JPH11506981A - 新規な触媒組成物 - Google Patents
新規な触媒組成物Info
- Publication number
- JPH11506981A JPH11506981A JP9535966A JP53596697A JPH11506981A JP H11506981 A JPH11506981 A JP H11506981A JP 9535966 A JP9535966 A JP 9535966A JP 53596697 A JP53596697 A JP 53596697A JP H11506981 A JPH11506981 A JP H11506981A
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- compound
- catalyst composition
- anisyl
- 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.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 41
- 239000003054 catalyst Substances 0.000 title claims abstract description 30
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 40
- -1 boron hydrocarbyl compound Chemical class 0.000 claims abstract description 36
- 239000003446 ligand Substances 0.000 claims abstract description 34
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims abstract description 22
- 150000001450 anions Chemical class 0.000 claims abstract description 16
- 229910052751 metal Inorganic materials 0.000 claims abstract description 15
- 239000002184 metal Substances 0.000 claims abstract description 15
- 229910052763 palladium Inorganic materials 0.000 claims abstract description 15
- 125000004437 phosphorous atom Chemical group 0.000 claims abstract description 13
- 229910052796 boron Inorganic materials 0.000 claims abstract description 12
- 229920001470 polyketone Polymers 0.000 claims abstract description 12
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims abstract description 11
- 238000004519 manufacturing process Methods 0.000 claims abstract 4
- 150000001875 compounds Chemical class 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 24
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 21
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 20
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 19
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 18
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 14
- 150000001336 alkenes Chemical class 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 230000007935 neutral effect Effects 0.000 claims description 6
- 125000000962 organic group Chemical group 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052698 phosphorus Inorganic materials 0.000 claims description 5
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 239000005977 Ethylene Substances 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- 150000002739 metals Chemical class 0.000 claims description 3
- 239000007848 Bronsted acid Substances 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 239000013028 medium composition Substances 0.000 claims 1
- 229910052754 neon Inorganic materials 0.000 claims 1
- GKAOGPIIYCISHV-UHFFFAOYSA-N neon atom Chemical compound [Ne] GKAOGPIIYCISHV-UHFFFAOYSA-N 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 150000002940 palladium Chemical class 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 29
- 239000002904 solvent Substances 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 150000004820 halides Chemical class 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- 125000004429 atom Chemical group 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 239000007789 gas Substances 0.000 description 7
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 6
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 4
- 239000012041 precatalyst Substances 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- 239000006228 supernatant Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 3
- 239000002841 Lewis acid Substances 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- 150000002736 metal compounds Chemical class 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 3
