Patent GB-191100894-A (GB)
Title: Improvements in the Manufacture and Production of Compounds and Colouring Matters of the Anthracene Series.
Inventor: JOHNSON JAMES YATE
IPC: C09B1/20
Filed: 1911-01-12
Granted: 1911-10-26
Abstract: 894. Johnson, J. Y., [Badische Anilin & Soda Fabrik]. Jan. 12. 1-Arylaminoanthraquinone-2-carboxylic acids are obtained by condensing 1-nitro- or 1-halogenanthraquinone-2-carboxylic acid, or derivatives thereof, with arylamino compounds containing a free ortho-position to the amino group. The following compounds are described in examples: -1-anilinoanthraquinone-2-carboxylic acid, 1- p-toluidoanthraquinone-2-carboxylic acid, 4'- chlor-1-anilinoanthraquinone-2-carboxylic acid, 3': 4<1>-dichlor-1-anilinoanthraquinone-2-carboxylic acid, 1-#-naphthylaminoanthraquinone-2 - carboxylic acid, the condensation products from two molecular parts of 1-chloranthraquinone-2-carboxylic acid, and benzidine, or 4:4'-diaminodiphenylmethane, and the condensation products from 1-chloranthraquinone-2-carboxylic acid and 3-amino - 4 - methyldiphenylketone-2<1>-carboxylic acid or 3-aminodiphenylketone-2<1>-carboxylic acid. Nitro-1-chloranthraquinone-2-carboxylic acid, chlorinated 1-chloranthraquinone-2-carboxylic acid, and 1:4-dichloranthraquinone-2-carboxylic acid, and also aminodiarylketone carboxylic acid, such as 2:4-dimethyl-4'- (or -5<1>-) aminodiphenylketone-2<1>-carboxylic acid, 4 (or 5):4<1>- diaminodiphenylketone-2-carboxylic acid, and naphthyl-4- (or -5-) aminophenylketone-2-carboxylic acid, are specified as parent materials. The acid halogenides of the above - described arylaminoanthraquinone carboxylic acids are obtained, for example, by treatment with phosphorus pentachloride. Treatment of the carboxylic acids with acetic anhydride gives acetyl derivatives. Anthraquinoneacridones, which are vat dyes, are obtained by treating the above-described carboxylic acids with a condensing-agent, such as sulphuric acid or phosgene, or by heating the acid halogenides alone or in an indifferent medium, or with condensing-agents, such as aluminium chloride, or with reducing-agents, such as sodium hydrosulphite, sodium formaldehydesulphoxylate, or zinc dust and ammonia, or by heating the acetyl derivatives alone or in an indifferent medium, or with acid condensing- agents, such as sulphuric acid, zinc chloride, or sodium bisulphate. The production of acridones from the carboxylic acids specified above is described in examples. Where products derived from aminodiarylketonecarboxylic acids are employed, further condensation to form a second anthraquinone residue is effected by carrying on the process until the product is insoluble in alkali. Aminodiarylketonecarboxylic acids.-2:4-Dimethyl-4'- (or 5<1>-) aminodiphenylketone-2-carboxylic acid, 4 (or 5): 4'-diaminodiphenylketone- 2-carboxylic acid, and naphthyl-4- (or -5-) aminodiphenylketone-2-carboxylic acid are obtained by condensing 1-chlorbenzene-3:4-dicarboxylic acid anhydride with m-xylene, chlorbenzene, and naphthalene respectively, and treating the resulting chlor derivatives with ammonia and copper powder. 1-Chloranthraquinone-2-carboxylic acid is obtained by treating 1-chlor-2-methylanthraquinone with chlorine in nitrobenzene, saponifying the #-chlor derivative, and if necessary oxidizing the resulting aldehyde to the carboxylic acid; a nitro and a chlor derivative are obtained by nitrating and chlorinating respectively. 1:4-Dichloranthraquinone-2-carboxylic acid is obtained similarly from 1:4-dichlor-2-methylanthraquinone.