NL1003008C2 - Met een heteroatoom-bevattende groep gesubstitueerde cyclopentadieen- verbinding. - Google Patents
Met een heteroatoom-bevattende groep gesubstitueerde cyclopentadieen- verbinding. Download PDFInfo
- Publication number
- NL1003008C2 NL1003008C2 NL1003008A NL1003008A NL1003008C2 NL 1003008 C2 NL1003008 C2 NL 1003008C2 NL 1003008 A NL1003008 A NL 1003008A NL 1003008 A NL1003008 A NL 1003008A NL 1003008 C2 NL1003008 C2 NL 1003008C2
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- Netherlands
- Prior art keywords
- group
- cyclopentadiene
- added
- mmol
- iii
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- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 title claims abstract description 97
- 125000005842 heteroatom Chemical group 0.000 title claims abstract description 23
- -1 Cyclopentadiene compound Chemical group 0.000 title claims description 96
- 150000001875 compounds Chemical class 0.000 claims abstract description 56
- 125000001424 substituent group Chemical group 0.000 claims abstract description 34
- 239000003446 ligand Substances 0.000 claims abstract description 16
- 239000003054 catalyst Substances 0.000 claims abstract description 14
- 230000000737 periodic effect Effects 0.000 claims abstract description 13
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims abstract description 6
- 239000004711 α-olefin Substances 0.000 claims abstract description 5
- 125000005647 linker group Chemical group 0.000 claims abstract description 4
- 229910052751 metal Inorganic materials 0.000 claims description 31
- 239000002184 metal Substances 0.000 claims description 31
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 22
- 229910052757 nitrogen Inorganic materials 0.000 claims description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 150000004696 coordination complex Chemical class 0.000 claims description 8
- 229930195733 hydrocarbon Natural products 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 229910052698 phosphorus Inorganic materials 0.000 claims description 7
- 239000004215 Carbon black (E152) Substances 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 230000000379 polymerizing effect Effects 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 2
- 239000013589 supplement Substances 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 abstract description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 265
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 159
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 115
- 239000000243 solution Substances 0.000 description 86
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 80
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 78
- 239000011541 reaction mixture Substances 0.000 description 74
- 238000003756 stirring Methods 0.000 description 70
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 67
- 238000006243 chemical reaction Methods 0.000 description 59
- 239000000203 mixture Substances 0.000 description 50
- 238000002360 preparation method Methods 0.000 description 50
- 239000003208 petroleum Substances 0.000 description 49
- 229960004132 diethyl ether Drugs 0.000 description 48
- 239000000047 product Substances 0.000 description 48
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 48
- 239000010936 titanium Substances 0.000 description 46
- 238000004817 gas chromatography Methods 0.000 description 39
- 230000015572 biosynthetic process Effects 0.000 description 32
- 238000003786 synthesis reaction Methods 0.000 description 32
- 239000002904 solvent Substances 0.000 description 30
- 239000010410 layer Substances 0.000 description 22
- 238000004821 distillation Methods 0.000 description 18
- 238000006116 polymerization reaction Methods 0.000 description 18
- 239000000725 suspension Substances 0.000 description 18
- 238000001704 evaporation Methods 0.000 description 17
- 230000008020 evaporation Effects 0.000 description 17
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 16
- 239000003921 oil Substances 0.000 description 16
- 150000002900 organolithium compounds Chemical class 0.000 description 16
- 239000007787 solid Substances 0.000 description 16
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 14
