JPS6241219B2 - - Google Patents
Info
- Publication number
- JPS6241219B2 JPS6241219B2 JP53038175A JP3817578A JPS6241219B2 JP S6241219 B2 JPS6241219 B2 JP S6241219B2 JP 53038175 A JP53038175 A JP 53038175A JP 3817578 A JP3817578 A JP 3817578A JP S6241219 B2 JPS6241219 B2 JP S6241219B2
- Authority
- JP
- Japan
- Prior art keywords
- column
- water
- distillation
- isobutyl acetate
- terephthalic 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
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 86
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 41
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 35
- 238000000034 method Methods 0.000 claims description 33
- 238000004821 distillation Methods 0.000 claims description 25
- 239000012452 mother liquor Substances 0.000 claims description 25
- 238000007254 oxidation reaction Methods 0.000 claims description 25
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 claims description 22
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 claims description 22
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 claims description 22
- 230000003647 oxidation Effects 0.000 claims description 22
- 239000003054 catalyst Substances 0.000 claims description 19
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 16
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 16
- 239000007788 liquid Substances 0.000 claims description 13
- 230000018044 dehydration Effects 0.000 claims description 12
- 238000006297 dehydration reaction Methods 0.000 claims description 12
- 239000007787 solid Substances 0.000 claims description 12
- 238000010533 azeotropic distillation Methods 0.000 claims description 10
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims description 8
- 230000015572 biosynthetic process Effects 0.000 claims description 7
- 238000003786 synthesis reaction Methods 0.000 claims description 7
- 239000008346 aqueous phase Substances 0.000 claims description 6
- 229910017052 cobalt Inorganic materials 0.000 claims description 6
- 239000010941 cobalt Substances 0.000 claims description 6
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 6
- 238000010992 reflux Methods 0.000 claims description 6
- 239000012074 organic phase Substances 0.000 claims description 5
- 238000000926 separation method Methods 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 239000006227 byproduct Substances 0.000 claims description 2
- 238000007599 discharging Methods 0.000 claims 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 claims 1
- 239000012044 organic layer Substances 0.000 claims 1
- 230000002194 synthesizing effect Effects 0.000 claims 1
- 238000010926 purge Methods 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 238000011084 recovery Methods 0.000 description 7
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 5
- 229910052748 manganese Inorganic materials 0.000 description 5
- 239000011572 manganese Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000007789 gas Substances 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- 238000009825 accumulation Methods 0.000 description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- -1 iron ions Chemical class 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 230000008929 regeneration Effects 0.000 description 2
- 238000011069 regeneration method Methods 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- DYNFCHNNOHNJFG-UHFFFAOYSA-N 2-formylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C=O DYNFCHNNOHNJFG-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 238000007701 flash-distillation Methods 0.000 description 1
- 239000007792 gaseous phase Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000007420 reactivation Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000002834 transmittance 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
- Y02P20/584—Recycling of 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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2205877A IT1075688B (it) | 1977-04-04 | 1977-04-04 | Metodo per il recupero del catalizzatore e del solvente dal liquido madre di un processo per la sintesi dell'acido tereftalico |
| IT22408/77A IT1075317B (it) | 1977-04-13 | 1977-04-13 | Metodo per l'anidrificazione del solvente e per il ricupero del sottoprodotto acetato di metile in un processo di sintesi dell'acido tereftalico |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS53127430A JPS53127430A (en) | 1978-11-07 |
| JPS6241219B2 true JPS6241219B2 (ro) | 1987-09-02 |
Family
ID=26328080
