UA79640C2 - A method for making adipinic acid - Google Patents
A method for making adipinic acid Download PDFInfo
- Publication number
- UA79640C2 UA79640C2 UAA200504096A UA2005004096A UA79640C2 UA 79640 C2 UA79640 C2 UA 79640C2 UA A200504096 A UAA200504096 A UA A200504096A UA 2005004096 A UA2005004096 A UA 2005004096A UA 79640 C2 UA79640 C2 UA 79640C2
- Authority
- UA
- Ukraine
- Prior art keywords
- acid
- acids
- medium
- oxidation
- hydrolysis
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 46
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 title claims abstract description 44
- 229960000250 adipic acid Drugs 0.000 title 1
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 65
- 230000003647 oxidation Effects 0.000 claims abstract description 52
- 150000002148 esters Chemical class 0.000 claims abstract description 27
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 25
- 239000001301 oxygen Substances 0.000 claims abstract description 25
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 25
- 239000001361 adipic acid Substances 0.000 claims abstract description 21
- 235000011037 adipic acid Nutrition 0.000 claims abstract description 21
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims abstract description 17
- 230000001590 oxidative effect Effects 0.000 claims abstract description 14
- 239000007789 gas Substances 0.000 claims abstract description 12
- 239000002253 acid Substances 0.000 claims description 63
- 230000007062 hydrolysis Effects 0.000 claims description 39
- 238000006460 hydrolysis reaction Methods 0.000 claims description 39
- 239000002904 solvent Substances 0.000 claims description 39
- 150000007513 acids Chemical class 0.000 claims description 33
- 239000012429 reaction media Substances 0.000 claims description 28
- 238000000926 separation method Methods 0.000 claims description 28
- 150000001875 compounds Chemical class 0.000 claims description 25
- 239000003054 catalyst Substances 0.000 claims description 24
- 238000000605 extraction Methods 0.000 claims description 24
- 239000012074 organic phase Substances 0.000 claims description 17
- 238000004821 distillation Methods 0.000 claims description 16
- 238000009835 boiling Methods 0.000 claims description 13
- 238000001556 precipitation Methods 0.000 claims description 12
- 150000001298 alcohols Chemical class 0.000 claims description 11
- 239000011347 resin Substances 0.000 claims description 11
- 229920005989 resin Polymers 0.000 claims description 11
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims description 6
- 238000011282 treatment Methods 0.000 claims description 6
- 239000011572 manganese Substances 0.000 claims description 5
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical group [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims description 4
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 claims description 4
- 229910017052 cobalt Inorganic materials 0.000 claims description 4
- 239000010941 cobalt Substances 0.000 claims description 4
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 4
- 229910052748 manganese Inorganic materials 0.000 claims description 4
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 claims description 4
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 claims description 4
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 claims description 2
- GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 claims description 2
- ZPJDFKVKOFGAFV-UHFFFAOYSA-N 2-octadecylbutanedioic acid Chemical compound CCCCCCCCCCCCCCCCCCC(C(O)=O)CC(O)=O ZPJDFKVKOFGAFV-UHFFFAOYSA-N 0.000 claims description 2
