ZA200205153B - Olefin production. - Google Patents
Olefin production. Download PDFInfo
- Publication number
- ZA200205153B ZA200205153B ZA200205153A ZA200205153A ZA200205153B ZA 200205153 B ZA200205153 B ZA 200205153B ZA 200205153 A ZA200205153 A ZA 200205153A ZA 200205153 A ZA200205153 A ZA 200205153A ZA 200205153 B ZA200205153 B ZA 200205153B
- Authority
- ZA
- South Africa
- Prior art keywords
- chromium
- pyrrole
- catalyst system
- iii
- mixture
- Prior art date
Links
- 150000001336 alkenes Chemical class 0.000 title claims description 44
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 title claims description 33
- 238000004519 manufacturing process Methods 0.000 title description 14
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 141
- 239000003054 catalyst Substances 0.000 claims description 118
- 239000011651 chromium Substances 0.000 claims description 92
- 229910052804 chromium Inorganic materials 0.000 claims description 73
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 68
- 229910052751 metal Inorganic materials 0.000 claims description 56
- 239000002184 metal Substances 0.000 claims description 56
- 238000000034 method Methods 0.000 claims description 55
- 150000001875 compounds Chemical class 0.000 claims description 54
- 125000000217 alkyl group Chemical group 0.000 claims description 52
- 239000000203 mixture Substances 0.000 claims description 45
- 230000008569 process Effects 0.000 claims description 45
- 238000005829 trimerization reaction Methods 0.000 claims description 38
- -1 chromium carboxylate Chemical class 0.000 claims description 33
- 238000006384 oligomerization reaction Methods 0.000 claims description 29
- LIKMAJRDDDTEIG-UHFFFAOYSA-N n-hexene Natural products CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 claims description 26
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 17
- 239000005977 Ethylene Substances 0.000 claims description 17
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 claims description 15
- PAPNRQCYSFBWDI-UHFFFAOYSA-N 2,5-Dimethyl-1H-pyrrole Chemical compound CC1=CC=C(C)N1 PAPNRQCYSFBWDI-UHFFFAOYSA-N 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- SCCNXKACLAJZAP-UHFFFAOYSA-N chromium(3+);pyrrol-1-ide Chemical compound [Cr+3].C=1C=C[N-]C=1.C=1C=C[N-]C=1.C=1C=C[N-]C=1 SCCNXKACLAJZAP-UHFFFAOYSA-N 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 8
- 239000004711 α-olefin Substances 0.000 claims description 8
- BFGKITSFLPAWGI-UHFFFAOYSA-N chromium(3+) Chemical group [Cr+3] BFGKITSFLPAWGI-UHFFFAOYSA-N 0.000 claims description 7
- 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 7
- UZEDIBTVIIJELN-UHFFFAOYSA-N chromium(2+) Chemical compound [Cr+2] UZEDIBTVIIJELN-UHFFFAOYSA-N 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- FTBATIJJKIIOTP-UHFFFAOYSA-K trifluorochromium Chemical compound F[Cr](F)F FTBATIJJKIIOTP-UHFFFAOYSA-K 0.000 claims description 3
- YRAJNWYBUCUFBD-UHFFFAOYSA-N 2,2,6,6-tetramethylheptane-3,5-dione Chemical compound CC(C)(C)C(=O)CC(=O)C(C)(C)C YRAJNWYBUCUFBD-UHFFFAOYSA-N 0.000 claims description 2
- 229910021556 Chromium(III) chloride Inorganic materials 0.000 claims description 2
- 229910021564 Chromium(III) fluoride Inorganic materials 0.000 claims description 2
- CNIGXAJYMNFRCZ-UHFFFAOYSA-K butanoate;chromium(3+) Chemical compound [Cr+3].CCCC([O-])=O.CCCC([O-])=O.CCCC([O-])=O CNIGXAJYMNFRCZ-UHFFFAOYSA-K 0.000 claims description 2
