JP2019522667A - オレフィンのオリゴマー化法 - Google Patents
オレフィンのオリゴマー化法 Download PDFInfo
- Publication number
- JP2019522667A JP2019522667A JP2019501563A JP2019501563A JP2019522667A JP 2019522667 A JP2019522667 A JP 2019522667A JP 2019501563 A JP2019501563 A JP 2019501563A JP 2019501563 A JP2019501563 A JP 2019501563A JP 2019522667 A JP2019522667 A JP 2019522667A
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- JP
- Japan
- Prior art keywords
- group
- oligomerization
- reactor
- transition metal
- zinc
- 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.)
- Granted
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- 238000000034 method Methods 0.000 title claims abstract description 142
- 230000008569 process Effects 0.000 title claims abstract description 70
- 238000006384 oligomerization reaction Methods 0.000 title claims abstract description 69
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 title claims description 17
- 150000001336 alkenes Chemical class 0.000 title abstract description 26
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 claims abstract description 106
- 239000003054 catalyst Substances 0.000 claims abstract description 90
- -1 bicyclic compound Chemical class 0.000 claims abstract description 50
- 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 claims abstract description 48
- 239000002904 solvent Substances 0.000 claims abstract description 47
- 239000000203 mixture Substances 0.000 claims abstract description 42
- 229910052723 transition metal Inorganic materials 0.000 claims abstract description 33
- 150000003624 transition metals Chemical class 0.000 claims abstract description 32
- 150000001875 compounds Chemical class 0.000 claims abstract description 25
- 239000004711 α-olefin Substances 0.000 claims abstract description 24
- 239000012190 activator Substances 0.000 claims abstract description 20
- 125000002619 bicyclic group Chemical group 0.000 claims abstract description 12
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims abstract description 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 3
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims abstract description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 100
- CPOFMOWDMVWCLF-UHFFFAOYSA-N methyl(oxo)alumane Chemical group C[Al]=O CPOFMOWDMVWCLF-UHFFFAOYSA-N 0.000 claims description 39
- 239000011651 chromium Substances 0.000 claims description 36
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 31
- 239000005977 Ethylene Substances 0.000 claims description 30
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims description 30
- 229910052804 chromium Inorganic materials 0.000 claims description 28
