JPH11106392A - ラセミ性アンサ−メタロセン錯体の製造方法 - Google Patents
ラセミ性アンサ−メタロセン錯体の製造方法Info
- Publication number
- JPH11106392A JPH11106392A JP10204061A JP20406198A JPH11106392A JP H11106392 A JPH11106392 A JP H11106392A JP 10204061 A JP10204061 A JP 10204061A JP 20406198 A JP20406198 A JP 20406198A JP H11106392 A JPH11106392 A JP H11106392A
- Authority
- JP
- Japan
- Prior art keywords
- group
- alkyl
- aryl
- dimethylsilanediylbis
- dichloride
- 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.)
- Withdrawn
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 44
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 23
- 150000003606 tin compounds Chemical class 0.000 claims abstract description 18
- 125000005843 halogen group Chemical group 0.000 claims abstract description 13
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 13
- 125000003118 aryl group Chemical group 0.000 claims abstract description 12
- 229910052732 germanium Inorganic materials 0.000 claims abstract description 9
- 229910052726 zirconium Inorganic materials 0.000 claims abstract description 9
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical group [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910052735 hafnium Inorganic materials 0.000 claims abstract description 8
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical group [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052719 titanium Inorganic materials 0.000 claims abstract description 7
- 239000010936 titanium Substances 0.000 claims abstract description 7
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical group [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052758 niobium Inorganic materials 0.000 claims abstract description 5
- 239000010955 niobium Chemical group 0.000 claims abstract description 5
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical group [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052715 tantalum Chemical group 0.000 claims abstract description 5
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical group [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052720 vanadium Inorganic materials 0.000 claims abstract description 5
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical group [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 claims abstract description 5
- 150000003623 transition metal compounds Chemical class 0.000 claims abstract 2
- -1 iodine, hydrogen Chemical group 0.000 claims description 162
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 27
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 23
