ES2197714T3 - Metalocenos de eslabon metileno como componentes cataliticos de la polimerizacion de olefinas. - Google Patents
Metalocenos de eslabon metileno como componentes cataliticos de la polimerizacion de olefinas.Info
- Publication number
- ES2197714T3 ES2197714T3 ES99972216T ES99972216T ES2197714T3 ES 2197714 T3 ES2197714 T3 ES 2197714T3 ES 99972216 T ES99972216 T ES 99972216T ES 99972216 T ES99972216 T ES 99972216T ES 2197714 T3 ES2197714 T3 ES 2197714T3
- Authority
- ES
- Spain
- Prior art keywords
- indenyl
- methylene
- substituents
- bis
- formula
- 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
- 238000006116 polymerization reaction Methods 0.000 title claims description 48
- 150000001336 alkenes Chemical class 0.000 title claims description 16
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 title claims description 5
- -1 METHYLENE METHYLENE Chemical class 0.000 title description 45
- 230000003197 catalytic effect Effects 0.000 title description 15
- 125000001424 substituent group Chemical group 0.000 claims abstract description 31
- 239000003446 ligand Substances 0.000 claims abstract description 18
- 125000004429 atom Chemical group 0.000 claims abstract description 10
- 230000000737 periodic effect Effects 0.000 claims abstract description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 8
- 150000002367 halogens Chemical class 0.000 claims abstract description 8
- 229910052751 metal Inorganic materials 0.000 claims abstract description 8
- 239000002184 metal Substances 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 7
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 5
- 230000003647 oxidation Effects 0.000 claims abstract description 4
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 4
- 229910052723 transition metal Inorganic materials 0.000 claims abstract description 4
- 150000003624 transition metals Chemical class 0.000 claims abstract description 4
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims abstract description 3
- 150000001255 actinides Chemical class 0.000 claims abstract description 3
- 125000000593 indol-1-yl group Chemical group [H]C1=C([H])C([H])=C2N([*])C([H])=C([H])C2=C1[H] 0.000 claims abstract description 3
- 229910052747 lanthanoid Inorganic materials 0.000 claims abstract description 3
- 150000002602 lanthanoids Chemical class 0.000 claims abstract description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 91
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 62
- 238000000034 method Methods 0.000 claims description 47
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 44
- 239000005977 Ethylene Substances 0.000 claims description 43
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 40
- 150000001875 compounds Chemical class 0.000 claims description 35
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 34
- 239000000203 mixture Substances 0.000 claims description 31
- 239000003054 catalyst Substances 0.000 claims description 26
- 239000002253 acid Substances 0.000 claims description 20
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 15
- 239000000178 monomer Substances 0.000 claims description 14
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 14
- 239000003426 co-catalyst Substances 0.000 claims description 13
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims description 12
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 9
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 8
- 229930040373 Paraformaldehyde Natural products 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- 239000012190 activator Substances 0.000 claims description 6
