Acetic Acid → Anthraquinone

Participants

Reaction Steps

It is further known from the Japanese patent publication 49-75563 (Ref: Chem. Abstr. 1975, 43096w) to oxidize o-benzyl-toluene in an aliphatic carboxylic acid, for example acetic acid, in the presence of cobalt salts and bromine compounds, to which manganese salts may also be added as additional catalytic agents. The reaction, carried out at the atmospheric pressure or slightly elevated pressure at temperatures from 70° to 200° C. with air or oxygen-containing gases, yields o-benzoyl-benzoic acid with an anthraquinone content of between 3 and 9% as product. The oxidation in the acetic acid solution is carried out in general with a weight ratio of o-benzyl-toluene to acetic acid of about 1:10. After a reaction time of 4-5.5 hours o-benzoyl-benzoic acid in a yield of about 90-92.5% of theory is recovered, along with about 3-4% of theory of anthraquinone. The purity of the o-benzoyl-benzoic acid is not further discussed. The product is then heated with a minimal amount of concentrated sulfuric acid to about 250°-350° C.; in order to purify the thus-obtained anthraquinone, it is distilled at normal pressure. The degree of purity of this product is also not given. It is further noted that it is advantageous to add to the reaction mixture a solvent which does not mix with water such as benzene, chlorobenzene or dichlorobenzene in order to eliminate the water produced by the reaction as an azeotrope. For example, half of the acetic acid can be replaced according to the publication by chlorobenzene; however, an azeotropic distillation during the oxidation is not achieved by following the example of the Japanese publication.

Provenance & Evidence