DE127780C - - Google Patents
Info
- Publication number
- DE127780C DE127780C DENDAT127780D DE127780DA DE127780C DE 127780 C DE127780 C DE 127780C DE NDAT127780 D DENDAT127780 D DE NDAT127780D DE 127780D A DE127780D A DE 127780DA DE 127780 C DE127780 C DE 127780C
- Authority
- DE
- Germany
- Prior art keywords
- dinitro
- diamidoanthraquinone
- soluble
- green
- diacetyldiamido
- 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 12
- -1 acetyl compound Chemical class 0.000 claims description 8
- LQNUZADURLCDLV-UHFFFAOYSA-N Nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 6
- 239000000843 powder Substances 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 3
- 238000002844 melting Methods 0.000 claims description 3
- 239000000155 melt Substances 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 230000000875 corresponding Effects 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 2
- 229960000583 Acetic Acid Drugs 0.000 claims 1
- MCDYRPYNGUBKPE-UHFFFAOYSA-L [Sn+2]=O.[O-]S([O-])(=O)=O Chemical compound [Sn+2]=O.[O-]S([O-])(=O)=O MCDYRPYNGUBKPE-UHFFFAOYSA-L 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 1
- 125000003368 amide group Chemical group 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- QSJXEFYPDANLFS-UHFFFAOYSA-N diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 claims 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 239000012362 glacial acetic acid Substances 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 230000004048 modification Effects 0.000 claims 1
- 238000006011 modification reaction Methods 0.000 claims 1
- 239000002244 precipitate Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 2
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000006396 nitration reaction Methods 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 239000002253 acid Substances 0.000 description 1
- 239000010425 asbestos Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000005121 nitriding Methods 0.000 description 1
- 150000003142 primary aromatic amines Chemical class 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 238000007127 saponification reaction 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
In dem Patente 125391 wurde gezeigt, dafs man durch Nitriren von Acetylmonoamidoanthrachinon zu dem bis dahin unbekannten ι · 4-Nitroamidoanthrachinon gelangen kann.It was shown in patent 125,391 that the hitherto unknown ι · 4-nitroamidoanthraquinone can be obtained by nitriding acetylmonoamidoanthraquinone.
Analog verhalten sich nun die Acetylverbindungen der 1 · 5- und 1 · 8-Diamidoanthrachinone, welche bei der Nitrirung die Acetylderivate des 4 · 8-Dinitro-i · 5-diamido- bezw. des 4 · 5 - Dinitro - 1 · 8 - diamidoanthrachinons liefern.The acetyl compounds of the 1 · 5- and 1 · 8-diamidoanthraquinones behave analogously, which in nitration the acetyl derivatives of 4 · 8-dinitro-i · 5-diamido or. of the 4 · 5 - dinitro - 1 · 8 - diamidoanthraquinone.
Durch Reduction dieser Dinitrodiamidoverbindungen erhält man das bisher unbekannte ι · 4 · 5 · 8-Tetraamidoanthrachinon; durch Einwirkung von primären aromatischen Aminen erhält man, indem die Nitrogruppen durch die Alphylaminreste ausgetauscht werden, blaue Farbstoffe.The hitherto unknown is obtained by reducing these dinitrodiamido compounds ι · 4 · 5 · 8-tetraamidoanthraquinone; by action from primary aromatic amines, by exchanging the nitro groups for the alphylamine residues, blue ones are obtained Dyes.
Beispiele:
i. Darstellung des 1 · 5 - Diacetyldi-Examples:
i. Representation of the 1 · 5 - diacetyldi
amidoanthrachinons.
ι Th. ι · 5-Diamidoanthrachinon wird mit 10 Th. Essigsäureanhydrid etwa eine Stunde
lang zum Kochen erhitzt, wobei sich die gebildete Diacetylverbindung in hellbraunen,
glänzenden Krystallen abscheidet. Dieselben werden nach dem Erkalten abgesaugt und sind
direct vollkommen rein. Der Schmelzpunkt der Verbindung liegt über 3000, die Lösung
in cone. Schwefelsäure ist gelb.amidoanthraquinones.
ι th. ι · 5-diamidoanthraquinone is heated to boiling with 10 th. acetic anhydride for about one hour, the diacetyl compound formed separating out in light brown, shiny crystals. These are sucked off after cooling and are immediately completely pure. The melting point of the compound is above 300 0 , the solution in cone. Sulfuric acid is yellow.
2. Darstellung des 1 · 5-Diacetyldiamido-4«8-dinitroanthrachinons. 2. Preparation of the 1 · 5-diacetyldiamido-4 «8-dinitroanthraquinone.
