DE1919335A1 - Fluessigphasenoxydation von p-Xylol zu Terephthalsaeure - Google Patents
Fluessigphasenoxydation von p-Xylol zu TerephthalsaeureInfo
- Publication number
- DE1919335A1 DE1919335A1 DE19691919335 DE1919335A DE1919335A1 DE 1919335 A1 DE1919335 A1 DE 1919335A1 DE 19691919335 DE19691919335 DE 19691919335 DE 1919335 A DE1919335 A DE 1919335A DE 1919335 A1 DE1919335 A1 DE 1919335A1
- Authority
- DE
- Germany
- Prior art keywords
- reactor
- xylene
- liquid
- acetaldehyde
- phase
- 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.)
- Pending
Links
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 title claims description 48
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 title claims description 42
- 230000003647 oxidation Effects 0.000 title claims description 10
- 238000007254 oxidation reaction Methods 0.000 title claims description 10
- 239000007791 liquid phase Substances 0.000 title claims description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 99
- 239000007788 liquid Substances 0.000 claims description 52
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 48
- 239000008096 xylene Substances 0.000 claims description 35
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 33
- 239000007787 solid Substances 0.000 claims description 32
- 239000002002 slurry Substances 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 29
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 26
- 239000001301 oxygen Substances 0.000 claims description 26
- 229910052760 oxygen Inorganic materials 0.000 claims description 26
- 239000012071 phase Substances 0.000 claims description 24
- 239000003054 catalyst Substances 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 18
- 239000007789 gas Substances 0.000 claims description 18
- 239000002243 precursor Substances 0.000 claims description 11
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 229910017052 cobalt Inorganic materials 0.000 claims description 9
- 239000010941 cobalt Substances 0.000 claims description 9
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 9
- 238000010924 continuous production Methods 0.000 claims description 7
- 239000007792 gaseous phase Substances 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000000376 reactant Substances 0.000 claims description 4
- 150000003738 xylenes Chemical class 0.000 claims description 3
- ZBYYWKJVSFHYJL-UHFFFAOYSA-L cobalt(2+);diacetate;tetrahydrate Chemical group O.O.O.O.[Co+2].CC([O-])=O.CC([O-])=O ZBYYWKJVSFHYJL-UHFFFAOYSA-L 0.000 claims description 2
- -1 cobalt carbonate tetrahydrate Chemical compound 0.000 claims 1
- 238000009833 condensation Methods 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- 239000003921 oil Substances 0.000 claims 1
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000002904 solvent Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 5
- 238000011084 recovery Methods 0.000 description 5
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 150000001868 cobalt Chemical class 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- GOUHYARYYWKXHS-UHFFFAOYSA-N 4-formylbenzoic acid Chemical compound OC(=O)C1=CC=C(C=O)C=C1 GOUHYARYYWKXHS-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 150000003842 bromide salts Chemical class 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- 229910021503 Cobalt(II) hydroxide Inorganic materials 0.000 description 1
- 241000711981 Sais Species 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000007743 anodising Methods 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910021446 cobalt carbonate Inorganic materials 0.000 description 1
- 229910000428 cobalt oxide Inorganic materials 0.000 description 1
- ZOTKGJBKKKVBJZ-UHFFFAOYSA-L cobalt(2+);carbonate Chemical compound [Co+2].[O-]C([O-])=O ZOTKGJBKKKVBJZ-UHFFFAOYSA-L 0.000 description 1
- ASKVAEGIVYSGNY-UHFFFAOYSA-L cobalt(ii) hydroxide Chemical compound [OH-].[OH-].[Co+2] ASKVAEGIVYSGNY-UHFFFAOYSA-L 0.000 description 1
