DE443126C - Process for the preparation of nitro compounds of the arylaminoanthraquinones, their derivatives and substitution products - Google Patents
Process for the preparation of nitro compounds of the arylaminoanthraquinones, their derivatives and substitution productsInfo
- Publication number
- DE443126C DE443126C DEF57282D DEF0057282D DE443126C DE 443126 C DE443126 C DE 443126C DE F57282 D DEF57282 D DE F57282D DE F0057282 D DEF0057282 D DE F0057282D DE 443126 C DE443126 C DE 443126C
- Authority
- DE
- Germany
- Prior art keywords
- derivatives
- arylaminoanthraquinones
- blue
- substitution products
- preparation
- 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
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
- C07C225/24—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones the carbon skeleton containing carbon atoms of quinone rings
- C07C225/26—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones the carbon skeleton containing carbon atoms of quinone rings having amino groups bound to carbon atoms of quinone rings or of condensed ring systems containing quinone rings
- C07C225/32—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones the carbon skeleton containing carbon atoms of quinone rings having amino groups bound to carbon atoms of quinone rings or of condensed ring systems containing quinone rings of condensed quinone ring systems formed by at least three rings
- C07C225/34—Amino anthraquinones
-
- 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
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
- C09B1/32—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung von Nitroverbindungen der Arylaminoanthrachinone, ihrer Derivate und Substitutionsprodukte. Durch Patent 442 3 12 ist ein Verfahren zur Darstellung von N-Nitroso,arylaminoan-thrachinonen geschützt, welches darin besteht, daß man u. a. Arylaminoanthrachinone oder ihre Substitutionsprodukte mit nitrosi@erenden Mitteln behandelt.Process for the preparation of nitro compounds of the arylaminoanthraquinones, their derivatives and substitution products. By patent 442,312 is a method for the representation of N-nitroso, arylaminoan-thrachinonen protected, which in it insists that, among other things, Arylaminoanthraquinones or their substitution products with treated with nitrosizing agents.
Es wurde nun gefunden, daß diese Nitrosoverbindungen beim Erhitzen in Gegenwart organischer Säuren in Verbindungen übergehen, die im Arylaminorest nitriert sind.It has now been found that these nitroso compounds when heated in the presence of organic acids convert into compounds that are in the arylamino radical are nitrided.
Dieselben Nitroverbindungen erhält man, wenn man anstatt der N:itrosoverbndun@gen die Arylami:noanthrachinone, deren Derivate oder Substitutionsprodukte selbst in Gegenwart von organischen Säuren mit nitrosierenden Mitteln in der Wärme behandelt, wobei die N-Nitrosoverbindungen als Zwischenprodukte auftreten.The same nitro compounds are obtained if, instead of the N: itroso compounds the Arylami: noanthraquinones, their derivatives or substitution products themselves in The presence of organic acids treated with nitrosating agents in the heat, the N-nitroso compounds appearing as intermediates.
Die Darstellung nitrierter Arylaminoanthrachinone ist bereits aus den Patentschriften i i i 866 und 142 052 bekannt. Wähnend jedoch nach diesen Verfahren die Nitrierung nach altbekannten Methoden vorgenommen wird, beruht die Einführung von Nitrogruppen nach vorliegendem Verfahren nicht auf einer unmittelbaren Nitrierung, sondern darauf, daß in den sich zuerst bildenden Nitrosaminen die NO-Gruppe unter gleichzeitiger Oxydation zur NO-Gruppe in den Kern des Arylaminorestes wandert. Ähnliche Umlagerungen von N-Nitrosogruppen sind in der Benzol- und Carbazolreihe bekannt (s. z. B. Ber. i 9 [i886]> S. 2991; 2o [18871, S. 1247; 45 [19121, S. 1o96, S. io98;Patentschrift r34983). lnallen diesen Fällen bleiben aber die Nitrosogruppen als solche erhalten, während nach vorliegender Erfindung sofort die Nitroverbindungen, und zwar in kürzester Zeit und glatter Reaktion entstehen.The preparation of nitrated arylaminoanthraquinones is already known from patents iii 866 and 142 052 . While according to this process the nitration is carried out according to well-known methods, the introduction of nitro groups according to the present process is not based on an immediate nitration, but rather on the fact that in the nitrosamines which are formed first, the NO group with simultaneous oxidation to the NO group in the The core of the arylamino radical migrates. Similar rearrangements of N-nitroso groups are known in the benzene and carbazole series (see e.g. Ber. I 9 [i886]> p. 2991; 2o [18871, p. 1247; 45 [19121, p. 1096, p. Patent specification r34983). In all these cases, however, the nitroso groups are retained as such, while according to the present invention the nitro compounds are formed immediately, in a very short time and with a smooth reaction.