- NCTSLPBQVXUAHR-UHFFFAOYSA-N 3,5-ditert-butylbenzoic acid Chemical compound CC(C)(C)C1=CC(C(O)=O)=CC(C(C)(C)C)=C1 NCTSLPBQVXUAHR-UHFFFAOYSA-N 0.000 claims description 2
- ZQLDNJKHLQOJGE-UHFFFAOYSA-N 4-octylbenzoic acid Chemical compound CCCCCCCCC1=CC=C(C(O)=O)C=C1 ZQLDNJKHLQOJGE-UHFFFAOYSA-N 0.000 claims description 2
- KDVYCTOWXSLNNI-UHFFFAOYSA-N 4-t-Butylbenzoic acid Chemical compound CC(C)(C)C1=CC=C(C(O)=O)C=C1 KDVYCTOWXSLNNI-UHFFFAOYSA-N 0.000 claims description 2
- AWQSAIIDOMEEOD-UHFFFAOYSA-N 5,5-Dimethyl-4-(3-oxobutyl)dihydro-2(3H)-furanone Chemical compound CC(=O)CCC1CC(=O)OC1(C)C AWQSAIIDOMEEOD-UHFFFAOYSA-N 0.000 claims description 2
- 229910052684 Cerium Inorganic materials 0.000 claims description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims description 2
- GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 claims description 2
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 claims description 2
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 2
- 239000000539 dimer Substances 0.000 claims description 2
- 239000000194 fatty acid Substances 0.000 claims description 2
- 229930195729 fatty acid Natural products 0.000 claims description 2
- 150000004665 fatty acids Chemical class 0.000 claims description 2
- 238000000622 liquid--liquid extraction Methods 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 2
- RQFLGKYCYMMRMC-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O.CCCCCCCCCCCCCCCCCC(O)=O RQFLGKYCYMMRMC-UHFFFAOYSA-N 0.000 claims description 2
- 238000000638 solvent extraction Methods 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 2
- 125000005577 anthracene group Chemical group 0.000 claims 2
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 239000003426 co-catalyst Substances 0.000 claims 1
- 229910052735 hafnium Inorganic materials 0.000 claims 1
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 claims 1
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- 150000002763 monocarboxylic acids Chemical class 0.000 claims 1
- 150000003022 phthalic acids Chemical class 0.000 claims 1
- 150000003460 sulfonic acids Chemical class 0.000 claims 1
- 238000012876 topography Methods 0.000 claims 1
- 229910052723 transition metal Inorganic materials 0.000 claims 1
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- 239000007788 liquid Substances 0.000 description 26
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 20
- 239000000203 mixture Substances 0.000 description 18
- 239000011541 reaction mixture Substances 0.000 description 17
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- 239000008346 aqueous phase Substances 0.000 description 13
- -1 aromatic carboxylic acids Chemical class 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
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- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 6
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- ZDFKSZDMHJHQHS-UHFFFAOYSA-N 2-tert-butylbenzoic acid Chemical compound CC(C)(C)C1=CC=CC=C1C(O)=O ZDFKSZDMHJHQHS-UHFFFAOYSA-N 0.000 description 2
- OCKGFTQIICXDQW-ZEQRLZLVSA-N 5-[(1r)-1-hydroxy-2-[4-[(2r)-2-hydroxy-2-(4-methyl-1-oxo-3h-2-benzofuran-5-yl)ethyl]piperazin-1-yl]ethyl]-4-methyl-3h-2-benzofuran-1-one Chemical compound C1=C2C(=O)OCC2=C(C)C([C@@H](O)CN2CCN(CC2)C[C@H](O)C2=CC=C3C(=O)OCC3=C2C)=C1 OCKGFTQIICXDQW-ZEQRLZLVSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
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- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
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- 238000005192 partition Methods 0.000 description 1
- 229950008618 perfluamine Drugs 0.000 description 1
