CH147055A - Process for the preparation of a blue, bromine-containing dye of the anthracene series. - Google Patents
Process for the preparation of a blue, bromine-containing dye of the anthracene series.Info
- Publication number
- CH147055A CH147055A CH147055DA CH147055A CH 147055 A CH147055 A CH 147055A CH 147055D A CH147055D A CH 147055DA CH 147055 A CH147055 A CH 147055A
- Authority
- CH
- Switzerland
- Prior art keywords
- blue
- bromine
- preparation
- azine
- sulfuric acid
- Prior art date
Links
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 title claims description 4
- 229910052794 bromium Inorganic materials 0.000 title claims description 4
- 150000001454 anthracenes Chemical class 0.000 title description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 18
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 9
- 239000000975 dye Substances 0.000 claims description 8
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 229920000742 Cotton Polymers 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims 2
- MMWRGWQTAMNAFC-UHFFFAOYSA-N 1,2-dihydropyridine Chemical compound C1NC=CC=C1 MMWRGWQTAMNAFC-UHFFFAOYSA-N 0.000 claims 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 239000004575 stone Substances 0.000 claims 1
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- CHZVHNZRFPALHO-UHFFFAOYSA-N [Br].[Na] Chemical compound [Br].[Na] CHZVHNZRFPALHO-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- FZUJWWOKDIGOKH-UHFFFAOYSA-N sulfuric acid hydrochloride Chemical compound Cl.OS(O)(=O)=O FZUJWWOKDIGOKH-UHFFFAOYSA-N 0.000 description 1
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Coloring (AREA)
Description
Verfahren zur Darstellung eines blauen, bromhaltigen Farbstoffes der Anthracenreihe. Im Hauptpatent ist ein Verfahren zur Darstellung eines blauen, chlorhaltigen Farb stoffes der Anthracenreihe beschrieben, bei dein man auf 1.2.2'.1'-Anthrachinonazin in Gegenwart von mässig wasserhaltiger Schwe felsäure Ohlorwasserstoffsäure einwirken lässt.
Es wurde nun gefunden, dass man ein wertvolles; blaues; bromhaltiges Derivat des N-Dihydi-o-1.2.2'.1'-anthrachinonazins sehr leicht erhalten kann, wenn man auf 1. 2. 2'. 1'- Anthrachinonazin in Gegenwart von mässig wasserhaltiger Schwefelsäure Bromwasserstoff säure einwirken lässt. Besonders vorteilhaft ist die Anwendung einer 50-75 o/oigen Schwefelsäure.
An Stelle der Broinwasser- stoffsäure kann man mit Vorteil auch Ver bindungen der Bromwasserstoffsäure, die unter der Einwirkung der verwendeten Schwefel säure Bromwasserstoffsäure abspalten, be nutzen. In besonders reiner Form erhält man das Bromierungsprodukt des N-Dihydroanthra- chinonazins, wenn man von reinem Azin, wie man es zum Beispiel durch Behandlung des tecbnisohen N-Dihydroantbracbinonazins in schwefelsaurer Lösung mit Braunstein er hält, ausgeht.
Man kann in diesem Falle die Herstellung des reinen 1 . 2 . 92' .1'-Anthra- chinonazins und die Überführung in das halo- genierte N-Dihydro-1. 2. 2' . 1'-anthrachinon- azin in einer Operation ausführen.
Der Farbstoff ist ein etwa ein Bromatom enthaltendes N-Dihydro-1 . 2 . 2' . 1'-anthra- ehinonazin und färbt Baumwolle aus blauer Küpe in blauen Tönen. <I>Beispiel:</I> 10 Teile N-Dihydro-1 . 2 . 2' . 1'-anthra- chinonazin von der Reinheit, wie sie der Farbstoff Indantbrenblau RS des Handels (vergl. G. Schultz, Farbstofftabellen, 1923, Nr. 837) besitzt, werden in 100 Teilen Schwefelsäure von 66 B6 gelöst.
