DE267211C - - Google Patents
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- Publication number
- DE267211C DE267211C DENDAT267211D DE267211DA DE267211C DE 267211 C DE267211 C DE 267211C DE NDAT267211 D DENDAT267211 D DE NDAT267211D DE 267211D A DE267211D A DE 267211DA DE 267211 C DE267211 C DE 267211C
- Authority
- DE
- Germany
- Prior art keywords
- carboxylic acids
- parts
- esters
- anthraquinone
- ammonia
- 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.)
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- ASDLSKCKYGVMAI-UHFFFAOYSA-N 9,10-dioxoanthracene-2-carboxylic acid Chemical class C1=CC=C2C(=O)C3=CC(C(=O)O)=CC=C3C(=O)C2=C1 ASDLSKCKYGVMAI-UHFFFAOYSA-N 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 3
- -1 aromatic alcohols Esters Chemical class 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N Nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- SESFRYSPDFLNCH-UHFFFAOYSA-N Benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 229960000583 Acetic Acid Drugs 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- KCXMKQUNVWSEMD-UHFFFAOYSA-N Benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 239000005751 Copper oxide Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- QPLDLSVMHZLSFG-UHFFFAOYSA-N copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 1
- 229910000431 copper oxide Inorganic materials 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
KLASSE Mq. GRUPPECLASS Mq. GROUP
und deren Derivaten.and their derivatives.
Zusatz zum Patent 247411.*)Addition to patent 247411. *)
Patentiert im Deutschen Reiche vom 24. November 1912 ab. Längste Dauer: 4. Januar 1926.Patented in the German Empire on November 24, 1912. Longest duration: January 4, 1926.
Im Patent 256344, Zusatz zum Patent 247411, Kl. 12 q, ist gezeigt, daß die Darstellung von i-Aminoanthrachinon-2-carbonsäuren und deren Derivaten aus in i-Stellung negativ substituierten Anthrachinon-2-carbonsäuren und Ammoniak oder primären oder sekundären Aminoverbindungen besonders glatt verläuft, wenn man die Kondensation mit den Estern der genannten Carbonsäuren ausführt.In patent 256344, addition to patent 247411, Kl. 12 q, it is shown that the preparation of i-aminoanthraquinone-2-carboxylic acids and their Derivatives from negatively substituted in i-position Anthraquinone-2-carboxylic acids and ammonia or primary or secondary amino compounds runs particularly smoothly if the condensation is carried out with the esters of the carboxylic acids mentioned.
Es hat sich nun gezeigt, daß von den Estern der in i-Stellung negativ stubstituierten Anthrachinon-2-carbonsäuren diejenigen aromatischer Alkohole wiederum besondere Vorteile bieten. Diese Ester sind nicht nur selbst auf sehr einfache und billige Weise erhältlich, sondern es zeigen auch die mit ihrer Hilfe hergestellten Kondensationsprodukte die wichtige Eigenschaft, sehr leicht, z. B. schon durch kalte Schwefelsäure, verseift zu werden, wodurch ihre Verwendung unter Umständen sehr vereinfacht wird.It has now been shown that of the esters that are negatively substituted in the i-position Anthraquinone-2-carboxylic acids Those of aromatic alcohols in turn offer particular advantages. These esters aren't just itself available in a very simple and cheap way, but also show those with theirs Help produced condensation products the important property, very easily, z. B. already by cold sulfuric acid, to be saponified, thereby reducing their use under certain circumstances is very simplified.
Eine Mischung von 100 Teilen i-Chloranthrachinon-2-carbonsäurebenzylester (erhältlich beispielsweise durch Kochen von i-chloranthrachinon-2-carbonsaurem Kali mit Benzylchlorid; gelbliche Nadeln vom Schmelzpunkt 135 bis 1360, unlöslich in Wasser, verdünnten Säuren und Alkalien, schwer löslich in kaltem Alkohol, Äther, Eisessig, leicht in kochendem Eisessig und höher siedenden»Lösungsmitteln), 40 Teilen 2 · 5-Dichloranilin, 120 Teilen Nitrobenzol, 30 Teilen geschmolzenem Natriumacetat und 1,5 Teilen Kupferoxyd wird 3 Stunden auf 185 bis 190 ° erhitzt. Nach dem Erkalten verdünnt man mit Alkohol, saugt die ausgeschiedenen roten Kristalle ab und wäscht mit Alkohol und heißem' Wasser. Zur Reinigung kann man den 1 · 2' · s'-Dichlorphenylaminoanthrachinon-2-carbonsäurebenzylester aus Nitrobenzol oder Pyridin Umkristallisieren. Er bildet gelbrote Nadeln und ist unlöslich in Wasser, verdünnten Säuren und Alkalien, schwer löslich in Alkohol und Äther, leichter in Nitrobenzol und Pyridin mit gelbstichig roter Farbe. In kalter Schwefelsäure löst er sich gelb. Aus dieser Lösung wird durch Wasser die freie ι · 2' · 5' - Dichlorphenylaminoanthrachinon - 2-carbonsäure in gelbroten Flocken gefällt. Sie ist im Gegensatz zu ihrem Benzylester in verdünnten Alkalien mit blauroter Farbe löslich. Analog verfährt man bei Benutzung der Ester mit anderen aromatischen Alkoholen und bei der Kondensation mit anderen Aminen oder Ammoniak.A mixture of 100 parts of i-chloranthraquinone-2-carboxylic acid benzyl ester (obtainable, for example, by boiling i-chloranthraquinone-2-carboxylic acid potassium with benzyl chloride; yellowish needles with a melting point of 135 to 136 0 , insoluble in water, dilute acids and alkalis, hardly soluble in cold alcohol, ether, glacial acetic acid, slightly boiling glacial acetic acid and higher-boiling solvents), 40 parts of 2 · 5-dichloroaniline, 120 parts of nitrobenzene, 30 parts of molten sodium acetate and 1.5 parts of copper oxide is heated to 185-190 ° for 3 hours. After cooling, it is diluted with alcohol, the separated red crystals are suctioned off and washed with alcohol and hot water. For purification, the 1 · 2 '· s'-dichlorophenylaminoanthraquinone-2-carboxylic acid benzyl ester can be recrystallized from nitrobenzene or pyridine. It forms yellow-red needles and is insoluble in water, dilute acids and alkalis, sparingly soluble in alcohol and ether, more easily in nitrobenzene and pyridine with a yellowish red color. It dissolves yellow in cold sulfuric acid. From this solution the free ι · 2 '· 5' - dichlorophenylaminoanthraquinone - 2-carboxylic acid is precipitated in yellow-red flakes. In contrast to its benzyl ester, it is soluble in dilute alkalis with a blue-red color. The same procedure is used when using the esters with other aromatic alcohols and when condensing with other amines or ammonia.
Früheres Zusatzpatent: 256344.Former additional patent: 256344.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE267211C true DE267211C (en) |
Family
ID=524289
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT267211D Active DE267211C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE267211C (en) |
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- DE DENDAT267211D patent/DE267211C/de active Active
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