- 238000004519 manufacturing process Methods 0.000 claims description 21
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 claims description 20
- 239000011701 zinc Substances 0.000 claims description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 229910052725 zinc Inorganic materials 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 238000002156 mixing Methods 0.000 claims description 14
- 239000012535 impurity Substances 0.000 claims description 13
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 12
- 229910052751 metal Inorganic materials 0.000 claims description 12
- 239000002184 metal Substances 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 150000003752 zinc compounds Chemical class 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 9
- 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 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 238000005829 trimerization reaction Methods 0.000 claims description 8
- 229910052782 aluminium Inorganic materials 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000003944 tolyl group Chemical group 0.000 claims description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- HQWPLXHWEZZGKY-UHFFFAOYSA-N diethylzinc Chemical compound CC[Zn]CC HQWPLXHWEZZGKY-UHFFFAOYSA-N 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 229910052719 titanium Inorganic materials 0.000 claims description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 4
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical group N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- NNBZCPXTIHJBJL-AOOOYVTPSA-N cis-decalin Chemical compound C1CCC[C@H]2CCCC[C@H]21 NNBZCPXTIHJBJL-AOOOYVTPSA-N 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 4
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052735 hafnium Inorganic materials 0.000 claims description 4
- 229910052742 iron Inorganic materials 0.000 claims description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 4
- 229910052759 nickel Inorganic materials 0.000 claims description 4
- 229910052763 palladium Inorganic materials 0.000 claims description 4
- 229910052697 platinum Inorganic materials 0.000 claims description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- NNBZCPXTIHJBJL-MGCOHNPYSA-N trans-decalin Chemical compound C1CCC[C@@H]2CCCC[C@H]21 NNBZCPXTIHJBJL-MGCOHNPYSA-N 0.000 claims description 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 4
- 229910052726 zirconium Inorganic materials 0.000 claims description 4
- 150000001298 alcohols Chemical class 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 150000001414 amino alcohols Chemical class 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 238000010791 quenching Methods 0.000 claims description 3