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3817578A Granted JPS53127430A (en) | 1977-04-04 | 1978-04-03 | Improved method of recovering catalyst and solvent from mother liquid of phthalic acid synthesizing process |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS53127430A (ro) |
| BR (1) | BR7802069A (ro) |
| DE (1) | DE2814448A1 (ro) |
| ES (1) | ES468499A1 (ro) |
| FR (1) | FR2386511A1 (ro) |
| GB (1) | GB1593117A (ro) |
| IN (1) | IN148106B (ro) |
| MX (1) | MX148713A (ro) |
| NL (1) | NL188282C (ro) |
| SU (1) | SU1217250A3 (ro) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1129759B (it) * | 1980-01-23 | 1986-06-11 | Montedison Spa | Metodo per ricuperare in forma attiva i componenti del sistema catalitico della sintesi dell'acido tereftalico |
| US4334086A (en) * | 1981-03-16 | 1982-06-08 | Labofina S.A. | Production of terephthalic acid |
| ATE182576T1 (de) * | 1994-08-23 | 1999-08-15 | Du Pont | Dehydratisierung der essigsäure durch azeotropische destillation in der herstellung von aromatischen säure |
| US6150553A (en) * | 1998-08-11 | 2000-11-21 | E. I. Du Pont De Nemours And Company | Method for recovering methyl acetate and residual acetic acid in the production acid of pure terephthalic acid |
| WO2002068083A1 (fr) * | 2001-02-27 | 2002-09-06 | Mitsubishi Chemical Corporation | Methode de distillation azeotropique |
| US7504535B2 (en) | 2004-09-02 | 2009-03-17 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7568361B2 (en) | 2004-09-02 | 2009-08-04 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7361784B2 (en) * | 2004-09-02 | 2008-04-22 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7589231B2 (en) | 2004-09-02 | 2009-09-15 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7582793B2 (en) | 2004-09-02 | 2009-09-01 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7741515B2 (en) | 2004-09-02 | 2010-06-22 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7507857B2 (en) | 2004-09-02 | 2009-03-24 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7572936B2 (en) | 2004-09-02 | 2009-08-11 | 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 |
| US7910769B2 (en) | 2004-09-02 | 2011-03-22 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7692037B2 (en) | 2004-09-02 | 2010-04-06 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7692036B2 (en) | 2004-11-29 | 2010-04-06 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7884232B2 (en) | 2005-06-16 | 2011-02-08 | Eastman Chemical Company | Optimized liquid-phase oxidation |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA793870A (en) * | 1964-12-14 | 1968-09-03 | Berthoux Jean | Procede d'oxydation d'hydrocarbures aromatiques |
| US3557173A (en) * | 1968-05-09 | 1971-01-19 | Sinclair Research Inc | Process for recovering cobalt acetate |
| DE2104909A1 (en) * | 1971-02-03 | 1972-09-07 | Chemische Fabrik Kalk GmbH, 5000 Köln | Terephthalic acid prodn - by para-xylene oxidn with oxygen using cobalt and bromine compound catalysts |
| US3761474A (en) * | 1971-03-22 | 1973-09-25 | Fmc Corp | Purification of crude cyanuric acid |
| JPS5328420B2 (ro) * | 1973-04-05 | 1978-08-15 | ||
| JPS5328421B2 (ro) * | 1973-05-15 | 1978-08-15 | ||
| JPS5328901B2 (ro) * | 1973-07-28 | 1978-08-17 | ||
| FR2304255A7 (fr) * | 1975-03-13 | 1976-10-08 | Inst Francais Du Petrole | Procede de fabrication d'acide terephtalique par oxydation du paraxylene |
-
1978
- 1978-03-30 NL NLAANVRAGE7803368,A patent/NL188282C/xx not_active IP Right Cessation
- 1978-03-31 FR FR7809488A patent/FR2386511A1/fr active Granted
- 1978-04-03 JP JP3817578A patent/JPS53127430A/ja active Granted
- 1978-04-03 SU SU782600750A patent/SU1217250A3/ru active
- 1978-04-03 GB GB12977/78A patent/GB1593117A/en not_active Expired
- 1978-04-03 IN IN356/CAL/78A patent/IN148106B/en unknown
- 1978-04-03 ES ES468499A patent/ES468499A1/es not_active Expired
- 1978-04-03 BR BR7802069A patent/BR7802069A/pt unknown
- 1978-04-03 MX MX172975A patent/MX148713A/es unknown
- 1978-04-04 DE DE19782814448 patent/DE2814448A1/de active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FR2386511A1 (fr) | 1978-11-03 |
| DE2814448C2 (ro) | 1991-05-23 |
| BR7802069A (pt) | 1979-01-23 |
| DE2814448A1 (de) | 1978-10-12 |
| NL7803368A (nl) | 1978-10-06 |
| NL188282C (nl) | 1992-05-18 |
| FR2386511B1 (ro) | 1980-07-25 |
| GB1593117A (en) | 1981-07-15 |
| SU1217250A3 (ru) | 1986-03-07 |
| NL188282B (nl) | 1991-12-16 |
| ES468499A1 (es) | 1979-01-01 |
| JPS53127430A (en) | 1978-11-07 |
| MX148713A (es) | 1983-06-06 |
| IN148106B (ro) | 1980-10-18 |
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