- IVMYJDGYRUAWML-UHFFFAOYSA-N cobalt(ii) oxide Chemical compound [Co]=O IVMYJDGYRUAWML-UHFFFAOYSA-N 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000004401 m-toluyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])[H])C(*)=O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229940078552 o-xylene Drugs 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000009958 sewing Methods 0.000 description 1
- 230000009469 supplementation Effects 0.000 description 1
- 230000009466 transformation 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
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US72170468A | 1968-04-16 | 1968-04-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1919335A1 true DE1919335A1 (de) | 1969-10-23 |
Family
ID=24898974
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19691919335 Pending DE1919335A1 (de) | 1968-04-16 | 1969-04-16 | Fluessigphasenoxydation von p-Xylol zu Terephthalsaeure |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE731519A (enExample) |
| DE (1) | DE1919335A1 (enExample) |
| FR (1) | FR2006269A1 (enExample) |
| GB (1) | GB1237298A (enExample) |
| NL (1) | NL6905812A (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2816835A1 (de) * | 1977-04-19 | 1978-10-26 | Mitsubishi Gas Chemical Co | Verfahren zur herstellung von terephtalsaeure durch oxidation von p-tolualdehyd |
| DE2822728A1 (de) * | 1978-05-24 | 1979-11-29 | Asahi Chemical Ind | Verfahren zur herstellung von hochreiner terephthalsaeure |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7692037B2 (en) * | 2004-09-02 | 2010-04-06 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7608733B2 (en) | 2004-09-02 | 2009-10-27 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7495125B2 (en) | 2004-09-02 | 2009-02-24 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7608732B2 (en) | 2005-03-08 | 2009-10-27 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7741515B2 (en) | 2004-09-02 | 2010-06-22 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7582793B2 (en) | 2004-09-02 | 2009-09-01 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7572932B2 (en) | 2004-09-02 | 2009-08-11 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7507857B2 (en) | 2004-09-02 | 2009-03-24 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7381836B2 (en) | 2004-09-02 | 2008-06-03 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7586000B2 (en) | 2004-09-02 | 2009-09-08 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7361784B2 (en) | 2004-09-02 | 2008-04-22 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7390921B2 (en) | 2004-09-02 | 2008-06-24 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7692036B2 (en) | 2004-11-29 | 2010-04-06 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7568361B2 (en) | 2004-09-02 | 2009-08-04 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7589231B2 (en) | 2004-09-02 | 2009-09-15 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7482482B2 (en) | 2004-09-02 | 2009-01-27 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7399882B2 (en) | 2004-09-02 | 2008-07-15 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7910769B2 (en) | 2004-09-02 | 2011-03-22 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7563926B2 (en) | 2004-09-02 | 2009-07-21 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7683210B2 (en) | 2004-09-02 | 2010-03-23 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7504535B2 (en) | 2004-09-02 | 2009-03-17 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7371894B2 (en) | 2004-09-02 | 2008-05-13 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7572936B2 (en) | 2004-09-02 | 2009-08-11 | 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 |
| US7326808B2 (en) | 2006-03-01 | 2008-02-05 | Eastman Chemical Company | Polycarboxylic acid production system employing cooled mother liquor from oxidative digestion as feed to impurity purge system |
| US7816556B2 (en) | 2006-03-01 | 2010-10-19 | Eastman Chemical Company | Polycarboxylic acid production system employing enhanced multistage oxidative digestion |
