JP5091142B2 - 有機遷移金属錯体触媒を分離する方法 - Google Patents
有機遷移金属錯体触媒を分離する方法 Download PDFInfo
- Publication number
- JP5091142B2 JP5091142B2 JP2008532709A JP2008532709A JP5091142B2 JP 5091142 B2 JP5091142 B2 JP 5091142B2 JP 2008532709 A JP2008532709 A JP 2008532709A JP 2008532709 A JP2008532709 A JP 2008532709A JP 5091142 B2 JP5091142 B2 JP 5091142B2
- Authority
- JP
- Japan
- Prior art keywords
- membrane
- hydroformylation
- separation step
- pressure
- reaction mixture
- 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.)
- Active
Links
- 239000003054 catalyst Substances 0.000 title claims abstract description 94
- 238000000034 method Methods 0.000 title claims description 112
- 150000004696 coordination complex Chemical class 0.000 title claims description 7
- 239000012528 membrane Substances 0.000 claims abstract description 181
- 238000000926 separation method Methods 0.000 claims abstract description 114
- 239000003446 ligand Substances 0.000 claims abstract description 80
- 239000012466 permeate Substances 0.000 claims abstract description 68
- 239000011541 reaction mixture Substances 0.000 claims abstract description 57
- 239000000047 product Substances 0.000 claims abstract description 41
- 229910052751 metal Inorganic materials 0.000 claims abstract description 25
- 239000002184 metal Substances 0.000 claims abstract description 25
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims abstract description 22
- 239000003960 organic solvent Substances 0.000 claims abstract description 4
- 238000007037 hydroformylation reaction Methods 0.000 claims description 112
- 239000010948 rhodium Substances 0.000 claims description 40
- 239000012465 retentate Substances 0.000 claims description 36
- 229910052703 rhodium Inorganic materials 0.000 claims description 35
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 34
- -1 dissolved Substances 0.000 claims description 19
- 239000002904 solvent Substances 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 239000000126 substance Substances 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- 239000004696 Poly ether ether ketone Substances 0.000 claims description 7
- 239000004205 dimethyl polysiloxane Substances 0.000 claims description 7
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 claims description 7
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 claims description 7
- 229920002530 polyetherether ketone Polymers 0.000 claims description 7
- 239000004642 Polyimide Substances 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 238000007872 degassing Methods 0.000 claims description 6
- 230000014759 maintenance of location Effects 0.000 claims description 6
- 229920001721 polyimide Polymers 0.000 claims description 6
- 229920000642 polymer Polymers 0.000 claims description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 5
- 239000004952 Polyamide Substances 0.000 claims description 5
- 229920002647 polyamide Polymers 0.000 claims description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 4
- 239000000919 ceramic Substances 0.000 claims description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 4
- 229920002312 polyamide-imide Polymers 0.000 claims description 4
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 3
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 3
- 229910017052 cobalt Inorganic materials 0.000 claims description 3
- 239000010941 cobalt Substances 0.000 claims description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 3
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 claims description 3
- 229910052741 iridium Inorganic materials 0.000 claims description 3
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052762 osmium Inorganic materials 0.000 claims description 3
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims description 3
- 229910052707 ruthenium Inorganic materials 0.000 claims description 3
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 2
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 2
- 229910052804 chromium Inorganic materials 0.000 claims description 2
- 239000011651 chromium Substances 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- 229910052750 molybdenum Inorganic materials 0.000 claims description 2
- 239000011733 molybdenum Substances 0.000 claims description 2
- 229910052759 nickel Inorganic materials 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- 125000006850 spacer group Chemical group 0.000 claims description 2
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims description 2
- 229910052721 tungsten Inorganic materials 0.000 claims description 2
- 239000010937 tungsten Substances 0.000 claims description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 3
- 238000004804 winding Methods 0.000 claims 1
