NO309858B1 - FremgangsmÕter for regenerering eller bedring av produktiviteten til katalysatorløsninger for karbonylering ved fjerning av metalliske korrosjonsprodukter - Google Patents
FremgangsmÕter for regenerering eller bedring av produktiviteten til katalysatorløsninger for karbonylering ved fjerning av metalliske korrosjonsprodukter Download PDFInfo
- Publication number
- NO309858B1 NO309858B1 NO981887A NO981887A NO309858B1 NO 309858 B1 NO309858 B1 NO 309858B1 NO 981887 A NO981887 A NO 981887A NO 981887 A NO981887 A NO 981887A NO 309858 B1 NO309858 B1 NO 309858B1
- Authority
- NO
- Norway
- Prior art keywords
- catalyst solution
- water
- carbonylation
- catalyst
- contacting
- Prior art date
Links
- 239000003054 catalyst Substances 0.000 title claims description 115
- 238000000034 method Methods 0.000 title claims description 85
- 238000005810 carbonylation reaction Methods 0.000 title claims description 64
- 230000006315 carbonylation Effects 0.000 title claims description 53
- 238000005260 corrosion Methods 0.000 title claims description 47
- 230000007797 corrosion Effects 0.000 title claims description 47
- 230000001172 regenerating effect Effects 0.000 title description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 131
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 87
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 60
- 239000011347 resin Substances 0.000 claims description 40
- 229920005989 resin Polymers 0.000 claims description 40
- 229910052703 rhodium Inorganic materials 0.000 claims description 36
- 239000010948 rhodium Substances 0.000 claims description 36
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 36
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 35
- 239000003456 ion exchange resin Substances 0.000 claims description 28
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 28
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 23
- 239000000356 contaminant Substances 0.000 claims description 21
- HSZCZNFXUDYRKD-UHFFFAOYSA-M lithium iodide Chemical compound [Li+].[I-] HSZCZNFXUDYRKD-UHFFFAOYSA-M 0.000 claims description 20
- 239000012429 reaction media 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
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 15
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 15
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 12
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 12
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 12
- 239000003729 cation exchange resin Substances 0.000 claims description 10
- 229910052783 alkali metal Inorganic materials 0.000 claims description 8
- 150000001340 alkali metals Chemical class 0.000 claims description 8
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- -1 alkali metal salt Chemical class 0.000 claims description 7
- 229910052804 chromium Inorganic materials 0.000 claims description 7
- 239000011651 chromium Substances 0.000 claims description 7
- 239000012535 impurity Substances 0.000 claims description 7
- 230000002829 reductive effect Effects 0.000 claims description 7
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 6
- 229910052742 iron Inorganic materials 0.000 claims description 6
- 229910052744 lithium Inorganic materials 0.000 claims description 6
- XIXADJRWDQXREU-UHFFFAOYSA-M lithium acetate Chemical group [Li+].CC([O-])=O XIXADJRWDQXREU-UHFFFAOYSA-M 0.000 claims description 6
- 239000011733 molybdenum Substances 0.000 claims description 6
- 229910052750 molybdenum Inorganic materials 0.000 claims description 6
- 229910052759 nickel Inorganic materials 0.000 claims description 6
- 229910003002 lithium salt Inorganic materials 0.000 claims description 5
- 159000000002 lithium salts Chemical class 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 4
- 238000005406 washing Methods 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 238000011109 contamination Methods 0.000 claims description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 239000000047 product Substances 0.000 description 42
