JP6503472B2 - オレフィンオリゴマー化反応用触媒システムおよびこれを用いたオレフィンオリゴマー化方法 - Google Patents
オレフィンオリゴマー化反応用触媒システムおよびこれを用いたオレフィンオリゴマー化方法 Download PDFInfo
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- JP6503472B2 JP6503472B2 JP2017546864A JP2017546864A JP6503472B2 JP 6503472 B2 JP6503472 B2 JP 6503472B2 JP 2017546864 A JP2017546864 A JP 2017546864A JP 2017546864 A JP2017546864 A JP 2017546864A JP 6503472 B2 JP6503472 B2 JP 6503472B2
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- Prior art keywords
- chromium
- olefin
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- iii
- catalyst system
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- 239000003054 catalyst Substances 0.000 title claims description 64
- 150000001336 alkenes Chemical class 0.000 title claims description 45
- 238000006384 oligomerization reaction Methods 0.000 title claims description 45
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 title claims description 43
- 238000000034 method Methods 0.000 title claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 68
- 239000003446 ligand Substances 0.000 claims description 55
- VURFVHCLMJOLKN-UHFFFAOYSA-N diphosphane Chemical group PP VURFVHCLMJOLKN-UHFFFAOYSA-N 0.000 claims description 41
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 32
- 229910052804 chromium Inorganic materials 0.000 claims description 32
- 239000011651 chromium Substances 0.000 claims description 22
- 239000004711 α-olefin Substances 0.000 claims description 22
- -1 triisopropylaluminum Chemical compound 0.000 claims description 15
- CPOFMOWDMVWCLF-UHFFFAOYSA-N methyl(oxo)alumane Chemical compound C[Al]=O CPOFMOWDMVWCLF-UHFFFAOYSA-N 0.000 claims description 12
- 239000003426 co-catalyst Substances 0.000 claims description 11
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 10
- 239000005977 Ethylene Substances 0.000 claims description 10
- 239000000178 monomer Substances 0.000 claims description 10
- YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 claims description 6
- BFGKITSFLPAWGI-UHFFFAOYSA-N chromium(3+) Chemical compound [Cr+3] BFGKITSFLPAWGI-UHFFFAOYSA-N 0.000 claims description 5
- 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 5
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 claims description 5
- CMAOLVNGLTWICC-UHFFFAOYSA-N 2-fluoro-5-methylbenzonitrile Chemical compound CC1=CC=C(F)C(C#N)=C1 CMAOLVNGLTWICC-UHFFFAOYSA-N 0.000 claims description 4
- UAIZDWNSWGTKFZ-UHFFFAOYSA-L ethylaluminum(2+);dichloride Chemical compound CC[Al](Cl)Cl UAIZDWNSWGTKFZ-UHFFFAOYSA-L 0.000 claims description 4
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 claims description 4
- 239000007983 Tris buffer Substances 0.000 claims description 3
- WFOOTRPLCMPWIP-UHFFFAOYSA-K chromium(3+) pentanoate Chemical compound [Cr+3].CCCCC([O-])=O.CCCCC([O-])=O.CCCCC([O-])=O WFOOTRPLCMPWIP-UHFFFAOYSA-K 0.000 claims description 3
- 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 3
- IVKVYYVDZLZGGY-UHFFFAOYSA-K chromium(3+);octadecanoate Chemical compound [Cr+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O IVKVYYVDZLZGGY-UHFFFAOYSA-K 0.000 claims description 3
- 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 3
- JYLPOJPHFDVWCY-UHFFFAOYSA-K oxolane;trichlorochromium Chemical compound [Cl-].[Cl-].[Cl-].[Cr+3].C1CCOC1 JYLPOJPHFDVWCY-UHFFFAOYSA-K 0.000 claims description 3