- 125000004407 fluoroaryl group Chemical group 0.000 claims description 16
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 15
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 14
- 125000001424 substituent group Chemical group 0.000 claims description 13
- 239000010703 silicon Substances 0.000 claims description 12
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 11
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 11
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 11
- 125000005018 aryl alkenyl group Chemical group 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 125000004122 cyclic group Chemical group 0.000 claims description 8
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000000460 chlorine Chemical group 0.000 claims description 4
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical class C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 4
- 125000004429 atom Chemical group 0.000 claims 4
- 150000001721 carbon Chemical group 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 239000011630 iodine Chemical group 0.000 claims 1
- 150000001336 alkenes Chemical class 0.000 abstract description 5
- 239000000203 mixture Substances 0.000 abstract description 4
- 229910052723 transition metal Inorganic materials 0.000 abstract description 4
- 150000003624 transition metals Chemical class 0.000 abstract description 4
- 239000003054 catalyst Substances 0.000 abstract description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 abstract description 3
- 238000006116 polymerization reaction Methods 0.000 abstract description 3
- 229910052736 halogen Inorganic materials 0.000 abstract 3
- 230000003197 catalytic effect Effects 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- ZWYDDDAMNQQZHD-UHFFFAOYSA-L titanium(ii) chloride Chemical compound [Cl-].[Cl-].[Ti+2] ZWYDDDAMNQQZHD-UHFFFAOYSA-L 0.000 description 58
- KUNZSLJMPCDOGI-UHFFFAOYSA-L [Cl-].[Cl-].[Hf+2] Chemical compound [Cl-].[Cl-].[Hf+2] KUNZSLJMPCDOGI-UHFFFAOYSA-L 0.000 description 42
- VPGLGRNSAYHXPY-UHFFFAOYSA-L zirconium(2+);dichloride Chemical compound Cl[Zr]Cl VPGLGRNSAYHXPY-UHFFFAOYSA-L 0.000 description 40
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 27
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 20
- UBHZUDXTHNMNLD-UHFFFAOYSA-N dimethylsilane Chemical compound C[SiH2]C UBHZUDXTHNMNLD-UHFFFAOYSA-N 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- 241000723368 Conium Species 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
