CA1062279A - Secondary oxidation of fluid effluent from primary oxidation of meta-or para-xylene - Google Patents
Secondary oxidation of fluid effluent from primary oxidation of meta-or para-xyleneInfo
- Publication number
- CA1062279A CA1062279A CA263,924A CA263924A CA1062279A CA 1062279 A CA1062279 A CA 1062279A CA 263924 A CA263924 A CA 263924A CA 1062279 A CA1062279 A CA 1062279A
- Authority
- CA
- Canada
- Prior art keywords
- oxidation
- acetic acid
- xylene
- primary
- iso
- 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
- 238000007254 oxidation reaction Methods 0.000 title claims abstract description 244
- 230000003647 oxidation Effects 0.000 title claims abstract description 240
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 title claims abstract description 54
- 239000012530 fluid Substances 0.000 title claims abstract description 43
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical compound CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 title claims abstract description 28
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 329
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims abstract description 144
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims abstract description 73
- 239000012452 mother liquor Substances 0.000 claims abstract description 36
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 28
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 28
- 239000001301 oxygen Substances 0.000 claims abstract description 28
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 26
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 24
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 24
- 238000006555 catalytic reaction Methods 0.000 claims abstract description 16
- 239000002243 precursor Substances 0.000 claims abstract description 16
- 239000007787 solid Substances 0.000 claims abstract description 11
- 239000000725 suspension Substances 0.000 claims abstract description 7
- 238000002425 crystallisation Methods 0.000 claims description 54
- 230000008025 crystallization Effects 0.000 claims description 53
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 33
- 229910017052 cobalt Inorganic materials 0.000 claims description 31
- 239000010941 cobalt Substances 0.000 claims description 31
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 23
- 239000011572 manganese Substances 0.000 claims description 22
- 229910052748 manganese Inorganic materials 0.000 claims description 20
- 239000008096 xylene Substances 0.000 claims description 19
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 18
- 230000008569 process Effects 0.000 claims description 18
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 238000001816 cooling Methods 0.000 claims description 13
- 230000001965 increasing effect Effects 0.000 claims description 6
- 230000003247 decreasing effect Effects 0.000 claims description 5
- 238000011084 recovery Methods 0.000 claims description 4
- 238000010924 continuous production Methods 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 abstract description 27
- 229910052751 metal Inorganic materials 0.000 abstract description 27
- 239000002184 metal Substances 0.000 abstract description 27
- 239000007791 liquid phase Substances 0.000 abstract description 17
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 abstract description 14
- 239000002253 acid Substances 0.000 abstract description 11
- 239000007788 liquid Substances 0.000 abstract description 9
- 125000003118 aryl group Chemical group 0.000 abstract description 5
- 230000003197 catalytic effect Effects 0.000 abstract description 5
- 239000000306 component Substances 0.000 abstract 4
- 239000000047 product Substances 0.000 description 55
- GOUHYARYYWKXHS-UHFFFAOYSA-N 4-formylbenzoic acid Chemical compound OC(=O)C1=CC=C(C=O)C=C1 GOUHYARYYWKXHS-UHFFFAOYSA-N 0.000 description 36
- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 description 30
- 230000004044 response Effects 0.000 description 23
- 239000000243 solution Substances 0.000 description 17
- 239000002002 slurry Substances 0.000 description 15
- 239000000203 mixture Substances 0.000 description 14
- 230000007423 decrease Effects 0.000 description 13
- 235000002908 manganese Nutrition 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 11
