DE1147953B - Process for the preparation of 2, 5-diarylaminoterephthalic acids - Google Patents
Process for the preparation of 2, 5-diarylaminoterephthalic acidsInfo
- Publication number
- DE1147953B DE1147953B DEC24761A DEC0024761A DE1147953B DE 1147953 B DE1147953 B DE 1147953B DE C24761 A DEC24761 A DE C24761A DE C0024761 A DEC0024761 A DE C0024761A DE 1147953 B DE1147953 B DE 1147953B
- Authority
- DE
- Germany
- Prior art keywords
- acids
- parts
- anthraquinone
- phenanthrenequinone
- naphthoquinone
- 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.)
- Pending
Links
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
DEUTSCHESGERMAN
PATENTAMTPATENT OFFICE
BEKANNTMACHUNG
DER ANMELDUNG
UNDAUSGABE DER
AUSLEGESCHRIFT:NOTICE
THE REGISTRATION
AND ISSUE OF THE EDITING LETTER :
C24761IVb/12qC24761IVb / 12q
1. AUGUST 1961AUGUST 1, 1961
2. MAI 1963MAY 2, 1963
Das Verfahren der Patentanmeldung C 23672 IVb/ 12 q (deutsche Auslegeschrift 1144 285) betrifft die Herstellung von 2,5-Diarylaminoterephthalsäuren aus 2,5-Diarylamino-3,6-dihydro-terephthalsäuredialkylestern durch gleichzeitige Einwirkung von wäßrigalkoholischen Laugen und Luftsauerstoff bei erhöhter Temperatur, welches dadurch gekennzeichnet ist, daß man der Reaktionsmischung geringe Mengen von Chinonsulfonsäuren, wie Naphthochinon-, Anthrachinon- und Phenanthrenchinonsulfonsäuren, als Sauerstoffüberträger zusetzt.The method of patent application C 23672 IVb / 12 q (German Auslegeschrift 1144 285) relates to Production of 2,5-diarylaminoterephthalic acids from 2,5-diarylamino-3,6-dihydro-terephthalic acid dialkyl esters due to the simultaneous action of aqueous alcoholic alkalis and atmospheric oxygen at increased Temperature, which is characterized in that the reaction mixture is small amounts of Quinone sulfonic acids, such as naphthoquinone, anthraquinone and phenanthrenequinone sulfonic acids, as Oxygen carrier clogs.
In weiterer Ausbildung dieses Erfindungsgedankens wurde nun gefunden, daß man als Sauerstoffüberträger mit gleichem Erfolg auch die den Chinonsulfonsäuren zugrunde liegenden Chinone selbst, wie z. B. Anthrachinon, Phenanthrenchinon, Naphthochinon, Chloranil oder Chinoncarbonsäuren, wie Anthrachinon-, Phenanthrenchinon- oder Naphthochinoncarbonsäuren, verwenden kann.In a further development of this inventive concept it has now been found that the oxygen carrier with the same success the quinones themselves on which the quinonesulfonic acids are based, such as z. B. anthraquinone, phenanthrenequinone, naphthoquinone, chloranil or quinonecarboxylic acids, such as Anthraquinone, phenanthrenequinone or naphthoquinone carboxylic acids, may use.
