CH256773A - Process for the production of an anthraquinone derivative. - Google Patents
Process for the production of an anthraquinone derivative.Info
- Publication number
- CH256773A CH256773A CH256773DA CH256773A CH 256773 A CH256773 A CH 256773A CH 256773D A CH256773D A CH 256773DA CH 256773 A CH256773 A CH 256773A
- Authority
- CH
- Switzerland
- Prior art keywords
- production
- carbazolating
- anthraquinone derivative
- derivative
- parts
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 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 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 5
- 239000000975 dye Substances 0.000 claims description 4
- 240000007817 Olea europaea Species 0.000 claims description 2
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims description 2
- 150000004056 anthraquinones Chemical class 0.000 claims description 2
- 239000002585 base Substances 0.000 claims description 2
- 239000000835 fiber Substances 0.000 claims description 2
- 235000013311 vegetables Nutrition 0.000 claims description 2
- 239000000984 vat dye Substances 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- -1 sodium chloride Chemical class 0.000 description 4
- 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 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000005181 nitrobenzenes Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 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
- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
- C09B5/24—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic rings being only condensed with an anthraquinone nucleus in 1-2 or 2-3 position
- C09B5/26—Carbazoles of the anthracene series
- C09B5/28—Anthrimide carbazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Zusatzpatent zum Hauptpatent Nr. 250662. Verfahren zur Herstellung eines Anthrachinonderivates. Es wurde gefunden, dass ein wertvolles Anthraohinonderivat hergestellt werden kann, wenn man das Trianthrimid der Formel
EMI0001.0008
mit carbazolierenden Mitteln behandelt.
Das neue Anthrachinonderivat ist ein Kiz- penfarbstoff, :der sieh in konz. Schwefelsäure mit olivgrüner Farbe löst und pflanzliche Fa sern aus brauner Küpe in echten braunen Tönen färbt.
Das als Ausgangsstoff für das vorliegende Verfahren verwendete Trianthrimid kann bei spielsweise aus 1,4-Dihalogen-5-(p-ehlor-ben- zoyl)-aminoanthrachinonen durch Umsetzung mit \? Mal 1-Aminoanthrachinon in bekannter Weise erhalten werden. Als carbazolierende Mittel seien beispielsweise Aluminiumchlorid und Titantetrachlarid genannt. Diese Mittel können für sich allein oder in. Mischung bzw.
Verbindung mit Salzen wie Natriumchlorid, tertiären aromatischen Basen wie Pyridin oder Dimethylanilin, Nitrobenzolen, Ammo niak, organischen Nitrilen, organischen und anorganischen Säurechloriden und Sehwefel- dioxyd verwendet werden. Soweit sich bei der Behandlung mit carbazolierenden Mitteln wasserstoffreichere Verbindungen (Hydro- verbindungen) bilden, ist es vorteilhaft, die erhaltenen Produkte einer oxydierenden Be handlung zu unterwerfen, was z.
B: durch Behandeln mit Alkalihypochloritlösung, mit Natriumnitritlösung in saurem Medium oder mit Perboratlösung geschehen kann.
<I>Beispiel:</I> 21,5 Teile 1-p-Chlorbenzoylamino-5,8-.di- chlo:r-anthrachinon (grüngelbe Nadeln vom Schmelzpunkt 277 bis 279 ), 25 Teile 1- Aminoanthrachinon,15 Teile Natriumcarbonat,
1 Teil Kupferchlorür und 800 Teile Naph- thalin werden 15 bös 18 Stunden zum Sieden erhitzt. Bei etwa 180' wird die Schmelze mit etwa 400 Teilen Chlorbenzol verdünnt und das kristallisierte Reaktionsprodukt bei 50 bis 55' abfiltriert,
mit Chlorbenzol gewaschen; der Presskucken der Wasserdampfdestillation unterworfen und die neue Verbindung durch Filtration isoliert. Sie löst sich in konzen trierter Schwefelsäure mit grüner Färbe.
In 80 Gewichtsteile - Pyridin werden bei 50 bis<B>100'</B> langsam 40 Gewichtsteile gemah lenes, wasserfreies Aluminiumchlorid einge- tragen.
Bei etwa Z00 trägt man nun in diese Schmelze 20 Gewichtsteile des Trianthrimides aus 1 Mol 1;4 - Dichlar- 5 - (p - chlorbenzoyl)- aminoanthrachinon und 2 Mol 1-Aminoanthra- chinon ein. Man erhitzt nun eine Stunde zum Sieden jund trägt dann die Schmelze auf ver dünnte Natronlauge aus.
Nach dem Abdestil- lieren des Pyridins kann der neue Farbstoff durch Filtration isoliert werden.