Die so darstellbaren Nitroverbindungen sind wichtige Zwischenprodukte zur Gewinnungvon Farbstoffen. Beispiel i. i Gewichtsteil i-N-Nitroso-p-tolylaminoanthrachinon wird in 2o Gewichtsteilen Eisessig suspendiert und zum Sieden erhitzt. Die Lösung färbt sich dunkel und läßt rasch einen orangefarbenen Körper in schönen Kristallnadeln ausfallen. Setzt man der Suspension vor dem Aufkochen etwas Natriumnitrit oder andere nitrosierende Mittel, z. B. Amylnitrit, zu, so wird die Ausbeute an dem orangefarbenen Körper quantitativ. Es hat die Konstitution: Beispiel a.The nitro compounds which can be prepared in this way are important intermediates for the production of dyes. Example i. i part by weight of iN-nitroso-p-tolylaminoanthraquinone is suspended in 20 parts by weight of glacial acetic acid and heated to the boil. The solution turns dark and quickly precipitates an orange-colored body in beautiful crystal needles. If you add a little sodium nitrite or other nitrosating agents to the suspension before boiling, e.g. B. amyl nitrite, the yield of the orange body is quantitative. It has the constitution: Example a.
i Gewichtsteil i, p-Tolylaminoanthrachinon wird in i o bis 2o Gewichtsbeilen siedendem Eisessig gelöst und in der Wärme langsam Natriumnitrit zugegeben, bis keine weitere Kristallabscheidung mehr erfolgt. Die Reaktion ist schon nach wenigen Minuten beendigt und der entstandene Körper mir dein in Beispiel i beschriebenen identisch. Beispiel 3.i part by weight of i, p-tolylaminoanthraquinone is used in i o to 20 parts by weight dissolved in boiling glacial acetic acid and slowly added sodium nitrite in the warmth until no further crystal separation takes place. The reaction is already after a few Minutes finished and the resulting body me yours described in example i identical. Example 3.
i Gewichtsteil i, q.-Di-p-tolylaniinoanthrachinon wird in etwa 3ö Gewichtsteilen siedendem Eisessig gelöst und weiter nach Beispiel i verfahren. Nach einigen Minuten fällt auch hier die Nitroverbindung, und zwar das i, ¢-Diz'-dinitro-q.'-dimethylphenylaminoanthrachinon, in schönen blauschwarzen Kristallnadeln aus.i part by weight of i, q.-Di-p-tolylaniinoanthraquinone is about 30 Parts by weight of boiling glacial acetic acid dissolved and continue according to Example i. To a few minutes here too the nitro compound falls, namely the i, ¢ -Diz'-dinitro-q .'-dimethylphenylaminoanthraquinone, in beautiful blue-black crystal needles.
In analoger W_ eise werden die in folgender Tabelle bezüglich ihrer
wesentlichsten Eigenschaften zusammengestelltenNitroderivate gewonnen
Claims (1)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEF57282D DE443126C (en) | 1924-11-07 | 1924-11-07 | Process for the preparation of nitro compounds of the arylaminoanthraquinones, their derivatives and substitution products |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEF57282D DE443126C (en) | 1924-11-07 | 1924-11-07 | Process for the preparation of nitro compounds of the arylaminoanthraquinones, their derivatives and substitution products |
Publications (1)
Publication Number | Publication Date |
---|---|
DE443126C true DE443126C (en) | 1927-04-22 |
Family
ID=7108222
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DEF57282D Expired DE443126C (en) | 1924-11-07 | 1924-11-07 | Process for the preparation of nitro compounds of the arylaminoanthraquinones, their derivatives and substitution products |
Country Status (1)
Country | Link |
---|---|
DE (1) | DE443126C (en) |
-
1924
- 1924-11-07 DE DEF57282D patent/DE443126C/en not_active Expired
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