In 460 Teile n-Butanol werden 122 Teile 2,5-Di-(3',4' - dichloranilino) - 3,6 - dihydro-terephthalsäurediäthylester, 331 Teile 23%ige Natronlauge und 5 Teile Phenanthrenchinon (oder gleiche Teile Anthrachinon, Chloranil, a-Naphthochinon) eingetragen. Unter Einleiten von Luft wird dann 2 Stunden auf 80 bis 90° C erhitzt. Dann werden etwa 950 Teile eines azeotropen Gemisches (n-Butanol—Wasser) vom Kp. 92° C abdestilliert, wobei man im Verlauf der Destillation gleichzeitig etwa 900 Teile Wasser zulaufen läßt. Die weitere Aufarbeitung kann nach zwei Methoden erfolgen: 122 parts of 2,5-di- (3 ', 4' - dichloroanilino) - 3,6 - dihydro-terephthalic acid diethyl ester, 331 parts of 23% sodium hydroxide solution and 5 parts Phenanthrenequinone (or equal parts anthraquinone, chloranil, a-naphthoquinone) entered. Under initiation air is then heated to 80 to 90 ° C. for 2 hours. Then about 950 parts of an azeotropic Mixture (n-butanol-water) with a boiling point of 92 ° C distilled off, about 900 parts of water are allowed to run in at the same time in the course of the distillation. the further work-up can be carried out using two methods:
a) Die verbleibende Reaktionslösung wird mit etwa 392 Teilen 25%iger Schwefelsäure kongosauer gestellt, das ausgefällte Produkt wird abgesaugt, mit Wasser neutral gewaschen und getrocknet. Man erhält so 98 Teile (= 91% der Theorie) 2,5-Di-(3',4/-dichloranilino)-terephthalsäure vom Schmelzpunkt 346° C in Form eines violetten kristallinen Pulvers.a) The remaining reaction solution is made Congo acidic with about 392 parts of 25% sulfuric acid, the precipitated product is filtered off with suction, washed neutral with water and dried. 98 parts (= 91% of theory) of 2,5-di- (3 ', 4 / -dichloroanilino) -terephthalic acid with a melting point of 346 ° C. are thus obtained in the form of a violet crystalline powder.
b) Nach Abkühlen und mehrstündigem Stehen wird das aus der Reaktionslösung auskristallisierte gelbe Dinatriumsalz abgesaugt, mit gesättigter Kochsalzlösung gewaschen, in etwa 1500 Teilen heißem Wasser gelöst und mit etwa 45 Teilen 50%iger Schwefelsäure kongosauer gestellt. Dann wird abgesaugt, mit Wasser neutral gewaschen und getrocknet, wobei man 98 Teile (= 91% der Theorie) 2,5-Di-(3',4'-dicHorardlino)-terephthalsäure vom Schmelzpunkt 346° C erhält.b) After cooling and standing for several hours, the crystallized from the reaction solution yellow disodium salt filtered off with suction, washed with saturated sodium chloride solution, in about 1500 parts Dissolved hot water and made Congo acidic with about 45 parts of 50% sulfuric acid. then is filtered off with suction, washed neutral with water and dried, 98 parts (= 91% of theory) 2,5-di- (3 ', 4'-dicHorardlino) -terephthalic acid obtained with a melting point of 346 ° C.
Verfahren zur Herstellung von 2,5-DiarylaminoterephthalsäurenProcess for the preparation of 2,5-diarylaminoterephthalic acids
Zusatz zur Patentanmeldung C 23672 IVb/12 q (Deutsche Auslegeschrift 1144 285)Addition to patent application C 23672 IVb / 12 q (German Auslegeschrift 1144 285)
Anmelder:
Cassella Farbwerke MainkurApplicant:
Cassella Farbwerke Mainkur
Aktiengesellschaft, Frankfurt/M.- FechenheimAktiengesellschaft, Frankfurt / M.- Fechenheim
Dr. Werner Zerweck, Frankfurt/M.,Dr. Werner Zerweck, Frankfurt / M.,
Dr. Heinrich Ritter, Dörnigheim (Kr. Hanau), und Dr. Erwin Herrmann, Frankfurt/M., sind als Erfinder genannt wordenDr. Heinrich Ritter, Dörnigheim (Kr. Hanau), and Dr. Erwin Herrmann, Frankfurt / M., have been named as inventors
In 460 Teile Äthylenglykol werden 111 Teile 2,5-Di-(p-phenetidino) - 3,6 - dihydro - terephthalsäurediäthylester, 331 Teile 23%ige Natronlauge und 5 Teile Anthrachinon-2-carbonsäure eingetragen und unter Einleiten von Luft 3 Stunden auf 120 bis 130° C erhitzt. Dann wird mit etwa 179 Teilen 50%iger Schwefelsäure kongosauer gestellt, das ausgefällte Produkt wird abgesaugt, mit warmem Wasser neutral gewaschen und getrocknet. Man erhält so 88 Teile (= 90% der Theorie) 2,5-Di-(p-phenetidino)-terephthalsäure vom Schmelzpunkt 315° C in Form eines blauvioletten kristallinen Pulvers.In 460 parts of ethylene glycol 111 parts of 2,5-di- (p-phenetidino) - 3,6 - dihydro - terephthalic acid diethyl ester, 331 parts of 23% sodium hydroxide solution and 5 parts of anthraquinone-2-carboxylic acid entered and below Passing in air heated to 120 to 130 ° C for 3 hours. Then it is 50% with about 179 parts Sulfuric acid made acidic to the Congo, the precipitated product is filtered off with suction and neutralized with warm water washed and dried. 88 parts (= 90% of theory) of 2,5-di- (p-phenetidino) -terephthalic acid are obtained in this way with a melting point of 315 ° C in the form of a blue-violet crystalline powder.