- XOJVVFBFDXDTEG-UHFFFAOYSA-N pristane Chemical compound CC(C)CCCC(C)CCCC(C)CCCC(C)C XOJVVFBFDXDTEG-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 5
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 241001147389 Panthera uncia Species 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- BHXJYIYNCKAHNU-UHFFFAOYSA-L CCCC1=Cc2c(cccc2-c2ccccc2)C1[Zr](Cl)(Cl)(C1C(CCC)=Cc2c1cccc2-c1ccccc1)=[Si](C)C Chemical compound CCCC1=Cc2c(cccc2-c2ccccc2)C1[Zr](Cl)(Cl)(C1C(CCC)=Cc2c1cccc2-c1ccccc1)=[Si](C)C BHXJYIYNCKAHNU-UHFFFAOYSA-L 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 229910007926 ZrCl Inorganic materials 0.000 description 2
- BNAPOKTZSIWEPP-UHFFFAOYSA-L [Cl-].[Cl-].C[Si](=[Hf+2](C1C(=CC2=C(C=C(C=C12)CCC)CCC)CCC)C1C(=CC2=C(C=C(C=C12)CCC)CCC)CCC)C Chemical compound [Cl-].[Cl-].C[Si](=[Hf+2](C1C(=CC2=C(C=C(C=C12)CCC)CCC)CCC)C1C(=CC2=C(C=C(C=C12)CCC)CCC)CCC)C BNAPOKTZSIWEPP-UHFFFAOYSA-L 0.000 description 2
- DQFLAMDYBKVQCE-UHFFFAOYSA-L [Cl-].[Cl-].C[Si](=[Hf+2](C1C(=CC2=CC=CC=C12)CCC)C1C(=CC2=CC=CC=C12)CCC)C Chemical compound [Cl-].[Cl-].C[Si](=[Hf+2](C1C(=CC2=CC=CC=C12)CCC)C1C(=CC2=CC=CC=C12)CCC)C DQFLAMDYBKVQCE-UHFFFAOYSA-L 0.000 description 2
- SJWOUYXRSCYFHI-UHFFFAOYSA-L [Cl-].[Cl-].C[Si](=[Ti+2](C1=C(C=C(C1)C(C)(C)C)CCC)C1=C(C=C(C1)C(C)(C)C)CCC)C Chemical compound [Cl-].[Cl-].C[Si](=[Ti+2](C1=C(C=C(C1)C(C)(C)C)CCC)C1=C(C=C(C1)C(C)(C)C)CCC)C SJWOUYXRSCYFHI-UHFFFAOYSA-L 0.000 description 2
- WQTJLXZBCJZFIR-UHFFFAOYSA-L [Cl-].[Cl-].C[Si](=[Ti+2](C1C(=CC2=CC=CC=C12)CCC)C1C(=CC2=CC=CC=C12)CCC)C Chemical compound [Cl-].[Cl-].C[Si](=[Ti+2](C1C(=CC2=CC=CC=C12)CCC)C1C(=CC2=CC=CC=C12)CCC)C WQTJLXZBCJZFIR-UHFFFAOYSA-L 0.000 description 2
- NLYXUVNNXQDQLM-UHFFFAOYSA-L [Cl-].[Cl-].C[Si](=[Zr+2](C1=C(C=C(C1)CCCC)CCC)C1=C(C=C(C1)CCCC)CCC)C Chemical compound [Cl-].[Cl-].C[Si](=[Zr+2](C1=C(C=C(C1)CCCC)CCC)C1=C(C=C(C1)CCCC)CCC)C NLYXUVNNXQDQLM-UHFFFAOYSA-L 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 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
- WHXTVQNIFGXMSB-UHFFFAOYSA-N n-methyl-n-[tris(dimethylamino)stannyl]methanamine Chemical compound CN(C)[Sn](N(C)C)(N(C)C)N(C)C WHXTVQNIFGXMSB-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000007858 starting material Substances 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- VPOIWIHULPYZPS-UHFFFAOYSA-N CC1=CC(C(=CC=C2)C=3C=CC=CC=3)=C2C1[Zr](=[Si](C)C)C1C(C)=CC2=C1C=CC=C2C1=CC=CC=C1 Chemical compound CC1=CC(C(=CC=C2)C=3C=CC=CC=3)=C2C1[Zr](=[Si](C)C)C1C(C)=CC2=C1C=CC=C2C1=CC=CC=C1 VPOIWIHULPYZPS-UHFFFAOYSA-N 0.000 description 1
