CH169928A - Process for the preparation of an oxynaphthetriazole. - Google Patents
Process for the preparation of an oxynaphthetriazole.Info
- Publication number
- CH169928A CH169928A CH169928DA CH169928A CH 169928 A CH169928 A CH 169928A CH 169928D A CH169928D A CH 169928DA CH 169928 A CH169928 A CH 169928A
- Authority
- CH
- Switzerland
- Prior art keywords
- compounds
- oxynaphthotriazole
- preparation
- amino
- parts
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 3
- 239000000975 dye Substances 0.000 claims description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 229910052802 copper Inorganic materials 0.000 claims description 4
- 239000010949 copper Substances 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 239000003929 acidic solution Substances 0.000 claims description 3
- 239000007800 oxidant agent Substances 0.000 claims description 3
- XJCVRTZCHMZPBD-UHFFFAOYSA-N 3-nitroaniline Chemical compound NC1=CC=CC([N+]([O-])=O)=C1 XJCVRTZCHMZPBD-UHFFFAOYSA-N 0.000 claims description 2
- 150000008049 diazo compounds Chemical class 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 239000000987 azo dye Substances 0.000 claims 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 239000005749 Copper compound Substances 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 150000001880 copper compounds Chemical class 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 150000003852 triazoles Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- UKKKDTZQJJBVJA-UHFFFAOYSA-N 5-diazo-1-nitrocyclohexa-1,3-diene Chemical compound [N+](=O)([O-])C=1CC(C=CC1)=[N+]=[N-] UKKKDTZQJJBVJA-UHFFFAOYSA-N 0.000 description 1
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 1
- 239000005751 Copper oxide Substances 0.000 description 1
- 239000005708 Sodium hypochlorite Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- JYYOBHFYCIDXHH-UHFFFAOYSA-N carbonic acid;hydrate Chemical compound O.OC(O)=O JYYOBHFYCIDXHH-UHFFFAOYSA-N 0.000 description 1
- 229910000431 copper oxide Inorganic materials 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung eines Oxynaphttriazols. Gemäss dem im Hauptpatent beschriebenen Verfahren erhält man ein Oxynaphttriazol, wenn man den aus 4-Nitr-o-l-diazobenzol durch saure Kupplung mit 1-Amino-8-oxynaphtalin- 3.6-disulfosäure erhältlichen o-Aminoazofarb- stoff mit Verbindungen des zweiwertigen Kupfers oxydiert, beziehungsweise mit andern Oxydationsmitteln in Gegenwart von zwei wertigen Kupferverbindungen behandelt.
Wie nun weiter gefunden wurde, erhält man ein ähnliches, für die gleichen Zwecke brauchbares Oxynaphttriazol, wenn man den Farbstoff, wie er aus 3-Nitro-l-diazobenzol und Kuppeln mit 2-Amino-8-ogynaphtalin-6- sulfosäure in saurer Lösung erhältlich ist, mit Verbindungen des zweiwertigen Kupfers behandelt.
Die Oxydation kann in neutraler, alkali scher, ammoniakalischer oder saurer Lösung durchgeführt werden. Andere Oxydations mittel, die für sich allen nicht zum Ziel führen, beispielsweise Wasserstoffsuperoxyd, Natriumhypochlorit können in Gegenwart von zur Triazolbildung unzureichenden Mengen Kupferverbindung für den genannten Zweck Verwendung finden. .
Das erhaltene, bisher nicht bekannte Oxy- naphttriazol bildet ein wertvolles Zwischen produkt für die Herstellung von Farbstoffen. <I>Beispiel:</I> Der aus 13,8 Teilen diazotiertem 3-Nitro- 1-aminobenzol und 23,9 Teilen 2-Amino-8- oxynaphtalin-6-sulfosäure in mineralsaurer Lösung gebildete 1-Aminoazofarbstoff wird in etwa 1000 Teilen Wasser und Natrium- carbonat neutral gelöst, mit 22 Teilen Na triumcarbonat im Überschuss versetzt,
worauf in der Siedehitze 52 Teile Kupfersulfat kristal lisiert in wässeriger Lösung zulaufen, wo durch die Farbe der Lösung unter Triazol- bildung in gelb umschlägt. Man verdünnt dann auf etwa 2000 Volumenteile, gibt noch 15 Teile Natriumcarbonat hinzu und filtriert vom ausgeschiedenen Kupferoxydul ab. Aus dem gelben Filtrat wird das Oxynaphttriazol durch Zugabe von Chlornatrium abgeschieden. Es bildet ein gelbbraunes Pulver, das sich in Wasser mit gelber Farbe löst, die bei Zu satz von überschüssigem Alkali orange wird und kuppelt leicht mit Diazoverbindungen.
Process for the preparation of an oxynaphthotriazole. According to the process described in the main patent, an oxynaphthotriazole is obtained if the o-aminoazo dye obtainable from 4-nitr-ol-diazobenzene by acidic coupling with 1-amino-8-oxynaphthalene-3,6-disulfonic acid is oxidized with compounds of divalent copper, or treated with other oxidizing agents in the presence of two valent copper compounds.
As has now been found further, a similar oxynaphthotriazole which can be used for the same purposes is obtained if the dye, as obtained from 3-nitro-1-diazobenzene and domes with 2-amino-8-ogynaphthalene-6-sulfonic acid, is in acidic solution is available, treated with compounds of divalent copper.
The oxidation can be carried out in neutral, alkaline, ammoniacal or acidic solution. Other oxidizing agents that do not all achieve their goal, for example hydrogen peroxide, sodium hypochlorite, can be used for the stated purpose in the presence of insufficient amounts of copper compound to form triazoles. .
The previously unknown oxynaphthotriazole is a valuable intermediate for the production of dyes. <I> Example: </I> The 1-aminoazo dye formed from 13.8 parts of diazotized 3-nitro-1-aminobenzene and 23.9 parts of 2-amino-8-oxynaphthalene-6-sulfonic acid in a mineral acid solution is about 1000 Parts of water and sodium carbonate dissolved neutrally, mixed with 22 parts of sodium carbonate in excess,
whereupon 52 parts of copper sulfate crystallized at the boiling point run in aqueous solution, where the color of the solution changes to yellow with formation of triazoles. It is then diluted to about 2000 parts by volume, 15 parts of sodium carbonate are added and the precipitated copper oxide is filtered off. The oxynaphthotriazole is separated from the yellow filtrate by adding sodium chloride. It forms a yellow-brown powder that dissolves in water with a yellow color, which turns orange with the addition of excess alkali and easily couples with diazo compounds.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE169928X | 1932-04-20 | ||
| CH164836T | 1932-09-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH169928A true CH169928A (en) | 1934-06-15 |
Family
ID=25718035
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH169928D CH169928A (en) | 1932-04-20 | 1932-09-24 | Process for the preparation of an oxynaphthetriazole. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH169928A (en) |
-
1932
- 1932-09-24 CH CH169928D patent/CH169928A/en unknown
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