CA2456711C - Chain growth reaction process using zinc alkyls - Google Patents
Chain growth reaction process using zinc alkyls Download PDFInfo
- Publication number
- CA2456711C CA2456711C CA2456711A CA2456711A CA2456711C CA 2456711 C CA2456711 C CA 2456711C CA 2456711 A CA2456711 A CA 2456711A CA 2456711 A CA2456711 A CA 2456711A CA 2456711 C CA2456711 C CA 2456711C
- Authority
- CA
- Canada
- Prior art keywords
- iii
- group
- hydrocarbyl
- heterohydrocarbyl
- substituted
- 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.)
- Expired - Lifetime
Links
- 239000011701 zinc Substances 0.000 title claims abstract description 53
- 238000006243 chemical reaction Methods 0.000 title claims abstract description 49
- 229910052725 zinc Inorganic materials 0.000 title claims abstract description 44
- 238000000034 method Methods 0.000 claims abstract description 82
- 239000003054 catalyst Substances 0.000 claims abstract description 74
- -1 alkoxide compounds Chemical class 0.000 claims abstract description 57
- 150000003624 transition metals Chemical class 0.000 claims abstract description 56
- 229910052723 transition metal Inorganic materials 0.000 claims abstract description 55
- 239000004711 α-olefin Substances 0.000 claims abstract description 35
- 238000002360 preparation method Methods 0.000 claims abstract description 26
- 150000001336 alkenes Chemical class 0.000 claims abstract description 25
- 229910052768 actinide Inorganic materials 0.000 claims abstract description 20
- 150000001255 actinides Chemical class 0.000 claims abstract description 20
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 20
- 239000012190 activator Substances 0.000 claims abstract description 19
- 229910052747 lanthanoid Inorganic materials 0.000 claims abstract description 19
- 150000002602 lanthanoids Chemical class 0.000 claims abstract description 19
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000006073 displacement reaction Methods 0.000 claims abstract description 13
- 230000003647 oxidation Effects 0.000 claims abstract description 13
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 13
- 150000003138 primary alcohols Chemical class 0.000 claims abstract description 7
- 150000004703 alkoxides Chemical class 0.000 claims abstract description 5
- 230000007062 hydrolysis Effects 0.000 claims abstract description 5
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 5
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 157
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 92
- 229910052739 hydrogen Inorganic materials 0.000 claims description 71
- 239000001257 hydrogen Substances 0.000 claims description 71
- 229910052736 halogen Inorganic materials 0.000 claims description 65
- 150000002367 halogens Chemical group 0.000 claims description 65
- 239000010936 titanium Substances 0.000 claims description 58
- HQWPLXHWEZZGKY-UHFFFAOYSA-N diethylzinc Chemical compound CC[Zn]CC HQWPLXHWEZZGKY-UHFFFAOYSA-N 0.000 claims description 47
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 45
- 125000004429 atom Chemical group 0.000 claims description 40
- 239000000203 mixture Substances 0.000 claims description 38
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 32
- 238000009826 distribution Methods 0.000 claims description 30
- 150000001875 compounds Chemical class 0.000 claims description 26
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical compound [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 claims description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 229910052698 phosphorus Inorganic materials 0.000 claims description 21
- 229910052799 carbon Inorganic materials 0.000 claims description 17
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical group [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 15
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 229910021577 Iron(II) chloride Inorganic materials 0.000 claims description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 10
- 125000004122 cyclic group Chemical group 0.000 claims description 10
- NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 claims description 10
- 239000000463 material Substances 0.000 claims description 9
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical class CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 239000012968 metallocene catalyst Substances 0.000 claims description 8
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 7
- 239000011541 reaction mixture Substances 0.000 claims description 7
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 6
- 239000003085 diluting agent Substances 0.000 claims description 6
- 150000002899 organoaluminium compounds Chemical class 0.000 claims description 6
- 229920000642 polymer Polymers 0.000 claims description 6
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 5
- MIILMDFFARLWKZ-UHFFFAOYSA-L dichlorozirconium;1,2,3,4,5-pentamethylcyclopentane Chemical compound [Cl-].[Cl-].CC1=C(C)C(C)=C(C)C1(C)[Zr+2]C1(C)C(C)=C(C)C(C)=C1C MIILMDFFARLWKZ-UHFFFAOYSA-L 0.000 claims description 5
- 239000003446 ligand Substances 0.000 claims description 5
- 229910052759 nickel Inorganic materials 0.000 claims description 5
- 239000000377 silicon dioxide Substances 0.000 claims description 5
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 claims description 4
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- 150000002430 hydrocarbons Chemical class 0.000 claims description 4
- 239000007791 liquid phase Substances 0.000 claims description 4