- NMIKJVQNDAONKK-UHFFFAOYSA-N CC=1C(C2=C(C=CC(=C2C=1)C)C)[Zr] Chemical compound CC=1C(C2=C(C=CC(=C2C=1)C)C)[Zr] NMIKJVQNDAONKK-UHFFFAOYSA-N 0.000 description 1
- PILUIKIPDDBMQQ-UHFFFAOYSA-N CCC(C=C(C1)[Si](C)(C)C)=C1[Ti](C(C1)=C(CC)C=C1[Si](C)(C)C)=[Si](C)C Chemical compound CCC(C=C(C1)[Si](C)(C)C)=C1[Ti](C(C1)=C(CC)C=C1[Si](C)(C)C)=[Si](C)C PILUIKIPDDBMQQ-UHFFFAOYSA-N 0.000 description 1
- TWIKNGNNDZHDQX-UHFFFAOYSA-L CCC1=CC2=C(C=CC=C2C1[Hf](Cl)(Cl)(C1C(CC)=CC2=C(C=CC=C12)C1=CC=CC2=CC=CC=C12)=[Si](C)C)C1=CC=CC2=CC=CC=C12 Chemical compound CCC1=CC2=C(C=CC=C2C1[Hf](Cl)(Cl)(C1C(CC)=CC2=C(C=CC=C12)C1=CC=CC2=CC=CC=C12)=[Si](C)C)C1=CC=CC2=CC=CC=C12 TWIKNGNNDZHDQX-UHFFFAOYSA-L 0.000 description 1
- FLILBDDKJYBRBU-UHFFFAOYSA-L CCC1=CC2=C(C=CC=C2C1[Ti](Cl)(Cl)(C1C(CC)=CC2=C(C=CC=C12)C1=CC=CC2=CC=CC=C12)=[Si](C)C)C1=CC=CC2=CC=CC=C12 Chemical compound CCC1=CC2=C(C=CC=C2C1[Ti](Cl)(Cl)(C1C(CC)=CC2=C(C=CC=C12)C1=CC=CC2=CC=CC=C12)=[Si](C)C)C1=CC=CC2=CC=CC=C12 FLILBDDKJYBRBU-UHFFFAOYSA-L 0.000 description 1
- BAUXJDGQWHWLOA-UHFFFAOYSA-L CCCC(C1)=CC(CCC)=C1[Ti+2].[Cl-].[Cl-] Chemical compound CCCC(C1)=CC(CCC)=C1[Ti+2].[Cl-].[Cl-] BAUXJDGQWHWLOA-UHFFFAOYSA-L 0.000 description 1
- XREJQMXBLFZXAH-UHFFFAOYSA-L CCCC1=Cc2c(cccc2-c2cccc3ccccc23)C1[Zr](Cl)(Cl)(C1C(CCC)=Cc2c1cccc2-c1cccc2ccccc12)=[Si](C)C Chemical compound CCCC1=Cc2c(cccc2-c2cccc3ccccc23)C1[Zr](Cl)(Cl)(C1C(CCC)=Cc2c1cccc2-c1cccc2ccccc12)=[Si](C)C XREJQMXBLFZXAH-UHFFFAOYSA-L 0.000 description 1
- JMUAMPJBYFHOQR-UHFFFAOYSA-N CCCCC(C1)=CC([Si](C)(C)C)=C1[Ti](C(CC(CCCC)=C1)=C1[Si](C)(C)C)=[Si](C)C Chemical compound CCCCC(C1)=CC([Si](C)(C)C)=C1[Ti](C(CC(CCCC)=C1)=C1[Si](C)(C)C)=[Si](C)C JMUAMPJBYFHOQR-UHFFFAOYSA-N 0.000 description 1
- TUVMCGVJFSCNRI-UHFFFAOYSA-L CCCCC1=Cc2c(cccc2-c2cccc3ccccc23)C1[Zr](Cl)(Cl)(C1C(CCCC)=Cc2c1cccc2-c1cccc2ccccc12)=[Si](C)C Chemical compound CCCCC1=Cc2c(cccc2-c2cccc3ccccc23)C1[Zr](Cl)(Cl)(C1C(CCCC)=Cc2c1cccc2-c1cccc2ccccc12)=[Si](C)C TUVMCGVJFSCNRI-UHFFFAOYSA-L 0.000 description 1
- ZMKUQEQXODAFMP-UHFFFAOYSA-L CCCCC1=Cc2c(cccc2-c2ccccc2)C1[Zr](Cl)(Cl)(C1C(CCCC)=Cc2c1cccc2-c1ccccc1)=[Si](C)C Chemical compound CCCCC1=Cc2c(cccc2-c2ccccc2)C1[Zr](Cl)(Cl)(C1C(CCCC)=Cc2c1cccc2-c1ccccc1)=[Si](C)C ZMKUQEQXODAFMP-UHFFFAOYSA-L 0.000 description 1
- XQXGMSVBDNYBNC-UHFFFAOYSA-L C[SiH2]C.[Cl-].[Cl-].[Hf+2] Chemical compound C[SiH2]C.[Cl-].[Cl-].[Hf+2] XQXGMSVBDNYBNC-UHFFFAOYSA-L 0.000 description 1
- OBNYDWRGRASNAR-UHFFFAOYSA-N C[Si](=[Hf](C1=C(C=C(C1)CCCC)CC)C1=C(C=C(C1)CCCC)CC)C Chemical compound C[Si](=[Hf](C1=C(C=C(C1)CCCC)CC)C1=C(C=C(C1)CCCC)CC)C OBNYDWRGRASNAR-UHFFFAOYSA-N 0.000 description 1
