CN1094389C - 新的含镍催化组合物和烯烃二聚和齐聚的方法 - Google Patents

新的含镍催化组合物和烯烃二聚和齐聚的方法 Download PDF

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Publication number: CN1094389C
Authority: CN; China
Prior art keywords: phosphine; catalyst composition; compound; contain; nickel
Prior art date: 1993-09-22
Legal status (The legal status 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 status listed.): Expired - Lifetime

Application number

CN94116414A

Other languages

English (en)

Chinese (zh)

Other versions

CN1109065A (zh

Inventor

Y·肖文

S·艾恩洛夫特

H·奥利维埃

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

French Petroleum

Original Assignee

French Petroleum

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.)

1993-09-22

Filing date

1994-09-22

Publication date

2002-11-20

1994-09-22 Application filed by French Petroleum filed Critical French Petroleum

1995-09-27 Publication of CN1109065A publication Critical patent/CN1109065A/zh

2002-11-20 Application granted granted Critical

2002-11-20 Publication of CN1094389C publication Critical patent/CN1094389C/zh

2014-09-22 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

239000000203 mixture Substances 0.000 title claims abstract description 46
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 title claims abstract description 30
150000001336 alkenes Chemical class 0.000 title claims abstract description 16
229910052759 nickel Inorganic materials 0.000 title claims abstract description 14
238000000034 method Methods 0.000 title claims abstract description 12
238000006555 catalytic reaction Methods 0.000 title description 3
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 title description 2
XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims abstract description 75
-1 alkylaluminum halide Chemical class 0.000 claims abstract description 58
229910000073 phosphorus hydride Inorganic materials 0.000 claims abstract description 40
229910052782 aluminium Inorganic materials 0.000 claims abstract description 23
238000006471 dimerization reaction Methods 0.000 claims abstract description 10
239000003054 catalyst Substances 0.000 claims description 26
150000001875 compounds Chemical class 0.000 claims description 11
150000003003 phosphines Chemical group 0.000 claims description 8
239000004411 aluminium Substances 0.000 claims description 6
229910052794 bromium Inorganic materials 0.000 claims description 6
239000000460 chlorine Substances 0.000 claims description 6
229910052801 chlorine Inorganic materials 0.000 claims description 6
150000002816 nickel compounds Chemical class 0.000 claims description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
125000001309 chloro group Chemical group Cl* 0.000 claims description 5
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 4
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 4
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 4
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
150000001399 aluminium compounds Chemical class 0.000 claims description 3
150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 3
239000002131 composite material Substances 0.000 claims description 3
UAIZDWNSWGTKFZ-UHFFFAOYSA-L ethylaluminum(2+);dichloride Chemical compound CC[Al](Cl)Cl UAIZDWNSWGTKFZ-UHFFFAOYSA-L 0.000 claims description 3
125000000623 heterocyclic group Chemical group 0.000 claims description 3
239000012457 nonaqueous media Substances 0.000 claims description 3
150000003222 pyridines Chemical class 0.000 claims description 3
239000002904 solvent Substances 0.000 claims description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 2
229910021529 ammonia Inorganic materials 0.000 claims description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
VPLLTGLLUHLIHA-UHFFFAOYSA-N dicyclohexyl(phenyl)phosphane Chemical compound C1CCCCC1P(C=1C=CC=CC=1)C1CCCCC1 VPLLTGLLUHLIHA-UHFFFAOYSA-N 0.000 claims description 2
YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 claims description 2
150000002148 esters Chemical class 0.000 claims description 2
MGDOJPNDRJNJBK-UHFFFAOYSA-N ethylaluminum Chemical compound [Al].C[CH2] MGDOJPNDRJNJBK-UHFFFAOYSA-N 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
150000003512 tertiary amines Chemical class 0.000 claims description 2
IFXORIIYQORRMJ-UHFFFAOYSA-N tribenzylphosphane Chemical compound C=1C=CC=CC=1CP(CC=1C=CC=CC=1)CC1=CC=CC=C1 IFXORIIYQORRMJ-UHFFFAOYSA-N 0.000 claims description 2
WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 claims description 2
IGNTWNVBGLNYDV-UHFFFAOYSA-N triisopropylphosphine Chemical group CC(C)P(C(C)C)C(C)C IGNTWNVBGLNYDV-UHFFFAOYSA-N 0.000 claims description 2
239000004711 α-olefin Substances 0.000 claims description 2
