2,6-Naphthalenedicarboxylic acid
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| Names | |
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| Preferred IUPAC name
Naphthalene-2,6-dicarboxylic acid | |
| Other names
2,6-Naphthalenedicarboxylic acid
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| Identifiers | |
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| 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).
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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 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.
- ↑ 2.0 2.1 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 Deutsch). 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..
