In the early days of primuline manufacture, dehydrothiotoluidine was a by-product and was remelted with sulfur to make primuline base. Today, the situation is reversed, and the previously worthless dehydrothiotoluidine has become the main product, while primuline is the byproduct. The dehydrothiotoluidine can be obtained pure by vacuum distillation.101 Unfortunately, it is not possible to conduct the fusion so that only the simple dehydrothiotoluidine is formed; statements to the contrary are incorrect.
Various types of dyes are prepared from dehydrothiotoluidine. The free base or its sulfonic acid is diazotized and coupled with various naph — tholsulfonic acids such as, for example, e acid (l-naphthol-3,8-disul — fonic acid). The resulting dye is characterized by its high purity of color and can be discharged to a pure white. Such red direct dyes are sold under various names, and are usually referred to as dyes of the erika red type. (Erika Z is the combination from dehydrothioxylidine and є acid. l-Naphthol-3,6-disulfonic acid gives a very similar dye.) In addition to the true azo dyes from dehydrothiotoluidine, two other products are made which are important yellow dyes. One of these dyes is the naphthamine yellow NN (also called chloramine yellow) (Kalle), formed from dehydrothiotoluidinesulfonic acid by oxidation with sodium hypochlorite. The other is thiazole yellow or Clayton yellow, which is made by combining the diazo compound of dehydrothiotoluidinesulfonic acid with a second molecule of the same compound to form a diazoamino compound.
It should be noted in passing that alkylation of primuline produces beautiful yellow basic and acid dyes which, however, have no great importance (thioflavine T and S).