CH366839A - Process for the preparation of quinacridones - Google Patents
Process for the preparation of quinacridonesInfo
- Publication number
- CH366839A CH366839A CH6044558A CH6044558A CH366839A CH 366839 A CH366839 A CH 366839A CH 6044558 A CH6044558 A CH 6044558A CH 6044558 A CH6044558 A CH 6044558A CH 366839 A CH366839 A CH 366839A
- Authority
- CH
- Switzerland
- Prior art keywords
- quin
- anthraquinone
- acridone
- dihydro
- parts
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title claims description 4
- FZEYVTFCMJSGMP-UHFFFAOYSA-N acridone Chemical class C1=CC=C2C(=O)C3=CC=CC=C3NC2=C1 FZEYVTFCMJSGMP-UHFFFAOYSA-N 0.000 claims description 19
- GDALETGZDYOOGB-UHFFFAOYSA-N Acridone Natural products C1=C(O)C=C2N(C)C3=CC=CC=C3C(=O)C2=C1O GDALETGZDYOOGB-UHFFFAOYSA-N 0.000 claims description 14
- JAJIPIAHCFBEPI-UHFFFAOYSA-N 9,10-dioxoanthracene-1-sulfonic acid Chemical class O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2S(=O)(=O)O JAJIPIAHCFBEPI-UHFFFAOYSA-N 0.000 claims description 8
- 230000003647 oxidation Effects 0.000 claims description 7
- 238000007254 oxidation reaction Methods 0.000 claims description 7
- OKONMFPEKSWGEU-UHFFFAOYSA-N 9,10-dioxoanthracene-2,7-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 OKONMFPEKSWGEU-UHFFFAOYSA-N 0.000 claims description 4
- 239000007800 oxidant agent Substances 0.000 claims description 4
- 239000012670 alkaline solution Substances 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 239000005077 polysulfide Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- PDKNKWRYRJPPPO-UHFFFAOYSA-N 9,10-dioxoanthracene-1,2,3-trisulfonic acid Chemical class O=C1C2=CC=CC=C2C(=O)C2=C1C=C(S(=O)(=O)O)C(S(O)(=O)=O)=C2S(O)(=O)=O PDKNKWRYRJPPPO-UHFFFAOYSA-N 0.000 description 1
- OZTBHAGJSKTDGM-UHFFFAOYSA-N 9,10-dioxoanthracene-1,5-disulfonic acid Chemical compound O=C1C=2C(S(=O)(=O)O)=CC=CC=2C(=O)C2=C1C=CC=C2S(O)(=O)=O OZTBHAGJSKTDGM-UHFFFAOYSA-N 0.000 description 1
- SROYVYGZVXMVOA-UHFFFAOYSA-N 9,10-dioxoanthracene-1,6-disulfonic acid Chemical compound O=C1C2=CC(S(=O)(=O)O)=CC=C2C(=O)C2=C1C=CC=C2S(O)(=O)=O SROYVYGZVXMVOA-UHFFFAOYSA-N 0.000 description 1
- VNIFUVUQZVMDER-UHFFFAOYSA-N 9,10-dioxoanthracene-1,7-disulfonic acid Chemical compound C1=CC(S(O)(=O)=O)=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 VNIFUVUQZVMDER-UHFFFAOYSA-N 0.000 description 1
- IJNPIHLZSZCGOC-UHFFFAOYSA-N 9,10-dioxoanthracene-1,8-disulfonic acid Chemical compound O=C1C2=CC=CC(S(O)(=O)=O)=C2C(=O)C2=C1C=CC=C2S(=O)(=O)O IJNPIHLZSZCGOC-UHFFFAOYSA-N 0.000 description 1
- MMNWSHJJPDXKCH-UHFFFAOYSA-N 9,10-dioxoanthracene-2-sulfonic acid Chemical compound C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 MMNWSHJJPDXKCH-UHFFFAOYSA-N 0.000 description 1
- XUINISXRACTVNW-UHFFFAOYSA-N 9,10-dioxoanthracene-2-sulfonic acid;sodium Chemical compound [Na].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 XUINISXRACTVNW-UHFFFAOYSA-N 0.000 description 1
- HEHRNSLVOYMYIM-UHFFFAOYSA-N C1(=C(C(=C(C=2C(C3=CC=CC=C3C(C12)=O)=O)S(=O)(=O)O)S(=O)(=O)O)S(=O)(=O)O)S(=O)(=O)O Chemical class C1(=C(C(=C(C=2C(C3=CC=CC=C3C(C12)=O)=O)S(=O)(=O)O)S(=O)(=O)O)S(=O)(=O)O)S(=O)(=O)O HEHRNSLVOYMYIM-UHFFFAOYSA-N 0.000 description 1
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical class N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 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 description 1