- 238000001816 cooling Methods 0.000 description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
- 238000000034 method Methods 0.000 description 13
- 239000000741 silica gel Substances 0.000 description 13
- 229910002027 silica gel Inorganic materials 0.000 description 13
- 238000012512 characterization method Methods 0.000 description 12
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 12
- 229910052744 lithium Inorganic materials 0.000 description 12
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 12
- 238000005481 NMR spectroscopy Methods 0.000 description 11
- 239000000706 filtrate Substances 0.000 description 11
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 11
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 11
- 238000005160 1H NMR spectroscopy Methods 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 10
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
- 239000002585 base Substances 0.000 description 10
- 238000011065 in-situ storage Methods 0.000 description 10
- 239000012074 organic phase Substances 0.000 description 10
- 229910052938 sodium sulfate Inorganic materials 0.000 description 10
- 235000011152 sodium sulphate Nutrition 0.000 description 10
- 238000006467 substitution reaction Methods 0.000 description 10
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 9
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 9
- 150000004820 halides Chemical class 0.000 description 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 9
- 238000000746 purification Methods 0.000 description 9
- 239000002002 slurry Substances 0.000 description 9
- ZWYDDDAMNQQZHD-UHFFFAOYSA-L titanium(ii) chloride Chemical compound [Cl-].[Cl-].[Ti+2] ZWYDDDAMNQQZHD-UHFFFAOYSA-L 0.000 description 9
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 8
- 239000005977 Ethylene Substances 0.000 description 8
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 8
- 229910052700 potassium Inorganic materials 0.000 description 8
- VNPQQEYMXYCAEZ-UHFFFAOYSA-N 1,2,3,4-tetramethylcyclopenta-1,3-diene Chemical compound CC1=C(C)C(C)=C(C)C1 VNPQQEYMXYCAEZ-UHFFFAOYSA-N 0.000 description 7
- UMAHMMJKEZXFRU-UHFFFAOYSA-N 1,2,3-tri(propan-2-yl)cyclopenta-1,3-diene Chemical compound CC(C)C1=C(C(C)C)C(C(C)C)=CC1 UMAHMMJKEZXFRU-UHFFFAOYSA-N 0.000 description 7
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 7
- 150000001336 alkenes Chemical class 0.000 description 7
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- 238000004440 column chromatography Methods 0.000 description 7
- 239000002270 dispersing agent Substances 0.000 description 7
- 239000000178 monomer Substances 0.000 description 7
- 239000012299 nitrogen atmosphere Substances 0.000 description 7
- 238000005191 phase separation Methods 0.000 description 7
- 239000003444 phase transfer catalyst Substances 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- UXQAEOWCSOPBLF-UHFFFAOYSA-N 2,2,3,3-tetramethyloctane Chemical compound CCCCCC(C)(C)C(C)(C)C UXQAEOWCSOPBLF-UHFFFAOYSA-N 0.000 description 6
- VZHGAHCLYCIJRM-UHFFFAOYSA-N C[Ti+]C Chemical compound C[Ti+]C VZHGAHCLYCIJRM-UHFFFAOYSA-N 0.000 description 6
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 6
- BKJOSQBYAJQEQD-UHFFFAOYSA-L [Cl-].[Cl-].[Ti+3] Chemical compound [Cl-].[Cl-].[Ti+3] BKJOSQBYAJQEQD-UHFFFAOYSA-L 0.000 description 6
- 239000011591 potassium Substances 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 229910052719 titanium Inorganic materials 0.000 description 6
- TTXDTKOSGXSEGK-UHFFFAOYSA-N (1-cyclohexylcyclopenta-2,4-dien-1-yl)cyclohexane Chemical compound C1(CCCCC1)C1(C=CC=C1)C1CCCCC1 TTXDTKOSGXSEGK-UHFFFAOYSA-N 0.000 description 5
- HWKUGMWRLGPQBP-UHFFFAOYSA-N 2-(dimethylamino)ethyl 4-methylbenzenesulfonate Chemical compound CN(C)CCOS(=O)(=O)C1=CC=C(C)C=C1 HWKUGMWRLGPQBP-UHFFFAOYSA-N 0.000 description 5
- NAMYKGVDVNBCFQ-UHFFFAOYSA-N 2-bromopropane Chemical compound CC(C)Br NAMYKGVDVNBCFQ-UHFFFAOYSA-N 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- RVUMUBOXGHTMGZ-UHFFFAOYSA-N n,n-dimethyl-2-[2,3,4-tri(propan-2-yl)cyclopenta-1,3-dien-1-yl]ethanamine Chemical compound CC(C)C1=C(C(C)C)C(C(C)C)=C(CCN(C)C)C1 RVUMUBOXGHTMGZ-UHFFFAOYSA-N 0.000 description 5