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 230000003213 activating effect Effects 0.000 claims description 5
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 5
- 150000001450 anions Chemical class 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 229910052726 zirconium Inorganic materials 0.000 claims description 4
- 239000000010 aprotic solvent Substances 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 229910052735 hafnium Inorganic materials 0.000 claims description 3
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- XSXHWVKGUXMUQE-UHFFFAOYSA-N osmium dioxide Inorganic materials O=[Os]=O XSXHWVKGUXMUQE-UHFFFAOYSA-N 0.000 claims description 2
- 229920002866 paraformaldehyde Polymers 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 claims 1
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 abstract 2
- 125000006736 (C6-C20) aryl group Chemical group 0.000 abstract 2
- 229910052768 actinide Inorganic materials 0.000 abstract 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 61
- 239000000243 solution Substances 0.000 description 61
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 53
- 230000015572 biosynthetic process Effects 0.000 description 49
- 238000003786 synthesis reaction Methods 0.000 description 49
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 40
- AQZWEFBJYQSQEH-UHFFFAOYSA-N 2-methyloxaluminane Chemical compound C[Al]1CCCCO1 AQZWEFBJYQSQEH-UHFFFAOYSA-N 0.000 description 39
- 238000006243 chemical reaction Methods 0.000 description 39
- 238000003756 stirring Methods 0.000 description 38
- 239000000725 suspension Substances 0.000 description 33
- 229910007926 ZrCl Inorganic materials 0.000 description 32
- 239000000047 product Substances 0.000 description 31
- 238000005481 NMR spectroscopy Methods 0.000 description 26
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 22
- 229920000642 polymer Polymers 0.000 description 22
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 239000000843 powder Substances 0.000 description 18
- 239000002904 solvent Substances 0.000 description 16
- 238000004458 analytical method Methods 0.000 description 15
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 15
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
- 239000007788 liquid Substances 0.000 description 12
- 238000003760 magnetic stirring Methods 0.000 description 12
- 238000005406 washing Methods 0.000 description 12
- 229910052782 aluminium Inorganic materials 0.000 description 11
- 238000000605 extraction Methods 0.000 description 11
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 11
- 239000004698 Polyethylene Substances 0.000 description 10
- VBDPXNNRCIXHFT-UHFFFAOYSA-N 2-(1h-inden-2-ylmethyl)-1h-indene Chemical compound C1=CC=C2CC(CC=3CC4=CC=CC=C4C=3)=CC2=C1 VBDPXNNRCIXHFT-UHFFFAOYSA-N 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- 239000004711 α-olefin Substances 0.000 description 9
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 7
- XBKNMGUCKSFTGE-UHFFFAOYSA-N 3-methyl-2-[(3-methyl-1h-inden-2-yl)methyl]-1h-indene Chemical compound C1C2=CC=CC=C2C(C)=C1CC1=C(C)C2=CC=CC=C2C1 XBKNMGUCKSFTGE-UHFFFAOYSA-N 0.000 description 7
- VCFGYRFNVFQFEH-UHFFFAOYSA-N 3-tert-butyl-2-[(3-tert-butyl-1h-inden-2-yl)methyl]-1h-indene Chemical compound C1C2=CC=CC=C2C(C(C)(C)C)=C1CC1=C(C(C)(C)C)C2=CC=CC=C2C1 VCFGYRFNVFQFEH-UHFFFAOYSA-N 0.000 description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 7
- 239000012141 concentrate Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- XZARRWQFNYUZBC-UHFFFAOYSA-L [Cl-].[Cl-].C1=CC=C2C(C(C)(C)C)C([Zr+2](=C)C=3C(C4=CC=CC=C4C=3)C(C)(C)C)=CC2=C1 Chemical compound [Cl-].[Cl-].C1=CC=C2C(C(C)(C)C)C([Zr+2](=C)C=3C(C4=CC=CC=C4C=3)C(C)(C)C)=CC2=C1 XZARRWQFNYUZBC-UHFFFAOYSA-L 0.000 description 6
