NL8020086A - Fosfine- en fosforniumverbindingen en katalysator. - Google Patents
Fosfine- en fosforniumverbindingen en katalysator. Download PDFInfo
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- NL8020086A NL8020086A NL8020086A NL8020086A NL8020086A NL 8020086 A NL8020086 A NL 8020086A NL 8020086 A NL8020086 A NL 8020086A NL 8020086 A NL8020086 A NL 8020086A NL 8020086 A NL8020086 A NL 8020086A
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- substituted
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- alkyl
- aryl
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 125
- 239000003054 catalyst Substances 0.000 title claims abstract description 100
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 title description 73
- 229910000073 phosphorus hydride Inorganic materials 0.000 title description 37
- 239000003446 ligand Substances 0.000 claims abstract description 156
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 143
- 150000002367 halogens Chemical class 0.000 claims abstract description 134
- 238000000034 method Methods 0.000 claims abstract description 66
- 239000010948 rhodium Substances 0.000 claims abstract description 43
- 229910002091 carbon monoxide Inorganic materials 0.000 claims abstract description 42
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims abstract description 38
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 37
- 239000001257 hydrogen Substances 0.000 claims abstract description 34
- 229910052703 rhodium Inorganic materials 0.000 claims abstract description 32
- 230000008569 process Effects 0.000 claims abstract description 29
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 28
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims abstract description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 156
- 238000006243 chemical reaction Methods 0.000 claims description 132
- 125000004429 atom Chemical group 0.000 claims description 129
- 125000003118 aryl group Chemical group 0.000 claims description 120
- -1 ferrocenyl Chemical group 0.000 claims description 95
- 239000000463 material Substances 0.000 claims description 85
- 239000000203 mixture Substances 0.000 claims description 81
- 150000003624 transition metals Chemical group 0.000 claims description 67
- 125000001153 fluoro group Chemical group F* 0.000 claims description 62
- 125000003342 alkenyl group Chemical group 0.000 claims description 61
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 61
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 60
- 125000005325 aryloxy aryl group Chemical group 0.000 claims description 60
- 125000000304 alkynyl group Chemical group 0.000 claims description 59
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 59
- 229910052698 phosphorus Inorganic materials 0.000 claims description 58
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 57
- 125000004171 alkoxy aryl group Chemical group 0.000 claims description 55
- 229910052723 transition metal Inorganic materials 0.000 claims description 52
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 51
- 229910044991 metal oxide Inorganic materials 0.000 claims description 51
- 150000004706 metal oxides Chemical class 0.000 claims description 51
- 239000002904 solvent Substances 0.000 claims description 48
- 150000003839 salts Chemical group 0.000 claims description 45
- 150000001450 anions Chemical class 0.000 claims description 43
- 229910052785 arsenic Inorganic materials 0.000 claims description 43
- 229910052751 metal Inorganic materials 0.000 claims description 42
- 239000002184 metal Substances 0.000 claims description 42
- 229930195733 hydrocarbon Natural products 0.000 claims description 40
