AT42716B - Process for the preparation of new anthraquinone derivatives. - Google Patents
Process for the preparation of new anthraquinone derivatives.Info
- Publication number
- AT42716B AT42716B AT42716DA AT42716B AT 42716 B AT42716 B AT 42716B AT 42716D A AT42716D A AT 42716DA AT 42716 B AT42716 B AT 42716B
- Authority
- AT
- Austria
- Prior art keywords
- preparation
- anthraquinone derivatives
- anthraquinone
- derivatives
- new anthraquinone
- Prior art date
Links
- 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 title claims description 8
- 150000004056 anthraquinones Chemical class 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 13
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims 1
- 229960000583 acetic acid Drugs 0.000 description 4
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- RBOXVHNMENFORY-UHFFFAOYSA-N 9-methoxy-3-methyl-2,4,4a,5,6,7,7a,13-octahydro-1h-4,12-methanobenzofuro[3,2-e]isoquinoline-7-ol Chemical compound C1C(N(CCC234)C)C2CCC(O)C3OC2=C4C1=CC=C2OC RBOXVHNMENFORY-UHFFFAOYSA-N 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- QFFVPLLCYGOFPU-UHFFFAOYSA-N barium chromate Chemical compound [Ba+2].[O-][Cr]([O-])(=O)=O QFFVPLLCYGOFPU-UHFFFAOYSA-N 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229910000043 hydrogen iodide Inorganic materials 0.000 description 1
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
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Verfahren zur Darstellung von neuen Anthrachinonderivaten.
In dem Patente Nr. 41809 wurden neue Reduktionsprodukte des Anthrachinons nnd seiner Derivate beschrieben. Diese Reduktionsprodukte wurden als Dianthranole erkannt.
Wie schon in dem genannten Patent kurz erwähnt, gehen die Dianthranole durch gemässigte
EMI1.1
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vorstellen.
Für die Oxydation kommen die meisten der gebräuchlichen Oxydationsmittel in
Betracht, z. B. Eisenchlorid in essigsaurer Lösung, alkalische Chlorkalk- oder Permanganat- lösung usw. Mit Chromsäure in essigsaurer Lösung gekocht, geben diese Dichinone Anthrachinon, bezw. seine Derivate.
386 Gewichtsteile des nach Patent Nr. 41809 erhaltenen Anthrachinonrednktions-
EMI1.3
wichtsteile) gelöst und in eine Schüttelflasche eingefüllt. Anstatt dessen kann man auch direkt die bei dem Verfahren des oben erwähnten Patentes erhaltene, vom Reduktions-
EMI1.4
unter Ausscheidung von Braunstein entfärbt wird, bis die rote Farbe des Permangallats dauernd bestehen bleibt. bel dieser Oxydation wird das alkatiosliche Ausgangsmaterial in einen alkaliunlöslichen Körper überführt, der von dem Braunstein umhüllt wird. Zur Isolierung des ersteren wird daher mit einem Überschuss von Bisulfit versetzt, welches den Braunstein bekanntlich löst, den neuen Körper dagegen nicht angreift.
Sobald also die braune Farbe in ein lichtes Gelbgrün umgeschlagen hat und ein weiterer Zusatz von
Bisulfit die Farbnuanco nicht mein-ändert, nitriert man ab, trocknet und krystallisiert aus sehr viel Eisessig, Azetophenon oder Tetrachloraothan um.
@ Das entstandene Dichinon krystallisiert in reinem Zustande in zitronengelben, derben
Kryställchen, welche gegen 300 C sich schwärzen, aber erst bei viel höherer Temperatur schmelzen. In konzentrierter Schwefelsäure löst sich der Körper mit bordeauxroter Farbe.
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In organischen Lösungsmitteln, ist er schwer löslich, die Lösungen sind in der'Hitze intensiv grün gefärbt. Zerdrückt oder presst man die Krystalle, so geht die Farbe des Pulvers von Gelb in Grün über, um nach kurzer Zeit wieder gelb zu worden. Energische Reduktion mit Jodwasserstoff und Phosphor führt zum Anthrazendihydrin, gelinde Reduktion führt wieder zum Dianthranot zurück. Die Oxydation mit Chromsäure und Eisessig gibt Anthrachinon.
<Desc / Clms Page number 1>
Process for the preparation of new anthraquinone derivatives.
New reduction products of anthraquinone and its derivatives were described in the patent No. 41809. These reduction products were recognized as dianthranols.
As mentioned briefly in the patent mentioned, the dianthranols are moderate
EMI1.1
EMI1.2
imagine.
Most of the common oxidizing agents are used for the oxidation
Consideration, e.g. B. iron chloride in acetic acid solution, alkaline chlorinated lime or permanganate solution, etc. Cooked with chromic acid in acetic acid solution, these give dichinones anthraquinone, respectively. its derivatives.
386 parts by weight of the anthraquinone reduction obtained according to Patent No. 41809
EMI1.3
parts) and poured into a shake bottle. Instead of this, one can also directly use the method obtained in the above-mentioned patent from the reduction
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is decolorized with precipitation of brownstone until the red color of the permangallate persists. During this oxidation, the alkaline starting material is converted into an alkali-insoluble body which is surrounded by the manganese dioxide. To isolate the former, an excess of bisulfite is therefore added, which, as is known, dissolves the manganese dioxide but does not attack the new body.
So as soon as the brown color has turned into a light yellow-green and another addition of
Bisulfite, which does not change the color nuanco, is nitrated, dried and crystallized from a lot of glacial acetic acid, acetophenone or tetrachloraothane.
@ The resulting dichinone crystallizes in a pure state into lemon-yellow, coarse
Crystals which blacken towards 300 C, but only melt at a much higher temperature. The body dissolves in concentrated sulfuric acid with a claret-red color.
<Desc / Clms Page number 2>
It is sparingly soluble in organic solvents, the solutions are colored intensely green in the heat. If the crystals are crushed or pressed, the color of the powder changes from yellow to green, only to turn yellow again after a short time. Energetic reduction with hydrogen iodide and phosphorus leads to anthracene dihydrin, mild reduction leads back to dianthranot. Oxidation with chromic acid and glacial acetic acid gives anthraquinone.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT42716T | 1908-05-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT42716B true AT42716B (en) | 1910-06-25 |
Family
ID=3561846
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT42716D AT42716B (en) | 1908-05-25 | 1908-05-25 | Process for the preparation of new anthraquinone derivatives. |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT42716B (en) |
-
1908
- 1908-05-25 AT AT42716D patent/AT42716B/en active
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