- 229920000573 polyethylene Polymers 0.000 description 6
- 235000017557 sodium bicarbonate Nutrition 0.000 description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 6
- 229920002554 vinyl polymer Polymers 0.000 description 6
- VLZCLFQHRXRCFF-UHFFFAOYSA-N 2-[(4,7-dimethyl-1h-inden-2-yl)methyl]-4,7-dimethyl-1h-indene Chemical compound CC1=CC=C(C)C2=C1CC(CC1=CC=3C(C)=CC=C(C=3C1)C)=C2 VLZCLFQHRXRCFF-UHFFFAOYSA-N 0.000 description 5
- 241000349731 Afzelia bipindensis Species 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
- 238000012512 characterization method Methods 0.000 description 5
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- IHLVCKWPAMTVTG-UHFFFAOYSA-N lithium;carbanide Chemical compound [Li+].[CH3-] IHLVCKWPAMTVTG-UHFFFAOYSA-N 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 229910001220 stainless steel Inorganic materials 0.000 description 5
- 239000010935 stainless steel Substances 0.000 description 5
- 239000001993 wax Substances 0.000 description 5
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- UBWRPKIGXGLXBY-UHFFFAOYSA-L [Cl-].[Cl-].C1=CC=C2CC([Zr+2](C=3CC4=CC=CC=C4C=3)=C)=CC2=C1 Chemical compound [Cl-].[Cl-].C1=CC=C2CC([Zr+2](C=3CC4=CC=CC=C4C=3)=C)=CC2=C1 UBWRPKIGXGLXBY-UHFFFAOYSA-L 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 238000007334 copolymerization reaction Methods 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 238000004817 gas chromatography Methods 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
- 239000005022 packaging material Substances 0.000 description 4
- 238000010926 purge Methods 0.000 description 4
- LOWMZVPYBMDIBG-UHFFFAOYSA-N 3-phenyl-2-[(3-phenyl-1h-inden-2-yl)methyl]-1h-indene Chemical compound C=1C=CC=CC=1C=1C2=CC=CC=C2CC=1CC(CC1=CC=CC=C11)=C1C1=CC=CC=C1 LOWMZVPYBMDIBG-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- BSRUXPIXXVJQRG-UHFFFAOYSA-N [2-[(3-diphenylphosphanyl-1h-inden-2-yl)methyl]-3h-inden-1-yl]-diphenylphosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)C=1C2=CC=CC=C2CC=1CC(CC1=CC=CC=C11)=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 BSRUXPIXXVJQRG-UHFFFAOYSA-N 0.000 description 3
- QXZCNXSTDKFSRH-UHFFFAOYSA-L [Cl-].[Cl-].C1=CC=C2C(C)C([Zr+2](=C)C=3C(C4=CC=CC=C4C=3)C)=CC2=C1 Chemical compound [Cl-].[Cl-].C1=CC=C2C(C)C([Zr+2](=C)C=3C(C4=CC=CC=C4C=3)C)=CC2=C1 QXZCNXSTDKFSRH-UHFFFAOYSA-L 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 229920001155 polypropylene Polymers 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- JZVSOQUJGPAPJK-UHFFFAOYSA-N trimethyl-[3-methyl-2-[(3-methyl-1-trimethylsilyl-1h-inden-2-yl)methyl]-1h-inden-1-yl]silane Chemical compound C[Si](C)(C)C1C2=CC=CC=C2C(C)=C1CC1=C(C)C2=CC=CC=C2C1[Si](C)(C)C JZVSOQUJGPAPJK-UHFFFAOYSA-N 0.000 description 3
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 3
- XZIKSWMNFLIAQP-UHFFFAOYSA-N tris(2,4,4-trimethylpentyl)alumane Chemical compound CC(C)(C)CC(C)C[Al](CC(C)CC(C)(C)C)CC(C)CC(C)(C)C XZIKSWMNFLIAQP-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- WBZVXZGPXBXMSC-UHFFFAOYSA-N 2,5,6,6-tetrakis(2-methylpropyl)oxaluminane Chemical compound CC(C)CC1CC[Al](CC(C)C)OC1(CC(C)C)CC(C)C WBZVXZGPXBXMSC-UHFFFAOYSA-N 0.000 description 2
- COOKKJGOGWACMY-UHFFFAOYSA-N 3-methyl-1h-indene Chemical compound C1=CC=C2C(C)=CCC2=C1 COOKKJGOGWACMY-UHFFFAOYSA-N 0.000 description 2
- DKLQZDIAQKGVTA-UHFFFAOYSA-N 4,7-dimethyl-1h-indene Chemical compound CC1=CC=C(C)C2=C1CC=C2 DKLQZDIAQKGVTA-UHFFFAOYSA-N 0.000 description 2
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000007832 Na2SO4 Substances 0.000 description 2
- 241000940835 Pales Species 0.000 description 2