- 229910002091 carbon monoxide Inorganic materials 0.000 abstract description 21
- 210000004379 membrane Anatomy 0.000 description 146
- 238000006243 chemical reaction Methods 0.000 description 36
- 239000007789 gas Substances 0.000 description 35
- 238000001728 nano-filtration Methods 0.000 description 29
- 239000000203 mixture Substances 0.000 description 24
- 230000015572 biosynthetic process Effects 0.000 description 23
- 238000003786 synthesis reaction Methods 0.000 description 23
- 150000001336 alkenes Chemical class 0.000 description 16
- 239000010408 film Substances 0.000 description 16
- 239000007858 starting material Substances 0.000 description 14
- 239000007795 chemical reaction product Substances 0.000 description 13
- 229910052739 hydrogen Inorganic materials 0.000 description 12
- 150000001299 aldehydes Chemical class 0.000 description 10
- 125000001931 aliphatic group Chemical group 0.000 description 10
- 125000003118 aryl group Chemical group 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 10
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 10
- 230000000694 effects Effects 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 230000003197 catalytic effect Effects 0.000 description 8
- 239000007791 liquid phase Substances 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 7
- 125000001072 heteroaryl group Chemical group 0.000 description 7
- 229930195733 hydrocarbon Natural products 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- 229910052698 phosphorus Inorganic materials 0.000 description 7
- 239000011574 phosphorus Substances 0.000 description 7
- 230000000717 retained effect Effects 0.000 description 7
- OUFCBJZGDJFSIK-UHFFFAOYSA-N 11-methyldodecanal Chemical compound CC(C)CCCCCCCCCC=O OUFCBJZGDJFSIK-UHFFFAOYSA-N 0.000 description 6
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000004215 Carbon black (E152) Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- JKIJEFPNVSHHEI-UHFFFAOYSA-N Phenol, 2,4-bis(1,1-dimethylethyl)-, phosphite (3:1) Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C JKIJEFPNVSHHEI-UHFFFAOYSA-N 0.000 description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 5
- 125000002723 alicyclic group Chemical group 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 125000000623 heterocyclic group Chemical group 0.000 description 5
- 125000005538 phosphinite group Chemical group 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 150000003573 thiols Chemical class 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 230000000737 periodic effect Effects 0.000 description 4
- 229910052723 transition metal Inorganic materials 0.000 description 4
- 150000003624 transition metals Chemical class 0.000 description 4
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 230000008021 deposition Effects 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- IHDGDXHKTFMWSW-UHFFFAOYSA-K nonanoate;rhodium(3+) Chemical compound [Rh+3].CCCCCCCCC([O-])=O.CCCCCCCCC([O-])=O.CCCCCCCCC([O-])=O IHDGDXHKTFMWSW-UHFFFAOYSA-K 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical class OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 description 3
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 230000000087 stabilizing effect Effects 0.000 description 3
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- 239000004962 Polyamide-imide Substances 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 238000001479 atomic absorption spectroscopy Methods 0.000 description 2
- 238000001636 atomic emission spectroscopy Methods 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 150000003283 rhodium Chemical class 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 150000003566 thiocarboxylic acids Chemical class 0.000 description 2
- XTTGYFREQJCEML-UHFFFAOYSA-N tributyl phosphite Chemical compound CCCCOP(OCCCC)OCCCC XTTGYFREQJCEML-UHFFFAOYSA-N 0.000 description 2
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 2
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- KQVTYYDZPZYVIB-UHFFFAOYSA-N 4,5-dihydrooxaphosphole Chemical compound C1CC=PO1 KQVTYYDZPZYVIB-UHFFFAOYSA-N 0.000 description 1
- GNETVOUSGGAEDK-UHFFFAOYSA-N 4-bis[4-(dimethylamino)phenyl]phosphanyl-n,n-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1P(C=1C=CC(=CC=1)N(C)C)C1=CC=C(N(C)C)C=C1 GNETVOUSGGAEDK-UHFFFAOYSA-N 0.000 description 1
- 229920002284 Cellulose triacetate Polymers 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- BONASJKBJAQWML-UHFFFAOYSA-N OPO.OP(O)O Chemical compound OPO.OP(O)O BONASJKBJAQWML-UHFFFAOYSA-N 0.000 description 1
- BOBIVTKCBMKFJH-UHFFFAOYSA-N P.P(O)O Chemical compound P.P(O)O BOBIVTKCBMKFJH-UHFFFAOYSA-N 0.000 description 1
- GYPUIXZFFQOUPO-UHFFFAOYSA-N PO.OPO Chemical compound PO.OPO GYPUIXZFFQOUPO-UHFFFAOYSA-N 0.000 description 1