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 claims description 3
- YVSMQHYREUQGRX-UHFFFAOYSA-N 2-ethyloxaluminane Chemical compound CC[Al]1CCCCO1 YVSMQHYREUQGRX-UHFFFAOYSA-N 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
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 claims 1
- 229940070765 laurate Drugs 0.000 claims 1
- 125000005647 linker group Chemical group 0.000 description 37
- 125000004432 carbon atom Chemical group C* 0.000 description 36
- 238000006243 chemical reaction Methods 0.000 description 24
- 239000000126 substance Substances 0.000 description 24
- 230000000694 effects Effects 0.000 description 20
- 238000004519 manufacturing process Methods 0.000 description 15
- 229910052782 aluminium Inorganic materials 0.000 description 13
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 13
- 125000001183 hydrocarbyl group Chemical group 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 125000003118 aryl group Chemical group 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 12
- 239000007787 solid Substances 0.000 description 11
- 239000000203 mixture Substances 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 125000001931 aliphatic group Chemical group 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 7
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 7
- 229910052796 boron Inorganic materials 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000007791 liquid phase Substances 0.000 description 6
- 229910052698 phosphorus Inorganic materials 0.000 description 6
- 230000003197 catalytic effect Effects 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 125000004437 phosphorous atom Chemical group 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- NWIVYGKSHSJHEF-UHFFFAOYSA-N 4-[(4-amino-3,5-diethylphenyl)methyl]-2,6-diethylaniline Chemical compound CCC1=C(N)C(CC)=CC(CC=2C=C(CC)C(N)=C(CC)C=2)=C1 NWIVYGKSHSJHEF-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- 125000002877 alkyl aryl group Chemical group 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 238000002386 leaching Methods 0.000 description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- 150000003254 radicals Chemical group 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- IMFACGCPASFAPR-UHFFFAOYSA-O tributylazanium Chemical compound CCCC[NH+](CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-O 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000004698 Polyethylene Substances 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
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 229920000092 linear low density polyethylene Polymers 0.000 description 3
- 239000004707 linear low-density polyethylene Substances 0.000 description 3
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000011148 porous material Substances 0.000 description 3
- 238000007086 side reaction Methods 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- GWUXLTRGPPIDJA-UHFFFAOYSA-N (4-methylphenyl)alumane Chemical compound CC1=CC=C([AlH2])C=C1 GWUXLTRGPPIDJA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- DXQXWMYUGOTNGJ-UHFFFAOYSA-N [4-(trifluoromethyl)phenyl]boron Chemical compound [B]C1=CC=C(C(F)(F)F)C=C1 DXQXWMYUGOTNGJ-UHFFFAOYSA-N 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 229910052787 antimony Inorganic materials 0.000 description 2
