CN1068577C - 制备芳族羧酸的工业方法 - Google Patents
制备芳族羧酸的工业方法 Download PDFInfo
- Publication number
- CN1068577C CN1068577C CN96122753A CN96122753A CN1068577C CN 1068577 C CN1068577 C CN 1068577C CN 96122753 A CN96122753 A CN 96122753A CN 96122753 A CN96122753 A CN 96122753A CN 1068577 C CN1068577 C CN 1068577C
- Authority
- CN
- China
- Prior art keywords
- carboxylic acid
- reactor
- air
- pipe
- solvent
- 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 - Lifetime
Links
- -1 aromatic carboxylic acids Chemical class 0.000 title abstract description 5
- 238000004519 manufacturing process Methods 0.000 title description 6
- 238000000034 method Methods 0.000 claims abstract description 20
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 18
- 230000003647 oxidation Effects 0.000 claims abstract description 17
- 239000003054 catalyst Substances 0.000 claims abstract description 11
- 239000007791 liquid phase Substances 0.000 claims abstract description 9
- 230000008569 process Effects 0.000 claims abstract description 7
- 239000012153 distilled water Substances 0.000 claims abstract description 4
- 238000004064 recycling Methods 0.000 claims abstract description 4
- 239000002904 solvent Substances 0.000 claims description 14
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 12
- 239000000243 solution Substances 0.000 claims description 11
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 9
- 230000002000 scavenging effect Effects 0.000 claims description 8
- 239000007864 aqueous solution Substances 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 238000004140 cleaning Methods 0.000 claims description 5
- 239000012535 impurity Substances 0.000 claims description 5
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 239000010936 titanium Substances 0.000 claims description 4
- 229910052719 titanium Inorganic materials 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 235000014347 soups Nutrition 0.000 claims 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
- SVMCDCBHSKARBQ-UHFFFAOYSA-N acetic acid;cobalt Chemical compound [Co].CC(O)=O SVMCDCBHSKARBQ-UHFFFAOYSA-N 0.000 claims 1
- 229910001882 dioxygen Inorganic materials 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 abstract description 3
- 238000001704 evaporation Methods 0.000 abstract description 2
- 230000008020 evaporation Effects 0.000 abstract description 2
- 238000002386 leaching Methods 0.000 abstract description 2
- 238000010926 purge Methods 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 20
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 13
- 239000001301 oxygen Substances 0.000 description 13
- 229910052760 oxygen Inorganic materials 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 11
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 10
- 230000001590 oxidative effect Effects 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 5
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- 238000013461 design Methods 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000010924 continuous production Methods 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910052748 manganese Inorganic materials 0.000 description 3
- 239000011572 manganese Substances 0.000 description 3
- 239000012452 mother liquor Substances 0.000 description 3
- 230000004044 response Effects 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- QMKYBPDZANOJGF-UHFFFAOYSA-N benzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 230000005012 migration Effects 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000002910 solid waste Substances 0.000 description 2
- 239000006200 vaporizer Substances 0.000 description 2
- MWYDUCLWRJMRLP-UHFFFAOYSA-N 1,1,1,2-tetrabromoethane hydrobromide Chemical compound Br.BrCC(Br)(Br)Br MWYDUCLWRJMRLP-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 244000287680 Garcinia dulcis Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241001074085 Scophthalmus aquosus Species 0.000 description 1
- 159000000021 acetate salts Chemical class 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 description 1
- 230000002301 combined effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000010413 mother solution Substances 0.000 description 1
- RXOHFPCZGPKIRD-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 RXOHFPCZGPKIRD-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Images
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
- C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
- C07C51/255—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of compounds containing six-membered aromatic rings without ring-splitting
- C07C51/265—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of compounds containing six-membered aromatic rings without ring-splitting having alkyl side chains which are oxidised to carboxyl groups
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J4/00—Feed or outlet devices; Feed or outlet control devices