- QSWDMMVNRMROPK-UHFFFAOYSA-K chromium(3+) trichloride Chemical compound [Cl-].[Cl-].[Cl-].[Cr+3] QSWDMMVNRMROPK-UHFFFAOYSA-K 0.000 claims description 2
- GOCJWSXBGBQVSO-UHFFFAOYSA-K chromium(3+);2,2-dimethylpropanoate Chemical compound [Cr+3].CC(C)(C)C([O-])=O.CC(C)(C)C([O-])=O.CC(C)(C)C([O-])=O GOCJWSXBGBQVSO-UHFFFAOYSA-K 0.000 claims description 2
- NMXUZAZJTJAHGK-UHFFFAOYSA-K chromium(3+);dodecanoate Chemical compound [Cr+3].CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O NMXUZAZJTJAHGK-UHFFFAOYSA-K 0.000 claims description 2
- WYYQVWLEPYFFLP-UHFFFAOYSA-K chromium(3+);triacetate Chemical compound [Cr+3].CC([O-])=O.CC([O-])=O.CC([O-])=O WYYQVWLEPYFFLP-UHFFFAOYSA-K 0.000 claims description 2
- 239000011636 chromium(III) chloride Substances 0.000 claims description 2
- 235000007831 chromium(III) chloride Nutrition 0.000 claims description 2
- XVHFYNOGAFYRJV-UHFFFAOYSA-L chromium(ii) oxalate Chemical compound [Cr+2].[O-]C(=O)C([O-])=O XVHFYNOGAFYRJV-UHFFFAOYSA-L 0.000 claims description 2
- MJSNUBOCVAKFIJ-LNTINUHCSA-N chromium;(z)-4-oxoniumylidenepent-2-en-2-olate Chemical compound [Cr].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O MJSNUBOCVAKFIJ-LNTINUHCSA-N 0.000 claims description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 2
- 150000003233 pyrroles Chemical class 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 2
- 150000001340 alkali metals Chemical class 0.000 claims 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 1
- LCKHOIUMRVRUKY-UHFFFAOYSA-N [Cr+] Chemical compound [Cr+] LCKHOIUMRVRUKY-UHFFFAOYSA-N 0.000 claims 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 40
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 34
- 239000000243 solution Substances 0.000 description 34
- 238000002360 preparation method Methods 0.000 description 27
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 19
- 230000000694 effects Effects 0.000 description 19
- 239000000047 product Substances 0.000 description 18
- 229910052757 nitrogen Inorganic materials 0.000 description 17
- 229910052782 aluminium Inorganic materials 0.000 description 14
- YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 description 13
- 239000000376 reactant Substances 0.000 description 13
- 229920000642 polymer Polymers 0.000 description 11
- 239000003085 diluting agent Substances 0.000 description 10
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 9
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 9
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 8
- 125000005234 alkyl aluminium group Chemical group 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 7
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 7
- NKTOLZVEWDHZMU-UHFFFAOYSA-N 2,5-xylenol Chemical compound CC1=CC=C(C)C(O)=C1 NKTOLZVEWDHZMU-UHFFFAOYSA-N 0.000 description 6
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 6
- 230000008901 benefit Effects 0.000 description 5
- 150000001845 chromium compounds Chemical class 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- 239000011550 stock solution Substances 0.000 description 5
- VYXHVRARDIDEHS-UHFFFAOYSA-N 1,5-cyclooctadiene Chemical compound C1CC=CCCC=C1 VYXHVRARDIDEHS-UHFFFAOYSA-N 0.000 description 4
