Chemistry:Ethylenetetracarboxylic acid

Ethylenetetracarboxylic acid

Names
IUPAC name Ethene-1,1,2,2-tetracarboxylic acid
Identifiers
CAS Number	4363-44-4 Y
3D model (JSmol)	Interactive image
ChemSpider	11636515 N
PubChem CID	12651152
UNII	MV8N94W7XP Y
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) N Key: AIJZIRPGCQPZSL-UHFFFAOYSA-N 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−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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Ethylenetetracarboxylic acid is an organic compound with formula C₆H₄O₈, or (HO(OC)-)₂C=C(-(CO)OH)₂.

By removal of four protons, the acid yields the anion C₆O4−8, 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 C₆H₃O−8, C₆H₂O2−8, and C₆HO3−8, 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.