UA73622C2 - A method for the preparation of carboxylic acids by hydroxycarbonylation in the presence of palladium - Google Patents
A method for the preparation of carboxylic acids by hydroxycarbonylation in the presence of palladium Download PDFInfo
- Publication number
- UA73622C2 UA73622C2 UA2003065927A UA2003065927A UA73622C2 UA 73622 C2 UA73622 C2 UA 73622C2 UA 2003065927 A UA2003065927 A UA 2003065927A UA 2003065927 A UA2003065927 A UA 2003065927A UA 73622 C2 UA73622 C2 UA 73622C2
- Authority
- UA
- Ukraine
- Prior art keywords
- palladium
- reaction medium
- reaction
- fact
- hydrogen
- Prior art date
Links
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 title claims abstract description 151
- 229910052763 palladium Inorganic materials 0.000 title claims abstract description 76
- 238000000034 method Methods 0.000 title claims abstract description 42
- 150000001735 carboxylic acids Chemical class 0.000 title claims abstract description 10
- 238000002360 preparation method Methods 0.000 title description 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims abstract description 86
- 239000012429 reaction media Substances 0.000 claims abstract description 54
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 38
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 32
- 239000001257 hydrogen Substances 0.000 claims abstract description 32
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 30
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims abstract description 19
- 229910002091 carbon monoxide Inorganic materials 0.000 claims abstract description 19
- 239000003054 catalyst Substances 0.000 claims abstract description 18
- 230000003647 oxidation Effects 0.000 claims abstract description 12
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 12
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims description 65
- 150000001875 compounds Chemical class 0.000 claims description 34
- -1 allyl ethers Chemical class 0.000 claims description 15
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 238000000605 extraction Methods 0.000 claims description 6
- 238000000926 separation method Methods 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 5
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
- 150000001993 dienes Chemical class 0.000 claims description 4
- 239000007789 gas Substances 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 2
- 150000004808 allyl alcohols Chemical class 0.000 claims description 2
- 229910000420 cerium oxide Inorganic materials 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 claims description 2
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 claims description 2
- 229920006327 polystyrene foam Polymers 0.000 claims description 2
- 229910052814 silicon oxide Inorganic materials 0.000 claims description 2
- 229920002545 silicone oil Polymers 0.000 claims description 2
- 229910001928 zirconium oxide Inorganic materials 0.000 claims description 2
- 238000004090 dissolution Methods 0.000 claims 1
- 238000012876 topography Methods 0.000 claims 1
- YIYBQIKDCADOSF-UHFFFAOYSA-N pentenoic acid group Chemical class C(C=CCC)(=O)O YIYBQIKDCADOSF-UHFFFAOYSA-N 0.000 abstract description 8
- 150000002894 organic compounds Chemical class 0.000 abstract description 3
- 239000003610 charcoal Substances 0.000 description 33
- 239000000203 mixture Substances 0.000 description 30
- 239000011521 glass Substances 0.000 description 22
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 20
- 238000004817 gas chromatography Methods 0.000 description 17
