NO326005B1 - 3-heteroatom substituerte cyklopentadienyl-inneholdende metallkomplekser og olefinpolymerisasjonsprosess - Google Patents

Info

Publication number

NO326005B1

NO326005B1 NO19990545A NO990545A NO326005B1 NO 326005 B1 NO326005 B1 NO 326005B1 NO 19990545 A NO19990545 A NO 19990545A NO 990545 A NO990545 A NO 990545A NO 326005 B1 NO326005 B1 NO 326005B1

Authority

NO

Norway

Prior art keywords

dimethylethyl

dimethyl

inden

silanaminate

titanium

Prior art date

1996-08-08

Links

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• 238000006116 polymerization reaction Methods 0.000 title claims description 66
• 150000001336 alkenes Chemical class 0.000 title claims description 36
• JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 title claims description 20
• 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 title claims description 17
• ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 title claims description 15
• 229910052751 metal Inorganic materials 0.000 title description 46
• 239000002184 metal Substances 0.000 title description 46
• 239000010936 titanium Substances 0.000 claims description 684
• 229910052719 titanium Inorganic materials 0.000 claims description 365
• RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 346
• -1 hydrocarbylsulfido Chemical group 0.000 claims description 246
• 239000000243 solution Substances 0.000 claims description 175
• 239000003054 catalyst Substances 0.000 claims description 100
• 238000000034 method Methods 0.000 claims description 100
• 125000001183 hydrocarbyl group Chemical group 0.000 claims description 92
• 125000003963 dichloro group Chemical group Cl* 0.000 claims description 78
• 239000000203 mixture Substances 0.000 claims description 74
• 229920000642 polymer Polymers 0.000 claims description 53
• 150000001875 compounds Chemical class 0.000 claims description 47
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 40
• 239000007789 gas Substances 0.000 claims description 38
• 150000001993 dienes Chemical class 0.000 claims description 37
• 239000003446 ligand Substances 0.000 claims description 35
• VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 33
• 239000005977 Ethylene Substances 0.000 claims description 33
• 150000004696 coordination complex Chemical class 0.000 claims description 33
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 32
• 230000008569 process Effects 0.000 claims description 31
• 229910052782 aluminium Inorganic materials 0.000 claims description 28
• 230000003647 oxidation Effects 0.000 claims description 25
• 238000007254 oxidation reaction Methods 0.000 claims description 25
• 239000004711 α-olefin Substances 0.000 claims description 25
• 230000003213 activating effect Effects 0.000 claims description 24
• 229910052757 nitrogen Inorganic materials 0.000 claims description 22
• 239000001257 hydrogen Substances 0.000 claims description 21
• 229910052739 hydrogen Inorganic materials 0.000 claims description 21
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
• 125000004122 cyclic group Chemical group 0.000 claims description 19
• FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 claims description 19
• 239000002002 slurry Substances 0.000 claims description 19
• 125000004432 carbon atom Chemical group C* 0.000 claims description 18
• 125000000217 alkyl group Chemical group 0.000 claims description 16
• 125000003118 aryl group Chemical group 0.000 claims description 16
• 229910052760 oxygen Inorganic materials 0.000 claims description 16
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
• 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 13
• 125000000129 anionic group Chemical group 0.000 claims description 12
• 230000007935 neutral effect Effects 0.000 claims description 12
• 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 12
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
• 239000012876 carrier material Substances 0.000 claims description 10
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
• 239000001301 oxygen Substances 0.000 claims description 9
• FVZVCSNXTFCBQU-UHFFFAOYSA-N phosphanyl Chemical group [PH2] FVZVCSNXTFCBQU-UHFFFAOYSA-N 0.000 claims description 8
• APPOKADJQUIAHP-GGWOSOGESA-N (2e,4e)-hexa-2,4-diene Chemical group C\C=C\C=C\C APPOKADJQUIAHP-GGWOSOGESA-N 0.000 claims description 7
• ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 7