- 150000002430 hydrocarbons Chemical class 0.000 claims description 40
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 39
- 229910001868 water Inorganic materials 0.000 claims description 39
- 230000015572 biosynthetic process Effects 0.000 claims description 29
- 230000003197 catalytic effect Effects 0.000 claims description 28
- 239000000047 product Substances 0.000 claims description 28
- 239000004215 Carbon black (E152) Substances 0.000 claims description 26
- 125000005843 halogen group Chemical group 0.000 claims description 25
- 238000005984 hydrogenation reaction Methods 0.000 claims description 25
- 238000003786 synthesis reaction Methods 0.000 claims description 25
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 23
- 239000000376 reactant Substances 0.000 claims description 23
- 239000007789 gas Substances 0.000 claims description 22
- 239000007787 solid Substances 0.000 claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- 238000006356 dehydrogenation reaction Methods 0.000 claims description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 15
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 15
- 229910052731 fluorine Inorganic materials 0.000 claims description 15
- 229910052742 iron Inorganic materials 0.000 claims description 15
- 150000002739 metals Chemical class 0.000 claims description 15
- 239000010936 titanium Substances 0.000 claims description 14
- 239000004065 semiconductor Substances 0.000 claims description 13
- 229910010413 TiO 2 Inorganic materials 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 12
- 229910004298 SiO 2 Inorganic materials 0.000 claims description 10
- 239000001301 oxygen Substances 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 229910052697 platinum Inorganic materials 0.000 claims description 10
- 229910052707 ruthenium Inorganic materials 0.000 claims description 10
- 229910052719 titanium Inorganic materials 0.000 claims description 10
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 9
- 238000007323 disproportionation reaction Methods 0.000 claims description 9
- 125000002091 cationic group Chemical group 0.000 claims description 8
- 229910017052 cobalt Inorganic materials 0.000 claims description 8
- 239000010941 cobalt Substances 0.000 claims description 8
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 8
- 239000011737 fluorine Substances 0.000 claims description 8
- 229910052759 nickel Inorganic materials 0.000 claims description 8
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 claims description 7
- 239000007795 chemical reaction product Substances 0.000 claims description 6
- 239000006184 cosolvent Substances 0.000 claims description 6
- 229910052710 silicon Inorganic materials 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 229910052741 iridium Inorganic materials 0.000 claims description 5
- 239000002243 precursor Substances 0.000 claims description 5
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 4
- 229910052770 Uranium Inorganic materials 0.000 claims description 4
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052753 mercury Inorganic materials 0.000 claims description 4
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 3
- 229910006404 SnO 2 Inorganic materials 0.000 claims description 3
- 229910052750 molybdenum Inorganic materials 0.000 claims description 3
- 239000011733 molybdenum Substances 0.000 claims description 3
- 125000004437 phosphorous atom Chemical group 0.000 claims description 3
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- 239000010937 tungsten Substances 0.000 claims description 3
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
- 229910014568 C—O-M Inorganic materials 0.000 claims description 2