- YIYBQIKDCADOSF-ARJAWSKDSA-N cis-pent-2-enoic acid Chemical compound CC\C=C/C(O)=O YIYBQIKDCADOSF-ARJAWSKDSA-N 0.000 description 15
- DUDKKPVINWLFBI-UHFFFAOYSA-N 1-chlorobut-1-ene Chemical class CCC=CCl DUDKKPVINWLFBI-UHFFFAOYSA-N 0.000 description 13
- 238000001914 filtration Methods 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 11
- 238000007872 degassing Methods 0.000 description 10
- 238000004128 high performance liquid chromatography Methods 0.000 description 10
- 238000011002 quantification Methods 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000004458 analytical method Methods 0.000 description 9
- 238000001816 cooling Methods 0.000 description 9
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 7
- KVUDZUPUUSUAAJ-UHFFFAOYSA-N bis(chloromethyl) carbonate Chemical compound ClCOC(=O)OCCl KVUDZUPUUSUAAJ-UHFFFAOYSA-N 0.000 description 6
- 238000004140 cleaning Methods 0.000 description 6
- YTKRILODNOEEPX-NSCUHMNNSA-N crotyl chloride Chemical compound C\C=C\CCl YTKRILODNOEEPX-NSCUHMNNSA-N 0.000 description 6
- 238000004811 liquid chromatography Methods 0.000 description 6
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 239000008896 Opium Substances 0.000 description 4
- 239000001361 adipic acid Substances 0.000 description 4
- 235000011037 adipic acid Nutrition 0.000 description 4
- 229960001027 opium Drugs 0.000 description 4
- 150000002940 palladium Chemical class 0.000 description 4
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 230000003247 decreasing effect Effects 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- YIYBQIKDCADOSF-ONEGZZNKSA-N trans-pent-2-enoic acid Chemical compound CC\C=C\C(O)=O YIYBQIKDCADOSF-ONEGZZNKSA-N 0.000 description 3
- WCASXYBKJHWFMY-NSCUHMNNSA-N 2-Buten-1-ol Chemical compound C\C=C\CO WCASXYBKJHWFMY-NSCUHMNNSA-N 0.000 description 2
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000006315 carbonylation Effects 0.000 description 2
- 238000005810 carbonylation reaction Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- GAEKPEKOJKCEMS-UHFFFAOYSA-N gamma-valerolactone Chemical compound CC1CCC(=O)O1 GAEKPEKOJKCEMS-UHFFFAOYSA-N 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- MKUWVMRNQOOSAT-UHFFFAOYSA-N methylvinylmethanol Natural products CC(O)C=C MKUWVMRNQOOSAT-UHFFFAOYSA-N 0.000 description 2
- 150000002941 palladium compounds Chemical class 0.000 description 2
- JKDRQYIYVJVOPF-FDGPNNRMSA-L palladium(ii) acetylacetonate Chemical compound [Pd+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O JKDRQYIYVJVOPF-FDGPNNRMSA-L 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- WVUYYXUATWMVIT-UHFFFAOYSA-N 1-bromo-4-ethoxybenzene Chemical compound CCOC1=CC=C(Br)C=C1 WVUYYXUATWMVIT-UHFFFAOYSA-N 0.000 description 1
- WLAMNBDJUVNPJU-BYPYZUCNSA-N 2-Methylbutanoic acid Natural products CC[C@H](C)C(O)=O WLAMNBDJUVNPJU-BYPYZUCNSA-N 0.000 description 1
- RVHOBHMAPRVOLO-UHFFFAOYSA-N 2-ethylbutanedioic acid Chemical compound CCC(C(O)=O)CC(O)=O RVHOBHMAPRVOLO-UHFFFAOYSA-N 0.000 description 1
- UIERETOOQGIECD-UHFFFAOYSA-N 2-methylbut-2-enoic acid Chemical compound CC=C(C)C(O)=O UIERETOOQGIECD-UHFFFAOYSA-N 0.000 description 1
- WLAMNBDJUVNPJU-UHFFFAOYSA-N 2-methylbutyric acid Chemical compound CCC(C)C(O)=O WLAMNBDJUVNPJU-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 101100028213 Caenorhabditis elegans osm-3 gene Proteins 0.000 description 1
