WO2017069575A1 - 리간드 화합물, 올레핀 올리고머화용 촉매계, 및 이를 이용한 올레핀 올리고머화 방법 - Google Patents
리간드 화합물, 올레핀 올리고머화용 촉매계, 및 이를 이용한 올레핀 올리고머화 방법 Download PDFInfo
- Publication number
- WO2017069575A1 WO2017069575A1 PCT/KR2016/011919 KR2016011919W WO2017069575A1 WO 2017069575 A1 WO2017069575 A1 WO 2017069575A1 KR 2016011919 W KR2016011919 W KR 2016011919W WO 2017069575 A1 WO2017069575 A1 WO 2017069575A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- compound
- formula
- alkyl
- olefin oligomerization
- catalyst system
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 57
- 150000001336 alkenes Chemical class 0.000 title claims abstract description 41
- 239000003054 catalyst Substances 0.000 title claims abstract description 39
- 238000006384 oligomerization reaction Methods 0.000 title claims abstract description 38
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 title claims abstract description 36
- 238000000034 method Methods 0.000 title claims abstract description 19
- 239000003446 ligand Substances 0.000 title abstract description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 239000000126 substance Substances 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 229910052723 transition metal Inorganic materials 0.000 claims description 8
- 150000003624 transition metals Chemical class 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 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
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000002947 alkylene group Chemical group 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
- 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
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 abstract description 26
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 abstract description 13
- 230000000694 effects Effects 0.000 abstract description 7
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 abstract description 4
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 abstract description 4
- 238000006243 chemical reaction Methods 0.000 description 22
- 239000002253 acid Substances 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 12
- 239000005977 Ethylene Substances 0.000 description 12
- 229910052782 aluminium Inorganic materials 0.000 description 11
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 11
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 10
- 229910052796 boron Inorganic materials 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- CPOFMOWDMVWCLF-UHFFFAOYSA-N methyl(oxo)alumane Chemical class C[Al]=O CPOFMOWDMVWCLF-UHFFFAOYSA-N 0.000 description 9
- -1 polyethylene Polymers 0.000 description 9
- 125000001424 substituent group Chemical group 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 8
- 230000003197 catalytic effect Effects 0.000 description 8
- 239000002904 solvent Substances 0.000 description 7
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000011651 chromium Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 6
- 229910052736 halogen Inorganic materials 0.000 description 5
- 150000002367 halogens Chemical class 0.000 description 5
- 150000002500 ions Chemical class 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000004711 α-olefin Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 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
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 4
- YOPIHDSNQOMRGC-UHFFFAOYSA-N 2-benzylcyclohexan-1-amine Chemical compound NC1CCCCC1CC1=CC=CC=C1 YOPIHDSNQOMRGC-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 229910052804 chromium Inorganic materials 0.000 description 3
- 239000012442 inert solvent 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
- 229920000642 polymer Polymers 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 125000003277 amino group Chemical group 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
