CH146861A - Process for the production of an anthraquinone derivative. - Google Patents
Process for the production of an anthraquinone derivative.Info
- Publication number
- CH146861A CH146861A CH146861DA CH146861A CH 146861 A CH146861 A CH 146861A CH 146861D A CH146861D A CH 146861DA CH 146861 A CH146861 A CH 146861A
- Authority
- CH
- Switzerland
- Prior art keywords
- works
- production
- blue
- anthraquinone derivative
- copper
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 10
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 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 3
- 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 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 239000000975 dye Substances 0.000 claims description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
- 239000005749 Copper compound Substances 0.000 claims description 2
- 229920000742 Cotton Polymers 0.000 claims description 2
- 240000007817 Olea europaea Species 0.000 claims description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 239000010949 copper Substances 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 150000001880 copper compounds Chemical class 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 235000019239 indanthrene blue RS Nutrition 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 1
- 239000005751 Copper oxide Substances 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- -1 amino, methylamino Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910000431 copper oxide Inorganic materials 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines Anthrachinonderivates. Die Forschung hat ergeben, dass a-stän- dige Halogenatome in Di-anthrachinon- 1 . 2. 2'. 1'-dihydroazinen (Indanthrenen) re aktionsfähig sind, so dass sie durch andere Gruppen, beispielsweise Amino- oder Hydro- xylgruppen, oder substituierte Amino- oder Hydroxylgruppen, ausgetauscht werden kön nen.
Diese a-Halogenindanthrene können mit Aminoanthrachinon, Ammoniak, Methylamin oder Anilin, zwecks Einführung der Amino-, Methylamino- oder Anilidogruppe behandelt werden. Sie können auch mit Alkoholaten oder Phenolen zwecks Herstellung von Hy- droxy-, Alkoxy- und ähnlichen Derivaten behandelt werden.
Wenn die Indanthrene zudem noch ss-ständige Halogenatome besitzen, so werden diese nicht durchwegs angegriffen. Die Halogenindanthrene können natürlich auch in ihrer Azinform verwendet werden.
Gegenstand des vorliegenden Patentes ist itun ein Verfahren zur Herstellung eines Anthrachinonderivates, dadurch gekenn zeichnet, dass man 1 Mol. 3. 3' . 4. 4'-Tetra- chlorindanthren mit 2 Mol. 1-Aminoanthra- chinon kondensiert.
Diese Reaktion kann in Gegenwart von Säure abstumpfenden Mitteln durchgeführt. und es können Katalyten, wie Kupfer oder Kupferverbindungen, zugesetzt werden. Fer ner kann man sowohl in Gegenwart. als auch in Abwesenheit von Lösungs- oder Verdün nungsmitteln arbeiten.
<I>Beispiel:</I> 2 Teile 3. 3' . 4. 4'-Tetrachlorindanthren. 2 Teile 1-Aminoanthrachinon, 0,4 Teile Kupferoxyd, 1,5 Teile Natriumacetat und 2,0 Teile Nitrobenzol werden miteinander während mehreren Stunden gekocht. Das Ge misch wird filtriert, mit Nitrobenzol und Methylalkohol ausgewaschen und getrocknet. Anorganische Salze werden durch Auskochen mit Wasser, Filtrieren, Auswaschen mit Wasser und nachheriges Trocknen entfernt. Der Farbstoff ist ein blaues Pulver, das sich in konzentrierter Schwefelsäure mit oliver Farbe löst und färbt Baumwolle aus blaugrüner alkalischer Hydrosulfitküpe in tief blaustichig-grünen Tönen.
Process for the production of an anthraquinone derivative. Research has shown that a-halogen atoms in di-anthraquinone-1. 2. 2 '. 1'-dihydroazines (indanthrenes) are reactive so that they can be exchanged for other groups, for example amino or hydroxyl groups, or substituted amino or hydroxyl groups.
These α-haloindanthrenes can be treated with aminoanthraquinone, ammonia, methylamine or aniline to introduce the amino, methylamino or anilido group. They can also be treated with alcoholates or phenols for the production of hydroxyl, alkoxy and similar derivatives.
If the indanthrenes also have ss-halogen atoms, these are not always attacked. The haloindanthrenes can of course also be used in their azine form.
The subject of the present patent is itun a process for the preparation of an anthraquinone derivative, characterized in that 1 mol. 3. 3 '. 4. 4'-Tetrachloroindanthrene condensed with 2 mol. 1-Aminoanthraquinone.
This reaction can be carried out in the presence of acid deadening agents. and catalysts such as copper or copper compounds can be added. Furthermore, you can both in the present. as well as working in the absence of solvents or thinners.
<I> Example: </I> 2 parts 3. 3 '. 4. 4'-tetrachloroindanthrene. 2 parts of 1-aminoanthraquinone, 0.4 part of copper oxide, 1.5 parts of sodium acetate and 2.0 parts of nitrobenzene are boiled together for several hours. The mixture is filtered, washed with nitrobenzene and methyl alcohol and dried. Inorganic salts are removed by boiling with water, filtering, washing out with water and then drying. The dye is a blue powder that dissolves in concentrated sulfuric acid with an olive color and dyes cotton from a blue-green alkaline hydrosulfite vat in deep bluish-green tones.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB146861X | 1928-11-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH146861A true CH146861A (en) | 1931-05-15 |
Family
ID=10045737
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH146861D CH146861A (en) | 1928-11-28 | 1929-11-23 | Process for the production of an anthraquinone derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH146861A (en) |
-
1929
- 1929-11-23 CH CH146861D patent/CH146861A/en unknown
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