Mellitic anhydride

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

Mellitic anhydride

Names
IUPAC name 4,9,14-trioxatetracyclo[10.3.0.0^2,6.0^7,11]pentadeca-1,6,11-triene-3,5,8,10,13,15-hexone
Preferred IUPAC name benzo[1,2-c:3,4-c′:5,6-c′′]trifuran-1,3,4,6,7,9-hexone
Identifiers
CAS Number	4253-24-1^N
3D model (JSmol)	Interactive image
ChemSpider	223826^N
PubChem CID	255291
CompTox Dashboard (EPA)	DTXSID40292184
InChI 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
SMILES O=C2OC(=O)c1c4c(c3c(c12)C(=O)OC3=O)C(=O)OC4=O
Properties
Chemical formula	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 ^YN ?)
Infobox references

Containing no other elements (e.g., hydrogen) besides carbon and oxygen, mellitic anhydride is an oxide of carbon (oxocarbon), and, along with CO₂, CO, and C₃O₂, is one of the only four that are reasonably stable under standard conditions. It is a white sublimable solid, apparently obtained by Justus Liebig and Friedrich Wöhler in 1830 in their study of mellite ("honey stone") and has the empirical 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. 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.