- 229910013504 M-O-M Inorganic materials 0.000 claims description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 2
- 229910052804 chromium Inorganic materials 0.000 claims description 2
- 239000011651 chromium Substances 0.000 claims description 2
- 239000010949 copper Substances 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052737 gold Inorganic materials 0.000 claims description 2
- 239000010931 gold Substances 0.000 claims description 2
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 229910052762 osmium Inorganic materials 0.000 claims description 2
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 229910052702 rhenium Inorganic materials 0.000 claims description 2
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 claims description 2
- 229910052709 silver Inorganic materials 0.000 claims description 2
- 239000004332 silver Substances 0.000 claims description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims 12
- 229910002092 carbon dioxide Inorganic materials 0.000 claims 6
- GEIAQOFPUVMAGM-UHFFFAOYSA-N ZrO Inorganic materials [Zr]=O GEIAQOFPUVMAGM-UHFFFAOYSA-N 0.000 claims 2
- 239000001569 carbon dioxide Substances 0.000 claims 2
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 229910003080 TiO4 Inorganic materials 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 230000001419 dependent effect Effects 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 229910052909 inorganic silicate Inorganic materials 0.000 claims 1
- 108090000623 proteins and genes Proteins 0.000 claims 1
- 238000007037 hydroformylation reaction Methods 0.000 abstract description 11
- 229910052799 carbon Inorganic materials 0.000 abstract description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 5
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- 239000007983 Tris buffer Substances 0.000 description 62
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 45
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 44
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- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 36
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical class CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 17
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- HZHUAESPXGNNFV-UHFFFAOYSA-N diethyl(methyl)phosphane Chemical compound CCP(C)CC HZHUAESPXGNNFV-UHFFFAOYSA-N 0.000 description 16
- 239000007858 starting material Substances 0.000 description 16
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 15
- 238000012360 testing method Methods 0.000 description 14
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 12
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 11
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- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 10
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- 101100329225 Coprinopsis cinerea (strain Okayama-7 / 130 / ATCC MYA-4618 / FGSC 9003) cpf2 gene Proteins 0.000 description 8
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- RKTYLMNFRDHKIL-UHFFFAOYSA-N copper;5,10,15,20-tetraphenylporphyrin-22,24-diide Chemical compound [Cu+2].C1=CC(C(=C2C=CC([N-]2)=C(C=2C=CC=CC=2)C=2C=CC(N=2)=C(C=2C=CC=CC=2)C2=CC=C3[N-]2)C=2C=CC=CC=2)=NC1=C3C1=CC=CC=C1 RKTYLMNFRDHKIL-UHFFFAOYSA-N 0.000 description 3
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- RISKOGXRBTXEAF-UHFFFAOYSA-N benzhydryl(2-diphenylphosphanylethynyl)phosphanium;methanesulfonate Chemical compound CS([O-])(=O)=O.C=1C=CC=CC=1C(C=1C=CC=CC=1)[PH2+]C#CP(C=1C=CC=CC=1)C1=CC=CC=C1 RISKOGXRBTXEAF-UHFFFAOYSA-N 0.000 description 1