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 5
- IBYHHJPAARCAIE-UHFFFAOYSA-N 1-bromo-2-chloroethane Chemical compound ClCCBr IBYHHJPAARCAIE-UHFFFAOYSA-N 0.000 description 4
- PEXDFKDVSAZMCO-UHFFFAOYSA-N 2-(5,5-dicyclohexylcyclopenta-1,3-dien-1-yl)-N,N-dimethylethanamine Chemical compound CN(C)CCC1=CC=CC1(C1CCCCC1)C1CCCCC1 PEXDFKDVSAZMCO-UHFFFAOYSA-N 0.000 description 4
- LNRDDDZJWNIJNF-UHFFFAOYSA-N 2-[5,5-di(propan-2-yl)cyclopenta-1,3-dien-1-yl]-N,N-dimethylethanamine Chemical compound CN(C)CCC1=CC=CC1(C(C)C)C(C)C LNRDDDZJWNIJNF-UHFFFAOYSA-N 0.000 description 4
- PGKZNDZDZDYMFJ-UHFFFAOYSA-N 5,5-di(butan-2-yl)cyclopenta-1,3-diene Chemical compound CC(CC)C1(C=CC=C1)C(C)CC PGKZNDZDZDYMFJ-UHFFFAOYSA-N 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 4
- BZKFMUIJRXWWQK-UHFFFAOYSA-N Cyclopentenone Chemical class O=C1CCC=C1 BZKFMUIJRXWWQK-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 description 4
- 125000003710 aryl alkyl group Chemical group 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- SJEUCMAOSGSDFY-UHFFFAOYSA-N chloromethyl-dimethyl-(2,3,4,5-tetramethylcyclopenta-2,4-dien-1-yl)silane Chemical compound CC1=C(C)C(C)=C(C)C1[Si](C)(C)CCl SJEUCMAOSGSDFY-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 4
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- HYKLMSLCZHLCMQ-UHFFFAOYSA-N (2,3-dicyclohexylcyclopenta-1,3-dien-1-yl)cyclohexane Chemical compound C1CCCCC1C1=C(C2CCCCC2)CC=C1C1CCCCC1 HYKLMSLCZHLCMQ-UHFFFAOYSA-N 0.000 description 3
- KWTZIBAZTUDEOA-UHFFFAOYSA-N 1-[1-(2-phenylpropyl)cyclopenta-2,4-dien-1-yl]propan-2-ylbenzene Chemical compound C1(=CC=CC=C1)C(CC1(C=CC=C1)CC(C)C1=CC=CC=C1)C KWTZIBAZTUDEOA-UHFFFAOYSA-N 0.000 description 3
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 3
- HILJWHUIEBFFEW-UHFFFAOYSA-N 2-butylcyclopenta-1,3-diene Chemical compound CCCCC1=CCC=C1 HILJWHUIEBFFEW-UHFFFAOYSA-N 0.000 description 3
- WKZUZGPZSXUBFQ-UHFFFAOYSA-N 2-pentylcyclopenta-1,3-diene Chemical compound CCCCCC1=CCC=C1 WKZUZGPZSXUBFQ-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound 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 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- QSXVYHHWZVPHNW-UHFFFAOYSA-N [5,5-di(propan-2-yl)cyclopenta-1,3-dien-1-yl]cyclohexane Chemical compound CC(C)C1(C=CC=C1C1CCCCC1)C(C)C QSXVYHHWZVPHNW-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 239000007864 aqueous solution 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
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 150000001649 bromium compounds Chemical class 0.000 description 3
- AQNQQHJNRPDOQV-UHFFFAOYSA-N bromocyclohexane Chemical compound BrC1CCCCC1 AQNQQHJNRPDOQV-UHFFFAOYSA-N 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 238000007334 copolymerization reaction Methods 0.000 description 3
- 150000001993 dienes Chemical class 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 3
- UBHZUDXTHNMNLD-UHFFFAOYSA-N dimethylsilane Chemical compound C[SiH2]C UBHZUDXTHNMNLD-UHFFFAOYSA-N 0.000 description 3
- 229940052303 ethers for general anesthesia Drugs 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 150000004714 phosphonium salts Chemical class 0.000 description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- GALAFVYMXSKXPQ-UHFFFAOYSA-N 1,2,3-tri(pentan-3-yl)cyclopenta-1,3-diene Chemical compound CCC(CC)C1=C(C(CC)CC)C(C(CC)CC)=CC1 GALAFVYMXSKXPQ-UHFFFAOYSA-N 0.000 description 2
- RIUMFBQICCDHFC-UHFFFAOYSA-N 1-pentylcyclopenta-1,3-diene Chemical compound CCCCCC1=CC=CC1 RIUMFBQICCDHFC-UHFFFAOYSA-N 0.000 description 2
- IWSZDQRGNFLMJS-UHFFFAOYSA-N 2-(dibutylamino)ethanol Chemical compound CCCCN(CCO)CCCC IWSZDQRGNFLMJS-UHFFFAOYSA-N 0.000 description 2
- KZPNEOVEXNXBTG-UHFFFAOYSA-N 2-[5,5-di(butan-2-yl)cyclopenta-1,3-dien-1-yl]-N,N-dimethylethanamine Chemical compound CN(C)CCC1=CC=CC1(C(C)CC)C(C)CC KZPNEOVEXNXBTG-UHFFFAOYSA-N 0.000 description 2
- SDLGQTZTCHJWOR-UHFFFAOYSA-N 2-[5,5-di(pentan-2-yl)cyclopenta-1,3-dien-1-yl]-N,N-dimethylethanamine Chemical compound CN(C)CCC1=CC=CC1(C(C)CCC)C(C)CCC SDLGQTZTCHJWOR-UHFFFAOYSA-N 0.000 description 2
- UPSXAPQYNGXVBF-UHFFFAOYSA-N 2-bromobutane Chemical compound CCC(C)Br UPSXAPQYNGXVBF-UHFFFAOYSA-N 0.000 description 2
