The preparative scale separation and the identification of constituents of anthraquinone-derived dye mixtures. Part 2. benzanthrone, dibenzochrysenedione, and 1,4-di-p-toluidinoanthraquinone

Two colored smoke mixes, yellow and green, which contain anthraquinone-derived dyes, were separated for chemical characterization and biological testing. The yellow smoke mix was separated by vacuum sublimation, Soxhiet extraction, and differential solubility. The compounds identified in this mix included the major dye components, benzanthrone and dibenzochrysenedione as well as anthraquinone, a diketone with a molecular weight of 366, a number of high-molecular-weight hydrocarbons, and a nonvolatile residue. The green smoke mix contained 1,4-di-p-toluidinoanthraquinone as the major component along with benzanthrone and dibenzochrysenedione. The bulk of by vacuum sublimation, although some residual toluidino accompanied the benzanththe toluidino derivative was separated from the other two components by chromatography on a basic alumina column. The benzanthrone and dibenzochrysenedione were then separated by vaccum sublimation, although some residual toludino accompanied the benzathrone.