WO2004046209A1 - Catalyseurs de metal de transition pour produire des polyvinylesters - Google Patents
Catalyseurs de metal de transition pour produire des polyvinylesters Download PDFInfo
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- WO2004046209A1 WO2004046209A1 PCT/EP2003/012538 EP0312538W WO2004046209A1 WO 2004046209 A1 WO2004046209 A1 WO 2004046209A1 EP 0312538 W EP0312538 W EP 0312538W WO 2004046209 A1 WO2004046209 A1 WO 2004046209A1
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- 239000003054 catalyst Substances 0.000 title claims abstract description 28
- 229920001290 polyvinyl ester Polymers 0.000 title claims description 9
- 229910052723 transition metal Inorganic materials 0.000 title claims description 5
- 150000003624 transition metals Chemical class 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 29
- 238000000034 method Methods 0.000 claims abstract description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
- 239000010936 titanium Substances 0.000 claims description 11
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 229910052698 phosphorus Inorganic materials 0.000 claims description 9
- 239000011574 phosphorus Substances 0.000 claims description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
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- 125000004122 cyclic group Chemical group 0.000 claims description 7
- 230000000737 periodic effect Effects 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 239000003446 ligand Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 4
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- 150000004646 arylidenes Chemical group 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
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- 229910052749 magnesium Inorganic materials 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
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- 239000010703 silicon Substances 0.000 claims description 4
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- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 8
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- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
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- 125000004104 aryloxy group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 150000003935 benzaldehydes Chemical class 0.000 description 1
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- ZDZHCHYQNPQSGG-UHFFFAOYSA-N binaphthyl group Chemical group C1(=CC=CC2=CC=CC=C12)C1=CC=CC2=CC=CC=C12 ZDZHCHYQNPQSGG-UHFFFAOYSA-N 0.000 description 1
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- BPOZNMOEPOHHSC-UHFFFAOYSA-N butyl prop-2-enoate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCCCOC(=O)C=C BPOZNMOEPOHHSC-UHFFFAOYSA-N 0.000 description 1
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 235000013351 cheese Nutrition 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229960001701 chloroform Drugs 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000522 cyclooctenyl group Chemical group C1(=CCCCCCC1)* 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- GDVKFRBCXAPAQJ-UHFFFAOYSA-A dialuminum;hexamagnesium;carbonate;hexadecahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Al+3].[Al+3].[O-]C([O-])=O GDVKFRBCXAPAQJ-UHFFFAOYSA-A 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- YCUBDDIKWLELPD-UHFFFAOYSA-N ethenyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OC=C YCUBDDIKWLELPD-UHFFFAOYSA-N 0.000 description 1
- GLVVKKSPKXTQRB-UHFFFAOYSA-N ethenyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OC=C GLVVKKSPKXTQRB-UHFFFAOYSA-N 0.000 description 1
- GFJVXXWOPWLRNU-UHFFFAOYSA-N ethenyl formate Chemical compound C=COC=O GFJVXXWOPWLRNU-UHFFFAOYSA-N 0.000 description 1
- LZWYWAIOTBEZFN-UHFFFAOYSA-N ethenyl hexanoate Chemical compound CCCCCC(=O)OC=C LZWYWAIOTBEZFN-UHFFFAOYSA-N 0.000 description 1
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 125000003106 haloaryl group Chemical group 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 125000005980 hexynyl group Chemical group 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
- 229960001545 hydrotalcite Drugs 0.000 description 1
- 229910001701 hydrotalcite Inorganic materials 0.000 description 1
- 150000002466 imines Chemical group 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- AZVCGYPLLBEUNV-UHFFFAOYSA-N lithium;ethanolate Chemical compound [Li+].CC[O-] AZVCGYPLLBEUNV-UHFFFAOYSA-N 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 125000005069 octynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000002899 organoaluminium compounds Chemical class 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 229920006280 packaging film Polymers 0.000 description 1
