CH169933A - Process for the preparation of an oxynaphthetriazole. - Google Patents
Process for the preparation of an oxynaphthetriazole.Info
- Publication number
- CH169933A CH169933A CH169933DA CH169933A CH 169933 A CH169933 A CH 169933A CH 169933D A CH169933D A CH 169933DA CH 169933 A CH169933 A CH 169933A
- Authority
- CH
- Switzerland
- Prior art keywords
- compounds
- preparation
- divalent copper
- oxynaphttriazole
- oxynaphthetriazole
- 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
- 239000002253 acid 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
- 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
- -1 aminoazo Chemical group 0.000 claims 1
- 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
- 239000003929 acidic solution Substances 0.000 description 2
- 239000007864 aqueous solution Substances 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
- 239000005749 Copper compound Substances 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
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001880 copper compounds Chemical class 0.000 description 1
- 229910000431 copper oxide 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 Oxynaplittriazols. Gemäss dem im Hauptpatent beschriebe nen Verfahren erhält man ein Oxynaphttriazol, wenn man den aus 4-Nitro-l-diazobenzol durch saurdKupplung mit 1-Amino-8-oxynaph- talin-3.6-disulfosäure erhältlichen o-Amino- azofarbstoff mit Verbindungen des zweiwer tigen Kupfers oxydiert beziehungsweise mit andern 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 1-Amicio-8-oxy- iiaphtalin-4-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 sieh allein nicht zum Ziel führen, beispielsweise Wasserstoffsuperoxyd, Natriumhypochlorit, 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 durch mineralsaure Kupplung aus 15,3 Teilen monodiazotiertem 1.3-Diamino- 4-nitrobenzol und 23.9 Teilen 1-Amino-8- oxynaphtalin-4-sulfosäure erhaltene Farbstoff wird in wässeriger Lösung unter Erwärmen und bei Gegenwart überschüssigen Natrium- carbonats mit einer Lösung von 52 Teilen kristallisiertem Kupfersulfatversetztund kurze Zeit auf<B>95'</B> erwärmt,
bis die Farbe in gelb braun umgeschlagen ist. Nach Abfiltrieren des ausgeschiedenen 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 oxynaplitetriazole. According to the process described in the main patent, an oxynaphthotriazole is obtained when the o-aminoazo dye obtainable from 4-nitro-1-diazobenzene by acidic coupling with 1-amino-8-oxynaphthalen-3,6-disulfonic acid is mixed with compounds of the divalent Copper is oxidized or treated with other oxidizing agents in the presence of divalent 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 monodiazotized 1,3-diamino-4-nitrobenzene and 1-amicio-8-oxy-iiaphthalene-4-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 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 dye obtained by mineral acid coupling from 15.3 parts of monodiazotized 1,3-diamino-4-nitrobenzene and 23.9 parts of 1-amino-8-oxynaphthalene-4-sulfonic acid is dissolved in aqueous solution with heating and with In the presence of excess sodium carbonate, a solution of 52 parts of crystallized copper sulphate is added and heated to <B> 95 '</B> for a short time,
until the color has turned yellow-brown. After the precipitated 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 |
|---|---|---|---|
| DE169933X | 1932-04-20 | ||
| CH164836T | 1932-09-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH169933A true CH169933A (en) | 1934-06-15 |
Family
ID=25718040
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH169933D CH169933A (en) | 1932-04-20 | 1932-09-24 | Process for the preparation of an oxynaphthetriazole. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH169933A (en) |
-
1932
- 1932-09-24 CH CH169933D patent/CH169933A/en unknown
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