JP4050803B2 - 生成物混合物中の副生物の濃度を低下させる方法 - Google Patents
生成物混合物中の副生物の濃度を低下させる方法 Download PDFInfo
- Publication number
- JP4050803B2 JP4050803B2 JP33664696A JP33664696A JP4050803B2 JP 4050803 B2 JP4050803 B2 JP 4050803B2 JP 33664696 A JP33664696 A JP 33664696A JP 33664696 A JP33664696 A JP 33664696A JP 4050803 B2 JP4050803 B2 JP 4050803B2
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- zirconium dichloride
- bis
- metallocene
- 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.)
- Expired - Lifetime
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- 239000006227 byproduct Substances 0.000 title claims abstract description 44
- 239000000203 mixture Substances 0.000 title claims abstract description 33
- 238000000034 method Methods 0.000 title claims abstract description 27
- 239000000047 product Substances 0.000 title claims abstract description 11
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 17
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 16
- 229910001507 metal halide Inorganic materials 0.000 claims abstract description 8
- 150000005309 metal halides Chemical class 0.000 claims abstract description 8
- 150000003839 salts Chemical class 0.000 claims abstract description 7
- 238000000605 extraction Methods 0.000 claims abstract 5
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 claims description 18
- 125000002524 organometallic group Chemical group 0.000 claims description 18
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 239000011737 fluorine Substances 0.000 claims description 10
- 229910052751 metal Inorganic materials 0.000 claims description 10
- 239000002184 metal Substances 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 9
- 239000012043 crude product Substances 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000004429 atom Chemical group 0.000 claims description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- 230000000737 periodic effect Effects 0.000 claims description 6
- XOJVVFBFDXDTEG-UHFFFAOYSA-N pristane Chemical compound CC(C)CCCC(C)CCCC(C)CCCC(C)C XOJVVFBFDXDTEG-UHFFFAOYSA-N 0.000 claims description 5
- 230000007704 transition Effects 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 3
- 150000001299 aldehydes Chemical class 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 2
- 150000002390 heteroarenes Chemical class 0.000 claims description 2
- 150000002825 nitriles Chemical class 0.000 claims description 2
- 150000002828 nitro derivatives Chemical class 0.000 claims description 2
- 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 11
- 239000003495 polar organic solvent Substances 0.000 claims 3
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims 2
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 2
- 125000003158 alcohol group Chemical group 0.000 claims 2
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims 1
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 239000002798 polar solvent Substances 0.000 abstract description 12
- 239000007795 chemical reaction product Substances 0.000 abstract description 2
- 239000003795 chemical substances by application Substances 0.000 abstract 3
- -1 TiClFour Chemical class 0.000 description 150
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 22
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 20
