GB347722A - Improvements in the manufacture and production of halogenanthraquinone-ª‰íúª‡(n)-benzacridones - Google Patents

Abstract

Halogenated anthraquinone-b .a (N)-benzacridones are prepared by treating anthraquinone-b .a (N)-benzacridone or derivatives thereof other than iodo derivatives, with chlorine or bromine or agents supplying chlorine or bromine in inorganic acid media and preferably in the presence of halogen transferrers. Inorganic acid media comprise sulphuric acid, oleum, chlorsulphonic acid or metal chloride melts and where the starting material has been prepared by condensation with such an acid medium, halogenation may be effected without isolation of the product. In some cases chlorsulphonic acid may act as halogenating agent itself. Suitable catalysts are iron, iron chloride, mercury, antimony, iodine, and sulphur. The products dye various shades of red which differ both in shade and fastness from those halogenated derivatives prepared by halogenation in organic diluents (see Specifications 7923/10 and 22780/10, [both in Class 2 (iii), Dyes &c.]). Examples describe the chlorination of anthraquinone-2.1-benzacridone and the following derivatives thereof: Bz3-methyl and Bz3.5-dimethyl- (prepared by condensing 1-chloranthraquinone-2-carboxylic acid with p-toluidine and m-xylidine respectively, followed by ring-closure); Bz3-alkoxy- (prepared by condensing 1-chloranthraquinone-2-carboxylic acid with p-alkoxyanilines and ring-closure); Bz3-chloro-, Bz5-chloro-, Bz2- and Bz4-chloro- (prepared by condensing 1-chloranthraquinone-2-carboxylic acid with p-chloraniline, o-chloraniline, and m-chloraniline respectively and ring-closure of the products, followed in the last case by separation of the two isomers formed, either by fractional crystallization or by way of their oxonium salts); Bz3.5-dichloro-(example 1 of Specification 346,676); Bz2.3-di-chloro-, Bz2.4-dichloro- (prepared by condensing 1-chloranthraquinone-2-carboxylic acid with 3.4-dichloraniline and 3.5-dichloraniline respectively, and ring-closure); 4-Bz3.5-trichloro- (prepared by chlorinating the acridone in trichlorobenzene); Bz2.3.4-trichloro- (prepared by condensing 1-chloranthraquinone-2-carboxylic acid with 3.4.5-trichloraniline and ring-closure); 4-nitro-Bz3.5-di-chloro- (prepared by nitrating Bz2.4-dichloranilidoanthraquinone-2-carboxylic acid in nitrobenzene followed by ring-closure); Bz3-nitro (prepared by condensing 1-chloranthraquinone-2-carboxylic acid with p-nitraniline and ring-closure); the bromination of some of these compounds is also described and also the chlorination and bromination of anthraquinone-2.1 : 6.5-dibenzacridone. The products derived from Bz3.5-dihalogen-derivatives are stated to be particularly valuable. Specification 338,216, [Class 2 (iii), Dyes &c.], also is referred to.