Use of alpha-di(lower alkoxy) anthraquinones in the synthesis of

Details Use of alpha-di(lower alkoxy) anthraquinones in the synthesis of Use of alpha-di(lower alkoxy) anthraquinones in the synthesis of

1973-11-01

1976-09-28

Demers, Arthur P.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

8 25, 8 39C, 252182, 260365, 260368, 260369, 260370, 260371, 260375, 260351, 260512R, 260383, C07C143665

Patent

active

039831450

ABSTRACT:
Alpha-dihydroxyanthraquinones used as intermediates in the synthesis of many dyestuffs, such as the Alizarin Saphirols (e.g. Color Constitution No. 63000, 63005, 63010, 63011, 63315 and 63610) can be replaced on an equimolar basis by alpha-di(lower alkoxy)anthraquinones. The alpha-di(lower alkoxy) anthraquinones can be converted in a single step, by treatment with oleum, to the corresponding alpha-dihydroxyanthraquinone-beta-disulfonic acids in almost quantitative yield. The corresponding diamine is obtained by dinitrating followed by reduction of the nitro groups. The known intermediate, leuco 1,4,5,8-tetrahydroxyanthraquinone (see C.I. No. 62500) can be obtained either by reduction of the diamine or by reduction of the dinitro compound. In one embodiment, the alpha-di(lower alkoxy)anthraquinone is obtained from dinitroanthraquinone by treatment thereof with methanol and KOH.

REFERENCES:
patent: 1859583 (1932-05-01), Crowell
patent: 1924166 (1933-08-01), Rogers
Barnett, Anthracene and Anthraquinone, D. Van Nostrand Co. N.Y., N.Y., 1921, p. 288.
Kirk-Othmer (I) Encyclopedia of Chemical Technology, Interscience, vol. 2, p. 469, 491, 492.
Kirk-Othmer (II) Encyclopedia of Chemical Technology, vol. 8, p. 473.
Huffmann, Defensive Publication 8670g1094.
Beilstein, vol. 8, p. 454, 459.
Lubs. The Chemistry of Synthetic Dyes and Pigments, A.C.S. Monograph 1955, p. 350- 355, 359.

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