CH190036A - Process for the production of an anthraquinone derivative. - Google Patents
Process for the production of an anthraquinone derivative.Info
- Publication number
- CH190036A CH190036A CH190036DA CH190036A CH 190036 A CH190036 A CH 190036A CH 190036D A CH190036D A CH 190036DA CH 190036 A CH190036 A CH 190036A
- Authority
- CH
- Switzerland
- Prior art keywords
- weight
- carried out
- parts
- production
- copper
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title description 3
- RZVHIXYEVGDQDX-UHFFFAOYSA-N 9,10-anthraquinone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 RZVHIXYEVGDQDX-UHFFFAOYSA-N 0.000 title description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 229910052802 copper Inorganic materials 0.000 claims description 3
- 239000010949 copper Substances 0.000 claims description 3
- 229910000039 hydrogen halide Inorganic materials 0.000 claims description 3
- 239000012433 hydrogen halide Substances 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 150000001879 copper Chemical class 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- ORFSSYGWXNGVFB-UHFFFAOYSA-N sodium 4-amino-6-[[4-[4-[(8-amino-1-hydroxy-5,7-disulfonaphthalen-2-yl)diazenyl]-3-methoxyphenyl]-2-methoxyphenyl]diazenyl]-5-hydroxynaphthalene-1,3-disulfonic acid Chemical compound COC1=C(C=CC(=C1)C2=CC(=C(C=C2)N=NC3=C(C4=C(C=C3)C(=CC(=C4N)S(=O)(=O)O)S(=O)(=O)O)O)OC)N=NC5=C(C6=C(C=C5)C(=CC(=C6N)S(=O)(=O)O)S(=O)(=O)O)O.[Na+] ORFSSYGWXNGVFB-UHFFFAOYSA-N 0.000 claims 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- 241000974482 Aricia saepiolus Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- BDRTVPCFKSUHCJ-UHFFFAOYSA-N molecular hydrogen;potassium Chemical compound [K].[H][H] BDRTVPCFKSUHCJ-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines Anthrachinonderi-vates. Gegenstand vorliegender Erfindung ist ein Verfahren zur Herstellung eines Anthra- chinonderivates, durch Einwirkung von Ha logenwasserstoff abspaltenden Mitteln auf 1-p-Toluido-2'-bromanthrachinon. Als Halo genwasserstoff abspaltendes Mittel sei Ka- liumcarbonat oder Alkalihydrogyd .genannt.
Die Reaktion wird zweckmässig in einem Lösungsmittel wie Nitrobenzol, Kresol, Ben- zylalkohol oder einem aliphatischen Alkohol wie N-Butylalkohol oder Amylalkohol oder Glykol durchgeführt.
Die Abspaltung von Halogenwasserstoff kann durch Zusatz klei- n er <B>.</B> Men.. -en Kupfer oder eines Kupfersalzes beschleunigt werden.
Das erhältliche Umsetzungsprodukt ist orange gefärbt. Es löst sich in konzentrierter Schwefelsäure mit zunächst grünlichblauer, dann rein blauer Farbe. Es soll als Nüpen- farbstoff und als Zwischenprodukt für die Herstellung anderer Verbindungen (z. B. Sulfierungsprodukte oder saure Schwefel- säureester der Leukoverbindungen) ange wandt werden.
Beispiel <I>1:</I> In eine Mischung von 10 Gewichtsteilen 1-p-Toluidoanthrachinon und 40 Gewichts teilen Nitrobenzol lässt man bei Raumtempe ratur allmählich unter Umrühren eine Auf lösung von 6 Gewichtsteilen Brom in 6 Ge wichtsteilen Nitrobenzol eintropfen. Dabei tritt ein Bromatom in den Toluidorest, und zwar in o-Stellung zur Iminogruppe ein;
das gebildete 1-Toluido-2'-bromanthrachinon scheidet sich in Nädelchen ab. 4 Gewichts teile der so erhaltenen Verbindung werden in einer Auflösung von 4 Gewichtsteilen Kaliumhydrogyd in 30 Gewichtsteilen p- Kresol einige Stunden unter Umrühren zum Sieden erhitzt.
Die erkaltende Schmelze wird mit Alkohol verdünnt und zur Oxy dation der zunächst gebildeten Leukoverbin- dung wird Luft einsgeblasen. <I>Beispiel 2:</I> Eine Mischung von 4 Gewichtsteilen 1- p-Toluido-2'-bromanthrachinon, 5 Gewichts- teilen: Kaliumcarbonat, 0,1 Gewichtsteilen Kupferpulver und 50 Gewichtsteilen Nitro- benzol wird ungefähr 5 Stunden unter Um rühren ,gekocht.
Beim Erkalten scheidet sich das 6-Methyl-1. 2-phthaloylcarbazol ab, das erforderlichenfalls durch Umkristallisieren aus hochsiedenden Lösungsmitteln gereinigt werden kann. Die Kondensation mittels Ka- liumcarbonat kann auch in Chinolin ohne Verwendung von Kupfer durchgeführt wer den.
Process for the production of an anthraquinone derivative. The present invention relates to a process for the preparation of an anthrachinone derivative by the action of agents that split off halogen on 1-p-toluido-2'-bromoanthraquinone. As an agent which splits off hydrogen halide, potassium carbonate or alkali metal hydrogen may be mentioned.
The reaction is expediently carried out in a solvent such as nitrobenzene, cresol, benzyl alcohol or an aliphatic alcohol such as n-butyl alcohol or amyl alcohol or glycol.
The splitting off of hydrogen halide can be accelerated by adding small amounts of copper or a copper salt.
The available reaction product is colored orange. It dissolves in concentrated sulfuric acid with an initially greenish-blue, then purely blue color. It should be used as a pomaceous dye and as an intermediate product for the production of other compounds (e.g. sulphonation products or acidic sulfuric acid esters of leuco compounds).
Example <I> 1 </I> In a mixture of 10 parts by weight of 1-p-toluidoanthraquinone and 40 parts by weight of nitrobenzene, a solution of 6 parts by weight of bromine in 6 parts by weight of nitrobenzene is gradually added dropwise at room temperature with stirring. A bromine atom enters the toluido radical in the o-position to the imino group;
the 1-toluido-2'-bromoanthraquinone formed separates out in needles. 4 parts by weight of the compound thus obtained are heated to the boil for a few hours with stirring in a solution of 4 parts by weight of potassium hydrogen in 30 parts by weight of p-cresol.
The cooling melt is diluted with alcohol and air is blown in to oxidize the leuco compound initially formed. <I> Example 2: </I> A mixture of 4 parts by weight of 1-p-toluido-2'-bromoanthraquinone, 5 parts by weight: potassium carbonate, 0.1 part by weight of copper powder and 50 parts by weight of nitrobenzene is converted under Um stir, cooked.
When cooling down, the 6-methyl-1 separates. 2-phthaloylcarbazole, which can be purified if necessary by recrystallization from high-boiling solvents. The condensation using potassium carbonate can also be carried out in quinoline without the use of copper.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE190036X | 1934-08-01 | ||
| CH186555T | 1935-07-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH190036A true CH190036A (en) | 1937-03-31 |
Family
ID=25721382
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH190036D CH190036A (en) | 1934-08-01 | 1935-07-31 | Process for the production of an anthraquinone derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH190036A (en) |
-
1935
- 1935-07-31 CH CH190036D patent/CH190036A/en unknown
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