- 238000006243 chemical reaction Methods 0.000 description 23
- 229910052751 metal Inorganic materials 0.000 description 23
- 239000002184 metal Substances 0.000 description 23
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 19
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 15
- 238000011069 regeneration method Methods 0.000 description 14
- 230000008929 regeneration Effects 0.000 description 13
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 10
- 239000002253 acid Substances 0.000 description 9
- 229910052736 halogen Inorganic materials 0.000 description 9
- 150000002367 halogens Chemical class 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 8
- 150000001298 alcohols Chemical class 0.000 description 7
- 150000002739 metals Chemical class 0.000 description 7
- 229910001413 alkali metal ion Inorganic materials 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 238000005342 ion exchange Methods 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 150000001768 cations Chemical class 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 150000004820 halides Chemical class 0.000 description 4
- 150000004694 iodide salts Chemical class 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 229940023913 cation exchange resins Drugs 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 3
- 229940006461 iodide ion Drugs 0.000 description 3
- 239000003446 ligand Substances 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- 229910001416 lithium ion Inorganic materials 0.000 description 3
- 230000036961 partial effect Effects 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 150000003283 rhodium Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 239000013505 freshwater Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 229910052741 iridium Inorganic materials 0.000 description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 2
- 229910001507 metal halide Inorganic materials 0.000 description 2
- 150000005309 metal halides Chemical class 0.000 description 2
- 150000002892 organic cations Chemical class 0.000 description 2
- 229920001568 phenolic resin Polymers 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 229910001516 alkali metal iodide Inorganic materials 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000001502 aryl halides Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 150000001767 cationic compounds Chemical class 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910001411 inorganic cation Inorganic materials 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 229940006487 lithium cation Drugs 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910001511 metal iodide Inorganic materials 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 125000005395 methacrylic acid group Chemical class 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000011027 product recovery Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 150000003284 rhodium compounds Chemical class 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 230000002522 swelling effect Effects 0.000 description 1
- 230000002194 synthesizing effect Effects 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
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/47—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0231—Halogen-containing compounds
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/20—Carbonyls
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/40—Regeneration or reactivation
- B01J31/4015—Regeneration or reactivation of catalysts containing metals
- B01J31/4023—Regeneration or reactivation of catalysts containing metals containing iron group metals, noble metals or copper
- B01J31/4038—Regeneration or reactivation of catalysts containing metals containing iron group metals, noble metals or copper containing noble metals
- B01J31/4046—Regeneration or reactivation of catalysts containing metals containing iron group metals, noble metals or copper containing noble metals containing rhodium