- QPYHTMDEIMBZNA-UHFFFAOYSA-N benzhydryl(6-diphenylphosphanylhexyl)phosphanium;methanesulfonate Chemical compound CS([O-])(=O)=O.C=1C=CC=CC=1C(C=1C=CC=CC=1)[PH2+]CCCCCCP(C=1C=CC=CC=1)C1=CC=CC=C1 QPYHTMDEIMBZNA-UHFFFAOYSA-N 0.000 description 1
- CBIRGUXNMJNWHU-UHFFFAOYSA-N benzhydryl-tris(2-difluorophosphanylethynyl)phosphanium Chemical compound C=1C=CC=CC=1C([P+](C#CP(F)F)(C#CP(F)F)C#CP(F)F)C1=CC=CC=C1 CBIRGUXNMJNWHU-UHFFFAOYSA-N 0.000 description 1
- DSEKCAGYDDBBFC-UHFFFAOYSA-N benzhydryl-tris(2-diphenylphosphanylethyl)phosphanium Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CC[P+](C(C=1C=CC=CC=1)C=1C=CC=CC=1)(CCP(C=1C=CC=CC=1)C=1C=CC=CC=1)CCP(C=1C=CC=CC=1)C1=CC=CC=C1 DSEKCAGYDDBBFC-UHFFFAOYSA-N 0.000 description 1
- GYQZUKJZAAQNFK-UHFFFAOYSA-N benzhydrylphosphanium;ethynyl(difluoro)phosphane;methanesulfonate Chemical compound CS([O-])(=O)=O.FP(F)C#C.C=1C=CC=CC=1C([PH3+])C1=CC=CC=C1 GYQZUKJZAAQNFK-UHFFFAOYSA-N 0.000 description 1
- COEOHTGKMIANMJ-UHFFFAOYSA-N benzhydrylphosphanium;ethynyl(diphenyl)phosphane;methanesulfonate Chemical compound CS([O-])(=O)=O.C=1C=CC=CC=1C([PH3+])C1=CC=CC=C1.C=1C=CC=CC=1P(C#C)C1=CC=CC=C1 COEOHTGKMIANMJ-UHFFFAOYSA-N 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- JOKYYJPVAFRMIT-UHFFFAOYSA-N benzyl benzenesulfonate Chemical compound C=1C=CC=CC=1S(=O)(=O)OCC1=CC=CC=C1 JOKYYJPVAFRMIT-UHFFFAOYSA-N 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- ZDKRMIJRCHPKLW-UHFFFAOYSA-N benzyl methanesulfonate Chemical compound CS(=O)(=O)OCC1=CC=CC=C1 ZDKRMIJRCHPKLW-UHFFFAOYSA-N 0.000 description 1
- LCNVONJIKCVRBD-UHFFFAOYSA-N bis(2-chloroethyl)phosphane Chemical compound ClCCPCCCl LCNVONJIKCVRBD-UHFFFAOYSA-N 0.000 description 1
- KFYYIVKNCLOSDX-UHFFFAOYSA-M bis(2-diphenylphosphanylethyl)-methyl-phenylphosphanium;methanesulfonate Chemical compound CS([O-])(=O)=O.C=1C=CC=CC=1P(C=1C=CC=CC=1)CC[P+](C=1C=CC=CC=1)(C)CCP(C=1C=CC=CC=1)C1=CC=CC=C1 KFYYIVKNCLOSDX-UHFFFAOYSA-M 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- IEFORYAKGBSZCQ-UHFFFAOYSA-N butoxy(oxo)borane Chemical group CCCCOB=O IEFORYAKGBSZCQ-UHFFFAOYSA-N 0.000 description 1
- LFLBHTZRLVHUQC-UHFFFAOYSA-N butyl methanesulfonate Chemical compound CCCCOS(C)(=O)=O LFLBHTZRLVHUQC-UHFFFAOYSA-N 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 229910002090 carbon oxide Inorganic materials 0.000 description 1
- 230000006315 carbonylation Effects 0.000 description 1
- 238000005810 carbonylation reaction Methods 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 239000012018 catalyst precursor Substances 0.000 description 1
- 150000001768 cations Chemical group 0.000 description 1
- 230000009920 chelation Effects 0.000 description 1
- CRKDVBVOAIRDNW-LWSMPMPHSA-N chembl600981 Chemical compound C12=CC(OC)=C(OC)C=C2N[C@]2(O3)[C@@H]4C[C@@H]5[C@@H](C(=O)OC)[C@]12C[C@H]3N4C\C5=C\C CRKDVBVOAIRDNW-LWSMPMPHSA-N 0.000 description 1
- 238000007385 chemical modification Methods 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 239000011365 complex material Substances 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- UVJHQYIOXKWHFD-UHFFFAOYSA-N cyclohexa-1,4-diene Chemical compound C1C=CCC=C1 UVJHQYIOXKWHFD-UHFFFAOYSA-N 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- PTLIZOFGXLGHSY-UHFFFAOYSA-N dibutylphosphane Chemical compound CCCCPCCCC PTLIZOFGXLGHSY-UHFFFAOYSA-N 0.000 description 1
- 125000004989 dicarbonyl group Chemical group 0.000 description 1
- ZCAYTKRHHNTJOG-UHFFFAOYSA-N dichloro(2-diethylphosphanylethynyl)phosphane Chemical compound CCP(CC)C#CP(Cl)Cl ZCAYTKRHHNTJOG-UHFFFAOYSA-N 0.000 description 1
- PROJSORBSRYJBL-UHFFFAOYSA-N dichloro(2-diphenylphosphanylethynyl)phosphane Chemical compound C=1C=CC=CC=1P(C#CP(Cl)Cl)C1=CC=CC=C1 PROJSORBSRYJBL-UHFFFAOYSA-N 0.000 description 1
