WO2004056479A1 - Tetramerization of olefins - Google Patents
Tetramerization of olefins Download PDFInfo
- Publication number
- WO2004056479A1 WO2004056479A1 PCT/ZA2003/000187 ZA0300187W WO2004056479A1 WO 2004056479 A1 WO2004056479 A1 WO 2004056479A1 ZA 0300187 W ZA0300187 W ZA 0300187W WO 2004056479 A1 WO2004056479 A1 WO 2004056479A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- phenyl
- catalyst system
- group
- transition metal
- methyl
- Prior art date
Links
- 150000001336 alkenes Chemical class 0.000 title claims abstract description 34
- 238000000034 method Methods 0.000 claims abstract description 147
- 239000003054 catalyst Substances 0.000 claims abstract description 88
- 239000003446 ligand Substances 0.000 claims abstract description 79
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 16
- 150000003623 transition metal compounds Chemical class 0.000 claims abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 185
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 159
- 239000005977 Ethylene Substances 0.000 claims description 159
- CPOFMOWDMVWCLF-UHFFFAOYSA-N methyl(oxo)alumane Chemical compound C[Al]=O CPOFMOWDMVWCLF-UHFFFAOYSA-N 0.000 claims description 132
- 239000011651 chromium Substances 0.000 claims description 91
- 239000000203 mixture Substances 0.000 claims description 90
- -1 methylene, dimethylmethylene Chemical group 0.000 claims description 85
- 229910052723 transition metal Inorganic materials 0.000 claims description 55
- 150000003624 transition metals Chemical class 0.000 claims description 55
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 claims description 54
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 45
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 41
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 37
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 28
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 27
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 26
- 125000003118 aryl group Chemical group 0.000 claims description 25
- 239000002243 precursor Substances 0.000 claims description 25
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 24
- 125000005647 linker group Chemical group 0.000 claims description 24
- 229910052698 phosphorus Inorganic materials 0.000 claims description 24
- 239000012190 activator Substances 0.000 claims description 23
- 150000001875 compounds Chemical class 0.000 claims description 23
- 239000011574 phosphorus Substances 0.000 claims description 23
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 21
- 125000001424 substituent group Chemical group 0.000 claims description 21
- 229910052757 nitrogen Inorganic materials 0.000 claims description 20
- 125000005842 heteroatom Chemical group 0.000 claims description 18
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 17
- 125000004429 atom Chemical group 0.000 claims description 17
- 229910052804 chromium Inorganic materials 0.000 claims description 17
- 239000011669 selenium Substances 0.000 claims description 16
- 229910052751 metal Inorganic materials 0.000 claims description 15
- 239000002184 metal Substances 0.000 claims description 15
- 239000004305 biphenyl Substances 0.000 claims description 14
- YVSMQHYREUQGRX-UHFFFAOYSA-N 2-ethyloxaluminane Chemical compound CC[Al]1CCCCO1 YVSMQHYREUQGRX-UHFFFAOYSA-N 0.000 claims description 13
- 229910052787 antimony Inorganic materials 0.000 claims description 13
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims description 13
- 229910052785 arsenic Inorganic materials 0.000 claims description 13
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 claims description 13
- 229910052797 bismuth Inorganic materials 0.000 claims description 13
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 12
- 239000004711 α-olefin Substances 0.000 claims description 11
- 150000004696 coordination complex Chemical class 0.000 claims description 10
- 125000001624 naphthyl group Chemical group 0.000 claims description 10
- 229910052711 selenium Inorganic materials 0.000 claims description 10
- 125000003944 tolyl group Chemical group 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 125000004104 aryloxy group Chemical group 0.000 claims description 8
- 235000010290 biphenyl Nutrition 0.000 claims description 8
- BFGKITSFLPAWGI-UHFFFAOYSA-N chromium(3+) Chemical compound [Cr+3] BFGKITSFLPAWGI-UHFFFAOYSA-N 0.000 claims description 8
- WBKDDMYJLXVBNI-UHFFFAOYSA-K chromium(3+);2-ethylhexanoate Chemical compound [Cr+3].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O WBKDDMYJLXVBNI-UHFFFAOYSA-K 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 238000011065 in-situ storage Methods 0.000 claims description 7
- 238000002156 mixing Methods 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 6
- 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 description 6
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 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 6
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methylcyclopentane Chemical compound CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 claims description 6
- 125000002524 organometallic group Chemical group 0.000 claims description 6
- 230000003647 oxidation Effects 0.000 claims description 6
- 238000007254 oxidation reaction Methods 0.000 claims description 6
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 6
- 125000005023 xylyl group Chemical group 0.000 claims description 6
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 239000005864 Sulphur Substances 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 150000002899 organoaluminium compounds Chemical class 0.000 claims description 5
- DIIIISSCIXVANO-UHFFFAOYSA-N 1,2-Dimethylhydrazine Chemical compound CNNC DIIIISSCIXVANO-UHFFFAOYSA-N 0.000 claims description 4
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims description 4
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 4
- 229910007161 Si(CH3)3 Inorganic materials 0.000 claims description 4
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 4
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 4
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims description 4
- RPBPCPJJHKASGQ-UHFFFAOYSA-K chromium(3+);octanoate Chemical compound [Cr+3].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O.CCCCCCCC([O-])=O RPBPCPJJHKASGQ-UHFFFAOYSA-K 0.000 claims description 4
- CYOMBOLDXZUMBU-UHFFFAOYSA-K chromium(3+);oxolane;trichloride Chemical compound [Cl-].[Cl-].[Cl-].[Cr+3].C1CCOC1.C1CCOC1.C1CCOC1 CYOMBOLDXZUMBU-UHFFFAOYSA-K 0.000 claims description 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 4
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 claims description 4
- NFJPEKRRHIYYES-UHFFFAOYSA-N methylidenecyclopentane Chemical compound C=C1CCCC1 NFJPEKRRHIYYES-UHFFFAOYSA-N 0.000 claims description 4
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 claims description 4
- 150000007522 mineralic acids Chemical class 0.000 claims description 4
- 229910052750 molybdenum Inorganic materials 0.000 claims description 4
- 239000011733 molybdenum Substances 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 239000001294 propane Substances 0.000 claims description 4
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 229910001494 silver tetrafluoroborate Inorganic materials 0.000 claims description 4
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 4
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 4
- 125000003107 substituted aryl group Chemical group 0.000 claims description 4
- 229910052715 tantalum Inorganic materials 0.000 claims description 4
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 claims description 4
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 125000004014 thioethyl group Chemical group [H]SC([H])([H])C([H])([H])* 0.000 claims description 4
- 229910052719 titanium Inorganic materials 0.000 claims description 4
- 239000010936 titanium Substances 0.000 claims description 4
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- LOFJKBAHPJENQS-UHFFFAOYSA-N tris(oxomethylidene)chromium Chemical compound O=C=[Cr](=C=O)=C=O LOFJKBAHPJENQS-UHFFFAOYSA-N 0.000 claims description 4
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims description 4
- 229910052721 tungsten Inorganic materials 0.000 claims description 4
- 239000010937 tungsten Substances 0.000 claims description 4
- 229910052720 vanadium Inorganic materials 0.000 claims description 4
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 claims description 4
- 229910052726 zirconium Inorganic materials 0.000 claims description 4
- 239000000178 monomer Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Natural products C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- 229910017053 inorganic salt Inorganic materials 0.000 claims 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 375
- 239000000047 product Substances 0.000 description 115
- 239000000243 solution Substances 0.000 description 105
- 238000006243 chemical reaction Methods 0.000 description 96
- 238000009826 distribution Methods 0.000 description 46
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 44
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 20
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 20
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 12
- OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 12
- SHZIWNPUGXLXDT-UHFFFAOYSA-N caproic acid ethyl ester Natural products CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 12
- 239000000306 component Substances 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 9
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 7
- 239000007795 chemical reaction product Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 239000012442 inert solvent Substances 0.000 description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000013065 commercial product Substances 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 238000000769 gas chromatography-flame ionisation detection Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- REJGOFYVRVIODZ-UHFFFAOYSA-N phosphanium;chloride Chemical class P.Cl REJGOFYVRVIODZ-UHFFFAOYSA-N 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 3
- UYRPRYSDOVYCOU-UHFFFAOYSA-N 2-diphenylphosphanylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 UYRPRYSDOVYCOU-UHFFFAOYSA-N 0.000 description 2
- 229910018516 Al—O Inorganic materials 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000007818 Grignard reagent Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 102000010909 Monoamine Oxidase Human genes 0.000 description 2
- 108010062431 Monoamine oxidase Proteins 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- KBSCQVGRWYLGED-UHFFFAOYSA-N N-diaminophosphoryl-N-propan-2-ylpropan-2-amine dihydrochloride Chemical compound Cl.Cl.CC(C)N(C(C)C)P(N)(N)=O KBSCQVGRWYLGED-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 2
- INJBDKCHQWVDGT-UHFFFAOYSA-N chloro(diethyl)phosphane Chemical compound CCP(Cl)CC INJBDKCHQWVDGT-UHFFFAOYSA-N 0.000 description 2
- XGRJZXREYAXTGV-UHFFFAOYSA-N chlorodiphenylphosphine Chemical compound C=1C=CC=CC=1P(Cl)C1=CC=CC=C1 XGRJZXREYAXTGV-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000000539 dimer Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000003365 glass fiber Substances 0.000 description 2
- 150000004795 grignard reagents Chemical class 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
- 150000002431 hydrogen Chemical group 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 239000003607 modifier Substances 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- KDIAMAVWIJYWHN-UHFFFAOYSA-N propylcyclopentane Chemical compound CCCC1CCCC1 KDIAMAVWIJYWHN-UHFFFAOYSA-N 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 2
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1 -dodecene Natural products CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 1
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
- RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 description 1
- QNJUXDQESJRITJ-UHFFFAOYSA-N 2-diethylphosphanyl-n-(2-diethylphosphanylethyl)ethanamine Chemical compound CCP(CC)CCNCCP(CC)CC QNJUXDQESJRITJ-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
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- 239000012279 sodium borohydride Substances 0.000 description 1
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- 125000006850 spacer group Chemical group 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- LGQXXHMEBUOXRP-UHFFFAOYSA-N tributyl borate Chemical compound CCCCOB(OCCCC)OCCCC LGQXXHMEBUOXRP-UHFFFAOYSA-N 0.000 description 1
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- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical compound CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups C07C2531/02 - C07C2531/24
- C07C2531/34—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups C07C2531/02 - C07C2531/24 of chromium, molybdenum or tungsten
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F110/00—Homopolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F110/02—Ethene
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2410/00—Features related to the catalyst preparation, the catalyst use or to the deactivation of the catalyst
- C08F2410/03—Multinuclear procatalyst, i.e. containing two or more metals, being different or not
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
- C08F4/62—Refractory metals or compounds thereof
- C08F4/639—Component covered by group C08F4/62 containing a transition metal-carbon bond
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
- C08F4/62—Refractory metals or compounds thereof
- C08F4/64—Titanium, zirconium, hafnium or compounds thereof
- C08F4/659—Component covered by group C08F4/64 containing a transition metal-carbon bond
- C08F4/65912—Component covered by group C08F4/64 containing a transition metal-carbon bond in combination with an organoaluminium compound
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
- C08F4/62—Refractory metals or compounds thereof
- C08F4/64—Titanium, zirconium, hafnium or compounds thereof
- C08F4/659—Component covered by group C08F4/64 containing a transition metal-carbon bond
- C08F4/6592—Component covered by group C08F4/64 containing a transition metal-carbon bond containing at least one cyclopentadienyl ring, condensed or not, e.g. an indenyl or a fluorenyl ring
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
- C08F4/62—Refractory metals or compounds thereof
- C08F4/64—Titanium, zirconium, hafnium or compounds thereof
- C08F4/659—Component covered by group C08F4/64 containing a transition metal-carbon bond
- C08F4/6592—Component covered by group C08F4/64 containing a transition metal-carbon bond containing at least one cyclopentadienyl ring, condensed or not, e.g. an indenyl or a fluorenyl ring
- C08F4/65922—Component covered by group C08F4/64 containing a transition metal-carbon bond containing at least one cyclopentadienyl ring, condensed or not, e.g. an indenyl or a fluorenyl ring containing at least two cyclopentadienyl rings, fused or not
- C08F4/65927—Component covered by group C08F4/64 containing a transition metal-carbon bond containing at least one cyclopentadienyl ring, condensed or not, e.g. an indenyl or a fluorenyl ring containing at least two cyclopentadienyl rings, fused or not two cyclopentadienyl rings being mutually bridged
Definitions
- This invention relates to an olefin tetramerisation process, a catalyst system for tetramerisation of olefins and the identification and use of ligands for a catalyst system for tetramerisation of olefins.
- This invention defines a process and catalyst system that facilitates the production of 1-octene in high selectivity, while avoiding the co-production of significant quantities of butenes, other octene isomers, specific higher oligomers and polyethylene.
- the catalyst system can also be used for the tetramerisation of other olefins, especially ⁇ (alpha) -olefins.
- a nickel catalyst comprising a chelating ligand, preferably 2- diphenyl phosphino benzoic acid (DPPBA), a nickel precursor, preferably NiCI 2 .6H 2 O, and a catalyst activator, preferably sodium tetraphenylborate, catalyse the oligomerisation of ethylene to yield a mixture of linear olefins containing 1-octene.
- DPPBA 2- diphenyl phosphino benzoic acid
- a nickel precursor preferably NiCI 2 .6H 2 O
- a catalyst activator preferably sodium tetraphenylborate
- Ziegler-type technologies based on trialkylaluminium catalysts are also commercially used to oligomerise ethylene to mixtures of olefins that reportedly contain 13-25 mass % 1- octene (Chem Systems PERP reports 90-1 , 93-6, and 94/95S12).
- chromium-based catalysts containing heteroatomic ligands with both phosphorus and nitrogen heteroatoms selectively catalyse the trimerisation of ethylene to 1-hexene.
- heteroatomic ligands for ethylene trimerisation include bis(2-diethylphosphino-ethyl) amine (WO 03/053891 , hereby fully incorporated herein by means of reference) as well as (o- methoxyphenyl) 2 PN(methyl)P(o-methoxyphenyl) 2 (WO 02/04119, hereby fully incorporated herein by means of reference).
- WO 02/04119 Example 16 teaches the production of octenes using a trimerisation of olefins process and catalyst system. In this instance, 1- butene was co-trimerised with two ethylene molecules to give 30% octenes. However, the nature of these octenes was not disclosed and the applicant believes that they consist of a mixture of linear and branched octenes.
- This invention relates to a process for selectively producing tetrameric products.
- This invention specifically relates to a process for selectively producing tetrameric products such as 1-octene from olefins such as ethylene..
- the invention relates to a process for selectively producing tetrametric products using a transition metal catalyst system containing a heteroatomic ligand.
- a process for tetramerisation of olefins wherein the product of the tetramerisation process is an olefin and makes up more than 30% of the product stream of the process.
- the tetramerisation process includes the step of contacting an olefinic feedstream with a catalyst system which includes a transition metal and a heteroatomic ligand and wherein the product of the tetramerisation process is an olefin and makes up more than 30% of the product stream of the process.
- % will be understood to be a mass %.
- heteroatomic a ligand that contains at least two heteroatoms, which can be the same or different, where the heteroatoms may be selected from phosphorus, arsenic, antimony, sulphur, oxygen, bismuth, selenium or nitrogen.
- the feedstream will be understood to include an olefin to be tetramerised and can be introduced into the process according to the invention in a continuous or batch fashion.