- WTWWXOGTJWMJHI-UHFFFAOYSA-N perflubron Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)Br WTWWXOGTJWMJHI-UHFFFAOYSA-N 0.000 description 1
- 229950011087 perflunafene Drugs 0.000 description 1
- LGUZHRODIJCVOC-UHFFFAOYSA-N perfluoroheptane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F LGUZHRODIJCVOC-UHFFFAOYSA-N 0.000 description 1
- ZWBAMYVPMDSJGQ-UHFFFAOYSA-N perfluoroheptanoic acid Chemical compound OC(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F ZWBAMYVPMDSJGQ-UHFFFAOYSA-N 0.000 description 1
- UZUFPBIDKMEQEQ-UHFFFAOYSA-N perfluorononanoic acid Chemical compound OC(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F UZUFPBIDKMEQEQ-UHFFFAOYSA-N 0.000 description 1
- YVBBRRALBYAZBM-UHFFFAOYSA-N perfluorooctane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F YVBBRRALBYAZBM-UHFFFAOYSA-N 0.000 description 1
- SNGREZUHAYWORS-UHFFFAOYSA-N perfluorooctanoic acid Chemical compound OC(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F SNGREZUHAYWORS-UHFFFAOYSA-N 0.000 description 1
- RVZRBWKZFJCCIB-UHFFFAOYSA-N perfluorotributylamine Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)N(C(F)(F)C(F)(F)C(F)(F)C(F)(F)F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F RVZRBWKZFJCCIB-UHFFFAOYSA-N 0.000 description 1
- JAJLKEVKNDUJBG-UHFFFAOYSA-N perfluorotripropylamine Chemical compound FC(F)(F)C(F)(F)C(F)(F)N(C(F)(F)C(F)(F)C(F)(F)F)C(F)(F)C(F)(F)C(F)(F)F JAJLKEVKNDUJBG-UHFFFAOYSA-N 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003021 phthalic acid derivatives Chemical class 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- GETTZEONDQJALK-UHFFFAOYSA-N trifluorotoluene Substances FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/31—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation of cyclic compounds with ring-splitting
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/487—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C55/00—Saturated compounds having more than one carboxyl group bound to acyclic carbon atoms
- C07C55/02—Dicarboxylic acids
- C07C55/12—Glutaric acid
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0213576A FR2846651B1 (fr) | 2002-10-30 | 2002-10-30 | Procede de fabrication d'acides carboxyliques |
| PCT/FR2003/003198 WO2004041765A1 (fr) | 2002-10-30 | 2003-10-28 | Procede de fabrication d'acides carboxyliques |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA79640C2 true UA79640C2 (en) | 2007-07-10 |
Family
ID=32104304
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UAA200504096A UA79640C2 (en) | 2002-10-30 | 2003-10-28 | A method for making adipinic acid |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US7253312B2 (ja) |
| EP (1) | EP1562886A1 (ja) |
| JP (1) | JP2006504781A (ja) |
| KR (1) | KR100683462B1 (ja) |
| CN (1) | CN100404490C (ja) |
| AU (1) | AU2003285476A1 (ja) |
| BR (1) | BR0315060B1 (ja) |
| FR (1) | FR2846651B1 (ja) |
| RU (1) | RU2296743C2 (ja) |
| UA (1) | UA79640C2 (ja) |
| WO (1) | WO2004041765A1 (ja) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2611831C (en) | 2005-06-17 | 2014-09-16 | Vital Health Sciences Pty Ltd. | A carrier comprising one or more di and/or mono-(electron transfer agent) phosphate derivatives or complexes thereof |
| SG176970A1 (en) | 2009-07-02 | 2012-02-28 | Verdezyne Inc | Biological methods for preparing adipic acid |
| KR20120107963A (ko) * | 2009-12-23 | 2012-10-04 | 포스파제닉스 리미티드 | 담체 조성물 |
| US10071030B2 (en) | 2010-02-05 | 2018-09-11 | Phosphagenics Limited | Carrier comprising non-neutralised tocopheryl phosphate |
| ES2829386T3 (es) | 2010-03-30 | 2021-05-31 | Phosphagenics Ltd | Parche de administración transdérmica |
| EP2685992A4 (en) | 2011-03-15 | 2014-09-10 | Phosphagenics Ltd | AMINO-QUINOLINES AS KINASE INHIBITORS |