- WIDHEDUSAKJSPO-UHFFFAOYSA-L dichloro-bis(oxomethylidene)ruthenium Chemical compound [O+]#[C-].[O+]#[C-].Cl[Ru]Cl WIDHEDUSAKJSPO-UHFFFAOYSA-L 0.000 description 1
- LWNLXVXSCCLRRZ-UHFFFAOYSA-N dichlorophosphane Chemical class ClPCl LWNLXVXSCCLRRZ-UHFFFAOYSA-N 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- DPFCRMGFCUKIJZ-UHFFFAOYSA-N difluoro(phenyl)phosphane Chemical compound FP(F)C1=CC=CC=C1 DPFCRMGFCUKIJZ-UHFFFAOYSA-N 0.000 description 1
- OKZIUSOJQLYFSE-UHFFFAOYSA-N difluoroboron Chemical compound F[B]F OKZIUSOJQLYFSE-UHFFFAOYSA-N 0.000 description 1
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- YGJLJUSRBRCZMM-UHFFFAOYSA-N diphenyl-[2-[2,3,4-tris(2-diphenylphosphanylethyl)-5-[phenyl(phosphanyl)methyl]phenyl]ethyl]phosphane Chemical compound C1=CC=C(C=C1)C(C2=C(C(=C(C(=C2)CCP(C3=CC=CC=C3)C4=CC=CC=C4)CCP(C5=CC=CC=C5)C6=CC=CC=C6)CCP(C7=CC=CC=C7)C8=CC=CC=C8)CCP(C9=CC=CC=C9)C1=CC=CC=C1)P YGJLJUSRBRCZMM-UHFFFAOYSA-N 0.000 description 1
- WAJKHNTVDCZXPH-UHFFFAOYSA-N disodium acetylide Chemical class [Na+].[Na+].[C-]#[C-] WAJKHNTVDCZXPH-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000005868 electrolysis reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- XRINTCBCHUYEDP-UHFFFAOYSA-N ethynyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(C#C)C1=CC=CC=C1 XRINTCBCHUYEDP-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- FIMAYKDZLLQUDW-UHFFFAOYSA-N fluoro(dioxido)borane;trimethyloxidanium Chemical compound C[O+](C)C.C[O+](C)C.[O-]B([O-])F FIMAYKDZLLQUDW-UHFFFAOYSA-N 0.000 description 1
- GDFIJNGQTASLHK-UHFFFAOYSA-N fluoro-bis[2-(2,3,4,5,6-pentafluorophenyl)ethynyl]phosphane Chemical compound FC=1C(F)=C(F)C(F)=C(F)C=1C#CP(F)C#CC1=C(F)C(F)=C(F)C(F)=C1F GDFIJNGQTASLHK-UHFFFAOYSA-N 0.000 description 1
- 235000019256 formaldehyde Nutrition 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
- 229940119177 germanium dioxide Drugs 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 229910052735 hafnium Inorganic materials 0.000 description 1
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 description 1
- WIHZLLGSGQNAGK-UHFFFAOYSA-N hafnium(4+);oxygen(2-) Chemical class [O-2].[O-2].[Hf+4] WIHZLLGSGQNAGK-UHFFFAOYSA-N 0.000 description 1
- CJNBYAVZURUTKZ-UHFFFAOYSA-N hafnium(IV) oxide Inorganic materials O=[Hf]=O CJNBYAVZURUTKZ-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000002638 heterogeneous catalyst Substances 0.000 description 1
- 238000007172 homogeneous catalysis Methods 0.000 description 1
- 239000002815 homogeneous catalyst Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 229910001410 inorganic ion Inorganic materials 0.000 description 1
- 229910003480 inorganic solid Inorganic materials 0.000 description 1
- 239000012212 insulator Substances 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- QZLVALRWETVYSE-UHFFFAOYSA-N iron;trifluoromethanesulfonic acid Chemical compound [Fe].OS(=O)(=O)C(F)(F)F QZLVALRWETVYSE-UHFFFAOYSA-N 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- PYFPOCHADKJAJZ-UHFFFAOYSA-N methanesulfonate;methylphosphanium Chemical compound [PH3+]C.CS([O-])(=O)=O PYFPOCHADKJAJZ-UHFFFAOYSA-N 0.000 description 1
- ZUWCLKMYRYFYDN-UHFFFAOYSA-M methanesulfonate;tris(2-diphenylphosphanylethyl)-(3-methylbutyl)phosphanium Chemical compound CS([O-])(=O)=O.C=1C=CC=CC=1P(C=1C=CC=CC=1)CC[P+](CCP(C=1C=CC=CC=1)C=1C=CC=CC=1)(CCC(C)C)CCP(C=1C=CC=CC=1)C1=CC=CC=C1 ZUWCLKMYRYFYDN-UHFFFAOYSA-M 0.000 description 1
- DRECBBFIAREDAS-UHFFFAOYSA-N methoxymethane;hydrate Chemical compound O.COC DRECBBFIAREDAS-UHFFFAOYSA-N 0.000 description 1
- UKWRSCMHHKKVCV-UHFFFAOYSA-N methylphosphanium;trifluoromethanesulfonate Chemical compound [PH3+]C.[O-]S(=O)(=O)C(F)(F)F UKWRSCMHHKKVCV-UHFFFAOYSA-N 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- SFDZETWZUCDYMD-UHFFFAOYSA-N monosodium acetylide Chemical compound [Na+].[C-]#C SFDZETWZUCDYMD-UHFFFAOYSA-N 0.000 description 1
