2,6-Naphthalenedicarboxylic acid

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2,6-Naphthalenedicarboxylic acid
2,6-Naphthalenedicarboxylic acid.svg
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 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 214-527-0
PubChem CID
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
Appearancecolorless solid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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

  1. ↑ Lillwitz, L. D. (2001). "Production of Dimethyl-2,6-Naphthalenedicarboxylate: Precursor to Polyethylene Naphthalate". Applied Catalysis A: General. 221 (1–2): 337–358. Bibcode:2001AppCA.221..337L. doi:10.1016/S0926-860X(01)00809-2.
  2. 1 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.
  4. ↑ Gerd Collin; Hartmut Höke; Helmut Greim (2003). "Naphthalene and Hydronaphthalenes". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. ISBN   978-3-527-30673-2..


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