| US8728798B2 (en) | 2011-05-03 | 2014-05-20 | Verdezyne, Inc. | Biological methods for preparing adipic acid |
| AU2016367708B2 (en) | 2015-12-09 | 2022-07-14 | Phosphagenics Limited | Pharmaceutical formulation |
| MX2019006845A (es) | 2016-12-21 | 2019-10-15 | Avecho Biotechnology Ltd | Proceso. |
| CN108855087B (zh) * | 2017-05-12 | 2021-03-30 | 中国石油天然气股份有限公司 | 用于制备己二酸的催化剂及其制备方法、己二酸的制备方法 |
| CN113924282B (zh) * | 2019-06-12 | 2023-09-12 | 诺力昂化学品国际有限公司 | 用于从含水侧流中分离羧酸的方法 |
| ES2963382T3 (es) | 2019-06-12 | 2024-03-26 | Nouryon Chemicals Int Bv | Proceso para la producción de peróxidos de diacilo |
| WO2020249688A1 (en) | 2019-06-12 | 2020-12-17 | Nouryon Chemicals International B.V. | Process for the production of diacyl peroxides |
| CN115417758A (zh) * | 2022-09-22 | 2022-12-02 | 山东大学 | 一种高纯度结晶状全氟辛酸的制备方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9113343D0 (en) | 1991-06-20 | 1991-08-07 | Shell Int Research | Catalytic oxidation of hydrocarbons |
| DE4427474A1 (de) * | 1994-08-03 | 1996-02-08 | Bayer Ag | Verfahren zur Herstellung von Adipinsäure |
| FR2757155B1 (fr) * | 1996-12-12 | 1999-11-12 | Rhone Poulenc Fibres | Procede de traitement de melanges reactionnels issus de l'oxydation du cyclohexane |
| FR2761984B1 (fr) | 1997-04-10 | 1999-05-21 | Rhone Poulenc Fibres | Procede d'oxydation d'hydrocarbures, d'alcools et/ou de cetones |
| ES2179705B2 (es) | 1997-07-08 | 2003-06-16 | Mannesmann Sachs Ag | Amortiguador de vibraciones regulable para vehiculos de motor. |
| FR2775685B1 (fr) * | 1998-03-05 | 2000-12-29 | Rhone Poulenc Fibres | Procede de separation et de purification de l'acide adipique |
| US6433220B1 (en) * | 1998-07-02 | 2002-08-13 | Rpc Inc. | Methods of extracting catalyst from a reaction mixture in the oxidation of cyclohexane to adipic acid |
| FR2791667B1 (fr) | 1999-03-30 | 2002-05-24 | Rhone Poulenc Fibres | Procede d'oxydation d'hydrocarbures, d'alcools et/ou de cetones |
| FR2806079B1 (fr) * | 2000-03-08 | 2003-03-14 | Rhodia Polyamide Intermediates | Procede d'oxydation d'hydrocarbures en acides |
-
2002
- 2002-10-30 FR FR0213576A patent/FR2846651B1/fr not_active Expired - Fee Related
-
2003
- 2003-10-08 US US10/533,212 patent/US7253312B2/en not_active Expired - Fee Related
- 2003-10-28 CN CNB2003801039460A patent/CN100404490C/zh not_active Expired - Fee Related
- 2003-10-28 JP JP2004549261A patent/JP2006504781A/ja active Pending
- 2003-10-28 UA UAA200504096A patent/UA79640C2/uk unknown
- 2003-10-28 BR BRPI0315060-7A patent/BR0315060B1/pt not_active IP Right Cessation
- 2003-10-28 EP EP03778477A patent/EP1562886A1/fr not_active Withdrawn
- 2003-10-28 KR KR1020057007651A patent/KR100683462B1/ko not_active IP Right Cessation
- 2003-10-28 RU RU2005116249/04A patent/RU2296743C2/ru not_active IP Right Cessation
- 2003-10-28 AU AU2003285476A patent/AU2003285476A1/en not_active Abandoned
- 2003-10-28 WO PCT/FR2003/003198 patent/WO2004041765A1/fr active Application Filing
Also Published As
| Publication number | Publication date |
|---|---|
| RU2296743C2 (ru) | 2007-04-10 |
| CN100404490C (zh) | 2008-07-23 |
| CN1714068A (zh) | 2005-12-28 |
| BR0315060A (pt) | 2005-08-16 |
| KR20050065651A (ko) | 2005-06-29 |
| RU2005116249A (ru) | 2006-01-27 |
| EP1562886A1 (fr) | 2005-08-17 |
| AU2003285476A1 (en) | 2004-06-07 |
| US7253312B2 (en) | 2007-08-07 |
| WO2004041765A1 (fr) | 2004-05-21 |
| BR0315060B1 (pt) | 2013-04-02 |
| FR2846651A1 (fr) | 2004-05-07 |
| KR100683462B1 (ko) | 2007-02-22 |
| US20060106251A1 (en) | 2006-05-18 |
| FR2846651B1 (fr) | 2006-06-16 |
| JP2006504781A (ja) | 2006-02-09 |
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