CH183885A - Process for the production of an anthraquinone derivative. - Google Patents
Process for the production of an anthraquinone derivative.Info
- Publication number
- CH183885A CH183885A CH183885DA CH183885A CH 183885 A CH183885 A CH 183885A CH 183885D A CH183885D A CH 183885DA CH 183885 A CH183885 A CH 183885A
- Authority
- CH
- Switzerland
- Prior art keywords
- leuco
- anthraquinone derivative
- production
- derivative
- mol
- Prior art date
Links
- 238000000034 method 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 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 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 description 3
- 150000004056 anthraquinones Chemical class 0.000 description 3
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WGOXABJBDOYQFK-UHFFFAOYSA-N 1,4-diaminoanthracene-9,10-diol Chemical compound C1=CC=C2C(O)=C3C(N)=CC=C(N)C3=C(O)C2=C1 WGOXABJBDOYQFK-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen 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 Anthraehinonderivates. Im Hauptpatent ist ein Verfahren zur Herstellung eines wertvollen Anthrachinon- derivates beschrieben, bei dem eine Mischung aus etwa äquimolekularen Mengen von Leuko- 1.4- diaminoanthrachinon, Monomethylamin und Monoäthanolamin bei Gegenwart eines Verdünnungsmittels so lange erhitzt wird, bis kein Leuko-1.4-diamirro-anthrachinorr mehr nachzuweisen ist,
worauf die entstandene Verbindung oxydiert wird.
Es wurde nun gefunden, dass man ein ebenfalls wertvolles Anthrachinonderivat er halten kann, wenn man 1 Mol Leuko-1.4.5- triaminoanthrachinon mit 2 Mol Monomethyl- amin beiGegenwarteinesVerdünnungamittels, wie Wasser, Alkohole oder Chlorbenzole, so lange erhitzt, bis kein Leuko-1.4.5-triamino- anthrachinon mehr nachzuweisen ist, worauf die entstandene Verbindung oxydiert wird.
Das erhaltene Anthrachinonderivat liefert auf Acetatseide marineblaue Färbungen. Beispiel: 12,3 Teile Leuko-1.4.5-triaminoanthra- chinon und<B>16</B> Teile einer 25 o/oigen wässe- rigen Monomethylaminlösung werden in 130 Teilen Methanol so lange unter Rühren zum Sieden erhitzt, bis kein Lerrko-1.4.5-triamirro- anthrachinon mehr nachzuweisen ist.
Man setzt sodann 0,5 Teile Kupferacetat und S Teile Piperidin zu und leitet so lange Luft oder Sauerstoff durch die Mischung, bis die Oxy dation beendet ist. Darauf lässt man abkühlen, saugt den ausgeschiedenen Rückstand ab und wäscht ihn mit Methanol und Wasser aus.
Process for the preparation of an anthraquinone derivative. The main patent describes a process for the preparation of a valuable anthraquinone derivative, in which a mixture of approximately equimolecular amounts of leuco 1,4-diaminoanthraquinone, monomethylamine and monoethanolamine is heated in the presence of a diluent until no leuco-1,4-diamirro-anthraquinorr more is to be proven,
whereupon the resulting compound is oxidized.
It has now been found that an equally valuable anthraquinone derivative can be obtained if 1 mole of leuco-1.4.5-triaminoanthraquinone with 2 moles of monomethylamine in the presence of a diluent, such as water, alcohol or chlorobenzenes, is heated until no leuco-1.4 .5-triamino-anthraquinone can be detected more, whereupon the resulting compound is oxidized.
The anthraquinone derivative obtained gives navy blue colorations on acetate silk. Example: 12.3 parts of leuco-1,4.5-triaminoanthraquinone and 16 parts of a 25% aqueous monomethylamine solution in 130 parts of methanol are heated to boiling with stirring until no Lerrko -1.4.5-triamirro-anthraquinone can be detected more.
Then 0.5 parts of copper acetate and 5 parts of piperidine are added and air or oxygen is passed through the mixture until the oxidation has ended. It is then allowed to cool, the precipitated residue is filtered off with suction and washed out with methanol and water.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE183885X | 1933-09-19 | ||
| CH176930T | 1934-09-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH183885A true CH183885A (en) | 1936-04-30 |
Family
ID=25719917
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH183885D CH183885A (en) | 1933-09-19 | 1934-09-07 | Process for the production of an anthraquinone derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH183885A (en) |
-
1934
- 1934-09-07 CH CH183885D patent/CH183885A/en unknown
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