- 239000001000 anthraquinone dye Substances 0.000 description 1
- MSSUFHMGCXOVBZ-UHFFFAOYSA-N anthraquinone-2,6-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 MSSUFHMGCXOVBZ-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- HYHCSLBZRBJJCH-UHFFFAOYSA-N sodium polysulfide Polymers [Na+].S HYHCSLBZRBJJCH-UHFFFAOYSA-N 0.000 description 1
- LJRGBERXYNQPJI-UHFFFAOYSA-M sodium;3-nitrobenzenesulfonate Chemical compound [Na+].[O-][N+](=O)C1=CC=CC(S([O-])(=O)=O)=C1 LJRGBERXYNQPJI-UHFFFAOYSA-M 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
- C09B48/00—Quinacridones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Description
Verfahren zur Herstellung von Chinaeridonen Es wurde gefunden, dass man die bekannte Her stellung von Chin[2,3-b]acridonen aus 6,13-Dihydro-
EMI0001.0004
in einem neuen Verfahren mit Anthrachinonsulfon- säuren als Oxydationsmittel durchführen kann.
Gegenstand des vorliegenden Patentes ist daher ein Verfahren zur Herstellung von Chin[2,3-b]acri- donen durch Oxydation von 6,13-Dihydro-chin- [2,3-b]acridonen in alkalischer Lösung, dadurch ge kennzeichnet, dass man Anthrachinonsulfonsäuren oder ihre Salze als Oxydationsmittel verwendet. Dabei können nichtsubstituierte oder auch substi tuierte 6,13-Dihydro-chin[2,3-b]acridone oxydiert werden, wie z.
B. Dichlor-, Tetrachlor-, Diphenyl- und insbesondere Dimethyl-6,13-dihydro-chin[2,3-b]- acridone.
Von den Anthrachinonsulfonsäuren, die vorteil haft in Form ihrer Natriumsalze verwendet werden, kommen in Frage: Anthrachinon-l-sulfonsäure, Anthrachinon-2-sulfonsäure, Anthrachinon-1,5-disulfonsäure, Anthrachinon-1,6-disulfonsäure, Anthrachinon-1,7-disulfonsäure, Anthrachinon-1, 8-disulfonsäure, Anthrachinon-2,6-disulfonsäure und vor allem Anthrachinon-2,7-disulfonsäure. chin[2,
3-b]acridonen durch Oxydation nach dem Re aktionsschema Ausserdem können auch Anthrachinontrisulfonsäuren und Anthrachinontetrasulfonsäuren verwendet werden.
Die Oxydation wird gemäss vorliegendem Ver fahren wie gesagt in alkalischer Lösung, vorzugs weise in alkoholischer Kaliumhydroxyd- oder Na triumhydroxydlösung, durchgeführt. Als Lösungs mittel können die verschiedensten Lösungsmittel, wie Methanol, Äthylalkohol, Propylalkohol, Butylalkohol, Glykole, vorzugsweise in Form von Alkalialkohola- ten, und Aceton usw., verwendet werden.
Die auf diese Weise hergestellten Chinacridone können in ausgezeichneter Ausbeute und in reiner Form erhalten werden.
Es ist bekannt, die Oxydation mit m-nitrobenzol- sulfonsaurem Natrium, Polysulfid oder Sauerstoff durchzuführen, jedoch verläuft die Reaktion mit Sauerstoff und Polysulfid nur mit unbefriedigender Ausbeute. Es war nun überraschend, festzustellen, dass die Oxydation mit Anthrachinonsulfonsäuren glatt und mit sehr guter Ausbeute durchführbar ist. Dabei wird das Anthrachinonderivat in seine Leuko- verbindung übergeführt.
Diese kann ohne weiteres durch Luftsauerstoff wieder vollständig zur Anthra- chinonsulfonsäure regeneriert und diese somit fast beliebig lang verwendet werden. Von ganz besonders praktischem Wert jedoch ist die Tatsache, dass auf diese Weise bisher für wertlos gehaltene Verbindun gen, wie z. B. Anthrachinon - 2,7 - disulfonsäure, welche bei der Herstellung von Anthrachinonfarb- stoffen in grosser Menge anfallen, verwendet werden können.
