BRPI1013324A2 - "composição catalisadora e processo de oligomerização de etileno." - Google Patents
"composição catalisadora e processo de oligomerização de etileno." Download PDFInfo
- Publication number
- BRPI1013324A2 BRPI1013324A2 BRPI1013324A BRPI1013324A BRPI1013324A2 BR PI1013324 A2 BRPI1013324 A2 BR PI1013324A2 BR PI1013324 A BRPI1013324 A BR PI1013324A BR PI1013324 A BRPI1013324 A BR PI1013324A BR PI1013324 A2 BRPI1013324 A2 BR PI1013324A2
- Authority
- BR
- Brazil
- Prior art keywords
- chloride
- ethylene
- catalyst
- modifier
- aluminum
- Prior art date
Links
- 239000003054 catalyst Substances 0.000 title claims abstract description 65
- 239000005977 Ethylene Substances 0.000 title claims abstract description 48
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 title claims abstract description 47
- 238000000034 method Methods 0.000 title claims abstract description 34
- 230000008569 process Effects 0.000 title claims abstract description 33
- 239000000203 mixture Substances 0.000 title claims abstract description 28
- 238000006384 oligomerization reaction Methods 0.000 title claims abstract description 11
- 239000003607 modifier Substances 0.000 claims abstract description 30
- 239000012190 activator Substances 0.000 claims abstract description 18
- 239000003446 ligand Substances 0.000 claims abstract description 16
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 9
- 150000002367 halogens Chemical class 0.000 claims abstract description 9
- 125000003118 aryl group Chemical group 0.000 claims abstract description 8
- 150000001845 chromium compounds Chemical class 0.000 claims abstract description 8
- -1 amino, trimethylsilyl Chemical group 0.000 claims abstract description 7
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 4
- 229910001502 inorganic halide Inorganic materials 0.000 claims abstract description 3
- 239000011651 chromium Substances 0.000 claims description 55
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 claims description 16
- 230000003197 catalytic effect Effects 0.000 claims description 15
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 13
- 229910052804 chromium Inorganic materials 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 11
- 229910052782 aluminium Inorganic materials 0.000 claims description 11
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- 125000004122 cyclic group Chemical group 0.000 claims description 9
- 239000000470 constituent Substances 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 150000004820 halides Chemical class 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 125000002524 organometallic group Chemical group 0.000 claims description 5
- 229910052698 phosphorus Inorganic materials 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 4
- 239000006071 cream Substances 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- ISYORFGKSZLPNW-UHFFFAOYSA-N propan-2-ylazanium;chloride Chemical compound [Cl-].CC(C)[NH3+] ISYORFGKSZLPNW-UHFFFAOYSA-N 0.000 claims description 4
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 claims description 4
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 claims description 3
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 3
- CPOFMOWDMVWCLF-UHFFFAOYSA-N methyl(oxo)alumane Chemical compound C[Al]=O CPOFMOWDMVWCLF-UHFFFAOYSA-N 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- TZJOIDXKFOTKCW-UHFFFAOYSA-N n-cyclohexylcyclohexanamine;5-[(2-methylpropan-2-yl)oxy]-5-oxo-2-(phenylmethoxycarbonylamino)pentanoic acid Chemical compound C1CCCCC1NC1CCCCC1.CC(C)(C)OC(=O)CCC(C(O)=O)NC(=O)OCC1=CC=CC=C1 TZJOIDXKFOTKCW-UHFFFAOYSA-N 0.000 claims description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 claims description 2
- 150000004714 phosphonium salts Chemical class 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- YMBCJWGVCUEGHA-UHFFFAOYSA-M tetraethylammonium chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC YMBCJWGVCUEGHA-UHFFFAOYSA-M 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 claims 1
- CMAOLVNGLTWICC-UHFFFAOYSA-N 2-fluoro-5-methylbenzonitrile Chemical compound CC1=CC=C(F)C(C#N)=C1 CMAOLVNGLTWICC-UHFFFAOYSA-N 0.000 claims 1
- AKECHHUMANPOQX-UHFFFAOYSA-N 3-(bromomethyl)-6,7-dichloro-2,3-dihydro-1,4-benzodioxine Chemical compound O1CC(CBr)OC2=C1C=C(Cl)C(Cl)=C2 AKECHHUMANPOQX-UHFFFAOYSA-N 0.000 claims 1
- 241000287531 Psittacidae Species 0.000 claims 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims 1
- 239000012346 acetyl chloride Substances 0.000 claims 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 claims 1
- SHZIWNPUGXLXDT-UHFFFAOYSA-N caproic acid ethyl ester Natural products CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 claims 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 claims 1
- FBEVECUEMUUFKM-UHFFFAOYSA-M tetrapropylazanium;chloride Chemical compound [Cl-].CCC[N+](CCC)(CCC)CCC FBEVECUEMUUFKM-UHFFFAOYSA-M 0.000 claims 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 claims 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical group C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 claims 1
- 239000003426 co-catalyst Substances 0.000 abstract description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 57
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 47
- 229940093470 ethylene Drugs 0.000 description 44
- 230000000694 effects Effects 0.000 description 18
- 239000000047 product Substances 0.000 description 18
- 230000015572 biosynthetic process Effects 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 238000002474 experimental method Methods 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- 239000002904 solvent Substances 0.000 description 12
- 239000011230 binding agent Substances 0.000 description 11
- 125000005647 linker group Chemical group 0.000 description 11
- 238000005829 trimerization reaction Methods 0.000 description 11
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 230000003647 oxidation Effects 0.000 description 8
- 238000007254 oxidation reaction Methods 0.000 description 8
- 239000007789 gas Substances 0.000 description 7
- 230000007246 mechanism Effects 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 239000004698 Polyethylene Substances 0.000 description 5
- 238000004817 gas chromatography Methods 0.000 description 5
- 239000012535 impurity Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 239000002243 precursor Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 238000006555 catalytic reaction Methods 0.000 description 4
- 238000009826 distribution Methods 0.000 description 4
- 238000002955 isolation Methods 0.000 description 4
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical group CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 150000001844 chromium Chemical class 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 206010010071 Coma Diseases 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000012018 catalyst precursor Substances 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- VURFVHCLMJOLKN-UHFFFAOYSA-N diphosphane Chemical compound PP VURFVHCLMJOLKN-UHFFFAOYSA-N 0.000 description 2
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 230000037361 pathway Effects 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 125000004437 phosphorous atom Chemical group 0.000 description 2
- 239000002574 poison Substances 0.000 description 2
- 231100000614 poison Toxicity 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000007306 turnover Effects 0.000 description 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 241001167556 Catena Species 0.000 description 1
- 244000103152 Eleocharis tuberosa Species 0.000 description 1
- 235000014309 Eleocharis tuberosa Nutrition 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 240000002853 Nelumbo nucifera Species 0.000 description 1
- 235000006508 Nelumbo nucifera Nutrition 0.000 description 1
- 235000006510 Nelumbo pentapetala Nutrition 0.000 description 1
- 235000014030 Podocarpus spicatus Nutrition 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- LGWNWBQRJIXNNX-UHFFFAOYSA-N [Ca].CCCCCC Chemical compound [Ca].CCCCCC LGWNWBQRJIXNNX-UHFFFAOYSA-N 0.000 description 1
- FIDHUEJNXPLJNN-UHFFFAOYSA-N [ClH]=C Chemical compound [ClH]=C FIDHUEJNXPLJNN-UHFFFAOYSA-N 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000005210 alkyl ammonium group Chemical group 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- PHIQHXFUZVPYII-UHFFFAOYSA-N carnitine Chemical compound C[N+](C)(C)CC(O)CC([O-])=O PHIQHXFUZVPYII-UHFFFAOYSA-N 0.000 description 1
- 239000003060 catalysis inhibitor Substances 0.000 description 1
- 230000035568 catharsis Effects 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 239000013626 chemical specie Substances 0.000 description 1
- XEHUIDSUOAGHBW-UHFFFAOYSA-N chromium;pentane-2,4-dione Chemical compound [Cr].CC(=O)CC(C)=O.CC(=O)CC(C)=O.CC(=O)CC(C)=O XEHUIDSUOAGHBW-UHFFFAOYSA-N 0.000 description 1
- 238000010960 commercial process Methods 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 description 1
- REZZEXDLIUJMMS-UHFFFAOYSA-M dimethyldioctadecylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC REZZEXDLIUJMMS-UHFFFAOYSA-M 0.000 description 1
- TYBOKIPGZHEQSB-UHFFFAOYSA-N diphospazane Chemical class PNP TYBOKIPGZHEQSB-UHFFFAOYSA-N 0.000 description 1
- 239000001177 diphosphate Substances 0.000 description 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 1
- 235000011180 diphosphates Nutrition 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- UPCIBFUJJLCOQG-UHFFFAOYSA-L ethyl-[2-[2-[ethyl(dimethyl)azaniumyl]ethyl-methylamino]ethyl]-dimethylazanium;dibromide Chemical compound [Br-].[Br-].CC[N+](C)(C)CCN(C)CC[N+](C)(C)CC UPCIBFUJJLCOQG-UHFFFAOYSA-L 0.000 description 1
- MGDOJPNDRJNJBK-UHFFFAOYSA-N ethylaluminum Chemical compound [Al].C[CH2] MGDOJPNDRJNJBK-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000013467 fragmentation Methods 0.000 description 1
- 238000006062 fragmentation reaction Methods 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical class [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000008863 intramolecular interaction Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000005304 joining Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 235000015073 liquid stocks Nutrition 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 230000004001 molecular interaction Effects 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 238000006213 oxygenation reaction Methods 0.000 description 1
- RGCLLPNLLBQHPF-HJWRWDBZSA-N phosphamidon Chemical compound CCN(CC)C(=O)C(\Cl)=C(/C)OP(=O)(OC)OC RGCLLPNLLBQHPF-HJWRWDBZSA-N 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010405 reoxidation reaction Methods 0.000 description 1
- 230000003252 repetitive effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- XXOQBOOKZUDHDO-UHFFFAOYSA-L tetraethylazanium dichloride Chemical compound [Cl-].[Cl-].CC[N+](CC)(CC)CC.CC[N+](CC)(CC)CC XXOQBOOKZUDHDO-UHFFFAOYSA-L 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000009966 trimming Methods 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
- B01J31/14—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides of aluminium or boron
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
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- B01J23/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
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- B01J31/14—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides of aluminium or boron