ι ο kg der wie vorstehend erhaltenen Diacetylverbindung werden in 50 kg Schwefelsäure von 66° B. gelöst und bei einer Temperatur von 10 bis 150 langsam mit 24 1 Nitrirsäure (200 g HNÖa in 1 1 enthaltend) versetzt. Die Nitrirung ist in etwa einer Stunde beendet. Bei richtig geleiteter Operation scheidet sich das entstandene Nitroproduct in gelben Kryställchen aus der Schmelze ab. Durch Absaugen über ein Asbestfilter und mehrfaches Decken mit öogrädiger Schwefelsäure erhält man das Product direct rein.ι ο kg of the diacetyl compound obtained as above are dissolved in 50 kg of sulfuric acid of 66 ° B. and slowly mixed with 24 1 of nitriric acid (200 g of HNÖ a in 1 1) at a temperature of 10 to 15 0. The nitration is completed in about an hour. If the operation is properly managed, the resulting nitro product separates out of the melt in yellow crystals. The product can be obtained directly clean by suction using an asbestos filter and covering several times with odorous sulfuric acid.
Die so erhaltene Acetylverbindung des Dinitrodiamidoanthrachinons ist ein gelbes, in Wasser ganz unlösliches Pulver. Organische Solventien lösen dasselbe nur sehr schwierig; aus viel siedendem Nitrobenzol erscheint es beim Erkalten in braungelben Prismen von hohem Schmelzpunkt. In kalter cone. Schwefelsäure ist das Product so gut wie unlöslich.The acetyl compound of dinitrodiamidoanthraquinone thus obtained is a yellow, in Water completely insoluble powder. Organic solvents solve the same only with great difficulty; from a lot of boiling nitrobenzene it appears in brown-yellow prisms of high melting point. In cold cone. Sulfuric acid is the product as good as insoluble.
3. Verseifung der Diacetylverbindung3. Saponification of the diacetyl compound
des Beispiels 2.of example 2.
Die nach Beispiel 2 erhaltene Diacetylverbindung wird in 5 Th. Schwefelsäure von 660B. bei 80 bis 90 ° gelöst und die Lösung einige Zeit auf dem Wasserbade digerirt. Beim Erkalten scheiden sich fast farblose, flächen-The diacetyl compound obtained according to Example 2 is dissolved in 5 Th. Sulfuric acid of 66 0 B. at 80 to 90 ° and the solution digested for some time on the water bath. When it cools down, almost colorless, flat
Claims (2)
Abänderung des durch Patent 125391 geschützten Verfahrens zur Darstellung von 1 · 4-Nitroacetylamidoanthrachinon und i-4-Nitroamidoanthrachinon, darin bestehend, dafs man Ί. statt der Acetylverbindung des a-Amidoanthrachinons hier die Diacetylverbindung des ι -5- bezw. des 1 · 8-Diamidoanthrachinons nitrirt, zwecks Gewinnung von ι · 5 - Diacetyldiamido - 4 · 8 - dinitro - bezw. ι · 8-Diacetyldiamido-4 · 5-dinitroanthrachinon; Patent-A ν saying:
Modification of the process protected by patent 125391 for the preparation of 1 · 4-nitroacetylamidoanthraquinone and i-4-nitroamidoanthraquinone, consisting in the fact that Ί. instead of the acetyl compound of the a-amidoanthraquinone here the diacetyl compound of the ι -5- respectively. of the 1 · 8-diamidoanthraquinone nitrated, for the purpose of obtaining ι · 5 - diacetyldiamido - 4 · 8 - dinitro - respectively. ι · 8-diacetyldiamido-4 · 5-dinitroanthraquinone;
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE127780C true DE127780C (en) |
Family
ID=396352
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT127780D Active DE127780C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE127780C (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2562314A (en) * | 1948-05-25 | 1951-07-31 | Celanese Corp | Process for producing a 1,4,5,8-tetraminoanthraquinone dyestuff |
| US2607782A (en) * | 1947-09-30 | 1952-08-19 | Celanese Corp | Process for the production of 1:4:5:8 tetraamino-anthraquinone |
-
0
- DE DENDAT127780D patent/DE127780C/de active Active
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2607782A (en) * | 1947-09-30 | 1952-08-19 | Celanese Corp | Process for the production of 1:4:5:8 tetraamino-anthraquinone |
| US2562314A (en) * | 1948-05-25 | 1951-07-31 | Celanese Corp | Process for producing a 1,4,5,8-tetraminoanthraquinone dyestuff |
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