- the product stream will be understood to include a tetramer, which tetramer is produced according to the invention in a continuous or batch fashion.
- the feedstream may include an ⁇ -olefin and the product stream may include at least 30%, preferably at least 35%, of a tetramerised ⁇ -olefin monomer.
- the process may include a process for tetramerisation of ⁇ -olefins.
- ⁇ -olefins is meant all hydrocarbon compounds with terminal double bonds. This definition includes ethylene, propylene, 1-butene, isobutylene, 1-pentene, 1-hexene, 1-octene and the like.
- the process may include a process for tetramerisation of ⁇ -olefins to selectively yield tetrameric ⁇ -olefin products.
- the olefinic feedstream may include ethylene and the product stream may include at least 30% 1-octene.
- the process may be a process for tetramerisation of ethylene.
- the invention allows the ligand, catalyst system and/or process conditions to be selected to give a product stream of more than 40%, 50%, 60% or 70% ⁇ -olefins. It may be preferable, depending on the further use of the product stream, to have such high selectivities of the ⁇ -olefin.
- the olefinic feedstream may include ethylene and the (C 6 + C 8 ) : (C 4 + C 10 ) ratio in the product stream may be more than 2.5:1.
- the olefinic feedstream may include ethylene and the C 8 : C 6 ratio in the product stream is more than 1.
- the ethylene may be contacted with the catalyst system at a pressure of preferably greater than 10 barg, more preferably greater than 30 barg.
- the heteroatomic ligand may be described by the following general formula (R) n A-B-C(R) m where A and C are independently selected from a group which comprises phosphorus, arsenic, antimony, oxygen, bismuth, sulphur, selenium, and nitrogen, and B is a linking group between A and C, and R is independently selected from any homo or hetero hydrocarbyl group and n and m is determined by the respective valence and oxidation state of A and/or C.
- a and/or C may be a potential electron donor for coordination with the transition metal.
- An electron donor is defined as that entity that donates electrons used in chemical, including dative covalent, bond, formation.
- the heteroatomic ligand may be described by the following general formula (R 1 )(R 2 )A-B-C(R 3 )(R 4 ) where A and C are independently selected from a group which comprises phosphorus, arsenic, antimony, bismuth and nitrogen and B is a linking group between A and C, and R 1 , R 2 , R 3 and R 4 are independently selected from hydrocarbyl or hetero hydrocarbyl or substituted hydrocarbyl or substituted hetero hydrocarbyl groups.
- the heteroatomic ligand may be described by the following general formula (R 1 )(R 2 )A-B-C(R 3 )(R 4 ) where A and C are independently selected from a group which comprises phosphorus, arsenic, antimony, bismuth and nitrogen and B is a linking group between A and C, and R 1 , R 2 , R 3 and R 4 are independently non-aromatic or aromatic, including hetero aromatic, groups.
- any of the groups R 1 , R 2 , R 3 and R 4 may independently be linked to one or more of each other or to the linking group B to form a cyclic structure together with A and C, A and B or B and C.
- R 1 , R 2 , R 3 and R 4 may be not electron donating.
- R 1 , R 2 , R 3 and R 4 may independently be non aromatic or aromatic, including hetero aromatic, groups and not all the groups R 1 , R 2 , R 3 and R 4 , if aromatic, have a substituent on the atom adjacent to the atom bound to A or C.
- Each non electron donating substituent on one or more of R 1 , R 2 , R 3 and R 4 may be non-polar.
- IUPAC defines non-polar as an entity without a permanent electric dipole moment.
- Suitable non-polar substituents may be a methyl, ethyl, propyl, butyl, isopropyl, isobutyl, terf-butyl, pentyl, hexyl, cyclopentyl, 2-methylcyclohexyl, cyclohexyl, cylopentadienyl, phenyl, bi-phenyl, naphthyl, tolyl, xylyl, mesityl, ethenyl, propenyl and benzyl group, or the like.
- R 1 , R 2 , R 3 and R 4 may be independently selected from a group comprising a benzyl, phenyl, tolyl, xylyl, mesityl, biphenyl, naphthyl, anthracenyl, methoxy, ethoxy, phenoxy, tolyloxy, dimethylamino, diethylamino, methylethylamino, thiophenyl, pyridyl, thioethyl, thiophenoxy, trimethylsilyl, dimethylhydrazyl, methyl, ethyl, ethenyl, propyl, butyl, propenyl, propynyl, cyclopentyl, cyclohexyl, ferrocenyl and tetrahydrofuranyl group.
- R 1 , R 2 , R 3 and R 4 may independently be selected from a group comprising a phenyl, tolyl,
- B may be selected from any one of a group comprising: organic linking groups comprising a hydrocarbyl, substituted hydrocarbyl, heterohydrocarbyl and a substituted heterohydrocarbyl; inorganic linking groups comprising single atom links; ionic links; and a group comprising methylene, dimethylmethylene, 1 ,2-ethane, 1 ,2- phenylene, 1 ,2-propane, 1 ,2-catechol, 1 ,2-dimethylhydrazine, -B(R 5 )-, -Si(R 5 ) -, - P(R 5 )- and -N(R 5 )- where R 5 is hydrogen, a hydrocarbyl or substituted hydrocarbyl, a substituted heteroatom or a halogen.
- B may be -N(R 5 )- and R 5 is a hydrocarbyl or a substituted hydrocarbyl group.
- R 5 may be hydrogen or may be selected from the groups consisting of alkyl, substituted alkyl, aryl, substituted aryl, aryloxy, substituted aryloxy, halogen, nitro, alkoxycarbonyl, carbonyloxy, alkoxy, aminocarbonyl, carbonylamino, dialkylamino, silyl groups or derivatives thereof, and aryl substituted with any of these substituents.
- R 5 may be an isopropyl, a 1-cyclohexyl-ethyl, a 2-methyl-cyclohexyl or a 2-octyl group.
- B may be selected to be a single atom spacer.
- a single atom linking spacer is defined as a substituted or non-substituted atom that is bound directly to A and C.
- a and/or C may be independently oxidised by S, Se, N or O.
- a and C may be independently phosphorus or phosphorus oxidised by S or Se or N or O.
- the ligand may also contain multiple (R) n A-B-C(R) m units.
- ligands include dendrimeric ligands as well as ligands where the individual units are coupled either via one or more of the R groups or via the linking group B . More specific, but not limiting, examples of such ligands may include 1 ,2-di- (N(P(phenyl) 2 ) 2 )-benzene, 1 ,4-di-(N(P(phenyl) 2 ) 2 )-benzene,
- ligands can be prepared using procedures known to one skilled in the art and procedures disclosed in published literature. Examples of ligands are: (phenyl) 2 PN(methyl)P(phenyl) 2 , (phenyl) 2 PN(pentyl)P(phenyl) 2>
- the catalyst system may include an activator and the process may include the step of combining in any order a heteroatomic ligand with a transition metal precursor and an activator.
- the process may include the step of generating a heteroatomic coordination complex in situ from a transition metal precursor and a heteroatomic ligand.
- the process may include the step of adding a pre-formed coordination complex, prepared using a heteroatomic ligand and a transition metal precursor, to a reaction mixture, or the step of adding separately to the reactor, a heteroatomic ligand and a transition metal precursor such that a heteroatomic coordination complex of a transition metal is generated in situ.
- generating a heteroatomic coordination complex in situ is meant that the complex is generated in the medium in which catalysis takes place.
- the heteroatomic coordination complex is generated in situ.
- the transition metal precursor, and heteroatomic ligand are combined (both in situ and ex situ) to provide metal/ligand ratios from about 0.01:100 to 10 000:1, and preferably, from about 0.1:1 to 10:1.
- the transition metal may be selected from any one of a group comprising chromium, molybdenum, tungsten, titanium, tantalum, vanadium and zirconium, preferably chromium.
- the transition metal precursor which, upon mixing with the heteroatomic ligand and an activator, catalyses ethylene tetramerisation in accordance with the invention, may be a simple inorganic or organic salt, a co-ordination or organometallic complex and may be selected from any one of a group comprising chromium trichloride tris- tetrahydrofuran complex, (benzene)tricarbonyl chromium, chromium (III) octanoate, chromium (III) acetylacetonoate, chromium hexacarbonyl, and chromium (III) 2- ethylhexanoate.
- the preferred transition metal precursors include chromium (III) acetylacetonoate and chromium (III) 2-ethylhexanoate.
- the heteroatomic ligand can be modified to be attached to a polymer chain so that the resulting heteroatomic coordination complex of the transition metal is soluble at elevated temperatures, but becomes insoluble at 25°C.
- This approach would enable the recovery of the complex from the reaction mixture for reuse and has been used for other catalyst as described by D.E. Bergbreiter et a/., J. Am. Chem. Soc, 1987, 109, 177-179.
- these transition metal complexes can also be immobilised by binding the heteroatomic ligands to silica, silica gel, polysiloxane or alumina or the like backbone as, for example, demonstrated by C. Yuanyin et a/., Chinese J. React.
- the activator for use in the process may in principle be any compound that generates an active catalyst when combined with the heteroatomic ligand and the transition metal precursor. Mixtures of activators may also be used. Suitable compounds include organoaluminium compounds, organoboron compounds, organic salts, such as methyllithium and methylmagnesium bromide, inorganic acids and salts, such as tetrafluoroboric acid etherate, silver tetrafluoroborate, sodium hexafluoroantimonate and the like.
- Suitable organoaluminium compounds include compounds of the formula AIR 3 , where each R is independently a CrC 12 alkyl, an oxygen containing moiety or a halide, and compounds such as LiAIH 4 and the like. Examples include trimethylaluminium (TMA), triethylaluminium (TEA), tri-isobutylaluminium (TIBA), tri-t?- octylaluminium, methylaluminium dichloride, ethylaluminium dichloride, dimethylaluminium chloride, diethylaluminium chloride, aluminium isopropoxide, ethylaluminiumsesquichloride, methylaluminiumsesquichloride, and aluminoxanes.
- TMA trimethylaluminium
- TEA triethylaluminium
- TIBA tri-isobutylaluminium
- tri-t?- octylaluminium methylalumin
- Aluminoxanes are well known in the art as typically oligomeric compounds which can be prepared by the controlled addition of water to an alkylaluminium compound, for example trimethylaluminium. Such compounds can be linear, cyclic, cages or mixtures thereof. Mixtures of different aluminoxanes may also be used in the process.
- organoboron compounds examples include boroxines, NaBH 4 , triethylborane, tris(pentafluoropheny)borane, tributyl borate and the like.
- the activator may also be or contain a compound that acts as a reducing or oxidising agent, such as sodium or zinc metal and the like, or oxygen and the like.
- the activator may be selected from alkylaluminoxanes such as methylaluminoxane (MAO) and ethylaluminoxane (EAO) as well as modified alkylaluminoxanes such as modified methylaluminoxane (MMAO).
- alkylaluminoxanes such as methylaluminoxane (MAO) and ethylaluminoxane (EAO)
- modified alkylaluminoxanes such as modified methylaluminoxane (MMAO).
- Modified methylaluminoxane (a commercial product from Akzo Nobel) contains modifier groups such as isobutyl or n-octyl groups, in addition to methyl groups.
- the transition metal and the aluminoxane may be combined in proportions to provide Al/metal ratios from about 1 :1 to 10 000:1, preferably from about 1 :1 to 1000:1 , and more preferably from 1:1 to 300:1.
- the process may include the step of adding to the catalyst system a trialkylaluminium compound in amounts of between 0.01 to 1000 mol per mol of alkylaluminoxane.
- aluminoxanes generally also contain considerable quantities of the corresponding trialkylaluminium compounds used in their preparation. The presence of these trialkylaluminium compounds in aluminoxanes can be attributed to their incomplete hydrolysis with water. Any quantity of a trialkylaluminium compound quoted in this disclosure is additional to alkylaluminium compounds contained within the aluminoxanes.
- the process may include the step of mixing the components of the catalyst system at any temperature between -20°C and 250°C in the presence of an olefin.
- an olefin may stabilise the catalyst system.
- the individual components of the catalyst system described herein may be combined simultaneously or sequentially in any order, and in the presence or absence of a solvent, in order to give an active catalyst.
- the mixing of the catalyst components can be conducted at any temperature between -100°C and 250°C.
- the presence of an olefin during the mixing of the catalyst components generally provides a protective effect which may result in improved catalyst performance.
- the preferred temperature range may be between 20°C and 100°C.
- the catalyst system in accordance with the invention, or its individual components, may also be immobilised by supporting it on a support material, for example, silica, alumina, MgCI 2 , zirconia or mixtures thereof, or on a polymer, for example polyethylene, polypropylene, polystyrene, or poly(aminostyrene).
- a support material for example, silica, alumina, MgCI 2 , zirconia or mixtures thereof, or on a polymer, for example polyethylene, polypropylene, polystyrene, or poly(aminostyrene).
- the catalyst can be formed in situ in the presence of the support material, or the support can be pre- impregnated or premixed, simultaneously or sequentially, with one or more of the catalyst components.
- the support material can also act as a component of the activator. This approach would also facilitate the recovery of the catalyst from the reaction mixture for reuse.
- the support can also act as a catalyst component, for example where such supports contain aluminoxane functionalities or where the support is capable of performing similar chemical functions as an aluminoxane, which is for instance the case with IOLATM (a commercial product from Grace Davison).
- reaction products as described herein may be prepared using the disclosed catalyst system by a homogeneous liquid phase reaction in the presence or absence of an inert solvent, and/or by slurry reaction where the catalyst system is in a form that displays little or no solubility, and/or a two-phase liquid/liquid reaction, and/or a bulk phase reaction in which neat reagent and/or product olefins serve as the dominant medium, and/or gas phase reaction, using conventional equipment and contacting techniques.
- the process may also be carried out in an inert solvent.
- Any inert solvent that does not react with the activator can be used.
- These inert solvents may include any saturated aliphatic and unsaturated aliphatic and aromatic hydrocarbon and halogenated hydrocarbon.
- Typical solvents include, but are not limited to, benzene, toluene, xylene, cumene, heptane, methylcyclohexane, methylcyclopentane, cyclohexane, 1-hexene, 1-octene, ionic liquids and the like.
- the process may be carried out at pressures from atmospheric to 500 barg. Ethylene pressures in the range of 10-70 barg are preferred. Particularly preferred pressures range from 30-50 barg.
- the process may be carried out at temperatures from -100 °C to 250 °C. Temperatures in the range of 15-130 °C are preferred. Particularly preferred temperatures range from 35-100°C.
- the heteroatomic coordination complex and reaction conditions are selected such that the yield of 1-octene from ethylene is greater than 30 mass %, preferably greater than 35 mass %.
- yield refers to grams of 1-octene formed per 100g of total reaction product formed.
- the process may also yield different quantities of 1-butene, 1- hexene, methylcyclopentane, methylene cyclopentane, propylcyclopentane, propylene cyclopentane, specific higher oligomers and polyethylene, depending on the nature of the heteroatomic ligand and the reaction conditions.
- a number of these products cannot be formed via conventional ethylene oligomerisation and trimerisation technologies in the yields observed in the present invention.
- the catalyst, its individual components, reagents, solvents and reaction products are generally employed on a once-through basis, any of these materials can, and are indeed preferred to be recycled to some extent in order to minimise production costs.
- the process may be carried out in a plant which includes any type of reactor.
- reactors include, but are not limited to, batch reactors, semi-batch reactors and continuous reactors.
