CH258193A - Process for the production of an anthraquinone derivative. - Google Patents
Process for the production of an anthraquinone derivative.Info
- Publication number
- CH258193A CH258193A CH258193DA CH258193A CH 258193 A CH258193 A CH 258193A CH 258193D A CH258193D A CH 258193DA CH 258193 A CH258193 A CH 258193A
- Authority
- CH
- Switzerland
- Prior art keywords
- anthraquinone derivative
- parts
- production
- brown
- carbazolating
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 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
- 238000004519 manufacturing process Methods 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 5
- 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 3
- 150000004056 anthraquinones Chemical class 0.000 claims description 3
- 239000000975 dye Substances 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 2
- 239000002585 base Substances 0.000 claims description 2
- 239000001058 brown pigment Substances 0.000 claims 1
- 239000000049 pigment 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 6
- 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
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- LRMDXTVKVHKWEK-UHFFFAOYSA-N 1,2-diaminoanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C(N)C(N)=CC=C3C(=O)C2=C1 LRMDXTVKVHKWEK-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-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
- 239000002253 acid Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- -1 sodium chloride Chemical class 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- WYPZQZXSFVPVMI-UHFFFAOYSA-N 1,4-diamino-5,8-dichloroanthracene-9,10-dione Chemical class O=C1C2=C(Cl)C=CC(Cl)=C2C(=O)C2=C1C(N)=CC=C2N WYPZQZXSFVPVMI-UHFFFAOYSA-N 0.000 description 1
- CNSNLRXGBRBCAU-UHFFFAOYSA-N 5-amino-1,4-dichloroanthracene-9,10-dione Chemical compound O=C1C2=C(Cl)C=CC(Cl)=C2C(=O)C2=C1C=CC=C2N CNSNLRXGBRBCAU-UHFFFAOYSA-N 0.000 description 1
- ZDALKGQRWQDVHC-UHFFFAOYSA-N C(C1=CC=CC=C1)(=O)NC1=CC=C(C=2C(C3=C(C=CC(=C3C(C12)=O)Cl)Cl)=O)NC(C1=CC=CC=C1)=O Chemical compound C(C1=CC=CC=C1)(=O)NC1=CC=C(C=2C(C3=C(C=CC(=C3C(C12)=O)Cl)Cl)=O)NC(C1=CC=CC=C1)=O ZDALKGQRWQDVHC-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 150000005181 nitrobenzenes 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
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 239000000984 vat dye 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
- 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
Verfahren zur Herstellung eines Anthrachinonderivates. Es wurde gefunden, dass ein wertvolles Anthrachinonderivat hergestellt werden kann, wenn man das Trianthrimid der Formel
EMI0001.0005
mit earba.zolierenden Mitteln behandelt. Das neue Anthrachinonderivat ist ein Küpenfarbstoff, der sich in konzentrierter Schwefelsäure mit violetter Farbe löst und Baumwolle aus brauner Küpe kräftig grau braun färbt.
Das als Ausgangsstoff für das vorliegende Verfahren verwendete Trianthrimid kann beispielsweisse aus: 1,4 - Dihalogen - 5,8 - di- benzoyldiaminoanthraehinonen durch Um setzung mit 2 Mol 1-Aminoanthrachinon in be kannter Weise erhalten werden. Als carbazo- lierende Mittel seien beispielsweise Alumi niumchlord und Titantetrachlorid genannt. Diese Mittel können für sich allein oder in Mischung bzw.
Verbindung mit Salzen, wie Natriumchlorid, tertiären aromatischen Basen, wie Pyridin oder Dimethyl'anilin, Nitro- benzolen, Ammoniak, organischen Nitrilen, organischen und anorganischen.Säurechloriden und Schwefeldioxyd verwendet werden.
So weit sich bei der Behandlung mit carbazolie- renden Mitteln wasserstoffreichere Verbin dungen (Hydroverbindungen) bilden, ist es vorteilhaft, die erhaltenen Produkte einer oxydierenden Behandlung zu unterwerfen, was z. B. durch Behandeln mit AlkaJihypo- chl.oritlös@ung, mit Natriumnitritlösung in saurem Medium oder mit Perboratlösung ge schehen kann.
<I>Beispiel:</I> 22 Teile 1,4-Diehlor-5,8-dibenzoyldiamino- anthrachinon und 22 Teile 1-Aminoanthra- chinon werden zusammen mit 15 Teile. Na- triumearbonat, 2 Teilen Kupferchlorür und 300 Teilen Naphthalin während 15 Stunden zum Sieden erhitzt.
