DE359138C - Process for the production of nitrogen-containing condensation products of the anthraquinone series - Google Patents

Description

Process for the production of nitrogen-containing condensation products the anthraquinone series.

Addendum to Patent 343064 In the patent 343o64 is a method for Production of condensation products described, which consists in that 'i-annino-2-methylanthraquinone with .aromatic nitro compounds in the presence of alkalis with or without additives primary aromatic amino compounds is heated to a higher temperature.

It has now been found that this reaction does not affect i-amino-2-methylanthraquinone limited, but more generally to the amino derivatives of 2-methylanthra: quinone as well as 2-methylanthraquinone itself can be applied. The new condensation products have a constitution analogous to that described in patent 343o64 and are as azounethine compounds of anthraquinone-2-aldehyde substituted by amino groups (or of the anthraquinone-2-aldehyde itself) to be understood, since they are treated with Acids provide the corresponding aldehydes.

The process closely follows that described in the '343o64 patent and is illustrated by the following examples.

Example i.

A solution. of 10 kg of 2-methylanthraquinone in 4o kg of nitrobenzene with the addition of 10 kg of aniline and 2 kg of potassium carbonate kept boiling for 6 hours. The new condensation product separates from the hot-filtered solution in the case of demn Colds and is formed by crystallization from toluene oil in shiny yellowish crystals obtained from melting point 185 to 186 °. The condensation product dissolves in concentrated Sulfuric acid with a yellow color that does not change with the addition of paraformaldehyde is and delivers an intensely olive colored vat with hydrosulphite and lye.

Example e.

10 kg of 4-p-tolwido-i-attnino-2 = methyl'anthraquinone (patent 131873, example i), 35 kg of nitrobenzene, 5 kg of aniline are heated to about 225 ° (outside temperature) for 5 hours with the addition of 5 kg of molten potassium acetate . From the hot, filtered solution, when it cools, the new condensation product separates out in shiny dark crystals. The compound is soluble in high-boiling organic solvents with a green color. The melting point is around 229 °. The color of the solution in concentrated sulfuric acid is yellow-olive and turns black-violet with the addition of paraformaldehyde. Example3. A solution of 3-amino-2-methylanthräehinon - (P: ätei2t "28z oio; Example 2) in 40 kg of nitrobenzene is refluxed for 5 hours after adding 6 kg of aniline and 5 kg of potassium carbonate The hot, filtered solution separates the new condensation product on cooling. The melting point of the compound purified by redissolving from nitrate of benzene is over 300 °. The color of the solution in concentrated sulfuric acid is brownish yellow and becomes redder with the addition of paraformaldehyde. With hydrosulphite and lye an olive colored cape is obtained.

Example 14. 10 kg of z.5-Diamina-2-methylanthrachinoii (Patent 13i873, Example 3), 40 kg of nitrobenzene, 5 kg of aniline are heated to about 225 ' (outside temperature) for 5 hours with the addition of 4 kg of potassium carbonate. The intensely blue-red solution, filtered hot, is diluted with alcohol; after cooling, the deposited condensation product is filtered off. The dark purple powder obtained in this way dissolves in concentrated sulfuric acid with an olive color, which turns blue-green with the addition of paraformaldehyde. Cotton is dyed in violet-red tones from the olive-dyed vat.

Claims (1)

PATENT CLAIM: Modification of the process protected by patent 343o64, consisting in that instead of z-aminoL2-methylanthraquinone .other Aan.inoderivate of 2-methylanthraquinone and 2-methylanthraquinone itself with aromatic nitro compounds with or without the addition of primary aromatic amino compounds in the presence of alkalis heated to a higher temperature.