AT51981B - Process for the preparation of an oxidation product of β-aminoanthraquinone. - Google Patents
Process for the preparation of an oxidation product of β-aminoanthraquinone.Info
- Publication number
- AT51981B AT51981B AT51981DA AT51981B AT 51981 B AT51981 B AT 51981B AT 51981D A AT51981D A AT 51981DA AT 51981 B AT51981 B AT 51981B
- Authority
- AT
- Austria
- Prior art keywords
- aminoanthraquinone
- preparation
- oxidation product
- product
- indanthrene
- Prior art date
Links
- XOGPDSATLSAZEK-UHFFFAOYSA-N 2-Aminoanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(N)=CC=C3C(=O)C2=C1 XOGPDSATLSAZEK-UHFFFAOYSA-N 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 3
- 230000003647 oxidation Effects 0.000 title claims description 3
- 238000007254 oxidation reaction Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims 2
- 229910000019 calcium carbonate Inorganic materials 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 description 4
- 235000019239 indanthrene blue RS Nutrition 0.000 description 4
- UHOKSCJSTAHBSO-UHFFFAOYSA-N indanthrone blue Chemical compound C1=CC=C2C(=O)C3=CC=C4NC5=C6C(=O)C7=CC=CC=C7C(=O)C6=CC=C5NC4=C3C(=O)C2=C1 UHOKSCJSTAHBSO-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 235000011941 Tilia x europaea Nutrition 0.000 description 2
- 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 description 2
- 150000004056 anthraquinones Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000005187 foaming Methods 0.000 description 2
- 239000004571 lime Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000010902 straw Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
<Desc/Clms Page number 1>
Verfahren zur Darstellung eines Oxydationsproduktes des ss-Aminoanthrachinons.
Behandelt man ss-Aminoanthrachinon in feiner, wässeriger Verteilung mit Chlorkalk in der Wärme, so erhält man ein neues Produkt, welches ein Gemenge von-Amino- anthrachinon
EMI1.1
EMI1.2
EMI1.3
Wahl der Arbeitsbedingungen.
Beispiel.
10 kg ss-Aminoanthrachinon in Form einer etwa t Obigen Paste werden mit einer filtrierten Lösung von 60 kg Chlorkalk in etwa 300 l Wasser unter Umrühren auf ungefähr 70 bis 900 erhitzt, wobei stürmische Reaktion unter Aufschäumen eintritt.
Sobald das Schäumen aufhört und die orangegelbe Farbe des 3-Aminoanthrachinons in ein helles Strohgelb übergegangen ist, verdünnt man mit etwa 300 1 Wasser, sammelt das Reaktionsprodukt in einer Filterpresse und wäscht hier reichlich mit heissem Wasser.
So gewonnen, stellt das Reaktionsprodukt ein blassgelbes Pulver dar, nicht ohne Zersetzung schmelzbar und unlöslich oder nahezu unlöslich in den gebräuchlichen organischen Lösungsmitteln. Es löst sich dagegen in hochsiedenden organischen Lösungsmitteln, z. B. in siedendem Anilin, Chinolin usw., wobei rasch Blaufärbung der Lösung eintritt. Konzentrierte Schwefelsäure löst das Produkt mit orangegelber Farbe.
Behandelt man das Reaktionsprodukt mit alkalischen Reduktionsmitteln, z. B. mit alkalischen Lösungen von Hydrosulfit, Traubenzucker, Zinnoxydul usw., so wird das ss-Azo- anthrachinon in -Aminoanthrachinon zuruckverwandelt, während das Anthrachinonazhydrin Indanthren bzw. dessen Leukokörper liefert. Diese Umwandlung kann auch auf der Textilfaser vorgenommen werden.
Erwärmt man das Reaktionsprodukt mit Salzsäure oder mit Bromwasserstoffsäure, so bleibt das Azoanthrachinon unverändert, während das Anthrachinonazhydrin in ein Gemenge von Indanthren und Chlorindanthren bzw. Bromindanthren verwandelt wird.
**WARNUNG** Ende DESC Feld kannt Anfang CLMS uberlappen**.
<Desc / Clms Page number 1>
Process for the preparation of an oxidation product of β-aminoanthraquinone.
If β-aminoanthraquinone is treated in fine, aqueous distribution with chlorinated lime in the warmth, a new product is obtained, which is a mixture of aminoanthraquinone
EMI1.1
EMI1.2
EMI1.3
Choice of working conditions.
Example.
10 kg of β-aminoanthraquinone in the form of a paste about the above are heated to about 70 to 900 with a filtered solution of 60 kg of chlorinated lime in about 300 l of water with stirring, a stormy reaction occurring with foaming.
As soon as the foaming stops and the orange-yellow color of the 3-aminoanthraquinone has turned into a light straw yellow, it is diluted with about 300 liters of water, the reaction product is collected in a filter press and washed here with plenty of hot water.
Obtained in this way, the reaction product is a pale yellow powder, cannot be melted without decomposition and is insoluble or almost insoluble in common organic solvents. In contrast, it dissolves in high-boiling organic solvents, e.g. B. in boiling aniline, quinoline, etc., the solution quickly turning blue. Concentrated sulfuric acid dissolves the product with an orange-yellow color.
If the reaction product is treated with alkaline reducing agents, e.g. B. with alkaline solutions of hydrosulfite, dextrose, tin oxide, etc., the ss-azo-anthraquinone is converted back into -aminoanthraquinone, while the anthraquinone azhydrin supplies indanthrene or its leuco body. This conversion can also be carried out on the textile fiber.
If the reaction product is heated with hydrochloric acid or with hydrobromic acid, the azoanthraquinone remains unchanged, while the anthraquinone azhydrin is converted into a mixture of indanthrene and chlorine indanthrene or bromine indanthrene.
** WARNING ** End of DESC field may overlap beginning of CLMS **.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT51981T | 1910-08-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT51981B true AT51981B (en) | 1912-02-10 |
Family
ID=3573057
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT51981D AT51981B (en) | 1910-08-25 | 1910-08-25 | Process for the preparation of an oxidation product of β-aminoanthraquinone. |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT51981B (en) |
-
1910
- 1910-08-25 AT AT51981D patent/AT51981B/en active
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