- VPGLGRNSAYHXPY-UHFFFAOYSA-L zirconium(2+);dichloride Chemical compound Cl[Zr]Cl VPGLGRNSAYHXPY-UHFFFAOYSA-L 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- ZWVMLYRJXORSEP-LURJTMIESA-N (2s)-hexane-1,2,6-triol Chemical compound OCCCC[C@H](O)CO ZWVMLYRJXORSEP-LURJTMIESA-N 0.000 description 14
- DZETZMSAJDMAKS-UHFFFAOYSA-L Cl[Zr]Cl.[CH]1C(C)=CC2=C1C=CC=C2C1=CC=CC=C1 Chemical compound Cl[Zr]Cl.[CH]1C(C)=CC2=C1C=CC=C2C1=CC=CC=C1 DZETZMSAJDMAKS-UHFFFAOYSA-L 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 12
- 239000003446 ligand Substances 0.000 description 11
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 10
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 10
- 229910052735 hafnium Inorganic materials 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- CGELJBSWQTYCIY-UHFFFAOYSA-L [Cl-].[Cl-].CC1=Cc2ccccc2[C@H]1[Zr++]([C@@H]1C(C)=Cc2ccccc12)=[Si](C)C Chemical compound [Cl-].[Cl-].CC1=Cc2ccccc2[C@H]1[Zr++]([C@@H]1C(C)=Cc2ccccc12)=[Si](C)C CGELJBSWQTYCIY-UHFFFAOYSA-L 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
- ZWYDDDAMNQQZHD-UHFFFAOYSA-L titanium(ii) chloride Chemical compound [Cl-].[Cl-].[Ti+2] ZWYDDDAMNQQZHD-UHFFFAOYSA-L 0.000 description 8
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 7
- PATLRDHGHBZQMP-UHFFFAOYSA-L Cl[Zr]Cl.[CH]1C(CC)=CC2=C1C=CC=C2C1=CC=CC=C1 Chemical compound Cl[Zr]Cl.[CH]1C(CC)=CC2=C1C=CC=C2C1=CC=CC=C1 PATLRDHGHBZQMP-UHFFFAOYSA-L 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 125000004122 cyclic group Chemical group 0.000 description 6
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 description 6
- 239000012454 non-polar solvent Substances 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 5
- KUNZSLJMPCDOGI-UHFFFAOYSA-L [Cl-].[Cl-].[Hf+2] Chemical compound [Cl-].[Cl-].[Hf+2] KUNZSLJMPCDOGI-UHFFFAOYSA-L 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- HJYFEVJAUMKYSP-UHFFFAOYSA-L Cl[Zr]Cl.CCC1=CC2=C(C=CC=C2[CH]1)C1=CC=CC2=CC=CC=C12 Chemical compound Cl[Zr]Cl.CCC1=CC2=C(C=CC=C2[CH]1)C1=CC=CC2=CC=CC=C12 HJYFEVJAUMKYSP-UHFFFAOYSA-L 0.000 description 4
- 150000001336 alkenes Chemical class 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 3
- QFLBIYKGDGZDLN-UHFFFAOYSA-L CC(C(C1=CC=C2)[Ti+2])=CC1=C2C1=CC=CC=C1.[I-].[I-] Chemical compound CC(C(C1=CC=C2)[Ti+2])=CC1=C2C1=CC=CC=C1.[I-].[I-] QFLBIYKGDGZDLN-UHFFFAOYSA-L 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 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 3
- VNVUTMPEJGCDNY-UHFFFAOYSA-L [Cl-].[Cl-].C1=CC=C2C([Zr+2])C(CC)=CC2=C1 Chemical compound [Cl-].[Cl-].C1=CC=C2C([Zr+2])C(CC)=CC2=C1 VNVUTMPEJGCDNY-UHFFFAOYSA-L 0.000 description 3
- YFBRHWRGXKWPLT-UHFFFAOYSA-L [Cl-].[Cl-].CC(C)C1=CC(C(C)C)=CC2=C1C=C(C)C2[Zr+2] Chemical compound [Cl-].[Cl-].CC(C)C1=CC(C(C)C)=CC2=C1C=C(C)C2[Zr+2] YFBRHWRGXKWPLT-UHFFFAOYSA-L 0.000 description 3
- DBOJPIUPTNORNW-UHFFFAOYSA-L [Cl-].[Cl-].CC1=Cc2c(cccc2-c2ccccc2)C1[Hf++] Chemical compound [Cl-].[Cl-].CC1=Cc2c(cccc2-c2ccccc2)C1[Hf++] DBOJPIUPTNORNW-UHFFFAOYSA-L 0.000 description 3
- BDTYIXUDCWAIOX-UHFFFAOYSA-L [Cl-].[Cl-].[Zr+2]C1C(CC)=CC2=C1C=C(C(C)C)C=C2C(C)C Chemical compound [Cl-].[Cl-].[Zr+2]C1C(CC)=CC2=C1C=C(C(C)C)C=C2C(C)C BDTYIXUDCWAIOX-UHFFFAOYSA-L 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000005119 centrifugation Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 239000012634 fragment Substances 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 3