- QFIJGEIKVGDVHA-UHFFFAOYSA-N PO.P(O)(O)O Chemical compound PO.P(O)(O)O QFIJGEIKVGDVHA-UHFFFAOYSA-N 0.000 description 1
- 239000002033 PVDF binder Substances 0.000 description 1
- 239000004693 Polybenzimidazole Substances 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 1
- FJWGYAHXMCUOOM-QHOUIDNNSA-N [(2s,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6s)-4,5-dinitrooxy-2-(nitrooxymethyl)-6-[(2r,3r,4s,5r,6s)-4,5,6-trinitrooxy-2-(nitrooxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-3,5-dinitrooxy-6-(nitrooxymethyl)oxan-4-yl] nitrate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O)O[C@H]1[C@@H]([C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@@H](CO[N+]([O-])=O)O1)O[N+]([O-])=O)CO[N+](=O)[O-])[C@@H]1[C@@H](CO[N+]([O-])=O)O[C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O FJWGYAHXMCUOOM-QHOUIDNNSA-N 0.000 description 1
- 125000005595 acetylacetonate group Chemical group 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 150000007824 aliphatic compounds Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000004760 aramid Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical group 0.000 description 1
- 229920003235 aromatic polyamide Polymers 0.000 description 1
- YSZKOFNTXPLTCU-UHFFFAOYSA-N barium lithium Chemical compound [Li].[Ba] YSZKOFNTXPLTCU-UHFFFAOYSA-N 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000001934 delay Effects 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- NSSMTQDEWVTEKN-UHFFFAOYSA-N diethoxy(methyl)phosphane Chemical compound CCOP(C)OCC NSSMTQDEWVTEKN-UHFFFAOYSA-N 0.000 description 1
- LMZLQYYLELWCCW-UHFFFAOYSA-N dimethoxy(phenyl)phosphane Chemical compound COP(OC)C1=CC=CC=C1 LMZLQYYLELWCCW-UHFFFAOYSA-N 0.000 description 1
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 1
- QXKPLZDCTKREIA-UHFFFAOYSA-N diphenoxy(phenyl)phosphane Chemical compound C=1C=CC=CC=1OP(C=1C=CC=CC=1)OC1=CC=CC=C1 QXKPLZDCTKREIA-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- JCRCPEDXAHDCAJ-UHFFFAOYSA-N ethoxy(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(OCC)C1=CC=CC=C1 JCRCPEDXAHDCAJ-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000011552 falling film Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000004868 gas analysis Methods 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002390 heteroarenes Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000012784 inorganic fiber Substances 0.000 description 1
- 229910052809 inorganic oxide Inorganic materials 0.000 description 1
- BAZQYVYVKYOAGO-UHFFFAOYSA-M loxoprofen sodium hydrate Chemical compound O.O.[Na+].C1=CC(C(C([O-])=O)C)=CC=C1CC1C(=O)CCC1 BAZQYVYVKYOAGO-UHFFFAOYSA-M 0.000 description 1
- OAADXJFIBNEPLY-UHFFFAOYSA-N methoxy(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(OC)C1=CC=CC=C1 OAADXJFIBNEPLY-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000001471 micro-filtration Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- HDKCVDHYIIKWFM-UHFFFAOYSA-K octanoate;rhodium(3+) Chemical compound [Rh+3].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O.CCCCCCCC([O-])=O HDKCVDHYIIKWFM-UHFFFAOYSA-K 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- UPDNYUVJHQABBS-UHFFFAOYSA-N phenoxy(diphenyl)phosphane Chemical compound C=1C=CC=CC=1OP(C=1C=CC=CC=1)C1=CC=CC=C1 UPDNYUVJHQABBS-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- LNUBYTUNCMSQRF-UHFFFAOYSA-N phosphane phosphinous acid Chemical compound P.PO LNUBYTUNCMSQRF-UHFFFAOYSA-N 0.000 description 1
- ZOGYOOUMDVKYLM-UHFFFAOYSA-N phosphane phosphorous acid Chemical compound P.OP(O)O ZOGYOOUMDVKYLM-UHFFFAOYSA-N 0.000 description 1
- WJIBZZVTNMAURL-UHFFFAOYSA-N phosphane;rhodium Chemical class P.[Rh] WJIBZZVTNMAURL-UHFFFAOYSA-N 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 229920000110 poly(aryl ether sulfone) Polymers 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920002480 polybenzimidazole Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 150000003284 rhodium compounds Chemical class 0.000 description 1
- SVOOVMQUISJERI-UHFFFAOYSA-K rhodium(3+);triacetate Chemical compound [Rh+3].CC([O-])=O.CC([O-])=O.CC([O-])=O SVOOVMQUISJERI-UHFFFAOYSA-K 0.000 description 1
- VXNYVYJABGOSBX-UHFFFAOYSA-N rhodium(3+);trinitrate Chemical compound [Rh+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O VXNYVYJABGOSBX-UHFFFAOYSA-N 0.000 description 1
- SONJTKJMTWTJCT-UHFFFAOYSA-K rhodium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Rh+3] SONJTKJMTWTJCT-UHFFFAOYSA-K 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000004354 sulfur functional group Chemical group 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- IFXORIIYQORRMJ-UHFFFAOYSA-N tribenzylphosphane Chemical compound C=1C=CC=CC=1CP(CC=1C=CC=CC=1)CC1=CC=CC=C1 IFXORIIYQORRMJ-UHFFFAOYSA-N 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- DHWBYAACHDUFAT-UHFFFAOYSA-N tricyclopentylphosphane Chemical compound C1CCCC1P(C1CCCC1)C1CCCC1 DHWBYAACHDUFAT-UHFFFAOYSA-N 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