-
- 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
- B01J38/00—Regeneration or reactivation of catalysts, in general
- B01J38/74—Regeneration or reactivation of catalysts, in general utilising ion-exchange
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/10—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide
- C07C51/12—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide on an oxygen-containing group in organic compounds, e.g. alcohols
-
- 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
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
- B01J2231/34—Other additions, e.g. Monsanto-type carbonylations, addition to 1,2-C=X or 1,2-C-X triplebonds, additions to 1,4-C=C-C=X or 1,4-C=-C-X triple bonds with X, e.g. O, S, NH/N
-
- 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
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/822—Rhodium
-
- 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
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/06—Halogens; Compounds thereof
- B01J27/08—Halides
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/06—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing polymers
- B01J31/08—Ion-exchange resins
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24
-
- 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)
- Chemical Kinetics & Catalysis (AREA)
- Materials Engineering (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US54960995A | 1995-10-27 | 1995-10-27 | |
| PCT/US1996/016516 WO1997015544A1 (en) | 1995-10-27 | 1996-10-16 | Process for improving productivity of a carbonylation catalyst solution by removing corrosion metals |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO981887D0 NO981887D0 (no) | 1998-04-27 |
| NO981887L NO981887L (no) | 1998-04-27 |
| NO309858B1 true NO309858B1 (no) | 2001-04-09 |
Family
ID=24193714
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO981887A NO309858B1 (no) | 1995-10-27 | 1998-04-27 | FremgangsmÕter for regenerering eller bedring av produktiviteten til katalysatorløsninger for karbonylering ved fjerning av metalliske korrosjonsprodukter |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US5731252A (hu) |
| EP (1) | EP0920407B1 (hu) |
| JP (1) | JP3955326B2 (hu) |
| KR (1) | KR100462697B1 (hu) |
| CN (1) | CN1092179C (hu) |
| AR (1) | AR004107A1 (hu) |
| AT (1) | ATE229493T1 (hu) |
| AU (1) | AU702225B2 (hu) |
| BR (1) | BR9611164A (hu) |
| CA (1) | CA2234853C (hu) |
| CZ (1) | CZ297265B6 (hu) |
| DE (1) | DE69625385T2 (hu) |
| ES (1) | ES2185809T3 (hu) |
| HU (1) | HUP9901881A3 (hu) |
| IN (1) | IN189249B (hu) |
| MY (1) | MY112995A (hu) |
| NO (1) | NO309858B1 (hu) |
| NZ (1) | NZ321758A (hu) |
| PL (1) | PL185073B1 (hu) |
| RU (1) | RU2156656C2 (hu) |
| SA (1) | SA96170479B1 (hu) |
| TR (1) | TR199800738T2 (hu) |
| TW (1) | TW419393B (hu) |
| UA (1) | UA48988C2 (hu) |
| WO (1) | WO1997015544A1 (hu) |
| YU (1) | YU49355B (hu) |
| ZA (1) | ZA968942B (hu) |
Families Citing this family (61)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0410289D0 (en) * | 2004-05-07 | 2004-06-09 | Bp Chem Int Ltd | Process |
| US7820855B2 (en) * | 2008-04-29 | 2010-10-26 | Celanese International Corporation | Method and apparatus for carbonylating methanol with acetic acid enriched flash stream |
| US7790920B2 (en) * | 2008-09-11 | 2010-09-07 | Lyondell Chemical Technology, L.P. | Preparation of acetic acid |
| US8575403B2 (en) | 2010-05-07 | 2013-11-05 | Celanese International Corporation | Hydrolysis of ethyl acetate in ethanol separation process |
| US9272970B2 (en) | 2010-07-09 | 2016-03-01 | Celanese International Corporation | Hydrogenolysis of ethyl acetate in alcohol separation processes |
| WO2012148509A1 (en) | 2011-04-26 | 2012-11-01 | Celanese International Corporation | Process for producing ethanol using a stacked bed reactor |
| US9024083B2 (en) | 2010-07-09 | 2015-05-05 | Celanese International Corporation | Process for the production of ethanol from an acetic acid feed and a recycled ethyl acetate feed |
