CH169934A - Process for the preparation of an oxynaphthetriazole. - Google Patents
Process for the preparation of an oxynaphthetriazole.Info
- Publication number
- CH169934A CH169934A CH169934DA CH169934A CH 169934 A CH169934 A CH 169934A CH 169934D A CH169934D A CH 169934DA CH 169934 A CH169934 A CH 169934A
- Authority
- CH
- Switzerland
- Prior art keywords
- compounds
- preparation
- oxynaphthotriazole
- nitro
- copper
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 239000000975 dye Substances 0.000 claims description 7
- 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
- 239000007800 oxidant agent Substances 0.000 claims description 3
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 claims description 2
- 150000008049 diazo compounds Chemical class 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 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 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 239000003929 acidic solution Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 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
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 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
- 239000005749 Copper compound Substances 0.000 description 1
- 239000005708 Sodium hypochlorite Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- JYYOBHFYCIDXHH-UHFFFAOYSA-N carbonic acid;hydrate Chemical compound O.OC(O)=O JYYOBHFYCIDXHH-UHFFFAOYSA-N 0.000 description 1
- 150000001880 copper compounds Chemical class 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
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007935 neutral effect Effects 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 OgynaphttAazols. Gemäss dem im Hauptpatent beschriebe nen Verfahren erhält man ein Oxynaplittria- zol, wenn man den aus 4-Nitro-l-diazobenzol durch saure Kupplung mit 1-Ainirro-8-oxy- rraplitalin-3. 6-disulfosäure erhältlichen o-Aiiii- noazofarbstoff mit Verbindungen des zwei wertigen Kupfers oxydiert bezw. 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 4-Nitro-l-diazobenzol durch Kuppeln mit 1-Amino-8-oxynaphthaliii- 4-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 allein nicht zum Ziel führen, beispielsweise Wasserstoffsuperoxyd, Natr.iumhypochlorit, können in Gegenwart von zur Triazolbildung unzureichenden Men gen 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 4-Nitro- 1- aminobenzol und 23,9 Teilen 1-Amino- 8-oxynäphtalin-4-sulfosäure in mineralsaurer Lösung gebildete 1-Aminoazofarbstoff wird in etwa 1000 Teilen Wasser und Natriumcarbo- nat neutral gelöst und mit weiteren 22 Teilen Natriumcarbonat im Überschuss versetzt.
Zu dieser Farbstofflösung läuft eine Lösung von 52 Teilen Kupfersulfat kristallisiert. Die Oxy dation ist beendet, sobald die Farbe der Lösung unter Triazolbildung in gelb umge schlagen ist. Nach dem Aufarbeiten bildet das Oxynaphttriazol ein gelbbraunes Pulver, das sich in Wasser mit gelber Farbe löst und leicht mit Diazoverbindungen kuppelt.
Method for the preparation of an ogynaphttaazole. According to the process described in the main patent, an oxynaplittria- zole is obtained when the from 4-nitro-1-diazobenzene is obtained by acidic coupling with 1-ainirro-8-oxyrraplitalin-3. 6-disulfonic acid available o-Aiiii- noazo dye with compounds of divalent copper oxidized or. treated with other oxidizing agents in the presence of two valent copper compounds.
As has now been further found, a similar oxynaphthotriazole which can be used for the same purposes is obtained if the dye is obtained from 4-nitro-1-diazobenzene by coupling with 1-amino-8-oxynaphthalene-4-sulfonic acid in acidic solution is available, treated with compounds of divalent copper.
The oxidation can take place in neutral; alkaline, ammoniacal or acidic solution. Other oxidizing agents that do not achieve the goal on their own, for example hydrogen peroxide, sodium hypochlorite, can be used for the stated purpose in the presence of insufficient amounts of triazole formation.
The previously unknown oxynaphthotriazole obtained forms a valuable intermediate for the production of dyes. <I> Example: </I> The 1-aminoazo dye formed from 13.8 parts of diazotized 4-nitro-1-aminobenzene and 23.9 parts of 1-amino-8-oxynäphtalin-4-sulfonic acid in a mineral acid solution becomes about 1000 Parts of water and sodium carbonate dissolved neutrally and treated with a further 22 parts of sodium carbonate in excess.
A solution of 52 parts of crystallized copper sulfate runs into this dye solution. The oxidation is complete as soon as the color of the solution has turned yellow with formation of triazoles. After working up, the oxynaphthotriazole forms a yellow-brown powder which dissolves in water with a yellow color and easily couples with diazo compounds.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE169934X | 1932-04-20 | ||
| CH164836T | 1932-09-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH169934A true CH169934A (en) | 1934-06-15 |
Family
ID=25718041
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH169934D CH169934A (en) | 1932-04-20 | 1932-09-24 | Process for the preparation of an oxynaphthetriazole. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH169934A (en) |
-
1932
- 1932-09-24 CH CH169934D patent/CH169934A/en unknown
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