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- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
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- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
- B01J31/1845—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing phosphorus
- B01J31/1885—Ligands comprising two different formal oxidation states of phosphorus in one at least bidentate ligand, e.g. phosphite/phosphinite
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/02—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons
- C07C2/04—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation
- C07C2/06—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation of alkenes, i.e. acyclic hydrocarbons having only one carbon-to-carbon double bond
- C07C2/08—Catalytic processes
- C07C2/26—Catalytic processes with hydrides or organic compounds
- C07C2/36—Catalytic processes with hydrides or organic compounds as phosphines, arsines, stilbines or bismuthines
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/20—Olefin oligomerisation or telomerisation
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- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/02—Compositional aspects of complexes used, e.g. polynuclearity
- B01J2531/0238—Complexes comprising multidentate ligands, i.e. more than 2 ionic or coordinative bonds from the central metal to the ligand, the latter having at least two donor atoms, e.g. N, O, S, P
- B01J2531/0258—Flexible ligands, e.g. mainly sp3-carbon framework as exemplified by the "tedicyp" ligand, i.e. cis-cis-cis-1,2,3,4-tetrakis(diphenylphosphinomethyl)cyclopentane
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/60—Complexes comprising metals of Group VI (VIA or VIB) as the central metal
- B01J2531/62—Chromium
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- C07C2531/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
- C07C2531/14—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides of aluminium or boron
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- C07C2531/24—Phosphines
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- Chemical & Material Sciences (AREA)
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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| EP09005212A EP2239056B1 (en) | 2009-04-09 | 2009-04-09 | Catalyst composition and process for oligomerization of ethylene |
| PCT/EP2010/001842 WO2010115520A1 (en) | 2009-04-09 | 2010-03-24 | Catalyst composition and process for oligomerization of ethylene |
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| BRPI1013324A2 true BRPI1013324A2 (pt) | 2019-08-27 |
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| BRPI1013324A BRPI1013324A2 (pt) | 2009-04-09 | 2010-03-24 | "composição catalisadora e processo de oligomerização de etileno." |
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| ES2371218T3 (es) | 2009-04-09 | 2011-12-28 | Saudi Basic Industries Corporation | Composición de catalizador y procedimiento para la oligomerización de etileno. |
| MX2012007558A (es) | 2009-12-31 | 2012-07-25 | Chevron Phillips Chemical Co | Compuestos fosfinil amidina, complejos metalicos, sistemas catalizadores y su uso para oligomerizar o polimerizar olefinas. |
| EP2489431B1 (en) | 2011-02-16 | 2013-05-01 | Linde AG | Method for preparing a catalyst composition for oligomerization of ethylene and respective catalyst composition pre-formation unit |
| CA2747501C (en) * | 2011-07-26 | 2018-01-23 | Nova Chemicals Corporation | "bulk" ethylene oligomerization |
| CA2765429C (en) | 2012-01-25 | 2019-12-31 | Nova Chemicals Corporation | P-n-p ligand |
| 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 |
| EP2684857A1 (en) | 2012-07-10 | 2014-01-15 | Saudi Basic Industries Corporation | Method for oligomerization of ethylene |
| EP2738151B8 (en) | 2012-11-28 | 2014-12-17 | Saudi Basic Industries Corporation | Process for oligomerization of ethylene |
| EP2764914A1 (en) * | 2013-02-11 | 2014-08-13 | Linde AG | Metalated PNPNH ligand, catalyst composition and use thereof in the oligomerization of ethylene |
| EP2764913A1 (en) | 2013-02-11 | 2014-08-13 | Linde AG | Method for purifying a crude PNPNH compound |
| EP2764915B1 (en) | 2013-02-11 | 2017-03-22 | Linde AG | Purification method for a crude PNPNH compound |
| EP2832445A1 (en) | 2013-07-29 | 2015-02-04 | Linde AG | Catalyst composition and process for oligomerization of ethylene |
| KR101638980B1 (ko) | 2013-09-30 | 2016-07-12 | 주식회사 엘지화학 | 리간드 화합물, 유기크롬 화합물, 에틸렌 올리고머화용 촉매 시스템, 및 이를 이용한 에틸렌 올리고머화 방법 |
| CA2933131A1 (en) * | 2014-01-06 | 2015-07-09 | Saudi Basic Industries Corporation | Modified preformation method for catalyst activation in ethylene reactions |
| WO2015114611A1 (en) * | 2014-02-03 | 2015-08-06 | Saudi Basic Industries Corporation | Catalyst composition pre-formation unit for preparing a catalyst composition for oligomerization of ethylene |
| CA2954836C (en) | 2014-07-24 | 2018-10-09 | Sabic Global Technologies B.V. | Catalyst composition and process for oligomerization of ethylene to produce 1-hexene and/or 1-octene |
| CN105481662B (zh) * | 2014-09-18 | 2017-10-24 | 江苏和成新材料有限公司 | 制备用于生产含二氟甲氧基液晶化合物的中间体的方法 |
| US9505675B2 (en) * | 2015-02-09 | 2016-11-29 | Chevron Phillips Chemical Company Lp | Deactivation of a process by-product |
| EP3350143B1 (en) | 2015-09-16 | 2024-05-15 | SABIC Global Technologies B.V. | Process for deactivation of an olefin oligomerization catalyst |
| EP3356884B1 (en) | 2015-09-29 | 2023-07-05 | Alliance for Sustainable Energy, LLC | Energy-harvesting chromogenic devices |
| FR3045414B1 (fr) * | 2015-12-18 | 2019-12-27 | IFP Energies Nouvelles | Nouvelle composition catalytique a base de nickel et de ligand de type phosphine et d'une base de lewis et son utilisation dans un procede d'oligomerisation des olefines |
| US10781147B2 (en) | 2015-12-22 | 2020-09-22 | Sabic Global Technologies B.V. | Methods for toluene recovery from linear alpha olefin production |
| KR102545533B1 (ko) * | 2016-05-27 | 2023-06-21 | 에스케이이노베이션 주식회사 | 올리고머화 촉매 및 이를 이용한 에틸렌 올리고머의 제조방법 |
| EP3562585B1 (en) | 2016-12-30 | 2023-08-23 | SABIC Global Technologies B.V. | Method for preparation of homogenous catalyst for selective 1-hexene production |
| CN110494218A (zh) * | 2016-12-30 | 2019-11-22 | 沙特基础工业全球技术有限公司 | 用于选择性1-己烯生产的催化剂溶液的制备方法 |
| WO2018209104A1 (en) | 2017-05-10 | 2018-11-15 | Alliance For Sustainable Energy, Llc | Multilayer carbon nanotube film-containing devices |
| KR102284949B1 (ko) * | 2017-06-16 | 2021-08-03 | 에스케이이노베이션 주식회사 | 파울링 방지방법 및 올레핀의 올리고머화 방법 |
| KR102604431B1 (ko) * | 2018-07-26 | 2023-11-22 | 에스케이이노베이션 주식회사 | 선형 알파 올레핀 제조방법 |
| CN113597419A (zh) * | 2019-03-13 | 2021-11-02 | Tpc集团有限责任公司 | 选择性地生产不同线性α-烯烃的弹性制造系统 |
| US11612883B2 (en) | 2020-11-30 | 2023-03-28 | Saudi Arabian Oil Company | Catalyst systems |
| WO2022115751A1 (en) | 2020-11-30 | 2022-06-02 | Saudi Arabian Oil Company | Catalyst systems |
| WO2022115749A1 (en) * | 2020-11-30 | 2022-06-02 | Saudi Arabian Oil Company | Catalyst systems |
| US11458463B2 (en) | 2020-11-30 | 2022-10-04 | Saudi Arabian Oil Company | Catalyst systems |
| US11623208B2 (en) | 2020-11-30 | 2023-04-11 | Saudi Arabian Oil Company | Catalyst systems |
| EP4294564B1 (en) | 2021-03-12 | 2025-12-24 | Saudi Arabian Oil Company | Catalyst systems |
| WO2023027749A1 (en) | 2021-08-26 | 2023-03-02 | Saudi Arabian Oil Company | Catalyst systems |
| US11639321B1 (en) | 2022-08-31 | 2023-05-02 | Saudi Arabian Oil Company | Catalyst systems that include meta-alkoxy substituted n-aryl bis-diphosphinoamine ligands |