• 239000002879 Lewis base Substances 0.000 claims description 7
• 229910052796 boron Inorganic materials 0.000 claims description 7
• 150000007527 lewis bases Chemical class 0.000 claims description 7
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 6
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
• 229910052698 phosphorus Inorganic materials 0.000 claims description 6
• 229910052726 zirconium Inorganic materials 0.000 claims description 6
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
• 230000000737 periodic effect Effects 0.000 claims description 5
• 229910052717 sulfur Inorganic materials 0.000 claims description 5
• 125000004429 atom Chemical group 0.000 claims description 4
• 229910052799 carbon Inorganic materials 0.000 claims description 4
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
• PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical group C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 claims description 3
• OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 3
• QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 3
• 125000003114 inden-1-yl group Chemical group [H]C1=C([H])C([H])(*)C2=C([H])C([H])=C([H])C([H])=C12 0.000 claims description 3
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
• 239000011574 phosphorus Substances 0.000 claims description 3
• PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Chemical group CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 claims description 3
• JFLKFZNIIQFQBS-FNCQTZNRSA-N trans,trans-1,4-Diphenyl-1,3-butadiene Chemical group C=1C=CC=CC=1\C=C\C=C\C1=CC=CC=C1 JFLKFZNIIQFQBS-FNCQTZNRSA-N 0.000 claims description 3
• OMIVCRYZSXDGAB-UHFFFAOYSA-N 1,4-butanediyl Chemical group [CH2]CC[CH2] OMIVCRYZSXDGAB-UHFFFAOYSA-N 0.000 claims description 2
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
• 229910052800 carbon group element Inorganic materials 0.000 claims description 2
• 239000003426 co-catalyst Substances 0.000 claims description 2
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
• 125000004915 dibutylamino group Chemical group C(CCC)N(CCCC)* 0.000 claims description 2
• 229910052735 hafnium Inorganic materials 0.000 claims description 2
• 229910052809 inorganic oxide Inorganic materials 0.000 claims description 2
• 229910001507 metal halide Inorganic materials 0.000 claims description 2
• 150000005309 metal halides Chemical class 0.000 claims description 2
• 125000002757 morpholinyl group Chemical group 0.000 claims description 2
• 125000003386 piperidinyl group Chemical group 0.000 claims description 2
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 2
• 239000011593 sulfur Substances 0.000 claims description 2
• CMWCOKOTCLFJOP-UHFFFAOYSA-N titanium(3+) Chemical compound [Ti+3] CMWCOKOTCLFJOP-UHFFFAOYSA-N 0.000 claims 2
• 125000005394 methallyl group Chemical group 0.000 claims 1
• UZGLIIJVICEWHF-UHFFFAOYSA-N octogen Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)CN([N+]([O-])=O)C1 UZGLIIJVICEWHF-UHFFFAOYSA-N 0.000 claims 1
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 449
• UHOVQNZJYSORNB-MZWXYZOWSA-N benzene-d6 Chemical compound [2H]C1=C([2H])C([2H])=C([2H])C([2H])=C1[2H] UHOVQNZJYSORNB-MZWXYZOWSA-N 0.000 description 166
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 164
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 124
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 117
• 239000000047 product Substances 0.000 description 103
• 238000002360 preparation method Methods 0.000 description 99
• 239000002904 solvent Substances 0.000 description 84
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 82
• 239000007787 solid Substances 0.000 description 75
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 53
• 238000003756 stirring Methods 0.000 description 47
• MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 46
• 238000007792 addition Methods 0.000 description 45
• 239000013078 crystal Substances 0.000 description 45
• 239000000178 monomer Substances 0.000 description 45
• DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 40
• 238000006243 chemical reaction Methods 0.000 description 35
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 31
• 239000011541 reaction mixture Substances 0.000 description 28
• 238000001914 filtration Methods 0.000 description 27
• 238000004519 manufacturing process Methods 0.000 description 27
• 150000001450 anions Chemical class 0.000 description 26
