KR102157915B1 - 에틸렌의 하이드로포밀화를 위한 두자리 리간드 - Google Patents
에틸렌의 하이드로포밀화를 위한 두자리 리간드 Download PDFInfo
- Publication number
- KR102157915B1 KR102157915B1 KR1020157014700A KR20157014700A KR102157915B1 KR 102157915 B1 KR102157915 B1 KR 102157915B1 KR 1020157014700 A KR1020157014700 A KR 1020157014700A KR 20157014700 A KR20157014700 A KR 20157014700A KR 102157915 B1 KR102157915 B1 KR 102157915B1
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- South Korea
- Prior art keywords
- ligand
- hydroformylation
- reaction
- rhodium
- catalyst
- Prior art date
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- 239000003446 ligand Substances 0.000 title claims abstract description 112
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 title claims abstract description 18
- 239000005977 Ethylene Substances 0.000 title claims abstract description 18
- 238000007037 hydroformylation reaction Methods 0.000 title claims description 65
- 238000000034 method Methods 0.000 claims abstract description 87
- 239000003054 catalyst Substances 0.000 claims abstract description 63
- 239000010948 rhodium Substances 0.000 claims abstract description 42
- 229910052703 rhodium Inorganic materials 0.000 claims abstract description 35
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims abstract description 34
- 239000000203 mixture Substances 0.000 claims description 22
- 230000008569 process Effects 0.000 abstract description 62
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 21
- 239000001257 hydrogen Substances 0.000 abstract description 19
- 125000003118 aryl group Chemical group 0.000 abstract description 12
- 125000005843 halogen group Chemical group 0.000 abstract description 11
- 229910052698 phosphorus Inorganic materials 0.000 abstract description 11
- 125000001424 substituent group Chemical group 0.000 abstract description 10
- 125000001072 heteroaryl group Chemical group 0.000 abstract description 9
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract description 8
- 125000000217 alkyl group Chemical group 0.000 abstract description 8
- 229910052760 oxygen Inorganic materials 0.000 abstract description 7
- 239000011574 phosphorus Substances 0.000 abstract description 7
- -1 e.g. Substances 0.000 abstract description 6
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 6
- 125000000168 pyrrolyl group Chemical group 0.000 abstract description 6
- 125000002723 alicyclic group Chemical group 0.000 abstract description 5
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract description 5
- 229910052723 transition metal Inorganic materials 0.000 abstract description 5
- 150000003624 transition metals Chemical class 0.000 abstract description 5
- 125000003545 alkoxy group Chemical group 0.000 abstract description 4
- 229910052799 carbon Inorganic materials 0.000 abstract description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 4
- 125000002252 acyl group Chemical group 0.000 abstract description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 3
- 150000007942 carboxylates Chemical class 0.000 abstract description 3
- 125000004093 cyano group Chemical group *C#N 0.000 abstract description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 abstract description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 description 51
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 48
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 48
- 239000000243 solution Substances 0.000 description 34
- 239000011541 reaction mixture Substances 0.000 description 32