- RJCVOXAYDJTTAO-UHFFFAOYSA-N C[Si](C)(C)C1=CC2=CC=CC=C2C1[Ti](C1C2=CC=CC=C2C=C1[Si](C)(C)C)=[Si](C)C Chemical compound C[Si](C)(C)C1=CC2=CC=CC=C2C1[Ti](C1C2=CC=CC=C2C=C1[Si](C)(C)C)=[Si](C)C RJCVOXAYDJTTAO-UHFFFAOYSA-N 0.000 description 1
- VRNCZUFXWOCOLI-UHFFFAOYSA-L C[Si](C)=[Zr](Cl)(Cl)(C1C=CC(=C1)C(C)(C)C)C1C=CC(=C1)C(C)(C)C Chemical compound C[Si](C)=[Zr](Cl)(Cl)(C1C=CC(=C1)C(C)(C)C)C1C=CC(=C1)C(C)(C)C VRNCZUFXWOCOLI-UHFFFAOYSA-L 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- AEGXYRBSTNPBDQ-UHFFFAOYSA-L [Cl-].[Cl-].C(C)C=1C(C2=CC=CC=C2C=1)[Hf+2] Chemical compound [Cl-].[Cl-].C(C)C=1C(C2=CC=CC=C2C=1)[Hf+2] AEGXYRBSTNPBDQ-UHFFFAOYSA-L 0.000 description 1
- GVRCSIOFVLODJI-UHFFFAOYSA-L [Cl-].[Cl-].C(CC)C=1C(C2=CC=CC(=C2C1)C1=CC=CC2=CC=CC=C12)[Hf+2] Chemical compound [Cl-].[Cl-].C(CC)C=1C(C2=CC=CC(=C2C1)C1=CC=CC2=CC=CC=C12)[Hf+2] GVRCSIOFVLODJI-UHFFFAOYSA-L 0.000 description 1
- FIKDKWMGFNSEMI-UHFFFAOYSA-L [Cl-].[Cl-].C1=CC=C2C(C3=CC=CC4=C3C=C(C4[Zr+2])C)=CC=CC2=C1 Chemical compound [Cl-].[Cl-].C1=CC=C2C(C3=CC=CC4=C3C=C(C4[Zr+2])C)=CC=CC2=C1 FIKDKWMGFNSEMI-UHFFFAOYSA-L 0.000 description 1
- PEMDSHJRXWMAAZ-UHFFFAOYSA-L [Cl-].[Cl-].CC1=C(CC(=C1)C(C)(C)C)[Hf++](C1=C(C)C=C(C1)C(C)(C)C)=[Si](C)C Chemical compound [Cl-].[Cl-].CC1=C(CC(=C1)C(C)(C)C)[Hf++](C1=C(C)C=C(C1)C(C)(C)C)=[Si](C)C PEMDSHJRXWMAAZ-UHFFFAOYSA-L 0.000 description 1
- WICWXWFSVMJZCG-UHFFFAOYSA-L [Cl-].[Cl-].CC1=CC(C)=C(C1)[Zr++](C1=C(C)C=C(C)C1)=[Si](C)C Chemical compound [Cl-].[Cl-].CC1=CC(C)=C(C1)[Zr++](C1=C(C)C=C(C)C1)=[Si](C)C WICWXWFSVMJZCG-UHFFFAOYSA-L 0.000 description 1
- FBMFBKQUAXYMRV-UHFFFAOYSA-L [Cl-].[Cl-].CC1=Cc2c([C@H]1[Ti++]([C@@H]1C(C)=Cc3c1c(C)ccc3C)=[Si](C)C)c(C)ccc2C Chemical compound [Cl-].[Cl-].CC1=Cc2c([C@H]1[Ti++]([C@@H]1C(C)=Cc3c1c(C)ccc3C)=[Si](C)C)c(C)ccc2C FBMFBKQUAXYMRV-UHFFFAOYSA-L 0.000 description 1
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- NESCASMLZKFKTP-UHFFFAOYSA-L [Cl-].[Cl-].C[Si](=[Zr+2](C1=C(C=C(C1)[Si](C)(C)C)CCC)C1=C(C=C(C1)[Si](C)(C)C)CCC)C Chemical compound [Cl-].[Cl-].C[Si](=[Zr+2](C1=C(C=C(C1)[Si](C)(C)C)CCC)C1=C(C=C(C1)[Si](C)(C)C)CCC)C NESCASMLZKFKTP-UHFFFAOYSA-L 0.000 description 1
- UABKNTVLFBJNBM-UHFFFAOYSA-L [Cl-].[Cl-].C[Si](=[Zr+2](C1=C(C=C(C1)[Si](C)(C)C)CCCC)C1=C(C=C(C1)[Si](C)(C)C)CCCC)C Chemical compound [Cl-].[Cl-].C[Si](=[Zr+2](C1=C(C=C(C1)[Si](C)(C)C)CCCC)C1=C(C=C(C1)[Si](C)(C)C)CCCC)C UABKNTVLFBJNBM-UHFFFAOYSA-L 0.000 description 1
- OBXOZIBLMRGTSX-UHFFFAOYSA-L [Cl-].[Cl-].C[Si](=[Zr+2](C1C(=CC2=C(C=CC(=C12)C)C)C1=CC=CC=C1)C1C(=CC2=C(C=CC(=C12)C)C)C1=CC=CC=C1)C Chemical compound [Cl-].[Cl-].C[Si](=[Zr+2](C1C(=CC2=C(C=CC(=C12)C)C)C1=CC=CC=C1)C1C(=CC2=C(C=CC(=C12)C)C)C1=CC=CC=C1)C OBXOZIBLMRGTSX-UHFFFAOYSA-L 0.000 description 1
