CA2273958A1 - Production d'acides carboxyliques aromatiques - Google Patents
Production d'acides carboxyliques aromatiques Download PDFInfo
- Publication number
- CA2273958A1 CA2273958A1 CA002273958A CA2273958A CA2273958A1 CA 2273958 A1 CA2273958 A1 CA 2273958A1 CA 002273958 A CA002273958 A CA 002273958A CA 2273958 A CA2273958 A CA 2273958A CA 2273958 A1 CA2273958 A1 CA 2273958A1
- Authority
- CA
- Canada
- Prior art keywords
- acid
- water
- stream
- monocarboxylic acid
- bromine
- 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.)
- Abandoned
Links
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 26
- -1 aromatic carboxylic acids Chemical class 0.000 title claims abstract description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 96
- 229910001868 water Inorganic materials 0.000 claims abstract description 96
- 239000007789 gas Substances 0.000 claims abstract description 91
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 claims abstract description 56
- 238000002485 combustion reaction Methods 0.000 claims abstract description 54
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 51
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims abstract description 42
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims abstract description 39
- 230000003647 oxidation Effects 0.000 claims abstract description 37
- 229940102396 methyl bromide Drugs 0.000 claims abstract description 28
- 239000003054 catalyst Substances 0.000 claims abstract description 25
- 238000006243 chemical reaction Methods 0.000 claims abstract description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 18
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000001301 oxygen Substances 0.000 claims abstract description 16
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 16
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims abstract description 14
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229910002091 carbon monoxide Inorganic materials 0.000 claims abstract description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 8
- 239000001569 carbon dioxide Substances 0.000 claims abstract description 7
- 229910002092 carbon dioxide Inorganic materials 0.000 claims abstract description 7
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 90
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 81
- 238000000034 method Methods 0.000 claims description 56
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 claims description 54
- 229910052794 bromium Inorganic materials 0.000 claims description 49
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims description 45
- 238000000926 separation method Methods 0.000 claims description 40
- 239000012452 mother liquor Substances 0.000 claims description 39
- 238000005201 scrubbing Methods 0.000 claims description 39
- 238000011084 recovery Methods 0.000 claims description 38
- 239000002253 acid Substances 0.000 claims description 30
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 24
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 21
- 238000000746 purification Methods 0.000 claims description 20
- 239000002243 precursor Substances 0.000 claims description 17
- 238000005406 washing Methods 0.000 claims description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- 238000004821 distillation Methods 0.000 claims description 15
- 239000007791 liquid phase Substances 0.000 claims description 14
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 14
- 239000002002 slurry Substances 0.000 claims description 14
- 238000012545 processing Methods 0.000 claims description 12
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 claims description 12
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 10
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 8
- 239000006227 byproduct Substances 0.000 claims description 8
- 238000010992 reflux Methods 0.000 claims description 8
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 claims description 8
- 238000009833 condensation Methods 0.000 claims description 7
- 230000005494 condensation Effects 0.000 claims description 7
- 150000002894 organic compounds Chemical class 0.000 claims description 7
- 238000011144 upstream manufacturing Methods 0.000 claims description 7
- 239000013078 crystal Substances 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000012535 impurity Substances 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 235000010265 sodium sulphite Nutrition 0.000 claims description 6
- 229910001385 heavy metal Inorganic materials 0.000 claims description 5
- 239000012071 phase Substances 0.000 claims description 5
- 239000004280 Sodium formate Substances 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 239000001273 butane Substances 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 4
- 239000001294 propane Substances 0.000 claims description 4
- 239000012429 reaction media Substances 0.000 claims description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 4
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 claims description 4
- 235000019254 sodium formate Nutrition 0.000 claims description 4
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 3
- 239000004202 carbamide Substances 0.000 claims description 3
- 239000012065 filter cake Substances 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 2
- 235000013877 carbamide Nutrition 0.000 claims description 2
- 239000003345 natural gas Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
- 229910001882 dioxygen Inorganic materials 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 2