- the plant may include, in combination a) a reactor, b) at least one inlet line into this reactor for olefin reactant and the catalyst system, c) effluent lines from this reactor for oligomerisation reaction products, and d) at least one separator to separate the desired oligomerisation reaction products, wherein the catalyst system may include a heteroatomic coordination complex of a transition metal precursor and an activator, as described herein.
- the reactor and a separator may be combined to facilitate the simultaneous formation of reaction products and separation of these compounds from the reactor.
- This process principle is commonly known as reactive distillation.
- the catalyst system exhibits no solubility in the solvent or reaction products, and is fixed in the reactor so that it does not exit the reactor with the reactor product, solvent and unreacted olefin, the process principle is commonly known as catalytic distillation.
- a catalyst system for the tetramerisation of olefins.
- the catalyst system may include a heteroatomic ligand as described above and a transition metal.
- the catalyst system may also include an activator as described above.
- the heteroatomic ligand is described by the following general formula (R) n A-B-C(R) m where A and C are independently selected from a group which comprises phosphorus, arsenic, antimony, oxygen, bismuth, sulphur, selenium, and nitrogen, and B is a linking group between A and C, and R is independently selected from any homo or hetero hydrocarbyl group and n and m is determined by the respective valence and oxidation state of A and/or C.
- a and/or C may be a potential electron donor for coordination with the transition metal.
- the heteroatomic ligand may be described by the following general formula (R 1 )(R 2 )A-B-C(R 3 )(R 4 ) where A and C are independently selected from a group which comprises phosphorus, arsenic, antimony, bismuth and nitrogen and B is a linking group between A and C, and R 1 , R 2 , R 3 and R 4 are independently selected from hydrocarbyl or hetero hydrocarbyl or substituted hydrocarbyl or substituted hetero hydrocarbyl groups.
- the heteroatomic ligand may also be described by the following general formula (R 1 )(R 2 )A-B-C(R 3 )(R 4 ) where A and C are independently selected from a group which comprises phosphorus, arsenic, antimony, bismuth, and nitrogen and B is a linking group between A and C, and R 1 , R 2 , R 3 and R 4 are independently non-aromatic or aromatic, including hetero aromatic, groups.
- any of the groups R 1 , R 2 , R 3 and R 4 may independently be linked to one or more of each other or to the linking group B to form a cyclic structure together with A and C, A and B or B and C.
- R 1 , R 2 , R 3 and R 4 may not be electron donating.
- R 1 , R 2 , R 3 and R 4 may be independently non aromatic or aromatic, including hetero aromatic, groups and not all the groups R 1 , R 2 , R 3 and R 4 , if aromatic, have a substituent on the atom adjacent to the atom bound to A or C. It appears to the applicant that single atom spacers having steric bulk promote the selectivity towards 1-octene if ethylene is tetramerised, especially if there are no substituents on the atom of the aromatic group adjacent to the atom bound to A or C. Each non electron donating substituent may be non polar. This also appears to promote selectivity towards 1-octene.
- Suitable non-polar substituents may be a methyl, ethyl, propyl, butyl, isopropyl, isobutyl, te/ -butyl, pentyl, hexyl, cyclopentyl, 2-methylcyclohexyl, cyclohexyl, cylopentadienyl, phenyl, bi-phenyl, naphthyl, tolyl, xylyl, mesityl, ethenyl, propenyl and benzyl group, or the like.
- R 1 , R 2 , R 3 and R 4 may independently be selected from a group comprising a benzyl, phenyl, tolyl, xylyl, mesityl, biphenyl, naphthyl, anthracenyl, methoxy, ethoxy, phenoxy, tolyloxy, dimethylamino, diethylamino, methylethylamino, thiophenyl, pyridyl, thioethyl, thiophenoxy, trimethylsilyl, dimethylhydrazyl, methyl, ethyl, ethenyl, propyl, butyl, propenyl, propynyl, cyclopentyl, cyclohexyl, ferrocenyl and tetrahydrofuranyl group.
- R 1 , R 2 , R 3 and R 4 may independently be selected from a group comprising a phenyl, tolyl,
- B may be selected from any one of a group comprising: organic linking groups comprising a hydrocarbyl, substituted hydrocarbyl, heterohydrocarbyl and a substituted heterohydrocarbyl; inorganic linking groups comprising single atom links; ionic links; and a group comprising methylene, dimethylmethylene, 1 ,2-ethane, 1 ,2- phenylene, 1 ,2-propane, 1 ,2-catechol, 1 ,2-dimethylhydrazine, -B(R 5 )-, -Si(R 5 ) 2 -, - P(R 5 )- and -N(R 5 )- where R 5 is hydrogen, a hydrocarbyl or substituted hydrocarbyl, a substituted heteroatom or a halogen.
- B may be -N(R 5 )- and R 5 is a hydrocarbyl or a substituted hydrocarbyl group.
- R 5 may be hydrogen or may be selected from the groups consisting of alkyl, substituted alkyl, aryl, substituted aryl, aryloxy, substituted aryloxy, halogen, nitro, alkoxycarbonyl, carbonyloxy, alkoxy, aminocarbonyl, carbonylamino, dialkylamino, silyl groups or derivatives thereof, and aryl substituted with any of these substituents.
- R 5 may be an isopropyl, a 1-cyclohexylethyl, a 2-methylcyclohexyl or a 2-octyl group.
- B may be selected to be a single atom spacer.
- the applicant has found that such a single atom spacer between A and C generally increases the selectivity of the tetramerisation catalyst.
- a and/or C may be independently oxidised by S, Se, N or O.
- a and C may preferably be independently phosphorus or phosphorus oxidised by S or Se or N or O.
- the ligand may also contain multiple (R) n A-B-C(R) m units.
- Not limiting examples of such ligands include ligands where the individual units are coupled either via one or more of the R groups or via the linking group B. More specific, but not limiting, examples of such ligands may include 1 ,2-di-(N(P(phenyl) 2 ) 2 )-benzene, 1 ,4-di- (N(P(phenyl) 2 ) 2 )-benzene, N(CH2CH 2 N(P(phenyl) 2 ) 2 ) 3 and 1,4-di-
- the ligand may be selected from any one or more of a group comprising (phenyl) 2 PN(methyl)P(phenyl) 2 , (phenyl) 2 PN(pentyl)P(phenyl) 2 ,
- the transition metal may be selected from any one of a group comprising chromium, molybdenum, tungsten, titanium, tantalum, vanadium and zirconium, preferably chromium.
- the transition metal may be derived from a transition metal precursor selected from a simple inorganic or organic salt, a co-ordination or organometallic complex and may be selected from a group comprising chromium trichloride tris-tetrahydrofuran complex, (benzene)tricarbonyl chromium, chromium (III) octanoate, chromium (III) acetylacetonoate, chromium hexacarbonyl, and chromium (III) 2-ethylhexanoate.
- the preferred transition metal precursors include chromium (III) acetylacetonoate and chromium (III) 2-ethylhexanoate.
- the transition metal precursor and heteroatomic ligand may have metal/ligand ratios from about 0.01 :100 to 10 000:1 , preferably from about 0.1 :1 to 10:1.
- the activator may in principle be any compound that generates an active catalyst when combined with the heteroatomic ligand and the transition metal precursor. Mixtures of activators may also be used. Suitable compounds include organoaluminium compounds, organoboron compounds, organic salts, such as methyllithium and methylmagnesium bromide, inorganic acids and salts, such as tetrafluoroboric acid etherate, silver tetrafluoroborate, sodium hexafluoroantimonate and the like.
- the activator may be selected from alkylaluminoxanes such as methylaluminoxane (MAO) and ethylaluminoxane (EAO) as well as modified alkylaluminoxanes such as modified methylaluminoxane (MMAO).
- alkylaluminoxanes such as methylaluminoxane (MAO) and ethylaluminoxane (EAO)
- modified alkylaluminoxanes such as modified methylaluminoxane (MMAO).
- Modified methylaluminoxane (a commercial product from Akzo Nobel) contains modifier groups such as isobutyl or n-octyl groups, in addition to methyl groups.
- the transition metal and the aluminoxane may be in such proportions relative to each other to provide Al/metal ratios from about 1 :1 to 10 000:1 , preferably from about 1:1 to 1000:1 , and more preferably from 1 :1 to 300:
- the catalyst system may also include a trialkylaluminium compound in amounts of between 0.01 to 100 mol per mol of aluminoxane.
- a ligand as described above, for a catalyst system, as described above, for the tetramerisation of olefins.
- the invention also extends to the identification and use of ligands suitable for use in a tetramerisation of olefins process or catalyst system.
- EAO ethylaluminoxane
- 72.042 g/mol corresponding to the (CH 3 CH 2 - Al-O) building block
- modified methylaluminoxane prepared from a 70:30 mixture of trimethylaluminium and tri-isobutylaluminium as 70.7 g/mol corresponding to the (Me 0 . 7 oisonBu 0 . 3 o-AI-O) unit.
- Ethylene oligomerisation products were analysed by GC-MS and GC-FID.
- the mixed heteroatomic PNP ligands were made by reacting amines and phosphine chlorides R 2 PCI as described in (a) Ewart et al, J. Chem. Soc. 1964, 1543; (b) Dossett, S.J. et al, Chem. Commun., 2001, 8, 699; (c) Balakrishna, M.S. et al, J. Organomet. Chem. 1990, 390, 2, 203).
- the respective phosphine chlorides R 2 PCI were prepared as described in literature (Casalnuovo, A.L. et al, J. Am. Chem. Soc. 1994, 116, 22, 9869; Rajanbabu, T.V.
- the (phenyl) 2 PN(methyl)N(methyl)P(phenyl) 2 ligand was prepared according to Slawin et al. (Slawin, A.M.Z et al, J. Chem. Soc, Dalton Trans. 2002, 513).
- Slawin, A.M.Z et al J. Chem. Soc, Dalton Trans. 2002, 513.
- the preparation method of Schmidbaur et al. was used (Schmidbaur, H. et al, J.Organomet. Chem. 1984, 271, 173).
- Example 1 Preparation of the (phenyl) 2 PN(isopropyl)P(phenyl) 2 ligand
- Example 1a Preparation of N,N-diisopropylphosphoramide dichloride
- the Grignard reagent was added to N,N-diisopropylphosphoramide dichloride (6.64 ml, 36 mmol) in THF (100 ml) at 0 °C After stirring at room temperature overnight the mixture was diluted with cyclohexane (200 ml) and dry HCI gas was bubbled through the solution for 0.5 hours. After filtration of the precipitate, the solvent was removed to give a mixture of the phosphine chloride and bromide in an 80% yield. This crude product was not isolated and all was used in the next step.
- Example 2 Ethylene tetramerisation reaction using CrCI 3 (tetrahydrofuran) 3 , (phenyl) 2 PN(methyl)P(phenyl) 2 and MAO
- Example 3 Ethylene tetramerisation reaction using CrCI 3 (tetrahydrofuran) 3 , (phenyl) 2 PN(methyl)P(phenyl) 2 and MAO
- Example 4 Ethylene tetramerisation reaction using CrCI 3 (tetrahydrofuran) 3 , (phenyl) 2 PN(methyl)P(phenyl) 2 and MAO
- Example 5 Ethylene tetramerisation reaction using CrCI 3 (tetrahydrofuran) 3 , (phenyl) 2 PN(pentyl)P(phenyl) 2 and MAO
- the pressure reactor was charged with ethylene after which the reactor temperature was controlled at 65°C, while the ethylene pressure was maintained at 30 barg. The reaction was terminated after 60 min, and the procedure of Example 2 above was employed. The product mass was 74.84 g.
- the product distribution of this example is summarised in Table 1.
- Example 6 Ethylene tetramerisation reaction using CrCI 3 (tetrahydrofuran) 3 , (phenyl) 2 PN(benzyl)P(phenyl) 2 and MAO
- Example 7 Ethylene tetramerisation reaction using CrCI 3 (tetrahydrofuran) 3 , (phenyl) 2 PN(phenyl)P(phenyl) 2 and MAO
- Example 8 Ethylene tetramerisation reaction using CrCI 3 (tetrahydrofuran) 3 , (phenyl) 2 PN(p-methoxy-phenyl)P(phenyl) 2 and MAO
- the pressure reactor was charged with ethylene after which the reactor temperature was controlled at 65°C, while the ethylene pressure was maintained at 30 barg. The reaction was terminated after 60 min, and the procedure of Example 2 above was employed. The product mass was 7.01 g.
- the product distribution of this example is summarised in Table 1.
- Example 9 Ethylene tetramerisation reaction using CrCI 3 (tetrahydrofuran) 3 , (phenyl) 2 PN(p- t butylphenyl)P(phenyl) 2 and MAO
- the pressure reactor was charged with ethylene after which the reactor temperature was controlled at 65°C, while the ethylene pressure was maintained at 30 barg. The reaction was terminated after 180 min, and the procedure of Example 2 above was employed. The product mass was 62.15 g.
- the product distribution of this example is summarised in Table 1.
- Example 10 Ethylene tetramerisation reaction using Cr(2-ethylhexanoate) 3 , (phenyl) 2 PN(allyl)P(phenyl) 2 and MAO
- the pressure reactor was charged with ethylene after which the reactor temperature was controlled at 65°C, while the ethylene pressure was maintained at 30 barg. The reaction was terminated after 30 min, and the procedure of Example 2 above was employed. The product mass was 12.68 g.
- the product distribution of this example is summarised in Table 1.
- Example 11 Ethylene tetramerisation reaction using Cr(acetylacetonoate) 3 , (phenyl) 2 PN[(CH 2 ) 3 Si(OMe) 3 ]P(phenyl) 2 and MAO
- the pressure reactor was charged with ethylene after which the reactor temperature was controlled at 65°C, while the ethylene pressure was maintained at 30 barg. The reaction was terminated after 30 min, and the procedure of Example 2 above was employed. The product mass was 72.96 g.
- the product distribution of this example is summarised in Table 1.
- Example 12 Ethylene tetramerisation reaction using Cr(acetylacetonoate) 3 , (phenyl) 2 PN[(CH 2 ) 3 -N-morpholine]P(phenyl) 2 and MAO
- the pressure reactor was charged with ethylene after which the reactor temperature was controlled at 65°C, while the ethylene pressure was maintained at 30 barg. The reaction was terminated after 30 min, and the procedure of Example 2 above was employed. The product mass was 22.2 g.
- the product distribution of this example is summarised in Table 1.
- Example 13 Ethylene tetramerisation reaction using CrCI 3 (tetrahydrofuran) 3 , (phenyl) 2 PN('propyl)P(phenyl) 2 and MAO
- the pressure reactor was charged with ethylene after which the reactor temperature was controlled at 65°C, while the ethylene pressure was maintained at 30 barg. The reaction was terminated after 180 min, and the procedure of Example 2 above was employed. The product mass was 56.44 g.
- the product distribution of this example is summarised in Table 1.
- Example 14 Ethylene tetramerisation reaction using CrCI 3 (tetrahydrofuran) 3 , (phenyl) 2 PN('propyl)P(phenyl) 2 and MAO A solution of 17.1 mg of (phenyl) 2 PN('propyl)P(phenyl) 2 (0.04 mmol) in 10 ml of toluene was added to a solution of 7.5 mg CrCI 3 (tetrahydrofuran) 3 (0.02 mmol) in 10 ml toluene in a Schlenk vessel.
- Example 15 Ethylene tetramerisation reaction using Cr(2-ethylhexanoate) 3 , (phenyI) 2 PN('propyl)P(phenyl) 2 and MAO
- the pressure reactor was charged with ethylene after which the reactor temperature was controlled at 45°C, while the ethylene pressure was maintained at 45 barg.