- 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 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 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
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 2
- 230000003606 oligomerizing effect Effects 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- YWWDBCBWQNCYNR-UHFFFAOYSA-O trimethylphosphanium Chemical compound C[PH+](C)C YWWDBCBWQNCYNR-UHFFFAOYSA-O 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-O triphenylphosphanium Chemical compound C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-O 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
- SMYMJHWAQXWPDB-UHFFFAOYSA-N (2,4,5-trichlorophenoxy)acetic acid Chemical compound OC(=O)COC1=CC(Cl)=C(Cl)C=C1Cl SMYMJHWAQXWPDB-UHFFFAOYSA-N 0.000 description 1
- SXEPDZQVJGZPGF-UHFFFAOYSA-N 1-benzylcyclohexan-1-amine Chemical compound C=1C=CC=CC=1CC1(N)CCCCC1 SXEPDZQVJGZPGF-UHFFFAOYSA-N 0.000 description 1
- YVSMQHYREUQGRX-UHFFFAOYSA-N 2-ethyloxaluminane Chemical compound CC[Al]1CCCCO1 YVSMQHYREUQGRX-UHFFFAOYSA-N 0.000 description 1
- IUUHHWALHWRYPY-UHFFFAOYSA-N 2-propan-2-ylcyclohexan-1-amine Chemical compound CC(C)C1CCCCC1N IUUHHWALHWRYPY-UHFFFAOYSA-N 0.000 description 1
- 239000007848 Bronsted acid Substances 0.000 description 1
- JKUCZICORCIYOT-UHFFFAOYSA-M C(C)(C)[Al](C(C)C)C(C)C.C(C)[Al](Cl)CC Chemical compound C(C)(C)[Al](C(C)C)C(C)C.C(C)[Al](Cl)CC JKUCZICORCIYOT-UHFFFAOYSA-M 0.000 description 1
- LEUIHGAIKJLVHR-UHFFFAOYSA-N C(CCC)B(CCCC)CCCC.C(CC)B(CCC)CCC Chemical compound C(CCC)B(CCCC)CCCC.C(CC)B(CCC)CCC LEUIHGAIKJLVHR-UHFFFAOYSA-N 0.000 description 1
- 0 C*N([C@@](CCCC1)C1(C)C1C)P1(c1ccccc1)c1ccccc1 Chemical compound C*N([C@@](CCCC1)C1(C)C1C)P1(c1ccccc1)c1ccccc1 0.000 description 1
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 description 1
- PLGVIJOQDDMWAO-UHFFFAOYSA-N CCCCN(CCCC)CCCC.FC(C(F)=C(C([Al+2])=C1F)F)=C1F.FC(C(F)=C(C([Al+2])=C1F)F)=C1F.FC(C(F)=C(C([Al+2])=C1F)F)=C1F.FC(C(F)=C(C([Al+2])=C1F)F)=C1F Chemical compound CCCCN(CCCC)CCCC.FC(C(F)=C(C([Al+2])=C1F)F)=C1F.FC(C(F)=C(C([Al+2])=C1F)F)=C1F.FC(C(F)=C(C([Al+2])=C1F)F)=C1F.FC(C(F)=C(C([Al+2])=C1F)F)=C1F PLGVIJOQDDMWAO-UHFFFAOYSA-N 0.000 description 1
- HFEVWLDHPOCPTP-UHFFFAOYSA-N CCNCC.FC(C(F)=C(C([Al+2])=C1F)F)=C1F.FC(C(F)=C(C([Al+2])=C1F)F)=C1F.FC(C(F)=C(C([Al+2])=C1F)F)=C1F.FC(C(F)=C(C([Al+2])=C1F)F)=C1F Chemical compound CCNCC.FC(C(F)=C(C([Al+2])=C1F)F)=C1F.FC(C(F)=C(C([Al+2])=C1F)F)=C1F.FC(C(F)=C(C([Al+2])=C1F)F)=C1F.FC(C(F)=C(C([Al+2])=C1F)F)=C1F HFEVWLDHPOCPTP-UHFFFAOYSA-N 0.000 description 1
- YCPAANODUKMQCJ-UHFFFAOYSA-M C[Al](CC(C)C)C.C[Al](Cl)C Chemical compound C[Al](CC(C)C)C.C[Al](Cl)C YCPAANODUKMQCJ-UHFFFAOYSA-M 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 229910021556 Chromium(III) chloride Inorganic materials 0.000 description 1
- 101150029544 Crem gene Proteins 0.000 description 1
- 239000002879 Lewis base Substances 0.000 description 1
- 229920010126 Linear Low Density Polyethylene (LLDPE) Polymers 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 101100230601 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) HBT1 gene Proteins 0.000 description 1
- 102100030326 Serpin B4 Human genes 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000005234 alkyl aluminium group Chemical group 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229910052787 antimony Chemical group 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical group [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical group [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 229960000359 chromic chloride Drugs 0.000 description 1
- QSWDMMVNRMROPK-UHFFFAOYSA-K chromium(3+) trichloride Chemical compound [Cl-].[Cl-].[Cl-].[Cr+3] QSWDMMVNRMROPK-UHFFFAOYSA-K 0.000 description 1