Es war keineswegs naheliegend, dass die Oxyda tion erfindungsgemäss mit nicht üblichen und so schwachen Oxydationsmitteln, das heisst mit Anthra- chinonsulfonsäuren oder ihren Salzen, durchführbar ist.
Gegenüber dem bekannten, nichtsubstituierten Chin[2,3-b]acridon besitzt das erfindungsgemäss her gestellte, nicht substituierte Chin[2,3-b]acridon eine andere Modifikation, die durch ein abweichendes Röntgendiagramm gekennzeichnet ist und ausgezeich nete Eigenschaften aufweist. Immerhin zeigen das be kannte Chin[2,3-b]acridon und das erfindungsgemäss hergestellte Chin[2,3-b]acridon praktisch denselben roten Farbton.
Im nachfolgenden Beispiel bedeuten die Teile, sofern nichts anderes angegeben wird, Gewichtsteile, die Prozente Gewichtsprozente, und die Tempera turen sind in Celsiusgraden angegeben.
<I>Beispiel 1</I> 3,14 Teile 6,13-Dihydro-chin[2,3-b]acridon wer den in 100 Teilen Äthanol und 2 Teilen Kalium hydroxyd am Rückfluss erhitzt. Dann lässt man eine Lösung von 6,3 Teilen Anthrachinon-2,7-disulfon- säure als Natriumsalz in 20 Teilen Wasser langsam dazutropfen. Anschliessend kocht man noch 2 Stun den am Rückfluss und filtriert das ausgefallene Pro dukt ab. Es wird mit Wasser und Alkohol gewaschen.
Man erhält 3,04 Teile eines hellroten Pulvers von Chin[2,3-b]acridon. An Stelle von 6,13-Dihydro-chin[2,3-b]acridon kann 2,9-Diphenyl-6,13-dihydro-chin[2,3-b]acridon, 2,4,9,11-Tetrachlor-6,13-dihydro-chin[2,3-b]- acridon, 3,10-Dichlor-6,13-dihydro-chin[2,3-b]acridon und 2,3,9,10-Tetrachlor-6,13-dihydro-chin[2,3-b]- acridon verwendet und zum entsprechenden Chinacridon- derivat oxydiert werden.
<I>Beispiel 2</I> 3,42 Teile 2,9-Dimethyl-6,13-dihydro-chin[2,3-b]- acridon werden in 100 Teilen Äthylalkohol und 2 Teilen Natriumhydroxyd am Rückfluss erhitzt; dann lässt man 6,2 Teile anthrachinon-2-sulfonsaures Natrium, in 36 Teilen heissem Wasser gelöst, zu tropfen. Anschliessend erhitzt man noch 8 Stunden am Rückfluss und isoliert das ausgefallene 2,9-Di- methyl-chin[2,3-b]acridon, wie im Beispiel 1 ange geben.
Process for the preparation of quinaeridones It has been found that the known Her position of quin [2,3-b] acridones from 6,13-dihydro-
EMI0001.0004
in a new process with anthraquinonesulfonic acids as oxidizing agent.
The subject of the present patent is therefore a process for the preparation of quin [2,3-b] acridones by oxidation of 6,13-dihydro-quin- [2,3-b] acridones in alkaline solution, characterized in that one uses anthraquinone sulfonic acids or their salts as oxidizing agents. In this case, unsubstituted or substituted 6,13-dihydro-quin [2,3-b] acridones can be oxidized, such as.
B. dichloro-, tetrachloro-, diphenyl- and especially dimethyl-6,13-dihydro-quin [2,3-b] - acridone.
Of the anthraquinone sulfonic acids that are advantageously used in the form of their sodium salts, there are: anthraquinone-1-sulfonic acid, anthraquinone-2-sulfonic acid, anthraquinone-1,5-disulfonic acid, anthraquinone-1,6-disulfonic acid, anthraquinone-1, 7-disulfonic acid, anthraquinone-1, 8-disulfonic acid, anthraquinone-2,6-disulfonic acid and especially anthraquinone-2,7-disulfonic acid. chin [2,
3-b] acridones by oxidation according to the reaction scheme. Anthraquinone trisulfonic acids and anthraquinone tetrasulfonic acids can also be used.
