Terephthaloyl chloride: Difference between revisions

Terephthaloyl chloride
Names
	Preferred IUPAC name Benzene-1,4-dicarbonyl dichloride
	Other names Terephthaloyl dichloride; 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
Appearance	white 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). verify (what is ?) Infobox references

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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.

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:

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.
^ Pfoertner, Karl-Heinz (2000). "Photochemistry". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a19_573. ISBN 978-3527306732.
^ EP patent 0095698, Walter Böckmann, Friedrich Brühne, Karl-August Lipper, "Verfahren zur Herstellung von Terephthalsäure- und Isophthalsäuredichlorid", published 1983-12-07, assigned to Bayer AG

External links

Aramid

[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] Pfoertner, Karl-Heinz (2000). "Photochemistry". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a19_573. ISBN 978-3527306732.

[3] EP patent 0095698, Walter Böckmann, Friedrich Brühne, Karl-August Lipper, "Verfahren zur Herstellung von Terephthalsäure- und Isophthalsäuredichlorid", published 1983-12-07, assigned to Bayer AG

[1]

[2]

[3]

@@ Line 1: / Line 1: @@
-{{unreferenced|date=November 2014}}
 {{chembox
+| Verifiedfields = changed
 | Watchedfields = changed
 | verifiedrevid = 470602333
@@ Line 8: / Line 8: @@
 | ImageFile1 = Terephthaloyl chloride 3D ball.png
 | ImageAlt1 = Ball-and-stick model of the terephthaloyl chloride molecule
+| PIN = Benzene-1,4-dicarbonyl dichloride<ref name=iupac2013>{{cite book | title =  Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = [[Royal Society of Chemistry|The Royal Society of Chemistry]] | date = 2014 | location = Cambridge | page = 797 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4}}</ref>
-| IUPACName = Terephthaloyl dichloride
+| OtherNames = Terephthaloyl dichloride<ref name=iupac2013 /><br />1,4-Benzenedicarbonyl chloride<br />Benzene-1,4-dicarbonyl chloride<br />Terephthalic acid dichloride<br />Terephthaloyl dichloride<br />''p''-Phthalyl chloride<br />TCL
-| SystematicName = Benzene-1,4-dicarbonyl dichloride
-| OtherNames = 1,4-Benzenedicarbonyl chloride, Benzene-1,4-dicarbonyl chloride, Terephthalic acid dichloride, Terephthaloyl dichloride, p-Phthalyl chloride, TCL
 |Section1={{Chembox Identifiers
 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
@@ Line 22: / Line 21: @@
 | CASNo_Ref = {{cascite|correct|CAS}}
 | CASNo = 100-20-9
+| UNII_Ref = {{fdacite|changed|FDA}}
+| UNII = G247CO9608
 | PubChem = 7488
 | SMILES = O=C(Cl)c1ccc(C(Cl)=O)cc1
@@ Line 28: / Line 29: @@
 | Formula = C<sub>8</sub>H<sub>4</sub>Cl<sub>2</sub>O<sub>2</sub>
 | MolarMass = 203.02 g/mol
-| Appearance =
+| Appearance =  white solid
 | Density = 1.34 g/cm<sup>3</sup>
 | MeltingPtC = 81.5 to 83
-| Melting_notes =
+| MeltingPt_notes =
 | BoilingPtC = 265
 | Solubility =
@@ Line 42: / Line 43: @@
 }}
-'''Terephthaloyl chloride''' ('''TCL''', '''1,4-benzenedicarbonyl chloride''') is the acid chloride of [[terephthalic acid]] and is one of two [[monomer]]s used to make [[Kevlar]](R), the other being [[p-phenylenediamine]]. Its [[CAS reference number]] is 100-20-9 and its chemical formula is {{Carbon}}<sub>8</sub>{{Hydrogen}}<sub>4</sub>{{Chlorine}}<sub>2</sub>{{Oxygen}}<sub>2</sub>.
+'''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|''p''-phenylenediamine]]. TCL is used as a key component in performance [[Polymer|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 (chemistry)|scavenger]], used to stabilize [[Isocyanate|isocyanates]] and [[Ethyl carbamate|urethane]] prepolymers.
+==Preparation==
-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.
+Terephthalic acid dichloride is produced commercially by the reaction of [[1,4-Bis(trichloromethyl)benzene|1,4-bis(trichloromethyl)benzene]] with terephthalic acid:<ref>{{Ullmann |doi=10.1002/14356007.a19_573|title=Photochemistry|year=2000|last1=Pfoertner|first1=Karl-Heinz}}</ref>
+: C<sub>6</sub>H<sub>4</sub>(CCl<sub>3</sub>)<sub>2</sub>  +  C<sub>6</sub>H<sub>4</sub>(CO<sub>2</sub>H)<sub>2</sub>  →  2 C<sub>6</sub>H<sub>4</sub>(COCl)<sub>2</sub> +  2 HCl
+It can also be obtained by chlorination of [[dimethyl terephthalate]].<ref>{{Cite patent| country = EP| number = 0095698| status = patent| title = Verfahren zur Herstellung von Terephthalsäure- und Isophthalsäuredichlorid| fdate =1983-05-24| pubdate = 1983-12-07| invent1 = Walter Böckmann, Friedrich Brühne, Karl-August Lipper | assign = [[Bayer AG]]}}</ref>
-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.
+==Use==
-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]]:
-[[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]]
+==References==
+{{Reflist}}
 ==External links==
@@ Line 56: / Line 63: @@
 [[Category:Acyl chlorides]]
-[[Category:Aromatic compounds]]
+[[Category:Benzene derivatives]]
 [[Category:Monomers]]