- 239000012071 phase Substances 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 229910052719 titanium Inorganic materials 0.000 claims description 4
- HEPBQSXQJMTVFI-UHFFFAOYSA-N zinc;butane Chemical compound [Zn+2].CCC[CH2-].CCC[CH2-] HEPBQSXQJMTVFI-UHFFFAOYSA-N 0.000 claims description 4
- WCGXJPFHTHQNJL-UHFFFAOYSA-N 1-[5-ethyl-2-hydroxy-4-[6-methyl-6-(2H-tetrazol-5-yl)heptoxy]phenyl]ethanone Chemical compound CCC1=CC(C(C)=O)=C(O)C=C1OCCCCCC(C)(C)C1=NNN=N1 WCGXJPFHTHQNJL-UHFFFAOYSA-N 0.000 claims description 3
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 3
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 claims description 3
- VVNYDCGZZSTUBC-UHFFFAOYSA-N 5-amino-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-oxopentanoic acid Chemical compound CC(C)(C)OC(=O)NC(C(O)=O)CCC(N)=O VVNYDCGZZSTUBC-UHFFFAOYSA-N 0.000 claims description 3
- LHHAUUVITWQDQI-UHFFFAOYSA-L CC1=C(C)C(C)(C(C)=C1C)[Zr](Cl)(Cl)C1C=CC=C1 Chemical compound CC1=C(C)C(C)(C(C)=C1C)[Zr](Cl)(Cl)C1C=CC=C1 LHHAUUVITWQDQI-UHFFFAOYSA-L 0.000 claims description 3
- UBHZUDXTHNMNLD-UHFFFAOYSA-N dimethylsilane Chemical compound C[SiH2]C UBHZUDXTHNMNLD-UHFFFAOYSA-N 0.000 claims description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 3
- 238000011534 incubation Methods 0.000 claims description 3
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 3
- BMGNSKKZFQMGDH-FDGPNNRMSA-L nickel(2+);(z)-4-oxopent-2-en-2-olate Chemical compound [Ni+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O BMGNSKKZFQMGDH-FDGPNNRMSA-L 0.000 claims description 3
- 150000003254 radicals Chemical class 0.000 claims description 3
- FOKGVHRHBBEPPI-UHFFFAOYSA-K 1,2,3,4,5-pentamethylcyclopentane;trichlorozirconium Chemical compound Cl[Zr](Cl)Cl.C[C]1[C](C)[C](C)[C](C)[C]1C FOKGVHRHBBEPPI-UHFFFAOYSA-K 0.000 claims description 2
- MQNPENQYQXUCOX-UHFFFAOYSA-N C=1C=CC=CC=1C[Zn]CC1=CC=CC=C1 Chemical compound C=1C=CC=CC=1C[Zn]CC1=CC=CC=C1 MQNPENQYQXUCOX-UHFFFAOYSA-N 0.000 claims description 2
- AYEXPZYTCYCMPE-UHFFFAOYSA-N CCCCCCCCCCCC[Zn]CCCCCCCCCCCC Chemical compound CCCCCCCCCCCC[Zn]CCCCCCCCCCCC AYEXPZYTCYCMPE-UHFFFAOYSA-N 0.000 claims description 2
- QGAXJIMCDCDTDX-UHFFFAOYSA-N CCCCCCCCCC[Zn]CCCCCCCCCC Chemical compound CCCCCCCCCC[Zn]CCCCCCCCCC QGAXJIMCDCDTDX-UHFFFAOYSA-N 0.000 claims description 2
- JUOCTSZRGAFSKS-UHFFFAOYSA-N CCCCCC[Zn]CCCCCC Chemical compound CCCCCC[Zn]CCCCCC JUOCTSZRGAFSKS-UHFFFAOYSA-N 0.000 claims description 2
- AXAZMDOAUQTMOW-UHFFFAOYSA-N dimethylzinc Chemical compound C[Zn]C AXAZMDOAUQTMOW-UHFFFAOYSA-N 0.000 claims description 2
- 239000007789 gas Substances 0.000 claims description 2
- 229910001629 magnesium chloride Inorganic materials 0.000 claims description 2
- 239000002002 slurry Substances 0.000 claims description 2
- 239000010457 zeolite Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 57
- 150000003752 zinc compounds Chemical class 0.000 claims 20
- 241000894007 species Species 0.000 claims 6
- 241001334141 Rugopharynx alpha Species 0.000 claims 4
- NAZRUGZOBLWKCP-UHFFFAOYSA-K CC1=C(C)C(C)(C(C)=C1C)[Zr](Cl)(Cl)(Cl)C1(C)C(C)=C(C)C(C)=C1C Chemical compound CC1=C(C)C(C)(C(C)=C1C)[Zr](Cl)(Cl)(Cl)C1(C)C(C)=C(C)C(C)=C1C NAZRUGZOBLWKCP-UHFFFAOYSA-K 0.000 claims 1
- 150000004696 coordination complex Chemical class 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 abstract description 13
- 239000002184 metal Substances 0.000 abstract description 13
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 42
- 239000005977 Ethylene Substances 0.000 description 42
- 235000016804 zinc Nutrition 0.000 description 38
- 239000000243 solution Substances 0.000 description 32
- 230000000694 effects Effects 0.000 description 25
- 239000000047 product Substances 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- CPOFMOWDMVWCLF-UHFFFAOYSA-N methyl(oxo)alumane Chemical compound C[Al]=O CPOFMOWDMVWCLF-UHFFFAOYSA-N 0.000 description 16
- 150000001335 aliphatic alkanes Chemical class 0.000 description 15
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 14
- 229910052782 aluminium Inorganic materials 0.000 description 13
- 239000004411 aluminium Substances 0.000 description 12
- 150000002431 hydrogen Chemical class 0.000 description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
- 238000002474 experimental method Methods 0.000 description 10
- 229910052742 iron Inorganic materials 0.000 description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- 238000004817 gas chromatography Methods 0.000 description 8
- 125000001424 substituent group Chemical group 0.000 description 7
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 5
- 229960004132 diethyl ether Drugs 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000004698 Polyethylene Substances 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-MZWXYZOWSA-N benzene-d6 Chemical compound [2H]C1=C([2H])C([2H])=C([2H])C([2H])=C1[2H] UHOVQNZJYSORNB-MZWXYZOWSA-N 0.000 description 4
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 4
- 229920000573 polyethylene Polymers 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- YIJNSXZCHXCBSZ-UHFFFAOYSA-L 2-n,3-n-bis[2,6-di(propan-2-yl)phenyl]butane-2,3-diimine;nickel(2+);dibromide Chemical compound Br[Ni]Br.CC(C)C1=CC=CC(C(C)C)=C1N=C(C)C(C)=NC1=C(C(C)C)C=CC=C1C(C)C YIJNSXZCHXCBSZ-UHFFFAOYSA-L 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000000816 ethylene group Chemical class [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 150000004678 hydrides Chemical class 0.000 description 3
- 125000001841 imino group Chemical group [H]N=* 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 2
