CH294699A - Process for the preparation of an α- (oxyphenylamino) anthraquinone. - Google Patents
Process for the preparation of an α- (oxyphenylamino) anthraquinone.Info
- Publication number
- CH294699A CH294699A CH294699DA CH294699A CH 294699 A CH294699 A CH 294699A CH 294699D A CH294699D A CH 294699DA CH 294699 A CH294699 A CH 294699A
- Authority
- CH
- Switzerland
- Prior art keywords
- anthraquinone
- oxyphenylamino
- preparation
- parts
- methylamino
- Prior art date
Links
- 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
- 238000000034 method Methods 0.000 title claims description 3
- 150000004056 anthraquinones Chemical class 0.000 title description 3
- 238000002360 preparation method Methods 0.000 title description 2
- 230000002378 acidificating effect Effects 0.000 claims description 4
- SUORACXIDJKJSQ-UHFFFAOYSA-N 1-(4-methoxyanilino)-4-(methylamino)anthracene-9,10-dione Chemical compound C1=2C(=O)C3=CC=CC=C3C(=O)C=2C(NC)=CC=C1NC1=CC=C(OC)C=C1 SUORACXIDJKJSQ-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 229910015900 BF3 Inorganic materials 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 235000002639 sodium chloride Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- IIPRUQZTMZETSL-UHFFFAOYSA-N 1-bromo-4-(methylamino)anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(Br)=CC=C2NC IIPRUQZTMZETSL-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 229910000765 intermetallic Inorganic materials 0.000 description 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure 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
- C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
- C09B1/32—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups
- C09B1/325—Dyes with no other substituents than the amino groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines a.(Oxyphenylandno)-anthraehinons. Es wurde gefunden, dass man in einfacher Weise 1=2NIet.hylamino-4-(4'-oxyphenylamino)- anthrachinon erhält, wenn man 1--.NTethyl- amino-4- (4'-methoxyphenylamino)-anthrachi- non mit sauren Mitteln bei niedrigeren Tem peraturen behandelt, als bei welchen ringför mige Verbindungen, wie die Coeramidonine oder Carbazole, entstehen. .
Geeignete saure Mittel sind beispielsweise Halogenwasserstoffsäuren, zweckmässig in Form ihrer Salze mit tertiären Aminen, oder Schwefelsäure oder hydrolytisch spaltbare Halogenide mehrwertiger Elemente, wie Bor- trifluorid, Bortriehlorid oder wasserfreies Ahi- miniumchlorid. Die zuletzt. genannten Met.all- halogenicle werden vorteilhaft, in Form von Komplexverbindungen angewandt.;
so sind die Verbindungen aus Essigsäure und Borfluorid oder aus Aluminiumehlorid und Schwefel dioxyd oder Phosgen besonders geeignet.
Das erhaltene, an sich bekannte 1-MetKyl- amino - 4 - (4'-oxyphenylamino)-anthrachinon kann als Farbstoff oder auch als Zwischen erzeugnis zur Herstellung von Farbstoffen verwendet werden.
Die in folgenden Beispielen genannten Teile sind Gewichtsteile. Beispiel <I>1:</I> In ein flüssiges Gemisch aus 5 Teilen Aluminiiunchlorid in flüssigem Schwefel- dioxyd, das noch etwa 10 % seines Gewichtes an Kochsalz enthalten kann (vgl. französische Patentsehrift Nr.
84425), trägt man unter Rühren 1 Teil 1-Methylamino-4-(4'-methoxy- phenylamino) - anthrachinon (erhalten durch Umsetzen von 1-Methylamino-4 bromanthra- chinon mit 1-Amino-4-methoxybenzol) bei ge wöhnlicher Temperatur ein und rührt so lange weiter, bis nur noch 1-1Vlethylamino-4- (4'-oxyphenylamino)-anthrachinon vorhanden ist. Dann giesst man das Gemisch in Wasser und arbeitet. es in der üblichen Weise auf.
Man erhält eine blaue, metallisch glänzende Verbindung, die in konzentrierter Schwefel säure mit blaugrauer Farbe und in Aceton mit. blaugrüner Farbe löslich ist.
<I>Beispiel 2:</I> Ein Gemisch von 10 Teilen 1.-1blet.hylamino- 4-(4'-methoxyphenylaniino)-anthrachinon und 200 Teilen 80prozentiger Schwefelsäure wird so lange bei 20 bis 25 gerührt, bis kein Aus gangsstoff mehr nachgewiesen werden kann. Nach der üblichen Aufarbeitung erhält man das 1-blethylamino-4-(4'-oxyphenylamino)-an- thrachinon.
Process for the preparation of a. (Oxyphenylandno) -anthraehinons. It has been found that 1 = 2Niet.hylamino-4- (4'-oxyphenylamino) anthraquinone is obtained in a simple manner if 1 - .Nethylamino-4- (4'-methoxyphenylamino) anthraquinone is obtained with treated acidic agents at temperatures lower than those in which ringför shaped compounds, such as the coeramidonines or carbazoles, arise. .
Suitable acidic agents are, for example, hydrohalic acids, expediently in the form of their salts with tertiary amines, or sulfuric acid or hydrolytically cleavable halides of polyvalent elements such as boron trifluoride, boron trichloride or anhydrous aluminum chloride. The last. Met.all- halogenicle mentioned are advantageously used in the form of complex compounds .;
the compounds of acetic acid and boron fluoride or of aluminum chloride and sulfur dioxide or phosgene are particularly suitable.
The 1-MetKyl-amino-4 - (4'-oxyphenylamino) -anthraquinone obtained, known per se, can be used as a dye or as an intermediate product for the production of dyes.
The parts mentioned in the following examples are parts by weight. Example <I> 1: </I> In a liquid mixture of 5 parts of aluminum chloride in liquid sulfur dioxide, which can still contain about 10% of its weight in table salt (cf. French patent publication no.
84425), 1 part of 1-methylamino-4- (4'-methoxyphenylamino) anthraquinone (obtained by reacting 1-methylamino-4-bromoanthraquinone with 1-amino-4-methoxybenzene) is added with stirring Temperature and stir until only 1-1Vlethylamino-4- (4'-oxyphenylamino) -anthraquinone is present. Then you pour the mixture into water and work. it up in the usual way.
A blue, shiny metallic compound is obtained which is acidic in concentrated sulfur with a blue-gray color and in acetone. blue-green color is soluble.
<I> Example 2: </I> A mixture of 10 parts of 1.-1blet.hylamino- 4- (4'-methoxyphenylaniino) anthraquinone and 200 parts of 80 percent sulfuric acid is stirred at 20 to 25 until no starting material is used more can be proven. After the usual work-up, 1-methylamino-4- (4'-oxyphenylamino) -anthrachinone is obtained.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE294699X | 1942-05-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH294699A true CH294699A (en) | 1953-11-30 |
Family
ID=6086575
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH294699D CH294699A (en) | 1942-05-12 | 1943-08-02 | Process for the preparation of an α- (oxyphenylamino) anthraquinone. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH294699A (en) |
-
1943
- 1943-08-02 CH CH294699D patent/CH294699A/en unknown
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