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- HDLXPNDSLDLJHF-UHFFFAOYSA-N 4,7,13,16,21-pentaoxa-1,10-diazabicyclo[8.8.5]tricosane Chemical compound C1COCCOCCN2CCOCCOCCN1CCOCC2 HDLXPNDSLDLJHF-UHFFFAOYSA-N 0.000 description 2
- JNRQYICVSCTVKO-UHFFFAOYSA-N 5,5-bis(2-methylbutan-2-yl)cyclopenta-1,3-diene Chemical compound CC(CC)(C)C1(C=CC=C1)C(CC)(C)C JNRQYICVSCTVKO-UHFFFAOYSA-N 0.000 description 2
- VQTFNXZMXLUZQL-UHFFFAOYSA-N 5,5-bis(3-methylpentan-3-yl)cyclopenta-1,3-diene Chemical compound CC(CC)(CC)C1(C=CC=C1)C(CC)(C)CC VQTFNXZMXLUZQL-UHFFFAOYSA-N 0.000 description 2
- ZVDDKNWZQSDQNX-UHFFFAOYSA-N 5,5-di(propan-2-yl)cyclopenta-1,3-diene Chemical compound CC(C)C1(C(C)C)C=CC=C1 ZVDDKNWZQSDQNX-UHFFFAOYSA-N 0.000 description 2
- MXSFQYNTDPVTCD-UHFFFAOYSA-N 5-(2-chloroethyl)-1,2,3,4-tetramethylcyclopenta-1,3-diene Chemical compound CC1=C(C)C(C)=C(C)C1CCCl MXSFQYNTDPVTCD-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 239000002879 Lewis base Substances 0.000 description 2
- RQOMONYCWUPLLB-UHFFFAOYSA-N N-[2-[2-[2-(butylamino)ethyl]-3,3-di(pentan-2-yl)cyclopenta-1,4-dien-1-yl]ethyl]butan-1-amine Chemical compound C(CCC)NCCC1=C(C(C=C1)(C(C)CCC)C(C)CCC)CCNCCCC RQOMONYCWUPLLB-UHFFFAOYSA-N 0.000 description 2
- WVXFGYPKHNALEA-UHFFFAOYSA-N N-butyl-N-[2-[5,5-di(pentan-2-yl)cyclopenta-1,3-dien-1-yl]ethyl]butan-1-amine Chemical compound C(CCC)N(CCCC)CCC1=CC=CC1(C(C)CCC)C(C)CCC WVXFGYPKHNALEA-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
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- NIJQSFVWKGQGGJ-UHFFFAOYSA-N [Li].C1CCCCC1C1=C(C2CCCCC2)CC(CCN(C)C)=C1C1CCCCC1 Chemical compound [Li].C1CCCCC1C1=C(C2CCCCC2)CC(CCN(C)C)=C1C1CCCCC1 NIJQSFVWKGQGGJ-UHFFFAOYSA-N 0.000 description 1
- KUGGOUZULAFWGU-UHFFFAOYSA-N [dimethyl-(2,3,4,5-tetramethylcyclopenta-2,4-dien-1-yl)silyl]methyl-diphenylphosphane Chemical compound CC1=C(C)C(C)=C(C)C1[Si](C)(C)CP(C=1C=CC=CC=1)C1=CC=CC=C1 KUGGOUZULAFWGU-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000001118 alkylidene group Chemical group 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- VUEDNLCYHKSELL-UHFFFAOYSA-N arsonium Chemical compound [AsH4+] VUEDNLCYHKSELL-UHFFFAOYSA-N 0.000 description 1
- 150000004646 arylidenes Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229940090047 auto-injector Drugs 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 1
- JOZHCQBYRBGYAJ-UHFFFAOYSA-M benzyl(triphenyl)phosphanium;iodide Chemical compound [I-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)CC1=CC=CC=C1 JOZHCQBYRBGYAJ-UHFFFAOYSA-M 0.000 description 1
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 1
- YRPWLKVCRKAUAO-UHFFFAOYSA-N bismuthonium Chemical compound [BiH4+] YRPWLKVCRKAUAO-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 125000006309 butyl amino group Chemical group 0.000 description 1
- 230000006315 carbonylation Effects 0.000 description 1
- 238000005810 carbonylation reaction Methods 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005229 chemical vapour deposition Methods 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- ITKVLPYNJQOCPW-UHFFFAOYSA-N chloro-(chloromethyl)-dimethylsilane Chemical compound C[Si](C)(Cl)CCl ITKVLPYNJQOCPW-UHFFFAOYSA-N 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000003426 co-catalyst Substances 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- DMSZORWOGDLWGN-UHFFFAOYSA-N ctk1a3526 Chemical class NP(N)(N)=O DMSZORWOGDLWGN-UHFFFAOYSA-N 0.000 description 1
- AQHXALDLCNTRII-UHFFFAOYSA-N cyclopenta-1,3-dien-1-ylcyclohexane Chemical compound C1C=CC=C1C1CCCCC1 AQHXALDLCNTRII-UHFFFAOYSA-N 0.000 description 1
- 229960002887 deanol Drugs 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- HASCQPSFPAKVEK-UHFFFAOYSA-N dimethyl(phenyl)phosphine Chemical compound CP(C)C1=CC=CC=C1 HASCQPSFPAKVEK-UHFFFAOYSA-N 0.000 description 1
- YQOVJDHDCFIJRZ-UHFFFAOYSA-N dimethyl-[2-(2,3,4,5-tetramethylcyclopenta-2,4-dien-1-yl)ethyl]phosphane Chemical compound CP(C)CCC1C(C)=C(C)C(C)=C1C YQOVJDHDCFIJRZ-UHFFFAOYSA-N 0.000 description 1
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 description 1
- YOTZYFSGUCFUKA-UHFFFAOYSA-N dimethylphosphine Chemical compound CPC YOTZYFSGUCFUKA-UHFFFAOYSA-N 0.000 description 1