- HFDVRLIODXPAHB-UHFFFAOYSA-N 1-tetradecene Chemical compound CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 229910021585 Nickel(II) bromide Inorganic materials 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229910007928 ZrCl2 Inorganic materials 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000007942 carboxylates Chemical class 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- IJSDUKZKUCXMRL-UHFFFAOYSA-L dichlorozirconium;1-[2-(1h-inden-1-yl)ethyl]-1h-indene Chemical compound Cl[Zr]Cl.C1=CC2=CC=CC=C2C1CCC1C2=CC=CC=C2C=C1 IJSDUKZKUCXMRL-UHFFFAOYSA-L 0.000 description 2
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- UIEKYBOPAVTZKW-UHFFFAOYSA-L naphthalene-2-carboxylate;nickel(2+) Chemical compound [Ni+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 UIEKYBOPAVTZKW-UHFFFAOYSA-L 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- IPLJNQFXJUCRNH-UHFFFAOYSA-L nickel(2+);dibromide Chemical compound [Ni+2].[Br-].[Br-] IPLJNQFXJUCRNH-UHFFFAOYSA-L 0.000 description 2
- ZCYXXKJEDCHMGH-UHFFFAOYSA-N nonane Chemical compound CCCC[CH]CCCC ZCYXXKJEDCHMGH-UHFFFAOYSA-N 0.000 description 2
- BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000002524 organometallic group Chemical group 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 2
- OGHBATFHNDZKSO-UHFFFAOYSA-N propan-2-olate Chemical compound CC(C)[O-] OGHBATFHNDZKSO-UHFFFAOYSA-N 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 150000003623 transition metal compounds Chemical class 0.000 description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 229910052726 zirconium Inorganic materials 0.000 description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- VCLJODPNBNEBKW-UHFFFAOYSA-N 2,2,4,4,6,8,8-heptamethylnonane Chemical compound CC(C)(C)CC(C)CC(C)(C)CC(C)(C)C VCLJODPNBNEBKW-UHFFFAOYSA-N 0.000 description 1
- 229940043268 2,2,4,4,6,8,8-heptamethylnonane Drugs 0.000 description 1
- BEZVGIHGZPLGBL-UHFFFAOYSA-N 2,6-diacetylpyridine Chemical compound CC(=O)C1=CC=CC(C(C)=O)=N1 BEZVGIHGZPLGBL-UHFFFAOYSA-N 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- RSPAIISXQHXRKX-UHFFFAOYSA-L 5-butylcyclopenta-1,3-diene;zirconium(4+);dichloride Chemical compound Cl[Zr+2]Cl.CCCCC1=CC=C[CH-]1.CCCCC1=CC=C[CH-]1 RSPAIISXQHXRKX-UHFFFAOYSA-L 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- DQQYMYCFOGWCCT-UHFFFAOYSA-N CC(C)(C)CC[Zn]CCC(C)(C)C Chemical compound CC(C)(C)CC[Zn]CCC(C)(C)C DQQYMYCFOGWCCT-UHFFFAOYSA-N 0.000 description 1
- DTGJWZNTRSBQBB-UHFFFAOYSA-N CC(C)c1cccc(C(C)C)c1[N] Chemical group CC(C)c1cccc(C(C)C)c1[N] DTGJWZNTRSBQBB-UHFFFAOYSA-N 0.000 description 1
- YEYLJURTFOLIQG-UHFFFAOYSA-N CCCCCC[Zn] Chemical group CCCCCC[Zn] YEYLJURTFOLIQG-UHFFFAOYSA-N 0.000 description 1
- 101100219382 Caenorhabditis elegans cah-2 gene Proteins 0.000 description 1
- 229910021580 Cobalt(II) chloride Inorganic materials 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 229920000034 Plastomer Polymers 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 238000006932 Simmons-Smith cyclopropanation reaction Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000005234 alkyl aluminium group Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical group 0.000 description 1
- GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 150000001923 cyclic compounds Chemical class 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
- IDASTKMEQGPVRR-UHFFFAOYSA-N cyclopenta-1,3-diene;zirconium(2+) Chemical compound [Zr+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 IDASTKMEQGPVRR-UHFFFAOYSA-N 0.000 description 1
- QRUYYSPCOGSZGQ-UHFFFAOYSA-L cyclopentane;dichlorozirconium Chemical compound Cl[Zr]Cl.[CH]1[CH][CH][CH][CH]1.[CH]1[CH][CH][CH][CH]1 QRUYYSPCOGSZGQ-UHFFFAOYSA-L 0.000 description 1
- KYHHMFUFEIHUHB-UHFFFAOYSA-N di-tert-butylzinc Chemical compound CC(C)(C)[Zn]C(C)(C)C KYHHMFUFEIHUHB-UHFFFAOYSA-N 0.000 description 1
- 229910000071 diazene Inorganic materials 0.000 description 1
- RLGVOYAJPAUNAP-UHFFFAOYSA-L dichloroiron N-[2,6-di(propan-2-yl)phenyl]-1-[2-[N-[2,6-di(propan-2-yl)phenyl]-C-phenylcarbonimidoyl]-6-methylpyrimidin-4-yl]-1-phenylmethanimine Chemical compound Cl[Fe]Cl.CC(C)C1=CC=CC(C(C)C)=C1N=C(C=1N=C(N=C(C)C=1)C(=NC=1C(=CC=CC=1C(C)C)C(C)C)C=1C=CC=CC=1)C1=CC=CC=C1 RLGVOYAJPAUNAP-UHFFFAOYSA-L 0.000 description 1
- PGOQFBTTZHLHCW-UHFFFAOYSA-L dichloroiron;pyridine Chemical compound Cl[Fe]Cl.C1=CC=NC=C1 PGOQFBTTZHLHCW-UHFFFAOYSA-L 0.000 description 1
- YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 description 1
- 238000007323 disproportionation reaction Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- UAIZDWNSWGTKFZ-UHFFFAOYSA-L ethylaluminum(2+);dichloride Chemical compound CC[Al](Cl)Cl UAIZDWNSWGTKFZ-UHFFFAOYSA-L 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
- 229910052735 hafnium Inorganic materials 0.000 description 1
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000002638 heterogeneous catalyst Substances 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- GBRJQTLHXWRDOV-UHFFFAOYSA-M magnesium;hexane;chloride Chemical compound [Mg+2].[Cl-].CCCCC[CH2-] GBRJQTLHXWRDOV-UHFFFAOYSA-M 0.000 description 1
- 238000004519 manufacturing process Methods 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
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group 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
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 150000004857 phospholes Chemical class 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 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