- 230000000171 quenching effect Effects 0.000 claims description 3
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims description 3
- 238000002604 ultrasonography Methods 0.000 claims description 3
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 claims description 2
- NKFNBVMJTSYZDV-UHFFFAOYSA-N 2-[dodecyl(2-hydroxyethyl)amino]ethanol Chemical compound CCCCCCCCCCCCN(CCO)CCO NKFNBVMJTSYZDV-UHFFFAOYSA-N 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 2
- MSWNPXAVLLPELT-UHFFFAOYSA-N [O-2].[O-2].Cl.Cl.[Cr+4] Chemical compound [O-2].[O-2].Cl.Cl.[Cr+4] MSWNPXAVLLPELT-UHFFFAOYSA-N 0.000 claims description 2
- WDNIVTZNAPEMHF-UHFFFAOYSA-N acetic acid;chromium Chemical compound [Cr].CC(O)=O.CC(O)=O WDNIVTZNAPEMHF-UHFFFAOYSA-N 0.000 claims description 2
- 229910021529 ammonia Inorganic materials 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- AIHSXRNLGMIKRH-UHFFFAOYSA-K chromium(3+) 6,6-diethyloctanoate Chemical compound C(C)C(CCCCC(=O)[O-])(CC)CC.[Cr+3].C(C)C(CCCCC(=O)[O-])(CC)CC.C(C)C(CCCCC(=O)[O-])(CC)CC AIHSXRNLGMIKRH-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
- 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
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000006547 cyclononyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 2
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- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 claims description 2
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- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 claims 1
- 229910021555 Chromium Chloride Inorganic materials 0.000 claims 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 1
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 1
- BFGKITSFLPAWGI-UHFFFAOYSA-N chromium(3+) Chemical compound [Cr+3] BFGKITSFLPAWGI-UHFFFAOYSA-N 0.000 claims 1
- 125000004855 decalinyl group Chemical group C1(CCCC2CCCCC12)* 0.000 claims 1
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- VSZWPYCFIRKVQL-UHFFFAOYSA-N selanylidenegallium;selenium Chemical compound [Se].[Se]=[Ga].[Se]=[Ga] VSZWPYCFIRKVQL-UHFFFAOYSA-N 0.000 description 1
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- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
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- 239000007787 solid Substances 0.000 description 1
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- 125000004434 sulfur atom Chemical group 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 1
- YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 description 1
- 150000003613 toluenes Chemical class 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 1
