DE216980C - - Google Patents

Description

IMPERIAL

PATENT OFFICE

In the patent specification 210019 it was shown that by condensation of one molecule of succinic acid with two molecules of an aminoanthraquinone valuable new products are created. In the patent specification 212436 (add for patent 210019) it was also shown that succinic acid can be used with equal success by their anhydride or by those of their derivatives, in which the hydroxyl the carboxyl group is replaced by easily reacting or substitutable atoms or radicals is.

It has now been found that succinic acid and its just identified Derivatives with similar success generally by other dibasic acids of the aliphatic or aromatic series, as well as their anhydrides and derivatives.

In some cases, the reaction is carried out by adding suitable condensing agents, such as z. B. phosphorus chloride, zinc chloride, boric acid, etc. influenced in an advantageous manner.

The following examples may serve as an explanation:

Example 1.

10 kg of α-aminoanthraquinone are made up with 2.4 kg of malonic acid and 50 kg of nitrobenzene 100 ° warmed .; To this, 5 kg of phosphorus pentachloride are slowly added and held after the entry about 1 hour at this temperature. After cooling down, the excreted The reaction product is filtered off and washed with nitrobenzene and alcohol. That The product obtained in this way is a yellow one, which is very sparingly soluble in organic solvents Powder.

Example 2.

33 kg of d-aminoanthraquinone and 11 kg of adipic acid are dissolved in 150 kg of nitrobenzene and heated to boiling for 6 hours. On that allowed to cool to 90 to 100 ° and carries 15 kg of phosphorus pentachloride at this temperature a. After stirring for a further hour, the mixture is allowed to cool and the precipitated material is filtered off with suction Product. It forms a yellow crystalline powder.

Example 3.

15.5 kg of 1x4 diaminoanthraquinone heated to ϊοό ° with 10 kg of adipic acid in 100 kg of nitrobenzene and 8 kg of phosphorus pentachloride added in small portions. The reaction has ended after about 2 hours, the mixture is allowed to cool, filtered off with suction and washed with Alcohol after. A red-brown powder is obtained in this way.

Example 4.

I · 4 - aminooxyanthraquinone

heated with 6.2 kg of adipic acid in 100 kg of nitrobenzene to 100 to 100 ° and stirring 6 kg of phosphorus pentachloride entered. To

Let it cool down for 2 to 3 hours, it sucks Condensation product and washes it with alcohol. It represents a reddish brown powder represent.

Example 5.

10 kg ι · 5 - nitraminoanthraquinone in 60 kg nitrobenzene with 5 kg maleic acid or its anhydride and 5 kg phosphorpene tachloride Heated to 100 to 100 ° for 2 hours. The product excreted after cooling is suctioned off and washed with alcohol. It is a yellow powder.

Example 6.

20 kg of α-aminoanthraquinones are heated with

12 kg of methylenecitric acid chloride in 100 kg Xylene 2 to 3 hours at 100 to 120 ° and isolates the product obtained as above

ao given. It is a yellow powder.

Example 7.

22 kg of ct-aminoanthraquinone are in 100 kg Nitrobenzene together with 8 kg of phthalic anhydride and 7 kg of phosphorus pentachloride Stirring heated to 100 ° for 2 to 3 hours. The isolated product is a yellow powder.

Example 8.

10 kg of terephthalic acid are mixed with 25 kg of phosphorus pentachloride and 150 kg of nitrobenzene heated on the water bath for one hour, then 27 kg of α-aminoanthraquinone were added with stirring and continued for several hours at the same time Temperature held. It is now allowed to cool and what has separated out as a yellow powder is sucked off Product.

The following table describes the characteristics of some of the products:

Product from
«5 colour
the solution
in
more focused
sulfuric acid colour
the
Vat coloring
on
cotton α-aminoanthraquinone + malonic acid yellow Red yellow 3 °.
α-aminoanthraquinone + adipic acid yellow yellow Red yellow ß-aminoanthraquinone + adipic acid yellow yellow Red yellow . ι · 4-diaminoanthraquinone + adipic acid weak
colored Red red-brown ι · 4-aminochloranthraquinone + adipic acid
40 yellow Red yellow ι · 4-Aminooxyanthraquinone + adipic acid ' Brown brownish
Red orange brownish red ι · 4-nitraminoanthraquinone + adipic acid. :
45 weak
colored Red violet ι ^ -Aniinochloranthraquinone ■ + · Adipic acid yellow Red yellow α-aminoanthraquinone + sebacic acid
50 yellow Red yellow a-aminoanthraquinone -} - diglycolic acid ' yellow Red yellow 55 α-aminoanthraquinone + malic acid yellow Red yellow : α-aminoanthraquinone + tartaric acid yellow Red yellow 60 α-Aminoanthraquinone + methylene citron sulphide chloride yellow Red yellow

Product from
5 colour
the solution
in
more focused
sulfuric acid ' Colour
the
Vat coloring
on
cotton α-Aminoanthraquinone -j- maleic acid yellow discolored yellow ίο ι. 5-nitraminoanthraquinone ■ + ■ maleic acid yellow Brown Red α-aminoanthraquinone + camphoric acid Red brownish red olive ¹ Sa-aminoanthraquinone + phthalic anhydride yellow Red yellow-orange α-Aminoanthraquinone ■ + ■ terephthalic acid yellow dirty
violet yellow

Claims (1)

Patent claim: Further development of the patent 210019 or its addition 212436 protected process for the preparation of nitrogen-containing anthraquinone derivatives, consisting in the fact that instead of the there used succinic acid or its anhydride or its in the carboxyl group here other dibasic acids or their derivatives substituted by a readily reacting atom or radical corresponding derivatives condensed with aminoanthraquinones or their derivatives.