CA2672385C - Process for production of .alpha.-olefin low polymers using chromium catalyst - Google Patents
Process for production of .alpha.-olefin low polymers using chromium catalyst Download PDFInfo
- Publication number
- CA2672385C CA2672385C CA2672385A CA2672385A CA2672385C CA 2672385 C CA2672385 C CA 2672385C CA 2672385 A CA2672385 A CA 2672385A CA 2672385 A CA2672385 A CA 2672385A CA 2672385 C CA2672385 C CA 2672385C
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- CA
- Canada
- Prior art keywords
- olefin
- reactor
- alpha
- chromium
- solvent
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000003054 catalyst Substances 0.000 title claims abstract description 87
- 229920000642 polymer Polymers 0.000 title claims abstract description 56
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 44
- 238000000034 method Methods 0.000 title claims description 27
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 title description 9
- 229910052804 chromium Inorganic materials 0.000 title description 9
- 239000011651 chromium Substances 0.000 title description 9
- 230000008569 process Effects 0.000 title description 7
- 239000007789 gas Substances 0.000 claims abstract description 71
- 239000002904 solvent Substances 0.000 claims abstract description 60
- 239000011261 inert gas Substances 0.000 claims abstract description 50
- 150000001875 compounds Chemical class 0.000 claims abstract description 40
- 239000012295 chemical reaction liquid Substances 0.000 claims abstract description 33
- -1 nitrogen-containing compound Chemical class 0.000 claims abstract description 32
- 150000001844 chromium Chemical class 0.000 claims abstract description 31
- 238000006243 chemical reaction Methods 0.000 claims abstract description 27
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 26
- 150000001845 chromium compounds Chemical class 0.000 claims abstract description 24
- 229910052782 aluminium Inorganic materials 0.000 claims abstract description 20
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims abstract description 19
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 73
- 239000005977 Ethylene Substances 0.000 claims description 73
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 55
- 229910052757 nitrogen Inorganic materials 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 150000002367 halogens Chemical class 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 239000000178 monomer Substances 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 abstract description 6
- 150000001408 amides Chemical class 0.000 abstract description 4
- 150000003949 imides Chemical class 0.000 abstract description 4
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 52
- 238000000926 separation method Methods 0.000 description 35
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 21
- 238000007872 degassing Methods 0.000 description 15
- 238000009835 boiling Methods 0.000 description 14
- 239000002994 raw material Substances 0.000 description 14
- 230000000052 comparative effect Effects 0.000 description 13
- PAPNRQCYSFBWDI-UHFFFAOYSA-N DMP Natural products CC1=CC=C(C)N1 PAPNRQCYSFBWDI-UHFFFAOYSA-N 0.000 description 11
- 239000000243 solution Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- 230000003247 decreasing effect Effects 0.000 description 6
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 6
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 229930195734 saturated hydrocarbon Natural products 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 238000005829 trimerization reaction Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000002723 alicyclic group Chemical group 0.000 description 3
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 239000001569 carbon dioxide Substances 0.000 description 3
- 239000007810 chemical reaction solvent Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 3
- 239000013638 trimer Substances 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- IGJQUJNPMOYEJY-UHFFFAOYSA-N 2-acetylpyrrole Chemical compound CC(=O)C1=CC=CN1 IGJQUJNPMOYEJY-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- GXDHCNNESPLIKD-UHFFFAOYSA-N 2-methylhexane Chemical compound CCCCC(C)C GXDHCNNESPLIKD-UHFFFAOYSA-N 0.000 description 2
- PFEOZHBOMNWTJB-UHFFFAOYSA-N 3-methylpentane Chemical compound CCC(C)CC PFEOZHBOMNWTJB-UHFFFAOYSA-N 0.000 description 2
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- WZYSPXAFRUXTTD-UHFFFAOYSA-N aluminum pyrrol-1-ide Chemical compound [Al+3].C=1C=C[N-]C=1.C=1C=C[N-]C=1.C=1C=C[N-]C=1 WZYSPXAFRUXTTD-UHFFFAOYSA-N 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 150000007942 carboxylates Chemical class 0.000 description 2
- 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 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- CQYBWJYIKCZXCN-UHFFFAOYSA-N diethylaluminum Chemical compound CC[Al]CC CQYBWJYIKCZXCN-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 239000001307 helium Substances 0.000 description 2
- 229910052734 helium Inorganic materials 0.000 description 2
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 2
- VHHHONWQHHHLTI-UHFFFAOYSA-N hexachloroethane Chemical compound ClC(Cl)(Cl)C(Cl)(Cl)Cl VHHHONWQHHHLTI-UHFFFAOYSA-N 0.000 description 2
- 125000001905 inorganic group Chemical group 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012544 monitoring process Methods 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 125000000962 organic group Chemical group 0.000 description 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- PALOVZYYXHMYGK-UHFFFAOYSA-N 1,2,3-trichlorocyclopropane Chemical compound ClC1C(Cl)C1Cl PALOVZYYXHMYGK-UHFFFAOYSA-N 0.000 description 1
- DTOMKKRROVKOGE-UHFFFAOYSA-N 1,2,4,5-tetrachloro-3,6-bis(trichloromethyl)benzene Chemical compound ClC1=C(Cl)C(C(Cl)(Cl)Cl)=C(Cl)C(Cl)=C1C(Cl)(Cl)Cl DTOMKKRROVKOGE-UHFFFAOYSA-N 0.000 description 1
- NBXDXMFYTJNWCS-UHFFFAOYSA-N 2,3,4,5-tetrachloro-1h-pyrrole Chemical compound ClC=1NC(Cl)=C(Cl)C=1Cl NBXDXMFYTJNWCS-UHFFFAOYSA-N 0.000 description 1
- MFFMQGGZCLEMCI-UHFFFAOYSA-N 2,4-dimethyl-1h-pyrrole Chemical compound CC1=CNC(C)=C1 MFFMQGGZCLEMCI-UHFFFAOYSA-N 0.000 description 1
- NYXZOJXKSYZYPU-UHFFFAOYSA-N 2,5-dimethylpyrrol-1-ide;ethylaluminum(2+) Chemical compound CC[Al+2].CC1=CC=C(C)[N-]1.CC1=CC=C(C)[N-]1 NYXZOJXKSYZYPU-UHFFFAOYSA-N 0.000 description 1
- GXSYXPDGMUORDR-UHFFFAOYSA-N 2-ethyl-5-methyl-1h-pyrrole Chemical compound CCC1=CC=C(C)N1 GXSYXPDGMUORDR-UHFFFAOYSA-N 0.000 description 1
- CMAOLVNGLTWICC-UHFFFAOYSA-N 2-fluoro-5-methylbenzonitrile Chemical compound CC1=CC=C(F)C(C#N)=C1 CMAOLVNGLTWICC-UHFFFAOYSA-N 0.000 description 1
- PFRKGGQLYAMPST-UHFFFAOYSA-N 3,4-dichloro-1h-pyrrole Chemical compound ClC1=CNC=C1Cl PFRKGGQLYAMPST-UHFFFAOYSA-N 0.000 description 1
- OJFOWGWQOFZNNJ-UHFFFAOYSA-N 3,4-dimethyl-1h-pyrrole Chemical compound CC1=CNC=C1C OJFOWGWQOFZNNJ-UHFFFAOYSA-N 0.000 description 1
- YHQXBTXEYZIYOV-UHFFFAOYSA-N 3-methylbut-1-ene Chemical compound CC(C)C=C YHQXBTXEYZIYOV-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical group O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- WDNIVTZNAPEMHF-UHFFFAOYSA-N acetic acid;chromium Chemical compound [Cr].CC(O)=O.CC(O)=O WDNIVTZNAPEMHF-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- UJYFINNESHCKPC-UHFFFAOYSA-N aluminum 2,5-dimethylpyrrol-1-ide Chemical compound [Al+3].CC1=CC=C(C)[N-]1.CC1=CC=C(C)[N-]1.CC1=CC=C(C)[N-]1 UJYFINNESHCKPC-UHFFFAOYSA-N 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000006757 chemical reactions by type Methods 0.000 description 1
- RPBPCPJJHKASGQ-UHFFFAOYSA-K chromium(3+);octanoate Chemical compound [Cr+3].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O.CCCCCCCC([O-])=O RPBPCPJJHKASGQ-UHFFFAOYSA-K 0.000 description 1
- WYYQVWLEPYFFLP-UHFFFAOYSA-K chromium(3+);triacetate Chemical compound [Cr+3].CC([O-])=O.CC([O-])=O.CC([O-])=O WYYQVWLEPYFFLP-UHFFFAOYSA-K 0.000 description 1
- OXMLCJOPQGRRKV-UHFFFAOYSA-K chromium(3+);tribenzoate Chemical compound [Cr+3].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 OXMLCJOPQGRRKV-UHFFFAOYSA-K 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- HJXBDPDUCXORKZ-UHFFFAOYSA-N diethylalumane Chemical compound CC[AlH]CC HJXBDPDUCXORKZ-UHFFFAOYSA-N 0.000 description 1
- WAZVBTLPAZNDOZ-UHFFFAOYSA-N diethylalumanylium pyrrol-1-ide Chemical compound CC[Al+]CC.C=1C=C[N-]C=1 WAZVBTLPAZNDOZ-UHFFFAOYSA-N 0.000 description 1
- YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- GCPCLEKQVMKXJM-UHFFFAOYSA-N ethoxy(diethyl)alumane Chemical compound CCO[Al](CC)CC GCPCLEKQVMKXJM-UHFFFAOYSA-N 0.000 description 1
- JYJPEEPQPDUKKO-UHFFFAOYSA-N ethylaluminum(2+);pyrrol-1-ide Chemical compound CC[Al+2].C=1C=C[N-]C=1.C=1C=C[N-]C=1 JYJPEEPQPDUKKO-UHFFFAOYSA-N 0.000 description 1
- 150000005826 halohydrocarbons Chemical class 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229920000092 linear low density polyethylene Polymers 0.000 description 1
- 239000004707 linear low-density polyethylene Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- GHTQTHLNYUEMQK-UHFFFAOYSA-N lithium;pyrrol-1-ide Chemical compound [Li]N1C=CC=C1 GHTQTHLNYUEMQK-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- BNIXVQGCZULYKV-UHFFFAOYSA-N pentachloroethane Chemical compound ClC(Cl)C(Cl)(Cl)Cl BNIXVQGCZULYKV-UHFFFAOYSA-N 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- UNNALYHKSWAHKE-UHFFFAOYSA-N potassium;2,5-dimethylpyrrol-1-ide Chemical compound [K+].CC1=CC=C(C)[N-]1 UNNALYHKSWAHKE-UHFFFAOYSA-N 0.000 description 1
- YWIWIWKNPYGWLT-UHFFFAOYSA-N potassium;pyrrol-1-ide Chemical compound [K+].C=1C=C[N-]C=1 YWIWIWKNPYGWLT-UHFFFAOYSA-N 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- MFTDDEGCJOYPMG-UHFFFAOYSA-N sodium;pyrrol-1-ide Chemical compound [Na+].C=1C=C[N-]C=1 MFTDDEGCJOYPMG-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical group S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 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
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- JLYXXMFPNIAWKQ-UHFFFAOYSA-N γ Benzene hexachloride Chemical compound ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
- B01J31/2208—Oxygen, e.g. acetylacetonates
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
- B01J31/14—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides of aluminium or boron
- B01J31/143—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides of aluminium or boron of aluminium
-
- 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
-
- 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
- C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/10—Polymerisation reactions involving at least dual use catalysts, e.g. for both oligomerisation and polymerisation
- B01J2231/12—Olefin polymerisation or copolymerisation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/20—Olefin oligomerisation or telomerisation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/60—Complexes comprising metals of Group VI (VIA or VIB) as the central metal
- B01J2531/62—Chromium
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerisation Methods In General (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Polymerization Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2006354541 | 2006-12-28 | ||
| JP2006-354541 | 2006-12-28 | ||
| PCT/JP2007/070572 WO2008081638A1 (ja) | 2006-12-28 | 2007-10-22 | α－オレフィン低重合体の製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2672385A1 CA2672385A1 (en) | 2008-07-10 |
| CA2672385C true CA2672385C (en) | 2014-10-14 |
Family
ID=39588323
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2672385A Active CA2672385C (en) | 2006-12-28 | 2007-10-22 | Process for production of .alpha.-olefin low polymers using chromium catalyst |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US9421534B2 (enExample) |
| EP (1) | EP2098542A4 (enExample) |
| JP (2) | JP5444615B2 (enExample) |
| CN (1) | CN101547941B (enExample) |
| BR (1) | BRPI0719595B1 (enExample) |
| CA (1) | CA2672385C (enExample) |
| EA (1) | EA024462B1 (enExample) |
| WO (1) | WO2008081638A1 (enExample) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2672385C (en) | 2006-12-28 | 2014-10-14 | Mitsubishi Chemical Corporation | Process for production of .alpha.-olefin low polymers using chromium catalyst |
| ES2371218T3 (es) * | 2009-04-09 | 2011-12-28 | Saudi Basic Industries Corporation | Composición de catalizador y procedimiento para la oligomerización de etileno. |
| WO2011118533A1 (ja) * | 2010-03-26 | 2011-09-29 | 三菱化学株式会社 | α－オレフィン低重合体の製造方法 |
| JP5793899B2 (ja) * | 2011-03-09 | 2015-10-14 | 三菱化学株式会社 | １−ヘキセンの製造方法 |
| JP2013231015A (ja) * | 2012-05-02 | 2013-11-14 | Idemitsu Kosan Co Ltd | オレフィンオリゴマーの製造方法 |
| FR2992962B1 (fr) * | 2012-07-04 | 2015-06-26 | Axens | Procede de separation de l'hexene-1 a partir d'un melange de produits issus d'une zone de trimerisation de l'ethylene |
| JP6459587B2 (ja) * | 2014-02-25 | 2019-01-30 | 三菱ケミカル株式会社 | α−オレフィン低重合体の製造方法 |
| RU2682668C1 (ru) * | 2015-03-27 | 2019-03-20 | Мицубиси Кемикал Корпорейшн | СПОСОБ ДЛЯ ПРОИЗВОДСТВА НИЗКОМОЛЕКУЛЯРНОГО ПОЛИМЕРА α-ОЛЕФИНА |
| WO2016206911A1 (en) * | 2015-06-23 | 2016-12-29 | Sabic Global Technologies B.V. | Polymerisation of ethylene in the presence of a silylchromate based catalyst |
| WO2020114745A1 (en) | 2018-12-04 | 2020-06-11 | Exxonmobil Chemical Patents Inc. | Methods for separating linear alpha olefins from combined product streams |
| KR102732601B1 (ko) * | 2021-01-18 | 2024-11-19 | 주식회사 엘지화학 | 올리고머 제조방법 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2860126A (en) | 1954-07-09 | 1958-11-11 | Phillips Petroleum Co | Polymerization process |
| US2964511A (en) * | 1956-03-12 | 1960-12-13 | Phillips Petroleum Co | Control of catalytic processes |
| GB855120A (en) | 1956-05-07 | 1960-11-30 | Phillips Petroleum Co | Method of supplying a catalyst to a reaction zone and apparatus therefor |
| US3250757A (en) * | 1961-05-18 | 1966-05-10 | Phillips Petroleum Co | Method and apparatus for controlling feed to a polymerization reaction |
| US4434313A (en) * | 1981-12-14 | 1984-02-28 | Exxon Research And Engineering Co. | Preparation of linear olefin products |
| US5198563A (en) * | 1989-08-10 | 1993-03-30 | Phillips Petroleum Company | Chromium compounds and uses thereof |
| CA2110654C (en) * | 1992-12-17 | 2006-03-21 | Albert Rossi | Dilute process for the polymerization of ethylene/alpha-olefin copolymer using metallocene catalyst systems |
| JP2618589B2 (ja) * | 1993-06-21 | 1997-06-11 | 日本合成アルコール株式会社 | エチレンの回収方法 |
| JPH0760048A (ja) | 1993-08-26 | 1995-03-07 | Mitsubishi Petrochem Eng Co Ltd | 酸化エチレン製造プラント排ガスからのエチレンの回収法 |
| CA2134503C (en) * | 1994-02-18 | 2001-04-10 | Mark E. Lashier | Olefin production |
| JP2756459B2 (ja) * | 1994-05-31 | 1998-05-25 | 日本合成アルコール株式会社 | エチレン水和反応における不純エチレン流の処理方法 |
| KR100414008B1 (ko) * | 1995-03-02 | 2004-04-29 | 미쓰비시 가가꾸 가부시키가이샤 | α-올레핀올리고머의제조방법 |
