Terephthaloyl chloride: Difference between revisions
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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 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. |
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==Properties== |
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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 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. |
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==Preparation== |
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Terephthalic acid dichloride can be obtained by chlorination of dimethyl terephthalate.<ref>{{Cite patent| country = EP| number = 0095698| Typ = Erteilung| title = Verfahren zur Herstellung von Terephthalsäure- und Isophthalsäuredichlorid| A-Datum =1983-05-24| V-Datum = 1985-09-4| invent1 = Walter Böckmann, Friedrich Brühne, Karl-August Lipper | Anmelder = [[Bayer AG]]| DB=Google}}</ref> |
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==Use== |
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TCL is used for making various [[copolymer]]s and [[aramid]] polymers such as [[Heracron]], [[Twaron]] and [[Kevlar]](R): |
TCL is used for making various [[copolymer]]s and [[aramid]] polymers such as [[Heracron]], [[Twaron]] and [[Kevlar]](R): |
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[[Image:Kevlar chemical synthesis.png|center|566px|The reaction of 1,4-phenyl-diamine (''para''-phenylenediamine) with terephthaloyl chloride yielding Kevlar(R)]] |
[[Image:Kevlar chemical synthesis.png|center|566px|The reaction of 1,4-phenyl-diamine (''para''-phenylenediamine) with terephthaloyl chloride yielding Kevlar(R)]] |
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Revision as of 15:48, 15 November 2017
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| Names | |
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| 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)
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| ChemSpider | |
| ECHA InfoCard | 100.002.572 |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| 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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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 Template:Carbon8Template:Hydrogen4Template:Chlorine2Template:Oxygen2.
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):
References
- ^ a b 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"