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 229940095068 tetradecene Drugs 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000007944 thiolates Chemical class 0.000 description 1
- 230000036962 time dependent Effects 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
- LFXVBWRMVZPLFK-UHFFFAOYSA-N trioctylalumane Chemical compound CCCCCCCC[Al](CCCCCCCC)CCCCCCCC LFXVBWRMVZPLFK-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
- 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
- 238000005292 vacuum distillation Methods 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- VPGLGRNSAYHXPY-UHFFFAOYSA-L zirconium(2+);dichloride Chemical compound Cl[Zr]Cl VPGLGRNSAYHXPY-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/02—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons
- C07C2/04—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation
- C07C2/06—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation of alkenes, i.e. acyclic hydrocarbons having only one carbon-to-carbon double bond
- C07C2/08—Catalytic processes
- C07C2/26—Catalytic processes with hydrides or organic compounds
- C07C2/30—Catalytic processes with hydrides or organic compounds containing metal-to-carbon bond; Metal hydrides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/32—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen
- C07C1/325—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen the hetero-atom being a metal atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/48—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxidation reactions with formation of hydroxy groups
- C07C29/50—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxidation reactions with formation of hydroxy groups with molecular oxygen only
- C07C29/54—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxidation reactions with formation of hydroxy groups with molecular oxygen only starting from compounds containing carbon-to-metal bonds and followed by conversion of the -O- metal to -OH groups
-
- 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
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/06—Zinc compounds
-
- 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
- C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
-
- 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
- C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F10/02—Ethene
-
- 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
- C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F210/16—Copolymers of ethene with alpha-alkenes, e.g. EP rubbers
-
- 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
- C08F2410/00—Features related to the catalyst preparation, the catalyst use or to the deactivation of the catalyst
- C08F2410/01—Additive used together with the catalyst, excluding compounds containing Al or B
-
- 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
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
- C08F4/62—Refractory metals or compounds thereof
- C08F4/64—Titanium, zirconium, hafnium or compounds thereof
- C08F4/659—Component covered by group C08F4/64 containing a transition metal-carbon bond
- C08F4/6592—Component covered by group C08F4/64 containing a transition metal-carbon bond containing at least one cyclopentadienyl ring, condensed or not, e.g. an indenyl or a fluorenyl ring
- C08F4/65922—Component covered by group C08F4/64 containing a transition metal-carbon bond containing at least one cyclopentadienyl ring, condensed or not, e.g. an indenyl or a fluorenyl ring containing at least two cyclopentadienyl rings, fused or not
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S526/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S526/941—Synthetic resins or natural rubbers -- part of the class 520 series having the transition metal bonded directly to carbon
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S526/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S526/943—Polymerization with metallocene catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/921,695 | 2001-08-06 | ||
| US09/921,695 US7087686B2 (en) | 2001-08-06 | 2001-08-06 | Chain growth reaction process |
| PCT/GB2002/003096 WO2003014046A1 (en) | 2001-08-06 | 2002-07-05 | Chain growth reaction process |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2456711A1 CA2456711A1 (en) | 2003-02-20 |
| CA2456711C true CA2456711C (en) | 2013-01-08 |
Family
ID=25445836
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2456711A Expired - Lifetime CA2456711C (en) | 2001-08-06 | 2002-07-05 | Chain growth reaction process using zinc alkyls |
Country Status (10)
| Country | Link |
|---|---|
| US (3) | US7087686B2 (enExample) |
| EP (2) | EP1414772B1 (enExample) |
| JP (1) | JP2004537584A (enExample) |
| KR (1) | KR100895599B1 (enExample) |
| CN (2) | CN100457695C (enExample) |
| CA (1) | CA2456711C (enExample) |
| EA (2) | EA007922B1 (enExample) |
| ES (2) | ES2711251T3 (enExample) |
| MY (1) | MY143732A (enExample) |
| WO (1) | WO2003014046A1 (enExample) |
Families Citing this family (94)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001053369A1 (en) * | 2000-01-21 | 2001-07-26 | Mitsui Chemicals, Inc. | Olefin block copolymers, production processes of the same and use thereof |
| US8426535B2 (en) * | 2001-08-06 | 2013-04-23 | Ineos Europe Limited | Chain growth reaction process |
| US7087686B2 (en) * | 2001-08-06 | 2006-08-08 | Bp Chemicals Limited | Chain growth reaction process |
| BR0212317A (pt) * | 2001-09-14 | 2004-09-21 | Basell Polyolefine Gmbh | Processo para a polimerização de olefinas na presença de um sistema de catalisador, uso do mesmo, e, polìmero |
