DE19730880A1 - Verfahren zur selektiven Herstellung von racemischen ansa-Metallocenkomplexen - Google Patents
Verfahren zur selektiven Herstellung von racemischen ansa-MetallocenkomplexenInfo
- Publication number
- DE19730880A1 DE19730880A1 DE19730880A DE19730880A DE19730880A1 DE 19730880 A1 DE19730880 A1 DE 19730880A1 DE 19730880 A DE19730880 A DE 19730880A DE 19730880 A DE19730880 A DE 19730880A DE 19730880 A1 DE19730880 A1 DE 19730880A1
- Authority
- DE
- Germany
- Prior art keywords
- group
- dichloride dimethylsilanediylbis
- alkyl
- aryl
- propyl
- 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- Withdrawn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
- 238000000034 method Methods 0.000 title claims description 17
- 238000004519 manufacturing process Methods 0.000 title description 4
- -1 iodine, hydrogen Chemical class 0.000 claims description 210
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 47
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 27
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 22
- 150000003606 tin compounds Chemical class 0.000 claims description 22
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 20
- 125000001424 substituent group Chemical group 0.000 claims description 17
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims description 17
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 16
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 16
- 125000004407 fluoroaryl group Chemical group 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 229910052710 silicon Inorganic materials 0.000 claims description 12
- 239000010703 silicon Substances 0.000 claims description 12
- 125000000027 (C1-C10) alkoxy 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
- 125000004429 atom Chemical group 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 11
- 125000005018 aryl alkenyl group Chemical group 0.000 claims description 10
- 125000004122 cyclic group Chemical group 0.000 claims description 9
- 150000003254 radicals Chemical group 0.000 claims description 9
- 229910052732 germanium Inorganic materials 0.000 claims description 8
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims description 8
- 229910052726 zirconium Inorganic materials 0.000 claims description 7
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 229910052719 titanium Inorganic materials 0.000 claims description 6
- 239000010936 titanium Substances 0.000 claims description 6
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 229910052735 hafnium Inorganic materials 0.000 claims description 5
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052758 niobium Inorganic materials 0.000 claims description 4
- 239000010955 niobium Substances 0.000 claims description 4
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 claims description 4
- 229910052715 tantalum Inorganic materials 0.000 claims description 4
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 claims description 4
- 229910052720 vanadium Inorganic materials 0.000 claims description 4
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 150000005840 aryl radicals Chemical class 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances 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
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical class C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- 239000011630 iodine Substances 0.000 claims 1
