CH169931A - Process for the preparation of an oxynaphthetriazole. - Google Patents
Process for the preparation of an oxynaphthetriazole.Info
- Publication number
- CH169931A CH169931A CH169931DA CH169931A CH 169931 A CH169931 A CH 169931A CH 169931D A CH169931D A CH 169931DA CH 169931 A CH169931 A CH 169931A
- Authority
- CH
- Switzerland
- Prior art keywords
- compounds
- preparation
- divalent copper
- oxynaphthalene
- amino
- 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 6
- 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
- DPIZKMGPXNXSGL-UHFFFAOYSA-N 4-nitro-1,3-phenylenediamine Chemical compound NC1=CC=C([N+]([O-])=O)C(N)=C1 DPIZKMGPXNXSGL-UHFFFAOYSA-N 0.000 claims description 3
- 239000003929 acidic solution Substances 0.000 claims description 3
- 239000007800 oxidant agent Substances 0.000 claims description 3
- 150000008049 diazo compounds Chemical class 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 239000005749 Copper compound Substances 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000001880 copper compounds Chemical class 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 150000003852 triazoles Chemical class 0.000 description 2
- SSQQBRZUIXIPIP-UHFFFAOYSA-N 5-diazo-2-nitrocyclohexa-1,3-diene Chemical compound [O-][N+](=O)C1=CCC(=[N+]=[N-])C=C1 SSQQBRZUIXIPIP-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 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
- 239000002253 acid Substances 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
- 238000010438 heat treatment Methods 0.000 description 1
- 238000004519 manufacturing process Methods 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
- 229910000029 sodium carbonate Inorganic materials 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
- 239000000243 solution Substances 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 - Nitro -1 - diazobenzol durch saure Kupplung mit 1-Amino-8-oxy- naphtalin - 3 . 6 - disulfosäure erhältlichen o Amitioazofarbstoff mit Verbindungen des zweiwertigen Kupfers oxydiert bezw. mit an dern Oxydationsmitteln in Gegenwart von zweiwertigen Kupferverbindungen behandelt.
Wie nun weiter gefunden wurde, erhält man ein ähnliches, für die gleichen Zwecke brauchbares Oxynaphttriazol, wenn man den Farbstoff, wie er aus monodiazotiertem 1.3- Diamino-4-nitrobenzol und 2-Amino-8-oxy- naphtalin-6-sulfosäure in saurer Lösung er hältlich ist, mit Verbindungen des zweiwer tigen Kupfers behandelt.
Die Oxydation kann in neutraler, alkali scher, ammoniakalischer oder saurer Lösung durchgeführt werden. Andere Oxydations mittel, die für sich allein nicht zum Ziel füh ren, beispielsweise Wasserstoffsuperoxyd, Na.. triumhypochlorit, 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 durch saure Kupplung aus 15,3 Teilen monodiazotiertem 1.3-Diamino-4-nitrobenzol und 23,9 Teilen 2-Amino-8-oxynaphtalin-6 sulfosäure erhaltene Farbstoff wird in wässe riger Lösung unter Erwärmen und bei Gegen wart überschüssigen Natriumkarbonats mit einer Lösung von 52 Teilen krist. Kupfer sulfat versetzt und kurze Zeit auf 95 er wärmt, bis die Farbe in gelbbraun umge schlagen ist.
Nach Abfiltrieren des ausge schiedenen Kupferoxyduls wird das Triazol aus der wässerigen Lösung durch Zugabe von Chlornatrium zur Abscheidung gebracht Es stellt ein gelbbraunes Pulver dar 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 from 4-nitro-1-diazobenzene is obtained by acidic coupling with 1-amino-8-oxynaphthalene-3. 6 - disulfonic acid available o amitioazo dye with compounds of divalent copper oxidized or. Treated with other oxidizing agents in the presence of divalent copper compounds.
As has now been found further, a similar oxynaphthotriazole which can be used for the same purposes is obtained if the dye is obtained from monodiazotized 1,3-diamino-4-nitrobenzene and 2-amino-8-oxynaphthalene-6-sulfonic acid in acidic Solution he is available, treated with compounds of two-valued copper.
The oxidation can be carried out in neutral, alkaline, ammoniacal or acidic solution. Other oxidizing agents that do not achieve the goal by themselves, 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 obtained forms a valuable intermediate for the production of dyes. <I> Example: </I> The dye obtained by acidic coupling from 15.3 parts of monodiazotized 1,3-diamino-4-nitrobenzene and 23.9 parts of 2-amino-8-oxynaphthalene-6 sulfonic acid is dissolved in an aqueous solution with heating and in the presence of excess sodium carbonate with a solution of 52 parts of crystalline. Copper sulfate is added and warms up to 95 for a short time until the color has turned yellowish brown.
After the separated copper oxide has been filtered off, the triazole is separated from the aqueous solution by adding sodium chloride. It is a yellow-brown powder and easily couples with diazo compounds.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE169931X | 1932-04-20 | ||
| CH164836T | 1932-09-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH169931A true CH169931A (en) | 1934-06-15 |
Family
ID=25718038
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH169931D CH169931A (en) | 1932-04-20 | 1932-09-24 | Process for the preparation of an oxynaphthetriazole. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH169931A (en) |
-
1932
- 1932-09-24 CH CH169931D patent/CH169931A/en unknown
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