NL1003010C2 - Werkwijze voor het omzetten van een geminaal gesubstitueerd cyclopentadieen. - Google Patents
Werkwijze voor het omzetten van een geminaal gesubstitueerd cyclopentadieen. Download PDFInfo
- Publication number
- NL1003010C2 NL1003010C2 NL1003010A NL1003010A NL1003010C2 NL 1003010 C2 NL1003010 C2 NL 1003010C2 NL 1003010 A NL1003010 A NL 1003010A NL 1003010 A NL1003010 A NL 1003010A NL 1003010 C2 NL1003010 C2 NL 1003010C2
- Authority
- NL
- Netherlands
- Prior art keywords
- cyclopentadiene
- substituents
- substituent
- geminally substituted
- mixture
- Prior art date
Links
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical class C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 title claims description 82
- 238000000034 method Methods 0.000 title claims description 13
- 125000001424 substituent group Chemical group 0.000 claims description 43
- 239000000203 mixture Substances 0.000 claims description 33
- 229910052700 potassium Inorganic materials 0.000 claims description 20
- 239000011591 potassium Substances 0.000 claims description 19
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 239000011734 sodium Substances 0.000 claims description 10
- 229910052708 sodium Inorganic materials 0.000 claims description 10
- 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 claims description 9
- 239000002585 base Substances 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 8
- 239000003446 ligand Substances 0.000 claims description 8
- 238000006467 substitution reaction Methods 0.000 claims description 7
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- 238000003786 synthesis reaction Methods 0.000 claims description 5
- 229920000098 polyolefin Polymers 0.000 claims description 4
- 229910052723 transition metal Inorganic materials 0.000 claims description 2
- 150000003624 transition metals Chemical class 0.000 claims description 2
- 230000000153 supplemental effect Effects 0.000 claims 2
- 101150104316 Dnase2b gene Proteins 0.000 claims 1
- 230000008774 maternal effect Effects 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 12
- -1 aromatic anion Chemical class 0.000 description 12
- 229910052799 carbon Inorganic materials 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 125000005842 heteroatom Chemical group 0.000 description 8
- 238000006116 polymerization reaction Methods 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000000243 solution Substances 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 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 230000000737 periodic effect Effects 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- MBRJEKTWCTVQKS-UHFFFAOYSA-N 1,2,3,4-tetraethylcyclopenta-1,3-diene Chemical compound CCC1=C(CC)C(CC)=C(CC)C1 MBRJEKTWCTVQKS-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- NAMYKGVDVNBCFQ-UHFFFAOYSA-N 2-bromopropane Chemical compound CC(C)Br NAMYKGVDVNBCFQ-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 4
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 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 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 238000010348 incorporation Methods 0.000 description 3
- 239000012968 metallocene catalyst Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 238000004611 spectroscopical analysis Methods 0.000 description 3
- 238000010626 work up procedure Methods 0.000 description 3
- ZUHBHGRZDBTBMA-UHFFFAOYSA-N 1,2,3-triethylcyclopenta-1,3-diene Chemical compound CCC1=C(CC)C(CC)=CC1 ZUHBHGRZDBTBMA-UHFFFAOYSA-N 0.000 description 2
- 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 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
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 238000012662 bulk polymerization Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 2
- 229910000105 potassium hydride Inorganic materials 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- LWNGJAHMBMVCJR-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenoxy)boronic acid Chemical compound OB(O)OC1=C(F)C(F)=C(F)C(F)=C1F LWNGJAHMBMVCJR-UHFFFAOYSA-N 0.000 description 1
- AGWRAAIQXVWVLJ-UHFFFAOYSA-N 1,2,3,4,5-pentaethylcyclopenta-1,3-diene Chemical compound CCC1C(CC)=C(CC)C(CC)=C1CC AGWRAAIQXVWVLJ-UHFFFAOYSA-N 0.000 description 1
