Collect. Czech. Chem. Commun. 1983, 48, 112-122

Isolation and identification of by-products of gas phase catalytic oxidation of anthracene to 9,10-anthraquinone

Ivan Chvátala, Jan Vymětala, Jaroslav Pechaa, Vilím Šimánekb, Ladislav Dolejšc, Josef Bartoňa and Josef Fryčkaa

a Research Institute for Coal Tar Chemistry, Urx Works, 757 27 Valašské Meziříčí
b Chemical Institute, Faculty of Medicine, Palacký University, 775 15 Olomouc
c Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6


A total of 29 associate components were identified in technical 9,10-anthraquinone. The product contained all the prominent impurities present in the starting anthracene except for 9,10-dihydroanthracene and fluorene. 9-(9'-Anthryl)-carbazole and Diels-Alder type adducts of anthracene with maleic anhydride and with maleinimide were also detected. The isolated and identified by-products of oxidation of anthracene were 1,4-anthraquinone, 4,4'-dioxo-1,1'-bianthrylidene, 4,10'-dioxo-1,9'-bianthrylidene, 1-(4'-oxy-1'-naphthylidene)-4-oxyanthracene, 2,3-naphthalenedicarboxylic acid and anhydride, and 5,7,12,14-tetrahydro-5,14;7,12-di(o-benzeno)pentacene-6,13-dione. Of the compounds formed by oxidation of the anthracene impurities, isolated and identified were dibenzo[b,d]pyrone, xanthone, 1,8-naphthalenedicarboxylic acid anhydride,9-fluorenone, and naphthol[2,3-b]thiophene-4,9-dione. As products of a deeper oxidation of the starting compounds, phthalic anhydride, maleic anhydride, maleinimide, phthalic acid, and maleic acid were found. Four additional components whose structure could not be determined were also isolated. The pathway of the anthracene oxidation is suggested.