US1790109A

US1790109A - Production of anthraquinone-azines

Info

Publication number: US1790109A
Application number: US229258A
Authority: US
Inventors: Nawiasky Paul; Eifflaender Ludwig
Original assignee: General Aniline Works Inc
Current assignee: General Aniline Works Inc
Priority date: 1926-10-08
Filing date: 1927-10-27
Publication date: 1931-01-27
Anticipated expiration: 1948-01-27

Description

Patented Jan. 27,1931 7 UNITED STATES PAUL NAWIASKY AND LUDWIG EIFFLAENDER, E:LUDWIGSHAFElN-QN-THE-RHINE, GERMANY, AssIGNoRs'ro GENERAL ANILINE.WORIS,INQ., QENEW@YOBK, N. Y., A

, CORPORATION OF DELAWARE PRODUCTION or nnrnnnonrnonnmz rivnsg if 1 i No Drawing. Application filed October 27, 1927, ser aijiq ffaasas; arm in German emb "811926. I

The present invention relates to improvements in the production of N-dihydro- 1.2.1.2-anthraquinone-azines.

It is known that the valuable blue dyestufi 5 N -dihydro-1.2.1.2'-anthraquinone-azine can be obtained by the action of fused caustic alkali on 2-aminoanthraquinone, with or without the addition of oxidizing agents,- the melt being poured into water and oxidized with air. In order to improve the yield, it has also been proposed to add to the melt salts of low fatty acids, such for example aspota ssium formate, potassium acetate, and the like,

in'the presence, if required, of an inert diluent, or to add alcoholates or phenolates, such as sodium butylate, sodium phenolate, and

the like.

We have now found that still better yields 7 f th id dyestuff or of its derivatives wh starting from substituted' 2-amino-anthraquinone, may be obtained if salts of low fatty acids, namely of formic, acetic or propionic acid are added to the caustic alkali melt in conjunction with organic compounds containing at least 3 carbon atoms in their molecule and also containing a metal attached to an oxygen atom. As examples of such organic compounds may be mentioned salts.

of fatty acids with at least 4 carbon atoms, in particular soaps, further metal alcoholates or phenolates. For example, sodium acetate may be added'in conjunction with 7 5 arts of dehydrated sodium acetate are intro uced into a melt of 2000 parts of caustiopotash-s o'da 'ata temperatureof 250C 7 parts of sodium""glycerate 3 being then} added; andthemi'xture stirred untilunifor-m distribntionfhas taken place. The 'mixtureis next cooleddownto a temperature of 210 (1. and :500. parts ;of fi-aminoanthraquinone are introduced in such a way that the temper-' aturei-doesnot rise ab0ve'230 C; The wholemixture is maintained at a temperature of 225 C. until no further'increase in the pro thraquinone can no longer be-detected. The

meltis then treated in the usual manner.

Examp 2 15. parts of dehydrated sodium acetateare stirred into 200 parts of a mixture, in molecular proportions, of caustic potash and soda at a temperature of about 200 (1., 20 parts of soap being then added. Thereupon parts of ,B-aniinoanthraquinone are introduced, and the mixture is stirred at a temperature a of from 200 to 210 C. until the production tained by evaporating 'su 'te cellulose waste liquor, salts of diisopropylnaphthalene sulfonic acid or bile acid, Turkey-red oil, acids tar, and the like.

Example 3 C. and 500 parts of ,8-aminoanthraquinone are introduced in such a way that the temperature does not rise above 230 C. The whole mixture is maintained at a temperature of 225 C. until the production of 'dyestulf ceases to increase and B-aminoanthraquinone can no longer be detected. The melt is then treated in the usual way.

obtained by the sulfonation of brown-coal What We claim is: 1; The process of producing N-dihydro- 1.2.12' anthraquinone azine which comtion With an alkali metafcompoim'dbfafi al coholxcontainingatleast thigee carboniatomsa 31 The process of producing N-dihydi'oprises subjecting Q-amino-anthraquinohe to the action of a, caustic potash-sodamelt in the presence ofsodilimaacetateain conjunction with an alkali metal butyrate.

2. The process of producing N-Hili'j'rdi'b- 1.211";2?.-anthraquinone-azinesu which prises subjecting a 2-amino+anthnaquinonetoia the action of a caustic alkali melt in the presence of a salt of a 10w fatty ,acidin COI DjI IILC:

1.21.2fanthraquinone-azines which; comeprises subjecting;a12gamino+anthraquinone t'm the) action; 015a caustic; potashesoda; melttin: the: PIQSQIICQLOTE a: salt of :txlowfatty acidg'i'm conjunction WlthiaD alkali metal compoundi of: 3111311001101 coiitainingatleast three carbon Intestlinony whereofwwe:havehereuntozset;

our "hands;

PAUL NAWIASKY. a a EIFELAENDERa,