CH133701A - Process for the preparation of an oxidation product of an anthraquinone derivative. - Google Patents
Process for the preparation of an oxidation product of an anthraquinone derivative.Info
- Publication number
- CH133701A CH133701A CH133701DA CH133701A CH 133701 A CH133701 A CH 133701A CH 133701D A CH133701D A CH 133701DA CH 133701 A CH133701 A CH 133701A
- Authority
- CH
- Switzerland
- Prior art keywords
- red
- strong
- green
- blue
- product
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 8
- 230000003647 oxidation Effects 0.000 title claims description 5
- 238000007254 oxidation reaction Methods 0.000 title claims description 5
- 238000002360 preparation 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
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 10
- 239000000047 product Substances 0.000 claims description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- 239000007800 oxidant agent Substances 0.000 claims description 5
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 3
- 239000007859 condensation product Substances 0.000 claims description 3
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 3
- 229910017604 nitric acid Inorganic materials 0.000 claims description 3
- ZYECOAILUNWEAL-NUDFZHEQSA-N (4z)-4-[[2-methoxy-5-(phenylcarbamoyl)phenyl]hydrazinylidene]-n-(3-nitrophenyl)-3-oxonaphthalene-2-carboxamide Chemical compound COC1=CC=C(C(=O)NC=2C=CC=CC=2)C=C1N\N=C(C1=CC=CC=C1C=1)/C(=O)C=1C(=O)NC1=CC=CC([N+]([O-])=O)=C1 ZYECOAILUNWEAL-NUDFZHEQSA-N 0.000 claims description 2
- 229920000742 Cotton Polymers 0.000 claims description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 claims description 2
- 239000007900 aqueous suspension Substances 0.000 claims description 2
- 239000004327 boric acid Substances 0.000 claims description 2
- -1 boric acid ester Chemical class 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 239000000975 dye Substances 0.000 claims description 2
- 235000011121 sodium hydroxide Nutrition 0.000 claims description 2
- 238000001228 spectrum Methods 0.000 claims description 2
- 239000000984 vat dye Substances 0.000 claims description 2
- AQXYVFBSOOBBQV-UHFFFAOYSA-N 1-amino-4-hydroxyanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=CC=C2N AQXYVFBSOOBBQV-UHFFFAOYSA-N 0.000 claims 1
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 claims 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Natural products O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 238000009835 boiling Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-N dithionous acid Chemical compound OS(=O)S(O)=O GRWZHXKQBITJKP-UHFFFAOYSA-N 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000000725 suspension Substances 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
- C09B59/00—Artificial dyes of unknown constitution
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines Oxydationsproduktes eines Anthrachinonderivates. In dem Schweizerpatent Nr. 127262 ist ein Verfahren zur Darstellung eines Derivates des nach dem Schweizerpatent Nr. 122590 durch gelinde Oxydation des Kondensations produktes aus 1-Amino-4-oxyanthrachinoci -f- Formaldehyd erhältlichen Produktes beschrie ben. Das Verfahren ist dadurch gekenn zeichnet, dass die Verbindung, wie sie er halten werden kann gemäss dem Verfahren des Schweizerpatentes Nr. 122590, mit Oxy dationsmitteln, zum Beispiel in konzentrierter Schwefelsäure gelöst, behandelt wird.
Es wurde nun gefunden, dass sich das gleiche Produkt wie im Schweizerpatent Nr. 127262 beschrieben, sehr glatt und be quem auch in wässeriger Suspension durch Oxydation des im Schweizerpatent Nr. 122590 beschriebenen Produktes mit geeigneten Oxy dationsmitteln, wie salpetriger Säure oder Salpetersäure bei höherer Temperatur erhalten lässt.
Das bedeutet eine erhebliche Vereinfa chung der Arbeitsweise, da man zum Beispiel die Schmelze der Körper wie sie nach Schweizer patent Nr. 122590 erhalten werden, direkt in Wasser geben und ohne zu isolieren, direkt oxydieren kann. <I>Beispiel 1:</I> Das aus 10 Gewichtsteilen des Konden sationsproduktes aus 1.4-Aminooxyanthra- chinon -j- Formaldehyd gemäss Schweizer patent Nr. 122590 erhaltene Produkt wird in 400 Gewichtsteilen konzentrierter Schwefel säure gelöst, dann in 5000 Gewichtsteile Wasser eingerührt und zum Sieden erhitzt.