- BEDTYJZWCGTAME-UHFFFAOYSA-N n-tert-butyl-n-[2-[fluoro(2-phenoxyethyl)arsanyl]ethynyl]-2-methylpropan-2-amine Chemical compound CC(C)(C)N(C(C)(C)C)C#C[As](F)CCOC1=CC=CC=C1 BEDTYJZWCGTAME-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- CRKDVBVOAIRDNW-WZUFQYTHSA-N norquaternine Natural products COC(=O)C1C2CC3N(C/C/2=C/C)C4CC15c6cc(OC)c(OC)cc6NC35O4 CRKDVBVOAIRDNW-WZUFQYTHSA-N 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- VSYYDIKSLHPSDQ-UHFFFAOYSA-N octane-1,8-disulfonic acid Chemical compound OS(=O)(=O)CCCCCCCCS(O)(=O)=O VSYYDIKSLHPSDQ-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- GNPXKHTZVDUNOY-UHFFFAOYSA-N oxomethylidenerhodium Chemical compound O=C=[Rh] GNPXKHTZVDUNOY-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- RUVINXPYWBROJD-UHFFFAOYSA-N para-methoxyphenyl Natural products COC1=CC=C(C=CC)C=C1 RUVINXPYWBROJD-UHFFFAOYSA-N 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 150000004707 phenolate Chemical class 0.000 description 1
- YSWYYGKGAYSAOJ-UHFFFAOYSA-N phosphane Chemical compound P.P YSWYYGKGAYSAOJ-UHFFFAOYSA-N 0.000 description 1
- PMOIAJVKYNVHQE-UHFFFAOYSA-N phosphanium;bromide Chemical compound [PH4+].[Br-] PMOIAJVKYNVHQE-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003009 phosphonic acids Chemical class 0.000 description 1
- 125000005496 phosphonium group Chemical group 0.000 description 1
- OAICVXFJPJFONN-BJUDXGSMSA-N phosphorus-30 Chemical compound [30P] OAICVXFJPJFONN-BJUDXGSMSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 235000019260 propionic acid Nutrition 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
- 230000009257 reactivity Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- QPILZZVXGUNELN-UHFFFAOYSA-M sodium;4-amino-5-hydroxynaphthalene-2,7-disulfonate;hydron Chemical compound [Na+].OS(=O)(=O)C1=CC(O)=C2C(N)=CC(S([O-])(=O)=O)=CC2=C1 QPILZZVXGUNELN-UHFFFAOYSA-M 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- QDNCLIPKBNMUPP-UHFFFAOYSA-N trimethyloxidanium Chemical compound C[O+](C)C QDNCLIPKBNMUPP-UHFFFAOYSA-N 0.000 description 1
- NRZWQKGABZFFKE-UHFFFAOYSA-N trimethylsulfonium Chemical compound C[S+](C)C NRZWQKGABZFFKE-UHFFFAOYSA-N 0.000 description 1
- RIOQSEWOXXDEQQ-UHFFFAOYSA-O triphenylphosphanium Chemical compound C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-O 0.000 description 1
- ZFEAYIKULRXTAR-UHFFFAOYSA-M triphenylsulfanium;chloride Chemical class [Cl-].C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 ZFEAYIKULRXTAR-UHFFFAOYSA-M 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- GQXKPURVRKKSEM-UHFFFAOYSA-N tris(2-diethylphosphanylethyl)-methylphosphanium Chemical compound CCP(CC)CC[P+](C)(CCP(CC)CC)CCP(CC)CC GQXKPURVRKKSEM-UHFFFAOYSA-N 0.000 description 1
- QWUDONPHGLTBJN-UHFFFAOYSA-N tris(2-diethylphosphanylethynyl)phosphane Chemical compound CCP(CC)C#CP(C#CP(CC)CC)C#CP(CC)CC QWUDONPHGLTBJN-UHFFFAOYSA-N 0.000 description 1
- PWHVMOYZCLMRLX-UHFFFAOYSA-N tris(2-diphenylphosphanylethynyl)phosphane Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C#CP(C#CP(C=1C=CC=CC=1)C=1C=CC=CC=1)C#CP(C=1C=CC=CC=1)C1=CC=CC=C1 PWHVMOYZCLMRLX-UHFFFAOYSA-N 0.000 description 1
- NCMCQXTXQDKSCZ-UHFFFAOYSA-N tris(3,3,3-trifluoroprop-1-ynyl)phosphane Chemical compound FC(F)(F)C#CP(C#CC(F)(F)F)C#CC(F)(F)F NCMCQXTXQDKSCZ-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/06—Cobalt compounds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/1608—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes the ligands containing silicon
-
- 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