- SOACEOCCYCLKFA-UHFFFAOYSA-N diphenyl-[2-(2,3,4,5-tetramethylcyclopenta-2,4-dien-1-yl)ethyl]phosphane Chemical compound CC1=C(C)C(C)=C(C)C1CCP(C=1C=CC=CC=1)C1=CC=CC=C1 SOACEOCCYCLKFA-UHFFFAOYSA-N 0.000 description 1
- OBTIDFCSHQLONE-UHFFFAOYSA-N diphenylphosphane;lithium Chemical compound [Li].C=1C=CC=CC=1PC1=CC=CC=C1 OBTIDFCSHQLONE-UHFFFAOYSA-N 0.000 description 1
- WMFHTIJCSNSMDO-UHFFFAOYSA-N diphenylphosphinoethyl-pss Chemical group C=1C=CC=CC=1P(C=1C=CC=CC=1)CC[Si](O1)(O2)O[Si](O3)(C4CCCC4)O[Si](O4)(C5CCCC5)O[Si]1(C1CCCC1)O[Si](O1)(C5CCCC5)O[Si]2(C2CCCC2)O[Si]3(C2CCCC2)O[Si]41C1CCCC1 WMFHTIJCSNSMDO-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
- JHYNXXDQQHTCHJ-UHFFFAOYSA-M ethyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC)C1=CC=CC=C1 JHYNXXDQQHTCHJ-UHFFFAOYSA-M 0.000 description 1
- 230000003631 expected effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 description 1
- 238000004508 fractional distillation 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
- 229910052735 hafnium Inorganic materials 0.000 description 1
- XTJLXXCARCJVPJ-UHFFFAOYSA-N hepta-2,4-diene Chemical compound CCC=CC=CC XTJLXXCARCJVPJ-UHFFFAOYSA-N 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- QXLUTPDNMOEWGG-UHFFFAOYSA-N kryptand 222b Chemical compound C1COCCOCCN2CCOCCOCCN1CCOC1=CC=CC=C1OCC2 QXLUTPDNMOEWGG-UHFFFAOYSA-N 0.000 description 1
- 150000002642 lithium compounds Chemical class 0.000 description 1
- NVMMPHVQFFIBOS-UHFFFAOYSA-N lithium;dibutylazanide Chemical compound [Li+].CCCC[N-]CCCC NVMMPHVQFFIBOS-UHFFFAOYSA-N 0.000 description 1
- IUYHWZFSGMZEOG-UHFFFAOYSA-M magnesium;propane;chloride Chemical compound [Mg+2].[Cl-].C[CH-]C IUYHWZFSGMZEOG-UHFFFAOYSA-M 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005649 metathesis reaction Methods 0.000 description 1
- NCWQJOGVLLNWEO-UHFFFAOYSA-N methylsilicon Chemical compound [Si]C NCWQJOGVLLNWEO-UHFFFAOYSA-N 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- ANTXIWSXINVYEJ-UHFFFAOYSA-N n,n-dimethyl-2-(2,3,4-tricyclohexylcyclopenta-1,3-dien-1-yl)ethanamine Chemical compound C1CCCCC1C1=C(C2CCCCC2)CC(CCN(C)C)=C1C1CCCCC1 ANTXIWSXINVYEJ-UHFFFAOYSA-N 0.000 description 1
- HCIHUXZZMXOFDR-UHFFFAOYSA-N n,n-dimethyl-2-[2,3,4-tri(butan-2-yl)cyclopenta-1,3-dien-1-yl]ethanamine Chemical compound CCC(C)C1=C(C(C)CC)C(C(C)CC)=C(CCN(C)C)C1 HCIHUXZZMXOFDR-UHFFFAOYSA-N 0.000 description 1
- BREAHIDYHATNTE-UHFFFAOYSA-N n,n-dimethyl-2-[2,3,4-tri(pentan-2-yl)cyclopenta-1,3-dien-1-yl]ethanamine Chemical compound CCCC(C)C1=C(C(C)CCC)C(C(C)CCC)=C(CCN(C)C)C1 BREAHIDYHATNTE-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- SSDSCDGVMJFTEQ-UHFFFAOYSA-N octadecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SSDSCDGVMJFTEQ-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000002901 organomagnesium compounds Chemical class 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 125000004894 pentylamino group Chemical group C(CCCC)N* 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000012048 reactive intermediate Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000007152 ring opening metathesis polymerisation reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium group Chemical group [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 150000003461 sulfonyl halides Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 1
- IBWGNZVCJVLSHB-UHFFFAOYSA-M tetrabutylphosphanium;chloride Chemical compound [Cl-].CCCC[P+](CCCC)(CCCC)CCCC IBWGNZVCJVLSHB-UHFFFAOYSA-M 0.000 description 1
- WAGFXJQAIZNSEQ-UHFFFAOYSA-M tetraphenylphosphonium chloride Chemical compound [Cl-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 WAGFXJQAIZNSEQ-UHFFFAOYSA-M 0.000 description 1
- CMWCOKOTCLFJOP-UHFFFAOYSA-N titanium(3+) Chemical compound [Ti+3] CMWCOKOTCLFJOP-UHFFFAOYSA-N 0.000 description 1
- 125000005490 tosylate group Chemical group 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- RYVBINGWVJJDPU-UHFFFAOYSA-M tributyl(hexadecyl)phosphanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[P+](CCCC)(CCCC)CCCC RYVBINGWVJJDPU-UHFFFAOYSA-M 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
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- 229910052726 zirconium Inorganic materials 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