- 206010033546 Pallor Diseases 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 2
- 229910007932 ZrCl4 Inorganic materials 0.000 description 2
- WMHPECCQOOBCDJ-UHFFFAOYSA-L [Cl-].[Cl-].C1=CC=C2C([Si](C)(C)C)C([Zr+2](=C)C3=C(C4=CC=CC=C4C3[Si](C)(C)C)C)=C(C)C2=C1 Chemical compound [Cl-].[Cl-].C1=CC=C2C([Si](C)(C)C)C([Zr+2](=C)C3=C(C4=CC=CC=C4C3[Si](C)(C)C)C)=C(C)C2=C1 WMHPECCQOOBCDJ-UHFFFAOYSA-L 0.000 description 2
- WFKQLHXTJWZRFU-UHFFFAOYSA-L [Cl-].[Cl-].C1=CC=C2C([Si](C)(C)C)C([Zr+2](=C)C=3C(C4=CC=CC=C4C=3)[Si](C)(C)C)=CC2=C1 Chemical compound [Cl-].[Cl-].C1=CC=C2C([Si](C)(C)C)C([Zr+2](=C)C=3C(C4=CC=CC=C4C=3)[Si](C)(C)C)=CC2=C1 WFKQLHXTJWZRFU-UHFFFAOYSA-L 0.000 description 2
- JWBWPEWZKRDMBC-UHFFFAOYSA-L [Cl-].[Cl-].C=1C2=CC=CC=C2C(C=2C=CC=CC=2)C=1[Zr+2](=C)C1=CC2=CC=CC=C2C1C1=CC=CC=C1 Chemical compound [Cl-].[Cl-].C=1C2=CC=CC=C2C(C=2C=CC=CC=2)C=1[Zr+2](=C)C1=CC2=CC=CC=C2C1C1=CC=CC=C1 JWBWPEWZKRDMBC-UHFFFAOYSA-L 0.000 description 2
- JJXHBJJGFYFIPM-UHFFFAOYSA-L [Cl-].[Cl-].C=1C2=CC=CC=C2C(P(C=2C=CC=CC=2)C=2C=CC=CC=2)C=1[Zr+2](=C)C1=CC2=CC=CC=C2C1P(C=1C=CC=CC=1)C1=CC=CC=C1 Chemical compound [Cl-].[Cl-].C=1C2=CC=CC=C2C(P(C=2C=CC=CC=2)C=2C=CC=CC=2)C=1[Zr+2](=C)C1=CC2=CC=CC=C2C1P(C=1C=CC=CC=1)C1=CC=CC=C1 JJXHBJJGFYFIPM-UHFFFAOYSA-L 0.000 description 2
- UVPDGFZJZYLLEK-UHFFFAOYSA-L [Cl-].[Cl-].CC1=CC=C(C)C2=C1CC([Zr+2](=C)C1=CC=3C(C)=CC=C(C=3C1)C)=C2 Chemical compound [Cl-].[Cl-].CC1=CC=C(C)C2=C1CC([Zr+2](=C)C1=CC=3C(C)=CC=C(C=3C1)C)=C2 UVPDGFZJZYLLEK-UHFFFAOYSA-L 0.000 description 2
- 239000002168 alkylating agent Substances 0.000 description 2
- 229940100198 alkylating agent Drugs 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 230000002902 bimodal effect Effects 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000002826 coolant Substances 0.000 description 2
- YMWUJEATGCHHMB-DICFDUPASA-N dichloromethane-d2 Chemical compound [2H]C([2H])(Cl)Cl YMWUJEATGCHHMB-DICFDUPASA-N 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 230000004927 fusion Effects 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 229920000098 polyolefin Polymers 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 2
- RQHQKLNZXIIKLE-UHFFFAOYSA-N trimethyl-[2-[(1-trimethylsilyl-1h-inden-2-yl)methyl]-1h-inden-1-yl]silane Chemical compound C1=CC=C2C([Si](C)(C)C)C(CC=3C(C4=CC=CC=C4C=3)[Si](C)(C)C)=CC2=C1 RQHQKLNZXIIKLE-UHFFFAOYSA-N 0.000 description 2
- HKVFGFGPRISDFM-UHFFFAOYSA-N tris(2,3,3-trimethylbutyl)alumane Chemical compound CC(C)(C)C(C)C[Al](CC(C)C(C)(C)C)CC(C)C(C)(C)C HKVFGFGPRISDFM-UHFFFAOYSA-N 0.000 description 2
- SSEXLBWMXFFGTD-UHFFFAOYSA-N tris(2,3-dimethylbutyl)alumane Chemical compound CC(C)C(C)C[Al](CC(C)C(C)C)CC(C)C(C)C SSEXLBWMXFFGTD-UHFFFAOYSA-N 0.000 description 2
- DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical compound Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 0.000 description 2
- ZYECOAILUNWEAL-NUDFZHEQSA-N (4z)-4-[[2-methoxy-5-(phenylcarbamoyl)phenyl]hydrazinylidene]-n-(3-nitrophenyl)-3-oxonaphthalene-2-carboxamide Chemical compound COC1=CC=C(C(=O)NC=2C=CC=CC=2)C=C1N\N=C(C1=CC=CC=C1C=1)/C(=O)C=1C(=O)NC1=CC=CC([N+]([O-])=O)=C1 ZYECOAILUNWEAL-NUDFZHEQSA-N 0.000 description 1
- QVLAWKAXOMEXPM-DICFDUPASA-N 1,1,1,2-tetrachloro-2,2-dideuterioethane Chemical compound [2H]C([2H])(Cl)C(Cl)(Cl)Cl QVLAWKAXOMEXPM-DICFDUPASA-N 0.000 description 1
- CHRJZRDFSQHIFI-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;styrene Chemical compound C=CC1=CC=CC=C1.C=CC1=CC=CC=C1C=C CHRJZRDFSQHIFI-UHFFFAOYSA-N 0.000 description 1
- PRBHEGAFLDMLAL-UHFFFAOYSA-N 1,5-Hexadiene Natural products CC=CCC=C PRBHEGAFLDMLAL-UHFFFAOYSA-N 0.000 description 1
