Ethylenetetracarboxylic acid

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Ethylenetetracarboxylic acid
Structural formula
Space-filling model
Names
IUPAC name
2,3-Dicarboxy-but-2-enedioic acid
Identifiers
3D model (JSmol)
ChemSpider
  • 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
  • O=C(O)/C(C(O)=O)=C(C(O)=O)\C(O)=O
Properties
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).
☒N  (what is checkY☒N ?)
Infobox references

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

By removal of four protons, the acid yields the anion C
6
O4−
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
6
H
3
O
8
, C
6
H
2
O2−
8
, and C
6
HO3−
8
, called respectively trihydrogen-, dihydrogen-, and hydrogenethylenetetracarboxylate. The same names are used for the corresponding esters.

The acid can be obtained by hydrolysis of , which in turn can be obtained from with sodium iodide.[1]

Ethylenetetracarboxylic dianhydride, a twofold acid anhydride of this compound, can be formed by direct dehydration at high temperature.[2]

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
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