AT46294B - Process for the preparation of benzoylaminoanthraquinones and their derivatives. - Google Patents
Process for the preparation of benzoylaminoanthraquinones and their derivatives.Info
- Publication number
- AT46294B AT46294B AT46294DA AT46294B AT 46294 B AT46294 B AT 46294B AT 46294D A AT46294D A AT 46294DA AT 46294 B AT46294 B AT 46294B
- Authority
- AT
- Austria
- Prior art keywords
- derivatives
- preparation
- benzoylaminoanthraquinones
- parts
- benzamide
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 3
- KOJOUCAVSDKDPR-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)benzamide Chemical class C=1C=CC=2C(=O)C3=CC=CC=C3C(=O)C=2C=1NC(=O)C1=CC=CC=C1 KOJOUCAVSDKDPR-UHFFFAOYSA-N 0.000 title description 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 8
- 150000001555 benzenes Chemical class 0.000 claims description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000000984 vat dye Substances 0.000 description 2
- BTJMOXDWIPVCRO-UHFFFAOYSA-N 2,3,4-trimethoxybenzamide Chemical compound COC1=CC=C(C(N)=O)C(OC)=C1OC BTJMOXDWIPVCRO-UHFFFAOYSA-N 0.000 description 1
- -1 B. toluylamide Chemical class 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical class [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- FNCVZYRPXOZNSM-UHFFFAOYSA-N n-(4-chloro-9,10-dioxoanthracen-1-yl)benzamide Chemical compound C1=2C(=O)C3=CC=CC=C3C(=O)C=2C(Cl)=CC=C1NC(=O)C1=CC=CC=C1 FNCVZYRPXOZNSM-UHFFFAOYSA-N 0.000 description 1
- OARRHUQTFTUEOS-UHFFFAOYSA-N safranin Chemical compound [Cl-].C=12C=C(N)C(C)=CC2=NC2=CC(C)=C(N)C=C2[N+]=1C1=CC=CC=C1 OARRHUQTFTUEOS-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
<Desc/Clms Page number 1>
Verfahren zur Darstellung von Benzoylaminoanthrachinonen und deren Derivaten.
EMI1.1
Es wurde gefunden, dass man zu den als wertvolle Küpenfarbstoffe überaus wichtigen Benyolamynoantrachinonverbindungen gelangen kann, wenn man Benzamid (bezw. seine Analoge) mit Halogenanthrachinonen oder deren Derivaten, welche also ausser Halogenatomen noch andere Gruppen, wie Hydroxyl, Amido, Methyl etc. enthalten, unter Zusatz eines säurobindenden Mittels, zweckmässig bei Gegenwart von Kontaktsubstanzen, wie Kupfersalzen, erhitzt.
Beispiel.
10 Teile α-Bromanthrachinon werden mit 20 Teilen Benzamid und 30 Teilen Nitrobenzol unter Zusatz von 10 Teilen entwässertem Natriumazetat und 0'5 Teilen Kupferchlorid gekocht, bis kein unverändertes Bromanthrachinon mehr nachzuweisen ist. Man vordünnt die Schmelze mit dem gleichen Volumen Alkohol, saugt die abgeschiedenen Kristalle ab und wäscht aus. Man erhält so das Benzoyl-x-aminoanthrachinon, welches ein gelber Küpenfarbstoff ist.
Ebenso verhalten sich die Dihalogenanthrachinone und die substituierten llalogen- anthrachinone, z. B. Benzoylamino-4-chloranthrachinon liefert das Baumwolle rot färbende 1. 4-Dibenzoyldiam inoan thrachinon.
An Stelle des Benzamids kann man auch dessen im Benzolkern substituierte Derivato anwenden, z. B. Toluylamid, Trimethoxybcnzamid.
**WARNUNG** Ende DESC Feld kannt Anfang CLMS uberlappen**.
<Desc / Clms Page number 1>
Process for the preparation of benzoylaminoanthraquinones and their derivatives.
EMI1.1
It has been found that the benyolamynoanthraquinone compounds, which are extremely important as valuable vat dyes, can be obtained by using benzamide (or its analogues) with haloanthraquinones or their derivatives, which contain other groups such as hydroxyl, amido, methyl, etc. in addition to halogen atoms, with the addition of an acid-binding agent, expediently in the presence of contact substances such as copper salts, heated.
Example.
10 parts of α-bromoanthraquinone are boiled with 20 parts of benzamide and 30 parts of nitrobenzene with the addition of 10 parts of dehydrated sodium acetate and 0.5 parts of copper chloride until no more unchanged bromanthraquinone can be detected. The melt is pre-thinned with the same volume of alcohol, the separated crystals are sucked off and washed out. The benzoyl-x-aminoanthraquinone, which is a yellow vat dye, is obtained in this way.
The Dihalogenanthraquinones and the substituted llalogen- anthraquinones behave in the same way, eg. B. Benzoylamino-4-chloroanthraquinone supplies the cotton-red 1. 4-Dibenzoyldiaminoan throquinone.
Instead of the benzamide one can also use its derivative substituted in the benzene nucleus, e.g. B. toluylamide, trimethoxybenzamide.
** WARNING ** End of DESC field may overlap beginning of CLMS **.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE46294X | 1908-11-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT46294B true AT46294B (en) | 1911-02-10 |
Family
ID=5625252
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT46294D AT46294B (en) | 1908-11-16 | 1909-08-30 | Process for the preparation of benzoylaminoanthraquinones and their derivatives. |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT46294B (en) |
-
1909
- 1909-08-30 AT AT46294D patent/AT46294B/en active
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