- 239000012785 packaging film Substances 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 description 1
- 229920006112 polar polymer Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920002959 polymer blend Polymers 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 235000013580 sausages Nutrition 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 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
- 238000003756 stirring Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000010414 supernatant solution Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- XBFJAVXCNXDMBH-UHFFFAOYSA-N tetracyclo[6.2.1.1(3,6).0(2,7)]dodec-4-ene Chemical compound C1C(C23)C=CC1C3C1CC2CC1 XBFJAVXCNXDMBH-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- SQBBHCOIQXKPHL-UHFFFAOYSA-N tributylalumane Chemical compound CCCC[Al](CCCC)CCCC SQBBHCOIQXKPHL-UHFFFAOYSA-N 0.000 description 1
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 1
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 1
- MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical compound C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-UHFFFAOYSA-N 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- YFDAMRSZJLWUSQ-UHFFFAOYSA-N tris(2-methylphenyl)borane Chemical compound CC1=CC=CC=C1B(C=1C(=CC=CC=1)C)C1=CC=CC=C1C YFDAMRSZJLWUSQ-UHFFFAOYSA-N 0.000 description 1
- LKNHGIFPRLUGEG-UHFFFAOYSA-N tris(3,4,5-trifluorophenyl)borane Chemical compound FC1=C(F)C(F)=CC(B(C=2C=C(F)C(F)=C(F)C=2)C=2C=C(F)C(F)=C(F)C=2)=C1 LKNHGIFPRLUGEG-UHFFFAOYSA-N 0.000 description 1
- OHSAEOPCBBOWPU-UHFFFAOYSA-N tris(3,5-dimethylphenyl)borane Chemical compound CC1=CC(C)=CC(B(C=2C=C(C)C=C(C)C=2)C=2C=C(C)C=C(C)C=2)=C1 OHSAEOPCBBOWPU-UHFFFAOYSA-N 0.000 description 1
- YPVVTWIAXFPZLS-UHFFFAOYSA-N tris(4-fluorophenyl)borane Chemical compound C1=CC(F)=CC=C1B(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 YPVVTWIAXFPZLS-UHFFFAOYSA-N 0.000 description 1
- OBAJXDYVZBHCGT-UHFFFAOYSA-N tris(pentafluorophenyl)borane Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1B(C=1C(=C(F)C(F)=C(F)C=1F)F)C1=C(F)C(F)=C(F)C(F)=C1F OBAJXDYVZBHCGT-UHFFFAOYSA-N 0.000 description 1
- OSMBUUFIZBTSNO-UHFFFAOYSA-N tris[4-(fluoromethyl)phenyl]borane Chemical compound C1=CC(CF)=CC=C1B(C=1C=CC(CF)=CC=1)C1=CC=C(CF)C=C1 OSMBUUFIZBTSNO-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 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
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/006—Palladium compounds
- C07F15/0066—Palladium compounds without a metal-carbon linkage
-
- 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
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/006—Palladium compounds
-
- 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
- C07F15/04—Nickel compounds
-
- 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
- C07F15/04—Nickel compounds
- C07F15/045—Nickel compounds without a metal-carbon linkage
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F18/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid or of a haloformic acid
- C08F18/02—Esters of monocarboxylic acids
- C08F18/04—Vinyl esters
Definitions
- Transition metal catalysts for the production of polyvinyl esters are Transition metal catalysts for the production of polyvinyl esters
- the present invention relates to catalysts for polymerization
- Copolymerization of vinyl esters and a process for the polymerization and copolymerization of vinyl esters.
- Vinyl esters are olefinic compounds with the following basic structure.
- Polyvinyl esters are polymers accessible from vinyl esters by olefinic polymerization, of which the polyvinyl acetates are by far the largest technical
- Polyvinyl acetate is an important thermoplastic polymer and is used, among other things, as an adhesive (component), raw material for coatings, for packaging films, for the coating of paper and food (sausage and cheese coatings)
- polyvinyl acetate is produced by free radical polymerizations, the polymerization being able to be carried out in solution, in bulk and in emulsion.
- Azoisobutyronitrile and dibenzoyl peroxide (AIBN / BPO) are mainly used as radical initiators. Since these radical polymerizations take place quickly and in an uncontrolled manner, stereodifferentiation is ruled out and control of the molecular weight and the molecular weight distribution very difficult (W. Daniels in.. Kirk-Othmer encycl Chem Technol, 3rd Ed 1983, 23, 817-847.).
- the transition metal allows catalyzed insertion polymerization with so-called metallocene or post-metallocene synthesis of stereospecific polymers having a narrow molecular weight distribution (W. Kaminsky in Ullmann's Encyclopedia of Industrial Chemistry, 6 th Ed., 2002 Electronic Release, Wiley / VCH).
