DE62531C - Process for the preparation of 'Oxidationsproducten of alizarin and its analogues as well as sulfuric acid ethers of the same. I. - Google Patents
Process for the preparation of 'Oxidationsproducten of alizarin and its analogues as well as sulfuric acid ethers of the same. I.Info
- Publication number
- DE62531C DE62531C DENDAT62531D DE62531DA DE62531C DE 62531 C DE62531 C DE 62531C DE NDAT62531 D DENDAT62531 D DE NDAT62531D DE 62531D A DE62531D A DE 62531DA DE 62531 C DE62531 C DE 62531C
- Authority
- DE
- Germany
- Prior art keywords
- sulfuric acid
- alizarin
- acid
- preparation
- analogues
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 title claims description 22
- RGCKGOZRHPZPFP-UHFFFAOYSA-N Alizarin Chemical compound C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1 RGCKGOZRHPZPFP-UHFFFAOYSA-N 0.000 title claims description 14
- -1 sulfuric acid ethers Chemical class 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims 3
- 239000000975 dye Substances 0.000 claims description 10
- NEIMTOOWBACOHT-UHFFFAOYSA-N Rufigallol Chemical compound O=C1C2=C(O)C(O)=C(O)C=C2C(=O)C2=C1C=C(O)C(O)=C2O NEIMTOOWBACOHT-UHFFFAOYSA-N 0.000 claims description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 150000007513 acids Chemical class 0.000 claims description 6
- 238000009835 boiling Methods 0.000 claims description 5
- AKEJUJNQAAGONA-UHFFFAOYSA-N Sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims description 4
- 230000003647 oxidation Effects 0.000 claims description 4
- 238000007254 oxidation reaction Methods 0.000 claims description 4
- 235000011121 sodium hydroxide Nutrition 0.000 claims description 3
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 claims description 3
- 150000004345 1,2-dihydroxyanthraquinones Chemical class 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- BBNQQADTFFCFGB-UHFFFAOYSA-N 1,2,4-Trihydroxyanthraquinone Chemical compound C1=CC=C2C(=O)C3=C(O)C(O)=CC(O)=C3C(=O)C2=C1 BBNQQADTFFCFGB-UHFFFAOYSA-N 0.000 claims 1
- AHKDJQYHVWSRLT-UHFFFAOYSA-N anthragallol Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=C(O)C(O)=C2O AHKDJQYHVWSRLT-UHFFFAOYSA-N 0.000 claims 1
- 150000002170 ethers Chemical class 0.000 claims 1
- 239000000047 product Substances 0.000 description 7
- VBHKTXLEJZIDJF-UHFFFAOYSA-N Quinalizarin Chemical compound C1=CC(O)=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1O VBHKTXLEJZIDJF-UHFFFAOYSA-N 0.000 description 3
- 240000000358 Viola adunca Species 0.000 description 1
- 235000005811 Viola adunca Nutrition 0.000 description 1
- 235000013487 Viola odorata Nutrition 0.000 description 1
- 235000002254 Viola papilionacea Nutrition 0.000 description 1
- 210000002268 Wool Anatomy 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 230000001264 neutralization Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002035 prolonged Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/02—Hydroxy-anthraquinones; Ethers or esters thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
von Schwefelsäureäthern derselben.of sulfuric acid ethers of the same.
I. Die im Haupt-Patent genannten Farbstoffe der Alizarinreihe können mit ähnlichem Erfolge auch durch die Rufigallussäure ersetzt werden.I. The dyes of the alizarin series mentioned in the main patent can be used with similar success can also be replaced by rufigallic acid.
Unterwirft man Rufigallussäure der Einwirkung von rauchender Schwefelsäure von 70 bis 80 pCt. Anhydridgehalt bei niedriger Temperatur und verfährt im Uebrigen genau nach den Angaben des Haupt-Patentes, so erhält man einen neuen Farbstoff, entgegen den Angaben von Klobukowski (Berichte IX, 1256), wonach Rufigallussäure durch Schwefelsäureanhydrid nicht verändert werden soll. Hierbei erzielt man insofern einen bedeutenden technischen Effect, als das neue Product ein sehr kräftiger Farbstoff ist, der z. B. auf chromirter Wolle bordeauxbraune Töne liefert, während bekanntlich Rufigallussäure nur schwach färbt und als Farbstoff überhaupt keinen Werth hat. Die Lösung des neuen Farbstoffes in concentrirter Schwefelsäure ist violett, während die Lösung der Rufigallussäure darin roth ist.If one subjects rufigallic acid to the action of fuming sulfuric acid from 70 to 80 pct. Anhydride content at low temperature and otherwise proceeds exactly According to the information in the main patent, a new dye is obtained, contrary to the Information from Klobukowski (Reports IX, 1256), according to which rufigallic acid is replaced by sulfuric anhydride should not be changed. Here one achieves a significant technical effect insofar as the new product is a is very strong dye that z. B. supplies burgundy-brown tones on chromed wool, while rufigallic acid is known to be weak colors and has absolutely no value as a dye. The solution of the new dye in concentrated sulfuric acid is violet, while the solution of rufigallic acid in it is red.
