DE1235887B - Verfahren und Vorrichtung zur kontinuierlichen Herstellung von Benzoldicarbonsaeuren - Google Patents
Verfahren und Vorrichtung zur kontinuierlichen Herstellung von BenzoldicarbonsaeurenInfo
- Publication number
- DE1235887B DE1235887B DEE23273A DEE0023273A DE1235887B DE 1235887 B DE1235887 B DE 1235887B DE E23273 A DEE23273 A DE E23273A DE E0023273 A DEE0023273 A DE E0023273A DE 1235887 B DE1235887 B DE 1235887B
- Authority
- DE
- Germany
- Prior art keywords
- acid
- devices
- acetic acid
- reaction
- reaction zone
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims description 19
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical class OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 title claims description 13
- 238000010924 continuous production Methods 0.000 title claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 63
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 60
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 36
- 238000006243 chemical reaction Methods 0.000 claims description 36
- 239000003054 catalyst Substances 0.000 claims description 27
- 230000003647 oxidation Effects 0.000 claims description 27
- 238000007254 oxidation reaction Methods 0.000 claims description 27
- 239000008096 xylene Substances 0.000 claims description 22
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 17
- 239000007789 gas Substances 0.000 claims description 16
- 239000007800 oxidant agent Substances 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 12
- 239000010941 cobalt Substances 0.000 claims description 12
- 229910017052 cobalt Inorganic materials 0.000 claims description 12
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 12
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 claims description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
- 239000001301 oxygen Substances 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 239000002245 particle Substances 0.000 claims description 9
- 239000007788 liquid Substances 0.000 claims description 8
- 239000000463 material Substances 0.000 claims description 7
- 239000010802 sludge Substances 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims description 6
- 239000011572 manganese Substances 0.000 claims description 6
- 229910052748 manganese Inorganic materials 0.000 claims description 6
- 229940011182 cobalt acetate Drugs 0.000 claims description 5
- 238000005406 washing Methods 0.000 claims description 5
- 150000003738 xylenes Chemical class 0.000 claims description 5
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- 229940071125 manganese acetate Drugs 0.000 claims description 4
- UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 claims description 4
- 239000002002 slurry Substances 0.000 claims description 4
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 2
- YBCVMFKXIKNREZ-UHFFFAOYSA-N acoh acetic acid Chemical compound CC(O)=O.CC(O)=O YBCVMFKXIKNREZ-UHFFFAOYSA-N 0.000 claims 1
- 229910001882 dioxygen Inorganic materials 0.000 claims 1
- 238000009826 distribution Methods 0.000 claims 1
- 238000001704 evaporation Methods 0.000 claims 1
- 230000008020 evaporation Effects 0.000 claims 1
- 230000000630 rising effect Effects 0.000 claims 1
- 239000000725 suspension Substances 0.000 claims 1
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
- 230000001590 oxidative effect Effects 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- TYGDMAQFSSHPRP-UHFFFAOYSA-N acetaldehyde;acetic acid Chemical compound CC=O.CC(O)=O TYGDMAQFSSHPRP-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- -1 aldehyde activated cobalt Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002697 manganese compounds Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 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
-
- 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
- C07C51/23—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of oxygen-containing groups to carboxyl groups
- C07C51/235—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of oxygen-containing groups to carboxyl groups of —CHO groups or primary alcohol 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 |
|---|---|---|---|
| US131144A US3240803A (en) | 1961-08-14 | 1961-08-14 | Preparation of benzenecarboxylic acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1235887B true DE1235887B (de) | 1967-03-09 |
| DE1235887C2 DE1235887C2 (en, 2012) | 1967-09-21 |
Family
ID=22448093
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEE23273A Granted DE1235887B (de) | 1961-08-14 | 1962-07-27 | Verfahren und Vorrichtung zur kontinuierlichen Herstellung von Benzoldicarbonsaeuren |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3240803A (en, 2012) |
| BE (1) | BE621323A (en, 2012) |
| DE (1) | DE1235887B (en, 2012) |
| FR (1) | FR1348386A (en, 2012) |
| GB (1) | GB1017373A (en, 2012) |
| NL (1) | NL282031A (en, 2012) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0002749A1 (en) * | 1977-12-26 | 1979-07-11 | IHARA CHEMICAL INDUSTRY Co., Ltd. | Process for producing aromatic monocarboxylic acid |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3626000A (en) * | 1968-01-05 | 1971-12-07 | Toray Industries | Process for preparing benzene carboxylic acids |
| US3626001A (en) * | 1968-05-09 | 1971-12-07 | Atlantic Richfield Co | Method for the production of high-purity isophthalic or terephthalic acid |
