DEC0000743MA - Process for the preparation of an azo dye - Google Patents
Process for the preparation of an azo dyeInfo
- Publication number
- DEC0000743MA DEC0000743MA DEC0000743MA DE C0000743M A DEC0000743M A DE C0000743MA DE C0000743M A DEC0000743M A DE C0000743MA
- Authority
- DE
- Germany
- Prior art keywords
- parts
- azo dye
- preparation
- acid
- dye
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000000987 azo dye Substances 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title description 2
- 239000002253 acid Substances 0.000 claims description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 5
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 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
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-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
- 239000000203 mixture Substances 0.000 description 2
- 238000007747 plating Methods 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ZYECOAILUNWEAL-NUDFZHEQSA-N (4z)-4-[[2-methoxy-5-(phenylcarbamoyl)phenyl]hydrazinylidene]-n-(3-nitrophenyl)-3-oxonaphthalene-2-carboxamide Chemical compound COC1=CC=C(C(=O)NC=2C=CC=CC=2)C=C1N\N=C(C1=CC=CC=C1C=1)/C(=O)C=1C(=O)NC1=CC=CC([N+]([O-])=O)=C1 ZYECOAILUNWEAL-NUDFZHEQSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 229930194542 Keto Natural products 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical class O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 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
- 239000000706 filtrate Substances 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation 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
- 210000002268 wool Anatomy 0.000 description 1
Description
Verfahren zur Herstellung eines Azofarbstoffes.Process for the preparation of an azo dye.
Es wurde gefunden, dass ein wertvoller AzofarbstoffIt has been found to be a valuable azo dye
hergestellt werden kann, wenn man **--*■ buttersäure der Formelcan be prepared using ** - * ■ butyric acid of the formula
OHOH
COCO
CH0 CH 0
8 -8th -
CH2 COOHCH 2 COOH
mit diazotierten! 2=Amino~i~oxybenzol-4"»sulfonsäureamid kuppelt.with diazotized! 2 = Amino ~ i ~ oxybenzene-4 "» sulfonic acid amide couples.
Die als Ausgangsstoff verwendbare/jl^OxynaphthiThe / jl ^ Oxynaphthi
C ί—C ί—
Sceto-buttersäure obiger Formel kann durch Umsetzung von 1-Sceto-butyric acid of the above formula can be obtained by reacting 1-
Oxynaphthalin mit reaktionsfähigen Derivaten der Bernsteinsäure z.B. mit einem der Säurechloride oder vorzugsweise mit dem Bernsteinsäureanhydrid, zweckmässig unter Mitverwsndung eines Konden= sationsmittels wie Aluminiumchlorid hergestellt werden0 Oxynaphthalene can be prepared with reactive derivatives of succinic acid, for example with one of the acid chlorides or preferably with succinic anhydride, expediently with the use of a condensation agent such as aluminum chloride 0
Die Kupplung lässt sich vorteilhaft in alkalischem Mi 11 e1 dur chf ühr eη.The coupling can advantageously be carried out in alkaline Mi 11 e1.
Im nachfolgenden Beispiel bedeuten die Teile Gewichfcsteile und die Prozente Gewichtsprozente,.In the following example, the parts are parts by weight and the percentages are percentages by weight.
2 - 2 -
152 Teile 2=Amino=l=oxybenzol=4~sulfonsäureamid werden in 1000 Teilen Wasser unter Eiskühlung mit 250 Raumteilen konzen= trierter Salzsäure und 69 Teilen Natriumnitrit dlazotiert. 256 Teile/^=0xynaphtha?3aif-{i|;)/-^<'=lceto»buttersäure werden in 1000 Teilen Wasser unter Zusatz von 80 Teilen Natriumhydroxyd gelöst? dann werden 150 Teile Natriumcarbonat zugesetzt. Zu der so erhaltenen Lösung lässt man unter Eiskühlung die oben erwähnte Diasolösung langsam zufliessen und rührt einige Stunden bis zur Beendigung der Farbstoffbildung= Man scheidet den Farbstoff durch Zugabe von Natriumchlorid aus, filtriert ab und trocknet. Der erhaltene Farbstoff färbt Wolle aus saurem Bade in roten Tönen,, Durch Nachchromieren erhält man ein Rotviolett, durch Nachkupfern ein reines Rot in guter Echtheit.152 parts of 2 = amino = 1 = oxybenzene = 4-sulfonic acid amide are dlazotized with 250 parts by volume of concentrated hydrochloric acid and 69 parts of sodium nitrite in 1000 parts of water while cooling with ice. 256 parts / ^ = 0xynaphtha? 3aif- { i |;) / - ^ < '= lceto »butyric 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 slide solution is slowly added to the solution obtained in this way, 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 dye obtained dyes wool from an acid bath in red shades. Chromium-plating gives a red-violet, copper plating gives a pure red with good fastness.
17; Ψι Die als Ausgangsprodukt verwendbare/fi-Oxynaphthafefi'= 1 7 ; Ψι The usable as a starting product / fi-Oxynaphthafefi '=
ί ■-ί ■ -
Aijl-^Meeto-buttersaure kann wie folgt hergestellt werden :Aijl- ^ Meeto-butyric acid can be made as follows:
In eine Mischung von Ikk Teilen l~0xynaphthalin, 100 Teilen Bernsteinsäureanhydrid und 1200 Teilen Tetrachlor·= äthan werden bei 5-10° 270 Teile Aluminiumchlorid eingetragen» Nach einigen Stunden wird die zähe Masse in 3000 Teile einer Mischung von Wasser und Eis eingerührt und das Tetrachloräthan wird hierauf mit Dampf abdestilliert,. Die zurückbleibende270 parts of aluminum chloride are introduced into a mixture of Ikk parts of l-oxynaphthalene, 100 parts of succinic anhydride and 1200 parts of tetrachloroethane at 5-10 ° Tetrachloroethane is then distilled off with steam. The one left behind
x/ Verbindung wird dann bei Ke-efei;emperatur durch Zugabe x / compound is then at Ke-efei; emperatur by adding
von Natriumcarbonat gelöst und die erhaltene Reaktionsmischung wird abfiltriert. Aus dem Filtrat, das das Natriumsalz derdissolved by sodium carbonate and the resulting reaction mixture is filtered off. From the filtrate, which is the sodium salt of
3 -3 -
/K-^jl-Oxynaphtha^&^l^-lfeto-buttersaure enthält, wird die schwer lösliche freie Säure durch Zugabe von Salssäure gefällt. Sie/ K- ^ jl-Oxynaphtha ^ & ^ l ^ -lfeto-butyric acid, the sparingly soluble free acid is precipitated by adding hydrochloric acid. she
9 /ET / 9 / ET /
kann nach kurzer Zeit abfiltriert werden. Dief fl=0xynaphthai4«.^c-can be filtered off after a short time. The f fl = 0xynaphthai4 «. ^ C-
—/^|^"-keto=buttersäure bildet feine Kristalle, die nach dem Umkristallisieren aus Alkohol bei etwa 226° (unkorrigiert) schmelzen.- / ^ | ^ "- keto = butyric acid forms fine crystals, which after recrystallization from alcohol at about 226 ° (uncorrected) melt.
Claims (1)
Family
ID=
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