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
- 150000001299 aldehydes Chemical class 0.000 description 27
- 229910052751 metal Inorganic materials 0.000 description 26
- 239000002184 metal Substances 0.000 description 26
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 25
- 229910002091 carbon monoxide Inorganic materials 0.000 description 25
- 239000000047 product Substances 0.000 description 22
- 238000004519 manufacturing process Methods 0.000 description 20
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 239000007788 liquid Substances 0.000 description 18
- 239000012530 fluid Substances 0.000 description 17
- 238000000926 separation method Methods 0.000 description 17
- 238000005481 NMR spectroscopy Methods 0.000 description 16
- 239000000706 filtrate Substances 0.000 description 16
- 239000002904 solvent Substances 0.000 description 16
- 238000003756 stirring Methods 0.000 description 16
- 239000007858 starting material Substances 0.000 description 15
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
- 150000001336 alkenes Chemical class 0.000 description 13
- 125000005842 heteroatom Chemical group 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 11
- 229910052786 argon Inorganic materials 0.000 description 11
- 239000007789 gas Substances 0.000 description 11
- 238000000607 proton-decoupled 31P nuclear magnetic resonance spectroscopy Methods 0.000 description 11
- 239000012429 reaction media Substances 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 238000004064 recycling Methods 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- 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 10
- 238000004821 distillation Methods 0.000 description 9
- 238000011065 in-situ storage Methods 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 150000002431 hydrogen Chemical class 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- 0 *C(C1)(*=C)c2c(*)c(*)c(*)c(P(*)*)c2OC1(CC1(*)S)Oc(c(P(*)*)c2*)c1c(*)c2O* Chemical compound *C(C1)(*=C)c2c(*)c(*)c(*)c(P(*)*)c2OC1(CC1(*)S)Oc(c(P(*)*)c2*)c1c(*)c2O* 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical group C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 239000012018 catalyst precursor Substances 0.000 description 5
- 125000006659 (C1-C20) hydrocarbyl group Chemical group 0.000 description 4
- UTXIFKBYNJRJPH-UHFFFAOYSA-N 1-(2-hydroxy-5,6,7,8-tetrahydronaphthalen-1-yl)-5,6,7,8-tetrahydronaphthalen-2-ol Chemical compound C1CCCC2=C1C=CC(O)=C2C1=C2CCCCC2=CC=C1O UTXIFKBYNJRJPH-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- GGRQQHADVSXBQN-FGSKAQBVSA-N carbon monoxide;(z)-4-hydroxypent-3-en-2-one;rhodium Chemical compound [Rh].[O+]#[C-].[O+]#[C-].C\C(O)=C\C(C)=O GGRQQHADVSXBQN-FGSKAQBVSA-N 0.000 description 4
- PKBKEYFJDIDUHQ-UHFFFAOYSA-N chloro-bis(1h-indol-2-yl)phosphane Chemical compound C1=CC=C2NC(P(C=3NC4=CC=CC=C4C=3)Cl)=CC2=C1 PKBKEYFJDIDUHQ-UHFFFAOYSA-N 0.000 description 4
- HZOOKKJFGKCMIB-UHFFFAOYSA-N chloro-bis(1h-pyrrol-2-yl)phosphane Chemical compound C=1C=CNC=1P(Cl)C1=CC=CN1 HZOOKKJFGKCMIB-UHFFFAOYSA-N 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 239000000470 constituent Substances 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 229910052732 germanium Inorganic materials 0.000 description 4
- 239000012528 membrane Substances 0.000 description 4
- 150000002894 organic compounds Chemical class 0.000 description 4
- 239000002243 precursor Substances 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 3