Zur Darstellung des neuen Productes verfährt man ganz nach dem Verfahren des Haupt-Patentes, indem man an Stelle von Alizarin Rufigallussäure verwendet. Auch hier läfst sich die Bildung eines beizenfärbenden Zwischenproductes nachweisen, welches als der Schwefelsäureäther des Rufigallussäurebordeaux' aufzufassen ist und welches sich leicht isoliren läfst, wenn man die Schmelze unter Vermeidung von Temperaturerhöhung auf Eis giefst und den entstehenden Niederschlag abfiltrirt.To represent the new product one proceeds entirely according to the procedure of the main patent, by using rufigallic acid in place of alizarin. Here, too, works prove the formation of an intermediate product which stains the stain, which is called sulfuric acid ether of rufigallic acid Bordeaux and which is easy to isolate, if the melt is poured onto ice while avoiding an increase in temperature and the precipitate formed is filtered off.
II. In dem Haupt - Patent No. 60855 sind sogen. Zwischenproducte beschrieben, welche man durch Einwirkung von hochprocentiger rauchender Schwefelsäure auf Alizarin oder alizarinähnliche Farbstoffe bei niedriger Temperatur erhält und welche als die neutralen Schwefeläureäther der Oxydationsproducte des Alizarins und seiner Analogen anzusehen sind. Durch successive Behandlung mit Natronlauge und Kochen mit Säuren gehen diese Schwefelsäureäther, wie im Haupt-Patente weiter nachgewiesen ist, in die entsprechenden PoIyoxanthrachinone über, welche mit dem Namen Alizarinbordeaux' bezeichnet worden sind. Dieser Uebergang kann auch durch Erhitzen der Zwischenproducte mit Säuren erfolgen; zur Erläuterung dieses Verfahrens diene nachträglich noch folgendes Beispiel:II. In the main patent no. 60855 are so-called Intermediate products described which one by the action of high percentage fuming sulfuric acid on alizarin or Alizarin-like dyes obtained at low temperature and which than the neutral ones Sulfuric acid ethers of the oxidation products of alizarin and its analogues are to be regarded. Through successive treatment with caustic soda and boiling with acids, these sulfuric acid ethers as further demonstrated in the main patents, into the corresponding polyoxanthraquinones about which have been designated by the name Alizarinbordeaux '. This transition can also take place by heating the intermediate products with acids; The following example can be used to explain this procedure:
Das nach dem Haupt - Patent aus ι ο kg Alizarin erhaltene Zwischenproduct (Schwefelsäureäther) wird mit 100 kg Schwefelsäure von 600B. so lange auf 1700C. erhitzt, bis eine in concentrirte Schwefelsäure gegossene Probe die blauviolette Farbe der Schwefelsäurelösung des Alizarinbordeaux' zeigt. Alsdann wird in Wasser gegossen, aufgekocht, der abgeschiedene Farbstoff abfiltrirt und ausgewaschen. ·The intermediate product obtained according to the main patent from ι ο kg of alizarin (sulfuric acid ether) is heated with 100 kg of sulfuric acid from 60 ° B. to 170 ° C. until a sample poured into concentrated sulfuric acid has the blue-violet color of the sulfuric acid solution of the alizarin Bordeaux ' shows. Then it is poured into water, boiled, the deposited dye is filtered off and washed out. ·
Auch durch anhaltendes Kochen mit verdünnten Säuren lassen sich die Schwefelsäure-The sulfuric acid can also be reduced by prolonged boiling with dilute acids.
äther des Alizarinbordeaux' und seiner Analogen in die Bordeaux' selbst überführen.äther des Alizarinbordeaux 'and its analogues in the Bordeaux' itself.
Claims (2)
Verfahren zur Darstellung neuer Farbstoffe der Alizarinreihe, darin bestehend, dafs man die Schwefelsäureäther der Oxydationsproducte des Alizarins, Purpurins, Flavopurpurins, Anthrapurpurins, Anthragallols und der Rufigallussäure, wie sie nach dem durch Anspruch 1. des Haupt-Patentes und Anspruch 1. dieses Patentes geschützten Verfahren zu erhalten sind, anstatt sie in Älkalilauge zu lösen und dann mit Säuren zu zersetzen, entweder durch Kochen mit. verdünnten Säuren oder durch Erhitzen mit Schwefelsäure von 600B. auf 160 bis i8o° C. in die neuen Farbstoffe überführt.2. A method for converting the sulfuric acid ether which can be represented by the method protected by claim 1 into a new oxidation product, consisting in that. this ether is heated with acids or dissolved in alkaline lye and the solution is decomposed by boiling with acid.
Process for the preparation of new dyes of the alizarin series, consisting in that the sulfuric acid ethers of the oxidation products of alizarine, purpurine, flavopurpurine, anthrapurpurine, anthragallic acid and rufigallic acid, as protected by claim 1 of the main patent and claim 1 of this patent Methods to obtain are instead of dissolving them in caustic soda and then decomposing them with acids, either by boiling them with. dilute acids or transferred by heating with sulfuric acid of 60 to 160 to 0 B. i8o ° C. The novel dyes.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE62531C true DE62531C (en) |
Family
ID=336512
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT62531D Expired - Lifetime DE62531C (en) | Process for the preparation of 'Oxidationsproducten of alizarin and its analogues as well as sulfuric acid ethers of the same. I. |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE62531C (en) |
-
0
- DE DENDAT62531D patent/DE62531C/en not_active Expired - Lifetime
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