- catalysts with a suitable ligand structure have now been found which not only permit the simple insertion of vinyl esters, but also multiple insertion up to the formation of the polymer.
- the present invention relates to compounds of the formula I.
- M 1 is a transition metal of the 3rd to 12th group of the periodic table of the
- Elements means whose oxidation state is not equal to zero, preferably the 8th to 10th group, particularly preferably nickel or palladium, and
- R 1 is hydrogen or a Ci - C 2 o- carbon-containing group or
- R 2 is hydrogen or a Ci - C 2 o- carbon-containing group or
- Is halogen and is an integer between 1 and 4, and is an integer between 1 and 4, and
- L 1 is in each case identical or different and has a mono- or bidentate ligand
- Is donor atoms of the 14th to 16th group of elements preferably of the following basic structure
- X 1 is in each case the same or different, and is an element from the 14th to 16th group of elements, particularly preferably nitrogen or phosphorus, and
- X 2 is in each case the same or different, and an element of the 14th to 16th group of the elements, particularly preferably nitrogen or phosphorus, and R 3 is in each case the same or different, and is hydrogen or a Ci - C 2 o
- X 1 is a carbon-containing group, and when X 1 is nitrogen preferably a substituted arylidene or aryl group or when X 1 is phosphorus preferably a substituted aryl group and
- R 4 is in each case the same or different, and is hydrogen or a Ci - C 2 o - carbon-containing group, and if X 2 is nitrogen preferably a substituted arylidene or aryl group or if X 2 is phosphorus preferably a substituted aryl group Is group and R 5 is in each case the same or different, and is hydrogen or a Ci - C 2 o
- - is a carbon-containing group and can also form a cyclic system with R 6 or R 7 , and
- R 6 is in each case the same or different, and is hydrogen or a Ci - C 2 o
- - is a carbon-containing group and can also form a cyclic system with R 5 or R 7 , and
- R 7 is in each case identical or different and is hydrogen or a Ci - C 2 o - carbon-containing group, and can also form a cyclic system with R 5 or R 6 , and m is 0, 1 or 2, and n is equal Is 0, 1 or 2, and o is an integer from 0 to 20, preferably 0 to 10 and particularly preferably is 0, 1 or 2, and p is in each case identical or different and is 1 or 2, and q is the same or different and is 1 or 2, and r is the same or different and is 1 or 2.
- Ci in the context of the present invention
- - C 2 o carbon-containing group is preferably the radicals -C 2 -alkyl, particularly preferably methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl , t-butyl, n-pentyl, s-pentyl, cyclopentyl, n-hexyl, cyclohexyl, n-octyl or cyclooctyl, Ci - C 2 o - alkenyl, particularly preferably ethenyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, Cyclohexenyl, octenyl or cyclooctenyl, Ci - C 2 o - alkynyl, particularly preferably ethynyl, propyn
- C 4 -C 2 o-heterocycloalkyl particularly preferably furyl, benzofuryl, 2-pyrolidinyl, 2-indolyl, 3-indolyl, 2,3-dihydroindolyl, C 8 -C 2 o-arylalkenyl, particularly preferably o-vinylphenyl, m- vinylphenyl, p-vinylphenyl, C 8 -C 2 o-arylalkynyl, particularly preferably o-ethynylphenyl, m-ethynylphenyl or p-ethynylphenyl, C 2 - C 2 o - heteroatom-containing group, particularly preferably carbonyl, benzoyl, oxybenzoyl, benzoyloxy, acetyl .
- Acetoxy or nitrile understood, where one or more C 1 -C 2 o-carbon-containing groups can form a cyclic system.
- n 1 -5
- Ph may be the same or different and may be a phenyl, a substituted phenyl group such as tolyl or methoxyphenyl, a fluorinated phenyl, or an oxyphenyl, or another substituted aromatic radical and can also be an alkyl or oxyalkyl radical.
- iodaniline is reacted with diphenylphosphine to form the corresponding aminoarylphosphino compound under palladium catalysis.
- the corresponding ligand is then built up in a condensation reaction with a benzaldehyde derivative, which is then reacted directly with the desired metal species to form a catalyst according to the invention.
- the compounds of the formula I according to the invention are suitable as catalysts for the preparation of polyvinyl esters.
- Another component of the present invention are compounds of formula II, which is formed from a compound of formula I by conversion with vinyl esters.
