GB975466A - Process for the production of 2,5-diarylamino-terephthalic acids - Google Patents
Process for the production of 2,5-diarylamino-terephthalic acidsInfo
- Publication number
- GB975466A GB975466A GB1015462A GB1015462A GB975466A GB 975466 A GB975466 A GB 975466A GB 1015462 A GB1015462 A GB 1015462A GB 1015462 A GB1015462 A GB 1015462A GB 975466 A GB975466 A GB 975466A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- diarylamino
- terephthalic acid
- terephthalic
- chloranilido
- 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.)
- Expired
Links
- 239000002253 acid Substances 0.000 abstract 6
- 150000002148 esters Chemical class 0.000 abstract 4
- 230000003647 oxidation Effects 0.000 abstract 3
- 238000007254 oxidation reaction Methods 0.000 abstract 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 abstract 2
- YYVYAPXYZVYDHN-UHFFFAOYSA-N 9,10-phenanthroquinone Chemical compound C1=CC=C2C(=O)C(=O)C3=CC=CC=C3C2=C1 YYVYAPXYZVYDHN-UHFFFAOYSA-N 0.000 abstract 2
- 230000001476 alcoholic effect Effects 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- 238000002360 preparation method Methods 0.000 abstract 2
- 239000011541 reaction mixture Substances 0.000 abstract 2
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 abstract 1
- FVLUGNOOEZYDNV-UHFFFAOYSA-N 2,5-bis(4-methylanilino)terephthalic acid Chemical compound C1=CC(C)=CC=C1NC(C(=C1)C(O)=O)=CC(C(O)=O)=C1NC1=CC=C(C)C=C1 FVLUGNOOEZYDNV-UHFFFAOYSA-N 0.000 abstract 1
- 229930192627 Naphthoquinone Natural products 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 150000004982 aromatic amines Chemical class 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000000975 dye Substances 0.000 abstract 1
- 150000002791 naphthoquinones Chemical class 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- -1 phenanthrene-quinone- and naphthoquinone-carboxylic acids Chemical class 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 238000007127 saponification reaction Methods 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 abstract 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
2,5-Diarylamino-terephthalic acids are prepared by the simultaneous oxidation and saponification of the corresponding 2,5-diarylamino-3, 6-dihydro-terephthalic acid dialkyl esters with aqueous alcoholic dyes and atmospheric oxygen at a temperature not exceeding the reflux temperature of the reaction mixture in the presence of less than 10% by wt. of an oxidation catalyst and then acidifying the product to obtain the free acid. Suitable oxidation catalysts specified are anthroquinone, phenanthrene-quinone, naphthoquinone, chloranil, naphthoquinone-, anthraquinone-, and phenanthrene-quinone sulphonic acids, and anthraquinone-, phenanthrene-quinone- and naphthoquinone-carboxylic acids. The reaction mixture obtained in the preparation of the 2,5-diarylamino-3, 6-dihydroterephthalic acid dialkyl esters from the reaction of 1 mol of succinylosuccinic acid dialkyl acid ester with 2 mols of an arylamine in alcoholic solution, may be used as the starting material instead of the isolated 2,5-diarylamino-3, 6-dihydro-terephthalic acid dialkyl esters. Six examples are given, illustrating the preparation of 2,5-dianilido-terephthalic; acid; 2,5-di-(p-toluidino)-terephthalic acid; 2,5-di-(o-chloranilido)-terephthalic acid; 2,5-di-(p-chloranilido)-terephthalic acid; 2, 5-di-(31, 41-di-chloranilido)-terephthalic acid; and 2, 5-di-(p-phenetrolino)-terephthalic acid respectively.
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 |
|---|---|
| GB975466A true GB975466A (en) | 1964-11-18 |
Family
ID=25969392
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1015462A Expired GB975466A (en) | 1961-03-17 | 1962-03-16 | Process for the production of 2,5-diarylamino-terephthalic acids |
Country Status (3)
| Country | Link |
|---|---|
| CH (1) | CH397715A (en) |
| DE (2) | DE1144285B (en) |
| GB (1) | GB975466A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4435589A (en) | 1981-02-10 | 1984-03-06 | Bayer Aktiengesellschaft | Process for the preparation of dimethyl succinylosuccinate, the disodium salt thereof, dianilinodihydroterephthalic acids, the dimethyl esters and salts thereof, and dianilinoterephthalic acids, and the dimethyl esters and salts thereof |
| US4981997A (en) * | 1988-10-12 | 1991-01-01 | Bayer Aktiengesellschaft | Process for the preparation of 2,5-diarylaminoterephthalic acids |
-
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 (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4435589A (en) | 1981-02-10 | 1984-03-06 | Bayer Aktiengesellschaft | Process for the preparation of dimethyl succinylosuccinate, the disodium salt thereof, dianilinodihydroterephthalic acids, the dimethyl esters and salts thereof, and dianilinoterephthalic acids, and the dimethyl esters and salts thereof |
| US4981997A (en) * | 1988-10-12 | 1991-01-01 | Bayer Aktiengesellschaft | Process for the preparation of 2,5-diarylaminoterephthalic acids |
| EP0363756A3 (en) * | 1988-10-12 | 1991-03-27 | Bayer Ag | Method for the preparation of 2,5-diarylamino-terephthalic acids |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1144285B (en) | 1963-02-28 |
| DE1147953B (en) | 1963-05-02 |
| CH397715A (en) | 1965-08-31 |
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