| JP3847809B2 (ja) | 1995-03-02 | 2006-11-22 | 三菱化学株式会社 | α−オレフイン低重合体の製造方法 |
| US5856612A (en) | 1996-02-02 | 1999-01-05 | Mitsubishi Chemical Corporation | Process for producing α-olefin oligomer |
| JP3549136B2 (ja) * | 1996-07-30 | 2004-08-04 | 三菱化学株式会社 | α−オレフイン低重合体の製造方法 |
| JP3518968B2 (ja) * | 1996-08-08 | 2004-04-12 | 三菱化学株式会社 | α−オレフイン低重合体の製造方法 |
| JPH1171411A (ja) * | 1997-06-26 | 1999-03-16 | Mitsui Chem Inc | プロピレンの重合方法 |
| CA2241573A1 (en) | 1997-06-26 | 1998-12-26 | Hiroshi Nishikawa | Process for propylene polymerization |
| CN1203925A (zh) * | 1997-06-26 | 1999-01-06 | 三井化学株式会社 | 丙烯聚合的方法 |
| JPH1160511A (ja) * | 1997-08-25 | 1999-03-02 | Mitsubishi Chem Corp | α−オレフィン低重合体の製造方法 |
| US20020182124A1 (en) * | 1997-10-14 | 2002-12-05 | William M. Woodard | Olefin production process |
| US6380451B1 (en) * | 1999-12-29 | 2002-04-30 | Phillips Petroleum Company | Methods for restoring the heat transfer coefficient of an oligomerization reactor |
| GB0016895D0 (en) | 2000-07-11 | 2000-08-30 | Bp Chem Int Ltd | Olefin oligomerisation |
| US6593506B1 (en) * | 2000-10-12 | 2003-07-15 | Exxonmobil Chemical Patents Inc. | Olefin recovery in a polyolefin production process |
| JP2002256007A (ja) | 2000-12-26 | 2002-09-11 | Idemitsu Petrochem Co Ltd | α−オレフィン低重合体の製造方法 |
| TWI239941B (en) | 2000-12-26 | 2005-09-21 | Idemitsu Petrochemical Co | Process for producing ethylenic oligomer technical field |
| JP4870269B2 (ja) | 2001-02-23 | 2012-02-08 | 出光興産株式会社 | α−オレフィン低重合体の製造方法 |
| JP4681773B2 (ja) * | 2001-08-28 | 2011-05-11 | 出光興産株式会社 | エチレン低重合体の製造方法 |
| DE10211386A1 (de) | 2002-03-14 | 2003-09-25 | Basf Ag | Verfahren zur Oligomerisierung von Olefinen unter Verwendung eines Cycloalkylalkyl-substituierten Triazacyclohexans |
| EP1491559B1 (en) * | 2002-03-29 | 2007-09-05 | Mitsui Chemicals, Inc. | Method of recycling waste gas in polymer production plant |
| EP2289952B2 (en) | 2004-08-27 | 2020-03-25 | Chevron Phillips Chemical Company LP | Energy efficient polyolefin process |
| FR2884247B1 (fr) * | 2005-04-11 | 2007-05-18 | Inst Francais Du Petrole | Procede et installation pour l'oligomerisation d'olefines mettant en oeuvre une separation membranaire |
| CA2672385C (en) | 2006-12-28 | 2014-10-14 | Mitsubishi Chemical Corporation | Process for production of .alpha.-olefin low polymers using chromium catalyst |
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2007
- 2007-10-22 CA CA2672385A patent/CA2672385C/en active Active
- 2007-10-22 US US12/520,096 patent/US9421534B2/en active Active
- 2007-10-22 CN CN2007800450285A patent/CN101547941B/zh active Active
- 2007-10-22 EA EA200970640A patent/EA024462B1/ru not_active IP Right Cessation
- 2007-10-22 EP EP07830306A patent/EP2098542A4/en not_active Withdrawn
- 2007-10-22 WO PCT/JP2007/070572 patent/WO2008081638A1/ja not_active Ceased
- 2007-10-22 BR BRPI0719595-8A patent/BRPI0719595B1/pt active IP Right Grant
- 2007-12-28 JP JP2007341365A patent/JP5444615B2/ja active Active
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2008
- 2008-12-22 JP JP2008326605A patent/JP2009102363A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| EA024462B1 (ru) | 2016-09-30 |
| JP5444615B2 (ja) | 2014-03-19 |
| EA200970640A1 (ru) | 2010-02-26 |
| EP2098542A4 (en) | 2011-03-09 |
| EP2098542A1 (en) | 2009-09-09 |
| BRPI0719595A2 (pt) | 2013-12-17 |
| US9421534B2 (en) | 2016-08-23 |
| WO2008081638A1 (ja) | 2008-07-10 |
| JP2008179631A (ja) | 2008-08-07 |
| CA2672385A1 (en) | 2008-07-10 |
| BRPI0719595B1 (pt) | 2017-12-26 |
| US20090326297A1 (en) | 2009-12-31 |
| CN101547941A (zh) | 2009-09-30 |
| CN101547941B (zh) | 2011-12-28 |
| JP2009102363A (ja) | 2009-05-14 |
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