The preparative scale separation and the identification of constituents of anthraquinone-derived dye mixtures. Part 1. 1-methylaminoanthraquinone, 1,4-diamino-2,3-dihydroanthraquinone and 1,4-diaminoanthraquinone

Two colored smoke mixes, red and violet, were separated to isolate the major dye components from their impurities for both chemical characterization and biological testing. The red smoke mix was separated into three fractions by vacuum sublimation. The major dye component, 1-methylaminoanthraquinone (MAA) was isolated in fraction 2 at about 98% purity. Fraction 1 contained a number of impurities, including aminoanthraquinone, azobenzene, azoxybenzene, aminobiphenyl, and phenyldiazobenzene. The third fraction was a non-volatile black powder containing only C, H, and O with hydroxyl groups. The violet smoke mix was separated into four fractions by using differential solubilities, taking advantage of the solubility differences of the two main components, MAA and l,4-diamino-2,3-dihydroanthraquinone (DDA) in chloroform. Fraction 1 contained primarily MAA, with trace amounts of anthraquinone, DDA, aminonaphthalene, aminoanthraquinone, phenyldiazobenzene and 1,4-diaminoanthraquinone (DAA). Fraction 2 contained mostly DDA, along with some DAA and small amounts of MAA, aminoanthraquinone, aminonaphthalene and anthraquinone. Fraction 3 contained both DDA and DAA with a trace of aminonaphthalene. Fraction 4 was a gray chloroform-insoluble residue.