- PYZPABZGIRHQTA-UHFFFAOYSA-N [2-(4-methyl-2-phenylpiperazin-1-yl)pyridin-3-yl]methanol Chemical compound C1N(C)CCN(C=2C(=CC=CN=2)CO)C1C1=CC=CC=C1 PYZPABZGIRHQTA-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 229910017052 cobalt Inorganic materials 0.000 description 3
- 239000010941 cobalt Substances 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
- 229910052707 ruthenium Inorganic materials 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 238000004009 13C{1H}-NMR spectroscopy Methods 0.000 description 2
- CHIFTAQVXHNVRW-UHFFFAOYSA-N 1h-indole-3-carbonitrile Chemical compound C1=CC=C2C(C#N)=CNC2=C1 CHIFTAQVXHNVRW-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 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 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 150000005347 biaryls Chemical group 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- SRBHYEPINHMPMU-UHFFFAOYSA-N chloro-bis(3-methyl-1h-indol-2-yl)phosphane Chemical compound N1C2=CC=CC=C2C(C)=C1P(Cl)C1=C(C)C2=CC=CC=C2N1 SRBHYEPINHMPMU-UHFFFAOYSA-N 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
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- 239000012065 filter cake Substances 0.000 description 2
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- 238000010438 heat treatment Methods 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 125000000743 hydrocarbylene group Chemical group 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
- 150000002576 ketones Chemical class 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- RPYNUJSCKCFXSR-UHFFFAOYSA-N methyl 2-[chloro-(3-methoxycarbonyl-1h-indol-2-yl)phosphanyl]-1h-indole-3-carboxylate Chemical compound N1C2=CC=CC=C2C(C(=O)OC)=C1P(Cl)C1=C(C(=O)OC)C2=CC=CC=C2N1 RPYNUJSCKCFXSR-UHFFFAOYSA-N 0.000 description 2
- JVEHJSIFWIIFHM-UHFFFAOYSA-N n-[chloro(diethylamino)phosphanyl]-n-ethylethanamine Chemical compound CCN(CC)P(Cl)N(CC)CC JVEHJSIFWIIFHM-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
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- 125000006413 ring segment Chemical group 0.000 description 2
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- GGQQNYXPYWCUHG-RMTFUQJTSA-N (3e,6e)-deca-3,6-diene Chemical compound CCC\C=C\C\C=C\CC GGQQNYXPYWCUHG-RMTFUQJTSA-N 0.000 description 1
- MBVAQOHBPXKYMF-LNTINUHCSA-N (z)-4-hydroxypent-3-en-2-one;rhodium Chemical compound [Rh].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O MBVAQOHBPXKYMF-LNTINUHCSA-N 0.000 description 1
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- BNRGNYFCHSMVFS-UHFFFAOYSA-N 2-(6-hydroxy-2,3-dimethylphenyl)-3,4-dimethylphenol Chemical compound CC1=CC=C(O)C(C=2C(=CC=C(C)C=2C)O)=C1C BNRGNYFCHSMVFS-UHFFFAOYSA-N 0.000 description 1
- BWRRWBIBNBVHQF-UHFFFAOYSA-N 4-(3-pyridin-2-yl-1,2,4-oxadiazol-5-yl)butanoic acid Chemical compound O1C(CCCC(=O)O)=NC(C=2N=CC=CC=2)=N1 BWRRWBIBNBVHQF-UHFFFAOYSA-N 0.000 description 1
- XBEJQZBOZHAEKK-UHFFFAOYSA-N 6-(2-hydroxy-3,4-dimethylphenyl)-2,3-dimethylphenol Chemical compound OC1=C(C)C(C)=CC=C1C1=CC=C(C)C(C)=C1O XBEJQZBOZHAEKK-UHFFFAOYSA-N 0.000 description 1
- NMVVBVMYPLMIOU-UHFFFAOYSA-N 6-tert-butyl-2-(3-tert-butyl-2-hydroxy-5,6-dimethylphenyl)-3,4-dimethylphenol Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C=2C(=C(C=C(C)C=2C)C(C)(C)C)O)=C1C NMVVBVMYPLMIOU-UHFFFAOYSA-N 0.000 description 1
