JP3268018B2 - ２，５−ジ（フェニルアミノ）テレフタル酸およびそのジアルキルエステルを高純度で製造する方法 - Google Patents
２，５−ジ（フェニルアミノ）テレフタル酸およびそのジアルキルエステルを高純度で製造する方法Info
- Publication number
- JP3268018B2 JP3268018B2 JP22173692A JP22173692A JP3268018B2 JP 3268018 B2 JP3268018 B2 JP 3268018B2 JP 22173692 A JP22173692 A JP 22173692A JP 22173692 A JP22173692 A JP 22173692A JP 3268018 B2 JP3268018 B2 JP 3268018B2
- Authority
- JP
- Japan
- Prior art keywords
- phenylamino
- reaction mixture
- oxygen
- dialkyl
- nozzle
- 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 - Fee Related
Links
- 238000000034 method Methods 0.000 title claims description 27
- 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 description 8
- 150000002148 esters Chemical class 0.000 title claims description 8
- 239000011541 reaction mixture Substances 0.000 claims description 30
- 239000007789 gas Substances 0.000 claims description 23
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 18
- 239000001301 oxygen Substances 0.000 claims description 18
- 229910052760 oxygen Inorganic materials 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 239000000725 suspension Substances 0.000 claims description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 239000007921 spray Substances 0.000 claims description 9
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims description 8
- 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 description 7
- -1 (C 1 -C 2 ) alkyl succinate Chemical compound 0.000 claims description 6
- KETCAUHILOLXAD-UHFFFAOYSA-N 4-anilinooxycarbonylbenzoic acid Chemical compound C1=CC=C(C=C1)NOC(=O)C2=CC=C(C=C2)C(=O)O KETCAUHILOLXAD-UHFFFAOYSA-N 0.000 claims description 6
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- 230000003647 oxidation Effects 0.000 claims description 6
- 238000007254 oxidation reaction Methods 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 238000005507 spraying Methods 0.000 claims description 5
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims description 3
- 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 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 230000001590 oxidative effect Effects 0.000 claims description 3
- AAQNHCJFXINNHH-UHFFFAOYSA-N 2,5-dihydroxycyclohexa-1,3-diene-1,4-dicarboxylic acid Chemical compound OC1CC(C(O)=O)=C(O)C=C1C(O)=O AAQNHCJFXINNHH-UHFFFAOYSA-N 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
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- 239000007859 condensation product Substances 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
- 125000005907 alkyl ester group Chemical group 0.000 claims 1
- 229910001882 dioxygen Inorganic materials 0.000 claims 1
- AWDONTKPJRLLKH-UHFFFAOYSA-L disodium;2,5-dianilinoterephthalate Chemical compound [Na+].[Na+].[O-]C(=O)C=1C=C(NC=2C=CC=CC=2)C(C(=O)[O-])=CC=1NC1=CC=CC=C1 AWDONTKPJRLLKH-UHFFFAOYSA-L 0.000 claims 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 claims 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 12
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 11
- 239000000203 mixture Substances 0.000 description 9
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 8
- 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 6
- PBBXJBOFMIHTSC-UHFFFAOYSA-N 1,6-dioxecane-2,5,7,10-tetrone Chemical compound O=C1CCC(=O)OC(=O)CCC(=O)O1 PBBXJBOFMIHTSC-UHFFFAOYSA-N 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 230000035484 reaction time Effects 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
- 239000003054 catalyst Substances 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
- 239000011261 inert gas Substances 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 239000002904 solvent Substances 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
- 238000010586 diagram Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 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
- NGZJULVKWHXKMF-UHFFFAOYSA-N 2-anilinoterephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(NC=2C=CC=CC=2)=C1 NGZJULVKWHXKMF-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
- 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
- 229910000831 Steel Inorganic materials 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
- 239000003849 aromatic solvent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 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 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
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229940110728 nitrogen / oxygen Drugs 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 230000009469 supplementation Effects 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 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 |
|---|---|---|---|
| DE4127736 | 1991-08-22 | ||
| DE4127736:8 | 1991-08-22 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH05213841A JPH05213841A (ja) | 1993-08-24 |
| JP3268018B2 true JP3268018B2 (ja) | 2002-03-25 |
Family
ID=6438803
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP22173692A Expired - Fee Related JP3268018B2 (ja) | 1991-08-22 | 1992-08-20 | ２，５−ジ（フェニルアミノ）テレフタル酸およびそのジアルキルエステルを高純度で製造する方法 |
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". |
Citations (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 |
Family Cites Families (4)
| 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 |
| 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
Patent Citations (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 |
|---|---|
| TW226359B (enExample) | 1994-07-11 |
| US5367096A (en) | 1994-11-22 |
| EP0529498A2 (de) | 1993-03-03 |
| EP0529498B1 (de) | 1995-11-22 |
| CA2076608A1 (en) | 1993-02-23 |
| 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 |
| MX9204868A (es) | 1993-07-01 |
| EP0529498A3 (en) | 1993-05-12 |
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