Recovery of Organic Values from TNT Manufacturing Wastes

Pure 2,4 DNT-3- and -5-SO3Na were prepared from 2,3,4- and 2,4,5-TNT, respectively, and a procedure was developed for their extraction as a mixture from red water. Reactions of the sulfonates were studied, with special emphasis on direct and indirect methods for desulfonating them to 2,4-DNT. Reactions studied also included reduction of the nitro groups, followed by desulfonation to 2,4-DAT heating with sulfur dioxide giving 2-amino-4-nitrotoluene by partial reduction and desulfonation and replacement of the sulfonate group by chlorine, hydroxyl, sulfur, cyano, and various substituted amino groups. Most of these reactions with pure sulfonates were also applied to the corresponding TNT isomers, and in some cases directly to red water. The economic feasibility of 2,4-DAT recovery was considered. Also discussed were recent studies on the recovery of TNM from TNT process gas, and the recovery of TNB from TNT oxidation products.