| DE10145453A1 (de) * | 2001-09-14 | 2003-06-05 | Basell Polyolefine Gmbh | Monocyclopentadienylkomplexe mit einem kondensierten Heterocyclus |
| US7608668B2 (en) | 2004-03-17 | 2009-10-27 | Dow Global Technologies Inc. | Ethylene/α-olefins block interpolymers |
| US7504347B2 (en) | 2004-03-17 | 2009-03-17 | Dow Global Technologies Inc. | Fibers made from copolymers of propylene/α-olefins |
| BRPI0508148B1 (pt) | 2004-03-17 | 2015-09-01 | Dow Global Technologies Inc. | Interpolímero de etileno em multibloco, derivado reticulado e composição |
| US7524911B2 (en) | 2004-03-17 | 2009-04-28 | Dow Global Technologies Inc. | Adhesive and marking compositions made from interpolymers of ethylene/α-olefins |
| US7863379B2 (en) | 2004-03-17 | 2011-01-04 | Dow Global Technologies Inc. | Impact modification of thermoplastics with ethylene/alpha-olefin interpolymers |
| US7795321B2 (en) | 2004-03-17 | 2010-09-14 | Dow Global Technologies Inc. | Rheology modification of interpolymers of ethylene/α-olefins and articles made therefrom |
| US8273838B2 (en) | 2004-03-17 | 2012-09-25 | Dow Global Technologies Llc | Propylene/α-olefins block interpolymers |
| US7355089B2 (en) | 2004-03-17 | 2008-04-08 | Dow Global Technologies Inc. | Compositions of ethylene/α-olefin multi-block interpolymer for elastic films and laminates |
| US7671131B2 (en) | 2004-03-17 | 2010-03-02 | Dow Global Technologies Inc. | Interpolymers of ethylene/α-olefins blends and profiles and gaskets made therefrom |
| US7741397B2 (en) | 2004-03-17 | 2010-06-22 | Dow Global Technologies, Inc. | Filled polymer compositions made from interpolymers of ethylene/α-olefins and uses thereof |
| US7803728B2 (en) | 2004-03-17 | 2010-09-28 | Dow Global Technologies Inc. | Fibers made from copolymers of ethylene/α-olefins |
| US7622529B2 (en) | 2004-03-17 | 2009-11-24 | Dow Global Technologies Inc. | Polymer blends from interpolymers of ethylene/alpha-olefin with improved compatibility |
| AR053693A1 (es) | 2004-03-17 | 2007-05-16 | Dow Global Technologies Inc | Composiciones de interpolimero de etileno/alfa-olefina multibloque adecuado para peliculas |
| US7514517B2 (en) | 2004-03-17 | 2009-04-07 | Dow Global Technologies Inc. | Anti-blocking compositions comprising interpolymers of ethylene/α-olefins |
| EP2792690B1 (en) * | 2004-03-17 | 2019-05-15 | Dow Global Technologies LLC | Catalyst composition comprising shuttling agent for ethylene multi-block copolymer formation |
| US7897689B2 (en) | 2004-03-17 | 2011-03-01 | Dow Global Technologies Inc. | Functionalized ethylene/α-olefin interpolymer compositions |
| US7557147B2 (en) | 2004-03-17 | 2009-07-07 | Dow Global Technologies Inc. | Soft foams made from interpolymers of ethylene/alpha-olefins |
| US7579408B2 (en) | 2004-03-17 | 2009-08-25 | Dow Global Technologies Inc. | Thermoplastic vulcanizate comprising interpolymers of ethylene/α-olefins |
| US7622179B2 (en) | 2004-03-17 | 2009-11-24 | Dow Global Technologies Inc. | Three dimensional random looped structures made from interpolymers of ethylene/α-olefins and uses thereof |
| US7687442B2 (en) | 2004-03-17 | 2010-03-30 | Dow Global Technologies Inc. | Low molecular weight ethylene/α-olefin interpolymer as base lubricant oils |
| US8211982B2 (en) | 2004-03-17 | 2012-07-03 | Dow Global Technologies Llc | Functionalized ethylene/α-olefin interpolymer compositions |
| US7671106B2 (en) | 2004-03-17 | 2010-03-02 | Dow Global Technologies Inc. | Cap liners, closures and gaskets from multi-block polymers |
| US7666918B2 (en) | 2004-03-17 | 2010-02-23 | Dow Global Technologies, Inc. | Foams made from interpolymers of ethylene/α-olefins |
| US7582716B2 (en) | 2004-03-17 | 2009-09-01 | Dow Global Technologies Inc. | Compositions of ethylene/α-olefin multi-block interpolymer for blown films with high hot tack |
| US7714071B2 (en) | 2004-03-17 | 2010-05-11 | Dow Global Technologies Inc. | Polymer blends from interpolymers of ethylene/α-olefins and flexible molded articles made therefrom |
| US7662881B2 (en) | 2004-03-17 | 2010-02-16 | Dow Global Technologies Inc. | Viscosity index improver for lubricant compositions |
| KR100617990B1 (ko) * | 2004-07-30 | 2006-09-01 | 한국화학연구원 | 다핵으로 연결된 전이금속 화합물 및 이를 이용한 개환복분해 중합체의 제조방법 |
| BRPI0609826B1 (pt) | 2005-03-17 | 2022-09-27 | Dow Global Technologies Inc | Composição adequada para uso em películas e laminados elásticos, camada de película elástica, laminado e artigo fabricado |
| US7786216B2 (en) | 2005-03-17 | 2010-08-31 | Dow Global Technologies Inc. | Oil based blends of interpolymers of ethylene/α-olefins |
| US7910658B2 (en) | 2005-03-17 | 2011-03-22 | Dow Global Technologies Llc | Compositions of ethylene/α-olefin multi-block interpolymer for elastic films and laminates |
| US7737215B2 (en) | 2005-03-17 | 2010-06-15 | Dow Global Technologies Inc. | Compositions of ethylene/α-olefin multi-block interpolymer for elastic films and laminates |
| AR054017A1 (es) | 2005-03-17 | 2007-05-30 | Dow Global Technologies Inc | Fundas de tapas cierres y juntas de polimeros multi-bloque |
| AU2006227348A1 (en) | 2005-03-17 | 2006-09-28 | Dow Global Technologies Inc. | Adhesive and marking compositions made from interpolymers of ethylene/alpha-olefins |
| US7906587B2 (en) | 2005-09-16 | 2011-03-15 | Dow Global Technologies Llc | Polymer blends from interpolymer of ethylene/α olefin with improved compatibility |
| US7695812B2 (en) | 2005-09-16 | 2010-04-13 | Dow Global Technologies, Inc. | Fibers made from copolymers of ethylene/α-olefins |
