Acetic Acid → Azobenzene

Participants

Reaction Steps

A crude peracetic acid solution was prepared by mixing 17.3 g glacial acetic acid (0.29 mole), 7.2 g of a hydrogen peroxide solution having 68% by weight of H2O2 (0.145 mole of H2O2), and 0.7 g concentrated sulphuric acid, and reacting the mixture for several hours at ambient temperature. A solution was obtained which contained 0.10 mole peracetic acid and 0.033 mole uncoverted hydrogen peroxide, and which was introduced into 200 ml of methanol at 0° C. Within the space of half an hour 34.8 g acetone (0.6 mole), 12.2 g of an ammonia solution having 28% by weight NH3 (0.2 mole), and 18.6 g aniline (0.2 mole) were added, after which the mixture was determined by gas phase chromatography to contain 4.6 g of acetone phenylhydrazone (0.031 mole, which was 31% of the theoretical yield compared to the peracid), 1 g of acetone azine (0.009 mole, which was 9% of the theoretical yield), and 0.025 mole of azobenzene.

Provenance & Evidence