- WUZCBSQKHJJABD-YNEVXYPXSA-K chromium(3+);(z)-3-oxo-1-phenylbut-1-en-1-olate Chemical compound [Cr+3].CC(=O)\C=C(/[O-])C1=CC=CC=C1.CC(=O)\C=C(/[O-])C1=CC=CC=C1.CC(=O)\C=C(/[O-])C1=CC=CC=C1 WUZCBSQKHJJABD-YNEVXYPXSA-K 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- MRVZZQOTPSZIJV-UHFFFAOYSA-N cyclohexanamine Chemical compound NC1CCCCC1.NC1CCCCC1 MRVZZQOTPSZIJV-UHFFFAOYSA-N 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- MYBJXSAXGLILJD-UHFFFAOYSA-N diethyl(methyl)alumane Chemical compound CC[Al](C)CC MYBJXSAXGLILJD-UHFFFAOYSA-N 0.000 description 1
- GGSUCNLOZRCGPQ-UHFFFAOYSA-O diethyl(phenyl)azanium Chemical compound CC[NH+](CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-O 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-O diethylammonium Chemical compound CC[NH2+]CC HPNMFZURTQLUMO-UHFFFAOYSA-O 0.000 description 1
- ORVACBDINATSAR-UHFFFAOYSA-N dimethylaluminum Chemical compound C[Al]C ORVACBDINATSAR-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- SHGOGDWTZKFNSC-UHFFFAOYSA-N ethyl(dimethyl)alumane Chemical compound CC[Al](C)C SHGOGDWTZKFNSC-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910021482 group 13 metal Inorganic materials 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- 108010013554 leupin Proteins 0.000 description 1
- 150000007527 lewis bases Chemical class 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000007523 nucleic acids Chemical class 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 150000002902 organometallic compounds Chemical group 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003623 transition metal compounds Chemical class 0.000 description 1
- SQBBHCOIQXKPHL-UHFFFAOYSA-N tributylalumane Chemical compound CCCC[Al](CCCC)CCCC SQBBHCOIQXKPHL-UHFFFAOYSA-N 0.000 description 1
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical compound CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 1
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 238000005829 trimerization reaction Methods 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- WXRGABKACDFXMG-UHFFFAOYSA-N trimethylborane Chemical compound CB(C)C WXRGABKACDFXMG-UHFFFAOYSA-N 0.000 description 1
- 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
- CNWZYDSEVLFSMS-UHFFFAOYSA-N tripropylalumane Chemical compound CCC[Al](CCC)CCC CNWZYDSEVLFSMS-UHFFFAOYSA-N 0.000 description 1
- 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
- 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
- B01J31/12—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
- C07C11/00—Aliphatic unsaturated hydrocarbons
- C07C11/02—Alkenes
- C07C11/107—Alkenes with six carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/24—Esteramides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/66—Arsenic compounds
- C07F9/70—Organo-arsenic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/90—Antimony compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
- C08F4/62—Refractory metals or compounds thereof
- C08F4/69—Chromium, molybdenum, tungsten or compounds thereof
Definitions
- the present invention relates to a ligand compound, a catalyst system for olefin oligomerization, and an olefin oligomerization method using the same.
- Linear alpha-olef in is an important material used in comonomers, detergents, lubricants, plasticizers, etc., and is widely used commercially.
- 1-nuxene and 1-octene are polyethylene in the production of linear low density polyethylene (LLDPE). It is widely used as a comonomer for controlling the density of.
- LLDPE Linear Low-Densi ty Polyethylene
- Conventional LLDPE Linear Low-Densi ty Polyethylene
- alpha olefins to control the density (densi ty) by forming a branch (branch) in the polymer backbone with ethylene, for example
- branch branch
- copolymerization with comonomers such as 1-nuxene and 1-octene was performed.
- the present invention is to provide a novel ligand compound capable of limerizing olefins with high catalytic activity and selectivity, a catalyst system for olefin oligomerization comprising the same, and an olefin oligomerization method using the same.
- the present invention provides a compound represented by the following formula (1) or (2).