- BFALQZOZNHGNBJ-UHFFFAOYSA-L [Cl-].[Cl-].C[Si](=[Zr+2](C1C(=CC2=C(C=CC(=C12)C)C)CCCC)C1C(=CC2=C(C=CC(=C12)C)C)CCCC)C Chemical compound [Cl-].[Cl-].C[Si](=[Zr+2](C1C(=CC2=C(C=CC(=C12)C)C)CCCC)C1C(=CC2=C(C=CC(=C12)C)C)CCCC)C BFALQZOZNHGNBJ-UHFFFAOYSA-L 0.000 description 1
- GGRRDEJLRQLRKB-UHFFFAOYSA-L [Cl-].[Cl-].C[Si](=[Zr+2](C1C(=CC2=C(C=CC=C12)C1=CC=CC2=CC=CC=C12)[Si](C)(C)C)C1C(=CC2=C(C=CC=C12)C1=CC=CC2=CC=CC=C12)[Si](C)(C)C)C Chemical compound [Cl-].[Cl-].C[Si](=[Zr+2](C1C(=CC2=C(C=CC=C12)C1=CC=CC2=CC=CC=C12)[Si](C)(C)C)C1C(=CC2=C(C=CC=C12)C1=CC=CC2=CC=CC=C12)[Si](C)(C)C)C GGRRDEJLRQLRKB-UHFFFAOYSA-L 0.000 description 1
- RXFLIKBYTGKJCV-UHFFFAOYSA-L [Cl-].[Cl-].C[Si](=[Zr+2](C1C(=CC2=CC=C3C(=C12)C=CC=C3)[Si](C)(C)C)C1C(=CC2=CC=C3C(=C12)C=CC=C3)[Si](C)(C)C)C Chemical compound [Cl-].[Cl-].C[Si](=[Zr+2](C1C(=CC2=CC=C3C(=C12)C=CC=C3)[Si](C)(C)C)C1C(=CC2=CC=C3C(=C12)C=CC=C3)[Si](C)(C)C)C RXFLIKBYTGKJCV-UHFFFAOYSA-L 0.000 description 1
- OZCLPYKUWCIKIV-UHFFFAOYSA-L [Cl-].[Cl-].C[Si](=[Zr+2](C1C(=CC=2CCCCC1=2)C1=CC=CC=C1)C1C(=CC=2CCCCC1=2)C1=CC=CC=C1)C Chemical compound [Cl-].[Cl-].C[Si](=[Zr+2](C1C(=CC=2CCCCC1=2)C1=CC=CC=C1)C1C(=CC=2CCCCC1=2)C1=CC=CC=C1)C OZCLPYKUWCIKIV-UHFFFAOYSA-L 0.000 description 1
- BUNCGDOIYBEDFX-UHFFFAOYSA-L [Cl-].[Cl-].C[Si](C)=[Ti++](C1C(=Cc2ccccc12)c1ccccc1)C1C(=Cc2ccccc12)c1ccccc1 Chemical compound [Cl-].[Cl-].C[Si](C)=[Ti++](C1C(=Cc2ccccc12)c1ccccc1)C1C(=Cc2ccccc12)c1ccccc1 BUNCGDOIYBEDFX-UHFFFAOYSA-L 0.000 description 1
- XEBZBNXQGYCMEK-UHFFFAOYSA-L [Cl-].[Cl-].C[Si](C)=[Zr++](C1=C(C=C(C1)C(C)(C)C)C(C)(C)C)C1=C(C=C(C1)C(C)(C)C)C(C)(C)C Chemical compound [Cl-].[Cl-].C[Si](C)=[Zr++](C1=C(C=C(C1)C(C)(C)C)C(C)(C)C)C1=C(C=C(C1)C(C)(C)C)C(C)(C)C XEBZBNXQGYCMEK-UHFFFAOYSA-L 0.000 description 1
- GPTVXHHNFZPTOX-UHFFFAOYSA-L [Cl-].[Cl-].C[Si](C)=[Zr++]([C@H]1C(=Cc2ccccc12)C(C)(C)C)[C@@H]1C(=Cc2ccccc12)C(C)(C)C Chemical compound [Cl-].[Cl-].C[Si](C)=[Zr++]([C@H]1C(=Cc2ccccc12)C(C)(C)C)[C@@H]1C(=Cc2ccccc12)C(C)(C)C GPTVXHHNFZPTOX-UHFFFAOYSA-L 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- ANJHTOUUADABQR-UHFFFAOYSA-N bis(3-tert-butylcyclopenta-2,4-dien-1-yl)-dimethylsilane Chemical compound C1=CC(C(C)(C)C)=CC1[Si](C)(C)C1C=C(C(C)(C)C)C=C1 ANJHTOUUADABQR-UHFFFAOYSA-N 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000001316 cycloalkyl alkyl group Chemical group 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
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 230000005068 transpiration Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F17/00—Metallocenes
