride can be obtained by chlorination of dimethyl terephthalate.[2]

Use

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)

References

Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 797. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
EP 0095698, Walter Böckmann, Friedrich Brühne, Karl-August Lipper, "Verfahren zur Herstellung von Terephthalsäure- und Isophthalsäuredichlorid"

External links

Aramid

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[iupac2013-1] Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 797. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.

[2] EP 0095698, Walter Böckmann, Friedrich Brühne, Karl-August Lipper, "Verfahren zur Herstellung von Terephthalsäure- und Isophthalsäuredichlorid"