- 239000004912 1,5-cyclooctadiene Substances 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- 238000006471 dimerization reaction Methods 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- OUYLXVQKVBXUGW-UHFFFAOYSA-N 2,3-dimethyl-1h-pyrrole Chemical compound CC=1C=CNC=1C OUYLXVQKVBXUGW-UHFFFAOYSA-N 0.000 description 3
- LCZUOKDVTBMCMX-UHFFFAOYSA-N 2,5-dimethyl pyrazine Natural products CC1=CN=C(C)C=N1 LCZUOKDVTBMCMX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 230000003247 decreasing effect Effects 0.000 description 3
- SHZIWNPUGXLXDT-UHFFFAOYSA-N ethyl hexanoate Chemical compound CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 3
- UAIZDWNSWGTKFZ-UHFFFAOYSA-L ethylaluminum(2+);dichloride Chemical compound CC[Al](Cl)Cl UAIZDWNSWGTKFZ-UHFFFAOYSA-L 0.000 description 3
- 238000011065 in-situ storage Methods 0.000 description 3
- 239000001282 iso-butane Substances 0.000 description 3
- 239000003446 ligand Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N 1-Heptene Chemical compound CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 2
- SPURMHFLEKVAAS-UHFFFAOYSA-N 1-docosene Chemical compound CCCCCCCCCCCCCCCCCCCCC=C SPURMHFLEKVAAS-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- RYPKRALMXUUNKS-UHFFFAOYSA-N 2-Hexene Natural products CCCC=CC RYPKRALMXUUNKS-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
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical group [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- 125000002015 acyclic group Chemical group 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- UZDWIWGMKWZEPE-UHFFFAOYSA-K chromium(iii) bromide Chemical compound [Cr+3].[Br-].[Br-].[Br-] UZDWIWGMKWZEPE-UHFFFAOYSA-K 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 239000003701 inert diluent Substances 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- CCCMONHAUSKTEQ-UHFFFAOYSA-N octadec-1-ene Chemical compound CCCCCCCCCCCCCCCCC=C CCCMONHAUSKTEQ-UHFFFAOYSA-N 0.000 description 2
- 150000004045 organic chlorine compounds Chemical class 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 2
- QMMOXUPEWRXHJS-UHFFFAOYSA-N pentene-2 Natural products CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 description 2
- ZSKGQVFRTSEPJT-UHFFFAOYSA-N pyrrole-2-carboxaldehyde Chemical compound O=CC1=CC=CN1 ZSKGQVFRTSEPJT-UHFFFAOYSA-N 0.000 description 2
- WRHZVMBBRYBTKZ-UHFFFAOYSA-N pyrrole-2-carboxylic acid Chemical compound OC(=O)C1=CC=CN1 WRHZVMBBRYBTKZ-UHFFFAOYSA-N 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- PRBHEGAFLDMLAL-UHFFFAOYSA-N 1,5-Hexadiene Natural products CC=CCC=C PRBHEGAFLDMLAL-UHFFFAOYSA-N 0.000 description 1
- FRUWMYWEARDNTC-UHFFFAOYSA-N 2,3,3a,4-tetrahydro-1h-indole Chemical compound C1C=CC=C2NCCC21 FRUWMYWEARDNTC-UHFFFAOYSA-N 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- OTTZHAVKAVGASB-HYXAFXHYSA-N 2-Heptene Chemical compound CCCC\C=C/C OTTZHAVKAVGASB-HYXAFXHYSA-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
- OTTZHAVKAVGASB-UHFFFAOYSA-N 2-heptene Natural products CCCCC=CC OTTZHAVKAVGASB-UHFFFAOYSA-N 0.000 description 1
- ZEBBLOXDLGIMEG-UHFFFAOYSA-N 3-ethyl-2,4-dimethyl-1h-pyrrole Chemical compound CCC=1C(C)=CNC=1C ZEBBLOXDLGIMEG-UHFFFAOYSA-N 0.000 description 1
- ZQDPJFUHLCOCRG-UHFFFAOYSA-N 3-hexene Chemical compound CCC=CCC ZQDPJFUHLCOCRG-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 229910021554 Chromium(II) chloride Inorganic materials 0.000 description 1
