Ethylenetetracarboxylic acid

Ethylenetetracarboxylic acid
Names
	IUPAC name 2,3-Dicarboxy-but-2-enedioic acid
Identifiers
CAS Number	4363-44-4 ;
3D model (JSmol)	Interactive image;
ChemSpider	11636515 ;
PubChem CID	12651152;
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−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	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
₆O⁴⁻
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
₂O²⁻
₈, and C
₆HO³⁻
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.[1]

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

References

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.
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

This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.

[zapa-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.

[patt-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