| US11623901B1 (en) | 2022-08-31 | 2023-04-11 | Saudi Arabian Oil Company | Catalyst systems that include silyl ether moieties |
| CN115445667B (zh) * | 2022-09-22 | 2023-12-22 | 中化泉州石化有限公司 | 一种乙烯齐聚用催化剂及其应用 |
| LU506480B1 (en) | 2024-02-28 | 2025-08-28 | Sabic Global Technologies Bv | Method for oligomerization of ethylene |
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| FR2659871B1 (fr) * | 1990-03-20 | 1992-06-05 | Inst Francais Du Petrole | Composition liquide non aqueuse a caractere ionique et son utilisation comme solvant. invention de mm. yves chauvin, dominique commereuc, isabelle guibard, andre hirschauer, helene olivier, lucien saussine. |
| JP3289372B2 (ja) * | 1993-03-15 | 2002-06-04 | 三菱化学株式会社 | α−オレフィンの低重合方法 |
| WO1997033924A1 (en) * | 1996-03-14 | 1997-09-18 | Mitsubishi Chemical Corporation | PROCESS FOR THE PRODUCTION OF α-OLEFIN OLIGOMERS |
| DE69727460T2 (de) | 1996-04-04 | 2004-07-01 | Bp Chemicals Ltd. | Eine verbindung, die in einer katalytischen zusammensetzung verwendbar ist |
| JPH10109946A (ja) * | 1996-08-12 | 1998-04-28 | Mitsubishi Chem Corp | α−オレフィン低重合体の製造方法 |
| GB9918635D0 (en) | 1999-08-06 | 1999-10-13 | Bp Chem Int Ltd | Polymerisation process |
| GB0016895D0 (en) | 2000-07-11 | 2000-08-30 | Bp Chem Int Ltd | Olefin oligomerisation |
| JP2002066329A (ja) * | 2000-08-28 | 2002-03-05 | Tosoh Corp | エチレンの三量化触媒及びこの触媒を用いたエチレンの三量化方法 |
| JP2002233764A (ja) * | 2000-12-05 | 2002-08-20 | Tosoh Corp | エチレンの三量化触媒およびこの触媒を用いたエチレンの三量化方法 |
| WO2003053891A1 (en) | 2001-12-20 | 2003-07-03 | Sasol Technology (Pty) Ltd. | Trimerisation and oligomerisation of olefins using a chromium based catalyst |
| JP4308015B2 (ja) | 2001-12-20 | 2009-08-05 | サソル テクノロジー （ピーティーワイ）リミテッド | クロムを主成分とした触媒を使用したオレフィン類の三量化およびオリゴマー化 |
| CN100366435C (zh) | 2002-12-19 | 2008-02-06 | 松下电器产业株式会社 | 打印控制装置、打印控制方法和打印机 |
| WO2004056477A1 (en) | 2002-12-20 | 2004-07-08 | Sasol Technology (Pty) Limited | Trimerisation of olefins |
| CN100486944C (zh) | 2003-09-19 | 2009-05-13 | 中国石油天然气股份有限公司 | 一种在乙烯齐聚催化剂体系存在下制备1-己烯的新方法 |
| US7273959B2 (en) | 2003-10-10 | 2007-09-25 | Shell Oil Company | Catalytic trimerization of olefinic monomers |
| KR20080080570A (ko) * | 2005-11-21 | 2008-09-04 | 셀 인터나쵸나아레 레사아치 마아츠샤피 비이부이 | 올레핀 단량체의 올리고머화를 위한 촉매법 |
| CN100443178C (zh) * | 2006-03-10 | 2008-12-17 | 中国石油天然气股份有限公司 | 一种乙烯低聚的催化剂组合物及其应用 |
| EP2098542A4 (en) * | 2006-12-28 | 2011-03-09 | Mitsubishi Chem Corp | PROCESS FOR THE PRODUCTION OF LOW MOLECULAR WEIGHT POLYMER POLYMERS |
| RU2456078C2 (ru) | 2007-07-11 | 2012-07-20 | Линде Аг | Каталитическая композиция и способ ди-, три- и/или тетрамеризации этилена |
| CA2703021C (en) * | 2007-11-28 | 2015-01-20 | Vugar Aliyev | Catalyst composition and process for oligomerization of ethylene |
| ES2371218T3 (es) | 2009-04-09 | 2011-12-28 | Saudi Basic Industries Corporation | Composición de catalizador y procedimiento para la oligomerización de etileno. |
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| RU2011145325A (ru) | 2013-05-20 |
| JP2012523306A (ja) | 2012-10-04 |
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| CA2754122A1 (en) | 2010-10-14 |
| EP2239056B1 (en) | 2011-07-20 |
| CN102387860B (zh) | 2013-11-20 |
| TWI461242B (zh) | 2014-11-21 |
| MX2011010660A (es) | 2011-10-28 |
| JP5571769B2 (ja) | 2014-08-13 |
| WO2010115520A1 (en) | 2010-10-14 |
| ATE516878T1 (de) | 2011-08-15 |
| EP2239056A1 (en) | 2010-10-13 |
| ES2371218T3 (es) | 2011-12-28 |
| US9018431B2 (en) | 2015-04-28 |
| RU2525917C2 (ru) | 2014-08-20 |
| US20120029258A1 (en) | 2012-02-02 |
| CA2754122C (en) | 2015-12-22 |
| KR101466431B1 (ko) | 2014-11-28 |
| SG174160A1 (en) | 2011-10-28 |
| KR20120004985A (ko) | 2012-01-13 |
| TW201038327A (en) | 2010-11-01 |
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