- 229910052726 zirconium Inorganic materials 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- CETWDUZRCINIHU-UHFFFAOYSA-N 2-heptanol Chemical compound CCCCCC(C)O CETWDUZRCINIHU-UHFFFAOYSA-N 0.000 description 2
- WFRBDWRZVBPBDO-UHFFFAOYSA-N 2-methyl-2-pentanol Chemical compound CCCC(C)(C)O WFRBDWRZVBPBDO-UHFFFAOYSA-N 0.000 description 2
- GXDHCNNESPLIKD-UHFFFAOYSA-N 2-methylhexane Chemical compound CCCCC(C)C GXDHCNNESPLIKD-UHFFFAOYSA-N 0.000 description 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- KYWJZCSJMOILIZ-UHFFFAOYSA-N 3-methylhexan-3-ol Chemical compound CCCC(C)(O)CC KYWJZCSJMOILIZ-UHFFFAOYSA-N 0.000 description 2
- PFEOZHBOMNWTJB-UHFFFAOYSA-N 3-methylpentane Chemical compound CCC(C)CC PFEOZHBOMNWTJB-UHFFFAOYSA-N 0.000 description 2
- YVBCULSIZWMTFY-UHFFFAOYSA-N 4-Heptanol Natural products CCCC(O)CCC YVBCULSIZWMTFY-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- QDIYJWQMXCZFAU-UHFFFAOYSA-L CC(C(C1=CC=C2)[Ti+2])=CC1=C2C1=CC=CC=C1.[Br-].[Br-] Chemical compound CC(C(C1=CC=C2)[Ti+2])=CC1=C2C1=CC=CC=C1.[Br-].[Br-] QDIYJWQMXCZFAU-UHFFFAOYSA-L 0.000 description 2
- NHLCFEFEZKUUQU-UHFFFAOYSA-L CC1=CC(C2=CC=CC(CC3)=C2C3=C2)=C2C1=[Ti+2].[Br-].[Br-] Chemical compound CC1=CC(C2=CC=CC(CC3)=C2C3=C2)=C2C1=[Ti+2].[Br-].[Br-] NHLCFEFEZKUUQU-UHFFFAOYSA-L 0.000 description 2
- 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 2
- KUBPPJMBIIZDGI-UHFFFAOYSA-L CCC1=Cc2c(cccc2-c2cccc3ccccc23)C1[Zr](Cl)(Cl)(C1C(CC)=Cc2c1cccc2-c1cccc2ccccc12)=[Si](C)C Chemical compound CCC1=Cc2c(cccc2-c2cccc3ccccc23)C1[Zr](Cl)(Cl)(C1C(CC)=Cc2c1cccc2-c1cccc2ccccc12)=[Si](C)C KUBPPJMBIIZDGI-UHFFFAOYSA-L 0.000 description 2
- NCSCOKCQVBPFES-UHFFFAOYSA-L CCC1=Cc2c(cccc2-c2cccc3ccccc23)C1[Zr](Cl)(Cl)(C1C(CC)=Cc2c1cccc2-c1cccc2ccccc12)=[Si](c1ccccc1)c1ccccc1 Chemical compound CCC1=Cc2c(cccc2-c2cccc3ccccc23)C1[Zr](Cl)(Cl)(C1C(CC)=Cc2c1cccc2-c1cccc2ccccc12)=[Si](c1ccccc1)c1ccccc1 NCSCOKCQVBPFES-UHFFFAOYSA-L 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- XJONFIGVOQMBIP-UHFFFAOYSA-L Cl[Zr](Cl)C1C=CC=C1 Chemical compound Cl[Zr](Cl)C1C=CC=C1 XJONFIGVOQMBIP-UHFFFAOYSA-L 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- RZKSECIXORKHQS-UHFFFAOYSA-N Heptan-3-ol Chemical compound CCCCC(O)CC RZKSECIXORKHQS-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
- QCOGKXLOEWLIDC-UHFFFAOYSA-N N-methylbutylamine Chemical compound CCCCNC QCOGKXLOEWLIDC-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- VNDYJBBGRKZCSX-UHFFFAOYSA-L Zinc bromide Inorganic materials Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 description 2
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- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
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- SNQFNJBZYZBXGD-UHFFFAOYSA-L Cl[Hf](Cl)C1C=CC=C1 Chemical compound Cl[Hf](Cl)C1C=CC=C1 SNQFNJBZYZBXGD-UHFFFAOYSA-L 0.000 description 1
- LMLWIMMAGLPLSK-UHFFFAOYSA-L Cl[Sc](Cl)C1C=Cc2ccccc12 Chemical compound Cl[Sc](Cl)C1C=Cc2ccccc12 LMLWIMMAGLPLSK-UHFFFAOYSA-L 0.000 description 1
- KKDBZWZRJNRBGA-UHFFFAOYSA-L Cl[Ti]Cl.[CH]1C=CC=C1 Chemical compound Cl[Ti]Cl.[CH]1C=CC=C1 KKDBZWZRJNRBGA-UHFFFAOYSA-L 0.000 description 1
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- ZBKJVVTWGPHNSC-UHFFFAOYSA-L Cl[Zr]Cl.C[C]1C(C)=C(C)C(C)=C1C Chemical compound Cl[Zr]Cl.C[C]1C(C)=C(C)C(C)=C1C ZBKJVVTWGPHNSC-UHFFFAOYSA-L 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- XOBKSJJDNFUZPF-UHFFFAOYSA-N Methoxyethane Chemical compound CCOC XOBKSJJDNFUZPF-UHFFFAOYSA-N 0.000 description 1