| US8710279B2 (en) | 2010-07-09 | 2014-04-29 | Celanese International Corporation | Hydrogenolysis of ethyl acetate in alcohol separation processes |
| US8664454B2 (en) | 2010-07-09 | 2014-03-04 | Celanese International Corporation | Process for production of ethanol using a mixed feed using copper containing catalyst |
| US8378141B2 (en) | 2010-08-16 | 2013-02-19 | Celanese International Corporation | Process and system for supplying vapor from drying column to light ends column |
| US8530696B2 (en) | 2010-09-24 | 2013-09-10 | Celanese International Corporation | Pump around reactor for production of acetic acid |
| US8877963B2 (en) | 2010-09-28 | 2014-11-04 | Celanese International Corporation | Production of acetic acid with high conversion rate |
| US8394988B2 (en) | 2010-09-28 | 2013-03-12 | Celanese International Corporation | Production of acetic acid with high conversion rate |
| US8461379B2 (en) | 2010-10-12 | 2013-06-11 | Celanese International Corporation | Production of acetic acid comprising feeding at least one reactant to a recycle stream |
| US8637698B2 (en) | 2010-11-19 | 2014-01-28 | Celanese International Corporation | Production of acetic acid with an increased production rate |
| US8563773B2 (en) | 2010-12-16 | 2013-10-22 | Celanese International Corporation | Eductor-based reactor and pump around loops for production of acetic acid |
| MX2013007647A (es) | 2010-12-30 | 2013-08-01 | Celanese Int Corp | Purificacion de torrentes de productos de acido acetico. |
| US8884081B2 (en) | 2011-04-26 | 2014-11-11 | Celanese International Corporation | Integrated process for producing acetic acid and alcohol |
| US8754268B2 (en) | 2011-04-26 | 2014-06-17 | Celanese International Corporation | Process for removing water from alcohol mixtures |
| US9073816B2 (en) | 2011-04-26 | 2015-07-07 | Celanese International Corporation | Reducing ethyl acetate concentration in recycle streams for ethanol production processes |
| US8686199B2 (en) | 2011-04-26 | 2014-04-01 | Celanese International Corporation | Process for reducing the concentration of acetic acid in a crude alcohol product |
| US8592635B2 (en) | 2011-04-26 | 2013-11-26 | Celanese International Corporation | Integrated ethanol production by extracting halides from acetic acid |
| US8697908B2 (en) | 2011-05-05 | 2014-04-15 | Celanese International Corporation | Removal of amine compounds from carbonylation process stream containing corrosion metal contaminants |
| US8952196B2 (en) | 2011-05-05 | 2015-02-10 | Celanese International Corporation | Removal of aromatics from carbonylation process |
| EP3838403A1 (en) | 2011-05-13 | 2021-06-23 | Novomer, Inc. | Carbonylation catalysts and method |
| US8895786B2 (en) | 2011-08-03 | 2014-11-25 | Celanese International Corporation | Processes for increasing alcohol production |
| US9663437B2 (en) | 2011-09-13 | 2017-05-30 | Celanese International Corporation | Production of acetic acid with high conversion rate |
| US8614359B2 (en) | 2011-11-09 | 2013-12-24 | Celanese International Corporation | Integrated acid and alcohol production process |
| US8686201B2 (en) | 2011-11-09 | 2014-04-01 | Celanese International Corporation | Integrated acid and alcohol production process having flashing to recover acid production catalyst |
| JP5995995B2 (ja) | 2012-02-08 | 2016-09-21 | セラニーズ・インターナショナル・コーポレーション | 高転化率での酢酸の製造 |
| WO2015171372A1 (en) | 2014-05-05 | 2015-11-12 | Novomer, Inc. | Catalyst recycle methods |
| SG11201610058QA (en) | 2014-05-30 | 2016-12-29 | Novomer Inc | Integrated methods for chemical synthesis |
| EP3171976B1 (en) | 2014-07-25 | 2023-09-06 | Novomer, Inc. | Synthesis of metal complexes and uses thereof |
| CN106715379B (zh) | 2014-10-02 | 2020-05-19 | 国际人造丝公司 | 用于生产乙酸的方法 |
| US9302975B1 (en) | 2015-07-01 | 2016-04-05 | Celanese International Corporation | Process for flashing a reaction medium |
| MY181654A (en) | 2014-11-14 | 2020-12-31 | Celanese Int Corp | Processes for improving acetic acid yield by removing iron |