- UAGSWZGMVQXQKB-UHFFFAOYSA-N 1-cyclopenta-2,4-dien-1-yl-1H-indene zirconium(2+) Chemical class [Zr++].C1=Cc2ccccc2C1[c-]1cccc1.C1=Cc2ccccc2C1[c-]1cccc1 UAGSWZGMVQXQKB-UHFFFAOYSA-N 0.000 description 1
- PXORBAGTGTXORO-UHFFFAOYSA-N 1-phenyl-1h-indene Chemical compound C1=CC2=CC=CC=C2C1C1=CC=CC=C1 PXORBAGTGTXORO-UHFFFAOYSA-N 0.000 description 1
- IHHBPJRQKRVWAY-UHFFFAOYSA-N 1-tert-butyl-1h-indene Chemical compound C1=CC=C2C(C(C)(C)C)C=CC2=C1 IHHBPJRQKRVWAY-UHFFFAOYSA-N 0.000 description 1
- VDBSCMJCMSNQQB-UHFFFAOYSA-N 2-methylpropyl-bis(2,4,4-trimethylpentyl)alumane Chemical compound CC(C)(C)CC(C)C[Al](CC(C)C)CC(C)CC(C)(C)C VDBSCMJCMSNQQB-UHFFFAOYSA-N 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- 240000007124 Brassica oleracea Species 0.000 description 1
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 1
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 1
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 1
- IFWCYWVFYXRAQG-UHFFFAOYSA-N C(C(C)C)[AlH]CC(C)C.[AlH3] Chemical compound C(C(C)C)[AlH]CC(C)C.[AlH3] IFWCYWVFYXRAQG-UHFFFAOYSA-N 0.000 description 1
- ICQRTUOHQBZTGT-UHFFFAOYSA-N C(C)C1C(=CC2=CC=CC=C12)[Zr] Chemical compound C(C)C1C(=CC2=CC=CC=C12)[Zr] ICQRTUOHQBZTGT-UHFFFAOYSA-N 0.000 description 1
- HOZGGOHINMFWKT-UHFFFAOYSA-N CC1C([Zr])=Cc2ccccc12 Chemical compound CC1C([Zr])=Cc2ccccc12 HOZGGOHINMFWKT-UHFFFAOYSA-N 0.000 description 1
- VSXGSGYGSHFRAN-UHFFFAOYSA-N CCl.CC1C(=Cc2ccccc12)[Zr](=C)C1=Cc2ccccc2C1C Chemical compound CCl.CC1C(=Cc2ccccc12)[Zr](=C)C1=Cc2ccccc2C1C VSXGSGYGSHFRAN-UHFFFAOYSA-N 0.000 description 1
- 101100219382 Caenorhabditis elegans cah-2 gene Proteins 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 229910010084 LiAlH4 Inorganic materials 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 238000010478 Prins reaction Methods 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 229910007928 ZrCl2 Inorganic materials 0.000 description 1
- OJAJBEQXNXKTIK-UHFFFAOYSA-N [Zr]C(CC1=CC=C2)=CC1=C2C1=CC=CC=C1 Chemical compound [Zr]C(CC1=CC=C2)=CC1=C2C1=CC=CC=C1 OJAJBEQXNXKTIK-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 150000004791 alkyl magnesium halides Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 125000005018 aryl alkenyl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- DSDJNWYBXQXLRZ-UHFFFAOYSA-N bis(2,4,4-trimethylpentyl)aluminum Chemical compound CC(C)(C)CC(C)C[Al]CC(C)CC(C)(C)C DSDJNWYBXQXLRZ-UHFFFAOYSA-N 0.000 description 1
- UXPLEHPMOSDYLZ-UHFFFAOYSA-N bis(2-methylpropyl)-(2,4,4-trimethylpentyl)alumane Chemical compound CC(C)C[Al](CC(C)C)CC(C)CC(C)(C)C UXPLEHPMOSDYLZ-UHFFFAOYSA-N 0.000 description 1
- KILPPHWPVWEKTE-UHFFFAOYSA-N bis(2-methylpropyl)-(2-phenylpropyl)alumane Chemical compound CC(C)C[Al](CC(C)C)CC(C)C1=CC=CC=C1 KILPPHWPVWEKTE-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229940045348 brown mixture Drugs 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- XGRJZXREYAXTGV-UHFFFAOYSA-N chlorodiphenylphosphine Chemical compound C=1C=CC=CC=1P(Cl)C1=CC=CC=C1 XGRJZXREYAXTGV-UHFFFAOYSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 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
- 238000007872 degassing Methods 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- ISEJRLXHKSHKPM-UHFFFAOYSA-N dimethyl(2-methylpropyl)alumane Chemical compound CC(C)C[Al](C)C ISEJRLXHKSHKPM-UHFFFAOYSA-N 0.000 description 1
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 1
- 238000012685 gas phase polymerization Methods 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical compound C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 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
