CS212247B2 - Method of making the terephtale acid - Google Patents
Method of making the terephtale acid Download PDFInfo
- Publication number
- CS212247B2 CS212247B2 CS796670A CS667079A CS212247B2 CS 212247 B2 CS212247 B2 CS 212247B2 CS 796670 A CS796670 A CS 796670A CS 667079 A CS667079 A CS 667079A CS 212247 B2 CS212247 B2 CS 212247B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- acid
- water
- oxidation
- xylene
- catalyst
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 15
- 239000002253 acid Substances 0.000 title description 29
- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 claims abstract description 137
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims abstract description 107
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 94
- 239000003054 catalyst Substances 0.000 claims abstract description 84
- 239000000203 mixture Substances 0.000 claims abstract description 62
- 239000011572 manganese Substances 0.000 claims abstract description 31
- 229910052748 manganese Inorganic materials 0.000 claims abstract description 30
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims abstract description 29
- 150000002736 metal compounds Chemical class 0.000 claims abstract description 9
- 150000001869 cobalt compounds Chemical class 0.000 claims abstract description 5
- 238000007254 oxidation reaction Methods 0.000 claims description 78
- 230000003647 oxidation Effects 0.000 claims description 71
- 238000006243 chemical reaction Methods 0.000 claims description 59
- 150000001875 compounds Chemical class 0.000 claims description 28
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 12
- 229910052759 nickel Inorganic materials 0.000 claims description 6
- 229910052684 Cerium Inorganic materials 0.000 claims description 2
- FVFVNNKYKYZTJU-UHFFFAOYSA-N 6-chloro-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(Cl)=N1 FVFVNNKYKYZTJU-UHFFFAOYSA-N 0.000 claims 1
- GWXLDORMOJMVQZ-UHFFFAOYSA-N cerium Chemical compound [Ce] GWXLDORMOJMVQZ-UHFFFAOYSA-N 0.000 claims 1
- 239000002689 soil Substances 0.000 claims 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 abstract description 108
- 239000011541 reaction mixture Substances 0.000 abstract description 56
- 229910017052 cobalt Inorganic materials 0.000 abstract description 25
- 239000010941 cobalt Substances 0.000 abstract description 25
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 abstract description 25
- 230000001590 oxidative effect Effects 0.000 abstract description 10
- 239000007788 liquid Substances 0.000 abstract description 9
- 239000007789 gas Substances 0.000 abstract description 6
- 150000002697 manganese compounds Chemical class 0.000 abstract description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 abstract description 2
- 229910001882 dioxygen Inorganic materials 0.000 abstract description 2
- 238000000034 method Methods 0.000 description 48
- 230000008569 process Effects 0.000 description 38
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 36
- 229910052760 oxygen Inorganic materials 0.000 description 36
- 239000001301 oxygen Substances 0.000 description 36
- GOUHYARYYWKXHS-UHFFFAOYSA-N 4-formylbenzoic acid Chemical compound OC(=O)C1=CC=C(C=O)C=C1 GOUHYARYYWKXHS-UHFFFAOYSA-N 0.000 description 32
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 32
- 239000000047 product Substances 0.000 description 24
- 239000002904 solvent Substances 0.000 description 22
- 239000006227 byproduct Substances 0.000 description 18
- 239000000543 intermediate Substances 0.000 description 18
- 238000002474 experimental method Methods 0.000 description 17
- FXLOVSHXALFLKQ-UHFFFAOYSA-N p-tolualdehyde Chemical compound CC1=CC=C(C=O)C=C1 FXLOVSHXALFLKQ-UHFFFAOYSA-N 0.000 description 15
- 229940011182 cobalt acetate Drugs 0.000 description 14
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 14
- 229910052751 metal Inorganic materials 0.000 description 13
- 239000002184 metal Substances 0.000 description 13
- QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 description 12
- 230000000694 effects Effects 0.000 description 11
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 10
- 229940071125 manganese acetate Drugs 0.000 description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 9
- 229910052794 bromium Inorganic materials 0.000 description 9
- 238000010924 continuous production Methods 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 9
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
- 239000012190 activator Substances 0.000 description 8
- UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 description 8
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 7
