CH261068A - 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
- CH261068A CH261068A CH261068DA CH261068A CH 261068 A CH261068 A CH 261068A CH 261068D A CH261068D A CH 261068DA CH 261068 A CH261068 A CH 261068A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- carboxylic acid
- anthraquinone
- methylamino
- 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
- 239000000975 dye Substances 0.000 claims description 7
- DFHWKIDPYFUEIP-UHFFFAOYSA-N 4-cyano-1-(methylamino)-9,10-dioxoanthracene-2-carboxylic acid Chemical class CNC1=C(C=C(C=2C(C3=CC=CC=C3C(C12)=O)=O)C#N)C(=O)O DFHWKIDPYFUEIP-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 3
- FWEQPMZEKHHFTB-UHFFFAOYSA-N n-(5-amino-9,10-dioxoanthracen-1-yl)benzamide Chemical compound C1=CC=C2C(=O)C=3C(N)=CC=CC=3C(=O)C2=C1NC(=O)C1=CC=CC=C1 FWEQPMZEKHHFTB-UHFFFAOYSA-N 0.000 claims description 3
- 239000000843 powder Substances 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
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 235000013311 vegetables Nutrition 0.000 claims description 2
- 239000012188 paraffin wax Substances 0.000 claims 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 3
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 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
- 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
- QCANMOGGSLPAQO-UHFFFAOYSA-N 4-bromo-1-(methylamino)-9,10-dioxoanthracene-2-carboxylic acid Chemical compound CNC1=C(C=C(Br)C2=C1C(=O)C1=CC=CC=C1C2=O)C(O)=O QCANMOGGSLPAQO-UHFFFAOYSA-N 0.000 description 1
- ASDLSKCKYGVMAI-UHFFFAOYSA-N AQC Natural products C1=CC=C2C(=O)C3=CC(C(=O)O)=CC=C3C(=O)C2=C1 ASDLSKCKYGVMAI-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 239000000155 melt 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
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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/36—Dyes with acylated amino groups
- C09B1/42—Dyes with acylated amino groups the acyl groups being residues of an aromatic carboxylic acid
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Zusatzpatent zum Hauptpatent Nr. 253257. 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-Methylamino-4-cyananthrachi- non - 2 - carbonsäure mit 1-Amino - 5-benzoyl- aminoanthrachinon umsetzt.
Der neue Farbstoff ist ein rotes Pulver, das Baumwolle sowie andere pflanzliche Fa sern aus bordeauxfarbener Küpein roten Tö nen färbt.
Die dem vorliegenden Verfahren als Aus gangsstoffe dienende 1-1@Tethylamino-4-eyan- anthrachinon-2-carbonsäure kann aus 1-Me- thylamino -4- bromanthrachinon-2-carbonsäure durch zwölfstündiges Erhitzen auf 1800 mit Cuprocyanid in Nitrobenzol in Gegenwart von Pyridin gewonnen werden. Sie stellt ein rotbraunes Pulver dar, das bei<B>2900</B> unter Zersetzung schmilzt. Die überführung der Carbonsäure in ein funktionelles Derivat, zweckmässig ein solches von hoher Reaktions fähigkeit, z.
B. ein Säurehalogenid, insbeson dere das Säurechlorid, kann in bekannter Weise, zweckmässig durch Umsetzen mit Thio- nylchlorid, bewerkstelligt werden.
Die Reaktion des funktionellen Derivates der genannten Carbonsäure mit der Amino- anthrachinonkomponente kann zweckmässig in einem hochsiedenden Lösungs- bzw. Vertei lungsmittel, wie Nitrobenzol, Mono-, Di- oder Trichlorbenzol oder Naphthalin, und zweck mässig bei erhöhter Temperatur, beispiels weise zwischen etwa 80 und 2000, durchge führt werden.
<I>Beispiel:</I> 15,3 Teile 1-Methylamino-4-cyananthrachi- non-2-carbonsäure werden durch einstündiges Erhitzen auf 100e mit 60 Teilen Thionyl- chlorid und 0,1 Teil Pyridin in 2000 Teilen trockenem Nitrobenzol in das Säurechlorid verwandelt. Das überschüssige Thionylchlorid wird hierauf durch Einleiten eines trockenen Luftstromes entfernt. Nun trägt man 17,1 Teile 1-Amino-5-benzoylaminoanthrachinon ein. Nach zweistündigem Rühren bei 95 bis 1.050 und anschliessendem zweistündigem Er hitzen auf 150 bis 1600 ist die Umsetzung be endet.