- R 8 is the same or different and is hydrogen or a Ci - C 2 o- carbon-containing group
- R 9 is hydrogen or a Ci - C 2 o - carbon-containing group
- X 3 is a non-coordinating anion
- s is either an integer 1 or 2
- t is an integer between 1 and 3
- u is an integer between 1 and 3
- v is an integer between 1 and 3
- w is a is an integer between 1 and 3 where t multiplied by u is always equal to v multiplied by w, and the other radicals have the meaning defined under formula I, except for the compound of formula A.
- X 3 preferably means those composed of mixtures of several atoms of the elements aluminum, boron, antimony, arsenic, nitrogen, carbon, phosphorus, sulfur, oxygen, chlorine and fluorine. In the context of this invention, this is particularly preferably understood to mean fluorinated or perfluorinated Ci - C 2 o -carbon-containing groups.
- Illustrative, but not limiting, examples of this are: tetraphenylborate, tetrafluoroborate, tetrakis (pentafluorophenyl) borate, tetrakis (dimethylphenyl) borate, tetrakis (tolyl) borate, tetrakis (3,5-bis-trifluoromethylphenyl) borate, tetrakis (tetrakis) , Tetrakis (4-fluorophenyl) borate, tetrakis (pentafluoropheny!)
- a cationic complex is first produced by the addition of a silver salt by abstraction of the chloride ion.
- this cationic complex inserts, for example, a molecule of vinyl acetate and thus forms a complex of the formula II.
- Another component of the present invention is a process for the polymerization of vinyl esters using the catalyst or catalyst system according to the invention, polymerization being understood to mean both the homopolymerization of vinyl esters and the copolymerization of vinyl esters with other olefins.
- Examples of other olefins are 1-olefins having 2 to 20, preferably 2 to 10, carbon atoms, such as ethene, propene, 1-butene, 1-pentene, 1-hexene, 1-decene, 4-methyl-1-pentene or 1-octene, styrene, dienes such as 1,3-butadiene, 1,4-hexadiene, vinyl norbornene, norbornadiene, ethyl norbomadiene and cyclic olefins such as norbornene, cyclopentadiene, tetracyclododecene or methyl norbomene, and polar monomers such as methyl acrylate, methyl methacrylate, acrylic acid, acrylic acid, acrylic acid -Butyl acrylate and 2-ethylhexyl acrylate.
- Vinyl acetate is preferably homopolymerized in the process according to the invention, or vinyl acetate with one or more 1-olefins having 2 to 8 carbon atoms, such as
- the polymerization can optionally be carried out either with an additive of the formula III or without an additional additive:
- M 2 is the same or different and is a metal of the 1st to 14th group of the
- Periodic table is, preferably lithium, magnesium, scandium, titanium, boron, aluminum, silicon, tin, particularly preferably boron and aluminum, and R 9 is the same or different and is hydrogen, a halogen atom or a Ci
- the additives of the formula III optionally used according to the invention are one or more compounds of the type of an aluminoxane and / or another Lewis acid.
- the polymerization is carried out at a temperature of from -20 to 300 ° C., preferably from 0 to
- the polymerization can be carried out in solution, in bulk, in suspension or in emulsion, continuously or batchwise, in one or more stages.
- Suitable solvents for the polymerization are, for example, aliphatic hydrocarbons such as pentane,
- the cocatalyst of the formula III which together with at least one compound of the formula I or formula II according to the invention can form the catalyst system, contains at least one compound of the aluminoxane or Lewis acid type.
- cocatalysts which can form the catalyst system together with a compound of the formula I or formula II are: aluminoxanes, for example in JACS 117 (1995), 6465-74 and Organometallics 13 (1994), 2957-2969 are described, or Lewis acids, which consist, for example, of boron or organoaluminium compounds, or cocatalysts, which are described in EP-A-924223, DE-A-19622207, EP-A-601830, EP-A-824112, EP-A -8241 13, EP-A-81 1627, WO97 / 1 1775 and DE-A-19606167.
- Lewis acids are those which contain at least one or more atoms of lithium, magnesium, scandium, titanium, boron, aluminum, silicon and / or tin. It is particularly preferred to use at least one organoboron or organoaluminum compound which contains C1-C20 carbon-containing groups, such as branched or unbranched alkyl or
- Haloalkyl such as methyl, propyl, isopropyl, isobutyl, trifluoromethyl, unsaturated groups, such as aryl or haloaryl, such as phenyl, tolyl, benzyl groups, p-fluorophenyl, 3,5-difluorophenyl, pentachlorophenyl, pentafluorophenyl, 3,4,5-trifluorophenyl and 3,5-di (trifluoromethyl) phenyl.
