DE90041C - - Google Patents
Info
- Publication number
- DE90041C DE90041C DENDAT90041D DE90041DA DE90041C DE 90041 C DE90041 C DE 90041C DE NDAT90041 D DENDAT90041 D DE NDAT90041D DE 90041D A DE90041D A DE 90041DA DE 90041 C DE90041 C DE 90041C
- Authority
- DE
- Germany
- Prior art keywords
- dinitroanthraquinone
- sulfuric acid
- acid
- anthraquinone
- nitroquinizarin
- 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.)
- Active
Links
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 9
- 239000004327 boric acid Substances 0.000 claims description 5
- RZVHIXYEVGDQDX-UHFFFAOYSA-N Anthraquinone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 RZVHIXYEVGDQDX-UHFFFAOYSA-N 0.000 claims description 4
- KGBXLFKZBHKPEV-UHFFFAOYSA-N Boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 4
- IOVCWXUNBOPUCH-UHFFFAOYSA-N nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000011780 sodium chloride Substances 0.000 claims description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M Sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 7
- 235000010288 sodium nitrite Nutrition 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- NMNSBFYYVHREEE-UHFFFAOYSA-N 1,2-dinitroanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C([N+]([O-])=O)C([N+](=O)[O-])=CC=C3C(=O)C2=C1 NMNSBFYYVHREEE-UHFFFAOYSA-N 0.000 description 2
- GUEIZVNYDFNHJU-UHFFFAOYSA-N 1,4-Dihydroxyanthraquinone Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=CC=C2O GUEIZVNYDFNHJU-UHFFFAOYSA-N 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 229960000583 Acetic Acid Drugs 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- -1 amido compound Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 1
- UPKAWFACSJWKND-ZXFFUEEESA-J tetrasodium;(6E)-4-amino-6-[[4-[4-[(2Z)-2-(8-amino-1-oxo-5,7-disulfonatonaphthalen-2-ylidene)hydrazinyl]-3-methoxyphenyl]-2-methoxyphenyl]hydrazinylidene]-5-oxonaphthalene-1,3-disulfonate Chemical compound [Na+].[Na+].[Na+].[Na+].C\1=CC2=C(S([O-])(=O)=O)C=C(S([O-])(=O)=O)C(N)=C2C(=O)C/1=N/NC(C(OC)=C1)=CC=C1C1=CC=C(N\N=C\2C(C3=C(N)C(=CC(=C3C=C/2)S([O-])(=O)=O)S([O-])(=O)=O)=O)C(OC)=C1 UPKAWFACSJWKND-ZXFFUEEESA-J 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Coloring (AREA)
- Treatment Of Fiber Materials (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
In der Patentschrift Nr. 81245 (Zusatz zu Nr. 79768) wurde gezeigt, dafs das Anthrachinon leicht und glatt in Chinizarin übergeführt wird, wenn man es in schwefelsaurer Lösung mit Natriumnitrit und Borsäure behandelt. In the patent specification No. 81245 (addition to No. 79768) it was shown that the anthraquinone is easily and smoothly converted into quinizarin if it is treated in a sulfuric acid solution with sodium nitrite and boric acid.
Wenn man an Stelle des Anthrachinons das von Römer beschriebene 1 · 4'~o-Dinitroanthrächinon (Ber. XVI, S. 363) verwendet, so bildet sich in ebenso leichter und glatter Weise a - Nitrochinizarin.If, instead of the anthraquinone, the 1 · 4 '~ o-dinitroanthraquinone described by Römer (Ber. XVI, p. 363) is used, a -nitroquinizarin is formed just as easily and smoothly.
ι ο kg ι -^'-Dinitroanthrachinon,
200 - Schwefelsäure 66° B.
5 - Natriumnitrit,
8 - Borsäureι ο kg ι - ^ '- Dinitroanthraquinone,
200 - sulfuric acid 66 ° B.
5 - sodium nitrite,
8 - boric acid
werden auf 200 bis 2100C. erhitzt, bis die Schmelze intensiv roth geworden ist und eine in Wasser gegossene Probe sich in Alkalien blau löst. Nach dem Erkalten giefst man in Wasser, wobei sich hellrothe Flocken ausscheiden, kocht auf und filtrirt. Durch alkalisches Filtriren wird das gebildete Nitrochinizarin vom unveränderten Dinitroanthrachinon getrennt. Durch Umkrystallisiren aus Eisessig erhält man es in rothen Krystallen, die bei 244 bis 245 ° schmelzen.are heated to 200 to 210 ° C. until the melt has turned intensely red and a sample poured into water dissolves blue in alkalis. After cooling, it is poured into water, whereupon light red flakes separate out, boiled and filtered. The nitroquinizarin formed is separated from the unchanged dinitroanthraquinone by alkaline filtration. By recrystallizing it from glacial acetic acid, it is obtained in red crystals which melt at 244 ° to 245 °.