- 230000000694 effects Effects 0.000 description 11
- GPSDUZXPYCFOSQ-UHFFFAOYSA-N m-toluic acid Chemical compound CC1=CC=CC(C(O)=O)=C1 GPSDUZXPYCFOSQ-UHFFFAOYSA-N 0.000 description 10
- 238000012546 transfer Methods 0.000 description 10
- 238000010992 reflux Methods 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 239000007789 gas Substances 0.000 description 8
- 238000011068 loading method Methods 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 6
- 238000013461 design Methods 0.000 description 6
- 230000029087 digestion Effects 0.000 description 6
- 239000002360 explosive Substances 0.000 description 6
- UHDNUPHSDMOGCR-UHFFFAOYSA-N 3-Formylbenzoic acid Chemical compound OC(=O)C1=CC=CC(C=O)=C1 UHDNUPHSDMOGCR-UHFFFAOYSA-N 0.000 description 5
- 150000001649 bromium compounds Chemical class 0.000 description 5
- PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 230000002844 continuous effect Effects 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000006324 decarbonylation Effects 0.000 description 3
- 238000006606 decarbonylation reaction Methods 0.000 description 3
- 238000006114 decarboxylation reaction Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 238000005070 sampling Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000004148 unit process Methods 0.000 description 3
- RVHSTXJKKZWWDQ-UHFFFAOYSA-N 1,1,1,2-tetrabromoethane Chemical compound BrCC(Br)(Br)Br RVHSTXJKKZWWDQ-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000001242 acetic acid derivatives Chemical class 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 229940006460 bromide ion Drugs 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 230000001609 comparable effect Effects 0.000 description 2
- 238000004590 computer program Methods 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000007405 data analysis Methods 0.000 description 2
- 238000013401 experimental design Methods 0.000 description 2
- 235000003642 hunger Nutrition 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 238000009434 installation Methods 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 238000004540 process dynamic Methods 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 239000012086 standard solution Substances 0.000 description 2
- 230000037351 starvation Effects 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- AKYHKWQPZHDOBW-UHFFFAOYSA-N (5-ethenyl-1-azabicyclo[2.2.2]octan-7-yl)-(6-methoxyquinolin-4-yl)methanol Chemical compound OS(O)(=O)=O.C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 AKYHKWQPZHDOBW-UHFFFAOYSA-N 0.000 description 1
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- BOKGTLAJQHTOKE-UHFFFAOYSA-N 1,5-dihydroxynaphthalene Chemical group C1=CC=C2C(O)=CC=CC2=C1O BOKGTLAJQHTOKE-UHFFFAOYSA-N 0.000 description 1
- DYNFCHNNOHNJFG-UHFFFAOYSA-N 2-formylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C=O DYNFCHNNOHNJFG-UHFFFAOYSA-N 0.000 description 1
- CLDYHEHXORSJFQ-UHFFFAOYSA-N 3-[carboxy(phenyl)methoxy]carbonylphthalic acid Chemical compound C(=O)(O)C=1C(=C(C(=O)OC(C2=CC=CC=C2)C(=O)O)C=CC1)C(=O)O CLDYHEHXORSJFQ-UHFFFAOYSA-N 0.000 description 1
- DZFAKQZRZPHYLG-VOTSOKGWSA-N 4-[(e)-2-phenylethenyl]cyclohexa-2,4-diene-1,1-dicarboxylic acid Chemical compound C1=CC(C(=O)O)(C(O)=O)CC=C1\C=C\C1=CC=CC=C1 DZFAKQZRZPHYLG-VOTSOKGWSA-N 0.000 description 1
- QQPQYWGNVMIGAF-UHFFFAOYSA-N 9,10-dioxoanthracene-1,2-dicarboxylic acid Chemical compound C1=CC=C2C(=O)C3=C(C(O)=O)C(C(=O)O)=CC=C3C(=O)C2=C1 QQPQYWGNVMIGAF-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical class [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 239000001576 FEMA 2977 Substances 0.000 description 1
- 244000303040 Glycyrrhiza glabra Species 0.000 description 1
- 244000241838 Lycium barbarum Species 0.000 description 1
- -1 Methyl-substituted phthalic acids Chemical class 0.000 description 1
- XVJAJJBYRFUTTM-UHFFFAOYSA-N O.O.O.O.C(C)(=O)O.C(O)(O)=O Chemical compound O.O.O.O.C(C)(=O)O.C(O)(O)=O XVJAJJBYRFUTTM-UHFFFAOYSA-N 0.000 description 1
- 230000002730 additional effect Effects 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical compound C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- 150000003842 bromide salts Chemical class 0.000 description 1
- 150000004768 bromobenzenes Chemical class 0.000 description 1
- 229910002090 carbon oxide Inorganic materials 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 1