- the reaction was terminated after 50 min, and the procedure of Example 2 above was employed.
- the product mass was 64.71 g.
- the product distribution of this example is summarised in Table 1.
- Example 16 Ethylene tetramerisation reaction using Cr(acetylacetonoate) 3 , (phenyl) 2 PN('propyl)P(phenyl) 2 and MAO
- Example 17 Ethylene tetramerisation reaction using Cr(acetylacetonoate) 3 , (phenyl) 2 PN('propyl)P(phenyl) 2 and EAO/TMA
- the pressure reactor was charged with ethylene after which the reactor temperature was controlled at 45°C, while the ethylene pressure was maintained at 45 barg.
- the reaction was terminated after 37 min, and the procedure of Example 2 above was employed.
- the product mass was 29.03 g.
- the product distribution of this example is summarised in Table 1.
- Example 18 Ethylene tetramerisation reaction using Cr(acetylacetonoate) 3 , (phenyl) 2 PN('propyl)P(phenyl) 2 and MMAO
- the pressure reactor was charged with ethylene after which the reactor temperature was controlled at 45°C, while the ethylene pressure was maintained at 45 barg.
- the reaction was terminated after 15 min, and the procedure of Example 2 above was employed.
- the product mass was 74.11 g.
- the product distribution of this example is summarised in Table 1.
- Example 19 Ethylene tetramerisation reaction using Cr(acetylactonate) 3 , (phenyl) 2 PN('propyl)P(phenyl) 2 and supported MAO
- Example 20 Ethylene tetramerisation reaction using Cr(acetylacetonoate) 3 , (phenyl) 2 PN('propyl)P(phenyl) 2 and MAO
- the pressure reactor was charged with ethylene after which the reactor temperature was controlled at 45°C, while the ethylene pressure was maintained at 45 barg.
- the reaction was terminated after 25 min, and the procedure of Example 2 above was employed.
- the product mass was 118.78 g.
- the product distribution of this example is summarised in Table 1.
- Example 21 Ethylene tetramerisation reaction using Cr(acetylacetonoate) 3 , (phenyl) 2 PN('propyl)P(phenyl) 2 and MAO
- the pressure reactor was charged with ethylene after which the reactor temperature was controlled at 45°C, while the ethylene pressure was maintained at 45 barg.
- the reaction was terminated after 10 min, and the procedure of Example 2 above was employed.
- the product mass was 70.6 g.
- the product distribution of this example is summarised in Table 1.
- Example 22 Ethylene tetramerisation reaction using Cr(acetylacetonoate) 3 , (phenyl) 2 PN('propyl)P(phenyl) 2 and MAO
- Example 23 Ethylene tetramerisation reaction using Cr(acetylacetonoate) 3 , (phenyl) 2 PN('propyl)P(phenyl) 2 and MAO
- Example 24 Ethylene tetramerisation reaction using Cr(acetylacetonoate) 3 , (2- naphthyl) 2 PN(methyl)P(2-naphthyl) 2 and MAO
- the pressure reactor was charged with ethylene after which the reactor temperature was maintained at 65°C, while the ethylene pressure was kept at 30 barg. The reaction was terminated after 30 min, and the procedure of Example 2 above was employed. The product mass was 45.18 g.
- the product distribution of this example is summarised in Table 1.
- Example 25 Ethylene tetramerisation reaction using Cr(acetylacetonoate) 3 , (p- biphenyl) 2 PN(methyl)P(p-biphenyl) 2 and MAO
- the pressure reactor was charged with ethylene after which the reactor temperature was controlled at 65°C, while the ethylene pressure was maintained at 30 barg. The reaction was terminated after 30 min, and the procedure of Example 2 above was employed. The product mass was 26.41 g.
- the product distribution of this example is summarised in Table 1.
- Example 26 Ethylene tetramerisation reaction using Cr(acetylacetonoate) 3 , (m- methylphenyl) 2 PN(methyl)P(m-methylphenyl) 2 and MAO
- the pressure reactor was charged with ethylene after which the reactor temperature was controlled at 45°C, while the ethylene pressure was maintained at 65 barg.
- the reaction was terminated after 30 min, and the procedure of Example 2 above was employed.
- the product mass was 52.34 g.
- the product distribution of this example is summarised in Table 1.
- Example 27 Ethylene tetramerisation reaction using Cr(acetylacetonoate) 3 , (p- methylphenyl) 2 PN(methyl)P(p-methylphenyl) 2 and MAO
- the pressure reactor was charged with ethylene after which the reactor temperature was maintained at 65°C, while the ethylene pressure was kept at 45 barg. The reaction was terminated after 15 min, and the procedure of Example 2 above was employed. The product mass was 80.59 g.
- the product distribution of this example is summarised in Table 1.
- Example 28 Ethylene tetramerisation reaction using Cr(acetylacetonoate) 3 , (o- ethyIphenyl)(Ph)PN('propyl)PPh 2 and MAO
- a solution of 30.1 mg of (o-ethylphenyl)(Ph)PN('propyl)PPh 2 (0.066 mmol) in 10 ml of toluene was added to a solution of 11.5 mg Cr(acetylacetonoate) 3 (0.033 mmol) in 10 ml toluene in a Schlenk vessel.
- the pressure reactor was charged with ethylene after which the reactor temperature was controlled at 45°C, while the ethylene pressure was maintained at 45 barg.
- the reaction was terminated after 30 min, and the procedure of Example 2 above was employed.
- the product mass was 33.06 g.
- the product distribution of this example is summarised in Table 1.
- Example 30 Ethylene tetramerisation reaction using Cr(acetylacetonoate) 3 , (phenyl) 2 PN('propyl)P(phenyl) 2 and MAO
- the pressure reactor was charged with ethylene after which the reactor temperature was controlled at 45°C, while the ethylene pressure was maintained at 45 barg.
- the reaction was terminated after 30 min, and the procedure of Example 2 above was employed.
- the liquid product mass was 22.45 g.
- the product distribution of this example is summarised in Table 1.
- Example 32 Ethylene tetramerisation reaction using Cr(acetylacetonoate) 3 , (2- thiophenyl) 2 PN(methyl)P(2-thiophenyl) 2 and MAO
- the pressure reactor was charged with ethylene after which the reactor temperature was controlled at 45°C, while the ethylene pressure was maintained at 45 barg.
- the reaction was terminated after 30 min, and the procedure of Example 2 above was employed.
- the product mass was 14.7 g.
- the product distribution of this example is summarised in Table 1.
- Example 33 Ethylene tetramerisation reaction using Cr(acetylacetonoate) 3 , (phenyl) 2 PN('propyl)P(phenyl) 2 and MAO
- Example 34 Ethylene tetramerisation reaction using Cr(acetylacetonoate) 3 , (phenyl) 2 PN(SiMe 3 )P(phenyl) 2 and MAO
- the pressure reactor was charged with ethylene after which the reactor temperature was controlled at 45°C, while the ethylene pressure was maintained at 45 barg.
- the reaction was terminated after 30 min, and the procedure of Example 2 above was employed.
- the product mass was 26.9 g.
- the product distribution of this example is summarised in Table 1.
- Example 35 Ethylene tetramerisation reaction using Cr(acetyIacetonoate) 3 , [(phenyl 2 P) 2 NCH 2 CH 2 ]N and MAO
- Example 36 Ethylene tetramerisation reaction using Cr(acetylacetonoate) 3 , (o- methylphenyl) 2 PN('propyl)P(o-methylphenyl)(phenyl) and MAO
- the pressure reactor was charged with ethylene after which the reactor temperature was controlled at 45°C, while the ethylene pressure was maintained at 45 barg.
- the reaction was terminated after 30 min, and the procedure of Example 2 above was employed.
- the product mass was 55.45 g.
- the product distribution of this example is summarised in Table 1.
- Example 38 Ethylene tetramerisation reaction using [Cr ⁇ (phenyl) 2 PN(phenyl)P(phenyl) 2 ⁇ CI 2 ( ⁇ -CI)] 2 and MAO
- Example 40 Ethylene tetramerisation reaction using Cr(2-ethylhexanoate) 3 , (ethyl) 2 PN(methyl)P(ethyl) 2 and MAO
- Example 42 Ethylene tetramerisation reaction using [Cr ⁇ (ethyl) 2 PN(methyl)P(ethyl) 2 ⁇ CI 2 ( ⁇ -CI)] 2 and MAO
- N-(diphenylphosphino)methylamine (1.870g, 7.69 mmol) in toluene (15 ml) was slowly added to a solution of chlorodiethylphosphine (0.986, 7.92 mmol) in toluene (20 ml) and triethylamine (5 ml). The mixture was stirred overnight before being filtered through a glass fibre filter. The solvents were removed under vacuum and 10 ml of water was added. The product was extracted in petroleum ether (3 x 5 ml) and organics combined. Removal of the solvent under vacuum yielded 2.200g (86%) of the product. 31 P ⁇ H ⁇ NMR: 49, 43 ppm.
- Example 44 Ethylene tetramerisation reaction using Cr(2-ethylhexanoate) 3 , (phenyl) 2 PN(isopropyl)P(ethyl) 2 and MAO
- Example 45 Ethylene tetramerisation reaction using Cr(2-ethylhexanoate) 3 , (phenyl)(ethyl)PN(methyl)P(ethyl)(phenyl) and MAO
- Example 46 Ethylene tetramerisation reaction using Cr(2-ethylhexanoate) 3 , (phenyl)(ethyl)PN(isopropyl)P(phenyl) 2 and MAO
- the pressure reactor was charged with ethylene after which the reactor temperature was controlled at 45°C, while the ethylene pressure was maintained at 45 barg.
- the reaction was terminated after 30 min, and the procedure of Example 2 above was employed.
- the product mass was 8.45 g.
- the product distribution of this example is summarised in Table 1.
- Example 48 Ethylene tetramerisation reaction using Cr(acetylacetonoate) 3 , (phenyl) 2 PCH 2 CH 2 P(phenyl) 2 and MAO
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Abstract
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AU2003297546A AU2003297546A1 (en) | 2002-12-20 | 2003-12-19 | Tetramerization of olefins |
AT03813854T ATE491516T1 (en) | 2002-12-20 | 2003-12-19 | TETRAMERIZATION OF OLEFINS |
CNB2003801091277A CN100548946C (en) | 2002-12-20 | 2003-12-19 | Four of alkene gathers |
DE60335416T DE60335416D1 (en) | 2002-12-20 | 2003-12-19 | TETRAMERIZATION OF OLEFINES |
EP03813854A EP1581342B1 (en) | 2002-12-20 | 2003-12-19 | Tetramerization of olefins |
JP2005511969A JP2006517528A (en) | 2002-12-20 | 2003-12-19 | Tetramerization of olefins |
BR0317510-3A BR0317510A (en) | 2002-12-20 | 2003-12-19 | Olefin tetramerization |
CA2510194A CA2510194C (en) | 2002-12-20 | 2003-12-19 | Tetramerization of olefins |
US10/539,517 US7511183B2 (en) | 2002-12-20 | 2003-12-19 | Tetramerization of olefins |
BRPI0317510-3A BRPI0317510B1 (en) | 2002-12-20 | 2003-12-19 | Olefin tetramerization process and catalyst system |
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WO2008146215A1 (en) * | 2007-05-28 | 2008-12-04 | Sasol Technology (Pty) Limited | Two stage activation of oligomerisation catalyst and oligomerisation of olefinic compounds in the presence of an oligomerisation catalyst so activated |
WO2009060343A1 (en) * | 2007-11-07 | 2009-05-14 | Sasol Technology (Proprietary) Limited | Process for polymerising or oligomerising a hydrocarbon |
US7550639B2 (en) | 2005-07-27 | 2009-06-23 | Sumitomo Chemical Company, Limited | Process for producing olefin oligomer |
WO2009060342A3 (en) * | 2007-11-07 | 2009-06-25 | Sasol Tech Pty Ltd | Process for polymerising or oligomerising a hydrocarbon |
EP2106854A1 (en) * | 2008-04-04 | 2009-10-07 | Saudi Basic Industries Corporation | Catalyst for oligomerization of ethylene, method for preparation thereof and process for oligomerization using it |
US7687672B2 (en) | 2006-02-03 | 2010-03-30 | Exxonmobil Chemical Patents Inc. | In-line process for generating comonomer |
US7727926B2 (en) | 2005-07-21 | 2010-06-01 | Chevron Phillips Chemical Company Lp | Diimine metal complexes, methods of synthesis, and method of using in oligomerization and polymerization |
WO2010092554A1 (en) | 2009-02-16 | 2010-08-19 | Sasol Technology (Pty) Limited | Oligomerisation of olefinic compounds in the presence of an activated oligomerisation catalyst |
US7803886B2 (en) | 2006-12-22 | 2010-09-28 | Shell Oil Company | Ligands and catalyst systems thereof for the catalytic oligomerization of olefinic monomers |
EP2239056A1 (en) | 2009-04-09 | 2010-10-13 | Saudi Basic Industries Corporation | Catalyst composition and process for oligomerization of ethylene |
US7820581B2 (en) | 2004-02-20 | 2010-10-26 | Chevron Phillips Chemical Company Lp | Methods of preparation of an olefin oligomerization catalyst |
US7858833B2 (en) | 2006-02-03 | 2010-12-28 | Exxonmobil Chemical Patents Inc. | Process for generating linear alpha olefin comonomers |
US7902415B2 (en) | 2007-12-21 | 2011-03-08 | Chevron Phillips Chemical Company Lp | Processes for dimerizing or isomerizing olefins |
US7910670B2 (en) | 2005-08-19 | 2011-03-22 | Chevron Phillips Chemical Company Lp | Methods of preparation of an olefin oligomerization catalyst |
WO2011045701A1 (en) | 2009-10-16 | 2011-04-21 | Sasol Technology (Proprietary) Limited | Separation of components from a multi-component hydrocarbon stream which includes ethylene |
WO2011048527A1 (en) | 2009-10-19 | 2011-04-28 | Sasol Technology (Pty) Limited | Oligomerisation of olefinic compounds with reduced polymer formation |
WO2011085951A1 (en) | 2010-01-15 | 2011-07-21 | Basell Polyolefine Gmbh | Oligomerization of olefins |
US7994376B2 (en) | 2004-02-19 | 2011-08-09 | Chevron Phillips Chemical Company Lp | Olefin oligomerization |
WO2011098160A1 (en) | 2010-02-12 | 2011-08-18 | Enantia, S.L. | Enantiomerically enriched aminodiphosphines as ligands for the preparation of catalysts for asymmetric synthesis |
WO2011108772A1 (en) | 2010-03-03 | 2011-09-09 | 에스케이이노베이션 주식회사 | Highly active and highly selective ethylene oligomerization catalyst, and preparation method of hexene or octene using same |
WO2011140629A1 (en) * | 2010-05-12 | 2011-11-17 | Nova Chemicals (International) S.A. | Oligomenzation of alpha olefins |
US8067609B2 (en) | 2007-01-08 | 2011-11-29 | Exxonmobil Chemical Patents Inc. | Methods for oligomerizing olefins with chromium pyridine thioether catalysts |
US8138348B2 (en) | 2007-01-08 | 2012-03-20 | Exxonmobil Chemical Patents Inc. | Methods for oligomerizing olefins with chromium pyridine mono-oxazoline catalysts |
WO2012055943A2 (en) | 2010-10-28 | 2012-05-03 | Basell Polyolefine Gmbh | Oligomerization of olefins |
US8227653B2 (en) | 2009-03-27 | 2012-07-24 | Exxonmobil Chemical Patents Inc. | Olefin oligomerization reaction processes exhibiting reduced fouling |
US8252874B2 (en) | 2006-12-22 | 2012-08-28 | Shell Oil Company | Ligands and catalyst systems for the oligomerization of olefinic monomers |
US8309779B2 (en) | 2007-08-16 | 2012-11-13 | Sk Innovation Co., Ltd. | Ethylene oligomerization catalyst systems having enhanced selectivity |
US8329608B2 (en) | 2004-02-20 | 2012-12-11 | Chevron Phillips Chemical Company Lp | Methods of preparation of an olefin oligomerization catalyst |
WO2013110170A1 (en) | 2012-01-25 | 2013-08-01 | Nova Chemicals (International) S.A. | P-n-p ligand |
WO2013168103A1 (en) | 2012-05-09 | 2013-11-14 | Sasol Technology (Proprietary) Limited | Oligomerisation of olefinic compounds with reduced polymer formation |
WO2013168098A1 (en) | 2012-05-09 | 2013-11-14 | Sasol Technology (Proprietary) Limited | Separation of components from a multi-component hydrocarbon stream |
WO2013168106A1 (en) | 2012-05-09 | 2013-11-14 | Sasol Technology (Proprietary) Limited | Tetramerisation of ethylene |
WO2013168102A1 (en) | 2012-05-09 | 2013-11-14 | Sasol Technology (Proprietary) Limited | Tetramerisation of ethylene |
WO2013168099A1 (en) | 2012-05-09 | 2013-11-14 | Sasol Technology (Proprietary) Limited | A process for oligomerising a hydrocarbon to form at least one co-monomer product |
US8629280B2 (en) | 2007-01-08 | 2014-01-14 | Exxonmobil Chemical Patents Inc. | Methods for oligomerizing olefins with chromium pyridine ether catalysts |
US8637721B2 (en) | 2007-07-11 | 2014-01-28 | Saudi Basic Industries Corporation | Catalyst composition and process for di-, tri- and/or tetramerization of ethylene |
WO2014089479A1 (en) | 2012-12-07 | 2014-06-12 | Siluria Technologies, Inc. | Integrated processes and systems for conversion of methane to multiple higher hydrocarbon products |
US8865610B2 (en) | 2012-06-06 | 2014-10-21 | Chevron Phillips Chemical Company Lp | Phosphinyl guanidine compounds, metal salt complexes, catalyst systems, and their use to oligomerize or polymerize olefins |
WO2014181250A1 (en) | 2013-05-09 | 2014-11-13 | Sasol Technology (Proprietary) Limited | Tetramerisation of ethylene |
WO2014181247A1 (en) | 2013-05-09 | 2014-11-13 | Sasol Technology (Proprietary) Limited | Oligomerisation of ethylene to mixtures of 1-hexene and 1-octene |
WO2014181248A1 (en) | 2013-05-09 | 2014-11-13 | Sasol Technology (Proprietary) Limited | Oligomerisation of ethylene to mixtures of 1-hexene and 1-octene |
US8962903B2 (en) | 2010-10-06 | 2015-02-24 | Nova Chemicals (International) S.A. | Tetramerization ligands |
WO2015083053A1 (en) | 2013-12-05 | 2015-06-11 | Nova Chemicals (International) S.A. | Ethylene oligomerization with mixed ligands |
WO2015097599A1 (en) | 2013-12-23 | 2015-07-02 | Nova Chemicals (International) S.A. | Continuous ethylene oligomerization with in-situ catalyst preparation |
WO2015105911A1 (en) | 2014-01-08 | 2015-07-16 | Siluria Technologies, Inc. | Ethylene-to-liquids systems and methods |
US9133079B2 (en) | 2012-01-13 | 2015-09-15 | Siluria Technologies, Inc. | Process for separating hydrocarbon compounds |
US9283555B2 (en) | 2009-12-31 | 2016-03-15 | Chevron Phillips Chemical Company Lp | Phosphinyl amidine compounds, metal complexes, catalyst systems, and their use to oligomerize or polymerize olefins |
US9328297B1 (en) | 2015-06-16 | 2016-05-03 | Siluria Technologies, Inc. | Ethylene-to-liquids systems and methods |
US9334204B1 (en) | 2015-03-17 | 2016-05-10 | Siluria Technologies, Inc. | Efficient oxidative coupling of methane processes and systems |
US9352295B2 (en) | 2014-01-09 | 2016-05-31 | Siluria Technologies, Inc. | Oxidative coupling of methane implementations for olefin production |
US9375709B2 (en) | 2012-03-16 | 2016-06-28 | Sk Innovation Co., Ltd. | Catalyst systems for preparing 1-hexene and/or 1-octene from ethylene |
US9469577B2 (en) | 2012-05-24 | 2016-10-18 | Siluria Technologies, Inc. | Oxidative coupling of methane systems and methods |
CN106111200A (en) * | 2016-06-21 | 2016-11-16 | 东南大学 | Many metal corsslinkings for uns-dimethylhydrazine degraded coordinate catalyst and its preparation method and application |
WO2016205411A2 (en) | 2015-06-16 | 2016-12-22 | Siluria Technologies, Inc. | Ethylene-to-liquids systems and methods |
US9550841B2 (en) | 2004-02-20 | 2017-01-24 | Chevron Phillips Chemical Company Lp | Methods of preparation of an olefin oligomerization catalyst |
EP2987783A4 (en) * | 2013-11-18 | 2017-02-08 | LG Chem, Ltd. | Ligand compound, catalyst system for olefin oligomerization, and olefin oligomerization method using same |
US9586872B2 (en) | 2011-12-30 | 2017-03-07 | Chevron Phillips Chemical Company Lp | Olefin oligomerization methods |
KR20170028203A (en) | 2015-09-03 | 2017-03-13 | 한택규 | Process for selective oligomerization of Ethylene |
WO2017046701A1 (en) | 2015-09-16 | 2017-03-23 | Sabic Global Technologies B.V. | Process for deactivation of an olefin oligomerization catalyst |
US9637509B2 (en) | 2013-11-19 | 2017-05-02 | Lg Chem, Ltd. | Ligand compound, catalyst system for olefin oligomerization, and method for olefin oligomerization using the same |
US9670113B2 (en) | 2012-07-09 | 2017-06-06 | Siluria Technologies, Inc. | Natural gas processing and systems |
WO2017093940A1 (en) | 2015-12-04 | 2017-06-08 | Sabic Global Technologies B.V. | Process for flushing an oligomerization reactor and oligomerization of an olefin |
US9688588B2 (en) | 2012-12-21 | 2017-06-27 | Nova Chemicals (International) S.A. | Continuous ethylene tetramerization process |
WO2017163158A1 (en) | 2016-03-21 | 2017-09-28 | Sabic Global Technologies B.V. | Method for processing an oligomerization product stream |
WO2017187289A1 (en) | 2016-04-25 | 2017-11-02 | Sabic Global Technologies B.V. | Process for removing heat from an oligomerization reaction |
WO2017204476A1 (en) | 2016-05-27 | 2017-11-30 | 에스케이이노베이션 주식회사 | Oligomerizing catalyst and method for preparing ethylene oligomer using same |
FR3051683A1 (en) * | 2016-05-31 | 2017-12-01 | Ifp Energies Now | CHROMIUM-BASED CATALYTIC COMPOSITION AND PHOSPHINE-BASED LIGAND AND USE THEREOF IN PROCESS OF OCTENES |
WO2018012997A1 (en) * | 2016-07-15 | 2018-01-18 | Public Joint Stock Company "Sibur Holding" | Method of oligomerization of olefins |
US9944573B2 (en) | 2016-04-13 | 2018-04-17 | Siluria Technologies, Inc. | Oxidative coupling of methane for olefin production |
US9944661B2 (en) | 2016-08-09 | 2018-04-17 | Chevron Phillips Chemical Company Lp | Olefin hydroboration |
EP3208284A4 (en) * | 2015-09-02 | 2018-05-23 | LG Chem, Ltd. | Ligand compound, catalyst system for olefin oligomerization, and method for oligomerizing olefins using the same |
WO2018116176A1 (en) | 2016-12-22 | 2018-06-28 | Sabic Global Technologies B.V. | Methods of producing linear alpha olefins |
WO2018122779A1 (en) | 2016-12-30 | 2018-07-05 | Sabic Global Technologies B.V. | Methods of producing linear alpha olefins |
EP3214087A4 (en) * | 2015-10-21 | 2018-07-18 | LG Chem, Ltd. | Ligand compound, catalyst system for olefin oligomerization, and olefin oligomerization method using same |
US10047020B2 (en) | 2013-11-27 | 2018-08-14 | Siluria Technologies, Inc. | Reactors and systems for oxidative coupling of methane |
WO2018230846A1 (en) | 2017-06-16 | 2018-12-20 | 에스케이이노베이션 주식회사 | Heteroatom ligand, oligomerization catalyst containing same, and method for preparing oligomer |
US10160696B2 (en) | 2010-12-01 | 2018-12-25 | Nova Chemicals (International) S.A. | Heat management in ethylene oligomerization |
WO2019009390A1 (en) | 2017-07-06 | 2019-01-10 | 三井化学株式会社 | Catalyst for olefin multimerization and method for producing olefin multimer in presence of said catalyst |
US10183960B1 (en) | 2017-09-22 | 2019-01-22 | Chevron Phillips Chemical Company Lp | Perfluorohydrocarbyl-N2-phosphinyl amidine compounds, chromium salt complexes, catalyst systems, and their use to oligomerize ethylene |
EP3296329A4 (en) * | 2015-09-15 | 2019-03-06 | LG Chem, Ltd. | Olefin oligomerization method |
US10232339B2 (en) | 2017-06-06 | 2019-03-19 | Chevron Phillips Chemical Company Lp | Fouling protection for an oligomerization reactor inlet |
US10294171B2 (en) | 2017-09-22 | 2019-05-21 | Chevron Phillips Chemical Company Lp | Carbonyl-containing perfluorohydrocarbyl-N2-phosphinyl amidine compounds, chromium salt complexes and their use to oligomerize ethylene |
US10329212B2 (en) | 2016-05-27 | 2019-06-25 | Chevron Phillips Chemical Company Lp | Reduced polymer formation for selective ethylene oligomerizations |
US10377682B2 (en) | 2014-01-09 | 2019-08-13 | Siluria Technologies, Inc. | Reactors and systems for oxidative coupling of methane |
KR20190102970A (en) | 2018-02-27 | 2019-09-04 | 에스케이이노베이션 주식회사 | Ligand, Oligomerization Catalyst And Process For Preparing Ethylene Oligomer Using Thereof |
WO2019168249A1 (en) | 2018-02-27 | 2019-09-06 | 에스케이이노베이션 주식회사 | Ligand, oligomerization catalyst comprising same, and method for producing ethylene oligomer by using oligomerization catalyst |
US10414699B2 (en) | 2016-05-27 | 2019-09-17 | Chevron Phillips Chemical Company Lp | Process improvements in selective ethylene oligomerizations |
US10414698B2 (en) | 2016-05-27 | 2019-09-17 | Chevron Phillips Chemical Company Lp | Reduced polymer formation for selective ethylene oligomerizations |
US10421064B2 (en) | 2014-07-24 | 2019-09-24 | Sabic Global Technologies B.V. | Catalyst composition and process for oligomerization of ethylene to produce 1-hexene and/or 1-octene |
US10464862B2 (en) | 2017-09-28 | 2019-11-05 | Chevron Phillips Chemical Company Lp | Oligomerization reactions using aluminoxanes |
US10493442B2 (en) | 2017-09-22 | 2019-12-03 | Chevron Phillips Chemical Company Lp | Fluorinated N2-phosphinyl amidine compounds, chromium salt complexes, catalyst systems, and their use to oligomerize ethylene |
US10793490B2 (en) | 2015-03-17 | 2020-10-06 | Lummus Technology Llc | Oxidative coupling of methane methods and systems |
US10836689B2 (en) | 2017-07-07 | 2020-11-17 | Lummus Technology Llc | Systems and methods for the oxidative coupling of methane |
US10960343B2 (en) | 2016-12-19 | 2021-03-30 | Lummus Technology Llc | Methods and systems for performing chemical separations |
US11001543B2 (en) | 2015-10-16 | 2021-05-11 | Lummus Technology Llc | Separation methods and systems for oxidative coupling of methane |
US11001542B2 (en) | 2017-05-23 | 2021-05-11 | Lummus Technology Llc | Integration of oxidative coupling of methane processes |
US11186529B2 (en) | 2015-04-01 | 2021-11-30 | Lummus Technology Llc | Advanced oxidative coupling of methane |
FR3116739A1 (en) | 2020-11-30 | 2022-06-03 | IFP Energies Nouvelles | NEW CATALYTIC COMPOSITION BASED ON CHROME COMPRISING AN AROMATIC HYDROCARBON ADDITIVE AND ASSOCIATED METHOD FOR THE OLIGOMERIZATION OF ETHYLENE INTO OCTENE-1 |
FR3116738A1 (en) | 2020-11-30 | 2022-06-03 | IFP Energies Nouvelles | NEW CATALYTIC COMPOSITION BASED ON CHROMIUM COMPRISING AN AROMATIC ETHER ADDITIVE AND ASSOCIATED PROCESS FOR THE OLIGOMERIZATION OF ETHYLENE INTO OCTENE-1 |
US11492305B1 (en) | 2021-11-08 | 2022-11-08 | Chevron Phillips Chemical Company, Lp | Chromium phosphinyl hydroisoindole amidine complexes for tetramerization of ethylene |
US11505513B1 (en) | 2021-11-08 | 2022-11-22 | Chevron Phillips Chemical Company, Lp | Chromium bicyclic phosphinyl amidine complexes for tetramerization of ethylene |
US11583843B1 (en) | 2021-11-08 | 2023-02-21 | Chevron Phillips Chemical Company, Lp | Chromium phosphinyl isoindole amidine complexes for tetramerization of ethylene |
US11623901B1 (en) | 2022-08-31 | 2023-04-11 | Saudi Arabian Oil Company | Catalyst systems that include silyl ether moieties |
US11639321B1 (en) | 2022-08-31 | 2023-05-02 | Saudi Arabian Oil Company | Catalyst systems that include meta-alkoxy substituted n-aryl bis-diphosphinoamine ligands |
FR3128710A1 (en) | 2021-11-02 | 2023-05-05 | IFP Energies Nouvelles | Ethylene oligomerization process using a catalytic composition comprising a chromium precursor, a PNP type ligand and an aluminoxane |
EP2328905B2 (en) † | 2008-09-29 | 2023-05-31 | Nova Chemicals (International) S.A. | Ethylene tetramerization catalysts comprising p-n-p ligands |
FR3140775A1 (en) | 2022-10-17 | 2024-04-19 | IFP Energies Nouvelles | New catalytic composition based on supported chromium or titanium |
Families Citing this family (80)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2006218437A (en) * | 2005-02-14 | 2006-08-24 | Sumitomo Chemical Co Ltd | Trimerization catalyst of olefin and trimerization method of olefin using it |
JP4982952B2 (en) * | 2005-02-14 | 2012-07-25 | 住友化学株式会社 | Ethylene trimerization catalyst and ethylene trimerization method using the catalyst |
US7414006B2 (en) * | 2005-03-09 | 2008-08-19 | Exxonmobil Chemical Patents Inc. | Methods for oligomerizing olefins |
US7425661B2 (en) * | 2005-03-09 | 2008-09-16 | Exxonmobil Chemicals Patents Inc. | Methods for oligomerizing olefins |
US8874477B2 (en) | 2005-10-04 | 2014-10-28 | Steven Mark Hoffberg | Multifactorial optimization system and method |
US20070185357A1 (en) * | 2005-11-21 | 2007-08-09 | De Boer Eric J M | Catalytic process for the oligomerization of olefinic monomers |
US7982085B2 (en) * | 2006-02-03 | 2011-07-19 | Exxonmobil Chemical Patents Inc. | In-line process for generating comonomer |
US8076524B2 (en) | 2006-02-03 | 2011-12-13 | Exxonmobil Chemical Patents Inc. | Process for generating alpha olefin comonomers |
US8003839B2 (en) * | 2006-02-03 | 2011-08-23 | Exxonmobil Chemical Patents Inc. | Process for generating linear apha olefin comonomers |
CN100443178C (en) * | 2006-03-10 | 2008-12-17 | 中国石油天然气股份有限公司 | Catalyst composition for ethylene oligomerization and application thereof |
US8404915B2 (en) * | 2006-08-30 | 2013-03-26 | Exxonmobil Chemical Patents Inc. | Phosphine ligand-metal compositions, complexes, and catalysts for ethylene trimerizations |
KR101095796B1 (en) * | 2007-02-08 | 2011-12-21 | 에스케이종합화학 주식회사 | Ethylene Tetramerization Catalytst Systems for Immobilization and Process Using the Same |
JP4974732B2 (en) * | 2007-03-30 | 2012-07-11 | 三井化学株式会社 | Method for producing cyclic olefin |
JP2009072665A (en) * | 2007-09-19 | 2009-04-09 | Mitsui Chemicals Inc | Catalyst for olefin polymerization, and manufacturing method of ethylene polymer |
US8211949B2 (en) | 2007-09-24 | 2012-07-03 | Dow Global Technologies Llc | Functionalized long-chain olefin mixtures and uses therefor |
JP5462179B2 (en) * | 2007-11-28 | 2014-04-02 | リンデ アーゲー | Catalyst composition and process for oligomerization of ethylene |
JP5208870B2 (en) * | 2008-07-11 | 2013-06-12 | 三井化学株式会社 | Method for producing silylated polyolefin and additive containing silylated polyolefin |
CA2639870A1 (en) * | 2008-09-29 | 2010-03-29 | Nova Chemicals Corporation | Trimerization |
KR101065596B1 (en) * | 2009-01-29 | 2011-09-19 | 에스케이종합화학 주식회사 | High Active and High Selective Ethylene Oligomerization Catalyst, and process for preparing hexene or octene using thereof |
CN102107146B (en) * | 2009-12-29 | 2013-10-16 | 中国石油天然气股份有限公司 | Catalyst for synthesizing hexene-1 by ethylene trimerization and application thereof |
ES2409707T3 (en) | 2011-02-16 | 2013-06-27 | Linde Ag | Process for preparing a catalytic composition for oligomerization of ethylene and preforming unit of respective catalyst composition |
RU2470707C1 (en) * | 2011-06-27 | 2012-12-27 | Общество с ограниченной ответственностью "Объединенный центр исследований и разработок" | Catalyst for trimerisation of ethylene to 1-hexene, ligand for producing catalyst, method of producing catalyst and method of producing ligand |
JP5844636B2 (en) | 2011-12-27 | 2016-01-20 | 出光興産株式会社 | Method for producing α-olefin |
KR101483248B1 (en) * | 2012-11-15 | 2015-01-16 | 주식회사 엘지화학 | Ligand compound, organic chromium compound, catalyst system for ethylene oligomerization, method for preparign the same, and method for ethylene oligomerization using the same |
EP2962756A4 (en) * | 2013-02-27 | 2016-11-02 | Mitsui Chemicals Inc | Catalyst for olefin multimerization and method for producing olefin multimer in presence of catalyst for olefin multimerization |
CN104059105B (en) * | 2013-03-20 | 2016-06-29 | 中国石油化工股份有限公司 | Ligand compound containing pyridine radicals, the catalyst containing this compound and application thereof |
FR3007761B1 (en) * | 2013-06-28 | 2016-02-05 | IFP Energies Nouvelles | NEW NICKEL COMPLEX AND USE THEREOF IN OLEFIN OLIGOMERIZATION PROCESS |
EP2832445A1 (en) * | 2013-07-29 | 2015-02-04 | Linde AG | Catalyst composition and process for oligomerization of ethylene |
CN104415790B (en) * | 2013-08-23 | 2017-06-30 | 中国石油化工股份有限公司 | A kind of catalyst for ethylene tetramerization composition and application |
KR101676835B1 (en) | 2013-11-18 | 2016-11-17 | 주식회사 엘지화학 | Ligand compound, catalyst system for olefin oligomerization, and method for olefin oligomerization using the same |
KR20150058034A (en) * | 2013-11-18 | 2015-05-28 | 주식회사 엘지화학 | Ligand compound, catalyst system for olefin oligomerization, and method for olefin oligomerization using the same |
ES2841381T3 (en) | 2014-02-03 | 2021-07-08 | Saudi Basic Ind Corp | Preforming unit of a catalyst composition for preparing a catalyst composition for the oligomerization of ethylene |
US9175109B1 (en) | 2014-05-20 | 2015-11-03 | Chevron Phillips Chemical Company Lp | Oligomerization processes and polymer compositions produced therefrom |
CN106164103B (en) * | 2014-06-18 | 2018-05-25 | 株式会社Lg化学 | Ligand compound, organo-chromium compound, the catalyst system for olefin oligomerization and the method for olefin oligomerization using the catalyst system |
CN105562098B (en) * | 2014-10-08 | 2018-03-02 | 中国石油化工股份有限公司 | A kind of ethylene oligomerisation catalyst composition and its application |
CN105562099B (en) * | 2014-10-08 | 2018-01-23 | 中国石油化工股份有限公司 | A kind of catalyst for ethylene tetramerization composition and ethylene tetramerization method |
CN105566036B (en) * | 2014-10-13 | 2018-05-11 | 中国石油化工股份有限公司 | A kind of method of ethylene tetramerization |
JP6488638B2 (en) * | 2014-10-28 | 2019-03-27 | セントラル硝子株式会社 | Method for producing α-fluoroaldehyde equivalents |
EP3237363B1 (en) * | 2014-12-23 | 2019-05-01 | Public Joint Stock Company "Sibur Holding" | Methods of preparing oligomers of an olefin |
MX369759B (en) * | 2015-01-19 | 2019-11-20 | Evonik Operations Gmbh | Combined preparation of butene and octene from ethene. |
US9505675B2 (en) | 2015-02-09 | 2016-11-29 | Chevron Phillips Chemical Company Lp | Deactivation of a process by-product |
KR101679515B1 (en) | 2015-02-12 | 2016-11-24 | 주식회사 엘지화학 | Method of preparing catalyst system for oligomerization and catalyst sysyem for oligomerization prepared thereby |
US10357764B2 (en) * | 2015-03-13 | 2019-07-23 | Dow Global Technologies Llc | Phosphacycle compound and process for production thereof |
KR101761395B1 (en) | 2015-04-15 | 2017-07-25 | 주식회사 엘지화학 | Ligand compound, catalyst system for oligomerization, and method for olefin oligomerization using the same |
US10513474B2 (en) | 2015-05-15 | 2019-12-24 | Lg Chem, Ltd. | Catalyst composition and method of preparing polyolefin using the same |
KR20160134464A (en) | 2015-05-15 | 2016-11-23 | 주식회사 엘지화학 | Supported hybrid catalyst system and method for olefin polymerization using the same |
KR101768194B1 (en) * | 2015-05-15 | 2017-08-16 | 주식회사 엘지화학 | Catalyst composition and method for preparing polyolefin using the same |
KR101757370B1 (en) * | 2015-06-01 | 2017-07-12 | 주식회사 엘지화학 | 1-Octene composition |
KR101757835B1 (en) * | 2015-06-12 | 2017-07-13 | 주식회사 엘지화학 | Ligand compound, organic chromium compound, catalyst system for oligomerization of olefins and method for oligomerization of olefins using the catalyst system |
WO2017010998A1 (en) | 2015-07-14 | 2017-01-19 | Chevron Phillips Chemical Company Lp | Olefin compositions |
US9732300B2 (en) | 2015-07-23 | 2017-08-15 | Chevron Phillipa Chemical Company LP | Liquid propylene oligomers and methods of making same |
US10513473B2 (en) | 2015-09-18 | 2019-12-24 | Chevron Phillips Chemical Company Lp | Ethylene oligomerization/trimerization/tetramerization reactor |
US10519077B2 (en) | 2015-09-18 | 2019-12-31 | Chevron Phillips Chemical Company Lp | Ethylene oligomerization/trimerization/tetramerization reactor |
KR101735687B1 (en) | 2015-09-23 | 2017-05-15 | 롯데케미칼 주식회사 | Catalyst system for olefin oligomerization, and method for olefin oligomerization using the same |
CN105289742B (en) * | 2015-11-11 | 2018-07-13 | 天津科技大学 | For the catalyst of ethylene selectivity oligomerisation, ligand and preparation method thereof |
BR112018017060B1 (en) * | 2016-03-22 | 2022-09-06 | Apalene Technology Co., Ltd. (Hangzhou) | LINEAR POLY-ALPHA-OLEFIN CATALYST AND PREPARATION METHOD THEREOF |
KR102428767B1 (en) | 2016-07-14 | 2022-08-04 | 에스케이이노베이션 주식회사 | Oligomerisation of ethylene |
WO2018012792A1 (en) | 2016-07-14 | 2018-01-18 | Sk Innovation Co., Ltd. | Oligomerization of ethylene |
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JP7402241B2 (en) | 2019-01-15 | 2023-12-20 | 中国石油化工股▲ふん▼有限公司 | Halogen-containing compounds and uses, and ethylene oligomerization catalyst compositions and ethylene oligomerization methods, ethylene trimerization methods, and ethylene tetramerization methods |
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WO2020185426A1 (en) | 2019-03-13 | 2020-09-17 | Tpc Group Llc | Flexible manufacturing system for selectively producing different linear alpha olefins |
FR3108264B1 (en) | 2020-03-19 | 2022-04-08 | Ifp Energies Now | Ethylene oligomerization plant to produce alpha-olefins |
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KR102631413B1 (en) | 2021-06-15 | 2024-01-31 | 한화토탈에너지스 주식회사 | Method for ethylene oligomerization |
KR20230027512A (en) | 2021-08-19 | 2023-02-28 | 에스케이이노베이션 주식회사 | Chromium catalyst precursors, ethylene oligomerization catalyst comprising the same and process for preparing ethylene oligomer |
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WO2023177129A1 (en) * | 2022-03-14 | 2023-09-21 | 주식회사 엘지화학 | Ligand compound, organic chromium compound and catalyst composition comprising same |
CN115124575B (en) * | 2022-06-23 | 2024-02-27 | 中国五环工程有限公司 | Preparation method of PNP ligand structure Cr (III) metal catalyst |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2699457A (en) * | 1950-06-21 | 1955-01-11 | Ziegler Karl | Polymerization of ethylene |
US4628138A (en) * | 1985-09-20 | 1986-12-09 | Ashland Oil, Inc. | Catalyst and process for oligomerization of ethylene |
WO2002004119A1 (en) * | 2000-07-11 | 2002-01-17 | Bp Chemicals Limited | Olefin trimerisation using a catalyst comprising a source of chromium, molybdenum or tungsten and a ligand containing at least one phosphorous, arsenic or antimony atom bound to at least one (hetero)hydrocarbyl group |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1020563A (en) | 1961-11-21 | 1966-02-23 | Gulf Research Development Co | Process for polymerizing ethylene |
US3635937A (en) | 1969-11-05 | 1972-01-18 | Shell Oil Co | Ethylene polymerization |
US3676523A (en) | 1971-07-16 | 1972-07-11 | Shell Oil Co | Alpha-olefin production |
US3906053A (en) | 1971-08-10 | 1975-09-16 | Ethyl Corp | Process for the production of olefins |
JPH07215896A (en) * | 1994-02-04 | 1995-08-15 | Idemitsu Kosan Co Ltd | Production of alpha-olefin oligomer |
JPH09143228A (en) * | 1995-11-22 | 1997-06-03 | Sumitomo Chem Co Ltd | Production of ethylene/alpha-olefin copolymer |
US6184428B1 (en) | 1998-04-22 | 2001-02-06 | Saudi Basic Industries Corporation | Catalyst and process for ethylene oligomerization |
GB9918635D0 (en) * | 1999-08-06 | 1999-10-13 | Bp Chem Int Ltd | Polymerisation process |
CN1308269C (en) | 2001-12-20 | 2007-04-04 | Sasol技术股份有限公司 | Trimerisation and oligomerisation of olefins using a chromium based catalyst |
-
2003
- 2003-12-19 PL PL377406A patent/PL377406A1/en not_active Application Discontinuation
- 2003-12-19 PL PL377488A patent/PL377488A1/en not_active Application Discontinuation
- 2003-12-19 CA CA2510194A patent/CA2510194C/en not_active Expired - Lifetime
- 2003-12-19 EP EP03813852A patent/EP1581341B1/en not_active Expired - Lifetime
- 2003-12-19 CN CNB2003801091332A patent/CN100540514C/en not_active Expired - Lifetime
- 2003-12-19 US US10/539,517 patent/US7511183B2/en not_active Expired - Lifetime
- 2003-12-19 CA CA2510801A patent/CA2510801C/en not_active Expired - Lifetime
- 2003-12-19 PL PL377211A patent/PL377211A1/en not_active Application Discontinuation
- 2003-12-19 CN CNB2003801091309A patent/CN100548947C/en not_active Expired - Lifetime
- 2003-12-19 CA CA2510190A patent/CA2510190C/en not_active Expired - Lifetime
- 2003-12-19 CN CNB2003801091277A patent/CN100548946C/en not_active Expired - Lifetime
- 2003-12-19 DE DE60331252T patent/DE60331252D1/en not_active Expired - Lifetime
- 2003-12-19 JP JP2005511967A patent/JP2006516265A/en not_active Withdrawn
- 2003-12-19 AT AT03813852T patent/ATE457196T1/en not_active IP Right Cessation
- 2003-12-19 AU AU2003297545A patent/AU2003297545A1/en not_active Abandoned
- 2003-12-19 AU AU2003297546A patent/AU2003297546A1/en not_active Abandoned
- 2003-12-19 BR BR0317516-2A patent/BR0317516A/en not_active IP Right Cessation
- 2003-12-19 ES ES03813852T patent/ES2340483T3/en not_active Expired - Lifetime
- 2003-12-19 BR BRPI0317510-3A patent/BRPI0317510B1/en unknown
- 2003-12-19 WO PCT/ZA2003/000186 patent/WO2004056478A1/en active Application Filing
- 2003-12-19 EP EP03813854A patent/EP1581342B1/en not_active Expired - Lifetime
- 2003-12-19 AT AT03813853T patent/ATE477053T1/en not_active IP Right Cessation
- 2003-12-19 JP JP2005511969A patent/JP2006517528A/en not_active Withdrawn
- 2003-12-19 KR KR1020057011608A patent/KR20060002742A/en not_active Application Discontinuation
- 2003-12-19 BR BR0317510-3A patent/BR0317510A/en active IP Right Grant
- 2003-12-19 BR BR0316870-0A patent/BR0316870A/en active IP Right Grant