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000004540 pour-on Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011403 purification operation Methods 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000010902 straw Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- MCWWHQMTJNSXPX-UHFFFAOYSA-N tribenzylalumane Chemical compound C=1C=CC=CC=1C[Al](CC=1C=CC=CC=1)CC1=CC=CC=C1 MCWWHQMTJNSXPX-UHFFFAOYSA-N 0.000 description 1
- VJJYNHGCCSVYLS-UHFFFAOYSA-N trimethyl-[2-[(3-trimethylsilyl-1h-inden-2-yl)methyl]-3h-inden-1-yl]silane Chemical compound C1C2=CC=CC=C2C([Si](C)(C)C)=C1CC1=C([Si](C)(C)C)C2=CC=CC=C2C1 VJJYNHGCCSVYLS-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- VGONMIOMLRCRSS-UHFFFAOYSA-N tris(2,3-dimethylhexyl)alumane Chemical compound CCCC(C)C(C)C[Al](CC(C)C(C)CCC)CC(C)C(C)CCC VGONMIOMLRCRSS-UHFFFAOYSA-N 0.000 description 1
- BENYMJNPVWYYES-UHFFFAOYSA-N tris(2,3-dimethylpentyl)alumane Chemical compound CCC(C)C(C)C[Al](CC(C)C(C)CC)CC(C)C(C)CC BENYMJNPVWYYES-UHFFFAOYSA-N 0.000 description 1
- UVCGXEXDZCCTFF-UHFFFAOYSA-N tris(2,4-dimethylheptyl)alumane Chemical compound CCCC(C)CC(C)C[Al](CC(C)CC(C)CCC)CC(C)CC(C)CCC UVCGXEXDZCCTFF-UHFFFAOYSA-N 0.000 description 1
- FEJNOSHLGDRZDX-UHFFFAOYSA-N tris(2-ethyl-3-methylbutyl)alumane Chemical compound CCC(C(C)C)C[Al](CC(CC)C(C)C)CC(CC)C(C)C FEJNOSHLGDRZDX-UHFFFAOYSA-N 0.000 description 1
- JAFSWBPCWFKGBY-UHFFFAOYSA-N tris(2-ethyl-3-methylpentyl)alumane Chemical compound CCC(C)C(CC)C[Al](CC(CC)C(C)CC)CC(CC)C(C)CC JAFSWBPCWFKGBY-UHFFFAOYSA-N 0.000 description 1
- AMPVHNIRJXJXEN-UHFFFAOYSA-N tris(3-ethyl-2-methylpentyl)alumane Chemical compound CCC(CC)C(C)C[Al](CC(C)C(CC)CC)CC(C)C(CC)CC AMPVHNIRJXJXEN-UHFFFAOYSA-N 0.000 description 1
- VIDMRZMJMLMHSP-UHFFFAOYSA-N tris(3-methyl-2-propan-2-ylbutyl)alumane Chemical compound CC(C)C(C(C)C)C[Al](CC(C(C)C)C(C)C)CC(C(C)C)C(C)C VIDMRZMJMLMHSP-UHFFFAOYSA-N 0.000 description 1
- MLDSMTVYPPIXMZ-UHFFFAOYSA-N tris(4-methylpentyl)alumane Chemical compound CC(C)CCC[Al](CCCC(C)C)CCCC(C)C MLDSMTVYPPIXMZ-UHFFFAOYSA-N 0.000 description 1
- 229910052845 zircon Inorganic materials 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
- C07C2/86—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon
- C07C2/862—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon the non-hydrocarbon contains only oxygen as hetero-atoms
- C07C2/867—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon the non-hydrocarbon contains only oxygen as hetero-atoms the non-hydrocarbon is an aldehyde or a ketone
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/45—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with a bicyclo ring system containing nine carbon atoms
- C07C13/465—Indenes; Completely or partially hydrogenated indenes
-
- 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
- C07F17/00—Metallocenes
-
- 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
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
-
- 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
- C08F110/00—Homopolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F110/02—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
- C08F110/00—Homopolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F110/04—Monomers containing three or four carbon atoms
- C08F110/06—Propene
-
- 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
-
- 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)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP98203906 | 1998-11-18 | ||
| EP98203906 | 1998-11-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2197714T3 true ES2197714T3 (es) | 2004-01-01 |
Family
ID=8234358