| AR058496A1 (es) | 2005-10-26 | 2008-02-06 | Dow Global Technologies Inc | Articulos elasticos de multiples capas |
| US8153243B2 (en) | 2005-12-09 | 2012-04-10 | Dow Global Technologies Llc | Interpolymers suitable for multilayer films |
| JP5502325B2 (ja) | 2005-12-09 | 2014-05-28 | ダウ グローバル テクノロジーズ エルエルシー | エチレン／α−オレフィン組成物における分子量分布の制御方法 |
| EP2799235A1 (en) | 2007-10-22 | 2014-11-05 | Dow Global Technologies LLC | Multilayer films |
| CA2705141C (en) † | 2007-11-09 | 2016-05-17 | University Of Maryland, College Park | Process for preparation of polyolefins via living coordinative chain transfer polymerization |
| KR100973929B1 (ko) * | 2008-02-11 | 2010-08-03 | 한국도로공사 | 도로의 음원생성장치 및 그 시공방법 |
| KR101006996B1 (ko) * | 2008-06-02 | 2011-01-12 | 주식회사 유일컴 | 지하철 보도용 점자블록 |
| CN102089310A (zh) * | 2008-06-20 | 2011-06-08 | Tpi企业有限公司 | 用于合成n-去甲基吗啡烷化合物的方法 |
| SG176951A1 (en) | 2009-07-01 | 2012-02-28 | Mitsui Chemicals Inc | Organometallic compound and production method thereof |
| EP2665754A1 (en) | 2011-01-20 | 2013-11-27 | Ineos Commercial Services UK Limited | Activating supports |
| US20130131294A1 (en) * | 2011-11-21 | 2013-05-23 | John R. Hagadorn | Amidinate Catalyst Compounds, Process for Their Use and Polymers Produced Therefrom |
| WO2015103703A1 (en) * | 2014-01-08 | 2015-07-16 | The Governing Council Of The University Of Toronto | Iron(ii) catalysts containing tridentate pnp ligands, their synthesis, and use thereof |
| EP3037437A1 (en) | 2014-12-23 | 2016-06-29 | SABIC Global Technologies B.V. | Process for the preparation of a polyolefin having one or multiple end-functionalized branches. |
| EP3037438A1 (en) | 2014-12-23 | 2016-06-29 | SABIC Global Technologies B.V. | Process for the preparation of a branched polyolefin |
| EP3093280A1 (en) | 2015-05-13 | 2016-11-16 | Sasol Performance Chemicals GmbH | Process for the oligomerisation of olefins by coordinative chain transfer polymerisation and catalyst synthesis |
| KR102577009B1 (ko) * | 2015-05-29 | 2023-09-12 | 다우 글로벌 테크놀로지스 엘엘씨 | 폴리올레핀의 제조 방법 |
| EP3387047B1 (en) | 2015-12-09 | 2020-01-01 | SABIC Global Technologies B.V. | Process for the preparation of polyolefin-based graft copolymers comprising a first long chain branched polyolefin block and one or multiple polymer side chains |
| KR102019467B1 (ko) | 2015-12-23 | 2019-11-04 | 주식회사 엘지화학 | 메탈로센 담지 촉매 및 이를 이용하는 폴리올레핀의 제조방법 |
| WO2018034760A1 (en) | 2016-08-15 | 2018-02-22 | Exxonmobil Chemical Patents Inc. | Propylene-alpha olefin copolymers and methods for making the same |
| WO2018034759A1 (en) | 2016-08-15 | 2018-02-22 | Exxonmobil Chemical Patents Inc. | Propylene-olefin copolymers and methods for making the same |
| JP6886858B2 (ja) * | 2017-05-09 | 2021-06-16 | Ｅｎｅｏｓ株式会社 | オリゴマーの製造方法 |
| EP3665210B1 (en) | 2017-07-25 | 2022-02-23 | Dow Silicones Corporation | Method for preparing a graft copolymer with a polyolefin backbone and polyorganosiloxane pendant groups |
| CN109422828A (zh) * | 2017-09-05 | 2019-03-05 | 中国石油化工股份有限公司 | 用于烯烃聚合的催化剂体系和制备低分子量聚乙烯的催化体系及方法和低分子量聚乙烯 |
| WO2019173605A1 (en) | 2018-03-08 | 2019-09-12 | Exxonmobil Chemical Patents Inc. | Ethylene-propylene branched copolymers as viscosity modifiers with enhanced fuel economy |
| US11041035B2 (en) | 2018-03-08 | 2021-06-22 | Exxonmobil Chemical Patents Inc. | Process to produce long-chain branched polyolefins using dienes |
| JP7378411B2 (ja) | 2018-03-19 | 2023-11-13 | ダウ シリコーンズ コーポレーション | ポリオレフィン－ポリジオルガノシロキサンブロックコポリマーおよびその合成のための加水分解反応方法 |
| EP3768766B8 (en) | 2018-03-19 | 2025-11-05 | Dow Silicones Corporation | Polyolefin-polydiorganosiloxane block copolymer and method for the synthesis thereof |
| WO2019182718A1 (en) | 2018-03-19 | 2019-09-26 | Dow Silicones Corporation | Hot melt adhesive composition containing a polyolefin - polydiorganosiloxane copolymer and methods for the preparation and use thereof |
| WO2019182719A1 (en) | 2018-03-19 | 2019-09-26 | Dow Silicones Corporation | Polyorganosiloxane hot melt adhesive compositions containing polyolefin - polydiorganoosiloxane copolymers and methods for the preparation and use thereof |
| ES3036867T3 (en) | 2018-04-26 | 2025-09-25 | Exxonmobil Chemical Patents Inc | Non-coordinating anion type activators containing cation having branched alkyl groups |
| EP3824017B1 (en) | 2018-07-17 | 2022-09-14 | Dow Silicones Corporation | Polysiloxane resin - polyolefin copolymer and methods for the preparation and use thereof |
| WO2020069853A1 (en) | 2018-10-02 | 2020-04-09 | Sabic Global Technologies B.V. | Method for the manufacture of a polyolefin compound |
| WO2020146375A2 (en) | 2019-01-08 | 2020-07-16 | Exxonmobil Chemical Patents Inc | Olefin polymerization processes featuring in situ blending of an oil extension |
| EP3941949B1 (en) | 2019-03-21 | 2025-10-22 | ExxonMobil Chemical Patents Inc. | Methods for improving gas phase polymerization |
| WO2020190511A1 (en) | 2019-03-21 | 2020-09-24 | Exxonmobil Chemical Patents Inc. | Methods for improving production in gas phase polymerization |
| WO2021025903A1 (en) | 2019-08-02 | 2021-02-11 | Exxonmobil Chemical Patents Inc. | Non-coordinating anion type activators for use with polyolefin polymerization catalysts |
| WO2021119089A1 (en) | 2019-12-11 | 2021-06-17 | Exxonmobil Chemical Patents Inc. | Processes for introduction of liquid activators in olefin polymerization reactions |
| WO2021126523A1 (en) | 2019-12-19 | 2021-06-24 | Exxonmobil Chemical Patents Inc. | Production of impact copolymer polypropylene using metallocene and ziegler-natta catalysts in parallel reactors |