- 150000003623 transition metal compounds Chemical class 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 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
- 239000002904 solvent Substances 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- KUNZSLJMPCDOGI-UHFFFAOYSA-L [Cl-].[Cl-].[Hf+2] Chemical compound [Cl-].[Cl-].[Hf+2] KUNZSLJMPCDOGI-UHFFFAOYSA-L 0.000 description 4
- XOJVVFBFDXDTEG-UHFFFAOYSA-N pristane Chemical compound CC(C)CCCC(C)CCCC(C)CCCC(C)C XOJVVFBFDXDTEG-UHFFFAOYSA-N 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- ZWYDDDAMNQQZHD-UHFFFAOYSA-L titanium(ii) chloride Chemical compound [Cl-].[Cl-].[Ti+2] ZWYDDDAMNQQZHD-UHFFFAOYSA-L 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 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
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 229910052723 transition metal Inorganic materials 0.000 description 3
- 150000003624 transition metals Chemical class 0.000 description 3
- 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
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- NRTOMJZYCJJWKI-UHFFFAOYSA-N Titanium nitride Chemical compound [Ti]#N NRTOMJZYCJJWKI-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 229910001507 metal halide Inorganic materials 0.000 description 2
- 150000005309 metal halides Chemical class 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 239000000203 mixture Substances 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
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- VPGLGRNSAYHXPY-UHFFFAOYSA-L zirconium(2+);dichloride Chemical compound Cl[Zr]Cl VPGLGRNSAYHXPY-UHFFFAOYSA-L 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- MDRAMZUCZBWYQA-UHFFFAOYSA-L C1=CC=C2C(C3=CC=CC4=C3C=C(C)C4[Hf](Cl)(Cl)(C3C4=C(C(=CC=C4)C=4C5=CC=CC=C5C=CC=4)C=C3C)=[Si](C)C)=CC=CC2=C1 Chemical compound C1=CC=C2C(C3=CC=CC4=C3C=C(C)C4[Hf](Cl)(Cl)(C3C4=C(C(=CC=C4)C=4C5=CC=CC=C5C=CC=4)C=C3C)=[Si](C)C)=CC=CC2=C1 MDRAMZUCZBWYQA-UHFFFAOYSA-L 0.000 description 1
- TWZISZDLYYEEEM-UHFFFAOYSA-M CC(C)(C)C(C=C1)=CC1[Zr+](C1C=C(C(C)(C)C)C=C1)=[Si](C)C.[Cl-] Chemical compound CC(C)(C)C(C=C1)=CC1[Zr+](C1C=C(C(C)(C)C)C=C1)=[Si](C)C.[Cl-] TWZISZDLYYEEEM-UHFFFAOYSA-M 0.000 description 1
- HEFYRZBXYDZGAF-UHFFFAOYSA-N CCC(C(C1=CC=C2)[Zr](C3C4=CC=CC(C5=CC=CC6=CC=CC=C56)=C4C=C3CC)=[Si](C)C)=CC1=C2C1=CC=CC2=CC=CC=C12.CC(C(C1=CC=C2)[Zr](C3C4=CC=CC(C5=CC=CC6=CC=CC=C56)=C4C=C3C)=[Si](C)C)=CC1=C2C1=CC=CC2=CC=CC=C12.Cl.Cl.Cl.Cl Chemical compound CCC(C(C1=CC=C2)[Zr](C3C4=CC=CC(C5=CC=CC6=CC=CC=C56)=C4C=C3CC)=[Si](C)C)=CC1=C2C1=CC=CC2=CC=CC=C12.CC(C(C1=CC=C2)[Zr](C3C4=CC=CC(C5=CC=CC6=CC=CC=C56)=C4C=C3C)=[Si](C)C)=CC1=C2C1=CC=CC2=CC=CC=C12.Cl.Cl.Cl.Cl HEFYRZBXYDZGAF-UHFFFAOYSA-N 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- NHLSGAQKECXNIK-UHFFFAOYSA-L [Cl-].[Cl-].CCCCC1=Cc2ccccc2C1[Zr++](C1C(CCCC)=Cc2ccccc12)=[Si](C)C Chemical compound [Cl-].[Cl-].CCCCC1=Cc2ccccc2C1[Zr++](C1C(CCCC)=Cc2ccccc12)=[Si](C)C NHLSGAQKECXNIK-UHFFFAOYSA-L 0.000 description 1
- WJLNXXVAFKYJMI-UHFFFAOYSA-L [Cl-].[Cl-].C[Si](=[Hf+2](C1=C(C=C(C1)CC)C(C)(C)C)C1=C(C=C(C1)CC)C(C)(C)C)C Chemical compound [Cl-].[Cl-].C[Si](=[Hf+2](C1=C(C=C(C1)CC)C(C)(C)C)C1=C(C=C(C1)CC)C(C)(C)C)C WJLNXXVAFKYJMI-UHFFFAOYSA-L 0.000 description 1
- FGKJFKFENDWLLT-UHFFFAOYSA-L [Cl-].[Cl-].C[Si](=[Hf+2](C1=C(C=C(C1)CCC)CCC)C1=C(C=C(C1)CCC)CCC)C Chemical compound [Cl-].[Cl-].C[Si](=[Hf+2](C1=C(C=C(C1)CCC)CCC)C1=C(C=C(C1)CCC)CCC)C FGKJFKFENDWLLT-UHFFFAOYSA-L 0.000 description 1
