CH274849A - Process for the preparation of a new monoazo dye. - Google Patents
Process for the preparation of a new monoazo dye.Info
- Publication number
- CH274849A CH274849A CH274849DA CH274849A CH 274849 A CH274849 A CH 274849A CH 274849D A CH274849D A CH 274849DA CH 274849 A CH274849 A CH 274849A
- Authority
- CH
- Switzerland
- Prior art keywords
- parts
- preparation
- monoazo dye
- new
- dye
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 2
- 239000000975 dye Substances 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 7
- 235000005811 Viola adunca Nutrition 0.000 claims description 2
- 240000009038 Viola odorata Species 0.000 claims description 2
- 235000013487 Viola odorata Nutrition 0.000 claims description 2
- 235000002254 Viola papilionacea Nutrition 0.000 claims description 2
- 210000002268 wool Anatomy 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 239000000203 mixture Substances 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 229940014800 succinic anhydride Drugs 0.000 description 2
- TYEYBOSBBBHJIV-UHFFFAOYSA-N 2-oxobutanoic acid Chemical compound CCC(=O)C(O)=O TYEYBOSBBBHJIV-UHFFFAOYSA-N 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- -1 aluminum compound Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 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
- 239000013078 crystal Substances 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- UIUJIQZEACWQSV-UHFFFAOYSA-N succinic semialdehyde Chemical compound OC(=O)CCC=O UIUJIQZEACWQSV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
- C09B45/14—Monoazo compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
- C09B45/14—Monoazo compounds
- C09B45/18—Monoazo compounds containing copper
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines neuen Monoazofarbstoffes. Es wurde gefunden, dass man zu einem wertvollen Monoazofarbstoff gelangt, wenn man diazotiertes 5-Nitro-4-chlor-2-amino-l-oxy- benzol mit. 1-Oxynaphthyl-(4)-y-ketobutter- säure vereinigt.
Der neue Farbstoff färbt Wolle in gelb- stichigen Bordeauxtönen, die durch Nach- chromieren in ein Blau und durch Nach kupfern in ein Blauviolett übergehen.
Die beim vorliegenden Verfahren als Aus gangsstoff zu verwendende 1-Oxynaphthyl- (4)-y-ketobuttersäure kann z. B. ,durch Kon densation von 1-Oxynaphthalin mit Bernstein säureanhydrid in Gegenwart von Aluminium chlorid oder durch alkalische Verseifung der entsprechenden 1-Alkoxynaphthyl-j(4)-y-keto- buttersäuren hergestellt werden.
Die Kupplung erfolgt beim vorliegenden Verfahren mit Vorteil in alkalischem, z. B. natriumcarbonatalkalischem Medium.
Beispiel: 189,5 Teile 5-Nitro-4-chlor-2-amino-l-oxy- benzol werden in 300 Teilen konz. Salzsäure und 500 Teilen Wasser mit 69 Teilen Natrium nitrit unter Eiskühlung diazotiert.
256 Teile 1,Oxynaphthyl-(4)-y-ketobutter- säure werden in 1000 Teilen Wasser unter Zusatz von 80 Teilen Natriumhydroxyd gelöst; dann werden 150 Teile Natriumcarbonat zu gesetzt. Zu .der so erhaltenen Lösung lässt man unter Eiskühlung die oben erwähnte Diazo- lösung langsam zufliessen und rührt einige Stunden bis zur Beendigung der Farbstoff- bildung. Man scheidet den Farbstoff durch Zugabe von Natriumchlorid aus, filtriert ab und trocknet.
Die verwendete 1-Oxynaphthyl-(4) y-keto- buttersäure kann wie folgt hergestellt werden: 1. In eine Mischung von 144 Teilen 1-Oxy- naphthalin, 100 Teilen Bernsteinsäureanhy- drid und 1200 Teilen Tetrachloräthan wer den bei 5 bis 100 270 Teile Aluminiumchlorid eingetragen.