- PMKYNXBUZIFIHB-UHFFFAOYSA-N C(CCc1c2-c(c(CCCC3)c3cc3)c3OP([n]3cccc3)[n]3cccc3)Cc1ccc2OP([n]1cccc1)[n]1cccc1 Chemical compound C(CCc1c2-c(c(CCCC3)c3cc3)c3OP([n]3cccc3)[n]3cccc3)Cc1ccc2OP([n]1cccc1)[n]1cccc1 PMKYNXBUZIFIHB-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VADPFECQVIUDCF-UHFFFAOYSA-N ClP([n]1cccc1)[n]1cccc1 Chemical compound ClP([n]1cccc1)[n]1cccc1 VADPFECQVIUDCF-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000004803 Di-2ethylhexylphthalate Substances 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- LSGKMZLPZFPAIN-UHFFFAOYSA-N Oxime-1H-Indole-3-carboxaldehyde Natural products C1=CC=C2C(C(=O)N)=CNC2=C1 LSGKMZLPZFPAIN-UHFFFAOYSA-N 0.000 description 1
- 238000004639 Schlenk technique Methods 0.000 description 1
- MOFINMJRLYEONQ-UHFFFAOYSA-N [N].C=1C=CNC=1 Chemical group [N].C=1C=CNC=1 MOFINMJRLYEONQ-UHFFFAOYSA-N 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
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- 238000005882 aldol condensation reaction Methods 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 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
- 150000001412 amines Chemical class 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
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- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- QJAPKLJFZAUSKC-UHFFFAOYSA-N dichloro-[[1-(2-dichlorophosphanyloxy-5,6,7,8-tetrahydronaphthalen-1-yl)-5,6,7,8-tetrahydronaphthalen-2-yl]oxy]phosphane Chemical compound C1CCCC2=C1C=CC(OP(Cl)Cl)=C2C1=C2CCCCC2=CC=C1OP(Cl)Cl QJAPKLJFZAUSKC-UHFFFAOYSA-N 0.000 description 1
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- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 238000005120 petroleum cracking Methods 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 238000000066 reactive distillation Methods 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 230000000153 supplemental effect Effects 0.000 description 1
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
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- 239000003039 volatile agent Substances 0.000 description 1
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Classifications
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- 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
- B01J31/185—Phosphites ((RO)3P), their isomeric phosphonates (R(RO)2P=O) and RO-substitution derivatives thereof
- B01J31/186—Mono- or diamide derivatives thereof
-
- 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
- B01J31/1865—Phosphonites (RP(OR)2), their isomeric phosphinates (R2(RO)P=O) and RO-substitution derivatives thereof
- B01J31/187—Amide derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
- C07C45/50—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide by oxo-reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/02—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen
-
- 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)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (3)
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|---|---|---|---|
| EP12382481.5A EP2740535A1 (en) | 2012-12-04 | 2012-12-04 | Bidentate ligands for hydroformylation of ethylene |
| EP12382481.5 | 2012-12-04 | ||
| PCT/US2013/070753 WO2014088800A1 (en) | 2012-12-04 | 2013-11-19 | Bidentate ligands for hydroformylation of ethylene |
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| KR20150092144A KR20150092144A (ko) | 2015-08-12 |
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| CN (2) | CN104822456A (enExample) |
| WO (1) | WO2014088800A1 (enExample) |
| ZA (1) | ZA201503184B (enExample) |
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| KR102291247B1 (ko) | 2013-10-28 | 2021-08-20 | 롬 앤드 하아스 컴패니 | 메타크롤레인을 분리하는 방법 |