- DMEUUKUNSVFYAA-UHFFFAOYSA-N trinaphthalen-1-ylphosphane Chemical compound C1=CC=C2C(P(C=3C4=CC=CC=C4C=CC=3)C=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 DMEUUKUNSVFYAA-UHFFFAOYSA-N 0.000 description 1
- SJHCUXCOGGKFAI-UHFFFAOYSA-N tripropan-2-yl phosphite Chemical compound CC(C)OP(OC(C)C)OC(C)C SJHCUXCOGGKFAI-UHFFFAOYSA-N 0.000 description 1
- QOPBTFMUVTXWFF-UHFFFAOYSA-N tripropyl phosphite Chemical compound CCCOP(OCCC)OCCC QOPBTFMUVTXWFF-UHFFFAOYSA-N 0.000 description 1
- ILLOBGFGKYTZRO-UHFFFAOYSA-N tris(2-ethylhexyl) phosphite Chemical compound CCCCC(CC)COP(OCC(CC)CCCC)OCC(CC)CCCC ILLOBGFGKYTZRO-UHFFFAOYSA-N 0.000 description 1
- MHDLYQWLYLNKDL-UHFFFAOYSA-N tris(2-tert-butyl-4-methoxyphenyl) phosphite Chemical compound CC(C)(C)C1=CC(OC)=CC=C1OP(OC=1C(=CC(OC)=CC=1)C(C)(C)C)OC1=CC=C(OC)C=C1C(C)(C)C MHDLYQWLYLNKDL-UHFFFAOYSA-N 0.000 description 1
- HBYRZSMDBQVSHO-UHFFFAOYSA-N tris(2-tert-butyl-4-methylphenyl) phosphite Chemical compound CC(C)(C)C1=CC(C)=CC=C1OP(OC=1C(=CC(C)=CC=1)C(C)(C)C)OC1=CC=C(C)C=C1C(C)(C)C HBYRZSMDBQVSHO-UHFFFAOYSA-N 0.000 description 1
- LFNXCUNDYSYVJY-UHFFFAOYSA-N tris(3-methylphenyl)phosphane Chemical compound CC1=CC=CC(P(C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)=C1 LFNXCUNDYSYVJY-UHFFFAOYSA-N 0.000 description 1
- UYUUAUOYLFIRJG-UHFFFAOYSA-N tris(4-methoxyphenyl)phosphane Chemical compound C1=CC(OC)=CC=C1P(C=1C=CC(OC)=CC=1)C1=CC=C(OC)C=C1 UYUUAUOYLFIRJG-UHFFFAOYSA-N 0.000 description 1
- FEVFLQDDNUQKRY-UHFFFAOYSA-N tris(4-methylphenyl) phosphite Chemical compound C1=CC(C)=CC=C1OP(OC=1C=CC(C)=CC=1)OC1=CC=C(C)C=C1 FEVFLQDDNUQKRY-UHFFFAOYSA-N 0.000 description 1
- WXAZIUYTQHYBFW-UHFFFAOYSA-N tris(4-methylphenyl)phosphane Chemical compound C1=CC(C)=CC=C1P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 WXAZIUYTQHYBFW-UHFFFAOYSA-N 0.000 description 1
- NZIQBDROTUFRHZ-UHFFFAOYSA-N tritert-butyl phosphite Chemical compound CC(C)(C)OP(OC(C)(C)C)OC(C)(C)C NZIQBDROTUFRHZ-UHFFFAOYSA-N 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Images
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D61/00—Processes of separation using semi-permeable membranes, e.g. dialysis, osmosis or ultrafiltration; Apparatus, accessories or auxiliary operations specially adapted therefor
- B01D61/02—Reverse osmosis; Hyperfiltration ; Nanofiltration
- B01D61/027—Nanofiltration
-
- 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
- B01J38/48—Liquid treating or treating in liquid phase, e.g. dissolved or suspended
-
- 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
- B01D53/22—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 by diffusion
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D61/00—Processes of separation using semi-permeable membranes, e.g. dialysis, osmosis or ultrafiltration; Apparatus, accessories or auxiliary operations specially adapted therefor
- B01D61/02—Reverse osmosis; Hyperfiltration ; Nanofiltration
-
- 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
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
-
- 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
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
- B01J31/1845—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing phosphorus
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2311/00—Details relating to membrane separation process operations and control
- B01D2311/26—Further operations combined with membrane separation processes
- B01D2311/2653—Degassing
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2313/00—Details relating to membrane modules or apparatus
- B01D2313/14—Specific spacers
- B01D2313/143—Specific spacers on the feed side
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2325/00—Details relating to properties of membranes
- B01D2325/30—Chemical resistance
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2325/00—Details relating to properties of membranes
- B01D2325/38—Hydrophobic membranes
-
- 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
- B01J2231/32—Addition reactions to C=C or C-C triple bonds
- B01J2231/321—Hydroformylation, metalformylation, carbonylation or hydroaminomethylation
-
- 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
-
- 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
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Water Supply & Treatment (AREA)
- Nanotechnology (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Analytical Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Separation Using Semi-Permeable Membranes (AREA)
Description
Rtot=1−(1−(1−Φ)exp(1−R)/Φ)=0.81に従い、13の所定濃縮係数の場合に、13×0.81×171ppmにより1801ppmであるべきである。実際にそれは、単に1255ppmである。クラスター化及び実験装置の壁上の沈殿が、この低いテスト結果の原因であると思われる。実際にこの結果は、溶解された活性触媒−リガンド−系の受け入れられない損失を意味している。