- CTWSZRXNURABTG-UHFFFAOYSA-L [Cl-].[Cl-].C[Si](=[Hf+2](C1=C(C=C(C1)CCCC)CCCC)C1=C(C=C(C1)CCCC)CCCC)C Chemical compound [Cl-].[Cl-].C[Si](=[Hf+2](C1=C(C=C(C1)CCCC)CCCC)C1=C(C=C(C1)CCCC)CCCC)C CTWSZRXNURABTG-UHFFFAOYSA-L 0.000 description 1
- 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 1
- IMQBUGBMDLDQTI-UHFFFAOYSA-L [Cl-].[Cl-].C[Si](=[Hf+2](C1C(=CC2=C(C=CC(=C12)C)C)CCC)C1C(=CC2=C(C=CC(=C12)C)C)CCC)C Chemical compound [Cl-].[Cl-].C[Si](=[Hf+2](C1C(=CC2=C(C=CC(=C12)C)C)CCC)C1C(=CC2=C(C=CC(=C12)C)C)CCC)C IMQBUGBMDLDQTI-UHFFFAOYSA-L 0.000 description 1
- ZEQSEVLGZSKXPD-UHFFFAOYSA-L [Cl-].[Cl-].C[Si](=[Hf+2](C1C(=CC2=C(C=CC=C12)C1=CC=CC2=CC=CC=C12)CCC)C1C(=CC2=C(C=CC=C12)C1=CC=CC2=CC=CC=C12)CCC)C Chemical compound [Cl-].[Cl-].C[Si](=[Hf+2](C1C(=CC2=C(C=CC=C12)C1=CC=CC2=CC=CC=C12)CCC)C1C(=CC2=C(C=CC=C12)C1=CC=CC2=CC=CC=C12)CCC)C ZEQSEVLGZSKXPD-UHFFFAOYSA-L 0.000 description 1
- OKDUZGXBDZNBOV-UHFFFAOYSA-L [Cl-].[Cl-].C[Si](=[Hf+2](C1C(=CC2=CC=CC=C12)CCCC)C1C(=CC2=CC=CC=C12)CCCC)C Chemical compound [Cl-].[Cl-].C[Si](=[Hf+2](C1C(=CC2=CC=CC=C12)CCCC)C1C(=CC2=CC=CC=C12)CCCC)C OKDUZGXBDZNBOV-UHFFFAOYSA-L 0.000 description 1
- CMVNKERSNRLJFG-UHFFFAOYSA-L [Cl-].[Cl-].C[Si](=[Hf+2](C1C(=CC=2CCCCC1=2)CCCC)C1C(=CC=2CCCCC1=2)CCCC)C Chemical compound [Cl-].[Cl-].C[Si](=[Hf+2](C1C(=CC=2CCCCC1=2)CCCC)C1C(=CC=2CCCCC1=2)CCCC)C CMVNKERSNRLJFG-UHFFFAOYSA-L 0.000 description 1
- GZOKXFUACGQXAI-UHFFFAOYSA-L [Cl-].[Cl-].C[Si](=[Ti+2](C1=C(C=C(C1)CCCC)C)C1=C(C=C(C1)CCCC)C)C Chemical compound [Cl-].[Cl-].C[Si](=[Ti+2](C1=C(C=C(C1)CCCC)C)C1=C(C=C(C1)CCCC)C)C GZOKXFUACGQXAI-UHFFFAOYSA-L 0.000 description 1
- HFQPEZLRDORENU-UHFFFAOYSA-L [Cl-].[Cl-].C[Si](=[Ti+2](C1C(=CC2=C(C=C(C=C12)CCC)CCC)CCCC)C1C(=CC2=C(C=C(C=C12)CCC)CCC)CCCC)C Chemical compound [Cl-].[Cl-].C[Si](=[Ti+2](C1C(=CC2=C(C=C(C=C12)CCC)CCC)CCCC)C1C(=CC2=C(C=C(C=C12)CCC)CCC)CCCC)C HFQPEZLRDORENU-UHFFFAOYSA-L 0.000 description 1
- NOWDUSATPNJYQP-UHFFFAOYSA-L [Cl-].[Cl-].C[Si](=[Ti+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](=[Ti+2](C1C(=CC2=C(C=CC(=C12)C)C)CCCC)C1C(=CC2=C(C=CC(=C12)C)C)CCCC)C NOWDUSATPNJYQP-UHFFFAOYSA-L 0.000 description 1
- UFUCQWZVISWNRO-UHFFFAOYSA-L [Cl-].[Cl-].C[Si](=[Zr+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](=[Zr+2](C1C(=CC2=C(C=C(C=C12)CCC)CCC)CCC)C1C(=CC2=C(C=C(C=C12)CCC)CCC)CCC)C UFUCQWZVISWNRO-UHFFFAOYSA-L 0.000 description 1
- WHKKLLZNZIKCJM-UHFFFAOYSA-L [Cl-].[Cl-].C[Si](=[Zr+2](C1C(=CC=2CCCCC1=2)C(C)(C)C)C1C(=CC=2CCCCC1=2)C(C)(C)C)C Chemical compound [Cl-].[Cl-].C[Si](=[Zr+2](C1C(=CC=2CCCCC1=2)C(C)(C)C)C1C(=CC=2CCCCC1=2)C(C)(C)C)C WHKKLLZNZIKCJM-UHFFFAOYSA-L 0.000 description 1
- JRALZRCFYJOYDI-UHFFFAOYSA-L [Cl-].[Cl-].C[Si](C)=[Zr++]([C@H]1C(=Cc2ccccc12)c1ccccc1)[C@@H]1C(=Cc2ccccc12)c1ccccc1 Chemical compound [Cl-].[Cl-].C[Si](C)=[Zr++]([C@H]1C(=Cc2ccccc12)c1ccccc1)[C@@H]1C(=Cc2ccccc12)c1ccccc1 JRALZRCFYJOYDI-UHFFFAOYSA-L 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 229910052729 chemical element Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000013078 crystal Substances 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
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000002222 fluorine compounds Chemical group 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical class C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 239000003960 organic solvent Substances 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