- 241000499489 Castor canadensis Species 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 235000011779 Menyanthes trifoliata Nutrition 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 229920002302 Nylon 6,6 Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- YNHIGQDRGKUECZ-UHFFFAOYSA-N dichloropalladium;triphenylphosphanium Chemical compound Cl[Pd]Cl.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 235000001159 dosh Nutrition 0.000 description 1
- 244000245171 dosh Species 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000008241 heterogeneous mixture Substances 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 125000005358 mercaptoalkyl group Chemical group 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- HVAMZGADVCBITI-UHFFFAOYSA-N pent-4-enoic acid Chemical compound OC(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-N 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 239000010970 precious metal Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/10—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide
- C07C51/14—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide on a carbon-to-carbon unsaturated bond in organic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0017101A FR2818638B1 (fr) | 2000-12-27 | 2000-12-27 | Procede de preparation d'acides carboxyliques par carbonylation au palladium |
| PCT/FR2001/004149 WO2002051783A1 (fr) | 2000-12-27 | 2001-12-21 | Procede de preparation d'acides carboxyliques par carbonylation au palladium. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA73622C2 true UA73622C2 (en) | 2005-08-15 |
Family
ID=8858258
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA2003065927A UA73622C2 (en) | 2000-12-27 | 2001-12-21 | A method for the preparation of carboxylic acids by hydroxycarbonylation in the presence of palladium |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US6946574B2 (de) |
| EP (1) | EP1345880B1 (de) |
| JP (1) | JP3906154B2 (de) |
| KR (1) | KR100523721B1 (de) |
| CN (1) | CN1220668C (de) |
| AR (1) | AR032061A1 (de) |
| AT (1) | ATE289288T1 (de) |
| BR (1) | BR0116755A (de) |
| CA (1) | CA2433300A1 (de) |
| DE (1) | DE60108979T2 (de) |
| ES (1) | ES2233715T3 (de) |
| FR (1) | FR2818638B1 (de) |
| HU (1) | HUP0600058A3 (de) |
| IL (1) | IL156598A0 (de) |
| MX (1) | MXPA03005794A (de) |
| PL (1) | PL363484A1 (de) |
| RU (1) | RU2240306C1 (de) |
| TW (1) | TWI227230B (de) |
| UA (1) | UA73622C2 (de) |
| WO (1) | WO2002051783A1 (de) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004096747A1 (en) * | 2003-04-28 | 2004-11-11 | Basf Aktiengesellschaft | Process for the separation of palladium catalyst from crude reaction mixtures of aryl acetic acids obtained by carbonylation |
| US20080269520A1 (en) * | 2005-02-11 | 2008-10-30 | Eit Drent | Process for the Carbonylation of a Conjugated Diene to a Dicarboxylic Acid |
| TW200633971A (en) * | 2005-02-11 | 2006-10-01 | Shell Int Research | Process for the carbonylation of a conjugated diene |
| TW200633970A (en) * | 2005-02-11 | 2006-10-01 | Shell Int Research | Process for the preparation of a dicarboxylic acid |
| US20080194870A1 (en) * | 2005-02-11 | 2008-08-14 | Eit Drent | Process for the Preparation of a Dicarboxylic Acid |
| JP5240750B2 (ja) * | 2007-04-11 | 2013-07-17 | 東ソー有機化学株式会社 | パラジウムの除去方法 |
| EP2849884B1 (de) * | 2012-05-15 | 2020-09-09 | Archer-Daniels-Midland Company | Reduktionskatalysatoren |
| JP2018100221A (ja) * | 2015-04-17 | 2018-06-28 | アステラス製薬株式会社 | Ｐｄを実質的に含まない有機化合物の製造方法及び水素ガスを用いた有機化合物からＰｄを除去する新規な方法 |
| CN107337572A (zh) * | 2017-05-31 | 2017-11-10 | 中国科学技术大学 | 一种制备β,γ‑不饱和羧酸类化合物的方法 |