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 1
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
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- CXOFVDLJLONNDW-UHFFFAOYSA-N Phenytoin Chemical group N1C(=O)NC(=O)C1(C=1C=CC=CC=1)C1=CC=CC=C1 CXOFVDLJLONNDW-UHFFFAOYSA-N 0.000 description 1
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 244000028419 Styrax benzoin Species 0.000 description 1
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- 235000008411 Sumatra benzointree Nutrition 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- BMBCNIFGJHXBLM-UHFFFAOYSA-L [Br-].[Br-].C(C)C=1C(C2=CC=CC(=C2C=1)C1=CC=CC=C1)[Hf+2] Chemical compound [Br-].[Br-].C(C)C=1C(C2=CC=CC(=C2C=1)C1=CC=CC=C1)[Hf+2] BMBCNIFGJHXBLM-UHFFFAOYSA-L 0.000 description 1
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- HUFAYLVHRCWRQC-UHFFFAOYSA-L [Br-].[Br-].CC1=Cc2ccccc2C1[Hf++] Chemical compound [Br-].[Br-].CC1=Cc2ccccc2C1[Hf++] HUFAYLVHRCWRQC-UHFFFAOYSA-L 0.000 description 1
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- DPVJWMUGNYJCET-UHFFFAOYSA-L [Cl-].[Cl-].CC=1C(C2=CC(=CC(=C2C=1)C(C)C)C(C)C)[Hf+2] Chemical compound [Cl-].[Cl-].CC=1C(C2=CC(=CC(=C2C=1)C(C)C)C(C)C)[Hf+2] DPVJWMUGNYJCET-UHFFFAOYSA-L 0.000 description 1
- XVAUINIBHUKALA-UHFFFAOYSA-L [I-].[I-].C(C)C=1C(C2=CC=CC=C2C=1)[Hf+2] Chemical compound [I-].[I-].C(C)C=1C(C2=CC=CC=C2C=1)[Hf+2] XVAUINIBHUKALA-UHFFFAOYSA-L 0.000 description 1
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- HPSYLUGNTBQYQV-UHFFFAOYSA-L [I-].[I-].CC=1C(C2=CC=CC=C2C=1)[Hf+2] Chemical compound [I-].[I-].CC=1C(C2=CC=CC=C2C=1)[Hf+2] HPSYLUGNTBQYQV-UHFFFAOYSA-L 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- XPNGNIFUDRPBFJ-UHFFFAOYSA-N alpha-methylbenzylalcohol Natural products CC1=CC=CC=C1CO XPNGNIFUDRPBFJ-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 229910001626 barium chloride Inorganic materials 0.000 description 1
- WDIHJSXYQDMJHN-UHFFFAOYSA-L barium chloride Chemical compound [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 description 1
- 229910001638 barium iodide Inorganic materials 0.000 description 1
- 229960002130 benzoin Drugs 0.000 description 1
- GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
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- 229940043232 butyl acetate Drugs 0.000 description 1
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Inorganic materials [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 1
- XQPRBTXUXXVTKB-UHFFFAOYSA-M caesium iodide Inorganic materials [I-].[Cs+] XQPRBTXUXXVTKB-UHFFFAOYSA-M 0.000 description 1
- 229910001622 calcium bromide Inorganic materials 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- WGEFECGEFUFIQW-UHFFFAOYSA-L calcium dibromide Chemical compound [Ca+2].[Br-].[Br-] WGEFECGEFUFIQW-UHFFFAOYSA-L 0.000 description 1
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 description 1
- 229910001634 calcium fluoride Inorganic materials 0.000 description 1
- 229910001640 calcium iodide Inorganic materials 0.000 description 1