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 229910052785 arsenic Inorganic materials 0.000 description 2
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- XGRJZXREYAXTGV-UHFFFAOYSA-N chlorodiphenylphosphine Chemical compound C=1C=CC=CC=1P(Cl)C1=CC=CC=C1 XGRJZXREYAXTGV-UHFFFAOYSA-N 0.000 description 2
- NMXUZAZJTJAHGK-UHFFFAOYSA-K chromium(3+);dodecanoate Chemical compound [Cr+3].CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O NMXUZAZJTJAHGK-UHFFFAOYSA-K 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- GGSUCNLOZRCGPQ-UHFFFAOYSA-O diethyl(phenyl)azanium Chemical compound CC[NH+](CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-O 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- SHGOGDWTZKFNSC-UHFFFAOYSA-N ethyl(dimethyl)alumane Chemical compound CC[Al](C)C SHGOGDWTZKFNSC-UHFFFAOYSA-N 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000001072 heteroaryl group Chemical group 0.000 description 2
- YIXJRHPUWRPCBB-UHFFFAOYSA-N magnesium nitrate Chemical compound [Mg+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O YIXJRHPUWRPCBB-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methylcyclopentane Chemical compound CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
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- 229910052755 nonmetal Inorganic materials 0.000 description 2
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- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
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- YWWDBCBWQNCYNR-UHFFFAOYSA-O trimethylphosphanium Chemical compound C[PH+](C)C YWWDBCBWQNCYNR-UHFFFAOYSA-O 0.000 description 2
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WCFQIFDACWBNJT-UHFFFAOYSA-N $l^{1}-alumanyloxy(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]O[Al] WCFQIFDACWBNJT-UHFFFAOYSA-N 0.000 description 1
- VKMQKNJWQNCEQV-UHFFFAOYSA-N (4-methylphenyl)boron Chemical compound [B]C1=CC=C(C)C=C1 VKMQKNJWQNCEQV-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- NXORCMNHLWPGPV-UHFFFAOYSA-N 1,6-diphenylhexane-1,6-diamine Chemical compound C=1C=CC=CC=1C(N)CCCCC(N)C1=CC=CC=C1 NXORCMNHLWPGPV-UHFFFAOYSA-N 0.000 description 1
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- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
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- JQPMDTQDAXRDGS-UHFFFAOYSA-N triphenylalumane Chemical compound C1=CC=CC=C1[Al](C=1C=CC=CC=1)C1=CC=CC=C1 JQPMDTQDAXRDGS-UHFFFAOYSA-N 0.000 description 1
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- XDSSGQHOYWGIKC-UHFFFAOYSA-N tris(2-methylpropyl)borane Chemical compound CC(C)CB(CC(C)C)CC(C)C XDSSGQHOYWGIKC-UHFFFAOYSA-N 0.000 description 1
- WSITXTIRYQMZHM-UHFFFAOYSA-N tris(4-methylphenyl)alumane Chemical compound C1=CC(C)=CC=C1[Al](C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 WSITXTIRYQMZHM-UHFFFAOYSA-N 0.000 description 1
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Classifications
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Description
Pは、リン原子であり、
Aは、窒素(N)、砒素(As)、またはアンチモン(Sb)であり、
R1〜R4は、それぞれ独立に、同一または異なって、炭素数1〜20のヒドロカルビル基、ヘテロヒドロカルビル基、またはヒドロカルボヘテリル基であり、
*は、前記2個以上のグループの間を連結するリンカー(L)と結合する部位である。
Pは、リン原子であり、
Nは、窒素原子であり、Pは、窒素原子であり、
