Ethylenetetracarboxylic dianhydride

Ethylenetetracarboxylic dianhydride
Skeletal formula
Space-filling model
Names
IUPAC name
Furo[3,4-c]furan-1,3,4,6-tetraone
Identifiers
15016-12-3 YesY
Jmol interactive 3D Image
Properties
C6O6
Molar mass 168.06 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Ethylenetetracarboxylic dianhydride is a chemical compound with formula C
6O
6, that can be seen as the twofold anhydride of ethylenetetracarboxylic acid C
6H
4O
8. Its molecular backbone consists of two five-atom maleic anhydride rings, each containing one oxygen atom and four carbon atoms, sharing a pair of carbons. It is one of the oxides of carbon. It is a pale yellow oily liquid, soluble in dichloromethane and trichloromethane.[1]

The compound and its reactions were studied in 1967 by Sauer, Schröder and others.[2][3] Synthesis of the compound by pyrolysis of ethylenetetracarboxilic acid was reported in 1981 by Patterson and others.[4]

The compound was also obtained in 2009 by Taherpour, by microwave pyrolysis of solid Meldrum's acid. Two molecules of the acid are believed to dimerize via an alkene linkage. The meldrum's-acid rings open via hydrolysis to form ethylenetetracarboxylic acid, and then the carboxylic acid units recyclize with different partners to form the dianhydride.[1]

See also

References

  1. 1 2 Avat (Arman) Taherpour (2010), Microwave-assisted solid phase conversion study of Meldrum’s acid to ethylenetetracarboxylic dianhydride (C6O6) Spectrochimica Acta Part A, volume 75, pages 493–497. doi:10.1016/j.saa.2009.10.049
  2. ↑ Jürgen Sauer, Barbara Schröder, Richard Wiemer (1967), Eine Studie der Diels-Alder-Reaktion, VI. Kinetischer Nachweis des Moleküls C6O6 (Dianhydrid der Äthylentetracarbonsäure). Chemische Berichte Volume 100 Issue 1, Pages 306-314 doi:10.1002/cber.19671000135
  3. ↑ Jürgen Sauer, Barbara Schröder, Albrecht Mielert (1967), Eine Studie der Diels-Alder-Reaktion, VII. Reaktionen des Dianhydrids der Äthylentetracarbonsäure (C6O6). Chemische Berichte Volume 100 Issue 1, Pages 315-322 doi:10.1002/cber.19671000136
  4. ↑ John M. Patterson, Nabeel F. Haidar, Loren L. Braun and Walter T. Smith, Jr. (1981), The pyrolytic behavior of ethylenetetracarboxylic acid. Journal of Analytical and Applied Pyrolysis, Volume 2, Issue 4, Pages 331-337 doi:10.1016/0165-2370(81)80005-8
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