- JARKCYVAAOWBJS-UHFFFAOYSA-N caproic aldehyde Natural products CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- MLVFYXKWIBURLH-UHFFFAOYSA-N chloromethane;dichloromethane Chemical compound ClC.ClCCl MLVFYXKWIBURLH-UHFFFAOYSA-N 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- DIOQZVSQGTUSAI-NJFSPNSNSA-N decane Chemical compound CCCCCCCCC[14CH3] DIOQZVSQGTUSAI-NJFSPNSNSA-N 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- 229940113088 dimethylacetamide Drugs 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229940093499 ethyl acetate Drugs 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- UHCBBWUQDAVSMS-UHFFFAOYSA-N fluoroethane Chemical compound CCF UHCBBWUQDAVSMS-UHFFFAOYSA-N 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- QEUHJZZUEFYTLK-UHFFFAOYSA-N hexanal Chemical compound [CH2]CCCCC=O QEUHJZZUEFYTLK-UHFFFAOYSA-N 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229910001867 inorganic solvent Inorganic materials 0.000 description 1
- 239000003049 inorganic solvent Substances 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- HSZCZNFXUDYRKD-UHFFFAOYSA-M lithium iodide Inorganic materials [Li+].[I-] HSZCZNFXUDYRKD-UHFFFAOYSA-M 0.000 description 1
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L magnesium chloride Substances [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 229910001635 magnesium fluoride Inorganic materials 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 239000012968 metallocene catalyst Substances 0.000 description 1
- ZKWONARDNQWFKT-UHFFFAOYSA-N methanolate;titanium(2+) Chemical compound CO[Ti]OC ZKWONARDNQWFKT-UHFFFAOYSA-N 0.000 description 1
- 229940017219 methyl propionate Drugs 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- JDEJGVSZUIJWBM-UHFFFAOYSA-N n,n,2-trimethylaniline Chemical compound CN(C)C1=CC=CC=C1C JDEJGVSZUIJWBM-UHFFFAOYSA-N 0.000 description 1
- AJFDBNQQDYLMJN-UHFFFAOYSA-N n,n-diethylacetamide Chemical compound CCN(CC)C(C)=O AJFDBNQQDYLMJN-UHFFFAOYSA-N 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- QQZOPKMRPOGIEB-UHFFFAOYSA-N n-butyl methyl ketone Natural products CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 1
- DIOQZVSQGTUSAI-UHFFFAOYSA-N n-butylhexane Natural products CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 1
- MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- ZCYXXKJEDCHMGH-UHFFFAOYSA-N nonane Chemical compound CCCC[CH]CCCC ZCYXXKJEDCHMGH-UHFFFAOYSA-N 0.000 description 1
- BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 1
- FWIYBTVHGYLSAZ-UHFFFAOYSA-I pentaiodoniobium Chemical compound I[Nb](I)(I)(I)I FWIYBTVHGYLSAZ-UHFFFAOYSA-I 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- AUZMWGNTACEWDV-UHFFFAOYSA-L titanium(2+);dibromide Chemical compound Br[Ti]Br AUZMWGNTACEWDV-UHFFFAOYSA-L 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F17/00—Metallocenes
-
- 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)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Disintegrating Or Milling (AREA)
- Extraction Or Liquid Replacement (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Superconductors And Manufacturing Methods Therefor (AREA)
- Detergent Compositions (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1995147247 DE19547247A1 (de) | 1995-12-18 | 1995-12-18 | Verfahren zur Abreicherung von organometallischen Nebenprodukten in Produktgemischen |
| DE19547247.0 | 1995-12-18 | ||
| DE19547248.9 | 1995-12-18 | ||
