CH133384A - Process for the production of an anthraquinone derivative. - Google Patents
Process for the production of an anthraquinone derivative.Info
- Publication number
- CH133384A CH133384A CH133384DA CH133384A CH 133384 A CH133384 A CH 133384A CH 133384D A CH133384D A CH 133384DA CH 133384 A CH133384 A CH 133384A
- Authority
- CH
- Switzerland
- Prior art keywords
- production
- anthraquinone derivative
- acid
- formic acid
- pure blue
- Prior art date
Links
- RZVHIXYEVGDQDX-UHFFFAOYSA-N 9,10-anthraquinone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 RZVHIXYEVGDQDX-UHFFFAOYSA-N 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 238000000034 method Methods 0.000 title claims description 3
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 10
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 6
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 5
- 235000019253 formic acid Nutrition 0.000 claims description 5
- ORFSSYGWXNGVFB-UHFFFAOYSA-N sodium 4-amino-6-[[4-[4-[(8-amino-1-hydroxy-5,7-disulfonaphthalen-2-yl)diazenyl]-3-methoxyphenyl]-2-methoxyphenyl]diazenyl]-5-hydroxynaphthalene-1,3-disulfonic acid Chemical compound COC1=C(C=CC(=C1)C2=CC(=C(C=C2)N=NC3=C(C4=C(C=C3)C(=CC(=C4N)S(=O)(=O)O)S(=O)(=O)O)O)OC)N=NC5=C(C6=C(C=C5)C(=CC(=C6N)S(=O)(=O)O)S(=O)(=O)O)O.[Na+] ORFSSYGWXNGVFB-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- 210000002268 wool Anatomy 0.000 claims description 2
- 239000000975 dye Substances 0.000 claims 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 229910000906 Bronze Inorganic materials 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 239000010974 bronze Substances 0.000 description 1
- KUNSUQLRTQLHQQ-UHFFFAOYSA-N copper tin Chemical compound [Cu].[Sn] KUNSUQLRTQLHQQ-UHFFFAOYSA-N 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- FWFGVMYFCODZRD-UHFFFAOYSA-N oxidanium;hydrogen sulfate Chemical compound O.OS(O)(=O)=O FWFGVMYFCODZRD-UHFFFAOYSA-N 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000000243 solution Substances 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
- C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
- C09B1/32—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups
- C09B1/34—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups sulfonated
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Zusatzpatent zum Hauptpatent Nr. 131358. Verfahren zur Herstellung eines Anthraehinonderivates. Es wurde gefunden, dass man ein Anthra- chinonderivat erhält, wenn man 1-Amino-4- anilidoanthrachinon, Benzaldehyd und Amei sensäure aufeinander einwirken lässt und das so erhaltene Produkt sulfiert. Der entstandene Farbstoff stellt wahrscheinlich eine Mono sulfosäure eines 1-Benzylamino-4-anilido- anthrachinons dar,
welches selbst durch die Einwirkung der Ameisensäure auf das Kon densationsprodukt des - Aldehydes mit dem Aminoanthrachinon oder durch die Einwirkung des Aldehydes auf das Kondensationsprodukt der Ameisensäure mit dem Aminoanthra- chinon entstanden sein kann. Er bildet ein dunkelblaues, in Wasser leicht mit reinblauer Farbe lösliches Pulver und färbt ungeheizte Wolle aus saurem Bad in klaren reinblauen echten Tönen an.
<I>Beispiel:</I> 15 Teile 1-Amino-4-anilidoanthrachinon werden in 100 Teilen Benzaldehyd gelöst und unter Zusatz von 7 Teilen 83 %iger Ameisensäure so lange zum Kochen erhitzt, bis die Reaktion beendet, d. h. keine weitere Verschiebung der Nuance der anfangs violet ten Farbe der Lösung nach blau mehr zu beobachten ist. Durch Verdünnen der Schmelze mit dem zwei bis dreifachen Volumen Methyl alkohol wird das gebildete Benzylderivat in bronzeglänzenden Kristallen abgeschieden. Es löst sich in organischen Lösungsmitteln, wie Benzol, Nitrobenzol, Eisessig eta., mit blauer Farbe.
1 Teil dieses Produktes wird in 3 Teilen Schwefelsäuremonohydrat gelöst, mit 1 Teil Oleum von 28 % SOS-Gehalt versetzt und so lange bei einer Temperatur von 25 bis 35 0 gehalten, bis vollständige Wasserlöslichkeit eingetreten ist.
Die Farbstoffsulfosäüre wird in der üb lichen Weise mit Kochsalz oder Chlorkalium als Salz gefällt, abfiltriert, mit Salzlösung gewaschen und getrocknet.
Additional patent to main patent no. 131358. Process for the production of an anthraquinone derivative. It has been found that an anthraquinone derivative is obtained if 1-amino-4-anilidoanthraquinone, benzaldehyde and formic acid are allowed to act on one another and the product thus obtained is sulfated. The resulting dye is probably a monosulfonic acid of a 1-benzylamino-4-anilido-anthraquinone,
which itself can have arisen through the action of formic acid on the condensation product of the aldehyde with the aminoanthraquinone or through the action of the aldehyde on the condensation product of formic acid with the aminoanthraquinone. It forms a dark blue powder that is easily soluble in water with a pure blue color and stains unheated wool from an acid bath in clear, pure blue real tones.
<I> Example: </I> 15 parts of 1-amino-4-anilidoanthraquinone are dissolved in 100 parts of benzaldehyde and, with the addition of 7 parts of 83% formic acid, heated to the boil until the reaction has ended; H. no further shift in the shade of the initially violet color of the solution to blue can be observed. By diluting the melt with two to three times the volume of methyl alcohol, the benzyl derivative formed is deposited in shiny bronze crystals. It dissolves in organic solvents, such as benzene, nitrobenzene, glacial acetic acid, etc., with a blue color.
1 part of this product is dissolved in 3 parts of sulfuric acid monohydrate, 1 part of oleum with 28% SOS content is added and the mixture is kept at a temperature of 25 to 35 ° until complete solubility in water has occurred.
The dye sulfonic acid is precipitated in the usual manner with sodium chloride or potassium chloride as the salt, filtered off, washed with brine and dried.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH133384T | 1926-08-26 | ||
| CH131358T | 1927-12-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH133384A true CH133384A (en) | 1929-05-31 |
Family
ID=25711600
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH133384D CH133384A (en) | 1926-08-26 | 1926-08-26 | Process for the production of an anthraquinone derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH133384A (en) |
-
1926
- 1926-08-26 CH CH133384D patent/CH133384A/en unknown
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