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The Synthesis of Mono-Amino-Flavones, of Flavone-Azobeta-Naphthol Dyes and of Other Flavone Derivatives Joseph K Marcus

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Naphthalene-based azo dyes: Synthesis, …

2-Naphthol has several different uses including dyes, pigments, fats, oils, insecticides, pharmaceuticals, perfumes, antiseptics, synthesis of fungicides, and antioxidants for rubber.

Nitrosonaphthol dyes and other corresponding analogues were synthesised from 1-Naphthol

. ( is a registered trademark of Hoechst AG; the generic label for the same compounds manufactured by other companies is with a second h. The word is from the Greek for "mineral oil", and salutes the origin of these pigments in petroleum.) Developed and patented in 1911, the naphthol compounds represent the single largest group of azo dyes and pigments. (In fact, about 20% of all synthetic organics available, over 50 in the red category alone, are naphthol pigments.) Originally used as cotton dyes, they were soon laked as pigments and were first used in artists' paints in the 1920's. The most important group for artists is the naphthol AS pigments. The color range is concentrated in the long wavelength end of the spectrum, including warm orange (PO24, PO38), scarlet (, , PR261), many reds (PR2, , PR5, PR7, PR8, , PR17, PR22, , PR150, etc.), carmines (, PR146, the many pigments listed under ), maroon violet (PV13, PV25, PV44), and brown (PBr1).

handprint : synthetic organic pigments

Alizarin, like quinine and many potential novel dyes, was, from around 1850 considered to be related to coal tar compounds. Analysis indicated that the starting point for alizarin might be naphthalene. Indeed, once the aniline colors appeared, synthesis of alizarin from naphthalene was investigated in Germany, France and Britain. However, no useful products appeared. The breakthrough occurred in 1867 at the Gewerbe Institute, a trade college in Berlin. There since 1860, Adolf Baeyer had undertaken research into natural products, and had shown a keen interest in indigo and alizarin. His assistant Carl Graebe established that alizarin was probably a quinone, and went on, with Carl Liebermann to show that it was a derivative of anthracene, and not naphthalene. Alizarin was, as they demonstrated in 1868, a dihydroxyanthraquinone.[21] Synthesis was achieved by bromination of anthraquinone, followed by hydrolysis.

Dyes and Pigments - Journal - Elsevier

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