Hydrogen Bromide → 4-Nitrobenzoic Acid

Participants

Reaction Steps

Ortho-nitrotoluene (35 g), para-nitrotoluene (35 g), acetic acid (400 g), cobalt (II) acetate (1.0 g), manganese (II) acetate (1.0 g), and 48% hydrobromic acid (1.4 g) were charged into a one liter titanium autoclave. Ortho-nitrotoluene and para-nitrotoluene were present in equal mole ratio, the para-nitrotoluene being added to the reaction as a batch amount. The oxidation was initiated by introducing air into the reactor at an initial temperature of 293° F. and an initial pressure of 250 psig. The oxidation was completed after 70 minutes and it had reached a temperature of 360° F. at a pressure of 350 psig. Ortho-nitrobenzoic acid was found in 49.7 mol % yield and para-nitrobenzoic acid in 73.1 mol % yield (based on LC analysis of the slurry) from the oxidation. Also present in the slurry was ortho-nitrotoluene (43.9 mol %), paranitrotoluene (18.1 mol %), para-nitrobenzaldehyde (4.5 mol %), and p-nitrobenzyl acetate (3.0 mol %).

Provenance & Evidence