HRP20211805T1 - Postupak dimerizacije etilena - Google Patents
Postupak dimerizacije etilena Download PDFInfo
- Publication number
- HRP20211805T1 HRP20211805T1 HRP20211805TT HRP20211805T HRP20211805T1 HR P20211805 T1 HRP20211805 T1 HR P20211805T1 HR P20211805T T HRP20211805T T HR P20211805TT HR P20211805 T HRP20211805 T HR P20211805T HR P20211805 T1 HRP20211805 T1 HR P20211805T1
- Authority
- HR
- Croatia
- Prior art keywords
- nickel
- chloride
- allylnickal
- phosphine ligand
- methoxyphenyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 14
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 title claims 3
- 239000005977 Ethylene Substances 0.000 title claims 3
- 238000006471 dimerization reaction Methods 0.000 title claims 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims 16
- -1 brominated hydrocarbyl aluminum compounds Chemical class 0.000 claims 16
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims 10
- 239000003446 ligand Substances 0.000 claims 8
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims 8
- 239000000203 mixture Substances 0.000 claims 6
- 229910052759 nickel Inorganic materials 0.000 claims 5
- 239000002243 precursor Substances 0.000 claims 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims 2
- CMAOLVNGLTWICC-UHFFFAOYSA-N 2-fluoro-5-methylbenzonitrile Chemical compound CC1=CC=C(F)C(C#N)=C1 CMAOLVNGLTWICC-UHFFFAOYSA-N 0.000 claims 2
- NMVXHZSPDTXJSJ-UHFFFAOYSA-L 2-methylpropylaluminum(2+);dichloride Chemical compound CC(C)C[Al](Cl)Cl NMVXHZSPDTXJSJ-UHFFFAOYSA-L 0.000 claims 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 2
- 239000002879 Lewis base Substances 0.000 claims 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims 2
- 229910021586 Nickel(II) chloride Inorganic materials 0.000 claims 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 230000003213 activating effect Effects 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- HQMRIBYCTLBDAK-UHFFFAOYSA-M bis(2-methylpropyl)alumanylium;chloride Chemical compound CC(C)C[Al](Cl)CC(C)C HQMRIBYCTLBDAK-UHFFFAOYSA-M 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 150000001805 chlorine compounds Chemical class 0.000 claims 2
- 125000004122 cyclic group Chemical group 0.000 claims 2
- YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 claims 2
- UAIZDWNSWGTKFZ-UHFFFAOYSA-L ethylaluminum(2+);dichloride Chemical compound CC[Al](Cl)Cl UAIZDWNSWGTKFZ-UHFFFAOYSA-L 0.000 claims 2
- 150000007527 lewis bases Chemical class 0.000 claims 2
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 claims 2
- LGQLOGILCSXPEA-UHFFFAOYSA-L nickel sulfate Chemical compound [Ni+2].[O-]S([O-])(=O)=O LGQLOGILCSXPEA-UHFFFAOYSA-L 0.000 claims 2
- UNMGLSGVXHBBPH-BVHINDLDSA-L nickel(2+) (NE)-N-[(3E)-3-oxidoiminobutan-2-ylidene]hydroxylamine Chemical compound [Ni++].C\C(=N/O)\C(\C)=N\[O-].C\C(=N/O)\C(\C)=N\[O-] UNMGLSGVXHBBPH-BVHINDLDSA-L 0.000 claims 2
- DOLZKNFSRCEOFV-UHFFFAOYSA-L nickel(2+);oxalate Chemical compound [Ni+2].[O-]C(=O)C([O-])=O DOLZKNFSRCEOFV-UHFFFAOYSA-L 0.000 claims 2
- 229910000008 nickel(II) carbonate Inorganic materials 0.000 claims 2
- 229910021508 nickel(II) hydroxide Inorganic materials 0.000 claims 2
- 229910000363 nickel(II) sulfate Inorganic materials 0.000 claims 2
- ZULUUIKRFGGGTL-UHFFFAOYSA-L nickel(ii) carbonate Chemical compound [Ni+2].[O-]C([O-])=O ZULUUIKRFGGGTL-UHFFFAOYSA-L 0.000 claims 2
- BFDHFSHZJLFAMC-UHFFFAOYSA-L nickel(ii) hydroxide Chemical compound [OH-].[OH-].[Ni+2] BFDHFSHZJLFAMC-UHFFFAOYSA-L 0.000 claims 2
- VHSVJTYBTJCDFL-UHFFFAOYSA-L 1,2-dimethoxyethane;nickel(2+);dibromide Chemical compound Br[Ni]Br.COCCOC VHSVJTYBTJCDFL-UHFFFAOYSA-L 0.000 claims 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- OZHLXQFAHIYYDJ-UHFFFAOYSA-L 2-hydroxyacetate;nickel(2+) Chemical compound [Ni+2].OCC([O-])=O.OCC([O-])=O OZHLXQFAHIYYDJ-UHFFFAOYSA-L 0.000 claims 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 1
- UQRONKZLYKUEMO-UHFFFAOYSA-N 4-methyl-1-(2,4,6-trimethylphenyl)pent-4-en-2-one Chemical group CC(=C)CC(=O)Cc1c(C)cc(C)cc1C UQRONKZLYKUEMO-UHFFFAOYSA-N 0.000 claims 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims 1
- AEMRFAOFKBGASW-UHFFFAOYSA-M Glycolate Chemical compound OCC([O-])=O AEMRFAOFKBGASW-UHFFFAOYSA-M 0.000 claims 1
- VEQPNABPJHWNSG-UHFFFAOYSA-N Nickel(2+) Chemical compound [Ni+2] VEQPNABPJHWNSG-UHFFFAOYSA-N 0.000 claims 1
- 229910021585 Nickel(II) bromide Inorganic materials 0.000 claims 1