| WO2021194831A1 (en) | 2020-03-25 | 2021-09-30 | Exxonmobil Chemical Patents Inc. | Alkylation of transition metal coordination catalyst complexes |
| FR3109898B1 (fr) * | 2020-05-07 | 2023-04-14 | Ifp Energies Now | Catalyseur d’hydrogénation sélective comprenant une répartition particulière du nickel et du molybdène |
| WO2021247244A2 (en) | 2020-06-03 | 2021-12-09 | Exxonmobil Chemical Patents Inc. | Process for production of thermoplastic vulcanizates using supported catalyst systems and compositions made therefrom |
| WO2021262838A1 (en) | 2020-06-26 | 2021-12-30 | Exxonmobil Chemical Patents Inc. | Copolymers composed of ethylene, a-olefin, non-conjugated diene, and substituted styrene and articles therefrom |
| CN116209683B (zh) | 2020-08-10 | 2025-05-13 | 埃克森美孚化学专利公司 | 向聚合反应器递送非芳族溶液的方法 |
| EP4210868A1 (en) * | 2020-09-14 | 2023-07-19 | Chevron Phillips Chemical Company Lp | Transition metal-catalyzed production of alcohol and carbonyl compounds from hydrocarbons |
| AR124333A1 (es) * | 2020-12-15 | 2023-03-15 | Shell Int Research | UN PROCESO PARA PRODUCIR a-OLEFINAS |
| US12503529B2 (en) | 2021-02-26 | 2025-12-23 | Exxonmobil Chemical Patents Inc. | Polymers of 4-substituted hexadiene and processes for production thereof |
| EP4337749A1 (en) | 2021-05-14 | 2024-03-20 | ExxonMobil Chemical Patents Inc. | Ethylene-propylene branched copolymers used as viscosity modifiers |
| EP4337750A1 (en) | 2021-05-14 | 2024-03-20 | ExxonMobil Chemical Patents Inc. | Ethylene-propylene branched copolymers as viscosity modifiers |
| CN122295349A (zh) | 2023-12-01 | 2026-06-26 | 埃克森美孚技术与工程公司 | 载体结合型活化剂、负载型催化剂体系及使用它们的工艺 |
| GB202401660D0 (en) | 2024-02-07 | 2024-03-20 | Imperial College Innovations Ltd | Polymers with antimicrobial properties |
| WO2025250307A1 (en) | 2024-05-30 | 2025-12-04 | ExxonMobil Technology and Engineering Company | Methods for improving gas phase polymerization |
| WO2026106697A1 (en) | 2024-11-13 | 2026-05-21 | ExxonMobil Technology and Engineering Company | Methods for improving gas phase polymerization |
| WO2026106761A1 (en) | 2024-11-18 | 2026-05-21 | ExxonMobil Technology and Engineering Company | Gas phase polymerization process |
| CN120904255B (zh) * | 2025-10-09 | 2025-12-16 | 北京大学 | 一种乙烯非选择性齐聚催化剂及其制备方法和应用 |
Family Cites Families (44)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4063009A (en) * | 1954-01-19 | 1977-12-13 | Studiengesellschaft Kohle M.B.H. | Polymerization of ethylenically unsaturated hydrocarbons |
| NL134018C (enExample) | 1961-05-29 | |||
| US4308369A (en) * | 1979-09-28 | 1981-12-29 | The Dow Chemical Company | High efficiency catalyst for polymerizing olefins |
| US4335016A (en) * | 1981-02-23 | 1982-06-15 | Chemplex Company | Catalyst and method |
| US4361714A (en) * | 1981-12-14 | 1982-11-30 | Exxon Research And Engineering Co. | Preparation of linear olefin products |
| US4855525A (en) * | 1987-06-19 | 1989-08-08 | Exxon Chemical Patents Inc. | Process for preparing linear alpha-olefins using zirconium adducts as catalysts |
| US5034483A (en) * | 1988-01-15 | 1991-07-23 | Mobil Oil Corporation | Process for preparing high density, broad molecular weight distribution alpha-olefin polymers |
| GB8918497D0 (en) * | 1989-08-14 | 1989-09-20 | Exxon Chemical Patents Inc | Process for preparing linear alpha-olefins from ethylene |
| US5068489A (en) * | 1989-12-28 | 1991-11-26 | Union Carbide Chemicals And Plastics Technology Corporation | Preparation of very low molecular weight polyethylene in a fluidized bed |
| EP0464744A3 (en) * | 1990-07-02 | 1992-05-13 | Union Carbide Chemicals And Plastics Company, Inc. | Catalyst and process for making ethylene polymers |
| US5449850A (en) * | 1991-03-12 | 1995-09-12 | Exxon Chemical Patents Inc. | Process for oligomerizing C3 and higher olefins using zirconium adducts as catalysts (CS-467) |
| US5210338A (en) | 1991-10-25 | 1993-05-11 | Ethyl Corporation | Catalyzed chain growth process |
| US5221774A (en) * | 1992-03-19 | 1993-06-22 | Phillips Petroleum Company | Ethylene oligomerization |
| US5276220A (en) | 1992-06-18 | 1994-01-04 | Ethyl Corporation | Actinide catalyzed chain growth process |
| US5320993A (en) | 1992-07-17 | 1994-06-14 | Phillips Petroleum Company | Dimerization catalyst systems and processes |
| BE1006453A3 (nl) * | 1992-12-21 | 1994-08-30 | Dsm Nv | Katalysator en werkwijze voor een ziegler polymerisatie. |
| US5439862A (en) * | 1993-10-21 | 1995-08-08 | Kemp; Richard A. | Oligomerization catalyst and process |
| JP3847783B2 (ja) | 1995-01-24 | 2006-11-22 | イー・アイ・デュポン・ドゥ・ヌムール・アンド・カンパニー | オレフィンの重合方法 |
| US5714556A (en) | 1995-06-30 | 1998-02-03 | E. I. Dupont De Nemours And Company | Olefin polymerization process |
| IL129929A0 (en) | 1996-12-17 | 2000-02-29 | Du Pont | Polymerization of ethylene with specific iron or cobalt complexes novel pyridinebis (imines) and novel complexes of pyridinebis(imines) with iron and cobalt |
| KR100517852B1 (ko) | 1997-01-14 | 2005-09-30 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 올레핀 중합반응 |
| JP2002514252A (ja) | 1997-03-10 | 2002-05-14 | イーストマン ケミカル カンパニー | 第８〜１０族遷移金属を含むオレフィン重合触媒、二座配位子、このような触媒の使用方法及びそれから得られるポリマー |
| US6410664B1 (en) | 1997-03-24 | 2002-06-25 | Cryovac, Inc. | Catalyst compositions and processes for olefin polymers and copolymers |
| KR100516336B1 (ko) | 1997-09-05 | 2005-09-22 | 비피 케미칼즈 리미티드 | 중합 촉매 |
| JP3339441B2 (ja) * | 1999-01-11 | 2002-10-28 | 東ソー株式会社 | オレフィン重合体製造用触媒およびそれを用いたオレフィン重合体の製造方法 |
| EP0942006B1 (en) | 1998-03-09 | 2003-06-04 | Tosoh Corporation | Catalyst for olefin polymer production and process for olefin polymer production employing the catalyst |
