DE266945C - - Google Patents
Info
- Publication number
- DE266945C DE266945C DENDAT266945D DE266945DA DE266945C DE 266945 C DE266945 C DE 266945C DE NDAT266945 D DENDAT266945 D DE NDAT266945D DE 266945D A DE266945D A DE 266945DA DE 266945 C DE266945 C DE 266945C
- Authority
- DE
- Germany
- Prior art keywords
- parts
- anthraquinone
- solution
- nitrobenzene
- free
- 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
- LQNUZADURLCDLV-UHFFFAOYSA-N Nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000011230 binding agent Substances 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 3
- SMWDFEZZVXVKRB-UHFFFAOYSA-N quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M Potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- RFKZUAOAYVHBOY-UHFFFAOYSA-M copper(1+);acetate Chemical compound [Cu+].CC([O-])=O RFKZUAOAYVHBOY-UHFFFAOYSA-M 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-Trioxane Chemical group C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 1
- MVRDXWVWKOUPDO-UHFFFAOYSA-N 1-amino-2-bromoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC(Br)=C2N MVRDXWVWKOUPDO-UHFFFAOYSA-N 0.000 description 1
- BOCJQSFSGAZAPQ-UHFFFAOYSA-N 1-chloroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2Cl BOCJQSFSGAZAPQ-UHFFFAOYSA-N 0.000 description 1
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2H-oxazine Chemical group N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 244000061775 Olea africana Species 0.000 description 1
- 235000002852 Olea africana Nutrition 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L Sulphite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 235000005811 Viola adunca Nutrition 0.000 description 1
- 240000009038 Viola odorata Species 0.000 description 1
- 235000013487 Viola odorata Nutrition 0.000 description 1
- 235000002254 Viola papilionacea Nutrition 0.000 description 1
- 230000002378 acidificating Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229940116318 copper carbonate Drugs 0.000 description 1
- GEZOTWYUIKXWOA-UHFFFAOYSA-L copper;carbonate Chemical compound [Cu+2].[O-]C([O-])=O GEZOTWYUIKXWOA-UHFFFAOYSA-L 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N n-pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical class [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000001187 sodium carbonate Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- IVNZBWNBYXERPK-DZGBHZPSSA-K trisodium;(8Z)-7-oxo-8-[(4-sulfonatonaphthalen-1-yl)hydrazinylidene]naphthalene-1,3-disulfonate Chemical group [Na+].[Na+].[Na+].C1=CC=C2C(N\N=C3/C(=O)C=CC=4C=C(C=C(C=43)S([O-])(=O)=O)S(=O)(=O)[O-])=CC=C(S([O-])(=O)=O)C2=C1 IVNZBWNBYXERPK-DZGBHZPSSA-K 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/34—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings
- C07D265/38—[b, e]-condensed with two six-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Coloring (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
Vi 266945 KLASSE \2p. GRUPPEVi 266945 CLASS \ 2p. GROUP
Verfahren zur Darstellung von Anthrachinon-N-l-l'-oxazinen.Process for the preparation of anthraquinone-N-l-l'-oxazines.
Patentiert im Deutschen Reiche vom 8. Februar 1912 ab.Patented in the German Empire on February 8, 1912.
Es wurde gefunden, daß Gemische von 2-Halogen-i-aminoanthrachinonen und i-Halogenanthrachionen mit freier 2-Stellung beim Erhitzen in Nitrobenzollösung, mit einem säurebindenden ! Mittel und einem Katalysator an Stelle der zu erwartenden 2-Halogen-i · i'-dianthrimide neue halogenfreie alkaliunlösliche Körper liefern, welche als die bisher unbekannten Anthrachinon-N-i · 1'-oxazine zu betrachten sind. Diese sind wertvolle Ausgangsstoffe zur Darstellung von Farbstoffen.It has been found that mixtures of 2-halo-i-aminoanthraquinones and i-haloanthraquinones with free 2-position when heated in nitrobenzene solution, with an acid-binding ! Agents and a catalyst in place of the expected 2-halo-i · i'-dianthrimides provide new halogen-free, alkali-insoluble bodies which are to be regarded as the hitherto unknown anthraquinone-Ni · 1'-oxazines. These are valuable starting materials for the representation of dyes.
Es hat nicht festgestellt werden können, wie die Reaktion zu erklären ist. Die Konstitution der Endprodukte ergibt sich daraus, daß ζ. B. aus 2-Brorn-i-aminoanthrachinon und i-Chloranthrachinon unter den angegebenen Bedingungen dasselbe Anthrachinon-N-i · 1'-oxazin It has not been possible to determine how the reaction is to be explained. The constitution of the end products results from the fact that ζ. B. from 2-brorn-i-aminoanthraquinone and i-chloranthraquinone among those indicated Conditions the same anthraquinone-N-i · 1'-oxazine
-25 entsteht, welches auch gewonnen wird, wenn man i-Nitro-2-oxyanthrachinon mit i-Chloranthrachinon in Nitrobenzollösung in Gegenwart von Kupferpulver am Rückflußkühler erhitzt. Andererseits erhält man in normaler Weise 2-Brom-i · i'-dianthrimid aus 2-Bromi-aminoanthrachinon und i-Chloranthrachinon, wenn man die Umsetzung in kochendem Amylalkohol bei Gegenwart von z. B. Kaliumacetat und Kupferacetat vornimmt.-25 arises, which is also gained if one i-nitro-2-oxyanthraquinone with i-chloroanthraquinone heated in nitrobenzene solution in the presence of copper powder on the reflux condenser. On the other hand you get in normal Way 2-bromo-i'-dianthrimide from 2-bromino-aminoanthraquinone and i-chloranthraquinone, if the reaction is carried out in boiling amyl alcohol in the presence of e.g. B. potassium acetate and copper acetate.
