Mellitic anhydride

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Structural formula
Structural formula of mellitic anhydride
General
Surname Mellitic anhydride
other names
  • 2,5,8-trioxatrinden-1,3,4,6,7,9-hexaone
  • Benzo [1,2- c : 3,4- c ': 5,6- c ' '] trifuran-1,3,4,6,7,9-hexaone
  • Mellitic trianhydride
  • Dodecacarbon nonaoxide
Molecular formula C 12 O 9
Brief description

white solid

External identifiers / databases
CAS number 4253-24-1
PubChem 255291
Wikidata Q420390
properties
Molar mass 288.13 g mol −1
Physical state

firmly

density

1.81 g cm −3

Melting point

> 320 ° C (decomposition)

solubility
safety instructions
GHS hazard labeling
no classification available
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Mellitic anhydride (more precisely: mellitic trianhydride ) is the trianhydride of mellitic acid [benzene hexacarboxylic acid C 6 (COOH) 6 ]. This consists only of carbon and oxygen and is therefore formally an oxide of carbon ( dodecacarbon nonaoxide ).

It is a white solid that can be sublimated in a vacuum, which Liebig and Wöhler isolated in their study of mellite ( honey stone ) in 1830 and initially assigned the formula C 4 O 3 . The substance was characterized in 1913 by H. Meyer and K. Steiner. The benzene ring retains its aromatic character.

Mellitic anhydride can be used to improve the thermoplastic properties of the plastic polyethylene terephthalate (PET) or it can be esterified with cellulose or collagen to obtain products with new properties.

Individual evidence

  1. ↑ a b F. Wöhler: "Ueber die Honigsteinsäure", in: Poggendorfs Annalen der Physik und Chemie , 1826 , 83 (7) , pp. 325–334 ( limited preview in the Google book search).
  2. ↑ a b O. Ermer, J. Neudörfl: "Structure of Mellitic Trianhydride", in: Helv. Chim. Acta , 2000 , 83 , pp. 300-309; doi : 10.1002 / (SICI) 1522-2675 (20000119) 83: 1 <300 :: AID-HLCA300> 3.0.CO; 2-L .
  3. ↑ a b c Bugge: "Chemistry: A new carbon oxide", in: Naturwissenschaftliche Wochenschrift , 1914 , 13/29 (12) , March 22, 1914, p. 188. Online version, accessed on December 11, 2009 .
  4. ↑ a b c d Hans Meyer, Karl Steiner: About the mellitic acid . In: Monthly magazine for chemistry . tape 35 , no. 5 , May 1914, p. 475-518 , doi : 10.1007 / BF01519380 .
  5. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
  6. ^ J. Liebig, F. Wöhler: "About the composition of honey-stone acid", in: Poggendorfs Annalen der Physik und Chemie , 1830 , 94 (2) , pp. 161-164 ( limited preview in the Google book search).
  7. ↑ OL Erdmann, RF Marchand: "About the Mellitic Acid", in: Journal for practical chemistry , 1848 , pp. 129-144. Online version, accessed December 11, 2009 ; doi: 10.1002 / prac.18480430113 .
  8. ↑ Hans Meyer, Karl Steiner: "About a new carbon oxide C 12 O 9 ", in: Reports of the German Chemical Society , 1913 , 46 , pp. 813–815; doi: 10.1002 / cber.191304601105 .
  9. ↑ Patrick W. Fowler, Mark Lillington: "Mellitic Trianhydride, C 12 O 9 : The Aromatic Oxide of Carbon", in: Journal of Chemical Information and Modeling , 2007 , 47 (3) , pp. 905-908; doi: 10.1021 / ci600547n .
  10. ↑ Patent US4176101 . ‌
  11. ↑ patent US3526048 . ‌
  12. ↑ patent US4883864 . ‌