Additional patent to main patent no. 250662. Process for the production of an anthraquinone derivative. It has been found that a valuable anthraohinone derivative can be made using the trianthrimide of the formula
EMI0001.0008
treated with carbazolating agents.
The new anthraquinone derivative is a Kizpen dye: see in conc. Sulfuric acid with an olive green color dissolves and dyes vegetable fibers from a brown vat in real brown tones.
The trianthrimide used as the starting material for the present process can be prepared, for example, from 1,4-dihalo-5- (p-chloro-benzoyl) -aminoanthraquinones by reaction with \? Sometimes 1-aminoanthraquinone can be obtained in a known manner. Examples of carbazolating agents are aluminum chloride and titanium tetrachlaride. These agents can be used alone or in a mixture or
Compound with salts such as sodium chloride, tertiary aromatic bases such as pyridine or dimethylaniline, nitrobenzenes, ammonia, organic nitriles, organic and inorganic acid chlorides and sulfur dioxide can be used. Insofar as hydrogen-rich compounds (hydro compounds) are formed during treatment with carbazolating agents, it is advantageous to subject the products obtained to an oxidizing treatment.
B: by treatment with alkali hypochlorite solution, with sodium nitrite solution in an acidic medium or with perborate solution.
<I> Example: </I> 21.5 parts of 1-p-chlorobenzoylamino-5,8-dichlo: r-anthraquinone (green-yellow needles with a melting point of 277 to 279), 25 parts of 1-aminoanthraquinone, 15 parts of sodium carbonate ,
1 part of copper chloride and 800 parts of naphthalene are heated to the boil for 15 18 hours. At about 180 'the melt is diluted with about 400 parts of chlorobenzene and the crystallized reaction product is filtered off at 50 to 55',
washed with chlorobenzene; the press cylinder is subjected to steam distillation and the new compound is isolated by filtration. It dissolves in concentrated sulfuric acid with a green color.
In 80 parts by weight of pyridine, 40 parts by weight of ground, anhydrous aluminum chloride are slowly introduced at 50 to <B> 100 '</B>.
At about Z00, 20 parts by weight of the trianthrimide from 1 mole of 1,4-dichloro-5- (p-chlorobenzoyl) -aminoanthraquinone and 2 moles of 1-aminoanthraquinone are then introduced into this melt. The mixture is now heated to the boil for an hour and then the melt is poured onto dilute sodium hydroxide solution.
After the pyridine has been distilled off, the new dye can be isolated by filtration.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH256773T | 1942-04-18 | ||
| CH250662T | 1943-03-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH256773A true CH256773A (en) | 1948-08-31 |
Family
ID=25729470
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH256773D CH256773A (en) | 1942-04-18 | 1942-04-18 | Process for the production of an anthraquinone derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH256773A (en) |
-
1942
- 1942-04-18 CH CH256773D patent/CH256773A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH256773A (en) | Process for the production of an anthraquinone derivative. | |
| CH256772A (en) | Process for the production of an anthraquinone derivative. | |
| CH250662A (en) | Process for the production of an anthraquinone derivative. | |
| CH256775A (en) | Process for the production of an anthraquinone derivative. | |
| CH256770A (en) | Process for the production of an anthraquinone derivative. | |
| CH256769A (en) | Process for the production of an anthraquinone derivative. | |
| DE470503C (en) | Process for the preparation of anthraquinone derivatives | |
| CH256774A (en) | Process for the production of an anthraquinone derivative. | |
| AT102533B (en) | Process for the production of vat dyes. | |
| CH256771A (en) | Process for the production of an anthraquinone derivative. | |
| CH258193A (en) | Process for the production of an anthraquinone derivative. | |
| AT59040B (en) | Process for the production of condensation products from indigo, its homologues and substitution products. | |
| DE515331C (en) | Process for the preparation of Kuepen dyes of the anthracene series | |
| CH308489A (en) | Process for the preparation of a dye of the dioxazine series. | |
| CH105234A (en) | Process for the production of 2.1-thionaphthisatin. | |
| CH285011A (en) | Process for the production of a quinazoline derivative. | |
| CH192028A (en) | Process for the preparation of 2-oxychrysen-8-carboxylic acid. | |
| CH285012A (en) | Process for the production of a quinazoline derivative. | |
| CH234295A (en) | Process for the production of a vat dye. | |
| CH251123A (en) | Process for the preparation of a dye mixture. | |
| CH238628A (en) | Process for the production of a vat dye. | |
| CH206729A (en) | Method for the preparation of 5 ': 5 "- dibenzoylamino-1: 1': 5: 1" - trianthrimide carbazole. | |
| CH133199A (en) | Process for the preparation of a dye of the anthraquinone series. | |
| CH238633A (en) | Process for the production of a vat dye. | |
| CH238629A (en) | Process for the production of a vat dye. |