- -1 aromatic carboxylic acids Chemical class 0.000 description 7
- 235000019253 formic acid Nutrition 0.000 description 7
- 239000007791 liquid phase Substances 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 238000010521 absorption reaction Methods 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 238000005260 corrosion Methods 0.000 description 6
- 230000007797 corrosion Effects 0.000 description 6
- 239000008096 xylene Substances 0.000 description 6
- 239000005711 Benzoic acid Substances 0.000 description 5
- 230000008901 benefit Effects 0.000 description 5
- 235000010233 benzoic acid Nutrition 0.000 description 5
- 238000004364 calculation method Methods 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 239000012456 homogeneous solution Substances 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000012736 aqueous medium Substances 0.000 description 3
- 238000010923 batch production Methods 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 239000011975 tartaric acid Substances 0.000 description 3
- 150000003738 xylenes Chemical class 0.000 description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 239000005642 Oleic acid Substances 0.000 description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- MQRWBMAEBQOWAF-UHFFFAOYSA-N acetic acid;nickel Chemical compound [Ni].CC(O)=O.CC(O)=O MQRWBMAEBQOWAF-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- VYYLSHUBVSWNIQ-UHFFFAOYSA-L cobalt(2+) manganese(2+) diacetate Chemical compound C(C)(=O)[O-].[Mn+2].C(C)(=O)[O-].[Co+2] VYYLSHUBVSWNIQ-UHFFFAOYSA-L 0.000 description 2
- 238000002485 combustion reaction Methods 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229910001385 heavy metal Inorganic materials 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
- BZDIAFGKSAYYFC-UHFFFAOYSA-N manganese;hydrate Chemical compound O.[Mn] BZDIAFGKSAYYFC-UHFFFAOYSA-N 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 229940078494 nickel acetate Drugs 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- 238000010587 phase diagram Methods 0.000 description 2
- 238000005191 phase separation Methods 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
- 229920000728 polyester Polymers 0.000 description 2
- 230000001737 promoting effect Effects 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 230000002269 spontaneous effect Effects 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- AKUNSTOMHUXJOZ-UHFFFAOYSA-N 1-hydroperoxybutane Chemical compound CCCCOO AKUNSTOMHUXJOZ-UHFFFAOYSA-N 0.000 description 1
- ZHKHLJQAZYBIIO-UHFFFAOYSA-N 4-methylbenzoic acid;1,4-xylene Chemical compound CC1=CC=C(C)C=C1.CC1=CC=C(C(O)=O)C=C1 ZHKHLJQAZYBIIO-UHFFFAOYSA-N 0.000 description 1
- 240000006162 Chenopodium quinoa Species 0.000 description 1
- 206010053567 Coagulopathies Diseases 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 241001668384 Maroga Species 0.000 description 1
- 241000909989 Suphis Species 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 238000001632 acidimetric titration Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 238000005422 blasting Methods 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 150000001734 carboxylic acid salts Chemical class 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 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 description 1
- 150000001785 cerium compounds Chemical class 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000035602 clotting Effects 0.000 description 1
- MZZUATUOLXMCEY-UHFFFAOYSA-N cobalt manganese Chemical compound [Mn].[Co] MZZUATUOLXMCEY-UHFFFAOYSA-N 0.000 description 1
- 238000005112 continuous flow technique Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 239000004459 forage Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 150000002611 lead compounds Chemical class 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000011707 mineral Substances 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
- 239000003960 organic solvent Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 238000005554 pickling Methods 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 238000003969 polarography Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000009958 sewing Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 238000005406 washing Methods 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)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US94764178A | 1978-10-02 | 1978-10-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS212247B2 true CS212247B2 (en) | 1982-03-26 |
Family
ID=25486474
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS796670A CS212247B2 (en) | 1978-10-02 | 1979-10-02 | Method of making the terephtale acid |