| DE1995147248 DE19547248A1 (de) | 1995-12-18 | 1995-12-18 | Verfahren zur Abreichung von anorganischen Nebenprodukten |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JPH09176178A JPH09176178A (ja) | 1997-07-08 |
| JPH09176178A5 JPH09176178A5 (enExample) | 2004-12-02 |
| JP4050803B2 true JP4050803B2 (ja) | 2008-02-20 |
Family
ID=26021377
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP33664696A Expired - Lifetime JP4050803B2 (ja) | 1995-12-18 | 1996-12-17 | 生成物混合物中の副生物の濃度を低下させる方法 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US5770752A (enExample) |
| EP (1) | EP0780396B1 (enExample) |
| JP (1) | JP4050803B2 (enExample) |
| KR (1) | KR970042576A (enExample) |
| CN (1) | CN1072674C (enExample) |
| AT (1) | ATE225359T1 (enExample) |
| BR (1) | BR9606033A (enExample) |
| DE (1) | DE59609748D1 (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1133503A1 (de) | 1998-11-25 | 2001-09-19 | Basell Polyolefine GmbH | Verfahren zur aufreinigung von metallocenen |
| US6620953B1 (en) | 1998-11-25 | 2003-09-16 | Bassell Polyolefine Gmbh | Method for producing monoaryloxy-ansa-metallocenes |
| US6818585B2 (en) | 1998-12-30 | 2004-11-16 | Univation Technologies, Llc | Catalyst compounds, catalyst systems thereof and their use in a polymerization process |
| US6515086B1 (en) | 1999-02-19 | 2003-02-04 | Fina Research, S.A. | Polyolefin production |
| AU3141199A (en) * | 1999-02-19 | 2000-09-04 | Fina Research S.A. | Polyolefin production |
| US6339134B1 (en) | 1999-05-06 | 2002-01-15 | Univation Technologies, Llc | Polymerization process for producing easier processing polymers |
| DE10017430A1 (de) | 2000-04-07 | 2001-10-11 | Basf Ag | Polymerisationskatalysator |
| DE10126265A1 (de) | 2001-05-29 | 2002-12-05 | Basell Polyolefine Gmbh | Verfahren zur Abreicherung von anorganischen Nebenprodukten und organometallischen Nebenprodukten bei der Herstellung von Metallocenen sowie der wirtschaftlichen Rückgewinnung der eingesetzten Edukte |
| KR20040072701A (ko) * | 2002-01-08 | 2004-08-18 | 미쓰비시 마테리알 가부시키가이샤 | 루테늄 화합물 및 그 제조 방법 그리고 그 화합물에 의해얻어진 루테늄 함유 박막 |
| US20050148460A1 (en) * | 2004-01-02 | 2005-07-07 | Vladimir Marin | Catalyst components and their use in the polymerization of olefins |
| US7285608B2 (en) | 2004-04-21 | 2007-10-23 | Novolen Technology Holdings C.V. | Metallocene ligands, metallocene compounds and metallocene catalysts, their synthesis and their use for the polymerization of olefins |
| US7550544B2 (en) * | 2005-12-14 | 2009-06-23 | Exxonmobil Chemical Patents Inc. | Halogen substituted metallocene compounds for olefin polymerization |
| DE102005061326A1 (de) * | 2005-12-20 | 2007-06-21 | Basell Polyolefine Gmbh | Verfahren zur Herstellung von Metallocenen aus recycelten, substituierten Cyclopentadienylderivaten |
| EP2573091A1 (en) | 2011-09-23 | 2013-03-27 | Lummus Novolen Technology Gmbh | Process for recycling of free ligand from their corresponding metallocene complexes |
| US8962893B2 (en) | 2012-08-28 | 2015-02-24 | Rohm And Haas Electronic Materials Llc | Organometallic compound purification |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5324800A (en) * | 1983-06-06 | 1994-06-28 | Exxon Chemical Patents Inc. | Process and catalyst for polyolefin density and molecular weight control |
| ZA844157B (en) | 1983-06-06 | 1986-01-29 | Exxon Research Engineering Co | Process and catalyst for polyolefin density and molecular weight control |
