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Mellitic anhydride
Names
Preferred IUPAC name
Benzo[1,2-c :3,4-c ′:5,6-c ′′]trifuran-1,3,4,6,7,9-hexone
Identifiers
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
C 12 O 9
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):
none
[1]
TWA 0.005 ppm (0.04 mg/m3) Should be handled in the workplace as an extremely toxic substance.
[1]
N.D.
[1]
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
Mellitic anhydride , the
anhydride of
mellitic acid , is an
organic compound with the formula C12 O9 .
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
C3 O2 , 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 C4 O3 .
[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
^
a
b
c
d
e
f NIOSH Pocket Guide to Chemical Hazards.
"#0635" .
National Institute for Occupational Safety and Health (NIOSH).
^
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 .
^
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 .
^ 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 .
^ Meyer, H.; Steiner, K. (1913).
"Über ein neues Kohlenoxyd C12 O9 " [A new carbon oxide C12 O9 ].
Berichte der Deutschen Chemischen Gesellschaft . 46 (1): 813–815.
doi :
10.1002/cber.191304601105 .
^ Bugge, G. (1914).
"Chemie: Ein neues Kohlenoxyd" . Naturwissenschaftliche Wochenschrift . 13/29 (12): 188.
^ Fowler, P. W.; Lillington, M. (2007). "Mellitic Trianhydride, C12 O9 : The Aromatic Oxide of Carbon". Journal of Chemical Information and Modeling . 47 (3): 905–908.
doi :
10.1021/ci600547n .
PMID
17315989 .
^ 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