CH258774A - Process for the preparation of a dye of the anthraquinone series. - Google Patents
Process for the preparation of a dye of the anthraquinone series.Info
- Publication number
- CH258774A CH258774A CH258774DA CH258774A CH 258774 A CH258774 A CH 258774A CH 258774D A CH258774D A CH 258774DA CH 258774 A CH258774 A CH 258774A
- Authority
- CH
- Switzerland
- Prior art keywords
- amino
- dye
- carboxylic acid
- cyananthraquinone
- anthraquinone series
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 title claims description 4
- 150000004056 anthraquinones Chemical class 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 2
- 239000000975 dye Substances 0.000 claims description 9
- GEGNFNLNSCIKFP-UHFFFAOYSA-N 1-amino-4-cyano-9,10-dioxoanthracene-2-carboxylic acid Chemical class NC1=C(C=C(C=2C(C3=CC=CC=C3C(C12)=O)=O)C#N)C(=O)O GEGNFNLNSCIKFP-UHFFFAOYSA-N 0.000 claims description 5
- KXOGXZAXERYOTC-UHFFFAOYSA-N 1-amino-4-methoxyanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(N)=CC=C2OC KXOGXZAXERYOTC-UHFFFAOYSA-N 0.000 claims description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 239000000835 fiber Substances 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 235000013311 vegetables Nutrition 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 10
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- LFKLTGPCMCEKPE-UHFFFAOYSA-N 1-amino-4-bromo-9,10-dioxoanthracene-2-carboxylic acid Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(Br)=CC(C(O)=O)=C2N LFKLTGPCMCEKPE-UHFFFAOYSA-N 0.000 description 1
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines Farbstoffes der Anthrachinonreihe. Es wurde gefunden, dass ein wertvoller Farbstoff der Anthrachinonreihe hergestellt werden kann, wenn man ein funktionelles Derivat der 1-Amino-4-cyananthrachinon-2- carbonsäure mit 1-Amino-4-methoxyanthra- chinon umsetzt.
Der neue Farbstoff ist ein rotes Pulver, das sich in konz. Schwefelsäure mit violetter Farbe löst und Baumwolle sowie andere pflanzliche Fasern aus gelbstichig bordeaux- farbener Küpe in scharlachroten Tönen färbt.
Die dem vorliegenden Verfahren als Aus gangsstoff dienende 1-Amino-4-cyananthra- ehinon-2-carbonsäure kann aus 1-Amino-4- bromanthrachinon-2-carbonsäure durch zwölf stündiges Erhitzen auf 180 mit Cuprocyanid in Nitrobenzol in Gegenwart von Pyridin ge wonnen werden.
Sie kristallisiert aus Nitro- benzol in orangeroten Nädelchen, die bei 280 unter Zersetzung schmelzen. 2Die Überfüh rung der Carbonsäure in ein funktionelles Derivat, zweckmässig ein solches von hoher Reaktionsfähigkeit, z. B. ein,Säurehalogenid, insbesondere das Säurechlorid, kann in be- kannter Weise, zweckmässig durch Umsetzen mit Thionylchlorid, bewerkstelligt werden.
Die Reaktion des funktionellen Derivates der genannten Carbonsäure mit der Amino- anthrachinonkomponente kann zweckmässig in einem hochsiedenden Lösungs- bzw. Ver teilungsmittel, wie Nitrobenzol, Mono-, Di- oder Trichlorbenzol oder Naphthalin, und zweckmässig bei erhöhter Temperatur, bei spielsweise zwischen etwa 80 und 200 , durchgeführt werden.
Beispiel <I>1:</I> 14,6 Teile 1=Amino-4-cyananthrachinon-2- carbonsäure werden durch einstündiges Er hitzen auf 100 mit 60 Teilen Thionylchlorid und 0,1 Teil Pyridin in 2000 Teilen trok- kenem Nitrobenzol in das: Säurechlorid ver wandelt. Das überschüssige Thionylchlorid wird hierauf durch Einleiten eines trockenen Luftstromes entfernt. Nun trägt man 12,7 Teile 1-Amino-4-methoxyanthrachinon ein.