- Ri to R4 are each independently alkyl; C 3 — 6 cycloalkyl unsubstituted or substituted with d- 10 alkyl, or 10 alkoxy; Substituted by unsubstituted or substituted d- 'w-alkyl, or alkoxy CHQ C 6 - 20 aryl; Or unsubstituted or d- 10 alkyl, or the alkoxylated captured substituted C 5 - 20, and heteroaryl,
- 3 ⁇ 4 is Cwo alkyl; Unsubstituted or d- 10 alkyl, d- or 10 alkoxy C 3 -6 cycloalkyl optionally substituted with; Substituted by unsubstituted or substituted d- 10 alkyl, alkoxy or d- 10 C 6 - 20 aryl; 20 is a heteroaryl group, - or unsubstituted C 5 substituted with unsubstituted or alkyl, alkoxy or Cwo X is a bond or d- 5 alkylene.
- the present invention relates to a ligand compound constituting a catalyst system for olefin oligomerization with a transition metal source and a promoter.
- the compound represented by Chemical Formula 1 or 2 is a ligand compound of the PNP type, and a specific substituent is substituted for phosphorus and nitrogen to impart steric bulk, thereby allowing selective olefin oligomerization.
- the term 'olefin oligomerization' used in the present invention means that olefins are micropolymerized.
- trimer i zat ion and tetramer i zat ion which is collectively called multimer i zat ion.
- the present invention means the selective preparation of 1-hexene and 1-octene, the main comonomers of LLDPE, from ethylene. This selective olefin oligomerization reaction is closely related to the catalyst system used.
- the catalyst system used during the olefin oligomerization reaction includes a transition metal source serving as a main catalyst and a cocatalyst, wherein the structure of the active catalyst can be changed according to the chemical structure of the ligand, and thus the olefin selectivity It may appear different.
- the compound represented by Formula 1 or 2 is characterized in that the substituent of - ⁇ ( ⁇ 3 ⁇ 43 ⁇ 4) ( ⁇ 3 ⁇ 43 ⁇ 4) and the substituent of -XR 5 is substituted in the trans form.
- the ci s and trans forms have different reaction properties during the ligomerization reaction and are due to the difference in the coordination form with the transition metal depending on the structure of the ligand.
- the trans-type ligand is used for olefin oligomerization, thereby increasing oligomerization activity and increasing selectivity of 1-nuxene and 1-octene.
- Ri to the same as each other is preferred.
- R1 to 3 ⁇ 4 are all phenyl.
- -XR 5 can be prepared in the trans form by the steric hindrance with- ⁇ PR ⁇ sKPRsR, so the larger the size thereof is easier to prepare the trans form.
- 3 ⁇ 4 is ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, pentyl, isopentyl, neopentyl, tert-pentyl, sec-pentyl, 3-pentyl, cyclopropyl, cyclobutyl, cyclopentyl , Cyclonuclear chamber, cyclosubstituted methyl substituted, or phenyl.
- X is a bond or methylene (-CH 2- ). Also preferably, 3 ⁇ 4 is c 3 - 6 cycloalkyl, or c 6 _ 20 aryl, X is methylene. Also preferably, R 5 is d- 10 alkyl, or C 3 - 6 cycloalkyl, and, X is a bond.
- Representative examples of the compound represented by Formula 1 or Formula 2 are as follows:
- X and R to R 5 are the same as defined above, and X 'denotes a substituent which is banned upon reaction with the amine of the starting material, respectively.
- Halogen is mentioned as an example of the leaving substituent, Preferably it is chloro.
- the order of the first step and the second step in the reaction formula 1 may be changed, and when the ⁇ - ⁇ 3 ⁇ 43 ⁇ 4 and X-PR 3 R4 are the same, the second step may be omitted.
- the solvent for the reaction dichloromethane is preferable, and reaction is preferably performed in the presence of triethylamine.
- the compound represented by the formula (5) is prepared by reacting the amine group of the compound represented by the formula (3) as a starting material and the compound represented by the formula (4). Subsequently, by the second reaction, the amine group of the compound represented by the formula (5) and the compound represented by the formula (6) react to the formula (1) or (2).
- the compound represented can be prepared.
- a trans-type compound is prepared by the steric hindrance of the compound represented by the formula (5) by a substituent of XR 5 , such as the compound represented by the formula (1) or (2), and the compound of the ci s form is substantially It is not manufactured.
- the final product may further include the step of removing it from the product, since unburned substances (compounds represented by Formulas 3, 4 and 6), intermediates (compounds represented by Formula 5), and other salt compounds remain in the final product.