According to the present process, the oxidation is carried out, as I said, in an alkaline solution, preferably in an alcoholic potassium hydroxide or sodium hydroxide solution. A wide variety of solvents, such as methanol, ethyl alcohol, propyl alcohol, butyl alcohol, glycols, preferably in the form of alkali alcohols, and acetone, etc., can be used as solvents.
The quinacridones prepared in this way can be obtained in excellent yield and in pure form.
It is known to carry out the oxidation with sodium m-nitrobenzenesulfonate, polysulfide or oxygen, but the reaction with oxygen and polysulfide proceeds only with unsatisfactory yield. It was now surprising to find that the oxidation with anthraquinonesulphonic acids can be carried out smoothly and with a very good yield. The anthraquinone derivative is converted into its leuco compound.
This can easily be completely regenerated to anthraquinone sulfonic acid by atmospheric oxygen and this can therefore be used for almost any length of time. Of particular practical value, however, is the fact that in this way connections that were previously considered worthless, such as. B. Anthraquinone - 2,7 - disulfonic acid, which are produced in large quantities in the production of anthraquinone dyes, can be used.
It was by no means obvious that the oxidation according to the invention can be carried out with unusual and so weak oxidizing agents, that is to say with anthraquinone sulfonic acids or their salts.
Compared to the known, unsubstituted quin [2,3-b] acridone, the unsubstituted quin [2,3-b] acridone produced according to the invention has a different modification which is characterized by a different X-ray diagram and has excellent properties. After all, the known quin [2,3-b] acridone and the quin [2,3-b] acridone prepared according to the invention show practically the same red color.
In the following example, unless otherwise stated, the parts are parts by weight, the percentages are percentages by weight, and the temperatures are given in degrees Celsius.
<I> Example 1 </I> 3.14 parts of 6,13-dihydro-quin [2,3-b] acridone who heated to reflux in 100 parts of ethanol and 2 parts of potassium hydroxide. Then a solution of 6.3 parts of anthraquinone-2,7-disulfonic acid as the sodium salt in 20 parts of water is slowly added dropwise. It is then refluxed for a further 2 hours and the precipitated product is filtered off. It is washed with water and alcohol.
3.04 parts of a light red powder of quin [2,3-b] acridone are obtained. Instead of 6,13-dihydro-quin [2,3-b] acridone, 2,9-diphenyl-6,13-dihydro-quin [2,3-b] acridone, 2,4,9,11-tetrachlor -6,13-dihydro-quin [2,3-b] -acridone, 3,10-dichloro-6,13-dihydro-quin [2,3-b] acridone and 2,3,9,10-tetrachloro- 6,13-dihydro-quin [2,3-b] acridone can be used and oxidized to the corresponding quinacridone derivative.
<I> Example 2 </I> 3.42 parts of 2,9-dimethyl-6,13-dihydro-quin [2,3-b] acridone are refluxed in 100 parts of ethyl alcohol and 2 parts of sodium hydroxide; then 6.2 parts of sodium anthraquinone-2-sulfonic acid, dissolved in 36 parts of hot water, are added dropwise. The mixture is then refluxed for a further 8 hours and the precipitated 2,9-dimethyl-quin [2,3-b] acridone is isolated, as given in Example 1.
Claims (1)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH6044558A CH366839A (en) | 1958-06-11 | 1958-06-11 | Process for the preparation of quinacridones |
| ES0250032A ES250032A1 (en) | 1958-06-11 | 1959-06-10 | Procedure for the preparation of quinacridones based on 6,13-dihydroquinocridones (Machine-translation by Google Translate, not legally binding) |
| NL240061A NL105115C (en) | 1958-06-11 | 1959-06-11 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH6044558A CH366839A (en) | 1958-06-11 | 1958-06-11 | Process for the preparation of quinacridones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH366839A true CH366839A (en) | 1963-01-31 |
Family
ID=4522947
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH6044558A CH366839A (en) | 1958-06-11 | 1958-06-11 | Process for the preparation of quinacridones |
Country Status (3)
| Country | Link |
|---|---|
| CH (1) | CH366839A (en) |
| ES (1) | ES250032A1 (en) |
| NL (1) | NL105115C (en) |
-
1958
- 1958-06-11 CH CH6044558A patent/CH366839A/en unknown
-
1959
- 1959-06-10 ES ES0250032A patent/ES250032A1/en not_active Expired
- 1959-06-11 NL NL240061A patent/NL105115C/nl active
Also Published As
| Publication number | Publication date |
|---|---|
| ES250032A1 (en) | 1960-01-01 |
| NL105115C (en) | 1963-01-15 |
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