- PJANXHGTPQOBST-QXMHVHEDSA-N cis-stilbene Chemical compound C=1C=CC=CC=1/C=C\C1=CC=CC=C1 PJANXHGTPQOBST-QXMHVHEDSA-N 0.000 description 1
- 229940000425 combination drug Drugs 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000012809 cooling fluid Substances 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 230000001351 cycling effect Effects 0.000 description 1
- SIEILFNCEFEENQ-UHFFFAOYSA-N dibromoacetic acid Chemical compound OC(=O)C(Br)Br SIEILFNCEFEENQ-UHFFFAOYSA-N 0.000 description 1
- 230000001079 digestive effect Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- ZDGGJQMSELMHLK-UHFFFAOYSA-N m-Trifluoromethylhippuric acid Chemical compound OC(=O)CNC(=O)C1=CC=CC(C(F)(F)F)=C1 ZDGGJQMSELMHLK-UHFFFAOYSA-N 0.000 description 1
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 229940036310 program Drugs 0.000 description 1
- 229960003110 quinine sulfate Drugs 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007619 statistical method Methods 0.000 description 1
- 150000001629 stilbenes Chemical class 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 238000012731 temporal analysis Methods 0.000 description 1
- 150000004685 tetrahydrates Chemical class 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000000700 time series analysis Methods 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 150000003738 xylenes Chemical class 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
- C07C51/21—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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US62567575A | 1975-10-24 | 1975-10-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1062279A true CA1062279A (en) | 1979-09-11 |
Family
ID=24507104
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA263,924A Expired CA1062279A (en) | 1975-10-24 | 1976-10-22 | Secondary oxidation of fluid effluent from primary oxidation of meta-or para-xylene |
Country Status (11)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5183933A (en) * | 1991-10-15 | 1993-02-02 | Amoco Corporation | Process for preparing 2,6-naphthalene-dicarboxylic acid |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2714985C2 (de) * | 1977-04-04 | 1982-05-06 | Chemische Werke Hüls AG, 4370 Marl | Verfahren zur Reinigung von Terephthalsäure |
| JPS5470235A (en) * | 1977-11-14 | 1979-06-05 | Mitsubishi Chem Ind Ltd | Preparation of terephthalic acid |
| US4334086A (en) * | 1981-03-16 | 1982-06-08 | Labofina S.A. | Production of terephthalic acid |
| DE3128147C2 (de) * | 1981-07-16 | 1986-03-06 | Dynamit Nobel Ag, 5210 Troisdorf | Verfahren zur Gewinnung von aromatischen Monocarbonsäuren |
| JP2893860B2 (ja) * | 1990-05-17 | 1999-05-24 | 三菱瓦斯化学株式会社 | 高純度イソフタル酸の製造法 |
| US5132450A (en) * | 1990-06-25 | 1992-07-21 | Mitsubishi Gas Chemical Company, Inc. | Process for producing high purity isophthalic acid |
| US7589231B2 (en) | 2004-09-02 | 2009-09-15 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7563926B2 (en) | 2004-09-02 | 2009-07-21 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7741515B2 (en) | 2004-09-02 | 2010-06-22 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7495125B2 (en) | 2004-09-02 | 2009-02-24 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7399882B2 (en) | 2004-09-02 | 2008-07-15 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7361784B2 (en) | 2004-09-02 | 2008-04-22 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7572932B2 (en) * | 2004-09-02 | 2009-08-11 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7371894B2 (en) | 2004-09-02 | 2008-05-13 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7692036B2 (en) * | 2004-11-29 | 2010-04-06 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7683210B2 (en) | 2004-09-02 | 2010-03-23 | 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 |
| US7504535B2 (en) | 2004-09-02 | 2009-03-17 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7586000B2 (en) | 2004-09-02 | 2009-09-08 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7608733B2 (en) | 2004-09-02 | 2009-10-27 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7507857B2 (en) | 2004-09-02 | 2009-03-24 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7692037B2 (en) | 2004-09-02 | 2010-04-06 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7381836B2 (en) | 2004-09-02 | 2008-06-03 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7482482B2 (en) | 2004-09-02 | 2009-01-27 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7608732B2 (en) | 2005-03-08 | 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 |