- the removal may use a method conventionally used in the art. For example, in order to remove a salt compound, a polar solvent (eg, THF) is first added and separated, and then a solvent (eg, acetonitrile) capable of dissolving remaining substances other than the compounds represented by Formulas 1 and 2 is obtained. Can be removed and removed.
- a polar solvent eg, THF
- a solvent eg, acetonitrile
- the present invention provides a catalyst system for olefin oligomerization, comprising a compound represented by Formula 1 or Formula 2, a transition metal source, and a promoter.
- a catalyst system for olefin oligomerization comprising a compound represented by Formula 1 or Formula 2, a transition metal source, and a promoter.
- the catalyst system for olefin oligomerization may include both the compound represented by Formula 1 and the compound represented by Formula 2.
- the catalyst system for olefin oligomerization may include two or more compounds represented by Formula 1 or Formula 2.
- the transition metal source of the olefin oligomerization catalyst system of the embodiment serves as a main catalyst, chromium (III) acetylacetonate, chromium trichloride trihydrotrafuran, chromium ( ⁇ ) -2-ethylnucleoate, Crem (III) tris (2,2,6,6-tetramethyl-3,5-heptanedionate), It is preferably at least one selected from the group consisting of chromium (III) benzoylacetonate, crumb (III) nucleofluoro-2,4-pentanedionate, and crumb (III) acetate hydroxide.
- the cocatalyst is not particularly limited as long as it is an organometallic compound including a Group 13 metal, and can be generally used in the multiplication of leupine under a catalyst of a transition metal compound.
- the promoter may be any one or more selected from the group consisting of compounds represented by the following formulas (3) to (5):
- R 6 are each independently halogen, d-20 alkyl, or haloalkyl, c is an integer of 2 or more,
- D is aluminum or boron
- R 7 is each independently hydrogen, halogen, hydrocarbyl or d- 20 hydrocarbyl substituted with halogen,
- L is a neutral Lewis base
- Q is Br 3+ , or Al 3+ ,
- E are each independently a C 6 - 20 aryl, and, or d- 20 alkyl, wherein the
- C 6 -20 aryl or alkyl is substituted with one or more substituents selected from the group consisting of unsubstituted or substituted by halogen, alkyl, Ci-20 alkoxy, and phenoxy.
- substituents selected from the group consisting of unsubstituted or substituted by halogen, alkyl, Ci-20 alkoxy, and phenoxy.
- MMA0 modified methyl aluminoxane
- MA0 methyl aluminoxane
- ethyl aluminoxane isobutyl aluminoxane
- butyl aluminoxane isobutyl aluminoxane and the like.
- Examples of the compound represented by the formula (5) include triethylammonium tetraphenylboron, tributylammonium tetraphenylboron, trimethylammonium tetraphenylboron, tripropylammonium tetraphenylboron, and trimethylammonium tetra (P).
- Triphenyl phosphonium tetraphenyl boron Trimethyl phosphonium tetraphenyl boron, triethyl ammonium tetraphenyl aluminum, tributyl ammonium tetraphenyl aluminum, Trimethylammonium tetraphenylaluminum ,
- Triphenylphosphonium tetraphenylaluminum Trimethylphosphonium tetraphenylaluminum, triphenylcarbonium tetraphenylboron, triphenylcarbonium tetraphenylaluminum, triphenylcarbonium tetra ( ⁇ -trifluoromethylphenyl) boron,
- aluminoxane may be used as a cocatalyst of the olefinic oligomerization catalyst system of the above embodiment, and more preferably, methylaluminoxane (MA0) or modified methylaluminoxane (MMA0) may be used.
- the catalyst system for olefin oligomerization is a molar ratio of the compound represented by the formula (1) or (2): a transition metal source: a promoter to increase the selectivity to linear alpha olefins, in particular, 1-nuxene and 1-octene, and increase reaction properties.
- a catalyst system comprising a compound represented by Formula 1 or Formula 2, a transition metal source, and a cocatalyst, the three components of the catalyst system are simultaneously or sequentially in any order, with or without monomers in any suitable solvent. Can be added together to obtain an active catalyst.
- suitable Solvents include, but are not limited to, heptane, toluene cyclonucleic acid, methylcyclonucleic acid, 1-nuxene, diethyl ether, tetrahydrofuran, acetonitrile, dichloromethane, chloroform, chlorobenzene, methane, acetone, and the like.