• 239000007788 liquid Substances 0.000 description 25
• 239000002244 precipitate Substances 0.000 description 25
• 229910003002 lithium salt Inorganic materials 0.000 description 23
• 159000000002 lithium salts Chemical class 0.000 description 23
• 238000005160 1H NMR spectroscopy Methods 0.000 description 22
• 239000000463 material Substances 0.000 description 22
• 239000003921 oil Substances 0.000 description 22
• 235000019198 oils Nutrition 0.000 description 22
• 150000002081 enamines Chemical class 0.000 description 20
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 19
• 229920002943 EPDM rubber Polymers 0.000 description 18
• 125000005842 heteroatom Chemical group 0.000 description 18
• 230000035484 reaction time Effects 0.000 description 18
• 150000003839 salts Chemical class 0.000 description 18
• 230000015572 biosynthetic process Effects 0.000 description 17
• 239000012071 phase Substances 0.000 description 17
• 239000003795 chemical substances by application Substances 0.000 description 16
• 239000000706 filtrate Substances 0.000 description 16
• OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 16
• 238000004458 analytical method Methods 0.000 description 15
• 238000005868 electrolysis reaction Methods 0.000 description 15
• QNXSIUBBGPHDDE-UHFFFAOYSA-N indan-1-one Chemical compound C1=CC=C2C(=O)CCC2=C1 QNXSIUBBGPHDDE-UHFFFAOYSA-N 0.000 description 15
• 238000002955 isolation Methods 0.000 description 15
• LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 14
• 239000003085 diluting agent Substances 0.000 description 14
• 238000005481 NMR spectroscopy Methods 0.000 description 13
• XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 13
• 150000001412 amines Chemical class 0.000 description 13
• 239000000126 substance Substances 0.000 description 13
• 239000003039 volatile agent Substances 0.000 description 13
• VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 12
• KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 12
• WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 12
• WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 12
• 239000003792 electrolyte Substances 0.000 description 12
• 230000006870 function Effects 0.000 description 12
• 229910052744 lithium Inorganic materials 0.000 description 12
• 239000002685 polymerization catalyst Substances 0.000 description 12
• 229920000098 polyolefin Polymers 0.000 description 12
• 229910000077 silane Inorganic materials 0.000 description 12
• 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 11
• 238000012937 correction Methods 0.000 description 11
• 238000009826 distribution Methods 0.000 description 11
• TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 11
• 239000000377 silicon dioxide Substances 0.000 description 11
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 10
• 150000001768 cations Chemical class 0.000 description 10
• 238000013480 data collection Methods 0.000 description 10
• 230000000694 effects Effects 0.000 description 10
• 239000011159 matrix material Substances 0.000 description 10
• GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 10
• QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 10
• 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 10
• BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 9
• 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 9
• 238000010528 free radical solution polymerization reaction Methods 0.000 description 9
• 229930195733 hydrocarbon Natural products 0.000 description 9
• 235000012239 silicon dioxide Nutrition 0.000 description 9
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 8
• 238000010521 absorption reaction Methods 0.000 description 8
• 238000004364 calculation method Methods 0.000 description 8
• 238000010828 elution Methods 0.000 description 8
• 150000004820 halides Chemical class 0.000 description 8
• 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 8
• 150000002576 ketones Chemical class 0.000 description 8
• KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 8
• 150000002739 metals Chemical class 0.000 description 8
• UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 8
• CKWOGTUTBSUNSB-UHFFFAOYSA-N n-[chloro(dimethyl)silyl]-2-methylpropan-2-amine Chemical compound CC(C)(C)N[Si](C)(C)Cl CKWOGTUTBSUNSB-UHFFFAOYSA-N 0.000 description 8
• YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 8
