CA2076608A1 - Process for the preparation of 2,5-di (phenylamino)terephthalic acid and dialkyl esters thereof in high purity - Google Patents
Process for the preparation of 2,5-di (phenylamino)terephthalic acid and dialkyl esters thereof in high purityInfo
- Publication number
- CA2076608A1 CA2076608A1 CA002076608A CA2076608A CA2076608A1 CA 2076608 A1 CA2076608 A1 CA 2076608A1 CA 002076608 A CA002076608 A CA 002076608A CA 2076608 A CA2076608 A CA 2076608A CA 2076608 A1 CA2076608 A1 CA 2076608A1
- Authority
- CA
- Canada
- Prior art keywords
- reaction mixture
- phenylamino
- dialkyl
- oxygen
- terephthalic acid
- 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.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims abstract description 26
- 230000008569 process Effects 0.000 title claims abstract description 25
- ZJQZWNLKRBUEKX-UHFFFAOYSA-N 2,5-dianilinoterephthalic acid Chemical compound OC(=O)C=1C=C(NC=2C=CC=CC=2)C(C(=O)O)=CC=1NC1=CC=CC=C1 ZJQZWNLKRBUEKX-UHFFFAOYSA-N 0.000 title claims abstract description 18
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- 150000002148 esters Chemical class 0.000 title claims abstract description 10
- 239000011541 reaction mixture Substances 0.000 claims abstract description 32
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 23
- 239000007789 gas Substances 0.000 claims abstract description 23
- 239000001301 oxygen Substances 0.000 claims abstract description 23
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 23
- 238000005507 spraying Methods 0.000 claims abstract description 13
- 239000000725 suspension Substances 0.000 claims abstract description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 11
- 230000003647 oxidation Effects 0.000 claims abstract description 10
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 9
- PQOYAUVBHYFVOF-UHFFFAOYSA-N 2,5-dianilinocyclohexa-1,4-diene-1,4-dicarboxylic acid Chemical compound C1C(C(=O)O)=C(NC=2C=CC=CC=2)CC(C(O)=O)=C1NC1=CC=CC=C1 PQOYAUVBHYFVOF-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 6
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims abstract description 5
- 238000006356 dehydrogenation reaction Methods 0.000 claims abstract description 4
- 238000006243 chemical reaction Methods 0.000 claims description 16
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 13
- 239000008096 xylene Substances 0.000 claims description 13
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 12
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 5
- 230000003301 hydrolyzing effect Effects 0.000 claims description 3
- 230000001590 oxidative effect Effects 0.000 claims description 3
- -1 (C1-C2)alkyl succinate Chemical compound 0.000 claims description 2
- 238000006228 Dieckmann condensation reaction Methods 0.000 claims description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- 239000007859 condensation product Substances 0.000 claims description 2
- 238000000354 decomposition reaction Methods 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims 3
- 230000035484 reaction time Effects 0.000 abstract description 5
- 230000008901 benefit Effects 0.000 abstract description 4
- 230000002349 favourable effect Effects 0.000 abstract description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 10
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 8
- 239000007788 liquid Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 6
- 235000019260 propionic acid Nutrition 0.000 description 6
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 4
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 230000009850 completed effect Effects 0.000 description 4
- 230000000875 corresponding effect Effects 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 230000032258 transport Effects 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- ALPXOPKPVWQJMZ-UHFFFAOYSA-N dimethyl 2,5-bis(4-methylanilino)cyclohexa-1,4-diene-1,4-dicarboxylate Chemical compound C1C(C(=O)OC)=C(NC=2C=CC(C)=CC=2)CC(C(=O)OC)=C1NC1=CC=C(C)C=C1 ALPXOPKPVWQJMZ-UHFFFAOYSA-N 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 229940110728 nitrogen / oxygen Drugs 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- LTOQTEOVRRXGBX-UHFFFAOYSA-N 1,1,2,2,3,3-hexafluoropropane-1-sulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)(F)C(F)F LTOQTEOVRRXGBX-UHFFFAOYSA-N 0.000 description 1
- IAUKWGFWINVWKS-UHFFFAOYSA-N 1,2-di(propan-2-yl)naphthalene Chemical compound C1=CC=CC2=C(C(C)C)C(C(C)C)=CC=C21 IAUKWGFWINVWKS-UHFFFAOYSA-N 0.000 description 1
- CASWMOLTDVTXTM-UHFFFAOYSA-N 2,3-dianilinoterephthalic acid Chemical compound C=1C=CC=CC=1NC=1C(C(=O)O)=CC=C(C(O)=O)C=1NC1=CC=CC=C1 CASWMOLTDVTXTM-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 238000003512 Claisen condensation reaction Methods 0.000 description 1