- 229920001897 terpolymer Polymers 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 239000004711 α-olefin Substances 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 229910002651 NO3 Inorganic materials 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- AIXAANGOTKPUOY-UHFFFAOYSA-N carbachol Chemical group [Cl-].C[N+](C)(C)CCOC(N)=O AIXAANGOTKPUOY-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 150000007517 lewis acids Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 229910052703 rhodium Inorganic materials 0.000 description 2
- 239000010948 rhodium Substances 0.000 description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 2
- 229910052707 ruthenium Inorganic materials 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229910052716 thallium Inorganic materials 0.000 description 2
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 2
- CENMEJUYOOMFFZ-UHFFFAOYSA-N 1,3,2-benzodioxaborole Chemical compound C1=CC=C2OBOC2=C1 CENMEJUYOOMFFZ-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- UQRONKZLYKUEMO-UHFFFAOYSA-N 4-methyl-1-(2,4,6-trimethylphenyl)pent-4-en-2-one Chemical group CC(=C)CC(=O)Cc1c(C)cc(C)cc1C UQRONKZLYKUEMO-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 238000003747 Grignard reaction Methods 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- 229910004713 HPF6 Inorganic materials 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 1
- 241000047703 Nonion Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 229910052770 Uranium Inorganic materials 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- XPEOWXUBQPKDLK-UHFFFAOYSA-N [Li]CC1=CC=CC=C1OC Chemical compound [Li]CC1=CC=CC=C1OC XPEOWXUBQPKDLK-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 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
- 150000003931 anilides Chemical class 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229910000085 borane Inorganic materials 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 150000001767 cationic compounds Chemical class 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 229940120124 dichloroacetate Drugs 0.000 description 1
- 229960005215 dichloroacetic acid Drugs 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 238000005649 metathesis reaction Methods 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002823 nitrates Chemical class 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
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000607 proton-decoupled 31P nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- PNGLEYLFMHGIQO-UHFFFAOYSA-M sodium;3-(n-ethyl-3-methoxyanilino)-2-hydroxypropane-1-sulfonate;dihydrate Chemical compound O.O.[Na+].[O-]S(=O)(=O)CC(O)CN(CC)C1=CC=CC(OC)=C1 PNGLEYLFMHGIQO-UHFFFAOYSA-M 0.000 description 1
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 description 1
- 229940066528 trichloroacetate Drugs 0.000 description 1
- UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G67/00—Macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing oxygen or oxygen and carbon, not provided for in groups C08G2/00 - C08G65/00
- C08G67/02—Copolymers of carbon monoxide and aliphatic unsaturated 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
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
- B01J31/14—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides of aluminium or boron
- B01J31/146—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides of aluminium or boron of boron
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Abstract
Description
Claims (1)