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 abstract 2
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 54
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 18
- 239000007788 liquid Substances 0.000 description 18
- 239000000047 product Substances 0.000 description 11
- 238000007084 catalytic combustion reaction Methods 0.000 description 8
- 235000011121 sodium hydroxide Nutrition 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 6
- 230000007797 corrosion Effects 0.000 description 6
- 238000005260 corrosion Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 4
- 239000000446 fuel Substances 0.000 description 4
- 238000005984 hydrogenation reaction Methods 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
- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 description 4
- 238000010926 purge Methods 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 3
- 239000007806 chemical reaction intermediate Substances 0.000 description 3
- 239000010941 cobalt Substances 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 235000017550 sodium carbonate Nutrition 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- YGYNBBAUIYTWBF-UHFFFAOYSA-N 2,6-dimethylnaphthalene Chemical compound C1=C(C)C=CC2=CC(C)=CC=C21 YGYNBBAUIYTWBF-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000010304 firing Methods 0.000 description 2
- 239000007792 gaseous phase Substances 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 235000011118 potassium hydroxide Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- UBAZGMLMVVQSCD-UHFFFAOYSA-N carbon dioxide;molecular oxygen Chemical compound O=O.O=C=O UBAZGMLMVVQSCD-UHFFFAOYSA-N 0.000 description 1
- 229910002090 carbon oxide Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 229910021446 cobalt carbonate Inorganic materials 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- 235000003642 hunger Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 239000011656 manganese carbonate Substances 0.000 description 1
- 235000006748 manganese carbonate Nutrition 0.000 description 1
- 229940093474 manganese carbonate Drugs 0.000 description 1
- 150000002697 manganese compounds Chemical class 0.000 description 1
- 229910000016 manganese(II) carbonate Inorganic materials 0.000 description 1
- XMWCXZJXESXBBY-UHFFFAOYSA-L manganese(ii) carbonate Chemical compound [Mn+2].[O-]C([O-])=O XMWCXZJXESXBBY-UHFFFAOYSA-L 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- RXOHFPCZGPKIRD-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 RXOHFPCZGPKIRD-UHFFFAOYSA-N 0.000 description 1
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000011514 reflex Effects 0.000 description 1
- 238000003303 reheating Methods 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 230000037351 starvation Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F23—COMBUSTION APPARATUS; COMBUSTION PROCESSES
- F23G—CREMATION FURNACES; CONSUMING WASTE PRODUCTS BY COMBUSTION
- F23G7/00—Incinerators or other apparatus for consuming industrial waste, e.g. chemicals
- F23G7/06—Incinerators or other apparatus for consuming industrial waste, e.g. chemicals of waste gases or noxious gases, e.g. exhaust gases
- F23G7/07—Incinerators or other apparatus for consuming industrial waste, e.g. chemicals of waste gases or noxious gases, e.g. exhaust gases in which combustion takes place in the presence of catalytic material
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
- B01D53/34—Chemical or biological purification of waste gases
- B01D53/74—General processes for purification of waste gases; Apparatus or devices specially adapted therefor
- B01D53/86—Catalytic processes
- B01D53/8659—Removing halogens or halogen compounds
- B01D53/8662—Organic halogen compounds
-
- 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
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F23—COMBUSTION APPARATUS; COMBUSTION PROCESSES
- F23G—CREMATION FURNACES; CONSUMING WASTE PRODUCTS BY COMBUSTION
- F23G2209/00—Specific waste
- F23G2209/14—Gaseous waste or fumes
- F23G2209/142—Halogen gases, e.g. silane
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F23—COMBUSTION APPARATUS; COMBUSTION PROCESSES
- F23J—REMOVAL OR TREATMENT OF COMBUSTION PRODUCTS OR COMBUSTION RESIDUES; FLUES
- F23J2215/00—Preventing emissions
- F23J2215/30—Halogen; Compounds thereof
-
- 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
Landscapes
- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Environmental & Geological Engineering (AREA)
- Organic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Health & Medical Sciences (AREA)
- Biomedical Technology (AREA)
- Analytical Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
On traite un effluent gazeux contenant des constituants organiques dont un acide carboxylique aliphatique et du bromure de méthyle, des gaz dont l'azote, l'oxygène, le monoxyde et le dioxyde de carbone et de l'eau, en particulier quand ce gaz provient de la production d'un acide carboxylique aromatique tel que l'acide téréphtalique, dans le but d'éliminer sensiblement tout l'acide carboxylique aliphatique qu'il contient, et on lui fait subir ensuite une combustion à haute température, éventuellement en présence d'un catalyseur d'oxydation ou d'un auxiliaire de combustion, ou des deux, pour effectuer la conversion complète du bromure de méthyle qu'il contient en HBr ou Br¿2?, ou les deux. Le courant de gaz ainsi obtenu est transmis à un appareil de conversion d'énergie tel qu'une turbine à gaz, après quoi il est épuré pour éliminer le HBr ou le Br¿2?, ou les deux.
