GB892766A - Improvements in or relating to the production of aromatic acids - Google Patents
Improvements in or relating to the production of aromatic acidsInfo
- Publication number
- GB892766A GB892766A GB36234/58A GB3623458A GB892766A GB 892766 A GB892766 A GB 892766A GB 36234/58 A GB36234/58 A GB 36234/58A GB 3623458 A GB3623458 A GB 3623458A GB 892766 A GB892766 A GB 892766A
- Authority
- GB
- United Kingdom
- Prior art keywords
- oxidation
- catalyst
- bottoms
- distillation
- 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
- 159000000032 aromatic acids Chemical class 0.000 title 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 9
- 239000003054 catalyst Substances 0.000 abstract 9
- 238000007254 oxidation reaction Methods 0.000 abstract 7
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract 5
- 239000000284 extract Substances 0.000 abstract 4
- 230000003647 oxidation Effects 0.000 abstract 4
- 150000001491 aromatic compounds Chemical class 0.000 abstract 3
- 239000005711 Benzoic acid Substances 0.000 abstract 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 abstract 2
- 235000010233 benzoic acid Nutrition 0.000 abstract 2
- 239000006227 byproduct Substances 0.000 abstract 2
- 239000012442 inert solvent Substances 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- 239000000047 product Substances 0.000 abstract 2
- 239000007787 solid Substances 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- 229910052684 Cerium Inorganic materials 0.000 abstract 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 abstract 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 abstract 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 abstract 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 abstract 1
- 229910052779 Neodymium Inorganic materials 0.000 abstract 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- GWXLDORMOJMVQZ-UHFFFAOYSA-N cerium Chemical compound [Ce] GWXLDORMOJMVQZ-UHFFFAOYSA-N 0.000 abstract 1
- 229910052804 chromium Inorganic materials 0.000 abstract 1
- 239000011651 chromium Substances 0.000 abstract 1
- 229940011182 cobalt acetate Drugs 0.000 abstract 1
- QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 abstract 1
- 229910001882 dioxygen Inorganic materials 0.000 abstract 1
- 238000004821 distillation Methods 0.000 abstract 1
- 238000000605 extraction Methods 0.000 abstract 1
- 239000012065 filter cake Substances 0.000 abstract 1
- 239000000706 filtrate Substances 0.000 abstract 1
- 229910001385 heavy metal Inorganic materials 0.000 abstract 1
- 150000002531 isophthalic acids Chemical class 0.000 abstract 1
- 229910052748 manganese Inorganic materials 0.000 abstract 1
- 239000011572 manganese Substances 0.000 abstract 1
- 229940071125 manganese acetate Drugs 0.000 abstract 1
- 229910052750 molybdenum Inorganic materials 0.000 abstract 1
- 239000011733 molybdenum Substances 0.000 abstract 1
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 abstract 1
- QEFYFXOXNSNQGX-UHFFFAOYSA-N neodymium atom Chemical compound [Nd] QEFYFXOXNSNQGX-UHFFFAOYSA-N 0.000 abstract 1
- 229910052759 nickel Inorganic materials 0.000 abstract 1
- 239000003208 petroleum Substances 0.000 abstract 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 abstract 1
- 150000003022 phthalic acids Chemical class 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 238000004064 recycling Methods 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 150000003504 terephthalic acids Chemical class 0.000 abstract 1
- 229910052718 tin Inorganic materials 0.000 abstract 1
- 239000011135 tin Substances 0.000 abstract 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 abstract 1
- 229910052721 tungsten Inorganic materials 0.000 abstract 1
- 239000010937 tungsten Substances 0.000 abstract 1
- 229910052720 vanadium Inorganic materials 0.000 abstract 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 abstract 1
- 239000008096 xylene Substances 0.000 abstract 1
- 150000003738 xylenes Chemical class 0.000 abstract 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/90—Regeneration or reactivation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/48—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
-
- 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)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