- LFXVBWRMVZPLFK-UHFFFAOYSA-N trioctylalumane Chemical compound CCCCCCCC[Al](CCCCCCCC)CCCCCCCC LFXVBWRMVZPLFK-UHFFFAOYSA-N 0.000 description 1
- 231100000925 very toxic Toxicity 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- SRWMQSFFRFWREA-UHFFFAOYSA-M zinc formate Chemical compound [Zn+2].[O-]C=O SRWMQSFFRFWREA-UHFFFAOYSA-M 0.000 description 1
- XRWDRJZBEVFJLL-UHFFFAOYSA-N zinc pyrrol-1-ide Chemical compound [Zn++].c1cc[n-]c1.c1cc[n-]c1 XRWDRJZBEVFJLL-UHFFFAOYSA-N 0.000 description 1
- IFNXAMCERSVZCV-UHFFFAOYSA-L zinc;2-ethylhexanoate Chemical compound [Zn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O IFNXAMCERSVZCV-UHFFFAOYSA-L 0.000 description 1
- HEPBQSXQJMTVFI-UHFFFAOYSA-N zinc;butane Chemical compound [Zn+2].CCC[CH2-].CCC[CH2-] HEPBQSXQJMTVFI-UHFFFAOYSA-N 0.000 description 1
- AUGAZENISHMAIK-UHFFFAOYSA-N zinc;methylbenzene Chemical compound [Zn+2].CC1=CC=CC=[C-]1.CC1=CC=CC=[C-]1 AUGAZENISHMAIK-UHFFFAOYSA-N 0.000 description 1
- DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical compound Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 0.000 description 1
Images
Classifications
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- 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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/06—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of zinc, cadmium or mercury
-
- 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
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- 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
- B01J31/128—Mixtures of organometallic 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
- B01J31/1845—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing phosphorus
- B01J31/1875—Phosphinites (R2P(OR), their isomeric phosphine oxides (R3P=O) and RO-substitution derivatives thereof)
- B01J31/188—Amide derivatives thereof
-
- 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
- B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
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Abstract
Description
Ar1Ar2P−N(R)−PAr3Ar4 [式I]
(式中、Ar1〜4は同じであるか異なり、置換又は非置換のC6〜C10アリール基から選択され、Rは直鎖状又は分岐状のC1〜C4アルキル基、置換又は非置換のC6〜C10アリール基、及び置換又は非置換のC3〜C10シクロアルキル基から選択される)
の化合物を含む触媒システムの存在下でのC2〜C4オレフィン類のオリゴマー化によって行われる。
Ar1Ar2P−N(R)−PAr3Ar4
式中、
Ar1−4は、同じでも異なっていてもよく、置換又は非置換のC6〜C10アリール基、例えば、フェニル、トリル、エチルフェニル、クミル、ナフチル、最も好ましくはo−置換基を有さないアルキルアリール、特にp−トリル、m−エチルフェニル、又は非置換フェニルであり;
Rは、直鎖状又は分枝鎖状のC1〜C4アルキル、置換又は非置換のC6〜C10アリール、置換又は非置換のC3〜C10シクロアルキル、例えば、メチル、エチル、プロピル、ブチル、イソブチル、ベンジル、アリル、最も好ましくは1つのα−分岐を有するアルキル、例えば、イソプロピル、sec−ブチル、シクロアルキル、例えば、シクロプロピル、シクロブチル、シクロペンチル、シクロヘキシル、シクロヘプチル、シクロオクチル、シクロノニルなどである。