Applications Claiming Priority (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9601493.1 | 1996-01-25 | ||
| GBGB9601493.1A GB9601493D0 (en) | 1996-01-25 | 1996-01-25 | Effluent gas treatment |
| GB9602050.8 | 1996-02-01 | ||
| GBGB9602050.8A GB9602050D0 (en) | 1996-02-01 | 1996-02-01 | Effluent gas treatment |
| GB9602458.3 | 1996-02-07 | ||
| GBGB9602458.3A GB9602458D0 (en) | 1996-02-07 | 1996-02-07 | Effluent gas treatment |
| GBPCT/GB96/01261 | 1996-05-28 | ||
| PCT/GB1996/001261 WO1996039595A1 (fr) | 1995-06-05 | 1996-05-28 | Traitement de gaz d'effluent |
| GBGB9620494.6A GB9620494D0 (en) | 1996-10-02 | 1996-10-02 | Production of aromatic carboxylic acids |
| GB9620494.6 | 1996-10-02 | ||
| US2778496P | 1996-10-04 | 1996-10-04 | |
| US60/027,784 | 1996-10-04 | ||
| PCT/GB1997/000104 WO1997027168A1 (fr) | 1996-01-25 | 1997-01-15 | Production d'acides carboxyliques aromatiques |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2273958A1 true CA2273958A1 (fr) | 1997-07-31 |
Family
ID=27547254
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002273958A Abandoned CA2273958A1 (fr) | 1996-01-25 | 1997-01-15 | Production d'acides carboxyliques aromatiques |
Country Status (3)
| Country | Link |
|---|---|
| EP (1) | EP0879221A1 (fr) |
| CA (1) | CA2273958A1 (fr) |
| WO (1) | WO1997027168A1 (fr) |
Families Citing this family (50)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20000005733A (ko) * | 1998-06-05 | 2000-01-25 | 나까니시 히로유끼 | 방향족카복실산의제조방법 |
| US6504051B1 (en) * | 2001-06-04 | 2003-01-07 | Eastman Chemical Company | Process for production of aromatic carboxylic acids with improved water removal technique |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| US7541489B2 (en) | 2004-06-30 | 2009-06-02 | Sabic Innovative Plastics Ip B.V. | Method of making halophthalic acids and halophthalic anhydrides |
| US7608732B2 (en) | 2005-03-08 | 2009-10-27 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7888530B2 (en) | 2004-09-02 | 2011-02-15 | Eastman Chemical Company | Optimized production of aromatic dicarboxylic acids |
| US7507857B2 (en) | 2004-09-02 | 2009-03-24 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7608733B2 (en) | 2004-09-02 | 2009-10-27 | Eastman Chemical Company | Optimized liquid-phase oxidation |
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| US9505692B2 (en) * | 2008-10-31 | 2016-11-29 | Grupo Petrotemex, S.A. De C.V. | Dicarboxylic acid production with self-fuel oxidative destruction |
| US20100113735A1 (en) | 2008-10-31 | 2010-05-06 | Eastman Chemical Company | Integrated Co-Production of Dicarboxylic Acids |
| US9493387B2 (en) | 2008-10-31 | 2016-11-15 | Grupo Petrotemex, S.A. De C.V. | Dicarboxylic acid production with minimal wastewater generation |
| US9493389B2 (en) * | 2008-10-31 | 2016-11-15 | Grupo Petrotemex, S.A. De C.V. | Dicarboxylic acid production with enhanced energy recovery |
| US9493388B2 (en) * | 2008-10-31 | 2016-11-15 | Grupo Petrotemex, S.A. De C.V. | Dicarboxylic acid production with direct fired off-gas heating |
| CN101940869B (zh) * | 2010-06-13 | 2013-08-07 | 浙江逸盛石化有限公司 | 精对苯二甲酸氧化装置尾气的净化方法和装置 |
| CN105829277B (zh) | 2013-12-18 | 2020-01-17 | Bp北美公司 | 制造芳族羧酸的改进的工艺和设备 |
| GB201417703D0 (en) * | 2014-10-07 | 2014-11-19 | Invista Technologies S.�.R.L. | Production of an aromatic dicarboxylic acid |
| TWI690496B (zh) * | 2019-02-01 | 2020-04-11 | 兆聯實業股份有限公司 | 水處理系統 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0013100B1 (fr) * | 1978-12-21 | 1982-05-19 | Imperial Chemical Industries Plc | Récupération du brome des gaz effluents de l'oxydation catalytique à l'aide de brome |
| GB9400570D0 (en) * | 1994-01-13 | 1994-03-09 | Ici Plc | Handling of materials at elevated pressure |
| US5612007A (en) * | 1994-10-14 | 1997-03-18 | Amoco Corporation | Apparatus for preparing aromatic carboxylic acids with efficient energy recovery |
-
1997
- 1997-01-15 CA CA002273958A patent/CA2273958A1/fr not_active Abandoned
- 1997-01-15 WO PCT/GB1997/000104 patent/WO1997027168A1/fr not_active Ceased
- 1997-01-15 EP EP97900351A patent/EP0879221A1/fr not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| WO1997027168A1 (fr) | 1997-07-31 |
| EP0879221A1 (fr) | 1998-11-25 |
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