Man saugt den ausgefallenen Farbstoff in der Kälte ab, wäscht mit Nitrobenzol und Alkohol aus und trocknet.
Additional patent to main patent no. 253257. Process for the production 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-methylamino-4-cyananthraquinone - 2 - carboxylic acid is reacted with 1-amino - 5-benzoylaminoanthraquinone.
The new dye is a red powder that dyes cotton and other vegetable fibers from burgundy tubs in red tones.
The present process as starting materials from 1-1 @ Tethylamino-4-eyan- anthraquinone-2-carboxylic acid can be prepared from 1-methylamino -4- bromoanthraquinone-2-carboxylic acid by heating for twelve hours to 1800 with cuprocyanide in nitrobenzene in the presence of Pyridine can be obtained. It is a red-brown powder that melts at <B> 2900 </B> with decomposition. The conversion of the carboxylic acid into a functional derivative, expediently one of high reactivity, eg.
B. an acid halide, in particular the acid chloride, can be accomplished in a known manner, expediently by reaction 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 distributing agent such as nitrobenzene, mono-, di- or trichlorobenzene or naphthalene, and expediently at elevated temperature, for example between about 80 and 2000.
<I> Example: </I> 15.3 parts of 1-methylamino-4-cyananthraquinone-2-carboxylic acid are dissolved in 2,000 parts of dry nitrobenzene by heating to 100e for one hour with 60 parts of thionyl chloride and 0.1 part of pyridine the acid chloride is transformed. The excess thionyl chloride is then removed by introducing a stream of dry air. 17.1 parts of 1-amino-5-benzoylaminoanthraquinone are now introduced. After two hours of stirring at 95 to 1,050 and then heating to 150 to 1,600 for two hours, the reaction ends.
The precipitated dye is suctioned off in the cold, washed with nitrobenzene and alcohol and dried.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH253257T | 1947-01-15 | ||
| CH261068T | 1947-01-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH261068A true CH261068A (en) | 1949-04-15 |
Family
ID=25729740
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH261068D CH261068A (en) | 1947-01-15 | 1947-01-15 | Process for the preparation of a dye of the anthraquinone series. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH261068A (en) |
-
1947
- 1947-01-15 CH CH261068D patent/CH261068A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH261068A (en) | Process for the preparation of a dye of the anthraquinone series. | |
| CH258772A (en) | Process for the preparation of a dye of the anthraquinone series. | |
| CH258775A (en) | Process for the preparation of a dye of the anthraquinone series. | |
| CH258774A (en) | Process for the preparation of a dye of the anthraquinone series. | |
| CH258773A (en) | Process for the preparation of a dye of the anthraquinone series. | |
| CH257943A (en) | Process for the production of a vat dye. | |
| CH257944A (en) | Process for the production of a vat dye. | |
| CH302419A (en) | Process for the production of a vat dye. | |
| CH267314A (en) | Process for the production of a vat dye. | |
| CH249377A (en) | Process for the production of a vat dye. | |
| CH256235A (en) | Process for the production of a new vat dye. | |
| CH291731A (en) | Process for the production of a vat dye. | |
| CH247609A (en) | Process for the production of a vat dye. | |
| CH257942A (en) | Process for the production of a vat dye. | |
| CH290508A (en) | Process for the production of a vat dye. | |
| CH257947A (en) | Process for the production of a vat dye. | |
| CH285012A (en) | Process for the production of a quinazoline derivative. | |
| CH370511A (en) | Process for the preparation of dyes of the anthraquinone series | |
| CH274710A (en) | Process for the production of a vat dye. | |
| CH282636A (en) | Process for the production of a vat dye. | |
| CH260308A (en) | Process for the production of a vat dye. | |
| CH326164A (en) | Process for the preparation of 4-amino-phthalimide-5-sulfonic acid | |
| CH298380A (en) | Process for the production of a vat dye. | |
| CH300790A (en) | Process for the production of an azo pigment. | |
| CH282633A (en) | Process for the production of a vat dye. |