Phthalic acid

Phthalic acid is an aromatic dicarboxylic acid, with formula C6H4(CO2H)2. Although phthalic acid is of modest commercial importance, the closely related derivative phthalic anhydride is a commodity chemical produced on a large scale. Phthalic acid is one of three isomers of benzenedicarboxylic acid, the others being isophthalic acid and terephthalic acid. Phthalic acid is produced by the catalytic oxidation of naphthalene or ortho-xylene directly to phthalic anhydride and a subsequent hydrolysis of the anhydride. Phthalic acid was first obtained by French chemist Auguste Laurent in 1836 by oxidizing naphthalene tetrachloride. Believing the resulting substance to be a naphthalene derivative, he named it "naphthalic acid". After the Swiss chemist Jean Charles Galissard de Marignac determined its correct formula, Laurent gave it its present name. Manufacturing methods in the nineteenth century included oxidation of naphthalene tetrachloride with nitric acid, or, better, oxidation of the hydrocarbon with fuming sulfuric acid, using mercury or mercury(II) sulfate as a catalyst. Naphthalene on oxidation with potassium permanganate or potassium dichromate gives phthalic acid. It is a dibasic acid, with pKas of 2.89 and 5.51. The monopotassium salt, potassium hydrogen phthalate is a standard acid in analytical chemistry. Typically phthalate esters are prepared from the widely available phthalic anhydride. Reduction of phthalic acid with sodium amalgam in the presence of water gives the 1,3-cyclohexadiene derivative. The toxicity of phthalic acid is moderate with (mouse) of 550 mg/kg. The bacteria Pseudomonas sp. P1 degrades phthalic acid.

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Related concepts (2)

Phthalic acid

Naphthalene

Naphthalene is an organic compound with formula C10H8. It is the simplest polycyclic aromatic hydrocarbon, and is a white crystalline solid with a characteristic odor that is detectable at concentrations as low as 0.08 ppm by mass. As an aromatic hydrocarbon, naphthalene's structure consists of a fused pair of benzene rings. It is the main ingredient of traditional mothballs. In the early 1820s, two separate reports described a white solid with a pungent odor derived from the distillation of coal tar.