- 229910021562 Chromium(II) fluoride Inorganic materials 0.000 description 1
- 229910021560 Chromium(III) bromide Inorganic materials 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-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
- DFRNJVLHJQPZCC-UHFFFAOYSA-N [Cs+].C=1C=C[N-]C=1 Chemical compound [Cs+].C=1C=C[N-]C=1 DFRNJVLHJQPZCC-UHFFFAOYSA-N 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
- 230000002411 adverse Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- OJRZMCPJFSNIJV-UHFFFAOYSA-L butanoate;chromium(2+) Chemical compound [Cr+2].CCCC([O-])=O.CCCC([O-])=O OJRZMCPJFSNIJV-UHFFFAOYSA-L 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- HYTFNZKVQXUNQW-UHFFFAOYSA-L chromium(2+);2,2-dimethylpropanoate Chemical compound [Cr+2].CC(C)(C)C([O-])=O.CC(C)(C)C([O-])=O HYTFNZKVQXUNQW-UHFFFAOYSA-L 0.000 description 1
- MFBPBRIDLMRZJL-UHFFFAOYSA-L chromium(2+);2-ethylhexanoate Chemical compound [Cr+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O MFBPBRIDLMRZJL-UHFFFAOYSA-L 0.000 description 1
- FFWNKDUCKICKKQ-UHFFFAOYSA-L chromium(2+);dodecanoate Chemical compound [Cr+2].CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O FFWNKDUCKICKKQ-UHFFFAOYSA-L 0.000 description 1
- MGNZTOJSOXWNCH-UHFFFAOYSA-N chromium(2+);pyrrol-1-ide Chemical class [Cr+2].C=1C=C[N-]C=1.C=1C=C[N-]C=1 MGNZTOJSOXWNCH-UHFFFAOYSA-N 0.000 description 1
- IVKVYYVDZLZGGY-UHFFFAOYSA-K chromium(3+);octadecanoate Chemical compound [Cr+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O IVKVYYVDZLZGGY-UHFFFAOYSA-K 0.000 description 1
- XZQOHYZUWTWZBL-UHFFFAOYSA-L chromium(ii) bromide Chemical compound [Cr+2].[Br-].[Br-] XZQOHYZUWTWZBL-UHFFFAOYSA-L 0.000 description 1
- XBWRJSSJWDOUSJ-UHFFFAOYSA-L chromium(ii) chloride Chemical compound Cl[Cr]Cl XBWRJSSJWDOUSJ-UHFFFAOYSA-L 0.000 description 1
- RNFYGEKNFJULJY-UHFFFAOYSA-L chromium(ii) fluoride Chemical compound [F-].[F-].[Cr+2] RNFYGEKNFJULJY-UHFFFAOYSA-L 0.000 description 1
- 229940109126 chromous chloride Drugs 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- UWAMTZZJXXCIOH-UHFFFAOYSA-M diethyl(phenoxy)alumane Chemical compound CC[Al+]CC.[O-]C1=CC=CC=C1 UWAMTZZJXXCIOH-UHFFFAOYSA-M 0.000 description 1
- JJSGABFIILQOEY-UHFFFAOYSA-M diethylalumanylium;bromide Chemical compound CC[Al](Br)CC JJSGABFIILQOEY-UHFFFAOYSA-M 0.000 description 1
- HQWPLXHWEZZGKY-UHFFFAOYSA-N diethylzinc Chemical group CC[Zn]CC HQWPLXHWEZZGKY-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- LDLDYFCCDKENPD-UHFFFAOYSA-N ethenylcyclohexane Chemical compound C=CC1CCCCC1 LDLDYFCCDKENPD-UHFFFAOYSA-N 0.000 description 1
- GCPCLEKQVMKXJM-UHFFFAOYSA-N ethoxy(diethyl)alumane Chemical compound CCO[Al](CC)CC GCPCLEKQVMKXJM-UHFFFAOYSA-N 0.000 description 1
- IZSBSZYFPYIJDI-UHFFFAOYSA-N ethyl 3,5-dimethyl-1h-pyrrole-2-carboxylate Chemical compound CCOC(=O)C=1NC(C)=CC=1C IZSBSZYFPYIJDI-UHFFFAOYSA-N 0.000 description 1
- ZYNJVGCLOFPWFZ-UHFFFAOYSA-N ethyl 4-(3-ethoxy-3-oxopropyl)-3,5-dimethyl-1h-pyrrole-2-carboxylate Chemical compound CCOC(=O)CCC1=C(C)NC(C(=O)OCC)=C1C ZYNJVGCLOFPWFZ-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010574 gas phase reaction Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- WZHKDGJSXCTSCK-UHFFFAOYSA-N hept-3-ene Chemical compound CCCC=CCC WZHKDGJSXCTSCK-UHFFFAOYSA-N 0.000 description 1
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical compound C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 1
- YUWFEBAXEOLKSG-UHFFFAOYSA-N hexamethylbenzene Chemical compound CC1=C(C)C(C)=C(C)C(C)=C1C YUWFEBAXEOLKSG-UHFFFAOYSA-N 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052809 inorganic oxide Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical group [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical group [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 1
- GHTQTHLNYUEMQK-UHFFFAOYSA-N lithium;pyrrol-1-ide Chemical compound [Li]N1C=CC=C1 GHTQTHLNYUEMQK-UHFFFAOYSA-N 0.000 description 1
- DLPASUVGCQPFFO-UHFFFAOYSA-N magnesium;ethane Chemical group [Mg+2].[CH2-]C.[CH2-]C DLPASUVGCQPFFO-UHFFFAOYSA-N 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
- 150000002739 metals Chemical class 0.000 description 1
- 150000005673 monoalkenes Chemical class 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- QYZLKGVUSQXAMU-UHFFFAOYSA-N penta-1,4-diene Chemical compound C=CCC=C QYZLKGVUSQXAMU-UHFFFAOYSA-N 0.000 description 1
- 229920000098 polyolefin Polymers 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
- DOYOPBSXEIZLRE-UHFFFAOYSA-N pyrrole-3-carboxylic acid Natural products OC(=O)C=1C=CNC=1 DOYOPBSXEIZLRE-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 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
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 229940095068 tetradecene Drugs 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- SQBBHCOIQXKPHL-UHFFFAOYSA-N tributylalumane Chemical compound CCCC[Al](CCCC)CCCC SQBBHCOIQXKPHL-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical group C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- CNWZYDSEVLFSMS-UHFFFAOYSA-N tripropylalumane Chemical compound CCC[Al](CCC)CCC CNWZYDSEVLFSMS-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene 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
- B01J31/04—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing carboxylic acids or their salts
-
- 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
- B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
- B01J31/0235—Nitrogen containing compounds
- B01J31/0244—Nitrogen containing compounds with nitrogen contained as ring member in aromatic compounds or moieties, e.g. pyridine
-
- 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
- B01J31/122—Metal aryl or alkyl compounds
-
- 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
- C07C2/26—Catalytic processes with hydrides or organic compounds
- C07C2/30—Catalytic processes with hydrides or organic compounds containing metal-to-carbon bond; Metal hydrides
-
- 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
- C07C2/32—Catalytic processes with hydrides or organic compounds as complexes, e.g. acetyl-acetonates
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- C07C2527/06—Halogens; Compounds thereof
- C07C2527/132—Compounds comprising a halogen and chromium, molybdenum, tungsten or polonium
-
- 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
-
- 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
- C07C2531/04—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing carboxylic acids or their salts
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- C07C2531/22—Organic complexes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/474,067 US6455648B1 (en) | 1999-12-29 | 1999-12-29 | Olefin production |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200205153B true ZA200205153B (en) | 2003-09-26 |
Family
ID=23882058
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200205153A ZA200205153B (en) | 1999-12-29 | 2002-06-26 | Olefin production. |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US6455648B1 (fr) |
| EP (1) | EP1268570A4 (fr) |
| CN (1) | CN1184240C (fr) |
| AU (1) | AU782085B2 (fr) |
| BR (1) | BR0016881B1 (fr) |
| CA (1) | CA2396614C (fr) |
| CZ (1) | CZ20022227A3 (fr) |
| MX (1) | MXPA02006519A (fr) |
| RU (1) | RU2260578C2 (fr) |
| WO (1) | WO2001048028A1 (fr) |
| ZA (1) | ZA200205153B (fr) |
Families Citing this family (45)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20020182124A1 (en) * | 1997-10-14 | 2002-12-05 | William M. Woodard | Olefin production process |
| JP4371305B2 (ja) | 2002-04-24 | 2009-11-25 | シミックス・ソルーションズ・インコーポレーテッド | 架橋ビス芳香族リガンド、錯体、触媒、または、重合方法およびそれにより得られるポリマー |
| US7060848B2 (en) | 2002-04-24 | 2006-06-13 | Symyx Technologies, Inc. | Bridged bi-aromatic catalysts, complexes, and methods of using the same |
| US7091292B2 (en) | 2002-04-24 | 2006-08-15 | Symyx Technologies, Inc. | Bridged bi-aromatic catalysts, complexes, and methods of using the same |
| TW200502038A (en) * | 2003-03-14 | 2005-01-16 | Chevron Phillips Chemical Co | Process to decrease or eliminate corrosion from the decomposition of halide containing olefin catalysts |
| US20050187418A1 (en) * | 2004-02-19 | 2005-08-25 | Small Brooke L. | Olefin oligomerization |
| US20050187098A1 (en) * | 2004-02-20 | 2005-08-25 | Knudsen Ronald D. | Methods of preparation of an olefin oligomerization catalyst |
| US20070043181A1 (en) * | 2005-08-19 | 2007-02-22 | Knudsen Ronald D | Methods of preparation of an olefin oligomerization catalyst |
| US7384886B2 (en) * | 2004-02-20 | 2008-06-10 | Chevron Phillips Chemical Company Lp | Methods of preparation of an olefin oligomerization catalyst |
| US9550841B2 (en) | 2004-02-20 | 2017-01-24 | Chevron Phillips Chemical Company Lp | Methods of preparation of an olefin oligomerization catalyst |
| EP2287144B1 (fr) * | 2004-02-20 | 2018-04-11 | Chevron Phillips Chemical Company LP | Procédés pour la préparation d'un catalyseur d'oligomérisation d'oléfines |
| JP5448142B2 (ja) * | 2005-03-09 | 2014-03-19 | エクソンモービル・ケミカル・パテンツ・インク | オレフィンのオリゴマー化 |
| US7414006B2 (en) * | 2005-03-09 | 2008-08-19 | Exxonmobil Chemical Patents Inc. | Methods for oligomerizing olefins |
| US8003839B2 (en) * | 2006-02-03 | 2011-08-23 | Exxonmobil Chemical Patents Inc. | Process for generating linear apha olefin comonomers |
| WO2007092136A2 (fr) * | 2006-02-03 | 2007-08-16 | Exxonmobil Chemical Patents, Inc. | Procédé de génération de comonomères d'alpha-oléfine |
| US7982085B2 (en) * | 2006-02-03 | 2011-07-19 | Exxonmobil Chemical Patents Inc. | In-line process for generating comonomer |
| CN100386149C (zh) * | 2006-06-26 | 2008-05-07 | 中国石油天然气股份有限公司 | 一种乙烯三聚催化剂及其应用 |
| US7378537B2 (en) * | 2006-07-25 | 2008-05-27 | Chevron Phillips Chemical Company Lp | Olefin oligomerization catalysts and methods of using same |
| US8404915B2 (en) * | 2006-08-30 | 2013-03-26 | Exxonmobil Chemical Patents Inc. | Phosphine ligand-metal compositions, complexes, and catalysts for ethylene trimerizations |
