2,6-Naphthalenedicarboxylic acid
Names
Preferred IUPAC name
Naphthalene-2,6-dicarboxylic acid
Other names
2,6-Naphthalenedicarboxylic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.013.206
EC Number
  • 214-527-0
UNII
  • 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
  • C1=CC2=C(C=CC(=C2)C(=O)O)C=C1C(=O)O
Properties
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

The conjugate base of 2,6-naphthalenedicarboxylic acid, when heated, isomerizes to the 1,6-isomer, which is readily converted to 1,6-naphthalenedicarboxylic acid.[2] It is also produced by oxidation of 2,6-diisopropylnaphthalene.[3]

References

  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.
  2. ↑ Raecke, Bernhard; Schirp, Hubert (1960). "2,6-Naphthalenedicarboxylic acid". Org. Synth. 40: 71. doi:10.15227/orgsyn.040.0071.
  3. ↑ 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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