Document Type

Thesis

Date of Award

6-30-1961

Degree Name

Master of Science in Chemical Engineering - (M.S.)

Department

Chemical Engineering

First Advisor

Saul I. Kreps

Second Advisor

James A. Bradley

Third Advisor

Michael Frederick

Abstract

The factors affecting the electrolytic oxidation of p-nitrotoluene to p-nitrobenzoic acid have been studied, and optimum conditions determined for obtaining the best overall yield of 65.7 per cent. These Anode:lead sheetCathode:lead sheetAnolyte:250 cc of 50 per cent sulfuric acid
10 grams of p-nitrotoluene
5 grams of chromic trioxideCatholyte:250 cc of 50 per cent sulfuric acidVoltage:4.5 ± .5 voltsCurrent density:3.0 amperes per square decimeter.Temperatures65 ± 3°CReaction time:fifty per cent of the theoretical time required

It was observed that high potentials and prolonged reaction periods are detrimental to the yield.

A mechanism for the electrolytic oxidation process is suggested, based on experimental observations. It is proposed that the electrolytic oxidation of p-nitrotoluene to p-nitrobenzoic acid in 50 per cent sulfuric acid, is carried out via the chemical oxidation action of chromic trioxide catalyst, in which the current is used to facilitate the selective oxidation of the side-chain methyl group and to retard the destructive oxidation attack on the aromatic ring by the chromic trioxide oxidizing agent.

The electrolytic oxidation process to produce p-nitrobenzoic acid from p-nitrotoluene is not economically feasible at this stage. It is felt that room exists for further development of the process.

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