Przemysl Chemiczny, Vol.82, No.5, 342-346, 2003
Studies on catalytic liquid-phase oxidation of anthracene
With (a) aq. 30% H2O2 and (b) urea-H2O2 complex as oxidant, anthracene was oxidized in (a) 1,4-dioxane or (4:1 v/ v) acetophenone-AcOH and (b) Ac2O as solvent, over (a) VO(acac)(2) and (b) VO(acac)(2) or FeSO4 or phosphomolybdic acid as catalyst, at (a) 25degreesC-b.p. and (b) 0-40degreesC in (a) 2-4 and (b) 3-10 h to anthraquinone in (a) 76-92 and (b) 0-76%, resp. When mixed 1:1 (w/w) with anthraquinone, anthracene was oxidized similar to 100% in 1 h at 55degreesC. Over VO(acac)(2) or silicotungstic acid as catalyst, H2O2 oxidized anthracene (3:1 by mols, 70degreesC, 4 h) in 67-70% to 9,10-anthraquinone which was reduced with Zn to 9,10-dihydroxyanthracene. This was esterified in situ to 9,10-diacetoxyanthracene. Reduction of anthraquinone with Zn in Ac2O as solvent and C5H5N as catalyst also gave 9,10-diacetoxyanthracene, m.p. 272degreesC. More economic was the two-step route: (i) anthracene was oxidized 60-80% with O-2 at 20-60degreesC over polyaniline.HCl-or poly-o-toluidine.HCl- Co(Ac)(2)as catalyst, (H) the unconverted reactant was oxidized up with H2O2.