| US4752597A (en) | 1985-12-12 | 1988-06-21 | Exxon Chemical Patents Inc. | New polymerization catalyst |
| DE3742934A1 (de) | 1987-12-18 | 1989-06-29 | Hoechst Ag | Verfahren zur herstellung einer chiralen, stereorigiden metallocen-verbindung |
| DE3808268A1 (de) | 1988-03-12 | 1989-09-21 | Hoechst Ag | Verfahren zur herstellung eines 1-olefinpolymers |
| US5017714A (en) | 1988-03-21 | 1991-05-21 | Exxon Chemical Patents Inc. | Silicon-bridged transition metal compounds |
| DE3907965A1 (de) * | 1989-03-11 | 1990-09-13 | Hoechst Ag | Verfahren zur herstellung eines syndiotaktischen polyolefins |
| JP2837246B2 (ja) | 1990-07-20 | 1998-12-14 | 三井化学株式会社 | 新規なシンジオタクチックポリプロピレン |
| JP2837247B2 (ja) | 1990-07-30 | 1998-12-14 | 三井化学株式会社 | シンジオタクチックポリ―α―オレフィンの製造方法 |
| TW300901B (enExample) | 1991-08-26 | 1997-03-21 | Hoechst Ag | |
| DE59210001D1 (de) | 1991-10-15 | 2005-02-17 | Basell Polyolefine Gmbh | Verfahren zur Herstellung eines Olefinpolymers unter Verwendung von Metallocenen mit speziell substituierten Indenylliganden |
| ES2093166T3 (es) | 1991-11-30 | 1996-12-16 | Hoechst Ag | Metalocenos con derivados de indenilo condensados con benzo como ligandos, procedimiento para su preparacion y su utilizacion como catalizadores. |
| US5302733A (en) * | 1992-03-30 | 1994-04-12 | Ethyl Corporation | Preparation of metallocenes |
| ATE162529T1 (de) * | 1992-06-13 | 1998-02-15 | Hoechst Ag | Verfahren zur herstellung von verbrückten, chiralen metallocenkatalysatoren des types bisindenyl |
| TW294669B (enExample) * | 1992-06-27 | 1997-01-01 | Hoechst Ag | |
| US5372980A (en) | 1993-06-03 | 1994-12-13 | Polysar | Bimetallic metallocene alumoxane catalyst system and its use in the preparation of ethylene-alpha olefin and ethylene-alpha olefin-non-conjugated diolefin elastomers |
| JP3220577B2 (ja) * | 1993-09-29 | 2001-10-22 | 三井化学株式会社 | メタロセン化合物の精製方法 |
| EP0654476B1 (de) | 1993-11-24 | 2001-01-24 | TARGOR GmbH | Metallocene, Verfahren zu ihrer Herstellung und ihrer Verwendung als Katalysatoren |
| DE4406109A1 (de) * | 1994-02-25 | 1995-08-31 | Witco Gmbh | Verfahren zur Herstellung von verbrückten stereorigiden Metallocenen |
| US5556997A (en) * | 1995-04-24 | 1996-09-17 | Albemarle Corporation | Enhanced synthesis of racemic metallocenes |
-
1996
- 1996-12-16 AT AT96120155T patent/ATE225359T1/de not_active IP Right Cessation
- 1996-12-16 EP EP96120155A patent/EP0780396B1/de not_active Expired - Lifetime
- 1996-12-16 DE DE59609748T patent/DE59609748D1/de not_active Expired - Lifetime
- 1996-12-17 CN CN96121559A patent/CN1072674C/zh not_active Expired - Lifetime
- 1996-12-17 JP JP33664696A patent/JP4050803B2/ja not_active Expired - Lifetime
- 1996-12-17 BR BR9606033A patent/BR9606033A/pt not_active Application Discontinuation
- 1996-12-18 KR KR1019960067183A patent/KR970042576A/ko not_active Withdrawn
- 1996-12-18 US US08/768,638 patent/US5770752A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH09176178A (ja) | 1997-07-08 |
| KR970042576A (ko) | 1997-07-24 |
| EP0780396B1 (de) | 2002-10-02 |
| DE59609748D1 (de) | 2002-11-07 |
| US5770752A (en) | 1998-06-23 |
| CN1072674C (zh) | 2001-10-10 |
| CN1160055A (zh) | 1997-09-24 |
| ATE225359T1 (de) | 2002-10-15 |
| BR9606033A (pt) | 1998-09-01 |
| EP0780396A1 (de) | 1997-06-25 |
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