3535
ι. Ein Gemisch von zoo Teilen i-Chloranthrachinon, 50 Teilen 2-Brom-i-aminoanthrachinon, 500 Teilen Nitrobenzol, 50 Teilen entwässertem Natriumacetat, 1 Teil Kupferacetat wird etwa 24 Stunden am Rückflußkühler gekocht. Das abgeschiedene Produkt wird dann abfiltriert und nacheinander mit Wasser und Alkohol gewaschen.ι. A mixture of zoo parts of i-chloroanthraquinone, 50 parts of 2-bromo-i-aminoanthraquinone, 500 parts of nitrobenzene, 50 parts of dehydrated Sodium acetate, 1 part of copper acetate is refluxed for about 24 hours. The deposited product is then filtered off and washed successively with water and alcohol.
Aus Chinolin umkristallisiert gab der Körper bei der Analyse folgende Zahlen:Recrystallized from quinoline, the body gave the following numbers during the analysis:
Berechnet für C28 H13 Calculated for C 28 H 13
C 75,85 Prozent C 75.85 percent
H 2,93 H 2.93
N 3.16 - · N 3.16 -
Gefunden:Found:
C 75,86, 75,4, 75,79 Prozent C 75.86, 75.4, 75.79 percent
H 3,08, 2,98, 1 rn H 3.08, 2.98, 1 mn
3.093.09
a 3,00, '/,90, 3,09
N 3,48, 3,40, 3,38 a 3.00, '/, 90, 3.09
N 3.48, 3.40, 3.38
5555
Das Anthrachinon-N-i · i'-oxazin bildet ein braünviolettes Kristallpulver, das sich in konzentrierter Schwefelsäure mit grüner Farbe löst und aus dieser Lösung beim Verdünnen mit 'Wasser in rotvioletten Flocken gefällt wird. In indifferenten Lösungsmitteln, mit Ausnahme von Chinolin, ist es selbst beim Kochen nur sehr wenig löslich. Die Lösung in Nitrobenzol ist in der Kälte violettrot, beim Kochen rotstichig violett, diejenige in Anilin in der Kälte blau, beim Erwärmen violett.The anthraquinone-N-i · i'-oxazine forms a brownish-violet crystal powder, which is concentrated in Sulfuric acid with a green color dissolves and precipitates from this solution in red-violet flakes when diluted with water will. In inert solvents, with the exception of quinoline, it is even with Very sparingly soluble in boiling. The solution in nitrobenzene is purple-red in the cold, when Reddish purple when cooked, blue in aniline in the cold, purple when heated.
Aus der braun- bis braunoliven Küpe wird Baumwolle nicht gefärbt, dagegen läßt sich das Produkt sulfieren und gibt dann einen sauren blauvioletten Farbstoff.Cotton from the brown to brown olive vat is not dyed, but can be sulfonate the product and then give an acidic blue-violet dye.
2. 25 Teile 1 · 5-Diamino-2 · 6-dibromanthrachinon (vgl. Scholl und Berblinger, Ber. 37 [1904], S. 4180), werden mit 100 Teilen 1-Chloranthrachinon und 500 Teilen Nitrobenzol in Gegenwart von 50 Teilen Natriumcarbonat und 2 Teilen Kupfercarbonat etwa 50 Stunden am Rückflußkühler unter Rühren gekocht. Nach dem Erkalten wird mit Toluol verdünnt ; das abgeschiedene Produkt wird abgesaugt und die anorganischen Beimengungen werden durch verdünnte Salzsäure entfernt. Nach dem Auskochen mit Chinolin verbleibt das Reaktionsprodukt als braunschwarzes Pulver, das sich in konzentrierter Schwefelsäure grün löst und aus dieser Lösung durch Wasser in tiefblauen Flocken gefällt wird. Die konzentriert schwefelsaure Lösung gibt mit Trioxymethylen keinen Farbumschlag. Da der Körper bromfrei und alkaliunlöslich ist, muß angenommen werden, daß er den Oxazinring zweimal im Molekül enthält.2. 25 parts of 1 · 5-diamino-2 · 6-dibromoanthraquinone (cf. Scholl and Berblinger, Ber. 37 [1904], p. 4180), with 100 parts of 1-chloroanthraquinone and 500 parts of nitrobenzene in the presence of 50 parts of sodium carbonate and 2 parts of copper carbonate for about 50 hours boiled on the reflux condenser with stirring. After cooling, it is diluted with toluene ; the deposited product is filtered off with suction and the inorganic impurities are removed using dilute hydrochloric acid. After boiling with quinoline, the reaction product remains as a brown-black powder, which dissolves green in concentrated sulfuric acid and from this solution through water is precipitated in deep blue flakes. The concentrated sulfuric acid solution gives with trioxymethylene no color change. Since the body is bromine-free and insoluble in alkali, it must be assumed that it has the oxazine ring contains twice in the molecule.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE266945C true DE266945C (en) |
Family
ID=524036
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT266945D Active DE266945C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE266945C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1194860B (en) * | 1959-05-14 | 1965-06-16 | Smith Kline French Lab | Process for the preparation of substituted phenoxazines |
-
0
- DE DENDAT266945D patent/DE266945C/de active Active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1194860B (en) * | 1959-05-14 | 1965-06-16 | Smith Kline French Lab | Process for the preparation of substituted phenoxazines |
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