| US3683018A (en) * | 1969-05-26 | 1972-08-08 | Standard Oil Co | Integrated oxidation of isomeric xylene mixture to isomeric phthalic acid mixture and separation of mixture of isomeric phthalic acids into individual isomer products |
| US3686293A (en) * | 1970-07-13 | 1972-08-22 | Giorgio Gualdi | Process for the preparation of aromatic carboxylic acids |
| US4230882A (en) * | 1978-05-19 | 1980-10-28 | Asahi Kasei Kogyo Kabushiki Kaisha | Process for the production of a high purity terephthalic acid |
| US7608732B2 (en) * | 2005-03-08 | 2009-10-27 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| RU2388743C2 (ru) * | 2004-09-02 | 2010-05-10 | Истман Кемикал Компани | Оптимизированное жидкофазное окисление |
| US7563926B2 (en) * | 2004-09-02 | 2009-07-21 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| RU2381212C2 (ru) * | 2004-09-02 | 2010-02-10 | Истман Кемикал Компани | Оптимизированное жидкофазное окисление |
| US7741515B2 (en) | 2004-09-02 | 2010-06-22 | 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 |
| US7572932B2 (en) | 2004-09-02 | 2009-08-11 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7586000B2 (en) * | 2004-09-02 | 2009-09-08 | 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 |
| US20060047153A1 (en) * | 2004-09-02 | 2006-03-02 | Wonders Alan G | Optimized liquid-phase oxidation |
| US7399882B2 (en) * | 2004-09-02 | 2008-07-15 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7390921B2 (en) * | 2004-09-02 | 2008-06-24 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7482482B2 (en) * | 2004-09-02 | 2009-01-27 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7381836B2 (en) * | 2004-09-02 | 2008-06-03 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7495125B2 (en) * | 2004-09-02 | 2009-02-24 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7910769B2 (en) * | 2004-09-02 | 2011-03-22 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| MX2007002283A (es) * | 2004-09-02 | 2007-04-23 | Eastman Chem Co | Oxidacion en fase liquida optimizada. |
| US7507857B2 (en) * | 2004-09-02 | 2009-03-24 | 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 |
| US7683210B2 (en) * | 2004-09-02 | 2010-03-23 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7692037B2 (en) * | 2004-09-02 | 2010-04-06 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7582793B2 (en) * | 2004-09-02 | 2009-09-01 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7608733B2 (en) * | 2004-09-02 | 2009-10-27 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7504535B2 (en) | 2004-09-02 | 2009-03-17 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US20060116531A1 (en) * | 2004-11-29 | 2006-06-01 | Wonders Alan G | Modeling of 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 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2245528A (en) * | 1938-10-18 | 1941-06-10 | Du Pont | Catalytic oxidation of alkyl substituted aromatic compounds |
| US2673217A (en) * | 1951-09-21 | 1954-03-23 | Eastman Kodak Co | Selective oxidation of substituted aromatic compounds using aldehyde-activated catalysts |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1902550A (en) * | 1930-01-31 | 1933-03-21 | Nat Synthetic Corp | Process of oxidizing cyclic organic compounds |
| US2479067A (en) * | 1947-06-05 | 1949-08-16 | Du Pont | Preparation of terephthalic acid |
| US2547684A (en) * | 1948-02-12 | 1951-04-03 | Manuf De Caoutchouc Michelin P | Plant for the continuous manufacture of isoprene |
| US2723994A (en) * | 1951-01-15 | 1955-11-15 | Shell Dev | Oxidation of xylene and toluic acid mixtures to phthalic acids |
| US2848483A (en) * | 1953-12-31 | 1958-08-19 | Sun Oil Co | Separation of xylenes |
| US2926074A (en) * | 1954-04-30 | 1960-02-23 | Phillips Petroleum Co | Apparatus for production of substituted pyridines |
| NL197526A (en, 2012) * | 1954-05-27 | |||
| US2794832A (en) * | 1955-06-20 | 1957-06-04 | Shell Dev | Crystallization and separation of crystals |
| US2837584A (en) * | 1955-10-31 | 1958-06-03 | Standard Oil Co | Process for production of durene |
| US2890245A (en) * | 1957-02-25 | 1959-06-09 | Sun Oil Co | Partial oxidation of hydrocarbons |
| US2962361A (en) * | 1957-08-12 | 1960-11-29 | Standard Oil Co | Continuous oxidation system for producing carboxylic acids |
-
0
- NL NL282031D patent/NL282031A/xx unknown
- BE BE621323D patent/BE621323A/xx unknown
-
1961
- 1961-08-14 US US131144A patent/US3240803A/en not_active Expired - Lifetime
-
1962
- 1962-07-18 GB GB27543/62A patent/GB1017373A/en not_active Expired
- 1962-07-27 DE DEE23273A patent/DE1235887B/de active Granted
- 1962-08-10 FR FR906715A patent/FR1348386A/fr not_active Expired
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2245528A (en) * | 1938-10-18 | 1941-06-10 | Du Pont | Catalytic oxidation of alkyl substituted aromatic compounds |
| US2673217A (en) * | 1951-09-21 | 1954-03-23 | Eastman Kodak Co | Selective oxidation of substituted aromatic compounds using aldehyde-activated catalysts |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0002749A1 (en) * | 1977-12-26 | 1979-07-11 | IHARA CHEMICAL INDUSTRY Co., Ltd. | Process for producing aromatic monocarboxylic acid |
Also Published As
| Publication number | Publication date |
|---|---|
| NL282031A (en, 2012) | |
| DE1235887C2 (en, 2012) | 1967-09-21 |
| GB1017373A (en) | 1966-01-19 |
| BE621323A (en, 2012) | |
| FR1348386A (fr) | 1964-01-10 |
| US3240803A (en) | 1966-03-15 |
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