| US6410660B1 (en) | 1998-03-27 | 2002-06-25 | E. I. Du Pont De Nemours And Company | Polymerization of olefins |
| US5932670A (en) * | 1998-03-30 | 1999-08-03 | Phillips Petroleum Company | Polymerization catalysts and processes therefor |
| GB9809207D0 (en) * | 1998-04-29 | 1998-07-01 | Bp Chem Int Ltd | Novel catalysts for olefin polymerisation |
| EP0967234A1 (en) * | 1998-06-24 | 1999-12-29 | Fina Research S.A. | Production of polyethylene |
| GB9817004D0 (en) * | 1998-08-06 | 1998-09-30 | Bp Chem Int Ltd | Preparation of polymerisation catalysts |
| GB9819847D0 (en) * | 1998-09-12 | 1998-11-04 | Bp Chem Int Ltd | Novel compounds |
| EP1159307B1 (en) * | 1998-11-30 | 2004-09-08 | BP Chemicals Limited | Polymerisation process |
| KR20010092241A (ko) * | 1999-01-22 | 2001-10-24 | 나까니시 히로유끼 | 올레핀 중합체의 제조 방법 및 올레핀 중합체 |
| GB9902697D0 (en) | 1999-02-09 | 1999-03-31 | Bp Chem Int Ltd | Novel compounds |
| WO2000050470A2 (en) | 1999-02-22 | 2000-08-31 | Eastman Chemical Company | Catalysts containing n-pyrrolyl substituted nitrogen donors |
| GB9928679D0 (en) * | 1999-12-03 | 2000-02-02 | Bp Chem Int Ltd | Polymerisation process |
| WO2001058966A1 (en) | 2000-02-10 | 2001-08-16 | Bp Chemicals Limited | Polymerisation catalyst |
| US6521724B2 (en) * | 2000-03-10 | 2003-02-18 | E. I. Du Pont De Nemours And Company | Polymerization process |
| US6501000B1 (en) * | 2000-04-04 | 2002-12-31 | Exxonmobil Research And Engineering Company | Late transition metal catalyst complexes and oligomers therefrom |
| NL1015608C2 (nl) | 2000-07-04 | 2002-01-08 | Duos B V | Inrichting en werkwijze voor het scheiden van heterogeen afval. |
| WO2002002144A1 (fr) | 2000-07-05 | 2002-01-10 | Takeda Chemical Industries, Ltd. | Preparations medicinales pour le traitement des maladies dependant des hormones sexuelles |
| RU2292343C2 (ru) * | 2001-08-01 | 2007-01-27 | Шелл Интернэшнл Рисерч Маатсхаппий Б.В. | Лиганды и включающие их каталитические системы для олигомеризации этилена с получением линейных альфа-олефинов |
| US7087686B2 (en) | 2001-08-06 | 2006-08-08 | Bp Chemicals Limited | Chain growth reaction process |
-
2001
- 2001-08-06 US US09/921,695 patent/US7087686B2/en not_active Expired - Lifetime
-
2002
- 2002-07-05 EA EA200400255A patent/EA007922B1/ru not_active IP Right Cessation
- 2002-07-05 CN CNB028194128A patent/CN100457695C/zh not_active Expired - Lifetime
- 2002-07-05 KR KR1020047001907A patent/KR100895599B1/ko not_active Expired - Fee Related
- 2002-07-05 EP EP02745584.9A patent/EP1414772B1/en not_active Expired - Lifetime
- 2002-07-05 EA EA200601455A patent/EA011711B1/ru not_active IP Right Cessation
- 2002-07-05 WO PCT/GB2002/003096 patent/WO2003014046A1/en not_active Ceased
- 2002-07-05 CN CN2007101264295A patent/CN101070261B/zh not_active Expired - Lifetime
- 2002-07-05 EP EP10179957.5A patent/EP2308815B1/en not_active Expired - Lifetime
- 2002-07-05 ES ES10179957T patent/ES2711251T3/es not_active Expired - Lifetime
- 2002-07-05 ES ES02745584.9T patent/ES2623164T3/es not_active Expired - Lifetime
- 2002-07-05 CA CA2456711A patent/CA2456711C/en not_active Expired - Lifetime
- 2002-07-05 JP JP2003519002A patent/JP2004537584A/ja active Pending
- 2002-08-02 MY MYPI20022909A patent/MY143732A/en unknown
-
2006
- 2006-06-28 US US11/476,206 patent/US7767771B2/en not_active Expired - Fee Related
-
2007
- 2007-01-31 US US11/700,111 patent/US7964681B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EA200400255A1 (ru) | 2004-10-28 |
| MY143732A (en) | 2011-07-15 |
| EP1414772A1 (en) | 2004-05-06 |
| KR100895599B1 (ko) | 2009-05-06 |
| ES2623164T3 (es) | 2017-07-10 |
| EP1414772B1 (en) | 2017-02-01 |
| JP2004537584A (ja) | 2004-12-16 |
| EA200601455A1 (ru) | 2006-12-29 |
| EA007922B1 (ru) | 2007-02-27 |
| EP2308815B1 (en) | 2018-11-14 |
| ES2711251T3 (es) | 2019-04-30 |
| US7767771B2 (en) | 2010-08-03 |
| CN101070261A (zh) | 2007-11-14 |
| US7964681B2 (en) | 2011-06-21 |
| WO2003014046A1 (en) | 2003-02-20 |
| EP2308815A1 (en) | 2011-04-13 |
| US7087686B2 (en) | 2006-08-08 |
| CA2456711A1 (en) | 2003-02-20 |
| KR20040032897A (ko) | 2004-04-17 |
| US20030078458A1 (en) | 2003-04-24 |
| CN100457695C (zh) | 2009-02-04 |
| EA011711B1 (ru) | 2009-04-28 |
| CN1561317A (zh) | 2005-01-05 |
| US20080200709A1 (en) | 2008-08-21 |
| CN101070261B (zh) | 2012-11-14 |
| US20070142656A1 (en) | 2007-06-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP1414772B1 (en) | Chain growth reaction process | |
| EP1091968B1 (en) | Production of half-sandwich substituted catalyst precursors | |
| US6825296B2 (en) | Catalyst component for olefin polymerization | |
| CN111662338B (zh) | 一类含中性胺或膦配位基侧基单茂第四副族金属配合物及其用途 | |
| CN107298727A (zh) | 一种双水杨醛亚胺‑蒽双金属钛催化剂的制备与应用 | |
| US6998363B2 (en) | Polyolefin catalyst component using non-covalent interactions | |
| CN118724966A (zh) | 一种含pnp配体的乙烯选择性四聚用催化体系及其制备方法与应用 | |
| CN104245712B (zh) | 乙烯低聚方法 | |
| EP1684901A4 (en) | LIGAND DIIMINE, METAL COMPOUND, OLEFIN POLYMERIZATION PROCESS | |
| US8426535B2 (en) | Chain growth reaction process | |
| US7105672B2 (en) | Cyclometallated catalysts | |
| CN111620914B (zh) | 含中性苄杂原子配位基侧臂单茂四价过渡金属配合物及其用途 | |
| Havlík et al. | Highly substituted zirconium and hafnium cyclopentadienyl bifunctional β-diketiminate complexes–Synthesis, structure, and catalytic activity towards ethylene polymerization | |
| Rahman | Zwitterionic Late Transition Metal Alkene Polymerisation Catalysts containing |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKEX | Expiry |
Effective date: 20220705 |