- 229910021587 Nickel(II) fluoride Inorganic materials 0.000 claims 1
- 229910021588 Nickel(II) iodide Inorganic materials 0.000 claims 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 1
- 239000012190 activator Substances 0.000 claims 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- YSTQWZZQKCCBAY-UHFFFAOYSA-L methylaluminum(2+);dichloride Chemical compound C[Al](Cl)Cl YSTQWZZQKCCBAY-UHFFFAOYSA-L 0.000 claims 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- IPLJNQFXJUCRNH-UHFFFAOYSA-L nickel(2+);dibromide Chemical compound [Ni+2].[Br-].[Br-] IPLJNQFXJUCRNH-UHFFFAOYSA-L 0.000 claims 1
- DBJLJFTWODWSOF-UHFFFAOYSA-L nickel(ii) fluoride Chemical compound F[Ni]F DBJLJFTWODWSOF-UHFFFAOYSA-L 0.000 claims 1
- BFSQJYRFLQUZKX-UHFFFAOYSA-L nickel(ii) iodide Chemical compound I[Ni]I BFSQJYRFLQUZKX-UHFFFAOYSA-L 0.000 claims 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/02—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons
- C07C2/04—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation
- C07C2/06—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation of alkenes, i.e. acyclic hydrocarbons having only one carbon-to-carbon double bond
- C07C2/08—Catalytic processes
- C07C2/26—Catalytic processes with hydrides or organic compounds
- C07C2/36—Catalytic processes with hydrides or organic compounds as phosphines, arsines, stilbines or bismuthines
-
- 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
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
- B01J31/14—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides of aluminium or boron
- B01J31/143—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides of aluminium or boron of aluminium
-
- 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
- B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
-
- 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
- B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
- B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
-
- 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
- B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
- B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
- B01J31/2409—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring with more than one complexing phosphine-P atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C11/00—Aliphatic unsaturated hydrocarbons
- C07C11/02—Alkenes
- C07C11/08—Alkenes with four carbon atoms
-
- 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
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/20—Olefin oligomerisation or telomerisation
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- 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
- B01J2531/84—Metals of the iron group
- B01J2531/847—Nickel
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- C07C2531/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
- C07C2531/14—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides of aluminium or boron
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- C07C2531/20—Carbonyls
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- C07C2531/24—Phosphines
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- 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
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- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Claims (12)
1. Postupak za dimerizaciju etilena u 1-buten, koji uključuje dovođenje etilena u kontakt s katalitičkim pripravkom koji sadrži:
- najmanje jedan prekursor nikla s oksidacijskim stanjem (+II),
- najmanje jedan fosfinski ligand s formulom PR1R2R3, u kojoj su odabrane skupine R1, R2 i R3, koje mogu biti identične ili različite, i koje mogu biti po izboru međusobno povezane, koje su odabrane
- od supstituiranih ili nesupstituiranih aromatskih skupina koje po izboru sadrže heteroelemente,
- i/ili od cikličkih ili necikličkih, supstituiranih ili nesupstituiranih hidrokarbilnih skupina koje po izboru sadrže heteroelemente,
- i najmanje jedno aktivacijsko sredstvo odabrano iz skupine koju čine klorirani i bromirani spojevi hidrokarbilaluminija, koji se koristi samostalno ili kao smjesa,
navedeni pripravak ima molarni omjer fosfinskog liganda prema prekursoru nikla od između 5 i 30 i molarni omjer aktivacijskog sredstva prema fosfinskom ligandu veći ili jednak 1,
postupak se provodi na temperaturi između 45°C i 250°C.
2. Postupak prema patentnom zahtjevu 1, naznačen time što su skupine R1, R2 i R3 navedenog fosfinskog liganda identične.
3. Postupak prema bilo kojem od zahtjeva 1 i 2, naznačen time što su aromatske skupine R1, R2 i R3 fosfinskog liganda PR1R2R3 odabrane iz skupa koji čine skupine fenil, o-tolil, m-tolil, p-tolil, mezitil, 3,5-dimetilfenil, 4-n-butilfenil, 4-metoksifenil, 2-metoksifenil, 3-metoksifenil, 4-metoksifenil, 2-izopropoksifenil, 4-metoksi-3,5-dimetilfenil, 3,5-di-tert-butil-4-metoksifenil, 4-klorofenil, 3,5-di(trifluorometil)-fenil, benzil, naftil, bisnaftil, piridil, bisfenil, furanil i tiofenil.
4. Postupak prema jednom od prethodnih patentnih zahtjeva, naznačen time što hidrokarbilne skupine R1, R2 i R3 fosfinskog liganda PR1R2R3 sadrže 1 do 20 ugljikovih atoma.
5. Postupak prema patentnom zahtjevu 4, naznačen time što su hidrokarbilne skupine R1, R2 i R3 fosfinskog liganda PR1R2R3 odabrane iz skupine koju čine skupine metil, etil, propil, izopropil, n-butil, tert-butil, ciklopentil, cikloil, benzil i adamantil.
6. Postupak prema jednom od prethodnih patentnih zahtjeva, naznačen time što je molarni omjer fosfinskog liganda prema prekursoru nikla između 5 i 25.
7. Postupak prema jednom od prethodnih patentnih zahtjeva, naznačen time što navedeni pripravak također sadrži Lewisovu bazu.
8. Postupak prema patentnom zahtjevu 7, naznačen time što je Lewisova baza odabrana od dietil etera, metil terc-butil etera, tetrahidrofurana, 1,4-dioksana, izoksazola, piridina, pirazina i pirimidina.
9. Postupak prema jednom od prethodnih patentnih zahtjeva, naznačen time što je aktivacijsko sredstvo odabrano iz skupa koji sadrži metilaluminijev diklorid (MeAlCl2), etilaluminijev diklorid (EtAlCl2), etilaluminijev seskviklorid (Et3Al2Cl3), dietilaluminijev klorid (Et2AlCl), diizobutilaluminijev klorid (iBu2AlCl), i izobutilaluminijev diklorid (iBuAlCl2), uzeto samo ili kao smjesa.
10. Postupak prema jednom od prethodnih patentnih zahtjeva, naznačen time što je prekursor nikla odabran iz skupa koji sadrži nikal(II) klorid, nikal(II) klorid (dimetoksietan), nikal(II) bromid, nikal(II) bromid (dimetoksietan), nikal(II) fluorid, nikal(II) jodid, nikal(II) sulfat, nikal(II) karbonat, nikal(II) dimetilglioksim, nikal(II) hidroksid, nikal(II) hidroksiacetat, nikal(II) oksalat, nikal(II) karboksilati, π-alilnikal(II) klorid, π-alilnikal(II) bromid, metallilnikal(II) klorid dimer, η3-alilnikal(II) heksafluorfosfat, η3-metallilnikal(II) heksafluorfosfat i 1,5-ciklooktadienilnikal(II), u njihovom hidratiziranom ili nehidratiziranom obliku, uzet sam ili kao smjesa.
11. Postupak prema jednom od patentnih zahtjeva 1 do 10, naznačen time što je prekursor nikla odabran iz skupa koji sadrži nikal(II) sulfat, nikal(II) karbonat, nikal(II) dimetilglioksim, nikal(II) hidroksid, nikal(II) hidroksiacetat, nikal(II) oksalat, nikal(II) karboksilati, π-alilnikal(II) klorid, π-alilnikal(II) bromid, metallilnikal(II) klorid dimer, η3-alilnikal(II) heksafluorfosfat, η3-metallilnikal(II) heksafluorfosfat i 1,5-ciklooktadienilnikal(II), u njihovom hidratiziranom ili nehidratiziranom obliku, uzet sam ili kao smjesa.
12. Postupak prema jednom od patentnih zahtjeva 1 do 11, naznačen time što se provodi u zatvorenom sustavu, u poluotvorenom sustavu, kontinuirano ili u serijama.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR1557247A FR3039430B1 (fr) | 2015-07-29 | 2015-07-29 | Nouvelle composition catalytique a base de nickel et de ligand de type phosphine et son utilisation dans un procede d'oligomerisation des olefines |
| EP16744370.4A EP3328542B1 (fr) | 2015-07-29 | 2016-07-26 | Procédé de dimerisation de l'éthylène |
| PCT/EP2016/067756 WO2017017087A1 (fr) | 2015-07-29 | 2016-07-26 | Nouvelle composition catalytique à base de nickel et de ligand de type phosphine et son utilisation dans un procede d'oligomerisation des olefines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20211805T1 true HRP20211805T1 (hr) | 2022-03-04 |
Family
ID=54186175
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20211805TT HRP20211805T1 (hr) | 2015-07-29 | 2016-07-26 | Postupak dimerizacije etilena |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US10633303B2 (hr) |
| EP (1) | EP3328542B1 (hr) |
| JP (1) | JP6807377B2 (hr) |
| CN (1) | CN108136383B (hr) |
| ES (1) | ES2898529T3 (hr) |
| FR (1) | FR3039430B1 (hr) |
| HR (1) | HRP20211805T1 (hr) |
| PL (1) | PL3328542T3 (hr) |
| PT (1) | PT3328542T (hr) |
| SA (1) | SA518390804B1 (hr) |
| TW (1) | TWI704125B (hr) |
| WO (1) | WO2017017087A1 (hr) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111408407B (zh) * | 2019-01-04 | 2023-07-21 | 中国石油化工股份有限公司 | 一种催化剂组合物、其制备方法及其在乙烯选择性二聚化合成1-丁烯的反应中的应用 |
| FR3103485B1 (fr) * | 2019-11-26 | 2023-03-24 | Ifp Energies Now | Procédé de séparation d’un effluent issu d’une étape d’oligomérisation |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| LU51826A1 (hr) * | 1965-09-06 | 1966-10-26 | ||
| FR1588162A (hr) * | 1966-04-14 | 1970-04-10 | ||
| DE1568729A1 (de) | 1966-12-09 | 1970-03-26 | Gelsenberg Benzin Ag | Katalysator fuer die Oligomerisation von Olefinen und Polymerisation von 1,3-Diolefinen |
| GB1282305A (en) * | 1969-05-01 | 1972-07-19 | Exxon Research Engineering Co | Oligomerization and cooligomerization process |
| US3755490A (en) * | 1969-05-01 | 1973-08-28 | Atlantic Richfield Co | Olefin polymerization catalyzed by a supported black amorphous nickelcomplex |
| US4242531A (en) | 1978-08-14 | 1980-12-30 | Phillips Petroleum Company | Olefin dimerization |
| US4487847A (en) | 1983-07-25 | 1984-12-11 | Phillips Petroleum Company | Ethylene dimerization |
| US5260499A (en) | 1992-01-14 | 1993-11-09 | Phillips Petroleum Company | Ethylene dimerization and catalyst therefor |
| US5237118A (en) | 1992-08-21 | 1993-08-17 | Phillips Petroleum Company | Ethylene oligomerization |
| FR2710280B1 (fr) * | 1993-09-22 | 1995-11-17 | Inst Francais Du Petrole | Composition catalytique et procédé pour la dimérisation des oléfines. |
| EP0908436A4 (en) * | 1996-04-10 | 2001-01-10 | Kyowa Yuka Kk | METHOD FOR DIMERIZING LOW OLEFINS |
| US6710007B2 (en) * | 2001-01-26 | 2004-03-23 | E. I. Du Pont De Nemours And Company | Polymerization of olefinic compounds |
| US6911506B2 (en) * | 2001-12-10 | 2005-06-28 | Chevron Phillips Chemical Company Lp | Catalyst composition and olefin polymerization using same |
| DE10303931B4 (de) | 2002-02-04 | 2013-04-18 | Institut Français du Pétrole | Katalytische Zusammensetzung zur Dimerisierung, Co-Dimerisierung, Oligomerisierung und Polymerisation der Olefine |
| WO2006022355A1 (ja) * | 2004-08-27 | 2006-03-02 | Mitsui Chemicals, Inc. | オレフィン重合用触媒、オレフィン重合体の製造方法、オレフィン共重合体、新規な遷移金属化合物および遷移金属化合物の製造方法 |
| DE102004054477A1 (de) * | 2004-11-11 | 2006-05-24 | Degussa Ag | Verfahren zur Herstellung von Trimethylcyclododecatrien |
| FR2895406B1 (fr) * | 2005-12-22 | 2010-08-13 | Inst Francais Du Petrole | Procede pour la fabrication de 2,3-dimethylbut-1-ene |
| TWI450878B (zh) * | 2008-07-23 | 2014-09-01 | Mitsui Chemicals Inc | 乙烯之寡聚化觸媒及其用途 |
| KR101760821B1 (ko) * | 2010-03-31 | 2017-07-24 | 차이나 페트로리움 앤드 케미컬 코포레이션 | 에틸렌 올리고머화용 촉매 조성물 및 올리고머화 방법 |
| US8395005B2 (en) * | 2010-10-13 | 2013-03-12 | Equistar Chemicals, Lp | Production of 1-butene and propylene from ethylene |
| FR2984311B1 (fr) * | 2011-12-20 | 2015-01-30 | IFP Energies Nouvelles | Procede de production d'octenes mettant en oeuvre la dimerisation de l'ethylene en butenes et la dimerisation des butenes en octenes |
| FR3045414B1 (fr) * | 2015-12-18 | 2019-12-27 | IFP Energies Nouvelles | Nouvelle composition catalytique a base de nickel et de ligand de type phosphine et d'une base de lewis et son utilisation dans un procede d'oligomerisation des olefines |
-
2015
- 2015-07-29 FR FR1557247A patent/FR3039430B1/fr active Active
-
2016
- 2016-07-26 PL PL16744370T patent/PL3328542T3/pl unknown
- 2016-07-26 US US15/747,793 patent/US10633303B2/en active Active
- 2016-07-26 PT PT167443704T patent/PT3328542T/pt unknown
- 2016-07-26 CN CN201680044336.5A patent/CN108136383B/zh active Active
- 2016-07-26 JP JP2018503651A patent/JP6807377B2/ja active Active
- 2016-07-26 HR HRP20211805TT patent/HRP20211805T1/hr unknown
- 2016-07-26 ES ES16744370T patent/ES2898529T3/es active Active
- 2016-07-26 EP EP16744370.4A patent/EP3328542B1/fr active Active
- 2016-07-26 WO PCT/EP2016/067756 patent/WO2017017087A1/fr active Application Filing
- 2016-07-27 TW TW105123794A patent/TWI704125B/zh active
-
2018
- 2018-01-25 SA SA518390804A patent/SA518390804B1/ar unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PT3328542T (pt) | 2021-11-30 |
| FR3039430B1 (fr) | 2019-07-05 |
| ES2898529T3 (es) | 2022-03-07 |
| JP2018522895A (ja) | 2018-08-16 |
| CN108136383A (zh) | 2018-06-08 |
| FR3039430A1 (fr) | 2017-02-03 |
| US10633303B2 (en) | 2020-04-28 |
| KR20180034420A (ko) | 2018-04-04 |
| PL3328542T3 (pl) | 2022-02-07 |
| CN108136383B (zh) | 2021-03-09 |
| WO2017017087A1 (fr) | 2017-02-02 |
| SA518390804B1 (ar) | 2021-08-04 |
| EP3328542B1 (fr) | 2021-09-08 |
| EP3328542A1 (fr) | 2018-06-06 |
| TWI704125B (zh) | 2020-09-11 |
| JP6807377B2 (ja) | 2021-01-06 |
| TW201714859A (zh) | 2017-05-01 |
| US20180215681A1 (en) | 2018-08-02 |
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