- 2003-12-19 EP EP03813853A patent/EP1578531B9/en not_active Expired - Lifetime
- 2003-12-19 WO PCT/ZA2003/000187 patent/WO2004056479A1/en active Application Filing
- 2003-12-19 KR KR1020057011604A patent/KR20050100600A/en not_active Application Discontinuation
- 2003-12-19 KR KR1020057011601A patent/KR20060002741A/en not_active Application Discontinuation
- 2003-12-19 WO PCT/ZA2003/000185 patent/WO2004056477A1/en active Application Filing
- 2003-12-19 AU AU2003297544A patent/AU2003297544A1/en not_active Abandoned
- 2003-12-19 BR BRPI0316870-0A patent/BRPI0316870B1/en unknown
- 2003-12-19 BR BRPI0317516A patent/BRPI0317516B1/en unknown
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2699457A (en) * | 1950-06-21 | 1955-01-11 | Ziegler Karl | Polymerization of ethylene |
US4628138A (en) * | 1985-09-20 | 1986-12-09 | Ashland Oil, Inc. | Catalyst and process for oligomerization of ethylene |
WO2002004119A1 (en) * | 2000-07-11 | 2002-01-17 | Bp Chemicals Limited | Olefin trimerisation using a catalyst comprising a source of chromium, molybdenum or tungsten and a ligand containing at least one phosphorous, arsenic or antimony atom bound to at least one (hetero)hydrocarbyl group |
Non-Patent Citations (1)
Title |
---|
ANTHEA CARTER, STEVEN COHEN, NEIL COOLEY, ADEN MURPHY, JAMES SCUTT, DUNAN WASS: "High activity ethylene trimerization catalysts based on diphosphine ligands", CHEMICAL COMMUNICATION, vol. 2002, no. 8, 20 March 2002 (2002-03-20), pages 858 - 859, XP002277009 * |
Cited By (230)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7273959B2 (en) | 2003-10-10 | 2007-09-25 | Shell Oil Company | Catalytic trimerization of olefinic monomers |
US7994376B2 (en) | 2004-02-19 | 2011-08-09 | Chevron Phillips Chemical Company Lp | Olefin oligomerization |
US8329608B2 (en) | 2004-02-20 | 2012-12-11 | Chevron Phillips Chemical Company Lp | Methods of preparation of an olefin oligomerization catalyst |
US7820581B2 (en) | 2004-02-20 | 2010-10-26 | Chevron Phillips Chemical Company Lp | Methods of preparation of an olefin oligomerization catalyst |
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WO2005123884A3 (en) * | 2004-06-18 | 2006-05-18 | Sasol Tech Pty Ltd | Oligomerisation in the presence of both a tetramerisation catalyst and a further oligomerisation catalyst |
WO2005123884A2 (en) * | 2004-06-18 | 2005-12-29 | Sasol Technology (Pty) Limited | Oligomerisation in the presence of both a tetramerisation catalyst and a further oligomerisation catalyst |
US7964763B2 (en) | 2004-06-18 | 2011-06-21 | Sasol Technology (Pty) Limited | Oligomerisation of olefinic compounds in an aliphatic medium |
US8076523B2 (en) | 2004-06-18 | 2011-12-13 | Sasol Technology (Pty) Limited | Oligomerisation in the presence of both a tetramerisation catalyst and a further oligomerisation catalyst |
US7381857B2 (en) | 2005-04-08 | 2008-06-03 | Shell Oil Company | Catalytic trimerization and tetramerization of olefinic monomers |
US7259123B2 (en) | 2005-04-08 | 2007-08-21 | Shell Oil Company | Catalytic trimerization and tetramerization of olefinic monomers |
JP2007039641A (en) * | 2005-06-28 | 2007-02-15 | Sumitomo Chemical Co Ltd | Method for producing olefin oligomer |
US7323611B2 (en) | 2005-06-28 | 2008-01-29 | Sumitomo Chemical Company Limited | Process for producing olefin oligomer |
WO2007007272A2 (en) | 2005-07-12 | 2007-01-18 | Sasol Technology (Pty) Limited | Oligomerisation of olefinic compounds in the presence of a diluted metal containing activator |
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US7550639B2 (en) | 2005-07-27 | 2009-06-23 | Sumitomo Chemical Company, Limited | Process for producing olefin oligomer |
JP2007056002A (en) * | 2005-07-27 | 2007-03-08 | Sumitomo Chemical Co Ltd | Method for producing olefin oligomer |
US7910670B2 (en) | 2005-08-19 | 2011-03-22 | Chevron Phillips Chemical Company Lp | Methods of preparation of an olefin oligomerization catalyst |
US8134038B2 (en) | 2005-10-03 | 2012-03-13 | Sasol Technology (Pty) Limited | Oligomerisation of olefinic compounds in the presence of an oligomerisation catalyst, and a catalyst activator including a halogenated organic group |
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US7858833B2 (en) | 2006-02-03 | 2010-12-28 | Exxonmobil Chemical Patents Inc. | Process for generating linear alpha olefin comonomers |
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US7687672B2 (en) | 2006-02-03 | 2010-03-30 | Exxonmobil Chemical Patents Inc. | In-line process for generating comonomer |
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US8067654B2 (en) | 2006-02-03 | 2011-11-29 | Ineos Europe Limited | Transition metal catalysts |
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US8252874B2 (en) | 2006-12-22 | 2012-08-28 | Shell Oil Company | Ligands and catalyst systems for the oligomerization of olefinic monomers |
US7803886B2 (en) | 2006-12-22 | 2010-09-28 | Shell Oil Company | Ligands and catalyst systems thereof for the catalytic oligomerization of olefinic monomers |
US8067609B2 (en) | 2007-01-08 | 2011-11-29 | Exxonmobil Chemical Patents Inc. | Methods for oligomerizing olefins with chromium pyridine thioether catalysts |
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US7994363B2 (en) | 2007-03-29 | 2011-08-09 | Nova Chemicals (International) S.A | Amino phosphine |
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US8367786B2 (en) | 2007-05-28 | 2013-02-05 | Sasol Technology (Pty) Limited | Two stage activation of oligomerisation catalyst and oligomerisation of olefinic compounds in the presence of an oligomerisation catalyst so activated |
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US7902415B2 (en) | 2007-12-21 | 2011-03-08 | Chevron Phillips Chemical Company Lp | Processes for dimerizing or isomerizing olefins |
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WO2011098160A1 (en) | 2010-02-12 | 2011-08-18 | Enantia, S.L. | Enantiomerically enriched aminodiphosphines as ligands for the preparation of catalysts for asymmetric synthesis |
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WO2011108772A1 (en) | 2010-03-03 | 2011-09-09 | 에스케이이노베이션 주식회사 | Highly active and highly selective ethylene oligomerization catalyst, and preparation method of hexene or octene using same |
WO2011140629A1 (en) * | 2010-05-12 | 2011-11-17 | Nova Chemicals (International) S.A. | Oligomenzation of alpha olefins |
US8962903B2 (en) | 2010-10-06 | 2015-02-24 | Nova Chemicals (International) S.A. | Tetramerization ligands |
WO2012055943A2 (en) | 2010-10-28 | 2012-05-03 | Basell Polyolefine Gmbh | Oligomerization of olefins |
US10160696B2 (en) | 2010-12-01 | 2018-12-25 | Nova Chemicals (International) S.A. | Heat management in ethylene oligomerization |
US9586872B2 (en) | 2011-12-30 | 2017-03-07 | Chevron Phillips Chemical Company Lp | Olefin oligomerization methods |
US9133079B2 (en) | 2012-01-13 | 2015-09-15 | Siluria Technologies, Inc. | Process for separating hydrocarbon compounds |
US9527784B2 (en) | 2012-01-13 | 2016-12-27 | Siluria Technologies, Inc. | Process for separating hydrocarbon compounds |
US11254626B2 (en) | 2012-01-13 | 2022-02-22 | Lummus Technology Llc | Process for separating hydrocarbon compounds |
WO2013110170A1 (en) | 2012-01-25 | 2013-08-01 | Nova Chemicals (International) S.A. | P-n-p ligand |
US9375709B2 (en) | 2012-03-16 | 2016-06-28 | Sk Innovation Co., Ltd. | Catalyst systems for preparing 1-hexene and/or 1-octene from ethylene |
US9399179B2 (en) | 2012-05-09 | 2016-07-26 | Sasol Technology Proprietary Limited | Separation of components from a multi-component hydrocarbon stream |
WO2013168099A1 (en) | 2012-05-09 | 2013-11-14 | Sasol Technology (Proprietary) Limited | A process for oligomerising a hydrocarbon to form at least one co-monomer product |
WO2013168103A1 (en) | 2012-05-09 | 2013-11-14 | Sasol Technology (Proprietary) Limited | Oligomerisation of olefinic compounds with reduced polymer formation |
WO2013168098A1 (en) | 2012-05-09 | 2013-11-14 | Sasol Technology (Proprietary) Limited | Separation of components from a multi-component hydrocarbon stream |
WO2013168106A1 (en) | 2012-05-09 | 2013-11-14 | Sasol Technology (Proprietary) Limited | Tetramerisation of ethylene |
WO2013168102A1 (en) | 2012-05-09 | 2013-11-14 | Sasol Technology (Proprietary) Limited | Tetramerisation of ethylene |
US9556086B2 (en) | 2012-05-24 | 2017-01-31 | Siluria Technologies, Inc. | Oxidative coupling of methane systems and methods |
US9469577B2 (en) | 2012-05-24 | 2016-10-18 | Siluria Technologies, Inc. | Oxidative coupling of methane systems and methods |
US8865610B2 (en) | 2012-06-06 | 2014-10-21 | Chevron Phillips Chemical Company Lp | Phosphinyl guanidine compounds, metal salt complexes, catalyst systems, and their use to oligomerize or polymerize olefins |
US9670113B2 (en) | 2012-07-09 | 2017-06-06 | Siluria Technologies, Inc. | Natural gas processing and systems |
US9969660B2 (en) | 2012-07-09 | 2018-05-15 | Siluria Technologies, Inc. | Natural gas processing and systems |
US11242298B2 (en) | 2012-07-09 | 2022-02-08 | Lummus Technology Llc | Natural gas processing and systems |
US9598328B2 (en) | 2012-12-07 | 2017-03-21 | Siluria Technologies, Inc. | Integrated processes and systems for conversion of methane to multiple higher hydrocarbon products |
US11168038B2 (en) | 2012-12-07 | 2021-11-09 | Lummus Technology Llc | Integrated processes and systems for conversion of methane to multiple higher hydrocarbon products |
WO2014089479A1 (en) | 2012-12-07 | 2014-06-12 | Siluria Technologies, Inc. | Integrated processes and systems for conversion of methane to multiple higher hydrocarbon products |
US10183900B2 (en) | 2012-12-07 | 2019-01-22 | Siluria Technologies, Inc. | Integrated processes and systems for conversion of methane to multiple higher hydrocarbon products |
US10787398B2 (en) | 2012-12-07 | 2020-09-29 | Lummus Technology Llc | Integrated processes and systems for conversion of methane to multiple higher hydrocarbon products |
US9688588B2 (en) | 2012-12-21 | 2017-06-27 | Nova Chemicals (International) S.A. | Continuous ethylene tetramerization process |
KR20210042426A (en) * | 2013-05-09 | 2021-04-19 | 사솔 테크날러지 (프로프라이어터리) 리미티드 | Tetramerisation of ethylene |
CN105228973A (en) * | 2013-05-09 | 2016-01-06 | 沙索技术有限公司 | Ethylene oligomerization becomes the oligomerization process of the mixture of 1-hexene and 1-octene |
US9533922B2 (en) | 2013-05-09 | 2017-01-03 | Sasol Technology (Proprietary) Limited | Oligomerisation of ethylene to mixtures of 1-hexene and 1-octene |
WO2014181250A1 (en) | 2013-05-09 | 2014-11-13 | Sasol Technology (Proprietary) Limited | Tetramerisation of ethylene |
KR20210043725A (en) * | 2013-05-09 | 2021-04-21 | 사솔 테크날러지 (프로프라이어터리) 리미티드 | Oligomerisation of ethylene to mixtures of 1-hexene and 1-octene |
KR102368171B1 (en) | 2013-05-09 | 2022-02-28 | 사솔 테크날러지 (프로프라이어터리) 리미티드 | Tetramerisation of ethylene |
WO2014181247A1 (en) | 2013-05-09 | 2014-11-13 | Sasol Technology (Proprietary) Limited | Oligomerisation of ethylene to mixtures of 1-hexene and 1-octene |
KR102369168B1 (en) | 2013-05-09 | 2022-03-02 | 사솔 테크날러지 (프로프라이어터리) 리미티드 | Oligomerisation of ethylene to mixtures of 1-hexene and 1-octene |
WO2014181248A1 (en) | 2013-05-09 | 2014-11-13 | Sasol Technology (Proprietary) Limited | Oligomerisation of ethylene to mixtures of 1-hexene and 1-octene |
US9546117B2 (en) | 2013-05-09 | 2017-01-17 | Sasol Technology (Proprietary) Limited | Tetramerisation of ethylene |
US9637508B2 (en) | 2013-11-18 | 2017-05-02 | Lg Chem, Ltd. | Ligand compound, catalyst system for olefin oligomerization, and method for olefin oligomerization using the same |
EP2987783A4 (en) * | 2013-11-18 | 2017-02-08 | LG Chem, Ltd. | Ligand compound, catalyst system for olefin oligomerization, and olefin oligomerization method using same |
US9637509B2 (en) | 2013-11-19 | 2017-05-02 | Lg Chem, Ltd. | Ligand compound, catalyst system for olefin oligomerization, and method for olefin oligomerization using the same |
US11407695B2 (en) | 2013-11-27 | 2022-08-09 | Lummus Technology Llc | Reactors and systems for oxidative coupling of methane |
US10927056B2 (en) | 2013-11-27 | 2021-02-23 | Lummus Technology Llc | Reactors and systems for oxidative coupling of methane |
US10047020B2 (en) | 2013-11-27 | 2018-08-14 | Siluria Technologies, Inc. | Reactors and systems for oxidative coupling of methane |
WO2015083053A1 (en) | 2013-12-05 | 2015-06-11 | Nova Chemicals (International) S.A. | Ethylene oligomerization with mixed ligands |
US10343152B2 (en) | 2013-12-23 | 2019-07-09 | Nova Chemicals (International) S.A. | Continuous ethylene oligomerization with in-situ catalyst preparation |
WO2015097599A1 (en) | 2013-12-23 | 2015-07-02 | Nova Chemicals (International) S.A. | Continuous ethylene oligomerization with in-situ catalyst preparation |
US9512047B2 (en) | 2014-01-08 | 2016-12-06 | Siluria Technologies, Inc. | Ethylene-to-liquids systems and methods |
US9321703B2 (en) | 2014-01-08 | 2016-04-26 | Siluria Technologies, Inc. | Ethylene-to-liquids systems and methods |
WO2015105911A1 (en) | 2014-01-08 | 2015-07-16 | Siluria Technologies, Inc. | Ethylene-to-liquids systems and methods |
US10894751B2 (en) | 2014-01-08 | 2021-01-19 | Lummus Technology Llc | Ethylene-to-liquids systems and methods |