Zu der kochenden Suspension werden all- mählich 40-50 Gewichtsteile 77 % ixe Sal- petersäure zugegeben, bis eine abfiltrierte Probe sich in konzentrierter Schwefelsäure violettrot löst, was nach ganz kurzer Zeit der Fall ist.
Beispiel. <I>2:</I> Das wie oben nach dem Schweizerpatent Nr. 122590 erhaltene und in konzentrierter Schwefelsäure gelöste Produkt wird in 5000 Gewichtsteilen Wasser, dem 10 Gewichtsteile Natriumnitrit zugesetzt sind, gegossen und aufgekocht. Die Oxydation ist fast momentan beendet.
Der so erhältliche Körper ist ein kräftiger Küpenfarbstoff von bemerkenswerten Echt heitseigenschaften. Der Farbstoff scheidet kein Formaldehyd mehr ab, löst sich in Schwefelsäure mit violettroter Farbe und liefert einen blaugrünen Borsäureester mit charakteristischem Spektrum, und zwar einer starken Linie im Rot und einer schwächeren an der Grenze von rot und gelb. Mit Reduk tionsmitteln behandelt, geht er in die Hydro- form über, in der er ein grünblaues Pulver darstellt, das in konzentrierter Schwefelsäure mit grüner Farbe löslich ist.
Mit Natronlauge und Hydrosulfit verkiipt, färbt er Baumwolle in rotvioletten Tönen an, die beim Verhängen in ein kräftiges, sehr licht- und waschechtes Blaugrau übergehen.
Process for the preparation of an oxidation product of an anthraquinone derivative. In Swiss patent no. 127262 a process for the preparation of a derivative of the product obtainable from 1-amino-4-oxyanthraquinoci -f- formaldehyde is described according to Swiss patent no. 122590 by gentle oxidation of the condensation product. The method is characterized in that the compound, as it can be obtained according to the method of Swiss Patent No. 122590, is treated with oxidizing agents, for example dissolved in concentrated sulfuric acid.
It has now been found that the same product as described in Swiss Patent No. 127262 is very smooth and comfortable, even in aqueous suspension, by oxidizing the product described in Swiss Patent No. 122590 with suitable oxidizing agents such as nitrous acid or nitric acid at a higher temperature can get.
This means a considerable simplification of the way of working, since, for example, the melt of the body as obtained according to Swiss patent no. 122590 can be put directly into water and oxidized directly without isolating. <I> Example 1: </I> The product obtained from 10 parts by weight of the condensation product of 1,4-aminooxyanthraquinone -j- formaldehyde according to Swiss patent No. 122590 is dissolved in 400 parts by weight of concentrated sulfuric acid, then stirred into 5000 parts by weight of water and heated to the boil.
40-50 parts by weight of 77% ixe nitric acid are gradually added to the boiling suspension until a filtered sample dissolves violet-red in concentrated sulfuric acid, which is the case after a very short time.
Example. <I> 2: </I> The product obtained as above according to Swiss patent no. 122590 and dissolved in concentrated sulfuric acid is poured into 5000 parts by weight of water to which 10 parts by weight of sodium nitrite have been added and boiled. The oxidation is almost over for the moment.
The body obtained in this way is a strong vat dye with remarkable authenticity properties. The dye no longer separates formaldehyde, dissolves in sulfuric acid with a violet-red color and provides a blue-green boric acid ester with a characteristic spectrum, namely a strong line in red and a weaker line at the border between red and yellow. Treated with reducing agents, it changes into the hydroform, in which it is a green-blue powder that is soluble in concentrated sulfuric acid with a green color.
With caustic soda and hydrosulphite, he stains cotton in red-violet tones, which turn into a strong, very light- and washfast blue-gray when hanging.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH127262T | 1926-05-15 | ||
| CH133701T | 1926-05-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH133701A true CH133701A (en) | 1929-06-15 |
Family
ID=25710826
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH133701D CH133701A (en) | 1926-05-15 | 1926-05-15 | Process for the preparation of an oxidation product of an anthraquinone derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH133701A (en) |
-
1926
- 1926-05-15 CH CH133701D patent/CH133701A/en unknown
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