Die schwefelsaure Lösung ist rosaroth, zeigt geringe Fluorescenz und ein schwaches Spektrum. Auf Zusatz von Borsäure zeigt die Lösung eine prachtvoll gelborange Fluorescenz und ein scharfes Spektrum, das gegen das des Chinizarins verschoben ist. In Natronlauge löst sich der Körper mit rein blauer Farbe. Die Analyse ergab folgende Resultate:The sulfuric acid solution is pink-red, shows low fluorescence and a weak spectrum. When boric acid is added, the solution shows a splendid yellow-orange fluorescence and a sharp spectrum shifted from that of quinizarin. Dissolves in caustic soda the body with pure blue color. The analysis gave the following results:
Gefunden: C: 58,51; H: 2,75; JV: 5,i6°/0;Found: C: 58.51; H: 2.75; JV: 5.16 ° / 0 ;
Berechnet für Nitrochinizarin : C : 58,91;Calculated for nitroquinizarin: C: 58.91;
i/:2,45; IV:4,9>%- . ■ .i /: 2.45 ; IV: 4.9>% -. ■.
. Nach seiner Entstehungsweise besitzt der Körper höchstwahrscheinlich folgende Constitution :. According to the way it was formed, the body most likely has the following constitution :
NO2 OHNO 2 OH
1 CO, 1 CO,
OH.OH.
Die Verbindung färbt nicht, sie läfst sich leicht zu einer Amidoverbindung reduciren. An Stelle der im Beispiele angeführten Schwefelsäure von 66° B. kann man auch Monohydrat oder schwach rauchende Schwefelsäure anwenden. Man kann ferner direct vom Anthrachinon ausgehen, indem man es in be-The compound does not color; it can easily be reduced to an amido compound. Instead of the sulfuric acid of 66 ° B. given in the example, monohydrate or weakly fuming sulfuric acid can also be used use. Furthermore, one can start directly from the anthraquinone by
kannter Weise in- schwefelsaurer Lösung in Dinitroanthrächinon überführt und dann ■ das Nitrirungsgemisch direct mit Natriumnitrit und Borsäure versetzt und erwärmt. An Stelle des Natriumnitrits kann man andere Salze der . salpetrigen Säure oder diese selbst verwenden.converted in a known manner insulphuric acid solution into dinitroanthraquinone and then ■ that Sodium nitrite and boric acid are added directly to the nitrate mixture and heated. Instead of Sodium nitrite can be used with other salts. Use nitrous acid or yourself.
Das α - Nitrochinizarin soll zur DarstellungThe α-nitroquinizarin is said to be used for illustration
von Farbstoffen dienen.serve of dyes.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE90041C true DE90041C (en) |
Family
ID=361803
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT90041D Active DE90041C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE90041C (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2587093A (en) * | 1949-04-13 | 1952-02-26 | Ici Ltd | Process for the manufacture of polycyclic quinones which carry a nitro and a hydroxy group as nuclear substituents |
| US3031466A (en) * | 1957-09-25 | 1962-04-24 | Ici Ltd | Manufacture of substituted polycyclic quinones |
-
0
- DE DENDAT90041D patent/DE90041C/de active Active
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2587093A (en) * | 1949-04-13 | 1952-02-26 | Ici Ltd | Process for the manufacture of polycyclic quinones which carry a nitro and a hydroxy group as nuclear substituents |
| US3031466A (en) * | 1957-09-25 | 1962-04-24 | Ici Ltd | Manufacture of substituted polycyclic quinones |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE90041C (en) | ||
| DE2134518C3 (en) | Process for the preparation of compounds of the benzothloxanthene series | |
| DE927140C (en) | Process for the fractionation of starch | |
| DE2016862C3 (en) | Process for the preparation of I to 1 and I to 2 metal complex azo dyes | |
| DE373976C (en) | Process for the preparation of aminophenanthrenequinones | |
| DE114974C (en) | ||
| DE83055C (en) | ||
| DE625759C (en) | Process for the preparation of 1,4-diaminoanthraquinone | |
| DE512235C (en) | Process for the preparation of azine derivatives | |
| DE125134C (en) | ||
| DE152689C (en) | ||
| DE528063C (en) | Process for the production of Kuepen dyes | |
| DE1108355B (en) | Process for the preparation of water-insoluble azo dyes | |
| DE62574C (en) | Process for the preparation of new red basic dyes of the triphenylmethane] series | |
| DE643608C (en) | Process for the preparation of polyoxy compounds of the dibenzanthrone series | |
| DE172733C (en) | ||
| DE647014C (en) | Process for the production of water-soluble leuco compounds | |
| DE649044C (en) | Process for the production of azo dyes | |
| DE77226C (en) | Process for the preparation of indulines alkylated on the azine nitrogen | |
| DE557246C (en) | Process for the preparation of sulfoanthracene carboxylic acids | |
| DE706461C (en) | Method for making a naphthalene cap | |
| DE132424C (en) | ||
| DE84505C (en) | ||
| DE133686C (en) | ||
| DE544998C (en) | Process for the preparation of mixed halogenated dyes of the 4íñ5íñ8íñ9-dibenzpyrenquinone series |