- 241001024304 Mino Species 0.000 description 1
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- JAWHCRQIVXIBNR-UHFFFAOYSA-N dimethyl 2,5-dianilinocyclohexa-1,4-diene-1,4-dicarboxylate Chemical compound C1C(C(=O)OC)=C(NC=2C=CC=CC=2)CC(C(=O)OC)=C1NC1=CC=CC=C1 JAWHCRQIVXIBNR-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- 230000001131 transforming effect Effects 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/52—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C229/54—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C229/62—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring with amino groups and at least two carboxyl groups bound to carbon atoms of the same six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
- C07C227/16—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions not involving the amino or carboxyl groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP4127736.8 | 1991-08-22 | ||
| DE4127736 | 1991-08-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2076608A1 true CA2076608A1 (en) | 1993-02-23 |
Family
ID=6438803
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002076608A Abandoned CA2076608A1 (en) | 1991-08-22 | 1992-08-21 | Process for the preparation of 2,5-di (phenylamino)terephthalic acid and dialkyl esters thereof in high purity |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US5367096A (enExample) |
| EP (1) | EP0529498B1 (enExample) |
| JP (1) | JP3268018B2 (enExample) |
| KR (1) | KR930004249A (enExample) |
| BR (1) | BR9203289A (enExample) |
| CA (1) | CA2076608A1 (enExample) |
| DE (1) | DE59204414D1 (enExample) |
| ES (1) | ES2081533T3 (enExample) |
| MX (1) | MX9204868A (enExample) |
| TW (1) | TW226359B (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK0764630T3 (da) * | 1995-09-25 | 2002-01-14 | Ciba Sc Holding Ag | Fremgangsmåde til fremstilling af dialkylsuccinylsuccinater |
| JP4918950B2 (ja) * | 2001-01-16 | 2012-04-18 | Ｄｉｃ株式会社 | ２，５−ジアリールアミノテレフタル酸の製造方法 |
| AU2003266514A1 (en) * | 2002-09-17 | 2004-04-08 | Hirose Engineering Co., Ltd. | Luminescent compounds, process for the preparation thereof, and light emitting devices |
| WO2004067674A1 (ja) * | 2003-01-31 | 2004-08-12 | Hirose Engineering Co., Ltd. | 有機発光素子材料 |
| MY165153A (en) * | 2009-03-23 | 2018-02-28 | Univ Kansas | Spray process for selective oxidation |
| US8426639B2 (en) * | 2009-06-16 | 2013-04-23 | Amyris, Inc. | Preparation of trans, trans muconic acid and trans, trans muconates |
| BRPI1009655A2 (pt) | 2009-06-16 | 2016-08-09 | Amyris Inc | método e método para preparar um poliéster |
| US8415496B2 (en) | 2009-06-16 | 2013-04-09 | Amyris, Inc. | Biobased polyesters |
| BR112012016855A2 (pt) | 2010-01-08 | 2015-09-15 | Amyris Inc | "métodos para produzir isômeros de ácido mucônico e sais de muconato". |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3555087A (en) * | 1968-03-27 | 1971-01-12 | American Cyanamid Co | Terephthalamides |
| JPS5221499A (en) * | 1975-08-11 | 1977-02-18 | Santo Tekkosho Kk | Treating apparatus for wet heating and milling heat set |
| US4432940A (en) * | 1982-03-15 | 1984-02-21 | Allied Corporation | Reactor |
| DE3834747A1 (de) | 1988-10-12 | 1990-05-03 | Bayer Ag | Verfahren zur herstellung von 2,5-diarylaminoterephthalsaeuren |
| US5208365A (en) * | 1991-06-14 | 1993-05-04 | Hoechst Aktiengesellschaft | Process for the preparation of 2,5-di(phenylamino)-terephthalic acid and its dialkyl esters in high purity |
-
1992
- 1992-07-28 TW TW081105965A patent/TW226359B/zh active
- 1992-08-19 ES ES92114144T patent/ES2081533T3/es not_active Expired - Lifetime
- 1992-08-19 EP EP92114144A patent/EP0529498B1/de not_active Expired - Lifetime
- 1992-08-19 DE DE59204414T patent/DE59204414D1/de not_active Expired - Fee Related
- 1992-08-20 US US07/932,757 patent/US5367096A/en not_active Expired - Lifetime
- 1992-08-20 JP JP22173692A patent/JP3268018B2/ja not_active Expired - Fee Related
- 1992-08-21 MX MX9204868A patent/MX9204868A/es not_active IP Right Cessation
- 1992-08-21 BR BR929203289A patent/BR9203289A/pt not_active IP Right Cessation
- 1992-08-21 KR KR1019920015048A patent/KR930004249A/ko not_active Ceased
- 1992-08-21 CA CA002076608A patent/CA2076608A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| TW226359B (enExample) | 1994-07-11 |
| US5367096A (en) | 1994-11-22 |
| EP0529498A2 (de) | 1993-03-03 |
| EP0529498B1 (de) | 1995-11-22 |
| JPH05213841A (ja) | 1993-08-24 |
| KR930004249A (ko) | 1993-03-22 |
| ES2081533T3 (es) | 1996-03-16 |
| BR9203289A (pt) | 1993-04-06 |
| DE59204414D1 (de) | 1996-01-04 |
| JP3268018B2 (ja) | 2002-03-25 |
| MX9204868A (es) | 1993-07-01 |
| EP0529498A3 (en) | 1993-05-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |