NL1003010C2 - Werkwijze voor het omzetten van een geminaal gesubstitueerd cyclopentadieen. - Google Patents

Werkwijze voor het omzetten van een geminaal gesubstitueerd cyclopentadieen. Download PDF

Info

Publication number: NL1003010C2
Authority: NL; Netherlands
Prior art keywords: cyclopentadiene; substituents; substituent; geminally substituted; mixture
Prior art date: 1996-05-03

Application number

NL1003010A

Other languages

English (en)

Dutch (nl)

Inventor

Gerardus Johannes Maria Gruter

Johannus Antonius Maria V Beek

Original Assignee

Dsm Nv

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1996-05-03

Filing date

1996-05-03

Publication date

1997-11-06

1996-05-03 Application filed by Dsm Nv filed Critical Dsm Nv

1996-05-03 Priority to NL1003010A priority Critical patent/NL1003010C2/nl

1997-04-25 Priority to JP9539779A priority patent/JP2000509710A/ja

1997-04-25 Priority to PCT/NL1997/000225 priority patent/WO1997042145A1/en

1997-04-25 Priority to AU24102/97A priority patent/AU2410297A/en

1997-04-25 Priority to EP97919745A priority patent/EP0897379B1/de

1997-04-25 Priority to DE69707857T priority patent/DE69707857T2/de

1997-04-25 Priority to US09/180,179 priority patent/US6137019A/en

1997-11-06 Application granted granted Critical

1997-11-06 Publication of NL1003010C2 publication Critical patent/NL1003010C2/nl

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

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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)

NL1003010A 1996-05-03 1996-05-03 Werkwijze voor het omzetten van een geminaal gesubstitueerd cyclopentadieen. NL1003010C2 (nl)

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)

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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

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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)

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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

Legal Events

Date	Code	Title	Description
1998-01-05	PD2B	A search report has been drawn up
2001-02-01	VD1	Lapsed due to non-payment of the annual fee	Effective date: 20001201

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