In a process for the oxidation with molecular oxygen, of an aliphatic-substituted aromatic compound or a fused-ring aromatic compound, dissolved in an inert solvent and in the presence of a heavy metal oxidation-catalyst, advantageously promoted by bromine or bromide ions, the oxidation-product is submitted to distillation to separate the inert solvent and, if desired, part of the aromatic acid product, and the distillation-bottoms are extracted with water or a lower aliphatic or naphthenic monocarboxylic acid in order to separate tar-like by-products from the catalyst so that the latter may be reused in the oxidation reaction. The extraction is preferably carried out with between 3 and 50 volumes of solvent per volume of bottoms, and at a temperature between 50 DEG C. and 150 DEG C. In some cases, the catalyst extract may be used in the oxidation; in other cases the catalyst is separated from the extract so that the catalyst alone may be recycled. In an example, a reaction-mixture from the air-oxidation of mixed petroleum xylenes in acetic acid and in the presence of a bromine-promoted manganese and cobalt acetate catalyst, is cooled and filtered, whereby a filter-cake comprising ortho-, iso-, and terephthalic acids is obtained. The filtrate is distilled at atmospheric pressure to remove acetic acid and water-of-oxidation, leaving a solid residue which contains catalyst, benzoic acid, toluic acids and phthalic acids. This residue is distilled under an absolute pressure of 40 mm. to remove benzoic acid and some of the orthophthalic acid (as anhydride). The distillation-bottoms is divided into two portions. One portion is pulverized and extracted with hot water; and the other portion is pulverized and extracted with hot acetic acid. Both extracts are filtered and evaporated to dryness whereby two pale-coloured solids are obtained, which are found to contain over 90% of the catalyst in the distillation-bottoms but only minor proportions of tar-like oxidation by-products. Both extracts are suitable for recycling to a subsequent oxidation step. A list of aromatic compounds which may be oxidized according to the process of the invention is given in the Specification; also a list of catalysts, which includes nickel, chromium, vanadium, molybdenum, tungsten, tin, neodymium and cerium.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US892766XA | 1957-11-12 | 1957-11-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB892766A true GB892766A (en) | 1962-03-28 |
Family
ID=22216713
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB36234/58A Expired GB892766A (en) | 1957-11-12 | 1958-11-11 | Improvements in or relating to the production of aromatic acids |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB892766A (en) |
Cited By (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4459365A (en) * | 1981-05-29 | 1984-07-10 | Mitsubishi Gas Chemical Company, Inc. | Method of recovering a catalytic metal |
| WO2007021487A3 (en) * | 2005-08-11 | 2007-05-03 | Eastman Chem Co | Process for removal of benzoic acid from an oxidizer purge stream |
| US7273559B2 (en) | 2004-10-28 | 2007-09-25 | Eastman Chemical Company | Process for removal of impurities from an oxidizer purge stream |
| US7282151B2 (en) | 2003-06-05 | 2007-10-16 | Eastman Chemical Company | Process for removal of impurities from mother liquor in the synthesis of carboxylic acid using pressure filtration |
| US7291270B2 (en) | 2004-10-28 | 2007-11-06 | Eastman Chemical Company | Process for removal of impurities from an oxidizer purge stream |
| US7351396B2 (en) | 2003-06-05 | 2008-04-01 | Eastman Chemical Company | Extraction process for removal of impurities from an aqueous mixture |
| US7381386B2 (en) | 2003-06-05 | 2008-06-03 | Eastman Chemical Company | Extraction process for removal of impurities from mother liquor in the synthesis of carboxylic acid |
| US7402694B2 (en) | 2005-08-11 | 2008-07-22 | Eastman Chemical Company | Process for removal of benzoic acid from an oxidizer purge stream |
| US7410632B2 (en) | 2003-06-05 | 2008-08-12 | Eastman Chemical Company | Extraction process for removal of impurities from mother liquor in the synthesis of carboxylic acid |
| US7452522B2 (en) | 2003-06-05 | 2008-11-18 | Eastman Chemical Company | Extraction process for removal of impurities from an oxidizer purge stream in the synthesis of carboxylic acid |
| US7494641B2 (en) | 2003-06-05 | 2009-02-24 | Eastman Chemical Company | Extraction process for removal of impurities from an oxidizer purge stream in the synthesis of carboxylic acid |
| US7556784B2 (en) | 2004-09-02 | 2009-07-07 | Eastman Chemical Company | Optimized production of aromatic dicarboxylic acids |
| US7569722B2 (en) | 2005-08-11 | 2009-08-04 | Eastman Chemical Company | Process for removal of benzoic acid from an oxidizer purge stream |
| US7759516B2 (en) | 2006-03-01 | 2010-07-20 | Eastman Chemical Company | Versatile oxidation byproduct purge process |
| US7863481B2 (en) | 2006-03-01 | 2011-01-04 | Eastman Chemical Company | Versatile oxidation byproduct purge process |
| US7880032B2 (en) | 2006-03-01 | 2011-02-01 | Eastman Chemical Company | Versatile oxidation byproduct purge process |
| US7888530B2 (en) | 2004-09-02 | 2011-02-15 | Eastman Chemical Company | Optimized production of aromatic dicarboxylic acids |