- C07F19/00—Metal compounds according to more than one of main groups C07F1/00 - C07F17/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F17/00—Metallocenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/25—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing rings other than six-membered aromatic 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
- C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/10—Systems containing only non-condensed rings with a five-membered ring the ring being unsaturated
-
- 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
- C08F4/619—Component covered by group C08F4/60 containing a transition metal-carbon bond
- C08F4/61908—Component covered by group C08F4/60 containing a transition metal-carbon bond in combination with an ionising compound other than alumoxane, e.g. (C6F5)4B-X+
-
- 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
- C08F4/619—Component covered by group C08F4/60 containing a transition metal-carbon bond
- C08F4/61912—Component covered by group C08F4/60 containing a transition metal-carbon bond in combination with an organoaluminium compound
-
- 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
- C08F4/619—Component covered by group C08F4/60 containing a transition metal-carbon bond
- C08F4/6192—Component covered by group C08F4/60 containing a transition metal-carbon bond containing at least one cyclopentadienyl ring, condensed or not, e.g. an indenyl or a fluorenyl ring
-
- 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)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Polymerization Catalysts (AREA)
- Catalysts (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Saccharide Compounds (AREA)
- Liquid Crystal Substances (AREA)
- Luminescent Compositions (AREA)
Priority Applications (16)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL1003008A NL1003008C2 (nl) | 1996-05-03 | 1996-05-03 | Met een heteroatoom-bevattende groep gesubstitueerde cyclopentadieen- verbinding. |
| TW086104448A TW376387B (en) | 1996-05-03 | 1997-04-08 | Cyclopentadiene compound substituted with a hetero atom-containing group |
| SG1997001283A SG74009A1 (en) | 1996-05-03 | 1997-04-23 | Cyclopentadiene compound substituted with a hetero atom-containing group |
| JP9142874A JPH10101607A (ja) | 1996-05-03 | 1997-04-25 | ヘテロ原子含有基により置換されているシクロペンタジエン化合物 |
| EP97201270A EP0805142B1 (de) | 1996-05-03 | 1997-04-28 | Mit einer ein Hetero-Atom enthaltenden Gruppe substituierte Cyclopentadien-Verbindung |
| AT97201270T ATE178045T1 (de) | 1996-05-03 | 1997-04-28 | Mit einer ein hetero-atom enthaltenden gruppe substituierte cyclopentadien-verbindung |
| DE69700153T DE69700153T2 (de) | 1996-05-03 | 1997-04-28 | Mit einer ein Hetero-Atom enthaltenden Gruppe substituierte Cyclopentadien-Verbindung |
| ES97201270T ES2130865T3 (es) | 1996-05-03 | 1997-04-28 | Compuesto de ciclopentadieno sustituido con un grupo que contiene un heteroatomo. |
| EA199700048A EA199700048A1 (ru) | 1996-05-03 | 1997-04-29 | Циклопентадиеновые соединения, замещенные группой, содержащей гетероатом |
| CN97109764A CN1166483A (zh) | 1996-05-03 | 1997-04-30 | 用含杂原子基团取代的环戊二烯化合物 |
| NO972020A NO972020L (no) | 1996-05-03 | 1997-04-30 | Syklopentadienforbindelse substituert med en heteroatominneholdende gruppe |
| CA002204203A CA2204203A1 (en) | 1996-05-03 | 1997-05-01 | Cyclopentadiene compound substituted with a hetero atom-containing group |
| IDP971470A ID17185A (id) | 1996-05-03 | 1997-05-02 | Senyawa siklopentadiena yang tersubstitusi oleh gugus yang mengandung atom hetero |
| MXPA/A/1997/003313A MXPA97003313A (en) | 1996-05-03 | 1997-05-02 | Composite of cyclopentadiene replaced with a group containing heteroato |
| US08/850,274 US6072067A (en) | 1996-05-03 | 1997-05-02 | Cyclopentadiene compound substituted with a hetero atom-containing group |
| KR1019970017569A KR970074788A (ko) | 1996-05-03 | 1997-05-03 | 헤테로 원자-함유 그룹으로 치환된 시클로펜타디엔 화합물 |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL1003008 | 1996-05-03 | ||
| NL1003008A NL1003008C2 (nl) | 1996-05-03 | 1996-05-03 | Met een heteroatoom-bevattende groep gesubstitueerde cyclopentadieen- verbinding. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL1003008C2 true NL1003008C2 (nl) | 1997-11-06 |