-
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/22—Tin compounds
- C07F7/2208—Compounds having tin linked only to carbon, hydrogen and/or halogen
-
- 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
-
- 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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19730880A DE19730880A1 (de) | 1997-07-18 | 1997-07-18 | Verfahren zur selektiven Herstellung von racemischen ansa-Metallocenkomplexen |
| DE19730880.5 | 1997-07-18 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH11106392A true JPH11106392A (ja) | 1999-04-20 |
| JPH11106392A5 JPH11106392A5 (enExample) | 2005-10-06 |
Family
ID=7836134
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10204061A Withdrawn JPH11106392A (ja) | 1997-07-18 | 1998-07-17 | ラセミ性アンサ−メタロセン錯体の製造方法 |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US5892081A (enExample) |
| EP (1) | EP0891980B1 (enExample) |
| JP (1) | JPH11106392A (enExample) |
| DE (2) | DE19730880A1 (enExample) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003018647A1 (en) * | 2001-08-24 | 2003-03-06 | Mitsubishi Chemical Corporation | Propylene polymer |
| US7659356B2 (en) | 2002-04-26 | 2010-02-09 | Mitsubishi Chemical Corporation | Polypropylene type aqueous dispersion, polypropylene type composite aqueous emulsion composition and its use |
| WO2015102251A1 (ko) * | 2013-12-31 | 2015-07-09 | 아주대학교산학협력단 | 안사-메탈로센 촉매를 이용한 알파-올레핀 올리고머의 제조방법 |
| JP2020530199A (ja) * | 2017-08-02 | 2020-10-15 | シースター ケミカルズ アンリミティッド ライアビリティ カンパニー | 高純度酸化スズの堆積のための有機金属化合物及び方法 |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5998643A (en) * | 1999-01-15 | 1999-12-07 | University Of Iowa Research Foundation | Metallocene synthesis |
| DE10017430A1 (de) | 2000-04-07 | 2001-10-11 | Basf Ag | Polymerisationskatalysator |
| EP1308470B8 (en) | 2001-11-01 | 2006-08-02 | Mitsubishi Chemical Corporation | Modified propylene polymer, adhesive composition obtainable therefrom and adhesive comprising the same |
| KR20060028603A (ko) * | 2004-09-25 | 2006-03-30 | 주식회사 엘지화학 | 안사-메탈로센 화합물, 그 제조방법 및 이를 이용한폴리올레핀의 제조방법 |
| EP3245258B1 (en) | 2015-01-06 | 2019-09-11 | Scg Chemicals Co. Ltd. | Sio2-layered double hydroxide microspheres and methods of making them |
| GB201608384D0 (en) | 2016-05-12 | 2016-06-29 | Scg Chemicals Co Ltd | Unsymmetrical metallocene catalysts and uses thereof |
| WO2019108408A1 (en) * | 2017-11-29 | 2019-06-06 | Exxonmobil Chemical Patents Inc. | Catalysts that produce polyethylene with broad, bimodal molecular weight distribution |