US11254627B2 (en) | 2014-01-08 | 2022-02-22 | Lummus Technology Llc | Ethylene-to-liquids systems and methods |
US9321702B2 (en) | 2014-01-08 | 2016-04-26 | Siluria Technologies, Inc. | Ethylene-to-liquids systems and methods |
US9701597B2 (en) | 2014-01-09 | 2017-07-11 | Siluria Technologies, Inc. | Oxidative coupling of methane implementations for olefin production |
US9352295B2 (en) | 2014-01-09 | 2016-05-31 | Siluria Technologies, Inc. | Oxidative coupling of methane implementations for olefin production |
US10377682B2 (en) | 2014-01-09 | 2019-08-13 | Siluria Technologies, Inc. | Reactors and systems for oxidative coupling of methane |
US11008265B2 (en) | 2014-01-09 | 2021-05-18 | Lummus Technology Llc | Reactors and systems for oxidative coupling of methane |
US11208364B2 (en) | 2014-01-09 | 2021-12-28 | Lummus Technology Llc | Oxidative coupling of methane implementations for olefin production |
US10829424B2 (en) | 2014-01-09 | 2020-11-10 | Lummus Technology Llc | Oxidative coupling of methane implementations for olefin production |
US10421064B2 (en) | 2014-07-24 | 2019-09-24 | Sabic Global Technologies B.V. | Catalyst composition and process for oligomerization of ethylene to produce 1-hexene and/or 1-octene |
US10787400B2 (en) | 2015-03-17 | 2020-09-29 | Lummus Technology Llc | Efficient oxidative coupling of methane processes and systems |
US9334204B1 (en) | 2015-03-17 | 2016-05-10 | Siluria Technologies, Inc. | Efficient oxidative coupling of methane processes and systems |
US9790144B2 (en) | 2015-03-17 | 2017-10-17 | Siluria Technologies, Inc. | Efficient oxidative coupling of methane processes and systems |
US10793490B2 (en) | 2015-03-17 | 2020-10-06 | Lummus Technology Llc | Oxidative coupling of methane methods and systems |
US11542214B2 (en) | 2015-03-17 | 2023-01-03 | Lummus Technology Llc | Oxidative coupling of methane methods and systems |
US9567269B2 (en) | 2015-03-17 | 2017-02-14 | Siluria Technologies, Inc. | Efficient oxidative coupling of methane processes and systems |
US11186529B2 (en) | 2015-04-01 | 2021-11-30 | Lummus Technology Llc | Advanced oxidative coupling of methane |
WO2016205411A2 (en) | 2015-06-16 | 2016-12-22 | Siluria Technologies, Inc. | Ethylene-to-liquids systems and methods |
US10865165B2 (en) | 2015-06-16 | 2020-12-15 | Lummus Technology Llc | Ethylene-to-liquids systems and methods |
US9328297B1 (en) | 2015-06-16 | 2016-05-03 | Siluria Technologies, Inc. | Ethylene-to-liquids systems and methods |
US10131723B2 (en) | 2015-09-02 | 2018-11-20 | Lg Chem, Ltd. | Ligand compound, catalyst system for olefin oligomerization, and method for oligomerizing olefins using the same |
EP3208284A4 (en) * | 2015-09-02 | 2018-05-23 | LG Chem, Ltd. | Ligand compound, catalyst system for olefin oligomerization, and method for oligomerizing olefins using the same |
US10399912B2 (en) | 2015-09-03 | 2019-09-03 | Taek Kyu Han | Selective oligomerization reaction process of ethylene |
KR20170028203A (en) | 2015-09-03 | 2017-03-13 | 한택규 | Process for selective oligomerization of Ethylene |
EP3296329A4 (en) * | 2015-09-15 | 2019-03-06 | LG Chem, Ltd. | Olefin oligomerization method |
US10407359B2 (en) | 2015-09-16 | 2019-09-10 | Sabic Global Technologies B.V. | Process for deactivation of an olefin oligomerization catalyst |
WO2017046701A1 (en) | 2015-09-16 | 2017-03-23 | Sabic Global Technologies B.V. | Process for deactivation of an olefin oligomerization catalyst |
US11001543B2 (en) | 2015-10-16 | 2021-05-11 | Lummus Technology Llc | Separation methods and systems for oxidative coupling of methane |
EP3214087A4 (en) * | 2015-10-21 | 2018-07-18 | LG Chem, Ltd. | Ligand compound, catalyst system for olefin oligomerization, and olefin oligomerization method using same |
US10287373B2 (en) | 2015-10-21 | 2019-05-14 | Lg Chem, Ltd. | Ligand compound, catalyst system for olefin oligomerization, and method for oligomerizing olefins using the same |
WO2017093940A1 (en) | 2015-12-04 | 2017-06-08 | Sabic Global Technologies B.V. | Process for flushing an oligomerization reactor and oligomerization of an olefin |
WO2017163158A1 (en) | 2016-03-21 | 2017-09-28 | Sabic Global Technologies B.V. | Method for processing an oligomerization product stream |
US10758881B2 (en) | 2016-03-21 | 2020-09-01 | Sabic Global Technologies B.V. | Method for processing an oligomerization product stream |
US10870611B2 (en) | 2016-04-13 | 2020-12-22 | Lummus Technology Llc | Oxidative coupling of methane for olefin production |
US10407361B2 (en) | 2016-04-13 | 2019-09-10 | Siluria Technologies, Inc. | Oxidative coupling of methane for olefin production |
US9944573B2 (en) | 2016-04-13 | 2018-04-17 | Siluria Technologies, Inc. | Oxidative coupling of methane for olefin production |
US11505514B2 (en) | 2016-04-13 | 2022-11-22 | Lummus Technology Llc | Oxidative coupling of methane for olefin production |
WO2017187289A1 (en) | 2016-04-25 | 2017-11-02 | Sabic Global Technologies B.V. | Process for removing heat from an oligomerization reaction |
US11235315B2 (en) | 2016-05-27 | 2022-02-01 | Sk Innovation Co., Ltd. | Oligomerization catalyst and method for preparing ethylene oligomer using same |
WO2017204476A1 (en) | 2016-05-27 | 2017-11-30 | 에스케이이노베이션 주식회사 | Oligomerizing catalyst and method for preparing ethylene oligomer using same |
US10414699B2 (en) | 2016-05-27 | 2019-09-17 | Chevron Phillips Chemical Company Lp | Process improvements in selective ethylene oligomerizations |
US10689312B2 (en) | 2016-05-27 | 2020-06-23 | Chevron Phillip Chemical Company, LP | Process improvements in selective ethylene oligomerizations |
US10689311B2 (en) | 2016-05-27 | 2020-06-23 | Chevron Phillips Chemical Company, Lp | Reduced polymer formation for selective ethylene oligomerizations |
KR20170134045A (en) | 2016-05-27 | 2017-12-06 | 에스케이이노베이션 주식회사 | Oligomerization Catalyst And Process For Preparing Ethylene Oligomer Using Thereof |
US10774015B2 (en) | 2016-05-27 | 2020-09-15 | Chevron Phillips Chemical Company Lp | Reduced polymer formation for selective ethylene oligomerizations |
US10329212B2 (en) | 2016-05-27 | 2019-06-25 | Chevron Phillips Chemical Company Lp | Reduced polymer formation for selective ethylene oligomerizations |
US10414698B2 (en) | 2016-05-27 | 2019-09-17 | Chevron Phillips Chemical Company Lp | Reduced polymer formation for selective ethylene oligomerizations |
FR3051683A1 (en) * | 2016-05-31 | 2017-12-01 | Ifp Energies Now | CHROMIUM-BASED CATALYTIC COMPOSITION AND PHOSPHINE-BASED LIGAND AND USE THEREOF IN PROCESS OF OCTENES |
WO2017207280A1 (en) | 2016-05-31 | 2017-12-07 | IFP Energies Nouvelles | Catalytic composition comprising chromium and a phosphine-based ligand, and use thereof in an octene production method |
US10646858B2 (en) | 2016-05-31 | 2020-05-12 | IFP Energies Nouvelles | Catalytic composition based on chromium and a ligand based on phosphine and its use in a method for producing octenes |
CN106111200A (en) * | 2016-06-21 | 2016-11-16 | 东南大学 | Many metal corsslinkings for uns-dimethylhydrazine degraded coordinate catalyst and its preparation method and application |
CN106111200B (en) * | 2016-06-21 | 2019-03-12 | 东南大学 | More metal corsslinkings cooperation catalyst and its preparation method and application for uns-dimethylhydrazine degradation |
CN109563009A (en) * | 2016-07-15 | 2019-04-02 | 公共型股份公司希布尔控股 | Alkene oligomerization process |
EA039177B1 (en) * | 2016-07-15 | 2021-12-14 | Публичное акционерное общество "СИБУР Холдинг" | Method of oligomerization of olefins |
KR102218261B1 (en) | 2016-07-15 | 2021-02-23 | 퍼블릭 조인트 스톡 컴퍼니 “시부르 홀딩” | Method for oligomerization of olefins |
WO2018012997A1 (en) * | 2016-07-15 | 2018-01-18 | Public Joint Stock Company "Sibur Holding" | Method of oligomerization of olefins |
KR20190029663A (en) * | 2016-07-15 | 2019-03-20 | 퍼블릭 조인트 스톡 컴퍼니 “시부르 홀딩” | Methods of oligomerization of olefins |
US10807922B2 (en) | 2016-07-15 | 2020-10-20 | Public Joint Stock Company “SIBUR Holding” | Method of oligomerization of olefins |
US9944661B2 (en) | 2016-08-09 | 2018-04-17 | Chevron Phillips Chemical Company Lp | Olefin hydroboration |
US10960343B2 (en) | 2016-12-19 | 2021-03-30 | Lummus Technology Llc | Methods and systems for performing chemical separations |
WO2018116176A1 (en) | 2016-12-22 | 2018-06-28 | Sabic Global Technologies B.V. | Methods of producing linear alpha olefins |
WO2018122779A1 (en) | 2016-12-30 | 2018-07-05 | Sabic Global Technologies B.V. | Methods of producing linear alpha olefins |
US11001542B2 (en) | 2017-05-23 | 2021-05-11 | Lummus Technology Llc | Integration of oxidative coupling of methane processes |
US10493422B2 (en) | 2017-06-06 | 2019-12-03 | Chevron Phillips Chemical Company Lp | Fouling protection for an oligomerization reactor inlet |
US10232339B2 (en) | 2017-06-06 | 2019-03-19 | Chevron Phillips Chemical Company Lp | Fouling protection for an oligomerization reactor inlet |
KR20180137182A (en) | 2017-06-16 | 2018-12-27 | 에스케이이노베이션 주식회사 | Heteroatomic ligand, oligomerization catalyst containing the same, and production method of oligomer |
US11020729B1 (en) | 2017-06-16 | 2021-06-01 | Sk Innovation Co., Ltd. | Heteroatom ligand, oligomerization catalyst containing same, and method for preparing oligomer |
WO2018230846A1 (en) | 2017-06-16 | 2018-12-20 | 에스케이이노베이션 주식회사 | Heteroatom ligand, oligomerization catalyst containing same, and method for preparing oligomer |
US11691136B2 (en) | 2017-07-06 | 2023-07-04 | Mitsui Chemicals, Inc. | Olefin oligomerization catalyst and method for producing olefin oligomer in the presence of the same catalyst |
WO2019009390A1 (en) | 2017-07-06 | 2019-01-10 | 三井化学株式会社 | Catalyst for olefin multimerization and method for producing olefin multimer in presence of said catalyst |
KR20200026953A (en) | 2017-07-06 | 2020-03-11 | 미쓰이 가가쿠 가부시키가이샤 | Catalyst for olefin multimerization and method for producing olefin multimer in the presence of the catalyst |
KR20220110863A (en) | 2017-07-06 | 2022-08-09 | 미쓰이 가가쿠 가부시키가이샤 | Catalyst for olefin multimerization and method for producing olefin multimer in presence of said catalyst |
US10836689B2 (en) | 2017-07-07 | 2020-11-17 | Lummus Technology Llc | Systems and methods for the oxidative coupling of methane |
US10183960B1 (en) | 2017-09-22 | 2019-01-22 | Chevron Phillips Chemical Company Lp | Perfluorohydrocarbyl-N2-phosphinyl amidine compounds, chromium salt complexes, catalyst systems, and their use to oligomerize ethylene |
US10493442B2 (en) | 2017-09-22 | 2019-12-03 | Chevron Phillips Chemical Company Lp | Fluorinated N2-phosphinyl amidine compounds, chromium salt complexes, catalyst systems, and their use to oligomerize ethylene |
US10294171B2 (en) | 2017-09-22 | 2019-05-21 | Chevron Phillips Chemical Company Lp | Carbonyl-containing perfluorohydrocarbyl-N2-phosphinyl amidine compounds, chromium salt complexes and their use to oligomerize ethylene |
US10464862B2 (en) | 2017-09-28 | 2019-11-05 | Chevron Phillips Chemical Company Lp | Oligomerization reactions using aluminoxanes |
WO2019168249A1 (en) | 2018-02-27 | 2019-09-06 | 에스케이이노베이션 주식회사 | Ligand, oligomerization catalyst comprising same, and method for producing ethylene oligomer by using oligomerization catalyst |
US11224870B2 (en) | 2018-02-27 | 2022-01-18 | Sk Innovation Co., Ltd. | Ligand, oligomerization catalyst comprising same, and method for producing ethylene oligomer by using oligomerization catalyst |
KR20190102970A (en) | 2018-02-27 | 2019-09-04 | 에스케이이노베이션 주식회사 | Ligand, Oligomerization Catalyst And Process For Preparing Ethylene Oligomer Using Thereof |
FR3116738A1 (en) | 2020-11-30 | 2022-06-03 | IFP Energies Nouvelles | NEW CATALYTIC COMPOSITION BASED ON CHROMIUM COMPRISING AN AROMATIC ETHER ADDITIVE AND ASSOCIATED PROCESS FOR THE OLIGOMERIZATION OF ETHYLENE INTO OCTENE-1 |
FR3116739A1 (en) | 2020-11-30 | 2022-06-03 | IFP Energies Nouvelles | NEW CATALYTIC COMPOSITION BASED ON CHROME COMPRISING AN AROMATIC HYDROCARBON ADDITIVE AND ASSOCIATED METHOD FOR THE OLIGOMERIZATION OF ETHYLENE INTO OCTENE-1 |
FR3128710A1 (en) | 2021-11-02 | 2023-05-05 | IFP Energies Nouvelles | Ethylene oligomerization process using a catalytic composition comprising a chromium precursor, a PNP type ligand and an aluminoxane |
US11492305B1 (en) | 2021-11-08 | 2022-11-08 | Chevron Phillips Chemical Company, Lp | Chromium phosphinyl hydroisoindole amidine complexes for tetramerization of ethylene |
US11505513B1 (en) | 2021-11-08 | 2022-11-22 | Chevron Phillips Chemical Company, Lp | Chromium bicyclic phosphinyl amidine complexes for tetramerization of ethylene |
US11583843B1 (en) | 2021-11-08 | 2023-02-21 | Chevron Phillips Chemical Company, Lp | Chromium phosphinyl isoindole amidine complexes for tetramerization of ethylene |
US11623901B1 (en) | 2022-08-31 | 2023-04-11 | Saudi Arabian Oil Company | Catalyst systems that include silyl ether moieties |
US11639321B1 (en) | 2022-08-31 | 2023-05-02 | Saudi Arabian Oil Company | Catalyst systems that include meta-alkoxy substituted n-aryl bis-diphosphinoamine ligands |
FR3140775A1 (en) | 2022-10-17 | 2024-04-19 | IFP Energies Nouvelles | New catalytic composition based on supported chromium or titanium |
WO2024083616A1 (en) | 2022-10-17 | 2024-04-25 | IFP Energies Nouvelles | Novel chromium- or titanium-based supported catalytic composition |
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