In chemistry, 1,4-benzoquinonetetracarboxylic acid is an organic compound with formula , or (C6O2)(-(CO)OH)4, which can be viewed as deriving from para-benzoquinone through replacement of the four hydrogen atoms by carboxyl functional groups -(CO)OH.
By removal of four protons, the acid is expected to yield the anion , benzoquinonetetracarboxylate, which is one of the oxocarbon anions (consisting solely of oxygen and carbon). By loss of 1 through 3 protons, it forms the anions , , and , called respectively trihydrogen-, dihydrogen-, and hydrogenbenzoquinonetetracarboxylate. The same names are used for the corresponding esters.
Removal of two water molecules gives the compound benzoquinonetetracarboxylic dianhydride, , one of the oxides of carbon. P. R. Hammond (1963), 1,4-Benzoquinone Tetracarboxylic Acid Dianhydride, C10O8: A Strong Acceptor. Science, Vol. 142. no. 3591, p. 502
The acid can be obtained from durene (1,2,4,5-tetramethylbenzene) via dinitropyromellitic and diaminopyromellitic acids. 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. J. U. Nef (1887), Annalen, volume 237, page 19. Cited by Zapadinskii et al. J. U. Nef (1890), Annalen, volume 258, page 282. Cited by Zapadinskii et al.
See also Mellitic acid Tetrahydroxybenzoquinone Benzenehexol
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