CA1105943A - Process for the preparation of terephthalic acid - Google Patents
Process for the preparation of terephthalic acidInfo
- Publication number
- CA1105943A CA1105943A CA289,160A CA289160A CA1105943A CA 1105943 A CA1105943 A CA 1105943A CA 289160 A CA289160 A CA 289160A CA 1105943 A CA1105943 A CA 1105943A
- Authority
- CA
- Canada
- Prior art keywords
- water
- xylene
- mixture
- acid
- toluic 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.)
- Expired
Links
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 title claims abstract description 93
- 238000000034 method Methods 0.000 title claims description 56
- 238000002360 preparation method Methods 0.000 title description 2
- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 claims abstract description 132
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims abstract description 121
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 73
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 34
- 239000000203 mixture Substances 0.000 claims abstract description 31
- 230000003647 oxidation Effects 0.000 claims abstract description 29
- 239000003054 catalyst Substances 0.000 claims abstract description 28
- 230000001590 oxidative effect Effects 0.000 claims abstract description 12
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910001882 dioxygen Inorganic materials 0.000 claims abstract description 6
- 239000007788 liquid Substances 0.000 claims abstract description 3
- 238000004519 manufacturing process Methods 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 37
- 239000011541 reaction mixture Substances 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 9
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 7
- 239000007800 oxidant agent Substances 0.000 claims description 7
- 229910017052 cobalt Inorganic materials 0.000 claims description 6
- 239000010941 cobalt Substances 0.000 claims description 6
- 229910001385 heavy metal Inorganic materials 0.000 claims description 6
- 238000005406 washing Methods 0.000 claims description 6
- 239000007791 liquid phase Substances 0.000 claims description 5
- 150000002696 manganese Chemical class 0.000 claims description 5
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical group [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims description 4
- 230000003197 catalytic effect Effects 0.000 claims description 4
- 239000006193 liquid solution Substances 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 150000001868 cobalt Chemical class 0.000 claims description 3
- 239000011368 organic material Substances 0.000 claims description 3
- 238000004064 recycling Methods 0.000 claims description 3
- 238000001704 evaporation Methods 0.000 claims 2
- MARCAKLHFUYDJE-UHFFFAOYSA-N 1,2-xylene;hydrate Chemical compound O.CC1=CC=CC=C1C MARCAKLHFUYDJE-UHFFFAOYSA-N 0.000 claims 1
- 150000007524 organic acids Chemical group 0.000 claims 1
- 239000007789 gas Substances 0.000 abstract description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 25
- 229910052760 oxygen Inorganic materials 0.000 description 25
- 239000001301 oxygen Substances 0.000 description 25
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
- 238000010521 absorption reaction Methods 0.000 description 18
- GOUHYARYYWKXHS-UHFFFAOYSA-N 4-formylbenzoic acid Chemical compound OC(=O)C1=CC=C(C=O)C=C1 GOUHYARYYWKXHS-UHFFFAOYSA-N 0.000 description 12
- 239000002904 solvent Substances 0.000 description 10
- 238000002474 experimental method Methods 0.000 description 8
- 238000001816 cooling Methods 0.000 description 7
- 238000005260 corrosion Methods 0.000 description 7
- 230000007797 corrosion Effects 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 239000000543 intermediate Substances 0.000 description 7
- SGGOJYZMTYGPCH-UHFFFAOYSA-L manganese(2+);naphthalene-2-carboxylate Chemical compound [Mn+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 SGGOJYZMTYGPCH-UHFFFAOYSA-L 0.000 description 7
- 239000012190 activator Substances 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- -1 acetic acid Chemical class 0.000 description 4
- 239000000306 component Substances 0.000 description 4
- 229910052748 manganese Inorganic materials 0.000 description 4
- 239000011572 manganese Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000001627 detrimental effect Effects 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- DYNFCHNNOHNJFG-UHFFFAOYSA-N 2-formylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C=O DYNFCHNNOHNJFG-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000006698 induction Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- ZHKHLJQAZYBIIO-UHFFFAOYSA-N 4-methylbenzoic acid;1,4-xylene Chemical group CC1=CC=C(C)C=C1.CC1=CC=C(C(O)=O)C=C1 ZHKHLJQAZYBIIO-UHFFFAOYSA-N 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- WAIPAZQMEIHHTJ-UHFFFAOYSA-N [Cr].[Co] Chemical compound [Cr].[Co] WAIPAZQMEIHHTJ-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 238000001632 acidimetric titration Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 238000005349 anion exchange Methods 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical class [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 description 1