| US7772424B2 (en) | 2006-03-01 | 2010-08-10 | Eastman Chemical Company | Polycarboxylic acid production system employing enhanced evaporative concentration downstream of oxidative digestion |
| US7420082B2 (en) * | 2006-03-01 | 2008-09-02 | Eastman Chemical Company | Polycarboxylic acid production system employing hot liquor removal downstream of oxidative digestion |
| US20070208194A1 (en) | 2006-03-01 | 2007-09-06 | Woodruff Thomas E | Oxidation system with sidedraw secondary reactor |
| US7393973B2 (en) | 2006-03-01 | 2008-07-01 | Eastman Chemical Company | Polycarboxylic acid production system with enhanced residence time distribution for oxidative digestion |
| US7501537B2 (en) | 2006-03-01 | 2009-03-10 | Eastman Chemical Company | Polycarboxylic acid production system employing oxidative digestion with reduced or eliminated upstream liquor exchange |
-
1969
- 1969-04-14 FR FR6911430A patent/FR2006269A1/fr not_active Withdrawn
- 1969-04-15 BE BE731519D patent/BE731519A/xx unknown
- 1969-04-15 NL NL6905812A patent/NL6905812A/xx unknown
- 1969-04-16 DE DE19691919335 patent/DE1919335A1/de active Pending
- 1969-04-16 GB GB1932769A patent/GB1237298A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2816835A1 (de) * | 1977-04-19 | 1978-10-26 | Mitsubishi Gas Chemical Co | Verfahren zur herstellung von terephtalsaeure durch oxidation von p-tolualdehyd |
| DE2822728A1 (de) * | 1978-05-24 | 1979-11-29 | Asahi Chemical Ind | Verfahren zur herstellung von hochreiner terephthalsaeure |
Also Published As
| Publication number | Publication date |
|---|---|
| BE731519A (enExample) | 1969-10-15 |
| GB1237298A (en) | 1971-06-30 |
| NL6905812A (enExample) | 1969-10-20 |
| FR2006269A1 (enExample) | 1969-12-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1919335A1 (de) | Fluessigphasenoxydation von p-Xylol zu Terephthalsaeure | |
| DE69506462T2 (de) | Verfahren zur Herstellung von aromatischer Carbonsäure | |
| US3880921A (en) | Process for the continuous production of saturated aliphatic dicarboxylic acids | |
| DE69924523T3 (de) | Verfahren zur herstellung aromatischer carbonsäuren | |
| WO2003078369A1 (de) | Oxidation von o-xylol zu o-tolylsäure und anderen oxidationsprodukten durch gestaffelte zufuhr eines sauerstoffhaltigen gases | |
| DE1168887B (de) | Vorrichtung zur katalytischen Oxydation von Kohlenwasserstoffen | |
| DE3047474A1 (de) | Verfahren bzw. vorrichtung zur kontinuierlichen herstellung von polyester | |
| DE69120973T2 (de) | Kontinuierliche herstellung von aromatischen carbonsäuren | |
| DE2053115C3 (de) | Verfahren zur kontinuierlichen Durchführung heterogener katalytischer Reaktionen in flüssiger Phase im Fließbett | |
| DE1618653B2 (de) | Verfahren zur herstellung von terephthalsaeure | |
| DE1768289B2 (de) | Verfahren zur herstellung von vinylestern, gesaettigter monocarbonsaeuren bzw. von gemischen solcher ester | |
| DE3110765A1 (de) | Katalytische butanoxidation in fluessiger phase | |
| DE69526263T2 (de) | Oxydation von sekundären Alkoholen | |
| DE1493191B2 (de) | Verfahren zur Herstellung von Benzolpolycarbonsäuren | |
| DE2053196A1 (de) | Verfahren zur katalytischen Spaltung von Aralkylhydroperoxiden | |
| DE1418852C (enExample) | ||
| DE3044752A1 (de) | Verfahren zur herstellung von trimellitsaeure | |
| DE2632898A1 (de) | Kobaltkatalysierte oxidation von gesaettigten, aliphatischen c tief 3 - c tief 7 -kohlenwasserstoffen zu essigsaeure | |
| DE886908C (de) | Verfahren zur katalytischen Dehydrierung von Kohlenwasserstoffen | |
| DE850604C (de) | Verfahren zur Herstellung von wasserstoffhaltigen Gasen | |
| DE2201761C3 (de) | Verfahren zur Herstellung von Terephthalsäure | |
| DE926846C (de) | Verfahren zur Durchfuehrung exothermer Reaktionen, an denen Gase oder Daempfe und Fluessigkeiten beteiligt sind | |
| DE1294361B (de) | Verfahren zur Herstellung von Essigsaeure und Butylacetat | |
| EP1317491A1 (de) | Verfahren zur kontinuierlichen hydroformylierung von polyalkenen mit 30 bis 700 kohlenstoffatomen | |
| DE971554C (de) | Verfahren und Vorrichtung zur Herstellung von Carbonsaeuren durch Oxydation organischer Stoffe mit Salpetersaeure |