The preparative scale separation and the identification of constituents of anthraquinonep-derived dye mixtures. Part 3. Products from the combustion of red and violet smoke mixtures

Two colored-smoke grenades, red and violet, were detonated and the particulate and vapour phase portions were collected and analyzed. The original dye mixes were also analyzed for comparison. The chloroform-soluble portion of each dye mix was fractionated by liquid chromatography on silica gel as was the original red dye mix, while the original violet smoke mix was fractionated by differential solubility. Major components were collected in essentially pure fractions while the impurities were concentrated in other fractions. The dye portion of the red smoke mix was substantially unchanged on combusion, with the major component remaining as 1-methylaminoanthraquinone. A significant amount (>5%) of 1-aminoanthraquinone was formed, however. The dye portion of the violet smoke mix was quantitatively converted from 1,4-diamino-2,3-dihydroanthraquinone to 1,4-diaminoanthraquinone upon combustion. The nonvolatile and/or chloroform-insoluble portions consisted mainly of sodium and potassium chlorides, elemental sulfur, and undifferentiated carbonaceous matter. Major constituents of the vapor phases were carbon disulfide, toluene, C₂-benzenes, styrene, chloromethylbenzene and naphthalene. Alipatic and aromatic hydrocarbons, alkylbenzenes, and thiophenes, as well as a number of other compounds were detected in smaller quantities.