Nach zweistündigem Rühren bei 95 bis 105 und anschliessendem zweistündigem Erhitzen auf<B>150</B> bis 160 ist die Umsetzung beendet. Man saugt den ausgefallenen Farbstoff in der Kälte ab, wäscht mit Nitrobenzol und Al kohol aus und trocknet. <I>Beispiel</I> In die Lösung von 12,7 Teilen 1-Amino- 4-methoxyanthrachinon in 400 Teilen trocke nem o-Dichlorbenzol werden bei 90 bis 100 15,6-Teile laAmino-4-cyananthrachinon-2-car- bonsäurechlorid eingetragen.
Unter Durchlei ten eines trockenen Luftstromesi erhitzt man das Umsetzungsgemisch zwei Stunden auf 90 bis 100 und anschliessend zwei Stunden auf 150 bis 160 ,, Maxi saugt den, ausgefallenen Farbstoff in der Wärme ab, wäscht mit o- Dichlorbenzol und Alkohol aus und trocknet.
Process for the preparation of a dye of the anthraquinone series. It has been found that a valuable dye of the anthraquinone series can be produced if a functional derivative of 1-amino-4-cyananthraquinone-2-carboxylic acid is reacted with 1-amino-4-methoxyanthraquinone.
The new dye is a red powder that is in conc. Sulfuric acid with a violet color dissolves and dyes cotton and other vegetable fibers from a yellowish burgundy vat in scarlet tones.
The 1-amino-4-cyananthraquinone-2-carboxylic acid used as the starting material for the present process can be obtained from 1-amino-4-bromoanthraquinone-2-carboxylic acid by heating to 180 for twelve hours with cuprocyanide in nitrobenzene in the presence of pyridine will.
It crystallizes from nitrobenzene in orange-red needles which melt at 280 with decomposition. The transfer of the carboxylic acid into a functional derivative, expediently one of high reactivity, e.g. B. an acid halide, especially the acid chloride, can be accomplished in a known manner, expediently by reacting with thionyl chloride.
The reaction of the functional derivative of said carboxylic acid with the amino anthraquinone component can expediently in a high-boiling solvent or distribution medium such as nitrobenzene, mono-, di- or trichlorobenzene or naphthalene, and expediently at elevated temperature, for example between about 80 and 200.
Example <I> 1: </I> 14.6 parts of 1 = amino-4-cyananthraquinone-2-carboxylic acid are heated to 100 with 60 parts of thionyl chloride and 0.1 part of pyridine in 2000 parts of dry nitrobenzene by heating for one hour that: converts acid chloride. The excess thionyl chloride is then removed by introducing a stream of dry air. Now you enter 12.7 parts of 1-amino-4-methoxyanthraquinone.
After two hours of stirring at 95 to 105 and subsequent two hours of heating to <B> 150 </B> to 160, the reaction is complete. The precipitated dye is suctioned off in the cold, washed with nitrobenzene and alcohol and dried. <I> Example </I> In the solution of 12.7 parts of 1-amino-4-methoxyanthraquinone in 400 parts of dry o-dichlorobenzene at 90 to 100 15.6 parts of la-amino-4-cyananthraquinone-2-car - registered acid chloride.
While passing through a stream of dry air, the reaction mixture is heated for two hours to 90 to 100 and then for two hours to 150 to 160. Maxi sucks the precipitated dye off in the heat, washed with o-dichlorobenzene and alcohol and dried.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH258774T | 1946-02-12 | ||
| CH253257T | 1947-01-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH258774A true CH258774A (en) | 1948-12-15 |
Family
ID=25729738
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH258774D CH258774A (en) | 1946-02-12 | 1946-02-12 | Process for the preparation of a dye of the anthraquinone series. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH258774A (en) |
-
1946
- 1946-02-12 CH CH258774D patent/CH258774A/en unknown
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