| EP4011893A1 (de) * | 2020-12-09 | 2022-06-15 | Evonik Operations GmbH | Platin-komplexe mit binaphthyl basiertem diphosphinliganden für die selektive katalyse der hydroxycarbonylierung ethylenisch ungesättigter verbindungen |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB655339A (en) * | 1948-10-27 | 1951-07-18 | Arthur William Charles Taylor | Improvements in and relating to the production of oxygencontaining compounds |
| US3509209A (en) * | 1967-01-12 | 1970-04-28 | Union Oil Co | Hydrocarboxylation of certain conjugated diolefin compounds |
| DE2833469C2 (de) * | 1978-07-29 | 1986-10-09 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Aufarbeitung von Reaktionsgemischen, die bei der Hydroformylierung oder der Carbonylierung anfallen |
| FR2529885A1 (fr) * | 1982-07-09 | 1984-01-13 | Rhone Poulenc Chim Base | Procede de preparation d'acides carboxyliques b,g-insatures |
| FR2711365B1 (fr) * | 1993-10-19 | 1995-12-15 | Rhone Poulenc Chimie | Procédé d'hydroxycarbonylation du butadiène. |
| US5981788A (en) * | 1997-11-03 | 1999-11-09 | General Electric Company | Method for recovering and recycling catalyst constituents |
-
2000
- 2000-12-27 FR FR0017101A patent/FR2818638B1/fr not_active Expired - Fee Related
-
2001
- 2001-12-21 KR KR10-2003-7008766A patent/KR100523721B1/ko not_active IP Right Cessation
- 2001-12-21 PL PL01363484A patent/PL363484A1/xx unknown
- 2001-12-21 IL IL15659801A patent/IL156598A0/xx unknown
- 2001-12-21 UA UA2003065927A patent/UA73622C2/uk unknown
- 2001-12-21 WO PCT/FR2001/004149 patent/WO2002051783A1/fr active IP Right Grant
- 2001-12-21 ES ES01995752T patent/ES2233715T3/es not_active Expired - Lifetime
- 2001-12-21 US US10/451,662 patent/US6946574B2/en not_active Expired - Fee Related
- 2001-12-21 HU HU0600058A patent/HUP0600058A3/hu unknown
- 2001-12-21 CA CA002433300A patent/CA2433300A1/fr not_active Abandoned
- 2001-12-21 MX MXPA03005794A patent/MXPA03005794A/es not_active Application Discontinuation
- 2001-12-21 AT AT01995752T patent/ATE289288T1/de not_active IP Right Cessation
- 2001-12-21 CN CNB018221971A patent/CN1220668C/zh not_active Expired - Fee Related
- 2001-12-21 BR BR0116755-3A patent/BR0116755A/pt active Search and Examination
- 2001-12-21 EP EP01995752A patent/EP1345880B1/de not_active Expired - Lifetime
- 2001-12-21 DE DE60108979T patent/DE60108979T2/de not_active Expired - Fee Related
- 2001-12-21 TW TW090131873A patent/TWI227230B/zh not_active IP Right Cessation
- 2001-12-21 RU RU2003123117/04A patent/RU2240306C1/ru not_active IP Right Cessation
- 2001-12-21 JP JP2002552884A patent/JP3906154B2/ja not_active Expired - Fee Related
- 2001-12-27 AR ARP010106048A patent/AR032061A1/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CN1487913A (zh) | 2004-04-07 |
| FR2818638B1 (fr) | 2003-02-07 |
| CN1220668C (zh) | 2005-09-28 |
| CA2433300A1 (fr) | 2002-07-04 |
| JP2004520322A (ja) | 2004-07-08 |
| ATE289288T1 (de) | 2005-03-15 |
| HUP0600058A3 (en) | 2007-08-28 |
| US6946574B2 (en) | 2005-09-20 |
| RU2240306C1 (ru) | 2004-11-20 |
| EP1345880A1 (de) | 2003-09-24 |
| DE60108979D1 (de) | 2005-03-24 |
| JP3906154B2 (ja) | 2007-04-18 |
| IL156598A0 (en) | 2004-01-04 |
| KR20030066776A (ko) | 2003-08-09 |
| BR0116755A (pt) | 2004-01-13 |
| FR2818638A1 (fr) | 2002-06-28 |
| AR032061A1 (es) | 2003-10-22 |
| WO2002051783A1 (fr) | 2002-07-04 |
| HUP0600058A2 (en) | 2007-01-29 |
| US20040068142A1 (en) | 2004-04-08 |
| TWI227230B (en) | 2005-02-01 |
| RU2003123117A (ru) | 2005-02-20 |
| DE60108979T2 (de) | 2005-07-14 |
| KR100523721B1 (ko) | 2005-10-26 |
| PL363484A1 (en) | 2004-11-15 |
| MXPA03005794A (es) | 2003-09-10 |
| ES2233715T3 (es) | 2005-06-16 |
| EP1345880B1 (de) | 2005-02-16 |
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