- unsaturated groups such as aryl or haloaryl, such as phenyl, tolyl, benzyl groups, p-fluorophenyl, 3,5-difluorophenyl, pentachlorophenyl, pentafluorophenyl, 3,4,5-trifluorophenyl and 3,5-di (trifluoromethyl) phenyl.
- aryl or haloaryl such as phenyl, to
- Tris (3,5-difluorophenyl) borane Tris (3,5-difluorophenyl) borane, tris (4-fluoromethylphenyl) borane, tris (pentafluorophenyl) borane, tris (tolyl) borane, tris (3,5-dimethylphenyl) borane, tris (3,5-difluorophenyl) borane, Tris (3,4,5-trifluorophenyl) borane.
- the carrier component of the catalyst system according to the invention can be any organic or inorganic, inert solid, in particular a porous carrier such as talc, inorganic oxides and finely divided polymer powders (e.g. highly porous polyolefins, such as
- polar polymers such as. e.g. Polyurethanes, polymethacrylates, polymethyl methacrylates, polyvinyl acetate, polyacrylonitrile, polyethylene glycol or copolymers).
- Suitable inorganic oxides can be found in the II. VI. Main group of the
- Periodic table and the lll.-IV. Subgroup of the Periodic Table of the Elements examples include silicon dioxide, hydrotalcite, aluminum oxide, and mixed oxides of the elements calcium, aluminum, silicon, magnesium, titanium and corresponding oxide mixtures.
- preferred oxides as carriers include silicon dioxide, hydrotalcite, aluminum oxide, and mixed oxides of the elements calcium, aluminum, silicon, magnesium, titanium and corresponding oxide mixtures.
- Other inorganic oxides that can be used alone or in combination with the last-mentioned preferred oxidic supports are, for example, MgO, ZrO 2 , TiO 2 or B 2 O 3 , to name just a few. The invention is illustrated by the following examples which, however, do not restrict the invention.
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Abstract
L'invention concerne des composés d'un genre nouveau, pouvant s'utiliser comme catalyseurs dans la polymérisation et la copolymérisation de vinylesters. L'invention concerne en outre un procédé de polymérisation et de copolymérisation de vinylesters, à l'aide desdits composés.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE2002154093 DE10254093A1 (de) | 2002-11-20 | 2002-11-20 | Übergangsmetall-Katalysatoren zur Herstellung von Polyvinylestern |
DE10254093.4 | 2002-11-20 |
Publications (1)
Publication Number | Publication Date |
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WO2004046209A1 true WO2004046209A1 (fr) | 2004-06-03 |
Family
ID=32308601
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2003/012538 WO2004046209A1 (fr) | 2002-11-20 | 2003-11-11 | Catalyseurs de metal de transition pour produire des polyvinylesters |
Country Status (2)
Country | Link |
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DE (1) | DE10254093A1 (fr) |
WO (1) | WO2004046209A1 (fr) |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0824111A1 (fr) * | 1996-08-12 | 1998-02-18 | Elf Atochem S.A. | Procédé de polymérisation ou copolymérisation radicalaire contrÔlée de monomères (méth)acryliques et vinyliques et (co)polymères obtenus |
WO2001021670A1 (fr) * | 1999-09-20 | 2001-03-29 | The Penn State Research Foundation | Polymerisation de norbornene et d'acrylatescatalysee par le palladium(ii) |
-
2002
- 2002-11-20 DE DE2002154093 patent/DE10254093A1/de not_active Withdrawn
-
2003
- 2003-11-11 WO PCT/EP2003/012538 patent/WO2004046209A1/fr not_active Application Discontinuation
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0824111A1 (fr) * | 1996-08-12 | 1998-02-18 | Elf Atochem S.A. | Procédé de polymérisation ou copolymérisation radicalaire contrÔlée de monomères (méth)acryliques et vinyliques et (co)polymères obtenus |
WO2001021670A1 (fr) * | 1999-09-20 | 2001-03-29 | The Penn State Research Foundation | Polymerisation de norbornene et d'acrylatescatalysee par le palladium(ii) |
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DE10254093A1 (de) | 2004-06-09 |
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