Nach einigen Stunden wird die zähe Masse in 3000 Teile einer Mischung von Wasser und Eis eingerührt und das Tetra- choräthan wird hierauf mit Dampf abdestil- liert. Die zurückbleibende Aluminiumverbin dung wird dann bei Kochtemperatur durch Zugabe von Natriumcarbonat zersetzt und die erhaltene Reaktionsmischung wird abfiltriert. Aus dein Filtrat, das das Natriumsalz der 1- Oxynaphthalin-4-y-ketobuttersäture enthält,
wird die schwerlösliche freie Säure durch Zu gabe von Salzsäure gefällt. Sie kann nach kur zer Zeit abfiltriert werden. Die 1-Oxynaph- thalin-4-y-ketobuttersäure bildet feine Kri stalle, .die nach dem Umkristallisieren aus Al kohol bei etwa 2260 (unkorrigiert) schmelzen.
2. 258 Teile 1-Methoxynaphthyl-(4)-y-keto- buttersäure werden mit 650 Teilen einer wässerigen, 30 % igen Natriumhydroxydlösung in einem eisernen Rührautoklav während 5 Stunden auf 140 bis 145 erhitzt. Dann wird abgekühlt und mit Salzsäure. angesäuert. Man erhält 230 Teile rohe 1"Oxynaphthyl-(4)-y- ketobuttersäure vom Schmelzpunkt 2100, die gewünschtenfalls durch Umkristallisieren aus Alkohol gereinigt werden kann.
Process for the preparation of a new monoazo dye. It has been found that a valuable monoazo dye is obtained when using diazotized 5-nitro-4-chloro-2-amino-1-oxybenzene. 1-Oxynaphthyl- (4) -y-keto butyric acid combined.
The new dye dyes wool in yellow-tinged bordeaux tones, which change to blue when chromed and to blue-violet when copper is added.
The starting material to be used in the present process 1-oxynaphthyl (4) -y-ketobutyric acid can, for. B., by condensation of 1-oxynaphthalene with succinic anhydride in the presence of aluminum chloride or by alkaline saponification of the corresponding 1-alkoxynaphthyl-j (4) -y-keto-butyric acids.
In the present process, the coupling is advantageously carried out in an alkaline, e.g. B. sodium carbonate alkaline medium.
Example: 189.5 parts of 5-nitro-4-chloro-2-amino-1-oxybenzene are concentrated in 300 parts. Hydrochloric acid and 500 parts of water are diazotized with 69 parts of sodium nitrite with ice cooling.
256 parts of 1, oxynaphthyl- (4) -y-ketobutyric acid are dissolved in 1000 parts of water with the addition of 80 parts of sodium hydroxide; then 150 parts of sodium carbonate are added. The above-mentioned diazo solution is allowed to slowly flow into the solution thus obtained, while cooling with ice, and the mixture is stirred for a few hours until the formation of the dye has ended. The dye is separated out by adding sodium chloride, filtered off and dried.
The 1-oxynaphthyl- (4) γ-keto-butyric acid used can be prepared as follows: 1. In a mixture of 144 parts of 1-oxynaphthalene, 100 parts of succinic anhydride and 1200 parts of tetrachloroethane at 5 to 100,270 Parts of aluminum chloride entered.
After a few hours, the viscous mass is stirred into 3000 parts of a mixture of water and ice and the tetrachloroethane is then distilled off with steam. The remaining aluminum compound is then decomposed at boiling temperature by adding sodium carbonate and the resulting reaction mixture is filtered off. From your filtrate, which contains the sodium salt of 1-oxynaphthalene-4-y-ketobutyric acid,
the sparingly soluble free acid is precipitated by adding hydrochloric acid. It can be filtered off after a short time. The 1-oxynaphthalene-4-y-ketobutyric acid forms fine crystals which, after recrystallization from alcohol, melt at around 2260 (uncorrected).
2. 258 parts of 1-methoxynaphthyl- (4) -y-keto-butyric acid are heated to 140 to 145 for 5 hours with 650 parts of an aqueous 30% sodium hydroxide solution in an iron stirred autoclave. Then it is cooled and with hydrochloric acid. acidified. 230 parts of crude 1 ″ oxynaphthyl- (4) -y ketobutyric acid with a melting point of 2100 are obtained, which, if desired, can be purified by recrystallization from alcohol.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH274849T | 1950-03-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH274849A true CH274849A (en) | 1951-04-30 |
Family
ID=4479938
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH274849D CH274849A (en) | 1950-03-17 | 1949-05-19 | Process for the preparation of a new monoazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH274849A (en) |
-
1949
- 1949-05-19 CH CH274849D patent/CH274849A/en unknown
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