- 【特許請求の範囲】 1.(a)第VIII属金属の供給源、 (b)式: -(N)x-(P)y-N- を有し、式中xが0又は1かつyが0又は1である架橋基により結合された少なく とも2つのリン原子を有する二座ホスフィン配位子、及び、 (c)促進剤、 を共に反応させることにより調製される触媒組成物。 2.架橋基が、式: -(NR2)x-(PR3)y-NR2- を有するものであり、式中各R2は同一又は異なり、R2及びR3は一価の有機基 を示すことを特徴とする請求項1記載の触媒組成物。 3.二座配位子が、式I: を有し、式中R1は独立的にアリール、アルキル、アルコキシ、アミド又はその 置換誘導体であり、R2は水素、ヒドロカルビル又はヘテロ基であり、R3はヒド ロカルビル又はヘテロ基であることを特徴とする請求項1又は2のいずれか一つ の項記載の触媒組成物。 4.x=y=0であることを特徴とする請求項1〜3のいずれか一つの項記載の触 媒組成物。 5.R1基の少なくとも一つがo-アニシル基であることを特徴とする請求項3記 載の触媒組成物。 6.x=y=0であり、かつ全てのR1基がo-アニシル基であることを特徴とする請 求項3記載の触媒組成物。 7.促進剤が、非配位又は弱配位アニオンのいずれかの供給源であることを特徴 と する請求項1〜6のいずれか一つの項記載の触媒組成物。 8.促進剤が、ホウ素ヒドロカルビル化合物であることを特徴とする請求項1〜 6のいずれか一つの項記載の触媒組成物。 9.ホウ素ヒドロカルビル化合物が、式BXYZの化合物であり、式中X、Y及 びZの少なくとも一つが一価のヒドロカルビル基であることを特徴とする請求項 8記載の触媒組成物。 10.式BXYZの化合物が、B(C6F5)3であることを特徴とする請求項9記 載の触媒組成物。 11.式BXYZの化合物が、B(C6H5)3であることを特徴とする請求項9記 載の触媒組成物。 12.促進剤が、複数のホウ素原子を含有するアニオンであることを特徴とする 請求項1〜6のいずれか一つの項記載の触媒組成物。 13.促進剤が、アルミノキサンであることを特徴とする請求項1〜6のいずれ か一つの項記載の触媒組成物。 14.第VIII属金属がパラジウムであることを特徴とする請求項1〜13のいず れか一つの項記載の触媒組成物。 15.請求項1〜14のいずれか一つの項記載の触媒組成物の存在下で、一酸化 炭素と一種以上のオレフィンを接触させることから成るポリケトン類の製造方法 。 16.一酸化炭素をエチレン及びプロピレンと接触させることを特徴とする請求 項15記載のポリケトン類の製造方法。 17.式: (o-アニシル)2PX を有し、式中XはCl、Br又はFであることを特徴とする化合物。 18.XがClであることを特徴とする請求項17記載の化合物。 19.o-アニシルをRがヒドロカルビル基であるR2NPCl2と反応させる第一 工程と、第一工程の生成物をブレンステッド酸で処理する第二工程からなる(o- アニシル)2PClの製造方法。 20.式: (R1)2P-(N)x-(P)y-N-P(R1)2 を有し、式中x及びyは独立的に1又は0であり、R1は請求項3に定義したよ うなものであり、かつR1基の少なくとも一つがo-アニシルであることを特徴と する化合物。 21.式: (R1)2PNR2P(R1)2 を有し、式中R2は水素、ヒドロカルビル又はヘテロ基であることを特徴とする 請求項20に記載の化合物。 22.式: (Ph)2PN(nBu)P(o-アニシル)2 を有することを特徴とする請求項21に記載の化合物。 23.全てのR1基がo-アニシルであることを特徴とする請求項21に記載の化 合物。 24.R2がメチルであることを特徴とする請求項23に記載の化合物。 25.XがCl、Br又はFである(o-アニシル)2PXを、R2が請求項21で定義 したようなものであるNH2R2と、塩基の存在下で反応させることを特徴とする 請求項23に記載の化合物の製造方法。 26.式II: L2Pd(P-P) II を有し、式中各Lは独立的に一座配位子であるか又はL2が共に二座配位子をな し、P-Pは式-(N)x-(P)y-(N)-の架橋基により結合された少なくとも二つの リン原子を有する二座ホスフィン配位子であり、式中x及びyは、x=0かつy=0で ある場合LがClではなく、更にLがClである場合P-Pは(R7)2PN(Me)N( Me)P(R7)2であってR7はアルコキシではないことを条件として1又は0である ことを特徴とする化合物。 27.式III: [L1 2Pd(P-P)](A)2 III を有し、式中P-Pは請求項26に定義されたようなものであり、L1は中性の一 座配 位子であるか又はL1 2が共に中性の二座配位子をなし、かつAは弱又は非配位ア ニオンであるか又は(A)2が共に弱又は非配位ジアニオンをなすことを特徴とす る化合物。
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GBGB9704994.4A GB9704994D0 (en) | 1997-03-11 | 1997-03-11 | Novel catalyst composition |
GB9704994.4 | 1997-03-11 | ||
PCT/GB1997/000963 WO1997037765A1 (en) | 1996-04-04 | 1997-04-04 | Novel catalyst composition |
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JP (1) | JP4027423B2 (ja) |
AU (1) | AU2302797A (ja) |
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2005044444A1 (ja) * | 2003-11-06 | 2005-05-19 | Sumitomo Chemical Company, Limited | オレフィンのオリゴマー化触媒 |
JP2010532711A (ja) * | 2007-07-11 | 2010-10-14 | リンデ アーゲー | エチレンの二、三および/または四量体化のための触媒組成物およびプロセス |
JP2011504799A (ja) * | 2007-11-28 | 2011-02-17 | リンデ アーゲー | エチレンのオリゴマー化のための触媒組成物およびプロセス |
JP2011201918A (ja) * | 1998-08-05 | 2011-10-13 | Sri Internatl | 燐含有化合物、それらの製造方法及びそのための中間体コポリマー化法におけるそれらの使用、並びにそれにより製造されたコポリマー。 |
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---|---|---|---|---|
GB9816550D0 (en) * | 1998-07-29 | 1998-09-30 | Bp Chem Int Ltd | Catalyst composition |
GB9918635D0 (en) * | 1999-08-06 | 1999-10-13 | Bp Chem Int Ltd | Polymerisation process |
GB0016895D0 (en) | 2000-07-11 | 2000-08-30 | Bp Chem Int Ltd | Olefin oligomerisation |
EP1363982A1 (en) | 2001-01-12 | 2003-11-26 | Conocophillips Company | Boron promoted catalysts and fischer-tropsch processes |
US7351845B2 (en) | 2005-02-01 | 2008-04-01 | Exxonmobil Chemical Patents Inc. | Transition metal polymerization catalysts, their synthesis and use in olefin polymerization |
CA2639870A1 (en) * | 2008-09-29 | 2010-03-29 | Nova Chemicals Corporation | Trimerization |
ES2371218T3 (es) | 2009-04-09 | 2011-12-28 | Saudi Basic Industries Corporation | Composición de catalizador y procedimiento para la oligomerización de etileno. |
US9425153B2 (en) | 2013-04-04 | 2016-08-23 | Monolith Semiconductor Inc. | Semiconductor devices comprising getter layers and methods of making and using the same |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS6356524A (ja) * | 1986-08-22 | 1988-03-11 | シエル・インタ−ナシヨネイル・リサ−チ・マ−チヤツピイ・ベ−・ウイ | 新規触媒組成物およびオレフイン/co共重合方法 |