- AKQMNIHRKQTBCG-UHFFFAOYSA-N 1,2,3,4-tetra(propan-2-yl)cyclopenta-1,3-diene Chemical compound CC(C)C1=C(C(C)C)C(C(C)C)=C(C(C)C)C1 AKQMNIHRKQTBCG-UHFFFAOYSA-N 0.000 description 1
- XFBGLGPKGWWSCJ-UHFFFAOYSA-N 1,3,5,5-tetraethylcyclopenta-1,3-diene Chemical compound CCC1=CC(CC)(CC)C(CC)=C1 XFBGLGPKGWWSCJ-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 1
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 1
- MWQKURVBJZAOSC-UHFFFAOYSA-N 1-propan-2-ylcyclopenta-1,3-diene Chemical compound CC(C)C1=CC=CC1 MWQKURVBJZAOSC-UHFFFAOYSA-N 0.000 description 1
- PIJIRCVOFHURLX-UHFFFAOYSA-N 2,5,5-tri(propan-2-yl)cyclopenta-1,3-diene Chemical compound CC(C)C1=CC(C(C)C)(C(C)C)C=C1 PIJIRCVOFHURLX-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- 229910004809 Na2 SO4 Inorganic materials 0.000 description 1
- 229910000574 NaK Inorganic materials 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 125000001118 alkylidene group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 150000004646 arylidenes 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
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000002902 bimodal effect Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000005229 chemical vapour deposition Methods 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 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 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
- 230000005595 deprotonation Effects 0.000 description 1
- 238000010537 deprotonation reaction Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography 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
- 150000004820 halides Chemical group 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 229910052744 lithium Inorganic materials 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
- 150000002739 metals Chemical class 0.000 description 1
- NCWQJOGVLLNWEO-UHFFFAOYSA-N methylsilicon Chemical compound [Si]C NCWQJOGVLLNWEO-UHFFFAOYSA-N 0.000 description 1
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 1
- 239000000178 monomer Substances 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
- 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
- 239000012044 organic layer Substances 0.000 description 1
- 150000002900 organolithium compounds 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
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000012048 reactive intermediate Substances 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- ANEFWEBMQHRDLH-UHFFFAOYSA-N tris(2,3,4,5,6-pentafluorophenyl) borate Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1OB(OC=1C(=C(F)C(F)=C(F)C=1F)F)OC1=C(F)C(F)=C(F)C(F)=C1F ANEFWEBMQHRDLH-UHFFFAOYSA-N 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2282—Unsaturated compounds used as ligands
- B01J31/2295—Cyclic compounds, e.g. cyclopentadienyls
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C4/00—Preparation of hydrocarbons from hydrocarbons containing a larger number of carbon atoms
- C07C4/08—Preparation of hydrocarbons from hydrocarbons containing a larger number of carbon atoms by splitting-off an aliphatic or cycloaliphatic part from the molecule
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/30—Complexes comprising metals of Group III (IIIA or IIIB) as the central metal
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/40—Complexes comprising metals of Group IV (IVA or IVB) as the central metal
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/50—Complexes comprising metals of Group V (VA or VB) as the central metal
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/60—Complexes comprising metals of Group VI (VIA or VIB) as the central metal
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/70—Complexes comprising metals of Group VII (VIIB) as the central metal
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Inorganic Chemistry (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL1003010A NL1003010C2 (nl) | 1996-05-03 | 1996-05-03 | Werkwijze voor het omzetten van een geminaal gesubstitueerd cyclopentadieen. |
