Document Type


Date of Award


Degree Name

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


Chemical Engineering

First Advisor

George C. Keeffe

Second Advisor

Saul I. Kreps

Third Advisor

James A. Bradley


In the oxidation of 2-nitro-p-xylene (I) using alkaline potassium permanganate, the only product isolated was 2-nitro-terephthalic acid (II). Approximately half of the starting material was oxidized. The other half remained as unreacted starting material.

The chromium trioxide oxidation of 2-nitro-p-xylene (I) in glacial acetic acid, using sulfuric acid as a catalyst, yielded only 3-nitro-p-toluic acid (III).

The chromium trioxide oxidations, of 2-N-acetylamino-p-xylens (IV) with and without sulfuric acid catalyst, yielded no oxidation products which could be identified. About half of the starting material was recovered in each case.

In a low temperature alkaline potassium permanganate oxidation of 2-N-acetyIamino-p-xylene a small amount of 2-N-acetylamino-p-toluic acid (V) and unreacted 2-N-acetylamino-p-xylene were isolated.

In the alkaline potassium permanganate oxidation of 2-N-acetylamino-p-xylens (IV) carried out at reflux small amounts of 2-N-acetylamino-p-toluic acid (V) and 3-N-acetylamino-p-toluic acid (VI) were isolated. The greatest amount of material recovered from the reaction was unreacted 2-N-acetylamino-p-xylene (IV).

The expected products from the partial oxidation of monosubstituted p-xylenee are found in the literature, but none of them have been previously prepared by partial oxidation of the substituted p-xylene. Instead they were prepared by the hydrolysis of the corresponding nitrile.

The sigma values of the Hammett Equation (I), which have been used successfully in predicting aromatic substitution reactions of polysubstituted aromatic compounds, were used and found to correlate the experimental results of this work.

The partial oxidation of 2-nitro-p-xylene yielded 3- nitro-p-toluic acid. This agreed with the correlation.

In the partial oxidation of 2-N-acetylamino-p-xylene, the results were poor. This result could also be explained in terms of the correlation.



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