| DE602007008268D1 (de) * | 2007-12-06 | 2010-09-16 | Linde Ag | Katalysatorzusammensetzung und Verfahren zur Herstellung linearer Alphaolefine |
| US7902415B2 (en) * | 2007-12-21 | 2011-03-08 | Chevron Phillips Chemical Company Lp | Processes for dimerizing or isomerizing olefins |
| US8084659B2 (en) * | 2008-10-22 | 2011-12-27 | Lummus Technology, Inc. | Hexene upgrading |
| KR101642164B1 (ko) * | 2008-10-31 | 2016-07-22 | 셰브론 필립스 케미컬 컴퍼니 엘피 | 금속 전구체 및 올레핀 희석제 조성물 및 촉매시스템 |
| US8471085B2 (en) | 2008-10-31 | 2013-06-25 | Chevron Phillips Chemical Company Lp | Oligomerization catalyst system and process for oligomerizing olefins |
| JP5807325B2 (ja) | 2009-09-30 | 2015-11-10 | 住友化学株式会社 | 遷移金属錯体、該遷移金属錯体の製造方法、三量化用触媒、１−ヘキセンの製造方法、エチレン系重合体の製造方法、置換シクロペンタジエン化合物、及び、該置換シクロペンタジエン化合物の製造方法 |
| RU2430116C1 (ru) | 2010-01-29 | 2011-09-27 | Закрытое Акционерное Общество "Сибур Холдинг" | Способ полимеризации и сополимеризации олефиновых олигомеров |
| SG183230A1 (en) | 2010-03-09 | 2012-09-27 | Exxonmobil Chem Patents Inc | System and method for selective trimerization |
| JP5900089B2 (ja) | 2011-03-29 | 2016-04-06 | 住友化学株式会社 | 遷移金属錯体、該遷移金属錯体の製造方法、三量化用触媒、１−ヘキセンの製造方法、置換シクロペンタジエン化合物、及び、該置換シクロペンタジエン化合物の製造方法 |
| JP2012224617A (ja) * | 2011-03-30 | 2012-11-15 | Sumitomo Chemical Co Ltd | １−ヘキセンの製造方法 |
| US9956548B2 (en) | 2011-12-12 | 2018-05-01 | Chevron Phillips Chemical Company Lp | Preparation of an olefin oligomerization catalyst |
| US8957235B2 (en) | 2011-12-12 | 2015-02-17 | Chevron Phillips Chemical Company Lp | Preparation of transition metal carboxylates |
| US9586872B2 (en) | 2011-12-30 | 2017-03-07 | Chevron Phillips Chemical Company Lp | Olefin oligomerization methods |
| US8524972B1 (en) | 2012-04-18 | 2013-09-03 | Exxonmobil Chemical Patents Inc. | Low temperature steam stripping for byproduct polymer and solvent recovery from an ethylene oligomerization process |
| US9616421B2 (en) | 2013-02-27 | 2017-04-11 | Mitsui Chemicals, Inc. | Catalyst for olefin multimerization and method for producing olefin multimer in presence of catalyst for olefin multimerization |
| US9175109B1 (en) | 2014-05-20 | 2015-11-03 | Chevron Phillips Chemical Company Lp | Oligomerization processes and polymer compositions produced therefrom |
| EA034108B1 (ru) * | 2014-12-23 | 2019-12-27 | Публичное акционерное общество "СИБУР Холдинг" | Способы получения олигомеров олефина |
| US9505675B2 (en) | 2015-02-09 | 2016-11-29 | Chevron Phillips Chemical Company Lp | Deactivation of a process by-product |
| WO2017010998A1 (fr) | 2015-07-14 | 2017-01-19 | Chevron Phillips Chemical Company Lp | Compositions d'oléfines |
| US9732300B2 (en) | 2015-07-23 | 2017-08-15 | Chevron Phillipa Chemical Company LP | Liquid propylene oligomers and methods of making same |
| US10519077B2 (en) | 2015-09-18 | 2019-12-31 | Chevron Phillips Chemical Company Lp | Ethylene oligomerization/trimerization/tetramerization reactor |
| US10513473B2 (en) | 2015-09-18 | 2019-12-24 | Chevron Phillips Chemical Company Lp | Ethylene oligomerization/trimerization/tetramerization reactor |
| CA3043155C (fr) * | 2016-11-14 | 2021-11-16 | Public Joint Stock Company "Sibur Holding" | Systeme catalyseur utilise dans l'oligomerisation d'olefines et procede d'oligomerisation d'olefines |
| FR3112969B1 (fr) | 2020-07-30 | 2022-08-05 | Ifp Energies Now | Nouvelle composition catalytique a base de chrome et procede associe pour la trimerisation de l’ethylene en hexene-1 |
| FR3113054B1 (fr) * | 2020-07-30 | 2022-11-04 | Ifp Energies Now | Procede d’oligomerisation d’ethylene comprenant la preparation in situ de la composition catalytique |
| CN115445666A (zh) * | 2022-09-22 | 2022-12-09 | 中化泉州石化有限公司 | 一种乙烯齐聚制备1-己烯的催化剂组合物及其应用 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL81610A (en) | 1986-02-27 | 1990-12-23 | Roussel Uclaf | Derivatives of 1,2,5,6-tetrahydropyridin-3-carboxaldehyde oxime,their preparation and pharmaceutical compositions containing them |
| US5198563A (en) | 1989-08-10 | 1993-03-30 | Phillips Petroleum Company | Chromium compounds and uses thereof |
| US5331104A (en) | 1989-08-10 | 1994-07-19 | Phillips Petroleum Company | Chromium compounds and uses thereof |
| US5376612A (en) | 1989-08-10 | 1994-12-27 | Phillips Petroleum Company | Chromium catalysts and process for making chromium catalysts |
| EP0548805B1 (fr) | 1991-12-18 | 1997-03-05 | Phillips Petroleum Company | Procédé de préparation d'un catalyseur de polymérisation |
| US5331070A (en) | 1992-11-13 | 1994-07-19 | Phillips Petroleum Company | Process for olefin polymerization |
| CA2134503C (fr) | 1994-02-18 | 2001-04-10 | Mark E. Lashier | Procede pour l'obtention d'olefines |
| JP3766170B2 (ja) * | 1996-03-14 | 2006-04-12 | 三菱化学株式会社 | α−オレフィン低重合体の製造方法 |
| US6133495A (en) * | 1996-03-14 | 2000-10-17 | Mitsubishi Chemical Corporation | Process for producing α-olefin oligomer |
| US5856257A (en) * | 1997-05-16 | 1999-01-05 | Phillips Petroleum Company | Olefin production |
| US20010053742A1 (en) * | 1998-12-18 | 2001-12-20 | Ronald D. Knudsen | Catalyst and processes for olefin trimerization |
-
1999
- 1999-12-29 US US09/474,067 patent/US6455648B1/en not_active Expired - Lifetime
-
2000
- 2000-12-21 CZ CZ20022227A patent/CZ20022227A3/cs unknown
- 2000-12-21 AU AU21118/01A patent/AU782085B2/en not_active Ceased
- 2000-12-21 CA CA002396614A patent/CA2396614C/fr not_active Expired - Fee Related
- 2000-12-21 WO PCT/US2000/035078 patent/WO2001048028A1/fr active IP Right Grant
- 2000-12-21 RU RU2002120488/04A patent/RU2260578C2/ru not_active IP Right Cessation
- 2000-12-21 BR BRPI0016881-5A patent/BR0016881B1/pt not_active IP Right Cessation
- 2000-12-21 MX MXPA02006519A patent/MXPA02006519A/es active IP Right Grant
- 2000-12-21 CN CNB008187479A patent/CN1184240C/zh not_active Expired - Fee Related
- 2000-12-21 EP EP00984513A patent/EP1268570A4/fr not_active Ceased
-
2002
- 2002-06-26 ZA ZA200205153A patent/ZA200205153B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU782085B2 (en) | 2005-06-30 |
| US6455648B1 (en) | 2002-09-24 |
| CN1184240C (zh) | 2005-01-12 |
| CA2396614A1 (fr) | 2001-07-05 |
| EP1268570A4 (fr) | 2004-06-16 |
| AU2111801A (en) | 2001-07-09 |
| RU2260578C2 (ru) | 2005-09-20 |
| RU2002120488A (ru) | 2004-01-10 |
| CZ20022227A3 (cs) | 2003-03-12 |
| WO2001048028A1 (fr) | 2001-07-05 |
| BR0016881B1 (pt) | 2011-05-03 |
| BR0016881A (pt) | 2002-12-03 |
| EP1268570A1 (fr) | 2003-01-02 |
| CA2396614C (fr) | 2007-08-21 |
| CN1433433A (zh) | 2003-07-30 |
| MXPA02006519A (es) | 2002-12-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
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