- 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 1
- 239000000463 material Substances 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000005609 naphthenate group Chemical group 0.000 description 1
- FXLOVSHXALFLKQ-UHFFFAOYSA-N p-tolualdehyde Chemical compound CC1=CC=C(C=O)C=C1 FXLOVSHXALFLKQ-UHFFFAOYSA-N 0.000 description 1
- 238000003969 polarography Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000003822 preparative gas chromatography Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical class [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 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
-
- 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
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7644459A GB1542320A (en) | 1976-10-26 | 1976-10-26 | Process for the preparation of aromatic dicarboxylic acids |
| GB44459/76 | 1976-10-26 | ||
| US76498177A | 1977-02-02 | 1977-02-02 | |
| US764,981 | 1977-02-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1105943A true CA1105943A (en) | 1981-07-28 |
Family
ID=26265395
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA289,160A Expired CA1105943A (en) | 1976-10-26 | 1977-10-20 | Process for the preparation of terephthalic acid |
Country Status (18)
| Country | Link |
|---|---|
| JP (1) | JPS5382744A (Direct) |
| AU (1) | AU519680B2 (Direct) |
| BR (1) | BR7707125A (Direct) |
| CA (1) | CA1105943A (Direct) |
| CH (1) | CH622766A5 (Direct) |
| DE (1) | DE2745918C3 (Direct) |
| EG (1) | EG12905A (Direct) |
| ES (1) | ES463559A1 (Direct) |
| FI (1) | FI773153A7 (Direct) |
| FR (1) | FR2369239A1 (Direct) |
| HU (1) | HU177337B (Direct) |
| IE (1) | IE45896B1 (Direct) |
| IT (1) | IT1087970B (Direct) |
| NL (1) | NL177591C (Direct) |
| NO (1) | NO147600C (Direct) |
| PT (1) | PT67185B (Direct) |
| SE (1) | SE7711869L (Direct) |
| YU (1) | YU256777A (Direct) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IN152155B (Direct) * | 1978-10-02 | 1983-11-05 | Labofina Sa | |
| JPS55154939A (en) * | 1979-05-23 | 1980-12-02 | Teijin Ltd | Preparation of benzenecarboxylic acid |
| US4259522A (en) * | 1979-12-17 | 1981-03-31 | Labofina S.A. | Process for the production of isophtahalic acid |
| US4334086A (en) * | 1981-03-16 | 1982-06-08 | Labofina S.A. | Production of terephthalic acid |
| JPS58129528A (ja) * | 1982-01-27 | 1983-08-02 | Nec Corp | 音韻キ−ボ−ド装置 |
| AU2001219354A1 (en) | 2000-01-18 | 2001-07-31 | Inca International S.P.A. | Oxidation of alkyl aromatic compounds to aromatic acids in an aqueous medium |
| JP4859291B2 (ja) * | 2001-06-22 | 2012-01-25 | 株式会社ダイセル | 酸化方法および反応装置 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1153356B (de) * | 1960-03-28 | 1963-08-29 | Hans J Zimmer Verfahrenstechni | Verfahren zur Herstellung von Terephthalsaeure |
| US3883584A (en) * | 1971-11-25 | 1975-05-13 | Teijin Ltd | Process for the preparation of terephthalic acid |
| JPS5536652B2 (Direct) * | 1971-11-25 | 1980-09-22 |
-
1977
- 1977-10-06 CH CH1220477A patent/CH622766A5/fr not_active IP Right Cessation
- 1977-10-12 DE DE2745918A patent/DE2745918C3/de not_active Expired
- 1977-10-18 NL NLAANVRAGE7711417,A patent/NL177591C/xx not_active IP Right Cessation
- 1977-10-20 CA CA289,160A patent/CA1105943A/en not_active Expired
- 1977-10-21 PT PT67185A patent/PT67185B/pt unknown
- 1977-10-21 SE SE7711869A patent/SE7711869L/xx not_active Application Discontinuation
- 1977-10-24 FI FI773153A patent/FI773153A7/fi not_active Application Discontinuation
- 1977-10-24 NO NO773622A patent/NO147600C/no unknown
- 1977-10-25 EG EG609/77A patent/EG12905A/xx active
- 1977-10-25 IE IE2168/77A patent/IE45896B1/en unknown
- 1977-10-25 AU AU30036/77A patent/AU519680B2/en not_active Expired
- 1977-10-25 BR BR7707125A patent/BR7707125A/pt unknown
- 1977-10-25 HU HU77LA920A patent/HU177337B/hu unknown
- 1977-10-26 YU YU02567/77A patent/YU256777A/xx unknown
- 1977-10-26 FR FR7732191A patent/FR2369239A1/fr active Granted
- 1977-10-26 IT IT29006/77A patent/IT1087970B/it active
- 1977-10-26 JP JP12766577A patent/JPS5382744A/ja active Granted
- 1977-10-26 ES ES463559A patent/ES463559A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| PT67185A (fr) | 1977-11-01 |
| DE2745918B2 (de) | 1980-11-06 |
| NO147600C (no) | 1983-05-11 |
| DE2745918A1 (de) | 1978-04-27 |
| NL177591C (nl) | 1985-10-16 |
| BR7707125A (pt) | 1978-07-25 |
| IE45896L (en) | 1978-04-26 |
| IT1087970B (it) | 1985-06-04 |
| AU3003677A (en) | 1979-05-03 |
| FR2369239A1 (fr) | 1978-05-26 |
| NO773622L (no) | 1978-04-27 |
| NL7711417A (nl) | 1978-04-28 |
| NO147600B (no) | 1983-01-31 |
| CH622766A5 (en) | 1981-04-30 |
| JPS5382744A (en) | 1978-07-21 |
| IE45896B1 (en) | 1982-12-29 |
| NL177591B (nl) | 1985-05-17 |
| FR2369239B1 (Direct) | 1983-11-04 |
| YU256777A (en) | 1982-06-30 |
| PT67185B (fr) | 1979-03-22 |
| JPS5645900B2 (Direct) | 1981-10-29 |
| HU177337B (en) | 1981-09-28 |
| SE7711869L (sv) | 1978-04-27 |
| EG12905A (en) | 1980-03-31 |
| ES463559A1 (es) | 1978-07-01 |
| AU519680B2 (en) | 1981-12-17 |
| FI773153A7 (fi) | 1978-04-27 |
| DE2745918C3 (de) | 1981-09-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |