CA2259582A1 - Polymerization processes for olefins - Google Patents
Polymerization processes for olefins Download PDFInfo
- Publication number
- CA2259582A1 CA2259582A1 CA002259582A CA2259582A CA2259582A1 CA 2259582 A1 CA2259582 A1 CA 2259582A1 CA 002259582 A CA002259582 A CA 002259582A CA 2259582 A CA2259582 A CA 2259582A CA 2259582 A1 CA2259582 A1 CA 2259582A1
- Authority
- CA
- Canada
- Prior art keywords
- independently
- hydrocarbyl
- meph
- compound
- recited
- 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.)
- Abandoned
Links
- 150000001336 alkenes Chemical class 0.000 title claims abstract description 43
- 238000006116 polymerization reaction Methods 0.000 title claims description 45
- 150000001875 compounds Chemical class 0.000 claims abstract description 55
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims abstract description 54
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 claims abstract description 52
- 238000000034 method Methods 0.000 claims abstract description 35
- 230000008569 process Effects 0.000 claims abstract description 33
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 31
- -1 ethylene Chemical class 0.000 claims abstract description 30
- 229910052759 nickel Inorganic materials 0.000 claims abstract description 29
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims abstract description 26
- 229910052763 palladium Inorganic materials 0.000 claims abstract description 22
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000005977 Ethylene Substances 0.000 claims abstract description 8
- 229910052751 metal Inorganic materials 0.000 claims abstract description 8
- 239000002184 metal Substances 0.000 claims abstract description 8
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 60
- 125000004432 carbon atom Chemical group C* 0.000 claims description 38
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 32
- 125000003118 aryl group Chemical group 0.000 claims description 28
- 229910052799 carbon Inorganic materials 0.000 claims description 22
- 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 claims description 22
- 125000000743 hydrocarbylene group Chemical group 0.000 claims description 15
- 150000001450 anions Chemical class 0.000 claims description 13
- 239000000460 chlorine Substances 0.000 claims description 13
- 125000003107 substituted aryl group Chemical group 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 229910052794 bromium Inorganic materials 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 claims description 10
- 150000002367 halogens Chemical group 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 8
- PQLAYKMGZDUDLQ-UHFFFAOYSA-K aluminium bromide Chemical compound Br[Al](Br)Br PQLAYKMGZDUDLQ-UHFFFAOYSA-K 0.000 claims description 7
- 125000002837 carbocyclic group Chemical group 0.000 claims description 7
- NALBLJLOBICXRH-UHFFFAOYSA-N dinitrogen monohydride Chemical group N=[N] NALBLJLOBICXRH-UHFFFAOYSA-N 0.000 claims description 7
- 239000003446 ligand Substances 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- WXHIJDCHNDBCNY-UHFFFAOYSA-N palladium dihydride Chemical compound [PdH2] WXHIJDCHNDBCNY-UHFFFAOYSA-N 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 150000002941 palladium compounds Chemical class 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 229910052782 aluminium Inorganic materials 0.000 claims description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical group [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 4
- CFBGXYDUODCMNS-UHFFFAOYSA-N cyclobutene Chemical compound C1CC=C1 CFBGXYDUODCMNS-UHFFFAOYSA-N 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 229910052725 zinc Inorganic materials 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 229920001400 block copolymer Polymers 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 229920005604 random copolymer Polymers 0.000 claims description 2
- 229910052718 tin Inorganic materials 0.000 claims 3
- 101100495913 Arabidopsis thaliana CHR17 gene Proteins 0.000 claims 2
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims 1
- 229910000071 diazene Inorganic materials 0.000 abstract description 8
- 239000003054 catalyst Substances 0.000 abstract description 5
- 229920000098 polyolefin Polymers 0.000 abstract description 4
- 239000002841 Lewis acid Substances 0.000 abstract description 3
- 150000007517 lewis acids Chemical class 0.000 abstract description 3
- 229920001971 elastomer Polymers 0.000 abstract description 2
- 239000000806 elastomer Substances 0.000 abstract description 2
- 239000010408 film Substances 0.000 abstract description 2
- 238000000465 moulding Methods 0.000 abstract description 2
- 229920005989 resin Polymers 0.000 abstract description 2
- 239000011347 resin Substances 0.000 abstract description 2
- MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical class [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 88
- 229920000642 polymer Polymers 0.000 description 36
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 28
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 26
- 239000011541 reaction mixture Substances 0.000 description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- 150000001721 carbon Chemical group 0.000 description 14
- 229910052757 nitrogen Inorganic materials 0.000 description 13
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 12
- 229910021585 Nickel(II) bromide Inorganic materials 0.000 description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
- IPLJNQFXJUCRNH-UHFFFAOYSA-L nickel(2+);dibromide Chemical compound [Ni+2].[Br-].[Br-] IPLJNQFXJUCRNH-UHFFFAOYSA-L 0.000 description 10
- 239000000203 mixture Substances 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 239000002168 alkylating agent Substances 0.000 description 7
- 239000012018 catalyst precursor Substances 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000000178 monomer Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 6
- 229940100198 alkylating agent Drugs 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- CPOFMOWDMVWCLF-UHFFFAOYSA-N methyl(oxo)alumane Chemical class C[Al]=O CPOFMOWDMVWCLF-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-DICFDUPASA-N dichloromethane-d2 Chemical compound [2H]C([2H])(Cl)Cl YMWUJEATGCHHMB-DICFDUPASA-N 0.000 description 4
- HQWPLXHWEZZGKY-UHFFFAOYSA-N diethylzinc Chemical compound CC[Zn]CC HQWPLXHWEZZGKY-UHFFFAOYSA-N 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- BMGNSKKZFQMGDH-FDGPNNRMSA-L nickel(2+);(z)-4-oxopent-2-en-2-olate Chemical compound [Ni+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O BMGNSKKZFQMGDH-FDGPNNRMSA-L 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- YWADYUWJRWZMSS-UHFFFAOYSA-N 2,6-dichloro-4-methoxyaniline Chemical compound COC1=CC(Cl)=C(N)C(Cl)=C1 YWADYUWJRWZMSS-UHFFFAOYSA-N 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 150000002848 norbornenes Chemical class 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 3
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 3
- 101100277337 Arabidopsis thaliana DDM1 gene Proteins 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
- 101150113676 chr1 gene Proteins 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000001072 heteroaryl group Chemical group 0.000 description 2
- 229960004592 isopropanol Drugs 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- JKDRQYIYVJVOPF-FDGPNNRMSA-L palladium(ii) acetylacetonate Chemical compound [Pd+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O JKDRQYIYVJVOPF-FDGPNNRMSA-L 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 229960001866 silicon dioxide Drugs 0.000 description 2
- 230000003335 steric effect Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000007306 turnover Effects 0.000 description 2
- OJOWICOBYCXEKR-APPZFPTMSA-N (1S,4R)-5-ethylidenebicyclo[2.2.1]hept-2-ene Chemical compound CC=C1C[C@@H]2C[C@@H]1C=C2 OJOWICOBYCXEKR-APPZFPTMSA-N 0.000 description 1
- 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 1
- 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 1
- LKAQFOKMMXWRRQ-UHFFFAOYSA-N 2-chloro-4,6-dimethylaniline Chemical compound CC1=CC(C)=C(N)C(Cl)=C1 LKAQFOKMMXWRRQ-UHFFFAOYSA-N 0.000 description 1
- WFNLHDJJZSJARK-UHFFFAOYSA-N 2-chloro-6-methylaniline Chemical compound CC1=CC=CC(Cl)=C1N WFNLHDJJZSJARK-UHFFFAOYSA-N 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- INYHZQLKOKTDAI-UHFFFAOYSA-N 5-ethenylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(C=C)CC1C=C2 INYHZQLKOKTDAI-UHFFFAOYSA-N 0.000 description 1
- WMWDGZLDLRCDRG-UHFFFAOYSA-N 5-hexylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(CCCCCC)CC1C=C2 WMWDGZLDLRCDRG-UHFFFAOYSA-N 0.000 description 1
- PCBPVYHMZBWMAZ-UHFFFAOYSA-N 5-methylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(C)CC1C=C2 PCBPVYHMZBWMAZ-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 101100495914 Arabidopsis thaliana ETL1 gene Proteins 0.000 description 1
- 101150041968 CDC13 gene Proteins 0.000 description 1
- 241000365446 Cordierites Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 150000004703 alkoxides Chemical group 0.000 description 1
- 125000001118 alkylidene group Chemical group 0.000 description 1
- HFDVRLIODXPAHB-UHFFFAOYSA-N alpha-tetradecene Natural products CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical group [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 125000003636 chemical group Chemical group 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- HANKSFAYJLDDKP-UHFFFAOYSA-N dihydrodicyclopentadiene Chemical compound C12CC=CC2C2CCC1C2 HANKSFAYJLDDKP-UHFFFAOYSA-N 0.000 description 1
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- KWKAKUADMBZCLK-UHFFFAOYSA-N methyl heptene Natural products CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Chemical group 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 229960004029 silicic acid Drugs 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000005648 substituted hydrocarbylene group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 239000002352 surface water Substances 0.000 description 1
- XBFJAVXCNXDMBH-UHFFFAOYSA-N tetracyclo[6.2.1.1(3,6).0(2,7)]dodec-4-ene Chemical compound C1C(C23)C=CC1C3C1CC2CC1 XBFJAVXCNXDMBH-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- 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
- C08F32/00—Homopolymers and copolymers of cyclic compounds having no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system
- C08F32/08—Homopolymers and copolymers of cyclic compounds having no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system having two condensed rings
-
- 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
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
- C08F4/70—Iron group metals, platinum group metals or compounds thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
- C07C251/20—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups being part of rings other than six-membered aromatic rings
-
- 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
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/04—Nickel compounds
- C07F15/045—Nickel compounds without a metal-carbon linkage
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
-
- C—CHEMISTRY; METALLURGY
- 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
- C08F297/00—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer
- C08F297/06—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer using a catalyst of the coordination type
- C08F297/08—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer using a catalyst of the coordination type polymerising mono-olefins
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/20—Acenaphthenes; Hydrogenated acenaphthenes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F110/00—Homopolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F110/14—Monomers containing five or more carbon atoms
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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)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US2229596P | 1996-07-23 | 1996-07-23 | |
| US60/022,295 | 1996-07-23 | ||
| US2279696P | 1996-07-30 | 1996-07-30 | |
| US60/022,796 | 1996-07-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2259582A1 true CA2259582A1 (en) | 1998-01-29 |
Family
ID=26695762
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002259582A Abandoned CA2259582A1 (en) | 1996-07-23 | 1997-07-21 | Polymerization processes for olefins |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US5852145A (enExample) |
| EP (1) | EP0914354B1 (enExample) |
| JP (1) | JP2000515195A (enExample) |
| KR (1) | KR100469185B1 (enExample) |
| CN (1) | CN1226256A (enExample) |
| AT (1) | ATE277091T1 (enExample) |
| AU (1) | AU3961797A (enExample) |
| BR (1) | BR9710881A (enExample) |
| CA (1) | CA2259582A1 (enExample) |
| DE (1) | DE69730838T2 (enExample) |
| EA (1) | EA199900152A1 (enExample) |
| IL (1) | IL127865A0 (enExample) |
| WO (1) | WO1998003559A1 (enExample) |
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| DE69826001T2 (de) * | 1997-06-09 | 2005-09-08 | Promerus Llc, Brecksville | Verfahren zur herstellung von copolymeren von ethylen and norbornen-typ monomeren mit cationischen palladium-katalysatoren |
| DE19729817A1 (de) * | 1997-07-11 | 1999-01-14 | Basf Ag | Polymerisation von Cyclopentadien mit kationischen Palladium-Komplexen |
| HUP0004538A2 (hu) * | 1997-12-19 | 2001-04-28 | Phillips Petroleum Co. | Nikkel-diimin katalizátorok metil-alumoxán kokatalizátorral, eljárás ezen katalizátorokkal történő olefin polimerizációra és az előállított polimerek |
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| WO2003011876A1 (en) * | 2001-08-01 | 2003-02-13 | Shell Internationale Research Maatschappij B.V. | Ligands and catalyst systems thereof for ethylene oligomerisation to linear alpha olefins |
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| US6737130B2 (en) | 2001-11-06 | 2004-05-18 | Cryovac, Inc. | Hermetically heat-sealable, pressure-reclosable packaging article containing substantially spherical homogeneous polyolefin |
| DE60305715T2 (de) * | 2002-09-25 | 2007-05-31 | Shell Internationale Research Maatschappij B.V. | Katalysatorsysteme für die ethylen-oligomerisierung zu linearen alpha-olefinen |
| KR100526402B1 (ko) * | 2002-11-22 | 2005-11-08 | 주식회사 엘지화학 | 고리형 올레핀계 부가 중합체를 포함하는 네가티브Ｃ-플레이트(ｎｅｇａｔｉｖｅ Ｃ-ｐｌａｔｅ)형 광학이방성 필름 및 이의 제조방법 |
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| EP1758848A1 (en) * | 2004-04-27 | 2007-03-07 | University Of North Carolina At Chapel Hill | Separation of unsymmetrical diimines by liquid chromatography |
| DE102004027332A1 (de) | 2004-06-04 | 2005-12-22 | Basell Polyolefine Gmbh | Übergangsmetallverbindung, Ligandsystem, Katalysatorsystem und Verfahren zur Herstellung von Polyolefinen |
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| JP2009507114A (ja) * | 2005-09-06 | 2009-02-19 | バーゼル・ポリオレフィン・ゲーエムベーハー | フォトクロミック基を有する触媒系の存在下でオレフィンポリマーを製造する方法 |
| DE102005057559A1 (de) * | 2005-11-30 | 2007-05-31 | Basell Polyolefine Gmbh | Übergangsmetallverbindung, Ligandsystem, Katalysatorsystem und Verfahren zur Herstellung von Polyolefinen |
| DE102006001959A1 (de) | 2006-01-13 | 2007-07-19 | Basell Polyolefine Gmbh | Verfahren zur Herstellung von unsymmetrischen Bis(imino)verbindungen |
| CN100395268C (zh) * | 2006-05-11 | 2008-06-18 | 复旦大学 | 氮氮双齿配体的三配位一价态镍烯烃聚合催化剂及其制备方法 |
| DE102007017903A1 (de) | 2007-04-13 | 2008-10-16 | Basell Polyolefine Gmbh | Polyethylen und Katalysatorzusammensetzung und Verfahren zu dessen Herstellung |
| CN100560613C (zh) * | 2007-11-15 | 2009-11-18 | 中国石油天然气股份有限公司 | 一种烯烃聚合催化剂的制备方法 |
| ATE535552T1 (de) * | 2007-12-21 | 2011-12-15 | Basell Polyolefine Gmbh | Phenantrolinhaltige komplexe |
| CN101619111B (zh) * | 2008-07-03 | 2012-05-09 | 中国石油天然气股份有限公司 | 硅胶负载α-双亚胺镍烯烃聚合催化剂及制备方法和应用 |
| CA2688217C (en) * | 2009-12-11 | 2016-07-12 | Nova Chemicals Corporation | Multi reactor process |
| CN102180910B (zh) * | 2011-03-11 | 2014-03-12 | 中国科学院化学研究所 | 不对称α二亚胺镍配合物催化剂及其制备方法与应用 |
| US8697821B1 (en) * | 2013-06-10 | 2014-04-15 | King Fahd University Of Petroleum And Minerals | Pressure sensitive adhesive |
| CA2864573C (en) | 2014-09-22 | 2021-07-06 | Nova Chemicals Corporation | Shrink film from single site catalyzed polyethylene |
| CA2874895C (en) | 2014-12-16 | 2022-02-15 | Nova Chemicals Corporation | High modulus single-site lldpe |
| CN105936659B (zh) * | 2015-12-03 | 2018-01-30 | 宜春学院 | 立体结构n,n‑单配体金属催化剂及其制备方法 |
| CN108003259B (zh) * | 2016-10-27 | 2021-01-05 | 浙江大学 | 亚乙烯基苊（α-二亚胺）镍烯烃催化剂、制备方法及应用 |
| CN108359036B (zh) * | 2017-01-26 | 2020-07-24 | 中国石油化工股份有限公司 | 一种乙烯与端烯基硅烷/硅氧烷的共聚方法 |
| CN108484549A (zh) * | 2018-05-15 | 2018-09-04 | 江苏奥克化学有限公司 | 一种化合物、配合物及制备方法和用途 |
| US11591419B2 (en) | 2018-12-07 | 2023-02-28 | Exxon Mobil Technology and Engineering Company | Processes for polymerizing internal olefins and compositions thereof |
| SG11202108215PA (en) | 2019-04-01 | 2021-10-28 | Exxonmobil Res & Eng Co | Processes for polymerizing alpha-olefins, internal olefins and compositions thereof |
| CN110302836B (zh) * | 2019-06-21 | 2022-03-15 | 广东药科大学 | 一种氧化石墨烯负载二亚胺配位钯的制备方法及其应用 |
| CN112898465B (zh) * | 2021-01-22 | 2023-08-11 | 吴军化 | 一种高热稳定性铁催化剂及其制备方法 |
| CN112759710B (zh) * | 2021-01-22 | 2023-09-08 | 吴军化 | 一种对位苯氧基取代的α-二亚胺铁催化剂及其制备方法 |
| CN112812208A (zh) * | 2021-03-01 | 2021-05-18 | 扬州工业职业技术学院 | 一种对位硝基取代的α-二亚胺铁催化剂及其应用 |
| EP4330294A1 (en) | 2021-04-30 | 2024-03-06 | ExxonMobil Chemical Patents Inc. | Processes for transitioning between different polymerization catalysts in a polymerization reactor |
| CN117510375A (zh) * | 2023-10-31 | 2024-02-06 | 浙江巨化技术中心有限公司 | 二亚胺配体及其制备方法和应用 |
| CN118754917B (zh) * | 2024-09-09 | 2025-01-17 | 安徽中科科乐化工科技有限责任公司 | α-二亚胺配体化合物、镍配合物、复合配合物及其制备方法和应用 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5465185A (en) * | 1977-11-04 | 1979-05-25 | Fuji Photo Film Co Ltd | Stablizing method for organic basic substance to light |
| ES2071086T5 (es) * | 1989-10-30 | 2002-01-16 | Fina Technology | Preparacion de catalizadores metalocenicos para polimerizacion de olefina. |
| EP0619335B1 (en) * | 1993-04-06 | 1999-04-28 | BP Chemicals Limited | Catalyst composition |
| KR100418168B1 (ko) * | 1995-01-24 | 2004-02-14 | 이.아이,듀우판드네모아앤드캄파니 | 중합 방법 |
| US5714556A (en) * | 1995-06-30 | 1998-02-03 | E. I. Dupont De Nemours And Company | Olefin polymerization process |
| JPH09302020A (ja) * | 1996-03-14 | 1997-11-25 | Mitsui Petrochem Ind Ltd | オレフィン重合体の製造方法 |
| WO1997048736A1 (en) * | 1996-06-17 | 1997-12-24 | Exxon Chemical Patents Inc. | Supported late transition metal catalyst systems |
-
1997
- 1997-07-21 AU AU39617/97A patent/AU3961797A/en not_active Abandoned
- 1997-07-21 CA CA002259582A patent/CA2259582A1/en not_active Abandoned
- 1997-07-21 IL IL12786597A patent/IL127865A0/xx unknown
- 1997-07-21 DE DE69730838T patent/DE69730838T2/de not_active Expired - Lifetime
- 1997-07-21 JP JP10507183A patent/JP2000515195A/ja active Pending
- 1997-07-21 AT AT97936993T patent/ATE277091T1/de not_active IP Right Cessation
- 1997-07-21 BR BR9710881-2A patent/BR9710881A/pt not_active Application Discontinuation
- 1997-07-21 CN CN97196665A patent/CN1226256A/zh active Pending
- 1997-07-21 KR KR10-1999-7000522A patent/KR100469185B1/ko not_active Expired - Fee Related
- 1997-07-21 EP EP97936993A patent/EP0914354B1/en not_active Expired - Lifetime
- 1997-07-21 EA EA199900152A patent/EA199900152A1/ru unknown
- 1997-07-21 US US08/897,805 patent/US5852145A/en not_active Expired - Lifetime
- 1997-07-21 WO PCT/US1997/012801 patent/WO1998003559A1/en not_active Ceased
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1998
- 1998-10-14 US US09/172,367 patent/US6002034A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| DE69730838D1 (de) | 2004-10-28 |
| IL127865A0 (en) | 1999-10-28 |
| WO1998003559A1 (en) | 1998-01-29 |
| JP2000515195A (ja) | 2000-11-14 |
| KR100469185B1 (ko) | 2005-01-31 |
| EP0914354B1 (en) | 2004-09-22 |
| EA199900152A1 (ru) | 1999-08-26 |
| US6002034A (en) | 1999-12-14 |
| KR20000067989A (ko) | 2000-11-25 |
| CN1226256A (zh) | 1999-08-18 |
| EP0914354A1 (en) | 1999-05-12 |
| ATE277091T1 (de) | 2004-10-15 |
| US5852145A (en) | 1998-12-22 |
| BR9710881A (pt) | 1999-09-08 |
| DE69730838T2 (de) | 2006-02-16 |
| AU3961797A (en) | 1998-02-10 |
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