UVPKUTPZWFHAHY-UHFFFAOYSA-L 2-ethylhexanoate;nickel(2+) Chemical compound [Ni+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O UVPKUTPZWFHAHY-UHFFFAOYSA-L 0.000 claims 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
MQRWBMAEBQOWAF-UHFFFAOYSA-N acetic acid;nickel Chemical compound [Ni].CC(O)=O.CC(O)=O MQRWBMAEBQOWAF-UHFFFAOYSA-N 0.000 claims 1
SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 claims 1
229940078494 nickel acetate Drugs 0.000 claims 1
150000003141 primary amines Chemical class 0.000 claims 1
150000003335 secondary amines Chemical class 0.000 claims 1
239000007788 liquid Substances 0.000 abstract description 6
238000006384 oligomerization reaction Methods 0.000 abstract description 2
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 10
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 10
238000006243 chemical reaction Methods 0.000 description 6
239000000539 dimer Substances 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 5
125000004432 carbon atom Chemical group C* 0.000 description 5
238000005660 chlorination reaction Methods 0.000 description 5
238000003756 stirring Methods 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
BFIMMTCNYPIMRN-UHFFFAOYSA-N 1,2,3,5-tetramethylbenzene Chemical compound CC1=CC(C)=C(C)C(C)=C1 BFIMMTCNYPIMRN-UHFFFAOYSA-N 0.000 description 4
239000000284 extract Substances 0.000 description 4
239000012530 fluid Substances 0.000 description 4
229930195733 hydrocarbon Natural products 0.000 description 4
WWUVJRULCWHUSA-UHFFFAOYSA-N 2-methyl-1-pentene Chemical compound CCCC(C)=C WWUVJRULCWHUSA-UHFFFAOYSA-N 0.000 description 3
239000004215 Carbon black (E152) Substances 0.000 description 3
230000003197 catalytic effect Effects 0.000 description 3
230000000447 dimerizing effect Effects 0.000 description 3
150000008282 halocarbons Chemical class 0.000 description 3
150000002430 hydrocarbons Chemical class 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
150000001398 aluminium Chemical class 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
125000003710 aryl alkyl group Chemical group 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000002609 medium Substances 0.000 description 2
150000002815 nickel Chemical class 0.000 description 2
125000004437 phosphorous atom Chemical group 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
239000000376 reactant Substances 0.000 description 2
VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
KAIPKTYOBMEXRR-UHFFFAOYSA-N 1-butyl-3-methyl-2h-imidazole Chemical compound CCCCN1CN(C)C=C1 KAIPKTYOBMEXRR-UHFFFAOYSA-N 0.000 description 1
BKILWHYRLBCASZ-UHFFFAOYSA-M 2-[bis(2-hydroxyethyl)amino]ethanol;2-hydroxypropanoate;phenylmercury(1+) Chemical compound CC(O)C([O-])=O.[Hg+]C1=CC=CC=C1.OCCN(CCO)CCO BKILWHYRLBCASZ-UHFFFAOYSA-M 0.000 description 1
NRGGMCIBEHEAIL-UHFFFAOYSA-N 2-ethylpyridine Chemical compound CCC1=CC=CC=N1 NRGGMCIBEHEAIL-UHFFFAOYSA-N 0.000 description 1
UFLLSVUGUWBXJA-UHFFFAOYSA-N 3,5-diethyl-1h-pyrazole Chemical class CCC=1C=C(CC)NN=1 UFLLSVUGUWBXJA-UHFFFAOYSA-N 0.000 description 1
YMRPKBLFDBUOAJ-UHFFFAOYSA-N 5-butyl-2-methyl-1h-imidazole Chemical class CCCCC1=CN=C(C)N1 YMRPKBLFDBUOAJ-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
GPWHDDKQSYOYBF-UHFFFAOYSA-N ac1l2u0q Chemical compound Br[Br-]Br GPWHDDKQSYOYBF-UHFFFAOYSA-N 0.000 description 1
230000002411 adverse Effects 0.000 description 1
150000001335 aliphatic alkanes Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
XHIHMDHAPXMAQK-UHFFFAOYSA-N bis(trifluoromethylsulfonyl)azanide;1-butylpyridin-1-ium Chemical compound CCCC[N+]1=CC=CC=C1.FC(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F XHIHMDHAPXMAQK-UHFFFAOYSA-N 0.000 description 1
230000031709 bromination Effects 0.000 description 1
238000005893 bromination reaction Methods 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
DLIJPAHLBJIQHE-UHFFFAOYSA-N butylphosphane Chemical compound CCCCP DLIJPAHLBJIQHE-UHFFFAOYSA-N 0.000 description 1
238000004523 catalytic cracking Methods 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
238000010908 decantation Methods 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
238000005194 fractionation Methods 0.000 description 1
239000011521 glass Substances 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
230000008676 import Effects 0.000 description 1
239000000463 material Substances 0.000 description 1
AIYYMMQIMJOTBM-UHFFFAOYSA-L nickel(ii) acetate Chemical compound [Ni+2].CC([O-])=O.CC([O-])=O AIYYMMQIMJOTBM-UHFFFAOYSA-L 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
125000001453 quaternary ammonium group Chemical group 0.000 description 1
238000007670 refining Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000004062 sedimentation Methods 0.000 description 1
238000007614 solvation Methods 0.000 description 1
238000004230 steam cracking Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1

Classifications

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- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24
- B01J31/28—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24 of the platinum group metals, iron group metals or copper
- 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
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- 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
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- 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
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
- B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
- B01J31/181—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- 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
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- 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
- 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
- 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
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/84—Metals of the iron group
- B01J2531/847—Nickel
- B—PERFORMING OPERATIONS; TRANSPORTING
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- B01J2531/90—Catalytic systems characterized by the solvent or solvent system used
- B—PERFORMING OPERATIONS; TRANSPORTING
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- 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
- B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
- B—PERFORMING OPERATIONS; TRANSPORTING
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- B01J31/22—Organic complexes
- B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
- B01J31/2208—Oxygen, e.g. acetylacetonates
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- C07C2527/06—Halogens; Compounds thereof
- C07C2527/128—Compounds comprising a halogen and an iron group metal or a platinum group metal
- 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
- 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
- C07C2531/22—Organic complexes
- 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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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
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)
Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)

CN94116414A 1993-09-22 1994-09-22 新的含镍催化组合物和烯烃二聚和齐聚的方法 Expired - Lifetime CN1094389C (zh)

Applications Claiming Priority (2)

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FR9311382		1993-09-22
FR9311382		1993-09-22

Publications (2)

Publication Number	Publication Date
CN1109065A CN1109065A (zh)	1995-09-27
CN1094389C true CN1094389C (zh)	2002-11-20

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CN94116414A Expired - Lifetime CN1094389C (zh)	1993-09-22	1994-09-22	新的含镍催化组合物和烯烃二聚和齐聚的方法

Country Status (8)

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US (2)	US5502018A (2)
EP (1)	EP0646413B1 (2)
JP (1)	JP4168099B2 (2)
KR (1)	KR950007942A (2)
CN (1)	CN1094389C (2)
CA (1)	CA2132700A1 (2)
DE (1)	DE69423165T2 (2)
TW (1)	TW287175B (2)

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JP2005523320A (ja) *	2002-04-22	2005-08-04	シェブロンフィリップスケミカルカンパニーエルピー	イオン性液体触媒を使った高粘度ポリアルファオレフィンの製造法
JP2007509750A (ja) *	2003-10-31	2007-04-19	シェブロンフィリップスケミカルカンパニーエルピー	イオン性液体触媒化学反応を改善する高剪断を与える方法及びシステム
US7271308B2 (en) *	2004-10-19	2007-09-18	Hercules Incorporated	Process for isomerization of alpha olefins to internal olefins
FR2879189B1 (fr)	2004-12-13	2007-03-30	Inst Francais Du Petrole	Methode pour transporter des hydrates en suspension dans des effluents de production utilisant un additif non-polluant
FR2880018B1 (fr) *	2004-12-27	2007-02-23	Inst Francais Du Petrole	Production de propylene mettant en oeuvre la dimerisation de l'ethylene en butene-1, l'hydro-isomerisation en butene-2 et la metathese par l'ethylene
US7732651B2 (en) *	2006-06-01	2010-06-08	Chevron Oronite Company, Llc	Method of making an alkylated aromoatic using acidic ionic liquid catalyst
KR101669300B1 (ko) *	2008-11-19	2016-10-25	바스프 에스이	올레핀의 올리고머화
JP2013103218A (ja) *	2011-11-17	2013-05-30	Petroleo Brasileiro Sa	オリゴマー化反応用クロム及びニッケル触媒と前記触媒を使ったアルファ−オレフィンを得る方法
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
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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
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1994
- 1994-09-13 EP EP94402045A patent/EP0646413B1/fr not_active Expired - Lifetime
- 1994-09-13 DE DE69423165T patent/DE69423165T2/de not_active Expired - Lifetime
- 1994-09-21 US US08/309,703 patent/US5502018A/en not_active Expired - Lifetime
- 1994-09-22 CA CA002132700A patent/CA2132700A1/fr not_active Abandoned
- 1994-09-22 TW TW083108754A patent/TW287175B/zh active
- 1994-09-22 KR KR1019940023836A patent/KR950007942A/ko not_active Ceased
- 1994-09-22 JP JP22748794A patent/JP4168099B2/ja not_active Expired - Lifetime
- 1994-09-22 CN CN94116414A patent/CN1094389C/zh not_active Expired - Lifetime
1995
- 1995-05-26 US US08/451,159 patent/US5550304A/en not_active Expired - Lifetime