用いた原料は、メチルアルミノキサン(トルエン中10%溶液)、ホスゲン(トルエン中10%溶液)、クロム(III)アセチルアセトナート(Aldrich社)、シクロヘキシルアミン、及びジフェニルホスフィン(Acros Organics社)だった。
窒素雰囲気下、100mLのジクロロエタン中のシクロヘキシルアミン(1.9g,19.3mmol,1当量)及びトリエチルアミン(3.9g,38.5mmol,2当量)の溶液と共に、ジフェニルクロロホスフィン(8.5g,38.6mmol,2当量)をフラスコに供給した。反応混合物を室温で20時間撹拌した。50mlの量の水を添加し、攪拌し、そして有機層(ジクロロエタン中の溶液)を分液ロート中で分離し、次にセライト500を通して濾過した。その後、溶媒を蒸発させ、30mlのメタノールをその得られた蜂蜜様の物質に添加し、白色結晶が沈殿するまで冷却した。沈殿物を濾別し、減圧下、室温で乾燥させた。得られた化合物は白色結晶性固体(3.7g)である。31P NMR分析:50.7ppm,br; 1H NMR、図1参照されたい。
PNP配位子(179.8mg,0.385mmol)及びクロム(III)アセチルアセトナート(67.1mg,0.192mmol)をトルエン(5ml)中で超音波曝露下にて混合した。トルエン中のMAO(25.5mL,38.5mmol)を添加し、混合直後に、その青緑色の溶液を活性触媒の供給源として用いた。3mlの量の触媒を取り、窒素ボックス中で150mlの無水デカリンと混合した。
試験結果を表1に示す。
プロセスの継続時間が15分であり、溶媒がテトラリン不純物から精製されたデカリンだったことを除いて、例2に記載されたようにプロセスを実施した。
エチルベンゼン(0.5%)、ブチルベンゼン(0.5%)、インダン(0.5%)、及びテトラリン(6%)の不純物を含有する工業用デカリン(1.5L)を、ハイグレードの硫酸(96%溶液、1L)と混合し、室温で24時間激しく撹拌した。その後、攪拌を止め、得られた混合物が分離するようにさせておいた。上層を分離し、分液ロート中で500mLの10%炭酸水素ナトリウム水溶液で2回、そして蒸留水でpH6〜7になるまで洗浄した。次に、その有機相を硫酸ナトリウム上で乾燥し、溶融ナトリウム上で蒸留した。
試験の結果を表1に示す。
この例で用いたデカリンは、例3に記載した手順に従って精製した。
PNP配位子(179.8mg,0.385mmol)及びクロム(III)アセチルアセトナート(67.1mg,0.192mmol)をトルエン(5ml)中、超音波曝露下で混合した。トルエン中のMAO(25.5mL,38.5mmol)、次いでデカリン(20mL)を添加し、20mLのトルエンを真空下で留去した。その青緑色の溶液を活性触媒の供給源として用いた。3mLの量の触媒を取り、窒素ボックス中で150mLの無水デカリンと混合した。
オリゴマー化プロセスは例2に記載したようにして実施した。
試験結果を表1に示す。
用いた溶媒がトルエンであり、配位子が式:(フェニル)2P−N(シクロヘキシル)−P(フェニル)2の化合物であることを除いて、国際公開第2004/056479号に従って、例2に記載したようにプロセスを実施した。
5mLのトルエン中の29.0mgのP−N−P配位子(0.073mmol)の溶液を、15mLのトルエン中のCrCl3(テトラヒドロフラン)3(0.033mmol)の溶液12.4mLを含むシュレンクフラスコ中に仕込んだ。得られた溶液を室温で5分間撹拌し、80℃にて、トルエンとMAO(9.9ミリモル)の混合物を含有する250mlのParr反応器に移した。次にエチレンをその反応器に投入した。反応器内の温度を85℃に維持し、エチレンの圧力を30バールに維持した。反応物質を1100rpmで撹拌した。60分後、エチレンの供給を止め、反応物質を40℃に冷却し、脱ガスした。反応物質を、エタノール及び10%塩酸(HCl)水溶液である失活剤で処理した。得られた混合物のサンプルを無水硫酸ナトリウム上で乾燥し、ガスクロマトグラフィー(GC)により分析した。このアッセイにおいて、ヘプタンを内部標準として使用した。
試験の結果を表1に示す。
シクロヘキサンに不溶であることからクロム(III)アセチルアセトナートをトルエン溶液の形態で反応系に導入したこと以外は、国際公開第2004/056479号にしたがう実施例22に記載されているようにしてプロセスを行った。用いた配位子は式:(フェニル)2P−N(シクロヘキシル)−P(フェニル)2の化合物だった。
例1で得られたP−N−P配位子(0.014mmol)のシクロヘキサン10ml中の溶液5.8mgを、10mLのトルエン中のクロム(III)アセチルアセトナート3.5mg(0.01mmol)の溶液を含むシュレンクフラスコに供給した。得られた溶液を室温で5分間撹拌した。次いで、その溶液及びトルエン中のMAO(2mmol)の7%溶液を、45℃において、シクロヘキサン(170ml)を含有する250mlのParr反応器へ差圧によって添加した。次にエチレンを反応器に投入した。反応物質を撹拌しながら、反応器内の温度を45℃に維持し、エチレンの圧力を45バールに維持した。39分後、エチレンの供給を止め、反応物質を40℃に冷却し、脱ガスした。反応物質を、エタノール及び10%塩酸(HCl)水溶液である失活剤で処理した。得られた混合物のサンプルを無水硫酸ナトリウム上で乾燥し、ガスクロマトグラフィー(GC)により分析した。このアッセイにおいて、ヘプタンを内部標準として使用した。
試験の結果を表1に示す。
PNP配位子(89.9mg,0.192mmol)及びクロム(III)アセチルアセトナート(67.1mg,0.192mmol)をトルエン(5ml)中、超音波曝露下で混合した。トルエン中のMAO(40mL,60.4mmol)を添加し、混合後直ちに、その青緑色溶液を活性触媒の供給源として用いた。3mLの量の触媒を取り、150mLの無水溶媒(デカリン)と混合し、ヘキサン中のジエチル亜鉛の1M溶液(0.38mL、0.38mmol)を窒素ボックス中で添加した。