Hierauf lässt man langsam 5 Teile Wasser zufliessen und sodann eine Aufschlämmung von 6 Tei- len Braunstein in 30 Teilen Schwefelsäure von 90 % Schwefelsäuregehalt, .darauf erhitzt man die Reaktionsmasse etwa 6 Stunden lang auf 65-70 o C. Man lässt auf etwa 30 o C abkühlen und lässt 80 Teile rauchende Schwefelsäure von 23 0/\o SOs-Gehalt zulaufen, um das zum Teil ausgeschiedene Azin in Lösung zu bringen. Sodann verdünnt man mit 120 Teilen Wasser, erwärmt auf 90 bis 100 o C und lässt bei einer Temperatur ober halb 95 o C 150 Teile einer 10 %igen wäs serigen Lösung von Bromnatrium zulaufen.
Man rührt noch etwa 2 Stunden lang bis zur Beendigung der Umsetzung bei 95 bis 100 o C, verdünnt dann mit Wasser und arbeitet in der üblichen Weise auf.
Process for the preparation of a blue, bromine-containing dye of the anthracene series. The main patent describes a process for the preparation of a blue, chlorine-containing dye of the anthracene series, in which one can act on 1.2.2'.1'-anthraquinone azine in the presence of moderately hydrous sulfuric acid hydrochloric acid.
It has now been found that one can find a valuable one; blue; Bromine-containing derivative of N-Dihydi-o-1.2.2'.1'-anthraquinone azines can be obtained very easily if one goes to 1. 2. 2 '. 1'-Anthraquinone azine in the presence of moderately hydrous sulfuric acid allows hydrobromic acid to act. The use of a 50-75% sulfuric acid is particularly advantageous.
Instead of hydrobromic acid, it is also possible to use compounds of hydrobromic acid which split off hydrobromic acid under the action of the sulfuric acid used. The bromination product of N-dihydroanthraquinone azine is obtained in a particularly pure form if one starts from pure azine, as is obtained, for example, by treating tecbnisohen N-dihydroanthraquinone azine in sulfuric acid solution with manganese dioxide.
In this case, the production of the pure 1. 2. 92 '.1'-Anthrachinonazins and the conversion into the halogenated N-dihydro-1. 2. 2 '. Perform 1'-anthraquinone azine in one operation.
The dye is an N-dihydro-1 containing about one bromine atom. 2. 2 '. 1'-anthra- ehinonazine and dyes cotton from a blue vat in blue tones. <I> Example: </I> 10 parts of N-dihydro-1. 2. 2 '. 1'-anthraquinonazine of the purity as possessed by the commercial dye indantbrene blue RS (cf. G. Schultz, dye tables, 1923, no. 837) is dissolved in 100 parts of sulfuric acid of 66 B6.
Then 5 parts of water are allowed to flow in slowly and then a suspension of 6 parts of manganese dioxide in 30 parts of sulfuric acid with 90% sulfuric acid content is added. The reaction mass is then heated to 65-70 ° C. for about 6 hours C to cool and let 80 parts of fuming sulfuric acid with 23 0 / \ o SOs content run in to bring the partially separated azine into solution. It is then diluted with 120 parts of water, heated to 90 to 100 ° C. and 150 parts of a 10% aqueous solution of sodium bromine are run in at a temperature above 95 ° C.
The mixture is stirred for about 2 hours until the reaction has ended at 95 to 100 ° C., then diluted with water and worked up in the customary manner.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE147055X | 1928-07-25 | ||
| CH143991T | 1929-06-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH147055A true CH147055A (en) | 1931-05-15 |
Family
ID=25714391
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH147055D CH147055A (en) | 1928-07-25 | 1929-06-17 | Process for the preparation of a blue, bromine-containing dye of the anthracene series. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH147055A (en) |
-
1929
- 1929-06-17 CH CH147055D patent/CH147055A/en unknown
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