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phthalic acid : ウィキペディア英語版
phthalic acid

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Phthalic acid is an aromatic dicarboxylic acid, with formula C6H4(CO2H)2. It is an isomer of isophthalic acid and terephthalic acid. Although phthalic acid is of modest commercial importance, the closely related derivative phthalic anhydride is a commodity chemical produced on a large scale.〔Peter M. Lorz, Friedrich K. Towae, Walter Enke, Rudolf Jäckh, Naresh Bhargava, Wolfgang Hillesheim "Phthalic Acid and Derivatives" in Ullmann's Encyclopedia of Industrial Chemistry, 2007, Wiley-VCH, Weinheim. 〕
==Production==
Phthalic acid is produced by the catalytic oxidation of naphthalene 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".〔See:
* Auguste Laurent (1836) ("Sur l'acide naphtalique et ses combinaisons" ) (On naphthalic acid and its compounds), ''Annales de Chimie et de Physique'', 61 : 113-125. (Note: The empirical formulae of the compounds that were analyzed in this article are incorrect, in part because, during this period, chemists used incorrect atomic masses for carbon (6 instead of 12) and other elements.)
* Reprinted in German as: Auguste Laurent (1836) ("Ueber Naphthalinsäure und ihre Verbindungen" ) (On naphthalenic acid and its compounds), ''Annalen der Pharmacie'', 19 (1) : 38-50; for the preparation of phthalic acid, see page 41.〕 After the Swiss chemist Jean Charles Galissard de Marignac determined its correct formula,〔C. de Marignac (1841) ("Ueber die Naphtalinsäure und ein bei ihrer Darstellung entstehendes flüchtiges Produkt" ) (On naphthalinic acid and a volitile product that arises during its preparation), ''Annalen der Chemie und Pharmacie'', 38 (1) : 13-20. (Note: Again, Marignac's empirical formulae are wrong because chemists at this time used incorrect atomic masses.)〕 Laurent gave it its present name.〔See:
* Auguste Laurent (1841) ("Sur de nouvelles combinaisons nitrogénées de la naphtaline et sur les acides phtalique et nitrophtalique" ) (On new nitrogenous compounds of naphthalene, and on phthalic acid and nitrophthalic acid), ''Revue Scientifique et Industrielle'', 6 : 76-99; on page 92, Laurent coins the name "acide phtalique" (phthalic acid) and admits that his earlier empirical formula for phthalic acid was wrong.
* Reprinted in German as: Auguste Laurent (1842) ("Ueber neue stickstoffhaltige Verbindungen des Naphtalins, über Phtalinsäure und Nitrophtalinsäure" ) (On new nitrogenous compounds of naphthalene, on phthalic acid and nitrophthalic acid), ''Annalen der Chemie und Pharmacie'', 41 (1) : 98-114; on page 108, Laurent coins the name "Phtalinsäure" (phthalic acid).〕 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.

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