R1〜R4およびR1’〜R4’は、それぞれ独立に、同一または異なって、炭素数1〜20のヒドロカルビル基、ヘテロヒドロカルビル基、またはヒドロカルボヘテリル基であり、
Lは、前記2個以上のジホスフィングループの間を連結する炭素数2〜30のヒドロカルビル基またはヘテロヒドロカルビル基である。
クロムソース;および
前記リガンド化合物が担持された支持体を含む。
Pは、リン原子であり、
Aは、窒素(N)、砒素(As)、またはアンチモン(Sb)であり、
R1〜R4は、それぞれ独立に、同一または異なって、炭素数1〜20のヒドロカルビル基、ヘテロヒドロカルビル基、またはヒドロカルボヘテリル基であり、
*は、前記2個以上のグループの間を連結するリンカー(L)と結合する部位である。
Pは、リン原子であり、
Nは、窒素原子であり、Pは、窒素原子であり、
R1〜R4およびR1’〜R4’は、それぞれ独立に、同一または異なって、炭素数1〜20のヒドロカルビル基、ヘテロヒドロカルビル基、またはヒドロカルボヘテリル基であり、
Lは、前記2個以上のジホスフィングループの間を連結する炭素数2〜30のヒドロカルビル基またはヘテロヒドロカルビル基である。
RRは、それぞれ独立に、炭素数1〜5のアルキル基であり、
nは、各環に置換された置換数で、1〜4の整数の範囲内で置換数に応じて異なっていてもよく、
1つの環に結合された複数のRRは、互いに同一または異なっていてもよい。
Qは、前記化学式1で表される、ジホスフィングループを意味し、
Xは、炭素数1〜20のアルキレン、または炭素数6〜14のアリーレンであり、
R5〜R14は、それぞれ独立に、同一または異なって、炭素数1〜20のアルキル基、炭素数2〜20のアルケニル基、炭素数6〜14のアリール基、炭素数7〜18のアルキルアリール基、炭素数7〜18のアリールアルキル基、または炭素数7〜18のアルコキシアリール基であってもよい。
[化学式4]
−[Al(Rx)−O]c−
前記化学式4において、Alは、アルミニウムであり、
Rxは、互いに同一または異なり、それぞれ独立に、ハロゲンラジカル、炭素数1〜20のヒドロカルビルラジカル、またはハロゲンで置換された炭素数1〜20のヒドロカルビルラジカルであり、cは、2以上の整数であり、
[化学式5]
D(Ry)3
前記化学式5において、Dは、アルミニウムまたはボロンであり、Ryは、炭素数1〜20のヒドロカルビルまたはハロゲンで置換された炭素数1〜20のヒドロカルビルであり、
[化学式6]
[L−H]+[Q(E)4]-
前記化学式6において、
Lは、中性ルイス塩基であり、[L−H]+は、ブレンステッド酸であり、Qは、+3形式酸化状態のホウ素またはアルミニウムであり、Eは、それぞれ独立に、1以上の水素原子がハロゲン、炭素数1〜20のヒドロカルビル、アルコキシ官能基またはフェノキシ官能基で置換もしくは非置換の炭素数6〜20のアリール基または炭素数1〜20のアルキル基である。
支持体の準備
シリカ(SP952X、Grace Davison社)を200℃の温度で12時間真空乾燥して、支持体を製造し、アルゴン雰囲気のグローブボックスに保管した。
[製造例1]
[実施例1〜3]
前記製造例1〜3で準備されたリガンド化合物に、クロムソースとして、3価のクロミウムアセテート(224.5mg、0.7mmol)を準備して、それぞれのモル比が1:1となるようにフラスコに入れて、トルエン65mlを添加した。
クロムのモル数に対するリガンド化合物のモル数が2:1となるようにしたことを除けば、前記実施例2と同一に進行させて、固体粉末状の担持触媒を得た。
前記比較製造例1および2で準備されたリガンド化合物を用い、クロムソースとして、3価のクロミウムアセテート0.35mmolを用いたことを除けば、前記実施例と同一に進行させて、固体粉末状の担持触媒を得た。
[実施例1〜3、参考例1、および比較例1および2]
オリゴマー化反応は、機械式撹拌機が装着されており、温度調節が可能で、高圧で駆動可能な、600ml容量の金属合金素材の反応器で行った。
製造例1で製造されたリガンド化合物に対して、支持体に担持させないまま、触媒と助触媒をそれぞれ溶液状態に溶かして用いて、均一液相反応を進行させたことを除けば、前記実施例1と同様の助触媒組成および反応条件で、反応を進行させた。
Claims (11)
- 下記構造式1及び2で表されるリガンド化合物のうちの1つ以上のリガンド化合物;
クロムソース;および
前記リガンド化合物が担持された支持体を含む、オレフィンオリゴマー化反応用触媒システム:
- 前記リガンド化合物に含まれている2個以上のジホスフィングループのうち1以上のジホスフィングループに属した非共有電子対がクロム原子に配位した、請求項1に記載のオレフィンオリゴマー化反応用触媒システム。
- 前記リガンド化合物に含まれている2個以上のジホスフィングループのうち1以上のジホスフィングループが支持体にテザリング(tethering)される形態に形成される、請求項1に記載のオレフィンオリゴマー化反応用触媒システム。
- 前記リガンド化合物のモル数に対するクロム原子のモル数の比が1以下である、請求項1〜3のいずれか1項に記載のオレフィンオリゴマー化反応用触媒システム。
- 前記クロムソースは、クロミウム(III)アセチルアセトネート、クロミウム(III)クロライドテトラヒドロフラン、クロミウム(III)2−エチルヘキサノエート、クロミウム(III)アセテート、クロミウム(III)ブチレート、クロミウム(III)ペンタノエート、クロミウム(III)ラウレート、クロミウム(III)トリス(2,2,6,6−テトラメチル−3.5−ヘプタンインジオネート)、およびクロミウム(III)ステアレートからなる群より選択された1種以上の化合物である、請求項1〜4のいずれか1項に記載のオレフィンオリゴマー化反応用触媒システム。
- 前記支持体に担持された助触媒をさらに含む、請求項1〜5のいずれか1項に記載のオレフィンオリゴマー化反応用触媒システム。
- 前記助触媒は、トリメチルアルミニウム(trimethyl aluminium)、トリエチルアルミニウム(triethyl aluminium)、トリイソプロピルアルミニウム(triisopropyl aluminium)、トリイソブチルアルミニウム(triisobutyl aluminum)、エチルアルミニウムセスキクロライド(ethylaluminum sesquichloride)、ジエチルアルミニウムクロライド(diethylaluminum chloride)、エチルアルミニウムジクロライド(ethylaluminium dichloride)、メチルアルミノキサン(methylaluminoxane)、および改質されたメチルアルミノキサン(modified methylaluminoxane)からなる群より選択された1種以上の化合物である、請求項6に記載のオレフィンオリゴマー化反応用触媒システム。
- 請求項1〜7のいずれか1項に記載の触媒システムの存在下、オレフィン系単量体のオリゴマー化反応を進行させてアルファ−オレフィンを形成する段階を含む、オレフィンのオリゴマー化方法。
- 前記オレフィン系単量体はエチレンである請求項8に記載のオレフィンのオリゴマー化方法。
- 前記オレフィン系単量体のオリゴマー化反応は、5〜200℃の温度で行われる、請求項8または9に記載のオレフィンのオリゴマー化方法。
- 前記オレフィン系単量体のオリゴマー化反応は、1〜300barの圧力で行われる、請求項8〜10のいずれか1項に記載のオレフィンのオリゴマー化方法。
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