- B01J4/04—Feed or outlet devices; Feed or outlet control devices using osmotic pressure using membranes, porous plates
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (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 |
|---|---|---|---|
| ES09501832A ES2104512B1 (es) | 1995-09-21 | 1995-09-21 | Procedimiento industrial para la fabricacion de acidos carboxilicos aromaticos. |
| ES9501832 | 1995-09-21 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1153766A CN1153766A (zh) | 1997-07-09 |
| CN1068577C true CN1068577C (zh) | 2001-07-18 |
Family
ID=8291629
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN96122753A Expired - Lifetime CN1068577C (zh) | 1995-09-21 | 1996-09-21 | 制备芳族羧酸的工业方法 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US5739384A (enExample) |
| EP (1) | EP0764626B1 (enExample) |
| CN (1) | CN1068577C (enExample) |
| CA (1) | CA2186058C (enExample) |
| DE (1) | DE69609913T2 (enExample) |
| ES (1) | ES2104512B1 (enExample) |
| IN (1) | IN189087B (enExample) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6657067B2 (en) | 2002-03-22 | 2003-12-02 | General Electric Company | Method for the manufacture of chlorophthalic anhydride |
| US6657068B2 (en) | 2002-03-22 | 2003-12-02 | General Electric Company | Liquid phase oxidation of halogenated ortho-xylenes |
| US6649773B2 (en) | 2002-03-22 | 2003-11-18 | General Electric Company | Method for the manufacture of halophthalic acids and anhydrides |
| US20060004223A1 (en) * | 2004-06-30 | 2006-01-05 | General Electric Company | Method of making halophthalic acids and halophthalic anhydrides |
| US7541489B2 (en) * | 2004-06-30 | 2009-06-02 | Sabic Innovative Plastics Ip B.V. | Method of making halophthalic acids and halophthalic anhydrides |
| US7371894B2 (en) * | 2004-09-02 | 2008-05-13 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7572932B2 (en) * | 2004-09-02 | 2009-08-11 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7692036B2 (en) | 2004-11-29 | 2010-04-06 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7504535B2 (en) * | 2004-09-02 | 2009-03-17 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7361784B2 (en) * | 2004-09-02 | 2008-04-22 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7608733B2 (en) * | 2004-09-02 | 2009-10-27 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7572936B2 (en) | 2004-09-02 | 2009-08-11 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7582793B2 (en) * | 2004-09-02 | 2009-09-01 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7390921B2 (en) * | 2004-09-02 | 2008-06-24 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7586000B2 (en) * | 2004-09-02 | 2009-09-08 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7910769B2 (en) * | 2004-09-02 | 2011-03-22 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7381836B2 (en) * | 2004-09-02 | 2008-06-03 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7683210B2 (en) * | 2004-09-02 | 2010-03-23 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7563926B2 (en) * | 2004-09-02 | 2009-07-21 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7568361B2 (en) * | 2004-09-02 | 2009-08-04 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7495125B2 (en) * | 2004-09-02 | 2009-02-24 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7507857B2 (en) * | 2004-09-02 | 2009-03-24 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7482482B2 (en) * | 2004-09-02 | 2009-01-27 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7741515B2 (en) | 2004-09-02 | 2010-06-22 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7589231B2 (en) * | 2004-09-02 | 2009-09-15 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7692037B2 (en) * | 2004-09-02 | 2010-04-06 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7399882B2 (en) * | 2004-09-02 | 2008-07-15 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7608732B2 (en) * | 2005-03-08 | 2009-10-27 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7884232B2 (en) * | 2005-06-16 | 2011-02-08 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7355068B2 (en) * | 2006-01-04 | 2008-04-08 | Eastman Chemical Company | Oxidation system with internal secondary reactor |
| US7358389B2 (en) * | 2006-01-04 | 2008-04-15 | Eastman Chemical Company | Oxidation system employing internal structure for enhanced hydrodynamics |
| EP2276720B1 (en) | 2008-03-18 | 2015-07-29 | Gtc Technology, Lp | Improved systems and processes for the production of isophthalic acid and terephthalic acid |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB970492A (en) * | 1960-10-18 | 1964-09-23 | Standard Oil Co | Production of aromatic carboxylic acids |
| US4777287A (en) * | 1984-10-29 | 1988-10-11 | Amoco Corporation | Recycle of vaporized solvent in liquid phase oxidation of an alkyl aromatic |
