Terephthaloyl chloride

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Terephthaloyl chloride
Terephthaloylchloride.png
Terephthaloyl chloride 3D ball.png
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
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.002.572 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C8H4Cl2O2/c9-7(11)5-1-2-6(4-3-5)8(10)12/h1-4H Yes check.svgY
    Key: LXEJRKJRKIFVNY-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C8H4Cl2O2/c9-7(11)5-1-2-6(4-3-5)8(10)12/h1-4H
    Key: LXEJRKJRKIFVNY-UHFFFAOYAY
  • O=C(Cl)c1ccc(C(Cl)=O)cc1
Properties
C8H4Cl2O2
Molar mass 203.02 g/mol
Appearancewhite solid
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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Terephthaloyl chloride (TCL, 1,4-benzenedicarbonyl chloride) is the acyl chloride of terephthalic acid. It is a white solid at room temperature. It is one of two precursors used to make Kevlar, 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.

Contents

Preparation

Terephthalic acid dichloride is produced commercially by the reaction of 1,4-bis(trichloromethyl)benzene with terephthalic acid: [2]

C6H4(CCl3)2 + C6H4(CO2H)2 → 2 C6H4(COCl)2 + 2 HCl

It can also be obtained by chlorination of dimethyl terephthalate. [3]

Use

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

The reaction of 1,4-phenyl-diamine (para-phenylenediamine) with terephthaloyl chloride yielding Kevlar Kevlar chemical synthesis.png
The reaction of 1,4-phenyl-diamine (para-phenylenediamine) with terephthaloyl chloride yielding Kevlar

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Terephthalic acid is an organic compound with formula C6H4(CO2H)2. This white solid is a commodity chemical, used principally as a precursor to the polyester PET, used to make clothing and plastic bottles. Several million tons are produced annually. The common name is derived from the turpentine-producing tree Pistacia terebinthus and phthalic acid.

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<span class="mw-page-title-main">4,4'-Dichlorodiphenyl sulfone</span> Chemical compound

4,4′-Dichlorodiphenyl sulfone (DCDPS) is an organic compound with the formula (ClC6H4)2SO2. Classified as a sulfone, this white solid is most commonly used as a precursor to polymers that are rigid and temperature-resistant such as PES or Udel.

<span class="mw-page-title-main">Cyclohexanedimethanol</span> Chemical compound

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1,4-Bis(trichloromethyl)benzene is an organic compound with the formula C6H4(CCl3)2. A white solid, it is prepared industrially by chlorination of para-xylene. It reacts with terephthalic acid to give terephthaloyl chloride, a precursor to Kevlar. It also reacts with sulfur dioxide to give the same acid chloride and thionyl chloride. It reacts with hydrogen fluoride in 1,2-dichloroethane to form 1,4-bis(chlorodifluoromethyl)benzene in a yield of 79%.

References

  1. 1 2 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 (inactive 2024-06-29). ISBN   978-0-85404-182-4.{{cite book}}: CS1 maint: DOI inactive as of June 2024 (link)
  2. Pfoertner, Karl-Heinz (2000). "Photochemistry". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a19_573. ISBN   978-3527306732.
  3. EPpatent 0095698,Walter Böckmann, Friedrich Brühne, Karl-August Lipper,"Verfahren zur Herstellung von Terephthalsäure- und Isophthalsäuredichlorid",published 1983-12-07, assigned to Bayer AG