| US9260369B1 (en) | 2014-11-14 | 2016-02-16 | Celanese International Corporation | Processes for producing acetic acid product having low butyl acetate content |
| US9540302B2 (en) | 2015-04-01 | 2017-01-10 | Celanese International Corporation | Processes for producing acetic acid |
| US9487464B2 (en) | 2015-01-30 | 2016-11-08 | Celanese International Corporation | Processes for producing acetic acid |
| CN107207391B (zh) | 2015-01-30 | 2020-11-06 | 国际人造丝公司 | 生产乙酸的方法 |
| MY181742A (en) | 2015-01-30 | 2021-01-06 | Celanese Int Corp | Processes for producing acetic acid |
| US9561994B2 (en) | 2015-01-30 | 2017-02-07 | Celanese International Corporation | Processes for producing acetic acid |
| US9512056B2 (en) | 2015-02-04 | 2016-12-06 | Celanese International Corporation | Process to control HI concentration in residuum stream |
| US9505696B2 (en) | 2015-02-04 | 2016-11-29 | Celanese International Corporation | Process to control HI concentration in residuum stream |
| US10413840B2 (en) | 2015-02-04 | 2019-09-17 | Celanese International Coporation | Process to control HI concentration in residuum stream |
| EP3696161A1 (en) | 2015-02-13 | 2020-08-19 | Novomer, Inc. | Continuous carbonylation processes |
| MA41513A (fr) | 2015-02-13 | 2017-12-19 | Novomer Inc | Procédé de distillation pour la production d'acide acrylique |
| MA41514A (fr) | 2015-02-13 | 2017-12-19 | Novomer Inc | Procédés intégrés de synthèse chimique |
| MA41510A (fr) | 2015-02-13 | 2017-12-19 | Novomer Inc | Procédé de production d'acide acrylique |
| US9540303B2 (en) | 2015-04-01 | 2017-01-10 | Celanese International Corporation | Processes for producing acetic acid |
| US9382183B1 (en) | 2015-07-01 | 2016-07-05 | Celanese International Corporation | Process for flashing a reaction medium |
| US9302974B1 (en) | 2015-07-01 | 2016-04-05 | Celanese International Corporation | Process for producing acetic acid |
| MY181882A (en) | 2015-10-02 | 2021-01-12 | Celanese Int Corp | Process to produce acetic acid with recycle of water |
| US9908835B2 (en) | 2015-11-13 | 2018-03-06 | Celanese International Corporation | Processes for purifying acetic and hydrating anhydride |
| US9957216B2 (en) * | 2015-11-13 | 2018-05-01 | Celanese International Corporation | Processes for producing acetic acid |
| US10807935B2 (en) | 2018-11-02 | 2020-10-20 | Celanese International Corporation | Process for continuous acetic acid production |
| CN110078612B (zh) * | 2019-06-06 | 2021-09-07 | 上海华谊（集团）公司 | 催化剂循环液的纯化方法 |
| US20230127564A1 (en) | 2020-04-01 | 2023-04-27 | Celanese International Corporation | Processes for removing and/or reducing permanganate reducing compounds and alkyl iodides |
| MX2022015384A (es) | 2020-06-03 | 2023-01-16 | Celanese Int Corp | Proceso para la produccion de acido acetico mediante la eliminacion de compuestos reductores de permanganato. |
| WO2021247854A1 (en) | 2020-06-03 | 2021-12-09 | Celanese International Corporation | Production and purification of acetic acid |
| US20230202955A1 (en) | 2020-06-03 | 2023-06-29 | Celanese International Corporation | Removal of acetals from process streams |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3769329A (en) * | 1970-03-12 | 1973-10-30 | Monsanto Co | Production of carboxylic acids and esters |
| US4007130A (en) * | 1975-12-29 | 1977-02-08 | Monsanto Company | Catalyst regeneration method |
| US4792620A (en) * | 1983-10-14 | 1988-12-20 | Bp Chemicals Limited | Carbonylation catalysts |
| US5001259A (en) * | 1984-05-03 | 1991-03-19 | Hoechst Celanese Corporation | Methanol carbonylation process |
| CA1228867A (en) * | 1984-05-03 | 1987-11-03 | G. Paull Torrence | Methanol carbonylation process |
| US4894477A (en) * | 1986-10-14 | 1990-01-16 | Hoechst Celanese Corporation | Process for regenerating a carbonylation catalyst solution to remove corrosion metals and carbonylation of methanol to acetic acid |
| DE4034501A1 (de) * | 1990-10-30 | 1992-05-07 | Hoechst Ag | Verfahren zur entfernung metallischer korrosionsprodukte aus wasserfrei betriebenen carbonylierungsreaktionen |
