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Mellitic anhydride

From Wikipedia, the free encyclopedia
Mellitic anhydride
Mellitic anhydride molecule
Names
Preferred IUPAC name
Benzo[1,2-c:3,4-c′:5,6-c′′]trifuran-1,3,4,6,7,9-hexone
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • 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 mass288.123 g·mol−1
Appearancecolorless solid[1]
Melting point161 °C; 322 °F; 434 K[1]
Vapor pressure0.000004 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 theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

Mellitic anhydride, theanhydride ofmellitic acid, is anorganic compound with the formula C12O9.

Containing no other elements (e.g., hydrogen) besides carbon and oxygen, mellitic anhydride is anoxide ofcarbon (oxocarbon), and, along withCO2,CO, andC3O2, is one of the only four that are reasonably stable under standard conditions. It is a white sublimable solid, apparently obtained byJustus Liebig andFriedrich Wöhler in 1830 in their study ofmellite ("honey stone") and has theempirical 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

[edit]
  1. ^abcdefNIOSH Pocket Guide to Chemical Hazards."#0635".National Institute for Occupational Safety and Health (NIOSH).
  2. ^Wöhler, F. (1826)."Ueber die Honigsteinsäure"(PDF).Annalen der Physik und Chemie.83 (7):325–334.Bibcode:1826AnP....83..325W.doi:10.1002/andp.18260830706.
  3. ^Liebig, J.;Wöhler, F. (1830)."Ueber die Zusammensetzung der Honigsteinsäure"(PDF).Annalen der Physik und Chemie.94 (2):161–164.Bibcode:1830AnP....94..161L.doi:10.1002/andp.18300940202.
  4. ^Erdmann, O. L.; Marchand, R. F. (1848)."Ueber die Mellithsäure"(PDF).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.PMID 17315989.
  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.
Common oxides
Exotic oxides
Polymers
Compounds derived from oxides
Mixed oxidation states
+1 oxidation state
+2 oxidation state
+3 oxidation state
+4 oxidation state
+5 oxidation state
+6 oxidation state
+7 oxidation state
+8 oxidation state
Related
Oxides are sorted byoxidation state.Category:Oxides


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