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Also Published As

Publication number	Publication date
JPH07171404A (ja)	1995-07-11
JP4168099B2 (ja)	2008-10-22
US5502018A (en)	1996-03-26
TW287175B (2)	1996-10-01
CA2132700A1 (fr)	1995-03-23
EP0646413B1 (fr)	2000-03-01
CN1109065A (zh)	1995-09-27
EP0646413A1 (fr)	1995-04-05
DE69423165D1 (de)	2000-04-06
KR950007942A (ko)	1995-04-15
US5550304A (en)	1996-08-27
DE69423165T2 (de)	2000-07-06

Legal Events

Date	Code	Title	Description
1995-09-27	C06	Publication
1995-09-27	PB01	Publication
1997-01-08	C10	Entry into substantive examination
1997-01-08	SE01	Entry into force of request for substantive examination
2002-11-20	C14	Grant of patent or utility model
2002-11-20	GR01	Patent grant
2014-10-22	C17	Cessation of patent right
2014-10-22	CX01	Expiry of patent term	Expiration termination date: 20140922 Granted publication date: 20021120

Publication	Publication Date	Title
CN1094389C (zh)	2002-11-20	新的含镍催化组合物和烯烃二聚和齐聚的方法
JP4273257B2 (ja)	2009-06-03	オレフィンの二量化、共二量化、オリゴマー化及び重合用の触媒組成物
CN102869445B (zh)	2015-11-25	低聚催化剂系统以及低聚烯烃的方法
JP4845270B2 (ja)	2011-12-28	オレフィンの二量化、共二量化およびオリゴマー化触媒組成物
US5536689A (en)	1996-07-16	Catalytic composition and a process for the dimerization of olefins
US5525567A (en)	1996-06-11	Catalytic composition and olefin disproportion process
JP4977537B2 (ja)	2012-07-18	オレフィンの二量化用触媒組成物およびオレフィンの二量化方法
RU2004127935A (ru)	2006-01-27	Высоковязкие полиальфаолефины, полученные с применением ионного жидкого катализатора
US20030181775A1 (en)	2003-09-25	Catalyst composition containing an aluminoxane for dimerizing, co-dimerizing and oligomerizing olefins
FR2611700A1 (fr)	1988-09-09	Procede de dimerisation ou de codimerisation d'olefines
EP0091232B1 (en)	1985-07-10	Butene dimerization method
EP1235767A1 (en)	2002-09-04	Hydrocarbon conversion process
EP1122230B1 (fr)	2003-06-25	Procédé pour la dimérisation sélective du propylène principalement en dimères ramifiés
US3800000A (en)	1974-03-26	Process for recovering a nickel(0) oligomerization catalyst in the form of a nickel(ii) dimerization catalyst
DE60110489T2 (de)	2005-09-22	Katalytische Zusammensetzung und Verfahren für die Dimerisierung, Codimerisierung und Oligomerisierung von Olefinen
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WO2015041879A1 (en)	2015-03-26	Catalyst and process for the co-dimerization of ethylene and propylene
FR2835447A1 (fr)	2003-08-08	Composition catalytique pour la dimerisation, la co-dimerisation et l'oligomerisation des olefines
WO2019105844A1 (fr)	2019-06-06	Nouvelle composition catalytique a base de nickel, d'un phosphonium et son utilisation pour l'oligomerisation des olefines
US3734975A (en)	1973-05-22	Catalytic dimerization of olefins with a bis(isoquinoline,dihalocobalt (ii) complex
FR2835448A1 (fr)	2003-08-08	Composition catalytique pour la dimerisation, la co-dimerisation, l'oligomerisation et la polymerisation des olefines
KR20240028765A (ko)	2024-03-05	1-부텐의 제조 방법
US3686353A (en)	1972-08-22	Catalytic dimerization of olefins with cobalt complexes
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WO2005044444A1 (ja)	2005-05-19	オレフィンのオリゴマー化触媒