| GB9305902D0 (en) * | 1993-03-22 | 1993-05-12 | Bp Chem Int Ltd | Process |
-
1996
- 1996-10-16 AU AU75169/96A patent/AU702225B2/en not_active Ceased
- 1996-10-16 CZ CZ0127998A patent/CZ297265B6/cs not_active IP Right Cessation
- 1996-10-16 NZ NZ321758A patent/NZ321758A/xx not_active IP Right Cessation
- 1996-10-16 EP EP96937688A patent/EP0920407B1/en not_active Expired - Lifetime
- 1996-10-16 ES ES96937688T patent/ES2185809T3/es not_active Expired - Lifetime
- 1996-10-16 RU RU98110138/04A patent/RU2156656C2/ru not_active IP Right Cessation
- 1996-10-16 WO PCT/US1996/016516 patent/WO1997015544A1/en active IP Right Grant
- 1996-10-16 BR BR9611164A patent/BR9611164A/pt not_active IP Right Cessation
- 1996-10-16 PL PL96326360A patent/PL185073B1/pl not_active IP Right Cessation
- 1996-10-16 TR TR1998/00738T patent/TR199800738T2/xx unknown
- 1996-10-16 UA UA98042072A patent/UA48988C2/uk unknown
- 1996-10-16 AT AT96937688T patent/ATE229493T1/de active
- 1996-10-16 KR KR10-1998-0703005A patent/KR100462697B1/ko not_active IP Right Cessation
- 1996-10-16 HU HU9901881A patent/HUP9901881A3/hu unknown
- 1996-10-16 CA CA002234853A patent/CA2234853C/en not_active Expired - Fee Related
- 1996-10-16 JP JP51665097A patent/JP3955326B2/ja not_active Expired - Lifetime
- 1996-10-16 CN CN96197834A patent/CN1092179C/zh not_active Expired - Fee Related
- 1996-10-16 IN IN1828CA1996 patent/IN189249B/en unknown
- 1996-10-16 DE DE69625385T patent/DE69625385T2/de not_active Expired - Lifetime
- 1996-10-24 ZA ZA9608942A patent/ZA968942B/xx unknown
- 1996-10-25 MY MYPI96004456A patent/MY112995A/en unknown
- 1996-10-25 YU YU56496A patent/YU49355B/sh unknown
- 1996-10-25 AR ARP960104911A patent/AR004107A1/es unknown
- 1996-10-29 TW TW085113196A patent/TW419393B/zh not_active IP Right Cessation
- 1996-12-08 SA SA96170479A patent/SA96170479B1/ar unknown
-
1997
- 1997-01-21 US US08/786,016 patent/US5731252A/en not_active Expired - Lifetime
-
1998
- 1998-04-27 NO NO981887A patent/NO309858B1/no not_active IP Right Cessation
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| NO309858B1 (no) | FremgangsmÕter for regenerering eller bedring av produktiviteten til katalysatorløsninger for karbonylering ved fjerning av metalliske korrosjonsprodukter | |
| EP0265140B1 (en) | Process for regenerating a carbonylation catalyst solution to remove corrosion metals | |
| RU2358966C2 (ru) | Способ получения уксусной кислоты | |
| KR100495554B1 (ko) | 카보닐화 공정 스트림으로부터 과망간산염 환원 화합물 및 알킬요오다이드를 제거하는 방법 | |
| EP0250189B1 (en) | Process for carbonylating alcohol to carboxylic acid, especially methanol to acetic acid | |
| NO177745B (no) | Fremgangsmåte ved fremstilling av eddiksyre ved karbonylering av metanol, dimetyleter eller metylacetat | |
| EP0487284B1 (en) | Removal of carbonyl impurities from a carbonylation process stream | |
| US20090209786A1 (en) | Control of impurities in product glacial acetic acid of rhodium-catalyzed methanol carbonylation | |
| CA2381420C (en) | Rhodium/inorganic iodide catalyst system for methanol carbonylation process with improved impurity profile | |
| JP4856629B2 (ja) | カルボニル化触媒溶液からの腐蝕金属の除去方法 | |
| RU2235087C2 (ru) | Способ получения уксусной кислоты и/или метилацетата и способ улучшения стабильности и/или предотвращения дезактивации катализатора при получении уксусной кислоты и/или метилацетата | |
| JP5096916B2 (ja) | カルボニル化プロセス流からの触媒金属および促進剤金属の除去方法 | |
| US20090187043A1 (en) | Control of impurities in product glacial acetic acid of rhodium-catalyzed methanol carbonylation | |
| US20090156859A1 (en) | Control of impurities in product glacial acetic acid of rhodium-catalyzed methanol carbonylation | |
| MXPA98003321A (en) | Procedure to improve the productivity of a catalyzing solution of carbonilation by removing corrosive metals | |
| EP1360165B1 (en) | Method for reducing eda in acetic anhydride production |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM1K | Lapsed by not paying the annual fees |