Claims (1)
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEC23672A DE1144285B (en) | 1961-03-17 | 1961-03-17 | Process for the preparation of 2, 5-diarylaminoterephthalic acids |
DEC24761A DE1147953B (en) | 1961-03-17 | 1961-08-01 | Process for the preparation of 2, 5-diarylaminoterephthalic acids |
CH313362A CH397715A (en) | 1961-03-17 | 1962-03-15 | Process for the preparation of 2,5-diarylaminoterephthalic acids |
GB1015462A GB975466A (en) | 1961-03-17 | 1962-03-16 | Process for the production of 2,5-diarylamino-terephthalic acids |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEC23672A DE1144285B (en) | 1961-03-17 | 1961-03-17 | Process for the preparation of 2, 5-diarylaminoterephthalic acids |
DEC24761A DE1147953B (en) | 1961-03-17 | 1961-08-01 | Process for the preparation of 2, 5-diarylaminoterephthalic acids |
Publications (1)
Publication Number | Publication Date |
---|---|
DE1147953B true DE1147953B (en) | 1963-05-02 |
Family
ID=25969392
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DEC23672A Pending DE1144285B (en) | 1961-03-17 | 1961-03-17 | Process for the preparation of 2, 5-diarylaminoterephthalic acids |
DEC24761A Pending DE1147953B (en) | 1961-03-17 | 1961-08-01 | Process for the preparation of 2, 5-diarylaminoterephthalic acids |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DEC23672A Pending DE1144285B (en) | 1961-03-17 | 1961-03-17 | Process for the preparation of 2, 5-diarylaminoterephthalic acids |
Country Status (3)
Country | Link |
---|---|
CH (1) | CH397715A (en) |
DE (2) | DE1144285B (en) |
GB (1) | GB975466A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4981997A (en) * | 1988-10-12 | 1991-01-01 | Bayer Aktiengesellschaft | Process for the preparation of 2,5-diarylaminoterephthalic acids |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3104644A1 (en) | 1981-02-10 | 1982-08-19 | Bayer Ag, 5090 Leverkusen | METHOD FOR PRODUCING DIMETHYLSUCCINYLOSUCCINATE, ITS DIATILIUM SALTS, DIANILINODIHYDROTEREPHTHALIC ACIDS, THEIR DIMETHYL ESTERS AND SALTS, AND DIANILINOTEREPHTHALIC ACIDS, THEIR DIMETHYLS |
-
1961
- 1961-03-17 DE DEC23672A patent/DE1144285B/en active Pending
- 1961-08-01 DE DEC24761A patent/DE1147953B/en active Pending
-
1962
- 1962-03-15 CH CH313362A patent/CH397715A/en unknown
- 1962-03-16 GB GB1015462A patent/GB975466A/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4981997A (en) * | 1988-10-12 | 1991-01-01 | Bayer Aktiengesellschaft | Process for the preparation of 2,5-diarylaminoterephthalic acids |
Also Published As
Publication number | Publication date |
---|---|
GB975466A (en) | 1964-11-18 |
DE1144285B (en) | 1963-02-28 |
CH397715A (en) | 1965-08-31 |
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