JPS6490222A (en) * | 1987-08-27 | 1989-04-06 | Shell Int Research | Catalyst composition for polymerization of carbon monoxide and olefin |
JPH02189336A (ja) * | 1988-11-11 | 1990-07-25 | Shell Internatl Res Maatschappij Bv | 触媒組成物 |
JPH08269192A (ja) * | 1994-09-15 | 1996-10-15 | Shell Internatl Res Maatschappij Bv | 一酸化炭素とエチレン系不飽和化合物との気相共重合プロセス |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3511048A1 (de) * | 1985-03-27 | 1986-10-02 | Hoechst Ag, 6230 Frankfurt | Traegerkatalysator fuer die herstellung von monocarbonsaeureanhydriden |
FR2629367B1 (fr) * | 1988-03-30 | 1990-11-23 | Norsolor Sa | Systeme catalytique, son procede de preparation et son application a la fabrication d'aldehydes |
WO1992004118A1 (en) * | 1990-08-31 | 1992-03-19 | The Governors Of The University Of Alberta | Carbonylation of methanol using a novel transition metal catalyst precursor |
FR2693190B1 (fr) * | 1992-07-02 | 1994-09-23 | Elf Aquitaine | Procédé d'hydrogénation énantiosélectif de la double liaison C=O OXO. |
GB9517105D0 (en) * | 1995-08-21 | 1995-10-25 | Bp Chem Int Ltd | Catalyst compositions |
-
1997
- 1997-04-04 ES ES97915610T patent/ES2216137T3/es not_active Expired - Lifetime
- 1997-04-04 WO PCT/GB1997/000963 patent/WO1997037765A1/en active IP Right Grant
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- 1997-04-04 EP EP97915610A patent/EP0850105B1/en not_active Expired - Lifetime
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-
1999
- 1999-10-06 US US09/413,261 patent/US6140460A/en not_active Expired - Lifetime
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS6356524A (ja) * | 1986-08-22 | 1988-03-11 | シエル・インタ−ナシヨネイル・リサ−チ・マ−チヤツピイ・ベ−・ウイ | 新規触媒組成物およびオレフイン/co共重合方法 |
JPS6490222A (en) * | 1987-08-27 | 1989-04-06 | Shell Int Research | Catalyst composition for polymerization of carbon monoxide and olefin |
JPH02189336A (ja) * | 1988-11-11 | 1990-07-25 | Shell Internatl Res Maatschappij Bv | 触媒組成物 |
JPH08269192A (ja) * | 1994-09-15 | 1996-10-15 | Shell Internatl Res Maatschappij Bv | 一酸化炭素とエチレン系不飽和化合物との気相共重合プロセス |
Non-Patent Citations (3)
Title |
---|
DONALD F. CLEMENS, ROBERT B. SMITH, JR., JOHN G. DICKINSON: ""Further Studies in the Reactions of Triethylaluminum with Bis(diphenylphosphino)amines"", CANADIAN JOURNAL OF CHEMISTRY, vol. 51(19), JPN4007003165, 1 October 1973 (1973-10-01), CA, pages 3187 - 3189, ISSN: 0000823619 * |
DONALD F. CLEMENS, WILLIAM E. PERKINSON: ""Further Studies in the Rearrangement of Bis(diphenylphosphino)amines upon Chloramination"", INORGANIC CHEMISTRY, vol. 13(2), JPN4007003164, February 1974 (1974-02-01), US, pages 333 - 339, ISSN: 0000823618 * |
LUTZ HEUER, REINHARD SCHMUTZLER: ""A NEW APPROACH TO THE SYNTHESIS OF ARYLDIFLUOROPHOSPHINES. FORMATION OF CIS-DICHLORO-BIS(ARYLDIFLUO", JOURNAL OF FLUORINE CHEMISTRY, vol. 39(2), JPN4007003163, May 1988 (1988-05-01), CH, pages 197 - 216, ISSN: 0000823617 * |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2011201918A (ja) * | 1998-08-05 | 2011-10-13 | Sri Internatl | 燐含有化合物、それらの製造方法及びそのための中間体コポリマー化法におけるそれらの使用、並びにそれにより製造されたコポリマー。 |
WO2005044444A1 (ja) * | 2003-11-06 | 2005-05-19 | Sumitomo Chemical Company, Limited | オレフィンのオリゴマー化触媒 |
JP2010532711A (ja) * | 2007-07-11 | 2010-10-14 | リンデ アーゲー | エチレンの二、三および/または四量体化のための触媒組成物およびプロセス |
JP2011504799A (ja) * | 2007-11-28 | 2011-02-17 | リンデ アーゲー | エチレンのオリゴマー化のための触媒組成物およびプロセス |
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EP0850105A1 (en) | 1998-07-01 |
US6018016A (en) | 2000-01-25 |
DE69727460D1 (de) | 2004-03-11 |
ES2216137T3 (es) | 2004-10-16 |
US6140460A (en) | 2000-10-31 |
DE69727460T2 (de) | 2004-07-01 |
EP0850105B1 (en) | 2004-02-04 |
JP4027423B2 (ja) | 2007-12-26 |
WO1997037765A1 (en) | 1997-10-16 |
AU2302797A (en) | 1997-10-29 |
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