Selective Reduction of Dinitrotoluene Isomers by Ascorbate Ion. Relative Rates in Homogeneous Solution.

摘要

Investigations were conducted with the objective to reduce waste products and the associated water pollution problems arising from the manufacture of trinitrotoluene (TNT). The approach was to remove undesired dinitrotoluene (DNT) isomers by selective reduction with inexpensive carbohydrates,such that the resulting mixture,upon subsequent nitration,would yield specification grade TNT. Using ascorbic acid as a model compound,kinetic studies were performed on five DNT isomers in aqueous acetonitrile at different pH's. Appreciable differences in the rates of reduction of the five DNT isomers were obtained indicating that the undesired DNT isomers could be preferentially removed from a crude mixture of DNT. Furthermore,experiments were performed to simulate process conditions. When actual mixtures of DNT isomers were stirred in a basic ascorbic acid solution,the undesired DNT isomers were considerably reduced,whereas the desired 2,4-and 2,6-DNT's were virtually unaffected. (Author)