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 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
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- 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)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19730880A DE19730880A1 (de) | 1997-07-18 | 1997-07-18 | Verfahren zur selektiven Herstellung von racemischen ansa-Metallocenkomplexen |
| EP98111004A EP0891980B1 (de) | 1997-07-18 | 1998-06-16 | Verfahren zur selektiven Herstellung von racemischen ansa-Metallocenkomplexen |
| DE59805764T DE59805764D1 (de) | 1997-07-18 | 1998-06-16 | Verfahren zur selektiven Herstellung von racemischen ansa-Metallocenkomplexen |
| US09/114,190 US5892081A (en) | 1997-07-18 | 1998-07-13 | Selective preparation of racemic ansa-metallocene complexes |
| JP10204061A 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 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19730880A DE19730880A1 (de) | 1997-07-18 | 1997-07-18 | Verfahren zur selektiven Herstellung von racemischen ansa-Metallocenkomplexen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE19730880A1 true DE19730880A1 (de) | 1999-01-21 |
Family
ID=7836134
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19730880A Withdrawn DE19730880A1 (de) | 1997-07-18 | 1997-07-18 | Verfahren zur selektiven Herstellung von racemischen ansa-Metallocenkomplexen |
| DE59805764T Expired - Fee Related DE59805764D1 (de) | 1997-07-18 | 1998-06-16 | Verfahren zur selektiven Herstellung von racemischen ansa-Metallocenkomplexen |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE59805764T Expired - Fee Related DE59805764D1 (de) | 1997-07-18 | 1998-06-16 | Verfahren zur selektiven Herstellung von racemischen ansa-Metallocenkomplexen |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US5892081A (enExample) |
| EP (1) | EP0891980B1 (enExample) |
| JP (1) | JPH11106392A (enExample) |
| DE (2) | DE19730880A1 (enExample) |
Families Citing this family (12)
| 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 |
| EP1424348B1 (en) * | 2001-08-24 | 2005-11-02 | Mitsubishi Chemical Corporation | Propylene polymer |
| EP1308470B8 (en) | 2001-11-01 | 2006-08-02 | Mitsubishi Chemical Corporation | Modified propylene polymer, adhesive composition obtainable therefrom and adhesive comprising the same |
| US20050124753A1 (en) * | 2002-04-26 | 2005-06-09 | Mitsubishi Chemical Corporation | Polypropylene type aqueous dispersion, polypropylene type composite aqueous emulsion composition and its use |
| KR20060028603A (ko) * | 2004-09-25 | 2006-03-30 | 주식회사 엘지화학 | 안사-메탈로센 화합물, 그 제조방법 및 이를 이용한폴리올레핀의 제조방법 |
| KR101429746B1 (ko) * | 2013-12-31 | 2014-09-17 | 아주대학교산학협력단 | 안사-메탈로센 촉매를 이용한 알파-올레핀 올리고머의 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 |
| CA2975104A1 (en) * | 2017-08-02 | 2019-02-02 | Seastar Chemicals Inc. | Organometallic compounds and methods for the deposition of high purity tin oxide |
| 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
Also Published As
| Publication number | Publication date |
|---|---|
| JPH11106392A (ja) | 1999-04-20 |
| DE59805764D1 (de) | 2002-11-07 |
| EP0891980A1 (de) | 1999-01-20 |
| EP0891980B1 (de) | 2002-10-02 |
| US5892081A (en) | 1999-04-06 |
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