Bei 1ä0 gibt man so dann 600 Teile Chlorbenzol zu, filtriert das Umsetzungsprodukt kalt ab, wäscht mit Chlorbenzol aus, entfernt das Chlorbenzol aus dem Presskuchen mit Wasserdampf und isoliert die neue Verbindung durch Filtra tion. Sie löst sich in konzentrierter Schwefel säure mit grasgrüner Farbe.
In 80 Teilss Pyridin werden bei 50-l00 langsam 40 Teile gemahlenes, wasserfreies Aluminiumchlorid eingetragen. Bei etwa 100 trägt man nun in diese Schmelze 20 Teile des Trianthrimids aus. 1 Mol 1,4-Diehlor-5,8- dibenzoyl'diaminoanthrachinon und 2 Mol 1-Aminoanthrachinon ein.
Man erhitzt nun eine Stunde zum Sieden und trägt dann die Schmelze auf verdünnte Natronlauge aus. Nach dem Abdestülieren des Pyridins kann der neue Farbstoff durch Filtration isoliert werden.
Das oben erwähnte 1,4-Dichlor-5,8-di- benzoyl'diaminoanthrachinon kann wie folgt erhalten werden: 1,4-Dichlor-5-aminoanthrachinon wird in die entsprechende Ogaminsäure übergeführt, diese nitriert, -#enseift und die eingeführte Nitrogruppe reduziert.
Durch Behandlung dieses 1,4-Dichlor-5,8-diaminoanthrachinons mit Benzoylchlorid erhält man das 1,4-Di- chlor-5,8-dibenzoylaminoanthrachinon. ,
Process for the production of an anthraquinone derivative. It has been found that a valuable anthraquinone derivative can be made using the trianthrimide of the formula
EMI0001.0005
treated with earba.zolierenden means. The new anthraquinone derivative is a vat dye that dissolves in concentrated sulfuric acid with a purple color and dyes cotton from a brown vat a strong gray-brown.
The trianthrimide used as starting material for the present process can, for example, be obtained from: 1,4 - dihalogen - 5,8 - dibenzoyldiaminoanthraehinones by reacting with 2 moles of 1-aminoanthraquinone in a known manner. Examples of carbazolating agents are aluminum chloride and titanium tetrachloride. 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 dimethyl'aniline, nitrobenzenes, ammonia, organic nitriles, organic and inorganic. Acid chlorides and sulfur dioxide can be used.
As far as hydrogen-rich compounds (hydro compounds) form in the treatment with carbazolizing agents, it is advantageous to subject the products obtained to an oxidizing treatment, which z. B. by treatment with AlkaJihypochl.oritlös@ung, with sodium nitrite solution in an acidic medium or with perborate solution.
<I> Example: </I> 22 parts of 1,4-Diehlor-5,8-dibenzoyldiamino-anthraquinone and 22 parts of 1-aminoanthraquinone are used together with 15 parts. Sodium carbonate, 2 parts of copper chloride and 300 parts of naphthalene were heated to the boil for 15 hours.
At 10-0, 600 parts of chlorobenzene are then added, the reaction product is filtered off cold, washed with chlorobenzene, the chlorobenzene is removed from the press cake with steam and the new compound is isolated by filtration. It dissolves in concentrated sulfuric acid with a grass-green color.
40 parts of ground, anhydrous aluminum chloride are slowly introduced into 80 parts of pyridine at 50-100. At around 100, 20 parts of the trianthrimide are then discharged into this melt. 1 mole of 1,4-diehlor-5,8-dibenzoyl'diaminoanthraquinone and 2 moles of 1-aminoanthraquinone.
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.
The above-mentioned 1,4-dichloro-5,8-di-benzoyl'diaminoanthraquinone can be obtained as follows: 1,4-dichloro-5-aminoanthraquinone is converted into the corresponding ogamic acid, this is nitrated, - # enseift and the introduced nitro group reduced.
Treatment of this 1,4-dichloro-5,8-diaminoanthraquinone with benzoyl chloride gives 1,4-dichloro-5,8-dibenzoylaminoanthraquinone. ,
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH258193T | 1943-03-23 | ||
| CH250662T | 1943-03-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH258193A true CH258193A (en) | 1948-11-15 |
Family
ID=25729473
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH258193D CH258193A (en) | 1943-03-23 | 1943-03-23 | Process for the production of an anthraquinone derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH258193A (en) |
-
1943
- 1943-03-23 CH CH258193D patent/CH258193A/en unknown
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