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Mellitic anhydride

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Mellitic anhydride
Mellitic anhydride molecule
Names
IUPAC name
4,9,14-trioxatetracyclo[10.3.0.02,6.07,11]pentadeca-1,6,11-triene-3,5,8,10,13,15-hexone
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C12O9/c13-7-1-2(8(14)19-7)4-6(12(18)21-11(4)17)5-3(1)9(15)20-10(5)16 ☒N
    Key: NNYHMCFMPHPHOQ-UHFFFAOYSA-N ☒N
  • InChI=1/C12O9/c13-7-1-2(8(14)19-7)4-6(12(18)21-11(4)17)5-3(1)9(15)20-10(5)16
    Key: NNYHMCFMPHPHOQ-UHFFFAOYAV
  • O=C2OC(=O)c1c4c(c3c(c12)C(=O)OC3=O)C(=O)OC4=O
Properties
C12O9
Molar mass 288.123 g·mol−1
Appearance colorless solid[1]
Melting point 161 °C; 322 °F; 434 K [1]
Vapor pressure 0.000004 mmHg (20°C)[1]
Hazards
NIOSH (US health exposure limits):
PEL (Permissible)
 none[1]
REL (Recommended)
 TWA 0.005 ppm (0.04 mg/m3) Should be handled in the workplace as an extremely toxic substance.[1]
IDLH (Immediate danger)
 N.D.[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Mellitic anhydride, the anhydride of mellitic acid, is an organic compound with the formula C12O9.

Mellitic anhydride is an oxide of carbon (oxocarbon), like CO2, CO, and C3O2. It is a white sublimable solid, apparently obtained by Liebig and Wöhler in 1830 in their study of mellite ("honey stone"); they assigned it the empiric formula C4O3.[2][3][4] The substance was properly characterized in 1913 by H. Meyer and K. Steiner.[5][6] It retains the aromatic character of the benzene ring.[7][8]

References

  1. ^ a b c d e f NIOSH Pocket Guide to Chemical Hazards. "#0635". National Institute for Occupational Safety and Health (NIOSH).
  2. ^ Wöhler, F. (1826). "Ueber die Honigsteinsäure". Annalen der Physik und Chemie. 83 (7): 325–334. doi:10.1002/andp.18260830706.
  3. ^ Liebig, J.; Wöhler, F. (1830). "Ueber die Zusammensetzung der Honigsteinsäure". Annalen der Physik und Chemie. 94 (2): 161–164. doi:10.1002/andp.18300940202.
  4. ^ Erdmann, O. L.; Marchand, R. F. (1848). "Ueber die Mellithsäure". Journal für Praktische Chemie. 43 (2/3): 129–144. doi:10.1002/prac.18480430113.
  5. ^ Meyer, H.; Steiner, K. (1913). "Über ein neues Kohlenoxyd C12O9" [A new carbon oxide C12O9]. Berichte der Deutschen Chemischen Gesellschaft. 46 (1): 813–815. doi:10.1002/cber.191304601105.
  6. ^ Bugge, G. (1914). "Chemie: Ein neues Kohlenoxyd". Naturwissenschaftliche Wochenschrift. 13/29 (12): 188.
  7. ^ Fowler, P. W.; Lillington, M. (2007). "Mellitic Trianhydride, C12O9: The Aromatic Oxide of Carbon". Journal of Chemical Information and Modeling. 47 (3): 905–908. doi:10.1021/ci600547n.
  8. ^ Ermer, O.; Neudörfl, J. (2000). "Structure of Mellitic Trianhydride". Helvetica Chimica Acta. 83 (1): 300–309. doi:10.1002/(SICI)1522-2675(20000119)83:1<300::AID-HLCA300>3.0.CO;2-L.


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