| US10882925B2 (en) | 2017-11-29 | 2021-01-05 | Exxonmobil Chemical Patents Inc. | Catalysts that produce polyethylene with broad, bimodal molecular weight distribution |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1992009545A2 (en) * | 1990-11-21 | 1992-06-11 | Massachusetts Institute Of Technology | New methods for the catalytic reduction of organic substrates |
| EP0654746B1 (en) * | 1993-11-24 | 2003-02-12 | Canon Kabushiki Kaisha | Form identification and processing system |
| DE4406110A1 (de) * | 1994-02-25 | 1995-08-31 | Witco Gmbh | Verbrückte Cyclopentadienylmagnesium-Verbindungen und Verfahren zu ihrer Herstellung und ihre Verwendung zur Herstellung von Metallocenen |
| DE4406109A1 (de) * | 1994-02-25 | 1995-08-31 | Witco Gmbh | Verfahren zur Herstellung von verbrückten stereorigiden Metallocenen |
| US5597935A (en) * | 1994-06-01 | 1997-01-28 | University Of Iowa Research Foundation | Synthesis of ansa-metallocene catalysts |
| US5495035A (en) * | 1994-06-01 | 1996-02-27 | University Of Iowa Research Foundation | Synthesis of ANSA-metallocene catalysts |
| DE19516803A1 (de) * | 1995-05-08 | 1996-11-14 | Hoechst Ag | Organometallverbindung |
-
1997
- 1997-07-18 DE DE19730880A patent/DE19730880A1/de not_active Withdrawn
-
1998
- 1998-06-16 DE DE59805764T patent/DE59805764D1/de not_active Expired - Fee Related
- 1998-06-16 EP EP98111004A patent/EP0891980B1/de not_active Expired - Lifetime
- 1998-07-13 US US09/114,190 patent/US5892081A/en not_active Expired - Fee Related
- 1998-07-17 JP JP10204061A patent/JPH11106392A/ja not_active Withdrawn
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003018647A1 (en) * | 2001-08-24 | 2003-03-06 | Mitsubishi Chemical Corporation | Propylene polymer |
| US7115694B2 (en) | 2001-08-24 | 2006-10-03 | Mitsubishi Chemical Corporation | Propylene-based polymer |
| US7659356B2 (en) | 2002-04-26 | 2010-02-09 | Mitsubishi Chemical Corporation | Polypropylene type aqueous dispersion, polypropylene type composite aqueous emulsion composition and its use |
| WO2015102251A1 (ko) * | 2013-12-31 | 2015-07-09 | 아주대학교산학협력단 | 안사-메탈로센 촉매를 이용한 알파-올레핀 올리고머의 제조방법 |
| JP2020530199A (ja) * | 2017-08-02 | 2020-10-15 | シースター ケミカルズ アンリミティッド ライアビリティ カンパニー | 高純度酸化スズの堆積のための有機金属化合物及び方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| DE19730880A1 (de) | 1999-01-21 |
| DE59805764D1 (de) | 2002-11-07 |
| EP0891980A1 (de) | 1999-01-20 |
| EP0891980B1 (de) | 2002-10-02 |
| US5892081A (en) | 1999-04-06 |
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