2,6-Naphthalenedicarboxylic acid

2,6-Naphthalenedicarboxylic acid
Names
	Preferred IUPAC name Naphthalene-2,6-dicarboxylic acid
	Other names 2,6-Naphthalenedicarboxylic acid
Identifiers
CAS Number	1141-38-4 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:44460;
ChemSpider	13718;
ECHA InfoCard	100.013.206
EC Number	214-527-0;
PubChem CID	14357;
UNII	K3C4DYZ29O ;
CompTox Dashboard (EPA)	DTXSID5029211 ;
	InChI InChI=1S/C12H8O4/c13-11(14)9-3-1-7-5-10(12(15)16)4-2-8(7)6-9/h1-6H,(H,13,14)(H,15,16) Key: RXOHFPCZGPKIRD-UHFFFAOYSA-N;
	SMILES C1=CC2=C(C=CC(=C2)C(=O)O)C=C1C(=O)O;
Properties
Chemical formula	C12H8O4
Molar mass	216.192 g·mol−1
Appearance	colorless solid
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

2,6-Naphthalenedicarboxylic acid is an organic compound with the formula C₁₀H₆(CO₂H)₂. This colorless solid is one of several isomers of naphthalenedicarboxylic acid. It is a precursor to the high performance polyester polyethylene naphthalate (PEN, poly(ethylene-2,6-naphthalene dicarboxylate)).^[1] It is also used in the synthesis of some metal-organic frameworks.

Preparation

It was first prepared by Robert Evert and Victor Merz [de] in 1876 by hydrolysis of 2,6-dicyanonaphthalene.^[2]^[3]

1,8-Naphthalenedicarboxylic acid can be isomerized to 2,6-naphthalenedicarboxylic acid via the intermediacy of the dipotassium dicarboxylates.^[2] It is also produced by oxidation of 2,6-diisopropylnaphthalene.^[4]

References

^ Lillwitz, L. D. (2001). "Production of Dimethyl-2,6-Naphthalenedicarboxylate: Precursor to Polyethylene Naphthalate". Applied Catalysis A: General. 221 (1–2): 337–358. doi:10.1016/S0926-860X(01)00809-2.
^ ^a ^b Raecke, Bernhard; Schirp, Hubert (1960). "2,6-Naphthalenedicarboxylic acid". Org. Synth. 40: 71. doi:10.15227/orgsyn.040.0071.
^ Ebert, R.; Merz, V. (1876). "Ueber zwei Disulfosäuren des Naphtalins und einige ihrer Derivate" [About Two Sulfonic Acids of Naphthalene and Some Derivatives]. Berichte der deutschen chemischen Gesellschaft (in German). 9 (1): 592–612. doi:10.1002/cber.187600901186. ISSN 0365-9496.
^ Gerd Collin; Hartmut Höke; Helmut Greim (2003). "Naphthalene and Hydronaphthalenes". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. ISBN 978-3527306732..

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[1] Lillwitz, L. D. (2001). "Production of Dimethyl-2,6-Naphthalenedicarboxylate: Precursor to Polyethylene Naphthalate". Applied Catalysis A: General. 221 (1–2): 337–358. doi:10.1016/S0926-860X(01)00809-2.

[:0-2] Raecke, Bernhard; Schirp, Hubert (1960). "2,6-Naphthalenedicarboxylic acid". Org. Synth. 40: 71. doi:10.15227/orgsyn.040.0071.

[3] Ebert, R.; Merz, V. (1876). "Ueber zwei Disulfosäuren des Naphtalins und einige ihrer Derivate" [About Two Sulfonic Acids of Naphthalene and Some Derivatives]. Berichte der deutschen chemischen Gesellschaft (in German). 9 (1): 592–612. doi:10.1002/cber.187600901186. ISSN 0365-9496.

[Ullmann-4] Gerd Collin; Hartmut Höke; Helmut Greim (2003). "Naphthalene and Hydronaphthalenes". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. ISBN 978-3527306732..

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