- B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
- B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
-
- 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
-
- 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
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/62—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by hydrogenation of carbon-to-carbon double or triple bonds
-
- 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
- C07C45/74—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration
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- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
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- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0073—Rhodium compounds
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- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/02—Iron compounds
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/5004—Acyclic saturated phosphines
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/5013—Acyclic unsaturated phosphines
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/5027—Polyphosphines
-
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/54—Quaternary phosphonium compounds
- C07F9/5407—Acyclic saturated phosphonium compounds
- C07F9/5414—Acyclic saturated phosphonium compounds substituted by B, Si, P or a metal
- C07F9/5421—Acyclic saturated phosphonium compounds substituted by B, Si, P or a metal substituted by a phosphorus atom
-
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/54—Quaternary phosphonium compounds
- C07F9/5428—Acyclic unsaturated phosphonium compounds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- 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
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Applications Claiming Priority (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US06/011,238 US4298541A (en) | 1979-02-12 | 1979-02-12 | Trihydrocarbyl silyl-substituted alkyl diaryl phosphine transition metal complexes and their use as homogeneous catalysts |
US1123879 | 1979-02-12 | ||
US4354879A | 1979-05-29 | 1979-05-29 | |
US4354879 | 1979-05-29 | ||
US11462780 | 1980-01-23 | ||
US06/114,627 US4302401A (en) | 1980-01-23 | 1980-01-23 | Tetraalkyl phosphonium substituted phosphine and amine transition metal complexes |
Publications (1)
Publication Number | Publication Date |
---|---|
NL8020086A true NL8020086A (nl) | 1980-12-31 |
Family
ID=27359388
Family Applications (4)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NL8020086A NL8020086A (nl) | 1979-02-12 | 1980-02-12 | Fosfine- en fosforniumverbindingen en katalysator. |
NL8020079A NL8020079A (nl) | 1979-02-12 | 1980-02-12 | Werkwijze ter bereiding van aldehyden. |
NL8020087A NL8020087A (nl) | 1979-02-12 | 1980-02-12 | Carbonyleringswerkwijze en nieuwe overgangs- metaalkatalysatoren. |
NL8020088A NL8020088A (nl) | 1979-02-12 | 1980-02-12 | Tetraaelkylfosfonium-gesubstitueerde overgangsmetaal- complexen. |
Family Applications After (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NL8020079A NL8020079A (nl) | 1979-02-12 | 1980-02-12 | Werkwijze ter bereiding van aldehyden. |
NL8020087A NL8020087A (nl) | 1979-02-12 | 1980-02-12 | Carbonyleringswerkwijze en nieuwe overgangs- metaalkatalysatoren. |
NL8020088A NL8020088A (nl) | 1979-02-12 | 1980-02-12 | Tetraaelkylfosfonium-gesubstitueerde overgangsmetaal- complexen. |
Country Status (8)
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US3954821A (en) * | 1975-06-30 | 1976-05-04 | E. I. Du Pont De Nemours And Company | Carbon dioxide complexes of Rh, Ir, Ni, Pd, and Pt |