Country Status (23)
| Country | Link |
|---|---|
| JP (1) | JPS5549337A (en:Method) |
| AR (1) | AR218771A1 (en:Method) |
| AT (1) | ATA638179A (en:Method) |
| AU (1) | AU5135679A (en:Method) |
| BE (1) | BE879091A (en:Method) |
| BR (1) | BR7906172A (en:Method) |
| CA (1) | CA1145357A (en:Method) |
| CH (1) | CH642343A5 (en:Method) |
| CS (1) | CS212247B2 (en:Method) |
| DE (1) | DE2939510C2 (en:Method) |
| ES (1) | ES484555A0 (en:Method) |
| FI (1) | FI793003A7 (en:Method) |
| FR (1) | FR2438027A1 (en:Method) |
| GB (1) | GB2032432B (en:Method) |
| IN (1) | IN152155B (en:Method) |
| IT (1) | IT1123749B (en:Method) |
| NL (1) | NL7907252A (en:Method) |
| NO (1) | NO150679C (en:Method) |
| PH (1) | PH15083A (en:Method) |
| PL (1) | PL118757B1 (en:Method) |
| PT (1) | PT70249A (en:Method) |
| SE (1) | SE7908072L (en:Method) |
| ZA (1) | ZA795037B (en:Method) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4334086A (en) * | 1981-03-16 | 1982-06-08 | Labofina S.A. | Production of terephthalic acid |
| GB9210832D0 (en) * | 1992-05-21 | 1992-07-08 | Ici Plc | Bromine catalysed oxidation process |
| CN117185933A (zh) * | 2023-09-08 | 2023-12-08 | 宁波美舒医药科技有限公司 | 一种对硝基甲苯气相催化氧化生产对硝基苯甲酸的工艺 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE548214A (en:Method) * | ||||
| BE562102A (en:Method) * | 1956-11-05 | |||
| FR1367025A (fr) * | 1963-06-25 | 1964-07-17 | Du Pont | Procédé d'oxydation de p-xylène |
| US3406196A (en) * | 1964-09-30 | 1968-10-15 | Du Pont | Oxidation of polyalkyl aromatics to polycarboxylic acids |
| US3883584A (en) * | 1971-11-25 | 1975-05-13 | Teijin Ltd | Process for the preparation of terephthalic acid |
| CH622766A5 (en) * | 1976-10-26 | 1981-04-30 | Labofina Sa | Process for the preparation of terephthalic acid |
| GB1542320A (en) * | 1976-10-26 | 1979-03-14 | Labofina Sa | Process for the preparation of aromatic dicarboxylic acids |
| GB2019395B (en) * | 1978-04-24 | 1982-07-28 | Labofina Sa | Production of terephthalic acid from p-xylene |
-
1979
- 1979-07-23 IN IN757/CAL/79A patent/IN152155B/en unknown
- 1979-09-24 ZA ZA00795037A patent/ZA795037B/xx unknown
- 1979-09-26 IT IT26037/79A patent/IT1123749B/it active
- 1979-09-26 FI FI793003A patent/FI793003A7/fi not_active Application Discontinuation
- 1979-09-26 BR BR7906172A patent/BR7906172A/pt unknown
- 1979-09-27 AR AR278233A patent/AR218771A1/es active
- 1979-09-27 CH CH869779A patent/CH642343A5/de not_active IP Right Cessation
- 1979-09-28 ES ES79484555A patent/ES484555A0/es active Granted
- 1979-09-28 PL PL1979218597A patent/PL118757B1/pl unknown
- 1979-09-28 BE BE0/197396A patent/BE879091A/fr not_active IP Right Cessation
- 1979-09-28 SE SE7908072A patent/SE7908072L/xx not_active Application Discontinuation
- 1979-09-28 PT PT70249A patent/PT70249A/pt unknown
- 1979-09-28 GB GB7933672A patent/GB2032432B/en not_active Expired
- 1979-09-28 DE DE2939510A patent/DE2939510C2/de not_active Expired
- 1979-09-28 NL NL7907252A patent/NL7907252A/nl active Search and Examination
- 1979-09-28 NO NO793116A patent/NO150679C/no unknown
- 1979-09-28 AT AT0638179A patent/ATA638179A/de unknown
- 1979-10-01 CA CA000336777A patent/CA1145357A/en not_active Expired
- 1979-10-02 FR FR7924461A patent/FR2438027A1/fr active Granted
- 1979-10-02 AU AU51356/79A patent/AU5135679A/en not_active Abandoned
- 1979-10-02 PH PH23098A patent/PH15083A/en unknown
- 1979-10-02 CS CS796670A patent/CS212247B2/cs unknown
- 1979-10-02 JP JP12725679A patent/JPS5549337A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FR2438027A1 (fr) | 1980-04-30 |
| ES484555A1 (es) | 1980-05-16 |
| JPS5549337A (en) | 1980-04-09 |
| PL118757B1 (en) | 1981-10-31 |
| FR2438027B1 (en:Method) | 1984-08-24 |
| BE879091A (fr) | 1980-03-28 |
| AU5135679A (en) | 1980-04-17 |
| NO793116L (no) | 1980-04-08 |
| AR218771A1 (es) | 1980-06-30 |
| GB2032432A (en) | 1980-05-08 |
| IT7926037A0 (it) | 1979-09-26 |
| ES484555A0 (es) | 1980-05-16 |
| DE2939510A1 (de) | 1980-04-03 |
| DE2939510C2 (de) | 1985-08-01 |
| PH15083A (en) | 1982-07-02 |
| ATA638179A (de) | 1982-01-15 |
| CA1145357A (en) | 1983-04-26 |
| CH642343A5 (de) | 1984-04-13 |
| SE7908072L (sv) | 1980-04-03 |
| FI793003A7 (fi) | 1981-01-01 |
| PL218597A1 (en:Method) | 1980-05-05 |
| PT70249A (en) | 1979-10-01 |
| IN152155B (en:Method) | 1983-11-05 |
| ZA795037B (en) | 1980-09-24 |
| GB2032432B (en) | 1983-02-09 |
| NO150679B (no) | 1984-08-20 |
| IT1123749B (it) | 1986-04-30 |
| BR7906172A (pt) | 1980-05-27 |
| JPH0222057B2 (en:Method) | 1990-05-17 |
| NL7907252A (nl) | 1980-04-08 |
| NO150679C (no) | 1984-11-28 |
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