DE125094C - - Google Patents
Info
- Publication number
- DE125094C DE125094C DENDAT125094D DE125094DA DE125094C DE 125094 C DE125094 C DE 125094C DE NDAT125094 D DENDAT125094 D DE NDAT125094D DE 125094D A DE125094D A DE 125094DA DE 125094 C DE125094 C DE 125094C
- Authority
- DE
- Germany
- Prior art keywords
- diamidoanthraquinone
- product
- chlorine
- acetic acid
- glacial acetic
- 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
- 239000000460 chlorine Substances 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 229960000583 Acetic Acid Drugs 0.000 claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 4
- 239000012362 glacial acetic acid Substances 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 239000000047 product Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 210000002969 Egg Yolk Anatomy 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N Nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 235000013345 egg yolk Nutrition 0.000 description 2
- KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical class ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002035 prolonged Effects 0.000 description 1
- 239000003638 reducing agent Substances 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
- 238000010626 work up procedure Methods 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
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/22—Dyes with unsubstituted amino groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Description
KAISERLICHESIMPERIAL
\ PATENTAMT.\ PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
M 125094 KLASSE Hq. M 125094 CLASS Hq.
Patentirt im Deutschen Reiche vom 3. Januar 1899 ab.Patented in the German Empire on January 3, 1899.
Durch Einwirkung von Chlor auf i-5-Diamidoanthrachinon bei gewöhnlicher Temper ratur entstehen zwei Reactionsproducte, von denen das eine im Wesentlichen ein Tetrachlorderivat, das andere ein noch höher substituirtes Diamidoanthrachinon ist, und bei verstärkter Einwirkung des Chlors wird hauptsächlich letzteres Product erhalten:By the action of chlorine on i-5-diamidoanthraquinone at ordinary temper temperature, two reaction products arise, one of which is essentially a tetrachloride derivative, the other is an even more highly substituted diamidoanthraquinone, and with a stronger one The effect of chlorine is mainly the latter product:
. Das erstbesprochene Product ist bereits Gegenstand des Patentes 104901, Kl. 12. Das Verfahren bleibt daher auf die Darstellung des zweiten höher substituirten Products beschränkt, welches ein werthvolles Ausgangsmaterial zur Herstellung von Farbstoffen bildet.. The product discussed first is already the subject of patent 104901, cl. 12. The method therefore remains limited to the presentation of the second, more highly substituted product, which is a valuable starting material for the manufacture of dyes.
10 kg i .· 5-Diamidoanthrachinon werden in 200 kg Eisessig suspendirt, und bei gewöhnlicher oder schwach erhöhter Temperatur Chlor eingeleitet. Unter schwacher Erwärmung und Ausstofsung von .Salzsäuredämpfen geht die Chlorirung vor sich. Dieselbe wird fortgesetzt, bis völlige oder nahezu völlige Lösung erfolgt ist.10 kg i. · 5-diamidoanthraquinone are in 200 kg of glacial acetic acid suspended, and chlorine at ordinary or slightly elevated temperatures initiated. The Chlorination before him. This continues until complete or near complete dissolution occurs is.
Behufs Aufarbeitung wird die Reactionsflüssigkeit erforderlichenfalls filtrirt und das Filtrat mit etwa der fünffachen Menge Wasser versetzt. Es entsteht ein eigelber Niederschlag, welcher abfiltrirt, gewaschen und getrocknet wird. Er bildet in trockenem Zustande ein eigelbes Pulver; dasselbe ist in den meisten Lösungsmitteln, wie Alkohol, Aether, Benzol, Nitrobenzol, Eisessig etc., sehr leicht mit gelber Farbe löslich, in kalter concentrirter Schwefelsäure unlöslich; es zeigt, wie oben erhalten, keinen scharfen Schmelzpunkt, sintert bei etwa 90 ° C. und schmilzt bei längerem Erhitzen auf ioo° C. Dieses als Polychlordiamidoanthrachinon bezeichnete Product besteht nach diesbezüglichen Untersuchungen im Wesentlichen aus einem Oktochlordiamidoanthrachinon, in welchem sehr wahrscheinlich zwei oder alle vier Amidwasserstoffatome durch Chloratome ersetzt sind. Es läfst sich durch Behandlung mit schwach alkalischen Mitteln oder mit Reductionsmitteln in chlorärmere Producte, z. B. in das für die Darstellung von Farbstoffen wichtige Penta- und Tetrachldrdiamidoanthrachinon überführen. .For work-up, the reaction liquid is filtered if necessary and that About five times the amount of water was added to the filtrate. An egg yolk precipitate is formed, which is filtered off, washed and dried. He imagines when dry egg yolk powder; the same is in most solvents, such as alcohol, ether, benzene, Nitrobenzene, glacial acetic acid, etc., very easily soluble with a yellow color, in cold concentrated sulfuric acid insoluble; as obtained above, it shows no sharp melting point, sinters at about 90 ° C. and melts on prolonged heating to 100 ° C. This as polychlorodiamidoanthraquinone According to investigations in this regard, the designated product essentially consists of an octochlorodiamidoanthraquinone, in which very likely two or all four amide hydrogen atoms by chlorine atoms are replaced. It can be achieved by treatment with weakly alkaline agents or with reducing agents in products lower in chlorine, e.g. B. in that for the representation of dyes transfer important penta- and tetrachdiamidoanthraquinone. .
An Stelle des Eisessigs können im vorstehenden Beispiel auch andere Lösungsmittel verwendet werden ;■ sofern dieselben mit Wasser nicht mischbar sind, so dafs aus ihnen das Product nicht einfach durch Wasser gefällt. ■werden kann, müfs natürlich seine Abscheidung in geeigneter Weise, z. B. durch Abdestilliren des Lösungsmittels geschehen.Instead of glacial acetic acid, other solvents can also be used in the above example are used; ■ if they are immiscible with water, then from them that Product not just liked by water. ■ can of course be separated in a suitable manner, e.g. B. done by distilling off the solvent.
Claims (1)
Verfahren zur Darstellung eines im Wesentlichen aus Oktochlordiamidoanthrachinon bestehenden Polychlorsubstitutionsproducts des ι · 5-Diamidoanthrachinons, dadurch gekennzeichnet, dafs ι · 5-Diamidoanthrachinon in Eisessig oder anderen geeigneten Lösungsmitteln mit Chlor im Ueberschufs behandelt wird.Patent claim:
Process for the preparation of a polychlorosubstitution product of ι · 5-diamidoanthraquinone consisting essentially of octochlorodiamidoanthraquinone, characterized in that ι · 5-diamidoanthraquinone is treated in glacial acetic acid or other suitable solvents with excess chlorine.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE125094C true DE125094C (en) |
Family
ID=393841
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT125094D Active DE125094C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE125094C (en) |
-
0
- DE DENDAT125094D patent/DE125094C/de active Active
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