DE185548A - - Google Patents

Description

oinaisHicil "

wwi bet cPai & vi \ 'a \ n Ib.

ΐνν \ α

IMPERIAL

PATENT OFFICE.

PATENT LETTERING

_: .- M 185548 CLASS 22b. GROUP

Patented in the German Empire on June 26, 1906.

Treats a-aminoanthraquinone and

its derivatives with ketones of the type CH ₃ - CO - R (where R is any radical such as CH ₃ , C ₆ H ₅ ,. CH _2. C 0OH etc.) in the presence of alkalis, new condensation products are formed, some of which are called Dyes, are partly important as starting materials for dyes.

The reaction probably goes in the following sense:

"CO

The following examples illustrate the process.

Example 1.

50 kg of α-aminoanthraquinone are finely divided with 1200 kg of water, 100 kg of acetone and 100 kg of sodium hydroxide solution of 34 ^° Be. Boiled on the reflux condenser until no more unchanged amine can be detected. The crystalline reaction product is filtered off with suction, washed and dried. It crystallizes from pyridine in yellowish prisms, which are concentrated in. Dissolve sulfuric acid yellow with greenish fluorescence. The analysis provides numbers which indicate a condensation product of ι molecule of aminoanthraquinone and 1 molecule of acetone minus 2 molecules of water.

45

+ 2 H ₁ 0.

Calculated for
C _n H _n ON:

C = 83.26 percent
H = 4.49

5'7 ² found:

83.39 percent 4.68 5.79

55

60

Example 2.

10 kg of finely ground 1 · 4-diaminoanthraquinone are mixed with 500 l of water and 20 kg of sodium hydroxide solution of 34 ^° Be. and 50 kg of acetone heated ^{to 125 0} in an autoclave for 10 hours. It is filtered off and the residue is dissolved in warm hydrochloric acid, whereupon the hydrochloride of the base crystallizes out. It stains cotton stained with tannin crushed tartar yellow-brown.

Claims (1)

Example 3. 15 kg ι · 5 - diaminoanthraquinone disulfosaures Potash is dissolved in 500 l of water and, after the addition of 20 kg of sodium hydroxide solution and 20 kg of acetone, for 3 hours in the reflux condenser cooked. Upon acidification, the condensation product precipitates in brown flakes. It stains unheated wool brown. Example 4. 5 kg ι - aminoanthraquinone -.5 - sulfonic acid sodium are with 5 kg sodium hydroxide solution, 250 l Water and 10 kg methyl ethyl ketone boiled under reflux for 2 hours. The by addition Crystals separating out of acid are collected on a filter. If the methyl ethyl ketone is replaced by acetophenone, an analogous one is obtained Product. · Example 5. 5 kg α - aminoanthraquinone are heated for 1 hour at 140 ⁰ with 50 kg of ethyl acetoacetate and 5 kg of sodium methylate. The condensation product separates out when it cools down. It is filtered off with suction, washed with alcohol and water and, after drying, recrystallized from nitrobenzene. The body forms greenish-yellow leaflets that turn yellow in diluted soda lye solve. The body described is the carboxylic acid of the basic substance listed in Example 1 and was created by saponification of the ester by the alkali released during the condensation. In the case of sublimation the product goes into that described in Example 1 with elimination of carbonic acid Body over. 25th
K 0 η de "nsat io η s ρ r 0 du kt aus solution
in
Pyridine Solution in
more focused
sulfuric acid Solution in
more focused
sulfuric acid
, and
formaldehyde
solution 30th
a - aminoanthraquinone + acetone colorless yellow, with yellow
fluorescence yellow 35 ι · 4 - diaminoanthraquinone + acetone yellow yellow, with green
fluorescence Red ι · 5 - diaminoanthraquinone disulfonic acid
+ Acetone Brown yellow, with turquoise
blue fluorescence green ι - Aminoanthraquinone.- 5 - sulfonic acid
+ Methyl ethyl ketone orange yellow, with green
fluorescence • yellow .. ι - aminoanthraquinone - 5 - sulfonic acid
+ Acetophenone colorless yellow,
without fluorescence yellow α - aminoanthraquinone + acetoacetic ester yellow yellow,
without fluorescence orange Pate nt-A ν SPRU c η:
"Process for the preparation of anthracene derivatives, consisting in that one a-Aminoanthraquinones in the presence of alkalis with ketones from. Type CH ₃ - CO-R treated.