次いで、混合物を、45℃において、差圧によって、排気された250mlのParr反応器に移した。水素(1気圧)をその反応器に供給し、反応器のジャケット内の冷却剤の循環により、内容物を撹拌下(800rpm)でサーモスタット制御して、温度を43〜47℃の範囲内で安定化させた。次いで、エチレンを最大で41バールの全圧になるように反応器に継続して供給し、反応物を撹拌しながら、ガスが枯渇するにつれて(45〜50℃)、供給を一定圧力で続けた。30分後、エチレンの供給を止め、混合物を30℃に冷却し、脱ガスし、反応混合物を下方のボールバルブを通して排出した。液相を分析した(GC)。
デカリンは例3に開示した手順に従って精製した。
試験の結果を表1に示す。
溶媒と混合する前に触媒システムを2時間窒素雰囲気下に保った以外は例2に記載したようにしてプロセスを実施した。
試験の結果を表1に示す。
ブチルリチウム(2.5M,300ml)を、氷冷下で2時間かけて、THF(216g)及びシクロヘキサン(400g)中のインデン(87g,0.75mol)の溶液に添加し、1時間かけて室温に温め、次いで、シクロヘキサン(100g)中の臭化ブチル(102.8g,0.75mol)の溶液を15分間かけて添加し、50℃で3時間加熱し、次いで25℃で16時間撹拌した。次に、飽和NaCl溶液(200mL)をその混合物に添加し、分液ロート中で震盪し、有機層を分離し、水(200mL)で洗浄し、次いで再び飽和NaCl溶液(200mL)を添加し、硫酸ナトリウム上で乾燥した。有機層をロータリーエバポレーターで300ミリバール/65℃にて蒸発させ、残留物を真空下で蒸留し、120〜130℃/20ミリバールの沸点をもつ主留分を集めた。収量は77gであり、純度は79%であり、不純物(GC−MS)はジブチルインデンだった。
例9の生成物を、精製したデカリン(100g)と混合し、5%Pt−10%Pd−C触媒(10g)上で250〜270℃及び100〜120バールにおいて72時間、水素化した。得られた生成物は2%未満の芳香族化合物を含んでいた(GC−MS)。触媒を濾別し、50mlのデカリンで洗浄し、混合した溶媒を例3において上述したように硫酸を用いた精製にかけ、次いでその混合物を真空下、ナトリウム上で蒸留した。混合物は、デカリン溶液中に、ブチル−パーヒドロインダンの4つのジアステレオマーペアを以下の量で含んでいた:5.4%;10.0%;1.1%;及び3.6%(デカリンの総量 - 74%PID面積)。
インデン(250ml)を5%Pt−10%Pd−C触媒(10g)上で250〜270℃及び100〜120バールにおいて72時間、水素化した。得られた生成物の純度は97%(シス−(69.2%)及びトランス−(26.1%)の異性体の混合物)だった。生成物を、硫酸を用いる精製にかけ、デカリン及びブチルパーヒドロインダンと同様に蒸留した。
PNP配位子(89.9mg,0.192mmol)及びクロム(III)アセチルアセトナート(67.1mg,0.192mmol)を超音波照射下でエチルベンゼン(4ml)中で混合した。トルエン中のMAO(25.5mL,38.5mmol)及びジエチル亜鉛(0.4mL)を添加し、混合後直ちに、その青緑色の溶液を活性触媒の供給源として用いた。3mLの量の触媒(1mgのクロムに相当する)を取り、窒素ボックス中で150mLの無水溶媒と混ぜた。触媒溶液の残りの部分を(−196)℃で凍結させ、合成の直前に0℃に解凍した。
試験の結果を表2に示す(例12.1〜12.4)。
Claims (45)
- 遷移金属源、アルキルアルミノキサンである活性化剤、及び下記式(I):
Ar1Ar2P−N(R)−PAr3Ar4 [式I]
(式中、Ar1〜4は同じであるか異なり、置換又は非置換のC6〜C10アリール基から選択され、
Rは直鎖状又は分岐状のC1〜C4アルキル基、置換又は非置換のC6〜C10アリール基、及び置換又は非置換のC3〜C10シクロアルキル基から選択される)
の化合物を含む触媒システムの存在下でのC2〜C4オレフィンのオリゴマー化によるα−オレフィンの製造方法であって、
前記オリゴマー化のプロセスが、二環式化合物又は複数の二環式化合物の混合物である溶媒中で行われる、製造方法。 - 前記オリゴマー化が三量化又は四量化である、請求項1に記載の方法。
- C2〜C4オレフィンがエチレンである、請求項1に記載の方法。
- 前記遷移金属が、Ti、Zr、Hf、Ni、Cr、Fe、Co、Pd、Pt、及びそれらの組み合わせを含む群から選択される、好ましくは遷移金属がCrである、請求項1に記載の方法。
- 前記遷移金属源が、式:MeXn(式中、Meは、Ti、Zr、Hf、Ni、Cr、Fe、Co、Pd、Pt、及びそれらの組み合わせを含む群から選択される遷移金属であり;Xは有機又は無機置換基であり、互いに同じであるか又は異なり;nは1〜6の整数である)の化合物である、請求項1に記載の方法。
- Xは1〜20個の炭素原子を有する有機置換基であり、かつ、アルキル、アルコキシ、カルボキシル、アセチルアセトナート、アミノ、アミド、及びそれらの組み合わせを含む群から選択される、請求項5に記載の方法。
- Xは無機置換基であり、かつ、遷移金属のハライド、サルフェート、及びオキサイドを含む群から選択される、請求項5に記載の方法。
- 前記遷移金属源が式:CrXnのCr化合物であって、塩化クロム(III)、酢酸クロム(III)、トリス-エチルヘキサン酸クロム(III)、クロム(III)アセチルアセトナート、クロム(III)ピロリド、酢酸クロム(II)、及びクロム(IV)ジオキシドジクロリドを含む群から選択される、請求項5に記載の方法。
- アルキルアルミノキサンがメチルアルミノキサンである、請求項1に記載の方法。
- 二環式化合物がデカリン(デカヒドロナフタレン)である、請求項1に記載の方法。
- デカリンが、シスデカリン、トランスデカリン、又はそれらの混合物である、請求項10に記載の方法。
- デカリンが、30質量%以下の不純物しか含まない、請求項10又は11に記載の方法。
- 触媒システムが亜鉛化合物をさらに含む、請求項1に記載の方法。
- 亜鉛化合物が、アルキル亜鉛化合物、アリール亜鉛化合物、亜鉛アミド、亜鉛の酸素化物(zinc oxygenate)、ハロゲン化亜鉛、及びそれらの組み合わせを含む群から選択される、請求項13に記載の方法。