• 238000006467 substitution reaction Methods 0.000 description 8
• 239000000725 suspension Substances 0.000 description 8
• RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 8
• PRBHEGAFLDMLAL-GQCTYLIASA-N (4e)-hexa-1,4-diene Chemical compound C\C=C\CC=C PRBHEGAFLDMLAL-GQCTYLIASA-N 0.000 description 7
• YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 7
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
• PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 7
• 230000004913 activation Effects 0.000 description 7
• 150000004703 alkoxides Chemical class 0.000 description 7
• 239000003638 chemical reducing agent Substances 0.000 description 7
• DMEGYFMYUHOHGS-UHFFFAOYSA-N cycloheptane Chemical compound C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 7
• 238000000746 purification Methods 0.000 description 7
• SCABQASLNUQUKD-UHFFFAOYSA-N silylium Chemical compound [SiH3+] SCABQASLNUQUKD-UHFFFAOYSA-N 0.000 description 7
• XWJBRBSPAODJER-UHFFFAOYSA-N 1,7-octadiene Chemical compound C=CCCCCC=C XWJBRBSPAODJER-UHFFFAOYSA-N 0.000 description 6
• ZGEGCLOFRBLKSE-UHFFFAOYSA-N 1-Heptene Chemical compound CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 6
• AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 6
• 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 6
• AQZWEFBJYQSQEH-UHFFFAOYSA-N 2-methyloxaluminane Chemical compound C[Al]1CCCCO1 AQZWEFBJYQSQEH-UHFFFAOYSA-N 0.000 description 6
• ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 6
• YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 6
• 239000002841 Lewis acid Substances 0.000 description 6
• 150000001491 aromatic compounds Chemical class 0.000 description 6
• 238000009833 condensation Methods 0.000 description 6
• 230000005494 condensation Effects 0.000 description 6
• 238000001816 cooling Methods 0.000 description 6
• 229920001577 copolymer Polymers 0.000 description 6
• SMBQBQBNOXIFSF-UHFFFAOYSA-N dilithium Chemical compound [Li][Li] SMBQBQBNOXIFSF-UHFFFAOYSA-N 0.000 description 6
• 150000002430 hydrocarbons Chemical class 0.000 description 6
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
• HWSZZLVAJGOAAY-UHFFFAOYSA-L lead(II) chloride Chemical compound Cl[Pb]Cl HWSZZLVAJGOAAY-UHFFFAOYSA-L 0.000 description 6
• 150000007517 lewis acids Chemical class 0.000 description 6
• 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 6
• TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 6
• 239000002245 particle Substances 0.000 description 6
• 239000000843 powder Substances 0.000 description 6
• 230000001105 regulatory effect Effects 0.000 description 6
• 230000000087 stabilizing effect Effects 0.000 description 6
• 239000007858 starting material Substances 0.000 description 6
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
• 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 5
• PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical class [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 5
• COOXAWDWHWRVRD-UHFFFAOYSA-N C[Ti]C Chemical compound C[Ti]C COOXAWDWHWRVRD-UHFFFAOYSA-N 0.000 description 5
• 229920000089 Cyclic olefin copolymer Polymers 0.000 description 5
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 5
• FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 5
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 5
• UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 5
• 238000004821 distillation Methods 0.000 description 5
• 238000001035 drying Methods 0.000 description 5
• 150000002170 ethers Chemical class 0.000 description 5
• 238000004817 gas chromatography Methods 0.000 description 5
• 238000011065 in-situ storage Methods 0.000 description 5
• NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 5
• SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 description 5
• 125000002524 organometallic group Chemical group 0.000 description 5
• NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 5
• 229910052700 potassium Inorganic materials 0.000 description 5
• 239000011591 potassium Substances 0.000 description 5
• 239000011734 sodium Substances 0.000 description 5
• 238000011282 treatment Methods 0.000 description 5
• 239000008096 xylene Substances 0.000 description 5
• OJOWICOBYCXEKR-KRXBUXKQSA-N (5e)-5-ethylidenebicyclo[2.2.1]hept-2-ene Chemical group C1C2C(=C/C)/CC1C=C2 OJOWICOBYCXEKR-KRXBUXKQSA-N 0.000 description 4
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