Family Cites Families (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2245528A (en) * | 1938-10-18 | 1941-06-10 | Du Pont | Catalytic oxidation of alkyl substituted aromatic compounds |
| US2445528A (en) | 1946-03-16 | 1948-07-20 | Jr Edward S Keogh | Razor |
| US2833816A (en) * | 1954-05-03 | 1958-05-06 | Mid Century Corp | Preparation of aromatic polycarboxylic acids |
| GB832995A (en) * | 1956-11-05 | 1960-04-21 | Ici Ltd | Improvements in and relating to a process for the oxidation of organic compounds |
| US2883816A (en) | 1957-05-24 | 1959-04-28 | Kroll Eberhard | Apparatus for automatically placing articles in layers in containers particularly fish in barrels |
| US2997500A (en) * | 1958-01-13 | 1961-08-22 | Sun Oil Co | Separating isophthalic and terephthalic acids |
| US3069462A (en) * | 1958-05-05 | 1962-12-18 | Mid Century Corp | Oxidation of aromatic compounds |
| GB970491A (en) * | 1960-10-18 | 1964-09-23 | Standard Oil Co | Production of aromatic carboxylic acids |
| DE1251735B (de) * | 1965-07-28 | 1967-10-12 | Chemische Werke Witten Gesellschaft mit beschrankter Haftung Witten/ Ruhr | Veifahren zur Gewinnung von reiner Terephthalsäure |
| DE1299627B (de) * | 1966-08-31 | 1969-07-24 | Dynamit Nobel Ag | Verfahren zur Herstellung von reinster Terepthalsaeure |
| US3549695A (en) * | 1966-09-01 | 1970-12-22 | Mobil Oil Corp | Method for downflow leaching |
| US3839436A (en) * | 1969-05-26 | 1974-10-01 | Standard Oil Co | Integration of para-or meta-xylene oxidation to terephthalic acid or isophthalic acid and its purification by hydrogen treatment of aqueous solution |
| BE757742A (fr) * | 1969-10-20 | 1971-04-20 | Montedison Spa | Procede de preparation de composes aromatiques |
| DD96700A5 (enExample) * | 1971-07-02 | 1973-04-05 | ||
| US3920735A (en) * | 1973-05-21 | 1975-11-18 | Standard Oil Co | Zirconium enhanced activity of transition metal-bromine catalysis of di- and trimethyl benzene oxidation in liquid phase |
| NL170133C (nl) * | 1976-02-24 | 1982-10-01 | Matsuyama Petrochemicals Inc | Werkwijze voor de bereiding van een aromatisch dicarbonzuur. |
| AU510097B2 (en) * | 1976-07-26 | 1980-06-05 | Standard Oil Company | reparing iso or terphthalic acid |
| NL7906575A (nl) * | 1979-09-01 | 1981-03-03 | Stamicarbon | Werkwijze ter bereiding van aromatische carbonzuren. |
| US4391985A (en) * | 1981-11-16 | 1983-07-05 | Eastman Kodak Company | Process for the separation of isophthalic acid from terephthalic acid |
| US4835307A (en) * | 1984-12-13 | 1989-05-30 | Amoco Corporation | Method and apparatus for controlling the manufacture of terephthalic acid to control the level and variability of the contaminant content and the optical density |
| US4792621A (en) * | 1986-07-28 | 1988-12-20 | Amoco Corporation | Method for continuous production of aromatic carboxylic acid |
| US5102630A (en) * | 1988-03-17 | 1992-04-07 | Amoco Corporation | Apparatus for increasing yield and product quality while reducing power costs in oxidation of an aromatic alkyl to an aromatic carboxylic acid |
| US4855492A (en) * | 1988-05-27 | 1989-08-08 | Amoco Corporation | Process for production of aromatic polycarboxylic acids |
| US4873386A (en) * | 1988-06-28 | 1989-10-10 | Amoco Corporation | Selective production of 2,6-diethylnaphthalene |
| JPH0293597A (ja) * | 1988-09-30 | 1990-04-04 | Nippon I B M Kk | 音声認識装置 |
| KR940010108B1 (ko) * | 1991-08-29 | 1994-10-21 | 한국과학기술원 | 반경방향 분산기를 이용한 기포탑 반응기 |
| US5453538A (en) * | 1994-02-14 | 1995-09-26 | Amoco Corporation | Process for the manufacture of aromatic dicarboxylic acids utilizing cerium to facilitate a low bromine to metals catalyst ratio |
-
1995
- 1995-09-21 ES ES09501832A patent/ES2104512B1/es not_active Expired - Fee Related
-
1996
- 1996-09-20 EP EP96202629A patent/EP0764626B1/en not_active Expired - Lifetime
- 1996-09-20 CA CA002186058A patent/CA2186058C/en not_active Expired - Lifetime
- 1996-09-20 US US08/717,016 patent/US5739384A/en not_active Expired - Lifetime
- 1996-09-20 DE DE69609913T patent/DE69609913T2/de not_active Expired - Lifetime
- 1996-09-21 CN CN96122753A patent/CN1068577C/zh not_active Expired - Lifetime
- 1996-09-23 IN IN1685CA1996 patent/IN189087B/en unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB970492A (en) * | 1960-10-18 | 1964-09-23 | Standard Oil Co | Production of aromatic carboxylic acids |
| US4777287A (en) * | 1984-10-29 | 1988-10-11 | Amoco Corporation | Recycle of vaporized solvent in liquid phase oxidation of an alkyl aromatic |
Also Published As
| Publication number | Publication date |
|---|---|
| ES2104512A1 (es) | 1997-10-01 |
| CN1153766A (zh) | 1997-07-09 |
| EP0764626B1 (en) | 2000-08-23 |
| ES2104512B1 (es) | 1998-07-01 |
| CA2186058A1 (en) | 1997-03-22 |
| US5739384A (en) | 1998-04-14 |
| CA2186058C (en) | 2001-06-12 |
| IN189087B (enExample) | 2002-12-14 |
| DE69609913D1 (de) | 2000-09-28 |
| DE69609913T2 (de) | 2001-02-22 |
| EP0764626A1 (en) | 1997-03-26 |
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