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Ethylenetetracarboxylic acid

Names
IUPAC name Ethene-1,1,2,2-tetracarboxylic acid
Identifiers
CAS Number	4363-44-4
3D model (JSmol)	Interactive image
ChemSpider	11636515
PubChem CID	12651152
UNII	MV8N94W7XP
CompTox Dashboard (EPA)	DTXSID20505724
InChI InChI=1S/C6H4O8/c7-3(8)1(4(9)10)2(5(11)12)6(13)14/h(H,7,8)(H,9,10)(H,11,12)(H,13,14)Key: AIJZIRPGCQPZSL-UHFFFAOYSA-N InChI=1/C6H4O8/c7-3(8)1(4(9)10)2(5(11)12)6(13)14/h(H,7,8)(H,9,10)(H,11,12)(H,13,14)Key: AIJZIRPGCQPZSL-UHFFFAOYAE
SMILES O=C(O)/C(C(O)=O)=C(C(O)=O)\C(O)=O
Properties
Chemical formula	C6H4O8
Molar mass	204.090 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). N verify (what is  ?) Infobox references

Ethylenetetracarboxylic acid is an organic compound with formula C
₆H
₄O
₈, or (HO(OC)-)₂C=C(-(CO)OH)₂.

By removal of four protons, the acid yields the anion C
₆O
₈, ethylenetetracarboxylate, which is one of the oxocarbon anions (consisting solely of oxygen and carbon). By loss of 1 through 3 protons, it forms the anions C
₆H
₃O
₈, C
₆H
₂O
₈, and C
₆HO
₈, called respectively trihydrogen-, dihydrogen-, and hydrogenethylenetetracarboxylate. The same names are used for the corresponding esters.

The acid can be obtained by hydrolysis of tetraethyl ethylenetetracarboxylate, which in turn can be obtained from diethyl dibromomalonate with sodium iodide.

Ethylenetetracarboxylic dianhydride, a twofold acid anhydride of this compound, can be formed by direct dehydration at high temperature.

References

1. B. I. Zapadinskii, B. I. Liogon'kii, and A. A. Berlin (1973), Syntheses of Tetracarboxylic Acids. Russian Chemical Reviews, volume 42 issue 11, page 939. Online version accessed on 2010-01-03.
2. John M. Patterson, Nabeel F. Haidar, Loren L. Braun and Walter T. Smith, Jr. (1981), The pyrolytic behavior of ethylenetetracarboxylic acid. Journal of Analytical and Applied Pyrolysis, Volume 2, Issue 4, Pages 331-337 doi:10.1016/0165-2370(81)80005-8

• Carboxylic acids