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES99972216T Expired - Lifetime ES2197714T3 (es) | 1998-11-18 | 1999-11-10 | Metalocenos de eslabon metileno como componentes cataliticos de la polimerizacion de olefinas. |
Country Status (12)
| Country | Link |
|---|---|
| US (2) | US6693156B1 (enExample) |
| EP (1) | EP1131328B1 (enExample) |
| JP (1) | JP2002530285A (enExample) |
| KR (1) | KR20010101034A (enExample) |
| AR (1) | AR021312A1 (enExample) |
| AU (1) | AU1382200A (enExample) |
| BR (1) | BR9916740A (enExample) |
| CA (1) | CA2350542A1 (enExample) |
| DE (1) | DE69907721T2 (enExample) |
| ES (1) | ES2197714T3 (enExample) |
| IL (1) | IL142979A0 (enExample) |
| WO (1) | WO2000029415A1 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6559251B1 (en) * | 2002-08-02 | 2003-05-06 | Equistar Chemicals, Lp | Process for making low-density polyolefins |
| WO2010022878A1 (en) * | 2008-08-25 | 2010-03-04 | Basell Polyolefine Gmbh | Preparation of ansa metallocene compounds |
| KR20140075589A (ko) | 2012-12-11 | 2014-06-19 | 주식회사 엘지화학 | 신규한 리간드 화합물, 이의 제조방법, 전이금속 화합물, 및 이의 제조방법 |
| WO2014092327A1 (ko) | 2012-12-11 | 2014-06-19 | 주식회사 엘지화학 | 신규한 리간드 화합물, 이의 제조방법 및 상기 리간드 화합물을 포함하는 전이금속 화합물, 및 이의 제조방법 |
| JP6326202B2 (ja) * | 2013-05-16 | 2018-05-16 | 三井化学株式会社 | オレフィン重合用固体触媒成分およびそれを用いたオレフィン系重合体の製造方法 |
| CN110650965B (zh) | 2017-04-04 | 2022-10-04 | Sabic环球技术有限责任公司 | 用于烯烃聚合的二烃基-甲硅烷基-桥连-1,3二取代-2-茚基茂金属络合物 |
| CN110650978B (zh) * | 2017-04-04 | 2022-09-23 | Sabic环球技术有限责任公司 | 用于烯烃聚合的二甲基-甲硅烷基-桥连的-1-取代-2-茚基茂金属复合物 |
| EP3743431B1 (en) | 2018-01-24 | 2025-04-16 | SABIC Global Technologies B.V. | 1,2-phenylene bridged 1-indenyl-2-indenyl metallocene complexes for olefin polymerisation |
| EP4110834B1 (en) * | 2020-02-24 | 2024-04-03 | ExxonMobil Chemical Patents Inc. | Ansa-bis(inden-2-yl) catalysts for producing vinylidene-terminated polyalphaolefins |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3840772A1 (de) | 1988-12-03 | 1990-06-07 | Hoechst Ag | Verfahren zur herstellung einer heterogenen metallocenkatalysatorkomponente |
| ES2071888T3 (es) | 1990-11-12 | 1995-07-01 | Hoechst Ag | Bisindenilmetalocenos sustituidos en posicion 2, procedimiento para su preparacion y su utilizacion como catalizadores en la polimerizacion de olefinas. |
| IL106042A (en) | 1992-06-18 | 1999-05-09 | Montell Technology Company Bv | Catalysts for the polymerization of olefins obtained from organometallic cyclopentadienyl compounds alumino-organic compounds and water and process for the preparation of an ethylene homo- and copolymer |
| NL9201970A (nl) * | 1992-11-11 | 1994-06-01 | Dsm Nv | Indenylverbindingen en katalysatorcomponenten voor de polymerisatie van olefinen. |
| IT1273661B (it) | 1994-07-20 | 1997-07-09 | Spherilene Srl | Catalizzatori per la polimerizzazione delle olefine |
| IT1272924B (it) | 1995-01-23 | 1997-07-01 | Spherilene Srl | Procedimento per la preparazione di composti ciclopentadienilici e composti cosi' ottenibili |
| DE19637669A1 (de) * | 1996-09-16 | 1998-03-19 | Hoechst Ag | Verfahren zur Herstellung einer methylenverbrückten Biscyclopentadienylverbindung |
| DE69803652T2 (de) * | 1997-03-29 | 2002-08-14 | Basell Technology Co. B.V., Hoofddorp | Verfahren zur herstellung von cyclopentadienylverbindungen |
| US6559252B1 (en) | 1997-10-29 | 2003-05-06 | Basell Technology Company Bv | Catalysts and processes for the polymerization of olefins |
| CA2283880A1 (en) | 1998-01-14 | 1999-07-22 | Montell Technology Company B.V. | Process for the preparation of metallocene compounds |
| EP1214364B1 (en) | 1999-09-22 | 2003-07-16 | Basell Polyolefine GmbH | Catalyst system and process for the polymerization of olefins |
-
1999
- 1999-11-10 DE DE69907721T patent/DE69907721T2/de not_active Expired - Fee Related