ホスフィン:トリフェニルホスフィン、トリス(p−トリル)ホスフィン、トリス(m−トリル)ホスフィン、トリス(o−トリル)ホスフィン、トリス(p−メトキシフェニル)ホスフィン、トリス(p−ジメチルアミノフェニル)ホスフィン、トリシクロヘキシルホスフィン、トリシクロペンチルホスフィン、トリエチルホスフィン、トリ−(1−ナフチル)ホスフィン、トリベンジルホスフィン、トリ−n−ブチルホスフィン、トリ−t−ブチルホスフィン。
アシル−又はヘテロアシルホスファイト又はアシル−又はヘテロアシルホスファイト−基を有するリガンドを有するのが特別好ましい。アシルホスファイト又はアシルホスファイト−基を有するリガンド、それらの製造及びヒドロホルミル化時のそれらの使用は、例えばDE 10053272中に記載されており、本発明の開示の要素である。ヘテロアシルホスファイト及びヘテロアシルホスファイト−基を有するリガンド、それらの製造及びヒドロホルミル化でのそれらの使用は、例えばDE 102004013514中に記載されている。
tは、基CR16R17、SiR16R17、NR16、O又はSを表し、R16及びR17はR5又はR6と同様に定義され、nは0又は1であり、位置a及びbは結合点としての役目をしている]の基を表す。
図5に示されているような実験装置中で、合成ガスを用いてトリ−n−ブテンのヒドロホルミル化反応を実施して、イソトリデカナールにした。引き続きナノ濾過を用いて、後続のヒドロホルミル化反応で再使用するための触媒−リガンド系の分離を行った。双方のプロセス工程をバッチ法で順次に実施した。図4中には、このプロセスラインが系統的に示されている。1プロセスラインで合計4つのヒドロホルミル化及び3つのナノ濾過工程を交互に実施した。
・トリ−n−ブテン(OXENO Olefinchemie GmbH) 996g
・Rh(ロジウムノナネート;ノナノールのロジウムアルコレートとして)8.72mg
・リガンドとしてのAlkanox 240(トリス(2,4−ジ−t−ブチルフェニル)ホスファイト)(Great Lakes Chemical Corp.) 297mg。
このナノ濾過の間に、この系から、この膜を経て主として反応生成物から成っている透過液(3a)が取り出された。触媒及びリガンドAlkanoxは、このフィード−バッチ−プロセス(Feed-Batch-Prozess)の範囲内で、膜によって充分に保留され、保持液室中で富化された。全ての反応生成物がナノ濾過装置中に移行し、かつ約5の容積濃縮係数(volumetrische Konzentrierungsfaktor)まで富化された後に、得られた濃縮物(4a)(これは、この系中に残っている触媒−リガンド−錯体を含有している)を、新鮮出発物質(T)(トリブテン)と混合して、この混合物(5)を反応釜中に送り戻した。260バールの合成ガス圧(CO/H2、質量比1:1)下で、150℃での4時間にわたる新たな反応の後に、反応生成物混合物(2)を60℃まで冷却し、かつ合成ガス圧17バールまで脱ガスした後に、再び溶解された触媒系と一緒にナノ濾過装置(N)まで移行させた。この方法で、合計4つのバッチ−反応と3つのナノ濾過サイクルを交互に実施した。図5はこの実験構成を示している。
もう一つの実験で例1と同様な処置を行った。この例の最初の反応のために、次の出発物質を装入した:
・ トリ−n−ブテン 1023.6g
・ Rh(ロジウムノナネート) 8.75mg
・ Alkanox240(トリス(2,4−ジ−t−ブチルフェニル)ホスファイト)
291mg 。
Claims (27)
- ヒドロホルミル化生成物及び有機溶剤を含有している、非水性のヒドロホルミル化−反応混合物から、溶解されている、有機燐−リガンドを有するロジウム、コバルト、イリジウム、ニッケル、パラジウム、白金、鉄、ルテニウム、オスミウム、クロム、モリブデン及びタングステンからなる群から選択される金属の錯体触媒を分離する方法であって、有機燐−リガンドよりもヒドロホルミル化生成物をより良好に通過させる膜少なくとも1枚を使用する膜分離工程少なくとも一つを有する方法において、ヒドロホルミル化−反応混合物を、この膜分離工程で膜上に導き、この際、この膜分離工程を、供給液中、保持液中及び透過液中の一酸化炭素−蒸気分圧が低くとも200kPaで実施することを特徴とする、溶解されている錯体触媒を分離する方法。
- 2以上の膜分離工程を使用することを特徴とする、請求項1に記載の方法。
- 1膜分離工程で2枚以上の膜を使用することを特徴とする、請求項1又は2に記載の方法。
- ヒドロホルミル化−反応混合物を、ヒドロホルミル化反応器中の圧力の90〜100%に相当する圧力で膜上に導くことを特徴とする、請求項1から3までのいずれか1項に記載の方法。
- ヒドロホルミル化−反応混合物を、ヒドロホルミル化反応器中の圧力の60〜90%に相当する圧力で膜上に導くことを特徴とする、請求項1から3までのいずれか1項に記載の方法。
- ヒドロホルミル化−反応混合物を、一酸化炭素−蒸気分圧が低くても200kPaであることを条件として、ヒドロホルミル化反応器中の圧力の40〜60%に相当する圧力で膜上に導くことを特徴とする、請求項1から3までのいずれか1項に記載の方法。
- ヒドロホルミル化−反応混合物を、一酸化炭素−蒸気分圧が低くても200kPaであることを条件として、ヒドロホルミル化反応器中の圧力の40%を下回る圧力で、膜上に導くことを特徴とする、請求項1から3までのいずれか1項に記載の方法。
- 膜分離工程での分離を、30〜150℃の温度で実施することを特徴とする、請求項1から7までのいずれか1項に記載の方法。
- 膜分離工程での分離を、低くても1MPaの膜間圧力差で実施することを特徴とする、請求項1から8までのいずれか1項に記載の方法。
- 分離を、膜間圧力差1〜10MPaで実施することを特徴とする、請求項9に記載の方法。
- 膜は、分離活性層としてポリジメチルシロキサン(PDMS)、ポリイミド(PI)、ポリアミドイミド(PAI)、アクリロニトリル/グリシジルメタクリレート(PANGMA)、ポリアミド(PA)又はポリエーテルエーテルケトン(PEEK)からのポリマー層を有している膜から選択されているか、又は分離活性層は、固有微細孔度を有するポリマー(PIM)から構成されているか、又は分離活性層は、疎水性化されたセラミック膜上を覆って構成されていることを特徴とする、請求項1から10までのいずれか1項に記載の方法。
- 溶剤系中で、1000g/モルの分子量までの分子を通過可能である膜を使用することを特徴とする、請求項1から11までのいずれか1項に記載の方法。
- 膜を、開放路クッションモジュール系を有する膜モジュール(ここで、膜は熱的に溶接されて膜バッグにされている)又は開放路(ワイド−スぺーサー)巻きモジュール(ここで、膜は接着されて膜バッグにされ、かつフィードスぺーサーと共に透過液捕集管の周りに巻き付けられている)を有する膜モジュールの形で使用することを特徴とする、請求項1から12までのいずれか1項に記載の方法。
- 0.1〜15m/secの膜の越流速度で膜分離工程を実施することを特徴とする、請求項1から13までのいずれか1項に記載の方法。
- 第1膜分離工程の第1膜上に導かれる流(送り戻された保持液を包含する反応器の流入分)と透過液流との容積流量比は、10〜10000対1であることを特徴とする、請求項1から14までのいずれか1項に記載の方法。
- ヒドロホルミル化生成物に対する有機燐−リガンドの分子−体積比は、1.5以上であることを特徴とする、請求項1から15までのいずれか1項に記載の方法。
- ヒドロホルミル化生成物として、炭素原子数5〜17を有するアルデヒドから選択されるアルデヒドを有している、ヒドロホルミル化−反応混合物を使用することを特徴とする、請求項1から16までのいずれか1項に記載の方法。
- 有機燐−リガンドとして、アシル−又はヘテロアシルホスファイトを有している、ヒドロホルミル化−反応混合物を使用することを特徴とする、請求項1から17までのいずれか1項に記載の方法。
- 有機燐−リガンドが遊離リガンドとして存在している、ヒドロホルミル化−反応混合物を使用することを特徴とする、請求項1から18までのいずれか1項に記載の方法。
- 第1膜分離工程への流入分中のアルデヒド生成物と遊離リガンドとのモル比は、10超対1であることを特徴とする、請求項19に記載の方法。
- 金属−錯体触媒は、金属としてロジウム、コバルト、イリジウム、ルテニウム又はオスミウムから選択される1つの金属を有していることを特徴とする、請求項1から20までのいずれか1項に記載の方法。
- 金属−錯体触媒は、金属としてロジウムを有していることを特徴とする、請求項1から21までのいずれか1項に記載の方法。
- 一つの膜分離工程の後に、ヒドロホルミル化生成物の分離のための一つの熱的分離工程を実施することを特徴とする、請求項1から22までのいずれか1項に記載の方法。
- 透過液からヒドロホルミル化生成物を熱的分離工程により分離することを特徴とする、請求項1から23までのいずれか1項に記載の方法。
- 高沸点物及び触媒錯体を有している熱的分離工程の塔底生成物を、もう一つの膜分離工程に供給し、この際、塔底生成物から高沸点物の一部分を透過液として分離し、かつ保持液中に残っている触媒錯体の少なくとも一部分を反応器中に送り戻すことを特徴とする、請求項23又は24のいずれか1項に記載の方法。
- 少なくとも一つの第1膜分離工程、少なくとも一つの熱的分離工程及び場合により引き続く少なくとも一つの膜分離工程からなる方法の錯体触媒の全保留率は98%を上回っていることを特徴とする、請求項22から25までのいずれか1項に記載の方法。
- 透過液流中、付加的に脱ガス部Eが存在し、この中で透過液流から、放圧によってガス状の内容物質が除去されることを特徴とする、請求項1から26までのいずれか1項に記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102005046250.2A DE102005046250B4 (de) | 2005-09-27 | 2005-09-27 | Anlage zur Abtrennung von organischen Übergangsmetallkomplexkatalysatoren |
DE102005046250.2 | 2005-09-27 | ||
PCT/EP2006/066181 WO2007036424A1 (de) | 2005-09-27 | 2006-09-08 | Verfahren zur abtrennung von organischen übergangsmetallkomplexkatalysatoren |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2009513320A JP2009513320A (ja) | 2009-04-02 |