| JP9539779A JP2000509710A (ja) | 1996-05-03 | 1997-04-25 | ジェミナルに置換されたシクロペンタジエンを転化する方法 |
| PCT/NL1997/000225 WO1997042145A1 (en) | 1996-05-03 | 1997-04-25 | Process for converting a geminally substituted cyclopentadiene |
| AU24102/97A AU2410297A (en) | 1996-05-03 | 1997-04-25 | Process for converting a geminally substituted cyclopentadiene |
| EP97919745A EP0897379B1 (de) | 1996-05-03 | 1997-04-25 | Verfahren zur umwandlung eines geminal substituierten cyclopentadiens |
| DE69707857T DE69707857T2 (de) | 1996-05-03 | 1997-04-25 | Verfahren zur umwandlung eines geminal substituierten cyclopentadiens |
| US09/180,179 US6137019A (en) | 1996-05-03 | 1997-04-25 | Process for converting a geminally substituted cyclopentadiene |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL1003010A NL1003010C2 (nl) | 1996-05-03 | 1996-05-03 | Werkwijze voor het omzetten van een geminaal gesubstitueerd cyclopentadieen. |
| NL1003010 | 1996-05-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL1003010C2 true NL1003010C2 (nl) | 1997-11-06 |
Family
ID=19762781
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL1003010A NL1003010C2 (nl) | 1996-05-03 | 1996-05-03 | Werkwijze voor het omzetten van een geminaal gesubstitueerd cyclopentadieen. |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US6137019A (de) |
| EP (1) | EP0897379B1 (de) |
| JP (1) | JP2000509710A (de) |
| AU (1) | AU2410297A (de) |
| DE (1) | DE69707857T2 (de) |
| NL (1) | NL1003010C2 (de) |
| WO (1) | WO1997042145A1 (de) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2253502A1 (en) * | 1996-05-06 | 1997-11-13 | Stephen Warren Kaldor | Anti-viral compounds |
| JP2000511514A (ja) | 1996-05-06 | 2000-09-05 | イーライ・リリー・アンド・カンパニー | 抗ウイルス化合物 |
| US6156924A (en) * | 1996-05-06 | 2000-12-05 | Eli Lilly And Company | Anti-viral compounds |
| JP2000511886A (ja) * | 1996-05-06 | 2000-09-12 | イーライ・リリー・アンド・カンパニー | 抗ウイルス方法 |
| US6127422A (en) * | 1996-05-06 | 2000-10-03 | Eli Lilly And Company | Anti-viral method |
| US6103923A (en) * | 1996-05-06 | 2000-08-15 | Eli Lilly And Company | Anti-viral compounds |
| EP0811599B1 (de) | 1996-05-06 | 2001-03-07 | Eli Lilly And Company | Antivirusverbindungen |
| CA2253405A1 (en) * | 1996-05-06 | 1997-11-13 | William Joseph Hornback | Anti-viral compounds |
| US6096917A (en) * | 1997-05-02 | 2000-08-01 | Eli Lilly And Company | Anti-viral compounds |
| US6175034B1 (en) | 2000-04-10 | 2001-01-16 | Eli Lilly And Company | Anti-viral compounds |
| US10343193B2 (en) | 2014-02-24 | 2019-07-09 | The Boeing Company | System and method for surface cleaning |
| CN110183399A (zh) * | 2019-06-05 | 2019-08-30 | 辽宁科隆精细化工股份有限公司 | 一种合成4-(2-(n,n-二甲氨基)乙基)吗啉的方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5648578A (en) * | 1995-04-26 | 1997-07-15 | Albemarle Corporation | Preparation of polyalkylated cyclopentadienes from isobornyl carboxylates |
-
1996
- 1996-05-03 NL NL1003010A patent/NL1003010C2/nl not_active IP Right Cessation
-
1997
- 1997-04-25 EP EP97919745A patent/EP0897379B1/de not_active Expired - Lifetime
- 1997-04-25 US US09/180,179 patent/US6137019A/en not_active Expired - Fee Related
- 1997-04-25 DE DE69707857T patent/DE69707857T2/de not_active Expired - Fee Related
- 1997-04-25 WO PCT/NL1997/000225 patent/WO1997042145A1/en not_active Ceased
- 1997-04-25 JP JP9539779A patent/JP2000509710A/ja not_active Withdrawn
- 1997-04-25 AU AU24102/97A patent/AU2410297A/en not_active Abandoned
Non-Patent Citations (1)
| Title |
|---|
| PETER JUTZI ET AL.: "Dimethylaminoalkyl and Methoxyalkyl Substituted Tetramethylcyclopentadienes: Synthesis of Novel Polydentate Ligands", SYNTHESIS, no. 7, July 1993 (1993-07-01), STUTTGART DE, pages 684 - 686, XP000601948 * |
Also Published As
| Publication number | Publication date |
|---|---|
| US6137019A (en) | 2000-10-24 |
| AU2410297A (en) | 1997-11-26 |
| DE69707857T2 (de) | 2002-05-02 |
| EP0897379B1 (de) | 2001-10-31 |
| DE69707857D1 (de) | 2001-12-06 |
| EP0897379A1 (de) | 1999-02-24 |
| JP2000509710A (ja) | 2000-08-02 |
| WO1997042145A1 (en) | 1997-11-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PD2B | A search report has been drawn up | ||
| VD1 | Lapsed due to non-payment of the annual fee |
Effective date: 20001201 |