Family
ID=19762779
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL1003008A NL1003008C2 (nl) | 1996-05-03 | 1996-05-03 | Met een heteroatoom-bevattende groep gesubstitueerde cyclopentadieen- verbinding. |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US6072067A (de) |
| EP (1) | EP0805142B1 (de) |
| JP (1) | JPH10101607A (de) |
| KR (1) | KR970074788A (de) |
| CN (1) | CN1166483A (de) |
| AT (1) | ATE178045T1 (de) |
| CA (1) | CA2204203A1 (de) |
| DE (1) | DE69700153T2 (de) |
| EA (1) | EA199700048A1 (de) |
| ES (1) | ES2130865T3 (de) |
| ID (1) | ID17185A (de) |
| NL (1) | NL1003008C2 (de) |
| NO (1) | NO972020L (de) |
| SG (1) | SG74009A1 (de) |
| TW (1) | TW376387B (de) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2231013A1 (en) * | 1997-04-30 | 1998-10-30 | Eli Lilly And Company | Process for preparing benzoic acid derivative intermediates and benzothiophene pharmaceuticals |
| US6489261B1 (en) * | 1997-12-01 | 2002-12-03 | Dsm N.V. | Catalyst composition comprising a reduced transition metal complex and a cocatalyst |
| BR9908887A (pt) | 1998-05-01 | 2000-11-21 | Exxon Chemical Patents Inc | Complexos catalìticos de metal contendo ligando tridentado para polimerização de olefina |
| US6723675B1 (en) | 2000-05-25 | 2004-04-20 | Univation Technologies, Llc | Catalyst for the production of olefin polymers |
| US7078164B1 (en) | 2000-06-19 | 2006-07-18 | Symyx Technologies, Inc. | High throughput screen for identifying polymerization catalysts from potential catalysts |
| US6909009B2 (en) * | 2001-03-08 | 2005-06-21 | Avtandil Koridze | Alkane and alkane group dehydrogenation with organometallic catalysts |
| CA2446116A1 (en) * | 2001-05-14 | 2002-11-21 | Dow Global Technologies Inc. | 3-aryl-substituted cyclopentadienyl metal complexes and polymerization process |
| DE102004061618A1 (de) * | 2004-12-17 | 2006-06-22 | Basell Polyolefine Gmbh | Monocyclopentadienylkomplexe |
| EP2691443B1 (de) | 2011-03-28 | 2021-02-17 | Massachusetts Institute of Technology | Konjugierte lipomers und ihre verwendung |
| EA032088B1 (ru) * | 2011-10-27 | 2019-04-30 | Массачусетс Инститьют Оф Текнолоджи | Аминокислотные производные, функционализованные на n-конце, способные образовывать микросферы, инкапсулирующие лекарственное средство |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0416815A2 (de) * | 1989-08-31 | 1991-03-13 | The Dow Chemical Company | Additionspolymerisationskatalysatoren mit eingeschränkter Geometrie, Verfahren zur Herstellung davon, VorlÀ¤ufer dafür, Verfahren zur Verwendung und daraus hergestellte Polymere |
| DE4303647A1 (de) * | 1993-02-09 | 1994-08-11 | Basf Ag | Cyclopentadiene mit funktionalisierter Kohlenwasserstoff-Seitenkette |
| JPH06279478A (ja) * | 1993-03-24 | 1994-10-04 | Mitsui Petrochem Ind Ltd | シクロペンタジエニル基含有ケイ素化合物またはシクロペンタジエニル基含有ゲルマニウム化合物の製造方法 |
| WO1996013529A1 (en) * | 1994-10-31 | 1996-05-09 | Dsm N.V. | Catalyst composition and process for the polymerization of an olefin |
| EP0728770A1 (de) * | 1995-02-21 | 1996-08-28 | Montell North America Inc. | Verfahren zur Herstellung von festen Katalysatorkomponenten für die Olefinpolymerisation |
| EP0728769A1 (de) * | 1995-02-21 | 1996-08-28 | Montell North America Inc. | Komponente und Katalysatore für die Olefinpolymerisation |
| EP0728724A1 (de) * | 1995-02-21 | 1996-08-28 | Montell North America Inc. | Bei der Herstellung von Ziegler-Natta-Katalysatoren verwendbare Diether |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5563284A (en) * | 1994-09-09 | 1996-10-08 | Phillips Petroleum Company | Cyclopentadienyl-type ligands, metallocenes, catalyst systems, preparation, and use |
| NL1003007C2 (nl) * | 1996-05-03 | 1997-11-06 | Dsm Nv | Met vertakte alkylgroepen gesubstitueerde cyclopentadieenverbinding. |
| NL1003021C2 (nl) * | 1996-05-03 | 1997-11-06 | Dsm Nv | Meervoudig gesubstitueerd cyclopentadieen. |
| NL1003000C2 (nl) * | 1996-05-03 | 1997-11-06 | Dsm Nv | Synthese van een amine-bevattend cyclopentadieen. |
| NL1003012C2 (nl) * | 1996-05-03 | 1997-11-06 | Dsm Nv | Met aralkylgroepen gesubstitueerde cyclopentadieenverbinding. |