US4136103A (en) * | 1975-12-29 | 1979-01-23 | Exxon Research & Engineering Co. | Substituted tetraalkyl phosphonium aluminosilicates |
US4138420A (en) * | 1976-01-19 | 1979-02-06 | Celanese Corporation | Hydroformylation catalysts |
US4193943A (en) * | 1976-01-19 | 1980-03-18 | Celanese Corporation | Hydroformylation catalysts |
US4247486A (en) * | 1977-03-11 | 1981-01-27 | Union Carbide Corporation | Cyclic hydroformylation process |
US4089881A (en) * | 1976-11-12 | 1978-05-16 | Vanderbilt University | Complexes of metallated coordination ligands |
US4144191A (en) * | 1977-06-06 | 1979-03-13 | The Dow Chemical Company | Amine-resin supported rhodium-cobalt carbonyl bimetallic clusters as novel hydroformylation catalysts |
US4152344A (en) * | 1977-08-08 | 1979-05-01 | Celanese Corporation | Phosphino-ferrocene ligands |
US4201714A (en) * | 1977-08-19 | 1980-05-06 | Celanese Corporation | Stabilized catalyst complex of rhodium metal, bidentate ligand and monodentate ligand |
US4169861A (en) * | 1977-08-19 | 1979-10-02 | Celanese Corporation | Hydroformylation process |
US4179403A (en) * | 1977-12-19 | 1979-12-18 | Shell Oil Company | Resin-ligand-metal complex compositions |
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1980
- 1980-02-12 BR BR8006679A patent/BR8006679A/pt unknown
- 1980-02-12 JP JP55500652A patent/JPS6332079B2/ja not_active Expired
- 1980-02-12 NL NL8020086A patent/NL8020086A/nl not_active Application Discontinuation
- 1980-02-12 EP EP82107978A patent/EP0071281B1/en not_active Expired
- 1980-02-12 WO PCT/US1980/000216 patent/WO1980001691A1/en active Application Filing
- 1980-02-12 NL NL8020079A patent/NL8020079A/nl not_active Application Discontinuation
- 1980-02-12 NL NL8020087A patent/NL8020087A/nl not_active Application Discontinuation
- 1980-02-12 GB GB8031136A patent/GB2086906B/en not_active Expired
- 1980-02-12 DE DE803034354T patent/DE3034354A1/de not_active Ceased
- 1980-02-12 JP JP50065180A patent/JPS56500167A/ja active Pending
- 1980-02-12 WO PCT/US1980/000215 patent/WO1980001692A1/en active IP Right Grant
- 1980-02-12 JP JP50065080A patent/JPS55501178A/ja active Pending
- 1980-02-12 DE DE803034353T patent/DE3034353A1/de not_active Withdrawn
- 1980-02-12 BR BR8006681A patent/BR8006681A/pt unknown
- 1980-02-12 NL NL8020088A patent/NL8020088A/nl not_active Application Discontinuation
- 1980-02-12 WO PCT/US1980/000212 patent/WO1980001689A1/en active IP Right Grant
- 1980-02-12 GB GB8031135A patent/GB2057906B/en not_active Expired
- 1980-02-12 GB GB8031137A patent/GB2056989B/en not_active Expired
- 1980-02-12 DE DE803034352T patent/DE3034352A1/de not_active Withdrawn
- 1980-02-12 WO PCT/US1980/000213 patent/WO1980001690A1/en active IP Right Grant
- 1980-02-12 EP EP85100028A patent/EP0159460A1/en not_active Withdrawn
- 1980-02-12 BR BR8006680A patent/BR8006680A/pt unknown
- 1980-02-12 DE DE803034351T patent/DE3034351A1/de not_active Ceased
- 1980-08-25 EP EP80900539A patent/EP0023923B1/en not_active Expired
- 1980-08-25 EP EP80900484A patent/EP0024088A1/en not_active Withdrawn
- 1980-08-25 EP EP80900541A patent/EP0023924B1/en not_active Expired
- 1980-08-25 EP EP80900540A patent/EP0024091B1/en not_active Expired
- 1980-10-09 SE SE8007079A patent/SE8007079L/xx not_active Application Discontinuation
- 1980-10-09 SE SE8007080A patent/SE439439B/sv not_active IP Right Cessation
- 1980-10-10 SE SE8007140A patent/SE449093B/sv not_active IP Right Cessation
- 1980-10-10 SE SE8007139A patent/SE449750B/sv not_active IP Right Cessation
-
1982
- 1982-01-22 SE SE8200371A patent/SE8200371L/xx not_active Application Discontinuation
- 1982-07-23 SE SE8204443A patent/SE8204443D0/xx not_active Application Discontinuation
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