JP2009513320A5 JP2009513320A5 (ja) | 2011-09-29 |
JP5091142B2 true JP5091142B2 (ja) | 2012-12-05 |
Family
ID=37635694
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2008532709A Active JP5091142B2 (ja) | 2005-09-27 | 2006-09-08 | 有機遷移金属錯体触媒を分離する方法 |
Country Status (11)
Country | Link |
---|---|
US (1) | US8226829B2 (ja) |
EP (1) | EP1931472B1 (ja) |
JP (1) | JP5091142B2 (ja) |
KR (1) | KR101337117B1 (ja) |
CN (1) | CN101272860B (ja) |
AT (1) | ATE419917T1 (ja) |
DE (2) | DE102005046250B4 (ja) |
ES (1) | ES2320698T3 (ja) |
PL (1) | PL1931472T3 (ja) |
TW (1) | TWI418396B (ja) |
WO (1) | WO2007036424A1 (ja) |
Families Citing this family (40)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102006003618A1 (de) * | 2006-01-26 | 2007-08-02 | Oxeno Olefinchemie Gmbh | Verfahren zur Abtrennung von Metall-Komplexkatalysatoren aus Telomerisationsgemischen |
DE102007054885A1 (de) * | 2007-11-15 | 2009-05-20 | Evonik Degussa Gmbh | Verfahren zur Fraktionierung oxidischer Nanopartikel durch Querstrom-Membranfiltration |
DE102008020688B3 (de) * | 2008-04-24 | 2009-11-05 | Evonik Stockhausen Gmbh | Verfahren zur Herstellung und Aufreinigung wässriger Phasen |
DE102008002188A1 (de) | 2008-06-03 | 2009-12-10 | Evonik Oxeno Gmbh | Verfahren zur Abtrennung von 1-Buten aus C4-haltigen Kohlenwasserstoffströmen durch Hydroformylierung |
DE102008044946B4 (de) * | 2008-08-29 | 2022-06-15 | Evonik Superabsorber Gmbh | Einsatz von Schaumkörpern in Oxidations-Reaktoren zur Herstellung ungesättigter Carbonsäuren |
DE102009026819A1 (de) | 2008-09-08 | 2010-03-11 | Evonik Röhm Gmbh | Monomermischung, Polymer, Beschichtungsmittel und Verfahren zur Herstellung einer Beschichtung |
DE102008043422B3 (de) | 2008-11-03 | 2010-01-07 | Evonik Degussa Gmbh | Verfahren zur Aufreinigung niedermolekularer Hydridosilane |
DE102008060888A1 (de) | 2008-12-09 | 2010-06-10 | Evonik Stockhausen Gmbh | Verfahren zur Herstellung von Acrolein umfassend die Aufarbeitung einer Rohglycerin-Phase |
DE102009001230A1 (de) * | 2009-02-27 | 2010-09-02 | Evonik Oxeno Gmbh | Verfahren zur Abtrennung und teilweiser Rückführung von Übergangsmetallen bzw. deren katalytisch wirksamen Komplexverbindungen aus Prozessströmen |
DE102009001225A1 (de) * | 2009-02-27 | 2010-09-02 | Evonik Oxeno Gmbh | Verfahren zur Anreicherung eines Homogenkatalysators aus einem Prozessstrom |
DE102009016652A1 (de) * | 2009-04-07 | 2010-10-14 | Oxea Gmbh | Verfahren zur Aufarbeitung eines flüssigen Hydroformylierungsaustrags |
CN102470329B (zh) | 2009-07-23 | 2015-06-24 | 赢创纤维有限公司 | 由聚合溶液制成的聚酰亚胺膜 |
DE102009029050A1 (de) | 2009-08-31 | 2011-03-03 | Evonik Oxeno Gmbh | Organophosphorverbindungen basierend auf Tetraphenol(TP)-substituierten Strukturen |
DE102009047351A1 (de) | 2009-12-01 | 2011-06-09 | Evonik Goldschmidt Gmbh | Komposit-Siliconmembranen mit hoher Trennwirkung |
EP2363402A1 (de) * | 2010-03-01 | 2011-09-07 | Evonik Oxeno GmbH | Polyhedrale Oligomere Silsesquioxan (POSS)-verbundene Liganden und deren Verwendung |
DE102011082441A1 (de) * | 2011-09-09 | 2013-03-14 | Evonik Oxeno Gmbh | Strahlschlaufenreaktor mit Nanofiltration |
CA2858351C (en) | 2011-12-20 | 2016-11-22 | Dow Technology Investments Llc | A hydroformylation process |
WO2013107902A1 (en) * | 2012-01-20 | 2013-07-25 | Dsm Ip Assets B.V. | Process for the separation of a dissolved catalyst system from an alkoxycarbonylation reaction mixture |
DE102012202779A1 (de) * | 2012-02-23 | 2013-08-29 | Evonik Oxeno Gmbh | Verfahren und Vorrichtung zur technischen Hydroformylierung von Isobuten und zum Auftrennen des Produktgemisches |
WO2013156600A1 (en) * | 2012-04-20 | 2013-10-24 | Vlaamse Instelling Voor Technologisch Onderzoek (Vito) | Improved dilute chemical reaction process with membrane separation step |
JP2015536302A (ja) | 2012-10-12 | 2015-12-21 | エボニック インダストリーズ アクチエンゲゼルシャフトEvonik Industries AG | C5アルデヒドを製造するための長時間安定した方法 |
DE102012223572A1 (de) * | 2012-12-18 | 2014-06-18 | Evonik Industries Ag | Steuerung der Viskosität von Reaktionslösungen in Hydroformylierungverfahren |
DE102013203117A1 (de) * | 2013-02-26 | 2014-08-28 | Evonik Industries Ag | Optimierte Trenntechnik zur Aufarbeitung von homogen katalysierten Hydroformylierungsmischungen |
DE102013208759A1 (de) * | 2013-05-13 | 2014-11-13 | Evonik Industries Ag | Abtrennung von Homogenkatalysatoren mittels einer geregelten Membrantrenneinheit |
DE102013215004A1 (de) | 2013-07-31 | 2015-02-05 | Evonik Industries Ag | Membrankaskade mit sinkender Trenntemperatur |
DE102013221708A1 (de) * | 2013-10-25 | 2015-04-30 | Evonik Industries Ag | Strahlschlaufenreaktor mit Nanofiltration und Gasseparator |
DE102014002103B4 (de) | 2014-02-15 | 2020-10-22 | Oxea Gmbh | Verfahren zur Regenerierung gebrauchter Hydroformylierungskatalysatoren |
