Terephthaloyl chloride (TCL, 1,4-benzenedicarbonyl chloride) is the

acyl chloride In organic chemistry, an acyl chloride (or acid chloride) is an organic compound with the functional group . Their formula is usually written , where R is a side chain. They are reactive derivatives of carboxylic acids (). A specific example o ...

terephthalic acid 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 tonnes are produced annua ...

. It is a white solid. It is one of two precursors used to make

Kevlar Kevlar (para-aramid) is a strong, heat-resistant synthetic fiber, related to other aramids such as Nomex and Technora. Developed by Stephanie Kwolek at DuPont in 1965, the high-strength material was first used commercially in the early 1970s a ...

(R), the other being ''p''-phenylenediamine. TCL is used as a key component in performance

polymers A polymer (; Greek '' poly-'', "many" + ''-mer'', "part") is a substance or material consisting of very large molecules called macromolecules, composed of many repeating subunits. Due to their broad spectrum of properties, both synthetic an ...

and

aramid Aramid fibers, short for aromatic polyamide, are a class of heat-resistant and strong synthetic fibers. They are used in aerospace and military applications, for ballistic-rated body armor fabric and ballistic composites, in marine cordage, ma ...

fibers, where it imparts flame resistance, chemical resistance, temperature stability, light weight, and very high strength. TCL is also an effective water

scavenger Scavengers are animals that consume dead organisms that have died from causes other than predation or have been killed by other predators. While scavenging generally refers to carnivores feeding on carrion, it is also a herbivorous feeding b ...

, used to stabilize

isocyanates In organic chemistry, isocyanate is the functional group with the formula . Organic compounds that contain an isocyanate group are referred to as isocyanates. An organic compound with two isocyanate groups is known as a diisocyanate. Diisocyan ...

and urethane prepolymers.

Preparation

Terephthalic acid dichloride is produced commercially by the reaction of 1,4-bis(trichloromethyl)benzene with terephthalic acid: : C₆H₄(CCl₃)₂ + C₆H₄(CO₂H)₂ → 2 C₆H₄(COCl)₂ + 2 HCl It can also be obtained by chlorination of

dimethyl terephthalate Dimethyl terephthalate (DMT) is an organic compound with the formula C6H4(COOCH3)2. It is the diester formed from terephthalic acid and methanol. It is a white solid that melts to give a distillable colourless liquid.Richard J. Sheehan "Terepht ...

Use

TCL is used for making various

copolymer In polymer chemistry, a copolymer is a polymer derived from more than one species of monomer. The polymerization of monomers into copolymers is called copolymerization. Copolymers obtained from the copolymerization of two monomer species are some ...

s and

polymers such as

Heracron Aramid fibers, short for aromatic polyamide, are a class of heat-resistant and strong synthetic fibers. They are used in aerospace and military applications, for ballistic-rated body armor fabric and ballistic composites, in marine cordage, ma ...

Twaron Twaron (a brand name of Teijin Aramid) is a para-aramid. It is a heat-resistant and strong synthetic fibre developed in the early 1970s by the Dutch company Akzo Nobel's division Enka BV, later Akzo Industrial Fibers. The research name of the para ...

and

(R):

References

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External links

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Aramid Aramid fibers, short for aromatic polyamide, are a class of heat-resistant and strong synthetic fibers. They are used in aerospace and military applications, for ballistic-rated body armor fabric and ballistic composites, in marine cordage, ma ...

Acyl chlorides Benzene derivatives Monomers