- 亜鉛化合物が亜鉛金属(Zn)である、請求項13に記載の方法。
- 亜鉛化合物がジエチル亜鉛である、請求項14に記載の方法。
- Ar1〜4が、フェニル、トリル、エチルフェニル、クミル、及びナフチルを含む群から選択されるアルキルアリールである、請求項1に記載の方法。
- Rが、メチル、エチル、プロピル、ブチル、イソブチル、ベンジル、アリル、シクロプロピル、シクロブチル、シクロペンチル、シクロヘキシル、シクロヘプチル、シクロオクチル、及びシクロノニルを含む群から選択される基である、請求項1に記載の方法。
- 触媒システムが、遷移金属源と式(I)の化合物を混合することによって調製され、前記混合が、均質な混合物を調製するために超音波への曝露下で行われ、調製された混合物が続いてアルキルアルミノキサンと混合される、請求項1に記載の方法。
- 触媒システムが均一系又は不均一系である、請求項1に記載の方法。
- 遷移金属源と式(I)の化合物の混合が、ベンゼン、トルエン、エチルベンゼン、キシレン、メシチレン、及びクメン、好ましくはトルエン及びエチルベンゼンを含む群から選択される溶媒中で行われる、請求項19に記載の方法。
- 触媒システムを調製する時に亜鉛化合物を添加することをさらに含む、請求項19に記載の方法。
- 触媒システム中のアルミニウム:遷移金属の比が10:1〜5000:1、好ましくは100:1〜1000:1、最も好ましくは200:1〜500:1である、請求項1に記載の方法。
- 触媒システム中の式(I)の化合物:遷移金属の比が、2:1〜1:2、好ましくは1・5:1〜1:1.5である、請求項1に記載の方法。
- 触媒システム中の亜鉛:遷移金属の比が2:1〜1000:1、好ましくは20:1〜200:1である、請求項13に記載の方法。
- a)触媒システムを二環式化合物又は複数の二環式化合物の混合物である溶媒と混合する工程;
b)得られた混合物をオリゴマー化反応器に供給する工程;及び
c)C2〜C4オレフィンをオリゴマー化反応器に供給し、オリゴマー化を行ってα−オレフィンを調製する工程、
を含む、請求項1〜10のいずれか一項に記載の方法。 - オリゴマー化反応器が、撹拌機を備えた連続式反応器、バッチ式反応器、プラグフロー反応器、及び管状反応器を含む群から選択される、請求項26に記載の方法。
- 触媒システムが、その調製後、60分、好ましくは20分、最も好ましくは5分を超えない時間で添加される、請求項26に記載の方法。
- オリゴマー化が、0〜160℃、好ましくは30〜120℃、最も好ましくは40〜80℃の温度で行われる、請求項26に記載の方法。
- 反応器内でのオリゴマー化の時間が30〜60分である、請求項26に記載の方法。
- 水素ガスを供給することをさらに含む、請求項26に記載の方法。
- デカリン中の芳香族炭化水素の含有量が2質量%以下である、請求項10に記載の方法。
- デカリンが実質的にテトラリンを含まない、請求項10に記載の方法。
- 製造されたα−オレフィンがC5〜C40α−オレフィンを含む、請求項1に記載の方法。
- α−オレフィンが好ましくはヘキセン−1及びオクテン−1を含む、請求項34に記載の方法。
- 反応器からの流出物を100℃〜20℃の温度に、好ましくは95℃未満、90℃未満、85℃未満、80℃未満、75℃未満、70℃未満、65℃未満、60℃未満、55℃未満、50℃未満、45℃未満、40℃未満、35℃未満、30℃未満、又は25℃未満の温度に冷却する工程をさらに含む、請求項26に記載の方法。
- 反応器からの流出物が20〜25℃の温度に冷却される、請求項36に記載の方法。
- 反応器からの流出物を、水、アルコール類、アミン類、アミノアルコール類、及びそれらの混合物を含む群から選択される失活剤で処理する工程をさらに含む、請求項26に記載の方法。
- 失活剤が、メタノール、エタノール、n−プロパノール、イソプロパノール、n−ブタノール、イソブタノール、tert−ブタノール、2−エチルヘキサノール、及びそれらの混合物を含む群から選択される、請求項38に記載の方法。
- 失活剤が、アンモニア、メチルアミン、ジメチルアミン、トリメチルアミン、エチルアミン、ジエチルアミン、トリエチルアミン、トリ−n−プロピルアミン、ジイソプロピルエチルアミン、トリ−n−ブチルアミン、ピペラジン、ピリジン、エチレンジアミン、ジエチレントリアミン、及びそれらの混合物を含む群から選択される、請求項38に記載の方法。
- 失活剤が、エタノールアミン、ジエタノールアミン、トリエタノールアミン、メチルジエタノールアミン、ドデシルジエタノールアミン、1−アミノ−2−プロパノール、及びそれらの混合物を含む群から選択される、請求項38に記載の方法。
- 請求項1〜41のいずれか一項に記載の方法によるC2〜C4オレフィンのオリゴマー化によって製造されるα−オレフィン。
- ヘキセン−1又はオクテン−1である、請求項42に記載のα−オレフィン。
- 請求項1〜41のいずれか一項に記載の方法にしたがいC2〜C4オレフィンのオリゴマー化によってα−オレフィンを製造する方法における、二環式化合物又は複数の二環式化合物の混合物である溶媒の使用。
- 溶媒がデカリンである、請求項44に記載の使用。
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EP3484839A4 (en) | 2020-03-18 |
KR102218261B1 (ko) | 2021-02-23 |
CO2019000907A2 (es) | 2019-02-08 |
US20190144357A1 (en) | 2019-05-16 |
EA039177B1 (ru) | 2021-12-14 |
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CA3030567C (en) | 2021-03-02 |
WO2018012997A1 (en) | 2018-01-18 |
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