- 1999-11-10 KR KR1020017006322A patent/KR20010101034A/ko not_active Withdrawn
- 1999-11-10 EP EP99972216A patent/EP1131328B1/en not_active Expired - Lifetime
- 1999-11-10 ES ES99972216T patent/ES2197714T3/es not_active Expired - Lifetime
- 1999-11-10 IL IL14297999A patent/IL142979A0/xx unknown
- 1999-11-10 WO PCT/EP1999/008646 patent/WO2000029415A1/en not_active Ceased
- 1999-11-10 JP JP2000582402A patent/JP2002530285A/ja active Pending
- 1999-11-10 CA CA002350542A patent/CA2350542A1/en not_active Abandoned
- 1999-11-10 BR BR9916740-9A patent/BR9916740A/pt not_active Application Discontinuation
- 1999-11-10 US US09/831,960 patent/US6693156B1/en not_active Expired - Fee Related
- 1999-11-10 AU AU13822/00A patent/AU1382200A/en not_active Abandoned
- 1999-11-18 AR ARP990105862A patent/AR021312A1/es unknown
-
2003
- 2003-12-16 US US10/737,097 patent/US6872863B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CA2350542A1 (en) | 2000-05-25 |
| JP2002530285A (ja) | 2002-09-17 |
| WO2000029415A1 (en) | 2000-05-25 |
| EP1131328A1 (en) | 2001-09-12 |
| AU1382200A (en) | 2000-06-05 |
| US6872863B2 (en) | 2005-03-29 |
| EP1131328B1 (en) | 2003-05-07 |
| US20040147695A1 (en) | 2004-07-29 |
| DE69907721T2 (de) | 2004-02-26 |
| BR9916740A (pt) | 2001-08-21 |
| AR021312A1 (es) | 2002-07-17 |
| US6693156B1 (en) | 2004-02-17 |
| DE69907721D1 (de) | 2003-06-12 |
| IL142979A0 (en) | 2002-04-21 |
| KR20010101034A (ko) | 2001-11-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU2245341C2 (ru) | Металлоценовые соединения, способ их получения, катализатор полимеризации олефинов, способ полимеризации | |
| ES2221744T3 (es) | Proceso para la fabricacion de copolimeros de etileno con alfa-olefinas. | |
| US6268518B1 (en) | Metallocene compounds and their use in catalysts for the polymerization of olefins | |
| JP4383549B2 (ja) | オレフィンの重合用触媒及びその方法 | |
| ES2341453T3 (es) | Compuesto de metal de transicion organometalico, sistema de ligando de bisciclopentadienilo, sistema catalitico y preparacion de poliolefinas. | |
| RU2243229C2 (ru) | Металлоценовое соединение, лиганд, способы получения лиганда, катализатор, способ получения полимера альфа-олефинов, гомополимер пропилена, сополимер пропилена | |
| ITMI941517A1 (it) | Procedimento per la preparazione di polimeri amorfi del propilene | |
| ITMI940645A1 (it) | Composti metallocenici, procedimento per la preparazione e loro utilizzo in catalizzatori per la polimerizzazione delle olefine | |
| ITMI951444A1 (it) | Catalizzatore metallocenico per la (co) polimerizzazione delle olefine | |
| KR20020034193A (ko) | 올레핀 중합을 위한 촉매 시스템 및 방법 | |
| EP1047702B1 (en) | Bis(tetrahyydro-indenyl) metallocenes as olefin-polymerization- catalyst | |
| JP2006512410A (ja) | 有機金属遷移金属化合物、ビスシクロペンタジエニル配位子を有する化合物、触媒組成物、及びこれらを用いたポリオレフィンの製造法 | |
| ITMI950410A1 (it) | Composti metallocenici bis-fluorenilici procedimento per la loro preparazione e loro utilizzo in catalizzatori per la polimerizzazione | |
| WO2000031088A1 (en) | Bridged metallocenes, preparation, use in catalytic systems | |
| ES2197714T3 (es) | Metalocenos de eslabon metileno como componentes cataliticos de la polimerizacion de olefinas. | |
| ITMI951118A1 (it) | Composti metallocenici bis-indenilici pontanti procedimento per la loro preparazione e loro utilizzo in catalizzatori per la | |
| JP3461539B2 (ja) | エチレンとオレフィン系モノマーとの共重合体とその製法及び触媒 | |
| EP1059300A1 (en) | Indenyl compounds for the polymerisation of olefins | |
| KR20000016125A (ko) | 메탈로센 및 올레핀 중합용 촉매_ | |
| MXPA98010099A (en) | Metallocenes and catalysts for polymerization of olefins | |
| ITMI942567A1 (it) | Polimero del propilene e procedimento per la sua preparazione |