| NL1003013C2 (nl) * | 1996-05-03 | 1997-11-06 | Dsm Nv | Met cyclische groepen gesubstitueerde cyclopentadieenverbinding. |
| NL1003006C2 (nl) * | 1996-05-03 | 1997-11-06 | Dsm Nv | Met vertakte alkylgroepen gesubstitueerde cyclopentadieenverbinding. |
| NL1003014C2 (nl) * | 1996-05-03 | 1997-11-06 | Dsm Nv | Met tertiaire groepen gesubstitueerde cyclopentadieenverbinding. |
| NL1003019C2 (nl) * | 1996-05-03 | 1997-11-06 | Dsm Nv | Meervoudig gesubstitueerd cyclopentadieen. |
| NL1003004C2 (nl) * | 1996-05-03 | 1997-11-06 | Dsm Nv | Met onderling verschillende groepen gesubstitueerde cyclopentadieen- verbinding. |
| NL1003011C2 (nl) * | 1996-05-03 | 1997-11-06 | Dsm Nv | Met een heteroatoom bevattende groep gesubstitueerde cyclopentadieen- verbinding. |
| NL1003005C2 (nl) * | 1996-05-03 | 1997-11-06 | Dsm Nv | Met lineaire groepen gesubstitueerde cyclopentadieenverbinding. |
| NL1003015C2 (nl) * | 1996-05-03 | 1997-11-06 | Dsm Nv | Met chirale groepen gesubstitueerde cyclopentadieenverbinding. |
-
1996
- 1996-05-03 NL NL1003008A patent/NL1003008C2/nl not_active IP Right Cessation
-
1997
- 1997-04-08 TW TW086104448A patent/TW376387B/zh active
- 1997-04-23 SG SG1997001283A patent/SG74009A1/en unknown
- 1997-04-25 JP JP9142874A patent/JPH10101607A/ja active Pending
- 1997-04-28 EP EP97201270A patent/EP0805142B1/de not_active Revoked
- 1997-04-28 ES ES97201270T patent/ES2130865T3/es not_active Expired - Lifetime
- 1997-04-28 DE DE69700153T patent/DE69700153T2/de not_active Revoked
- 1997-04-28 AT AT97201270T patent/ATE178045T1/de not_active IP Right Cessation
- 1997-04-29 EA EA199700048A patent/EA199700048A1/ru unknown
- 1997-04-30 NO NO972020A patent/NO972020L/no unknown
- 1997-04-30 CN CN97109764A patent/CN1166483A/zh active Pending
- 1997-05-01 CA CA002204203A patent/CA2204203A1/en not_active Abandoned
- 1997-05-02 ID IDP971470A patent/ID17185A/id unknown
- 1997-05-02 US US08/850,274 patent/US6072067A/en not_active Expired - Fee Related
- 1997-05-03 KR KR1019970017569A patent/KR970074788A/ko not_active Withdrawn
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| EP0416815A2 (de) * | 1989-08-31 | 1991-03-13 | The Dow Chemical Company | Additionspolymerisationskatalysatoren mit eingeschränkter Geometrie, Verfahren zur Herstellung davon, VorlÀ¤ufer dafür, Verfahren zur Verwendung und daraus hergestellte Polymere |
| DE4303647A1 (de) * | 1993-02-09 | 1994-08-11 | Basf Ag | Cyclopentadiene mit funktionalisierter Kohlenwasserstoff-Seitenkette |
| JPH06279478A (ja) * | 1993-03-24 | 1994-10-04 | Mitsui Petrochem Ind Ltd | シクロペンタジエニル基含有ケイ素化合物またはシクロペンタジエニル基含有ゲルマニウム化合物の製造方法 |
| WO1996013529A1 (en) * | 1994-10-31 | 1996-05-09 | Dsm N.V. | Catalyst composition and process for the polymerization of an olefin |
| EP0728770A1 (de) * | 1995-02-21 | 1996-08-28 | Montell North America Inc. | Verfahren zur Herstellung von festen Katalysatorkomponenten für die Olefinpolymerisation |
| EP0728769A1 (de) * | 1995-02-21 | 1996-08-28 | Montell North America Inc. | Komponente und Katalysatore für die Olefinpolymerisation |
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| CHEMICAL ABSTRACTS, vol. 123, no. 13, 25 September 1995, Columbus, Ohio, US; abstract no. 169881, KISO, YOSHIHISA ET AL: "Preparation of cyclopentadienylsilicon or -germanium compounds" XP002020388 * |
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Also Published As
| Publication number | Publication date |
|---|---|
| EP0805142B1 (de) | 1999-03-24 |
| EA199700048A1 (ru) | 1997-12-30 |
| KR970074788A (ko) | 1997-12-10 |
| ES2130865T3 (es) | 1999-07-01 |
| DE69700153D1 (de) | 1999-04-29 |
| NO972020L (no) | 1997-11-04 |
| NO972020D0 (no) | 1997-04-30 |
| CN1166483A (zh) | 1997-12-03 |
| ID17185A (id) | 1997-12-04 |
| ATE178045T1 (de) | 1999-04-15 |
| EP0805142A1 (de) | 1997-11-05 |
| CA2204203A1 (en) | 1997-11-03 |
| JPH10101607A (ja) | 1998-04-21 |
| MX9703313A (es) | 1998-05-31 |
| US6072067A (en) | 2000-06-06 |
| TW376387B (en) | 1999-12-11 |
| DE69700153T2 (de) | 1999-11-25 |
| SG74009A1 (en) | 2000-07-18 |
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| PD2B | A search report has been drawn up | ||
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