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Phthalic anhydride : ウィキペディア英語版
Phthalic anhydride

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Phthalic anhydride is the organic compound with the formula C6H4(CO)2O. It is the anhydride of phthalic acid. Phthalic anhydride is a principal commercial form of phthalic acid. It was the first anhydride of a dicarboxylic acid to be used commercially. This colourless solid is an important industrial chemical, especially for the large-scale production of plasticizers for plastics. In 2000, the world wide production volume was estimated to be about 3 million tonnes per year.〔
==Synthesis and production==
Phthalic anhydride was first reported in 1836 by Auguste Laurent. More contemporary routes include catalytic oxidation of ''ortho''-xylene and naphthalene ("Gibbs phthalic anhydride process"), although use of naphthalene has declined. Starting from o-xylene, the oxidation follows the following stoichiometry:
:C6H4(CH3)2 + 3 O2 → C6H4(CO)2O + 3 H2O
The reaction proceeds with about 70% selectivity. About 10% of maleic anhydride is also produced:
:C6H4(CH3)2 + 7.5 O2 → C4H2O3 +4 H2O + 4 CO2
The reaction is catalyzed by a vanadium pentoxide (V2O5) between 320 - 400 °C. The phthalic anhydride is separated from byproducts by a series of "switch condensers". Phthalic anhydride and maleic anhydride are recovered by distillation. Phthalic anhydride can also be prepared from phthalic acid:〔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. 〕

Large scale industrial production of maleic anhydride is achieved by unification of following unit processes:


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