DE60108231T2 - Substituierte polycyclische cyclopentadiene und verfahren zu ihre herstellung - Google Patents
Substituierte polycyclische cyclopentadiene und verfahren zu ihre herstellung Download PDFInfo
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- DE60108231T2 DE60108231T2 DE60108231T DE60108231T DE60108231T2 DE 60108231 T2 DE60108231 T2 DE 60108231T2 DE 60108231 T DE60108231 T DE 60108231T DE 60108231 T DE60108231 T DE 60108231T DE 60108231 T2 DE60108231 T2 DE 60108231T2
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- 238000000034 method Methods 0.000 title claims description 36
- 238000002360 preparation method Methods 0.000 title description 13
- -1 polycyclic cyclopentadienyl compound Chemical class 0.000 claims description 72
- 150000001875 compounds Chemical class 0.000 claims description 57
- 239000003054 catalyst Substances 0.000 claims description 48
- 229910052751 metal Inorganic materials 0.000 claims description 46
- 239000002184 metal Substances 0.000 claims description 46
- 239000000203 mixture Substances 0.000 claims description 46
- 125000004432 carbon atom Chemical group C* 0.000 claims description 42
- 238000006116 polymerization reaction Methods 0.000 claims description 38
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 28
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 27
- 239000005977 Ethylene Substances 0.000 claims description 27
- 239000004711 α-olefin Substances 0.000 claims description 27
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 claims description 25
- 229910052782 aluminium Inorganic materials 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 20
- 239000000725 suspension Substances 0.000 claims description 20
- 150000001450 anions Chemical class 0.000 claims description 19
- 239000011734 sodium Chemical group 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 17
- 230000009021 linear effect Effects 0.000 claims description 17
- 229910052726 zirconium Inorganic materials 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 13
- 150000001993 dienes Chemical class 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 229910052723 transition metal Inorganic materials 0.000 claims description 11
- 150000003624 transition metals Chemical class 0.000 claims description 11
- 239000004215 Carbon black (E152) Substances 0.000 claims description 10
- 125000000129 anionic group Chemical group 0.000 claims description 10
- 229910052796 boron Inorganic materials 0.000 claims description 10
- 229930195733 hydrocarbon Natural products 0.000 claims description 10
- CPOFMOWDMVWCLF-UHFFFAOYSA-N methyl(oxo)alumane Chemical compound C[Al]=O CPOFMOWDMVWCLF-UHFFFAOYSA-N 0.000 claims description 10
- 230000003647 oxidation Effects 0.000 claims description 10
- 238000007254 oxidation reaction Methods 0.000 claims description 10
- 239000000460 chlorine Substances 0.000 claims description 9
- 150000002430 hydrocarbons Chemical group 0.000 claims description 9
- 239000007788 liquid Substances 0.000 claims description 9
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 230000000737 periodic effect Effects 0.000 claims description 8
- 150000008040 ionic compounds Chemical class 0.000 claims description 7
- 125000000962 organic group Chemical group 0.000 claims description 7
- 125000003367 polycyclic group Chemical group 0.000 claims description 7
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 229910052733 gallium Inorganic materials 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical group 0.000 claims description 6
- 239000010936 titanium Substances 0.000 claims description 6
- 229910052719 titanium Inorganic materials 0.000 claims description 6
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 claims description 5
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical group [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 5
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 150000001768 cations Chemical class 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 150000004678 hydrides Chemical class 0.000 claims description 5
- 150000002500 ions Chemical class 0.000 claims description 5
- 229910052749 magnesium Chemical group 0.000 claims description 5
- 239000011777 magnesium Chemical group 0.000 claims description 5
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 5
- 229910052718 tin Inorganic materials 0.000 claims description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 4
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 4
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 150000007942 carboxylates Chemical class 0.000 claims description 4
- 229910052735 hafnium Inorganic materials 0.000 claims description 4
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 4
- 150000002902 organometallic compounds Chemical class 0.000 claims description 4
- 150000003254 radicals Chemical class 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- 229910052744 lithium Inorganic materials 0.000 claims description 3
- 230000007935 neutral effect Effects 0.000 claims description 3
- 125000002524 organometallic group Chemical group 0.000 claims description 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 239000003701 inert diluent Substances 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- 239000011701 zinc Substances 0.000 claims description 2
- 150000005840 aryl radicals Chemical class 0.000 claims 2
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims 1
- 125000006737 (C6-C20) arylalkyl group Chemical group 0.000 claims 1
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims 1
- 125000002723 alicyclic group Chemical group 0.000 claims 1
- 229910000077 silane Inorganic materials 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 66
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 54
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 45
- 239000000047 product Substances 0.000 description 38
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- 230000015572 biosynthetic process Effects 0.000 description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
- 239000007787 solid Substances 0.000 description 26
- 239000000243 solution Substances 0.000 description 22
- 238000003786 synthesis reaction Methods 0.000 description 21
- 239000002904 solvent Substances 0.000 description 18
- 229920000642 polymer Polymers 0.000 description 17
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- 238000005481 NMR spectroscopy Methods 0.000 description 14
- 230000003197 catalytic effect Effects 0.000 description 14
- 238000007334 copolymerization reaction Methods 0.000 description 14
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 14
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 13
- 238000003756 stirring Methods 0.000 description 13
- 150000001336 alkenes Chemical class 0.000 description 11
- 239000000178 monomer Substances 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 10
- 238000006386 neutralization reaction Methods 0.000 description 10
- 229920006395 saturated elastomer Polymers 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000012074 organic phase Substances 0.000 description 9
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 8
- UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 6
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 6
- XHLHPRDBBAGVEG-UHFFFAOYSA-N 1-tetralone Chemical compound C1=CC=C2C(=O)CCCC2=C1 XHLHPRDBBAGVEG-UHFFFAOYSA-N 0.000 description 6
- BIKNWJXRLLQCCI-UHFFFAOYSA-N 4,5-dihydro-3ah-cyclopenta[a]naphthalene Chemical compound C1=CC=C2C3=CC=CC3CCC2=C1 BIKNWJXRLLQCCI-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- 239000003446 ligand Substances 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
- GCHBULYORREASW-UHFFFAOYSA-L [Cl-].[Cl-].C123C=CC=CC3=CCCC2=CC=C1[Zr+2]C1=CC=C2C11C=CC=CC1=CCC2 Chemical compound [Cl-].[Cl-].C123C=CC=CC3=CCCC2=CC=C1[Zr+2]C1=CC=C2C11C=CC=CC1=CCC2 GCHBULYORREASW-UHFFFAOYSA-L 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- DOKKVPGOHCOXLC-UHFFFAOYSA-N ethyl 1-oxo-3,4-dihydro-2h-naphthalene-2-carboxylate Chemical compound C1=CC=C2C(=O)C(C(=O)OCC)CCC2=C1 DOKKVPGOHCOXLC-UHFFFAOYSA-N 0.000 description 5
- PHNQLQRQSFZXTA-UHFFFAOYSA-N ethyl 5,7-dimethyl-1-oxo-2-(2-oxopropyl)-3,4-dihydronaphthalene-2-carboxylate Chemical compound C1=C(C)C=C2C(=O)C(C(=O)OCC)(CC(C)=O)CCC2=C1C PHNQLQRQSFZXTA-UHFFFAOYSA-N 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 229910003002 lithium salt Inorganic materials 0.000 description 5
- 159000000002 lithium salts Chemical class 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 238000004809 thin layer chromatography Methods 0.000 description 5
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 4
- DPNICLBGUUSDGM-UHFFFAOYSA-N 3a,4,5,6-tetrahydrobenzo[e]azulene Chemical class C1CCC2C=CC=C2C2=CC=CC=C21 DPNICLBGUUSDGM-UHFFFAOYSA-N 0.000 description 4
- 229910007926 ZrCl Inorganic materials 0.000 description 4
- AAVYBPWXXDGMTL-UHFFFAOYSA-L [Cl-].[Cl-].C1CC2=C(C=CC2[Zr++]C2C=CC3=C2CCCc2ccccc32)c2ccccc2C1 Chemical compound [Cl-].[Cl-].C1CC2=C(C=CC2[Zr++]C2C=CC3=C2CCCc2ccccc32)c2ccccc2C1 AAVYBPWXXDGMTL-UHFFFAOYSA-L 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 238000012512 characterization method Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 239000012259 ether extract Substances 0.000 description 4
- VBPABUMPWYNDFV-UHFFFAOYSA-N ethyl 1-oxo-2-(2-oxopropyl)-3,4-dihydronaphthalene-2-carboxylate Chemical compound C1=CC=C2C(=O)C(C(=O)OCC)(CC(C)=O)CCC2=C1 VBPABUMPWYNDFV-UHFFFAOYSA-N 0.000 description 4
- LHNMGYHIXMIZDE-UHFFFAOYSA-N ethyl 1-oxo-2-prop-2-ynyl-3,4-dihydronaphthalene-2-carboxylate Chemical compound C1=CC=C2C(=O)C(C(=O)OCC)(CC#C)CCC2=C1 LHNMGYHIXMIZDE-UHFFFAOYSA-N 0.000 description 4
- IELCFOGQEURADV-UHFFFAOYSA-N ethyl 5,7-dimethyl-1-oxo-3,4-dihydro-2h-naphthalene-2-carboxylate Chemical compound C1=C(C)C=C2C(=O)C(C(=O)OCC)CCC2=C1C IELCFOGQEURADV-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 4
- PRBHEGAFLDMLAL-GQCTYLIASA-N (4e)-hexa-1,4-diene Chemical compound C\C=C\CC=C PRBHEGAFLDMLAL-GQCTYLIASA-N 0.000 description 3
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 3
- DBRSOGDNSUYZCR-UHFFFAOYSA-N 3,3a,4,5-tetrahydrocyclopenta[a]naphthalen-2-one Chemical compound C1=CC=C2C3=CC(=O)CC3CCC2=C1 DBRSOGDNSUYZCR-UHFFFAOYSA-N 0.000 description 3
- FUDNBFMOXDUIIE-UHFFFAOYSA-N 3,7-dimethylocta-1,6-diene Chemical compound C=CC(C)CCC=C(C)C FUDNBFMOXDUIIE-UHFFFAOYSA-N 0.000 description 3
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 3
- 229920002943 EPDM rubber Polymers 0.000 description 3
- 230000005526 G1 to G0 transition Effects 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 229910010082 LiAlH Inorganic materials 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- 229910004298 SiO 2 Inorganic materials 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 230000008034 disappearance Effects 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 150000002085 enols Chemical class 0.000 description 3
- 125000004494 ethyl ester group Chemical group 0.000 description 3
- 238000003818 flash chromatography Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 229940101209 mercuric oxide Drugs 0.000 description 3
- 150000002894 organic compounds Chemical class 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 239000002685 polymerization catalyst Substances 0.000 description 3
- 230000000379 polymerizing effect Effects 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 239000003643 water by type Substances 0.000 description 3
- RJUCIROUEDJQIB-GQCTYLIASA-N (6e)-octa-1,6-diene Chemical compound C\C=C\CCCC=C RJUCIROUEDJQIB-GQCTYLIASA-N 0.000 description 2
- VYXHVRARDIDEHS-UHFFFAOYSA-N 1,5-cyclooctadiene Chemical compound C1CC=CCCC=C1 VYXHVRARDIDEHS-UHFFFAOYSA-N 0.000 description 2
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 2
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- YXRZFCBXBJIBAP-UHFFFAOYSA-N 2,6-dimethylocta-1,7-diene Chemical compound C=CC(C)CCCC(C)=C YXRZFCBXBJIBAP-UHFFFAOYSA-N 0.000 description 2
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 2
- UYJCNOMEGPDXMV-UHFFFAOYSA-N 5,7-dimethyl-3,4-dihydro-2h-naphthalen-1-one Chemical compound C1CCC(=O)C2=CC(C)=CC(C)=C21 UYJCNOMEGPDXMV-UHFFFAOYSA-N 0.000 description 2
- VSQLAQKFRFTMNS-UHFFFAOYSA-N 5-methylhexa-1,4-diene Chemical compound CC(C)=CCC=C VSQLAQKFRFTMNS-UHFFFAOYSA-N 0.000 description 2
- WTQBISBWKRKLIJ-UHFFFAOYSA-N 5-methylidenebicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(=C)CC1C=C2 WTQBISBWKRKLIJ-UHFFFAOYSA-N 0.000 description 2
- CJQNJRMLJAAXOS-UHFFFAOYSA-N 5-prop-1-enylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(C=CC)CC1C=C2 CJQNJRMLJAAXOS-UHFFFAOYSA-N 0.000 description 2
- KWHUHTFXMNQHAA-UHFFFAOYSA-N 6,7,8,9-tetrahydrobenzo[7]annulen-5-one Chemical compound O=C1CCCCC2=CC=CC=C12 KWHUHTFXMNQHAA-UHFFFAOYSA-N 0.000 description 2
- OCUWHDQQWWNFMS-UHFFFAOYSA-N 6,8-dimethyl-4,5-dihydro-3ah-cyclopenta[a]naphthalene Chemical compound C1CC2C=CC=C2C2=CC(C)=CC(C)=C21 OCUWHDQQWWNFMS-UHFFFAOYSA-N 0.000 description 2
- HKMTVMBEALTRRR-UHFFFAOYSA-N Benzo[a]fluorene Chemical compound C1=CC=CC2=C3CC4=CC=CC=C4C3=CC=C21 HKMTVMBEALTRRR-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
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- JZCCFEFSEZPSOG-UHFFFAOYSA-L copper(II) sulfate pentahydrate Chemical compound O.O.O.O.O.[Cu+2].[O-]S([O-])(=O)=O JZCCFEFSEZPSOG-UHFFFAOYSA-L 0.000 description 1
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- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
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- 239000012312 sodium hydride Substances 0.000 description 1
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- 238000012721 stereospecific polymerization Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229920001576 syndiotactic polymer Polymers 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- OBAJXDYVZBHCGT-UHFFFAOYSA-N tris(pentafluorophenyl)borane Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1B(C=1C(=C(F)C(F)=C(F)C=1F)F)C1=C(F)C(F)=C(F)C(F)=C1F OBAJXDYVZBHCGT-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
- B01J31/14—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides of aluminium or boron
- B01J31/143—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides of aluminium or boron of aluminium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
- B01J31/122—Metal aryl or alkyl compounds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
- B01J31/14—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides of aluminium or boron
-
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- Health & Medical Sciences (AREA)
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- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
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| IT2000MI000680A IT1318436B1 (it) | 2000-03-31 | 2000-03-31 | Ciclopentadieni sostituiti policiclici e metodo per la loropreparazione. |
| ITMI000680 | 2000-12-05 | ||
| PCT/EP2001/003127 WO2001074745A1 (en) | 2000-03-31 | 2001-03-20 | Substituted polycyclic cyclopentadienes and method for their preparation |
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| EP2261292B1 (en) | 2002-10-15 | 2014-07-23 | ExxonMobil Chemical Patents Inc. | Polyolefin adhesive compositions |
| US7550528B2 (en) | 2002-10-15 | 2009-06-23 | Exxonmobil Chemical Patents Inc. | Functionalized olefin polymers |
| US7223822B2 (en) | 2002-10-15 | 2007-05-29 | Exxonmobil Chemical Patents Inc. | Multiple catalyst and reactor system for olefin polymerization and polymers produced therefrom |
| US7541402B2 (en) | 2002-10-15 | 2009-06-02 | Exxonmobil Chemical Patents Inc. | Blend functionalized polyolefin adhesive |
| WO2010077163A1 (en) * | 2008-12-30 | 2010-07-08 | Gosudarstvennoe Uchebno-Nauchnoe Uchrezhdenie Khimichesky Fakultet Moskovskogo Gosudarstvennogo Universiteta Im. M.V.Lomonosova | Synthesis of substituted tetrahydroindenyl complexes, metallocenes produced therefrom and use of the metallocenes in polymerisation processes |
| CN111132988B (zh) * | 2017-09-28 | 2023-06-20 | 尤尼威蒂恩技术有限责任公司 | 环状有机化合物和茂金属的合成 |
| JP2022055368A (ja) * | 2019-02-19 | 2022-04-08 | 株式会社三和化学研究所 | ベンゾアゼピン誘導体の製造方法及びその中間体 |
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| AT401520B (de) * | 1994-03-22 | 1996-09-25 | Danubia Petrochem Polymere | Metallocene und deren einsatz für die olefinpolymerisation |
| IT1273420B (it) * | 1994-04-06 | 1997-07-08 | Spherilene Srl | Composti metallocenici, procedimento per la preparazione e loro utilizzo in catalizzatori per la polimerizzazione delle olefine |
| FR2731217B1 (fr) * | 1995-03-03 | 1997-06-13 | Roussel Uclaf | Nouveaux derives tricycliques, leur preparation, leur application a la preparation de la colchicine et de la thiocolchicine optiquement actives ou racemiques et d'analogues ou derives et intermediaires |
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| DE69905011T2 (de) * | 1998-11-18 | 2003-11-06 | Basell Polyolefine Gmbh | Bis(tetrahydro-indenyl) metallocene, und diesen enthaltende olefinpolymerisationskatalysatoren |
| JP2001133886A (ja) * | 1999-08-26 | 2001-05-18 | Kuraray Co Ltd | 背面投射形スクリーン用プラスチックシート |
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| DE60108231D1 (de) | 2005-02-10 |
| ITMI20000680A1 (it) | 2001-10-01 |
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| US6930158B2 (en) | 2005-08-16 |
| JP2003529572A (ja) | 2003-10-07 |
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| MY126014A (en) | 2006-09-29 |
| KR20020081413A (ko) | 2002-10-26 |
| IT1318436B1 (it) | 2003-08-25 |
| US6844478B2 (en) | 2005-01-18 |
| ITMI20000680A0 (it) | 2000-03-31 |
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