| RU2751511C9 (ru) * | 2016-02-11 | 2021-08-18 | Дау Текнолоджи Инвестментс Ллк | Способы превращения олефинов в спирты, простые эфиры или их комбинации |
| RU2619951C1 (ru) * | 2016-06-21 | 2017-05-22 | ФЕДЕРАЛЬНОЕ ГОСУДАРСТВЕННОЕ БЮДЖЕТНОЕ УЧРЕЖДЕНИЕ НАУКИ ИНСТИТУТ ОРГАНИЧЕСКОЙ ХИМИИ им. Н.Д. ЗЕЛИНСКОГО РОССИЙСКОЙ АКАДЕМИИ НАУК (ИОХ РАН) | Двухстадийный способ получения пропионового альдегида |
| TW201840362A (zh) * | 2016-11-08 | 2018-11-16 | 美商陶氏科技投資有限公司 | 使去活化的氫甲醯化催化劑溶液再生的方法 |
| TW201840363A (zh) * | 2016-11-08 | 2018-11-16 | 美商陶氏科技投資有限公司 | 處理氫甲醯化催化劑溶液之方法 |
| TWI758353B (zh) * | 2016-11-08 | 2022-03-21 | 美商陶氏科技投資有限公司 | 使去活化的氫甲醯化催化劑溶液再生的方法 |
| US10183899B2 (en) | 2016-11-10 | 2019-01-22 | Chevron Phillips Chemical Company Lp | Normal alpha olefin synthesis using metathesis and dehydroformylation |
| CN109311002B (zh) * | 2017-05-29 | 2021-12-10 | Lg化学株式会社 | 用于加氢甲酰化反应的催化剂组合物和使用其制备醛的方法 |
| KR102131788B1 (ko) | 2017-05-29 | 2020-07-09 | 주식회사 엘지화학 | 히드로포밀화 반응용 촉매 조성물 및 이를 이용한 알데히드 제조방법 |
| WO2019165350A1 (en) | 2018-02-26 | 2019-08-29 | Bischof Steven M | Normal alpha olefin synthesis using dehydroformylation or dehydroxymethylation |
| US11123723B2 (en) | 2018-02-26 | 2021-09-21 | The Regents Of The University Of California | Oxidative dehydroxymethylation of alcohols to produce olefins |
| CN110327975B (zh) * | 2019-06-06 | 2020-05-19 | 浙江新和成股份有限公司 | 氢甲酰化催化剂及其制备方法和应用 |
| CN113713862B (zh) * | 2020-05-26 | 2023-04-11 | 中国科学院大连化学物理研究所 | 烯烃氢甲酰化反应的Co基多相催化剂及制备和应用 |
| CN116685401B (zh) | 2020-09-25 | 2025-10-03 | 利安德化学技术有限公司 | 在加氢甲酰化中将乙烯与烯丙醇共进料以制备1,4-丁二醇和正丙醇 |
| CN113385236B (zh) * | 2021-06-16 | 2023-02-03 | 上海华谊（集团）公司 | 烯烃氢甲酰化催化剂组合物和氢甲酰化方法 |
| CN115536695B (zh) * | 2021-06-30 | 2025-10-14 | 中国石油化工股份有限公司 | 一种含有聚乙二醇氨基的非对称膦配体及其应用 |
| CN115536697A (zh) * | 2021-06-30 | 2022-12-30 | 中国石油化工股份有限公司 | 膦配体化合物、用于催化氢甲酰化制备醛的催化剂组合物及方法 |
| CN115536698A (zh) * | 2021-06-30 | 2022-12-30 | 中国石油化工股份有限公司 | 膦配体化合物、用于均相氢甲酰化反应的催化剂组合物及方法 |
| CN113583046B (zh) * | 2021-09-02 | 2023-08-25 | 成都欣华源科技有限责任公司 | 双齿膦配体及其制备方法、应用 |
| US12151993B2 (en) | 2021-09-10 | 2024-11-26 | Chevron Phillips Chemical Company Lp | Selective 1-hexene/1-octene production with 1-decene |
| KR20240074844A (ko) | 2021-10-06 | 2024-05-28 | 다우 글로벌 테크놀로지스 엘엘씨 | 프로필이민-작용성 유기규소 화합물 및 1차 아미노프로필-작용성 유기규소 화합물의 제조 |
| CN118019747A (zh) | 2021-10-06 | 2024-05-10 | 陶氏环球技术有限责任公司 | 丙基亚胺官能化有机硅化合物和伯氨基丙基官能化有机硅化合物的制备 |
| CN114163476B (zh) * | 2021-12-02 | 2023-09-19 | 万华化学集团股份有限公司 | 一种单齿膦型配体、氢甲酰化催化剂，一种烯烃氢甲酰化制备线性醛的方法 |
| CN114736239B (zh) * | 2022-05-26 | 2024-01-16 | 重庆理工大学 | 一种双齿膦配体及其制备方法、应用 |
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2013
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- 2013-11-19 US US14/648,803 patent/US9795952B2/en active Active
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- 2013-11-19 WO PCT/US2013/070753 patent/WO2014088800A1/en not_active Ceased
- 2013-11-19 KR KR1020157014700A patent/KR102157915B1/ko active Active
- 2013-11-19 CN CN201811183222.6A patent/CN109364997A/zh active Pending
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| CN109364997A (zh) | 2019-02-22 |
| JP6360067B2 (ja) | 2018-07-18 |
| KR20150092144A (ko) | 2015-08-12 |
| ZA201503184B (en) | 2017-07-26 |
| CN104822456A (zh) | 2015-08-05 |
| WO2014088800A1 (en) | 2014-06-12 |
| US9795952B2 (en) | 2017-10-24 |
| US20150328628A1 (en) | 2015-11-19 |
| JP2016500123A (ja) | 2016-01-07 |
| EP2740535A1 (en) | 2014-06-11 |
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