US10155200B2 (en) * | 2015-02-18 | 2018-12-18 | Evonik Degussa Gmbh | Separation off of a homogeneous catalyst from a reaction mixture with the help of organophilic nanofiltration |
EP3222344A1 (de) * | 2016-03-21 | 2017-09-27 | Evonik Degussa GmbH | Kontinuierliches verfahren zur herstellung einer chemischen verbindung |
CN107473957A (zh) * | 2017-06-08 | 2017-12-15 | 赢创特种化学(上海)有限公司 | 从均相的有机液体组合物中富集铬化合物的方法 |
US10654784B2 (en) * | 2018-10-05 | 2020-05-19 | Evonik Operations Gmbh | Process for hydroformylating short-chain olefins in the gas phase |
WO2020190556A1 (en) | 2019-03-18 | 2020-09-24 | Novomer, Inc. | Membrane separation system, and uses thereof |
EP3945088A1 (de) | 2020-07-30 | 2022-02-02 | Röhm GmbH | Vorgehen zur minimierung des aktivitätsverlusts bei im kreislaufbetrieb ausgeführten reaktionsschritten |
EP3945085B1 (de) * | 2020-07-30 | 2024-01-03 | Evonik Oxeno GmbH & Co. KG | Verfahren zur herstellung von aldehyden und abtrennung des katalysatorsystems mittels membrantrennung |
CN118103532A (zh) * | 2021-11-11 | 2024-05-28 | 陶氏技术投资有限责任公司 | 用于从加氢甲酰化过程中回收铑的方法 |
CN113996340B (zh) * | 2021-11-16 | 2023-12-19 | 万华化学集团股份有限公司 | 一种用于氢甲酰化反应的新型催化剂体系及氢甲酰化反应方法 |
EP4183767A1 (de) | 2021-11-19 | 2023-05-24 | Evonik Operations GmbH | Verfahren zur herstellung von aldehyden und kühlung eines stoffstroms |
EP4183768A1 (de) * | 2021-11-19 | 2023-05-24 | Evonik Operations GmbH | Verfahren zur herstellung von aldehyden und kühlung eines stoffstroms |
CN114160205A (zh) * | 2021-12-13 | 2022-03-11 | 浙江迪萧科技有限公司 | 一种有机料液中络合物催化剂的浓缩回收方法 |
EP4223737A1 (de) * | 2022-02-08 | 2023-08-09 | Evonik Operations GmbH | Optimierte thermische trennung durch vorherigen gasaustausch |
Family Cites Families (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1312076A (en) * | 1970-05-15 | 1973-04-04 | Bp Chem Int Ltd | Hydroformylation process |
ZA78147B (en) * | 1977-01-25 | 1978-11-29 | Union Carbide Corp | Improved hydroformylation process |
US5215667A (en) * | 1991-08-20 | 1993-06-01 | Exxon Chemical Patents Inc. | Method for separating water soluble noble metal catalyst from a noble metal catalyzed hydroformylation reaction |
US5395979A (en) * | 1993-02-25 | 1995-03-07 | Exxon Chemical Patents Inc. | Method for separating catalyst from a hydroformylation reaction product using alkylated ligands |
US5298669A (en) * | 1993-03-23 | 1994-03-29 | Exxon Chemical Patent Inc. | Perstraction sweep stream for a membrane reactor |
KR970703805A (ko) * | 1995-05-01 | 1997-08-09 | 유니온 카바이드 케미칼즈 앤드 플라스틱스 테크놀러지 코포레이션 | 막 분리방법(Membrane Separation) |
US5731472A (en) * | 1995-12-06 | 1998-03-24 | Union Carbide Chemicals & Plastics Technology Corporation | Metal-ligand complex catalyzed processes |
EP0839787A1 (en) * | 1996-11-04 | 1998-05-06 | Dsm N.V. | Process for the preparation of an aldehyde |
CA2204676A1 (en) * | 1996-05-15 | 1997-11-15 | Helmut Bahrmann | Process for preparing aldehydes |
DE19801437A1 (de) * | 1998-01-16 | 1999-07-22 | Basf Ag | Verfahren zur Herstellung von Aldehyden |
US6090987A (en) * | 1998-07-06 | 2000-07-18 | Union Carbide Chemicals & Plastics Technology Corporation | Metal-ligand complex catalyzed processes |
US6252123B1 (en) * | 1998-07-09 | 2001-06-26 | Union Carbide Chemicals & Plastics Technology Corporation | Membrane separation process for metal complex catalysts |
EP1103303A1 (en) * | 1999-11-23 | 2001-05-30 | Dsm N.V. | Process to separate a rhodium/phosphite ligand complex and free phosphite ligand complex from a hydroformylation mixture |
US6610891B1 (en) * | 1999-12-03 | 2003-08-26 | Mitsubishi Chemical Corporation | Method of producing aldehydes |
EP1296992B1 (de) * | 2000-06-26 | 2008-04-23 | Basf Se | Phosphacyclohexane und ihre verwendung in der hydroformylierung von olefinen |
DE10048301A1 (de) * | 2000-09-29 | 2002-04-11 | Oxeno Olefinchemie Gmbh | Stabilisierung von Rhodiumkatalysatoren für die Hydroformylierung von Olefinen |
DE10128144A1 (de) | 2001-06-09 | 2002-12-12 | Oxeno Olefinchemie Gmbh | Verfahren zur Telomerisation von nicht cyclischen Olefinen |
JP2003080036A (ja) * | 2001-09-07 | 2003-03-18 | Mitsubishi Heavy Ind Ltd | 純水製造方法 |
DE10312829A1 (de) | 2002-06-29 | 2004-01-22 | Oxeno Olefinchemie Gmbh | Verfahren zur Telomerisation von nicht cyclischen Olefinen |
DE102004013514A1 (de) * | 2004-03-19 | 2005-10-06 | Oxeno Olefinchemie Gmbh | Verfahren zur Hydroformylierung von Olefinen in Anwesenheit von neuen phosphororganischen Verbindungen |
DE102005036039A1 (de) | 2004-08-28 | 2006-03-02 | Oxeno Olefinchemie Gmbh | Verfahren zur Herstellung von 2,7-Octadienylderivaten |
DE102005036038A1 (de) | 2004-08-28 | 2006-03-02 | Oxeno Olefinchemie Gmbh | Verfahren zur Telomerisation von nicht cyclischen Olefinen |