| US7897808B2 (en) | 2006-03-01 | 2011-03-01 | Eastman Chemical Company | Versatile oxidation byproduct purge process |
| US7897810B2 (en) | 2004-09-02 | 2011-03-01 | Eastman Chemical Company | Optimized production of aromatic dicarboxylic acids |
| WO2015088820A1 (en) * | 2013-12-12 | 2015-06-18 | Saudi Arabian Oil Company | Liquid phase oxidation of aromatic feedstocks with manganate recycling to produce carboxylic acids |
-
1958
- 1958-11-11 GB GB36234/58A patent/GB892766A/en not_active Expired
Cited By (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4459365A (en) * | 1981-05-29 | 1984-07-10 | Mitsubishi Gas Chemical Company, Inc. | Method of recovering a catalytic metal |
| US7410632B2 (en) | 2003-06-05 | 2008-08-12 | Eastman Chemical Company | Extraction process for removal of impurities from mother liquor in the synthesis of carboxylic acid |
| US7494641B2 (en) | 2003-06-05 | 2009-02-24 | Eastman Chemical Company | Extraction process for removal of impurities from an oxidizer purge stream in the synthesis of carboxylic acid |
| US7282151B2 (en) | 2003-06-05 | 2007-10-16 | Eastman Chemical Company | Process for removal of impurities from mother liquor in the synthesis of carboxylic acid using pressure filtration |
| US7470370B2 (en) | 2003-06-05 | 2008-12-30 | Eastman Chemical Company | Process for removal of impurities from mother liquor in the synthesis of carboxylic acid using pressure filtration |
| US7351396B2 (en) | 2003-06-05 | 2008-04-01 | Eastman Chemical Company | Extraction process for removal of impurities from an aqueous mixture |
| US7381386B2 (en) | 2003-06-05 | 2008-06-03 | Eastman Chemical Company | Extraction process for removal of impurities from mother liquor in the synthesis of carboxylic acid |
| US7452522B2 (en) | 2003-06-05 | 2008-11-18 | Eastman Chemical Company | Extraction process for removal of impurities from an oxidizer purge stream in the synthesis of carboxylic acid |
| US7556784B2 (en) | 2004-09-02 | 2009-07-07 | Eastman Chemical Company | Optimized production of aromatic dicarboxylic acids |
| US7888530B2 (en) | 2004-09-02 | 2011-02-15 | Eastman Chemical Company | Optimized production of aromatic dicarboxylic acids |
| US7959879B2 (en) | 2004-09-02 | 2011-06-14 | Grupo Petrotemex, S.A. De C.V. | Optimized production of aromatic dicarboxylic acids |
| US7897810B2 (en) | 2004-09-02 | 2011-03-01 | Eastman Chemical Company | Optimized production of aromatic dicarboxylic acids |
| US7291270B2 (en) | 2004-10-28 | 2007-11-06 | Eastman Chemical Company | Process for removal of impurities from an oxidizer purge stream |
| US7273559B2 (en) | 2004-10-28 | 2007-09-25 | Eastman Chemical Company | Process for removal of impurities from an oxidizer purge stream |
| US7402694B2 (en) | 2005-08-11 | 2008-07-22 | Eastman Chemical Company | Process for removal of benzoic acid from an oxidizer purge stream |
| US7569722B2 (en) | 2005-08-11 | 2009-08-04 | Eastman Chemical Company | Process for removal of benzoic acid from an oxidizer purge stream |
| WO2007021487A3 (en) * | 2005-08-11 | 2007-05-03 | Eastman Chem Co | Process for removal of benzoic acid from an oxidizer purge stream |
| US7759516B2 (en) | 2006-03-01 | 2010-07-20 | Eastman Chemical Company | Versatile oxidation byproduct purge process |
| US7897808B2 (en) | 2006-03-01 | 2011-03-01 | Eastman Chemical Company | Versatile oxidation byproduct purge process |
| US7880032B2 (en) | 2006-03-01 | 2011-02-01 | Eastman Chemical Company | Versatile oxidation byproduct purge process |
| US7902395B2 (en) | 2006-03-01 | 2011-03-08 | Eastman Chemical Company | Versatile oxidation byproduct purge process |
| US7956215B2 (en) | 2006-03-01 | 2011-06-07 | Grupo Petrotemex, S.A. De C.V. | Versatile oxidation byproduct purge process |
| US7863481B2 (en) | 2006-03-01 | 2011-01-04 | Eastman Chemical Company | Versatile oxidation byproduct purge process |
| WO2015088820A1 (en) * | 2013-12-12 | 2015-06-18 | Saudi Arabian Oil Company | Liquid phase oxidation of aromatic feedstocks with manganate recycling to produce carboxylic acids |
| US9388110B2 (en) | 2013-12-12 | 2016-07-12 | Saudi Arabian Oil Company | Liquid phase oxidation of aromatic feedstocks with manganate recycling to produce carboxylic acids |
| CN105899483A (en) * | 2013-12-12 | 2016-08-24 | 沙特阿拉伯石油公司 | Liquid phase oxidation of aromatic feedstocks with manganate recycling to produce carboxylic acids |
| CN105899483B (en) * | 2013-12-12 | 2018-02-16 | 沙特阿拉伯石油公司 | Recycled with manganate to produce the liquid phase oxidation of the aromatic raw material of carboxylic acid |
| US9902677B2 (en) | 2013-12-12 | 2018-02-27 | Saudi Arabian Oil Company | Liquid phase oxidation of aromatic feedstocks with manganate recycling to produce carboxylic acids |
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