| US7568361B2 (en) | 2004-09-02 | 2009-08-04 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7884232B2 (en) | 2005-06-16 | 2011-02-08 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7358389B2 (en) | 2006-01-04 | 2008-04-15 | Eastman Chemical Company | Oxidation system employing internal structure for enhanced hydrodynamics |
| US7355068B2 (en) | 2006-01-04 | 2008-04-08 | Eastman Chemical Company | Oxidation system with internal secondary reactor |
| CN110944972A (zh) * | 2017-06-29 | 2020-03-31 | Bp北美公司 | 制造芳族羧酸的方法 |
| CN112110813A (zh) * | 2020-09-18 | 2020-12-22 | 中国石化扬子石油化工有限公司 | 一种促进偏苯三甲酸结晶的方法 |
-
1976
- 1976-10-20 BE BE171665A patent/BE847474A/xx not_active IP Right Cessation
- 1976-10-21 DE DE19762647698 patent/DE2647698A1/de active Granted
- 1976-10-21 LU LU76048A patent/LU76048A1/xx unknown
- 1976-10-22 DK DK477776A patent/DK159259C/da not_active IP Right Cessation
- 1976-10-22 CA CA263,924A patent/CA1062279A/en not_active Expired
- 1976-10-22 IT IT5186376A patent/IT1073924B/it active
- 1976-10-22 GB GB4400676A patent/GB1555246A/en not_active Expired
- 1976-10-22 NL NL7611720A patent/NL188637C/xx not_active IP Right Cessation
- 1976-10-23 JP JP12681576A patent/JPS6048497B2/ja not_active Expired
- 1976-10-25 YU YU260576A patent/YU42274B/xx unknown
- 1976-10-25 FR FR7632100A patent/FR2328688A1/fr active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5183933A (en) * | 1991-10-15 | 1993-02-02 | Amoco Corporation | Process for preparing 2,6-naphthalene-dicarboxylic acid |
Also Published As
| Publication number | Publication date |
|---|---|
| DK159259C (da) | 1991-04-08 |
| NL188637C (nl) | 1992-08-17 |
| DK477776A (da) | 1977-04-25 |
| YU42274B (en) | 1988-08-31 |
| FR2328688B1 (enrdf_load_stackoverflow) | 1978-12-15 |
| BE847474A (fr) | 1977-04-20 |
| JPS6048497B2 (ja) | 1985-10-28 |
| IT1073924B (it) | 1985-04-17 |
| DE2647698C2 (enrdf_load_stackoverflow) | 1989-06-15 |
| FR2328688A1 (fr) | 1977-05-20 |
| YU260576A (en) | 1982-05-31 |
| GB1555246A (en) | 1979-11-07 |
| DE2647698A1 (de) | 1977-04-28 |
| DK159259B (da) | 1990-09-24 |
| JPS5285136A (en) | 1977-07-15 |
| LU76048A1 (enrdf_load_stackoverflow) | 1977-05-31 |
| NL7611720A (nl) | 1977-04-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1062279A (en) | Secondary oxidation of fluid effluent from primary oxidation of meta-or para-xylene | |
| EP0135341B1 (en) | Process for preparing terephthalic acid from para-xylene | |
| JP2504461B2 (ja) | 高品質テレフタル酸の製法 | |
| EP0021747B1 (en) | Process for the preparation of terephthalic acid | |
| US4158738A (en) | Process for the production of fiber-grade terephthalic acid | |
| US4772748A (en) | Process for producing highly pure terephthalic acid | |
| EP0465100B1 (en) | Process for producing high purity isophthalic acid | |
| US4286101A (en) | Process for preparing terephthalic acid | |
| AU732522B2 (en) | Method to produce aromatic carboxylic acids | |
| US5338882A (en) | Process for the production of DMT-intermediate product of specific purity and pure terephthalic acid | |
| IE44182B1 (en) | Secondary oxidation of fluid effluent from primary oxidation of meta- or para-xylene | |
| EP1003699B1 (en) | Purification of difluoromethane by extractive distillation | |
| GB2047704A (en) | Preparation of terephthalalic acid by hydrolysis of dimethyl terephthalate | |
| EP1062196B1 (en) | Improved process for producing pure carboxylic acids | |
| US3171856A (en) | Acid purification process | |
| US4845274A (en) | Oxidation of polyalkylaromatics | |
| US20080293964A1 (en) | Process for Preparing High Purity Terephthalic Acid | |
| EP1501778B1 (en) | Process for the production of carboxylic acids | |
| US4754062A (en) | Iron-enhanced selectivity of heavy metal-bromine catalysis in the oxidation of polyalkylaromatics | |
| US20060094901A1 (en) | Process for the production of carboxylic acids | |
| JP2504545B2 (ja) | テレフタル酸の製造法 | |
| JPH0357887B2 (enrdf_load_stackoverflow) | ||
| JPH1192416A (ja) | トリメリット酸の製造法 | |
| JPH06345685A (ja) | １，４−ナフタレンジカルボン酸の製造方法 | |
| GB1603393A (en) | Process for the production of a high purity terephthalic acid |