US7353316B2 (en) * | 2006-03-24 | 2008-04-01 | Micron Technology, Inc. | System and method for re-routing signals between memory system components |
-
2005
- 2005-09-27 DE DE102005046250.2A patent/DE102005046250B4/de not_active Expired - Fee Related
-
2006
- 2006-09-08 CN CN2006800358000A patent/CN101272860B/zh active Active
- 2006-09-08 EP EP06778422A patent/EP1931472B1/de active Active
- 2006-09-08 PL PL06778422T patent/PL1931472T3/pl unknown
- 2006-09-08 US US12/088,041 patent/US8226829B2/en active Active
- 2006-09-08 WO PCT/EP2006/066181 patent/WO2007036424A1/de active Application Filing
- 2006-09-08 KR KR1020087007298A patent/KR101337117B1/ko active IP Right Grant
- 2006-09-08 DE DE502006002616T patent/DE502006002616D1/de active Active
- 2006-09-08 JP JP2008532709A patent/JP5091142B2/ja active Active
- 2006-09-08 ES ES06778422T patent/ES2320698T3/es active Active
- 2006-09-08 AT AT06778422T patent/ATE419917T1/de not_active IP Right Cessation
- 2006-09-21 TW TW095134974A patent/TWI418396B/zh active
Also Published As
Publication number | Publication date |
---|---|
ATE419917T1 (de) | 2009-01-15 |
WO2007036424A1 (de) | 2007-04-05 |
EP1931472B1 (de) | 2009-01-07 |
CN101272860B (zh) | 2010-11-17 |
DE102005046250B4 (de) | 2020-10-08 |
PL1931472T3 (pl) | 2009-06-30 |
EP1931472A1 (de) | 2008-06-18 |
TWI418396B (zh) | 2013-12-11 |
CN101272860A (zh) | 2008-09-24 |
DE102005046250A1 (de) | 2007-03-29 |
TW200719947A (en) | 2007-06-01 |
KR101337117B1 (ko) | 2013-12-05 |
US20080251456A1 (en) | 2008-10-16 |
JP2009513320A (ja) | 2009-04-02 |
ES2320698T3 (es) | 2009-05-27 |
US8226829B2 (en) | 2012-07-24 |
KR20080053476A (ko) | 2008-06-13 |
DE502006002616D1 (de) | 2009-02-26 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP5091142B2 (ja) | 有機遷移金属錯体触媒を分離する方法 | |
KR101593259B1 (ko) | 공정 스트림으로부터 균일 촉매를 농축하는 방법 | |
TWI586644B (zh) | 氫甲醯化方法 | |
JP5371444B2 (ja) | テロメリゼーション混合物からの金属−錯体触媒の分離法 | |
JP3009229B2 (ja) | 膜分離方法 | |
JPH0451531B2 (ja) | ||
Bronger et al. | Phenoxaphosphino‐Modified Xantphos‐Type Ligands in the Rhodium‐Catalysed Hydroformylation of Internal and Terminal Alkenes | |
KR20070007830A (ko) | 유기인 화합물 존재 하의 올레핀 히드로포르밀화 방법 | |
US20160158703A1 (en) | Membrane cascade with falling separation temperature | |
US8445728B2 (en) | Method for reprocessing a liquid hydroformylation product | |
KR20150095891A (ko) | 히드로포르밀화 방법에서의 반응 용액의 점도의 제어 | |
TW201536409A (zh) | 具有奈米過濾的噴流迴路反應器和氣體分離器 | |
TWI605872B (zh) | 催化劑製備方法 | |
CN118317834A (zh) | 化合物、包含此类化合物的过渡金属络合物加氢甲酰化催化剂前体组合物和加氢甲酰化方法 | |
CN118338965A (zh) | 包含此类化合物的过渡金属络合物加氢甲酰化催化剂前体组合物和加氢甲酰化方法 | |
TW201840362A (zh) | 使去活化的氫甲醯化催化劑溶液再生的方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20090806 |
|
RD04 | Notification of resignation of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7424 Effective date: 20101228 Free format text: JAPANESE INTERMEDIATE CODE: A7424 Effective date: 20101227 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20110113 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20110218 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20110506 |
|
A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20110513 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20110615 |
|
A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20110622 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20110715 |
|
A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20110725 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20110815 |
|
A524 | Written submission of copy of amendment under article 19 pct |
Free format text: JAPANESE INTERMEDIATE CODE: A524 Effective date: 20110815 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20120307 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20120604 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20120815 |
|
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20120913 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20150921 Year of fee payment: 3 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 5091142 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
S111 | Request for change of ownership or part of ownership |
Free format text: JAPANESE INTERMEDIATE CODE: R313111 |
|
R350 | Written notification of registration of transfer |
Free format text: JAPANESE INTERMEDIATE CODE: R350 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
S533 | Written request for registration of change of name |
Free format text: JAPANESE INTERMEDIATE CODE: R313533 |
|
R350 | Written notification of registration of transfer |
Free format text: JAPANESE INTERMEDIATE CODE: R350 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
S111 | Request for change of ownership or part of ownership |
Free format text: JAPANESE INTERMEDIATE CODE: R313113 |
|
R350 | Written notification of registration of transfer |
Free format text: JAPANESE INTERMEDIATE CODE: R350 |