- a method for producing an olefin oligomer comprising the step of multimerizing the olefin in the presence of the catalyst system for ' olefin oligomerization.
- the catalyst system for olefin oligomerization of the above embodiment it is possible to provide a method for oligomerization of olefins having improved reaction activity and selectivity.
- the olefin is a C 2 - 10 alkenyl, preferably C 2 - 10 alpha-olefin to a power law and most preferably is ethylene.
- the olefin oligomerization according to the present invention is a slurry in which a homogeneous liquid reaction, in which the catalyst system is not partially dissolved or completely dissolved in the presence or absence of an inert solvent, is carried out using a conventional apparatus and contacting technique with the catalyst system for olefin oligomerization.
- the olepin oligomerization reaction may be carried out in any inert solvent that does not react with the catalyst compound and the active agent.
- suitable inert solvents include, but are not limited to, benzene, toluene, xylene, cumene, heptane, cyclonucleic acid, methylcyclonucleic acid, methylcyclopentane, nucleic acid, pentane, butane, isobutane and the like. Wherein the solvent is treated with a small amount of alkylaluminum.
- the olepin oligomerization reaction may be performed at a temperature of about 5 ° C to about 200 ° C, preferably at a temperature of about 30 ° C to about 150 ° C.
- the olefin oligomerization reaction may be carried out at a pressure of about 1 bar to about 300 bar, preferably at a pressure of about 2 bar to about 150 bar.
- the catalyst system comprising the compound according to the present invention is capable of oligomerizing ethylene with higher catalytic activity and selectivity compared to the conventional catalyst system.
- a white solid was obtained in the same manner as in Example 1 except for using (cyclohexylmethyl) cyclohexaneamine).
- a white solid was obtained in the same manner as in Example 1 except for using 2-isopropylcyclohexaneamine instead of 2-benzylcyclonucleic acid amine.
- the catalytic activity and the components of the product were analyzed by the GC analysis, and the results are shown in Table 1 below.
- the catalytic activity was divided by the number of moles of Cr and the oligomerization reaction time using the total weight of the product, and the content of 1-nuxene and 1-octene in the product as HA0 and the content of C6-i and other C6-i somer in the product as C6-i. As so, the content of C8-i somer other than 1-octene was analyzed by C8-i so.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Abstract
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201680004226.6A CN107001398A (zh) | 2015-10-21 | 2016-10-21 | 配体化合物、用于烯烃低聚的催化剂体系以及使用该催化剂体系的使烯烃低聚的方法 |
EP16857832.6A EP3214087B1 (en) | 2015-10-21 | 2016-10-21 | Ligand compound, catalyst system for olefin oligomerization, and olefin oligomerization method using same |
JP2017522356A JP6453458B2 (ja) | 2015-10-21 | 2016-10-21 | リガンド化合物、オレフィンオリゴマー化用触媒系、およびこれを用いたオレフィンオリゴマー化方法 |
US15/527,898 US10287373B2 (en) | 2015-10-21 | 2016-10-21 | Ligand compound, catalyst system for olefin oligomerization, and method for oligomerizing olefins using the same |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR20150146843 | 2015-10-21 | ||
KR10-2015-0146843 | 2015-10-21 | ||
KR10-2016-0015301 | 2016-02-05 | ||
KR1020160015301A KR101761830B1 (ko) | 2015-10-21 | 2016-02-05 | 리간드 화합물, 올레핀 올리고머화용 촉매계, 및 이를 이용한 올레핀 올리고머화 방법 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2017069575A1 true WO2017069575A1 (ko) | 2017-04-27 |
Family
ID=58557512
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/KR2016/011919 WO2017069575A1 (ko) | 2015-10-21 | 2016-10-21 | 리간드 화합물, 올레핀 올리고머화용 촉매계, 및 이를 이용한 올레핀 올리고머화 방법 |
Country Status (1)
Country | Link |
---|---|
WO (1) | WO2017069575A1 (ko) |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2008014139A2 (en) * | 2006-07-25 | 2008-01-31 | Chevron Phillips Chemical Company Lp | Olefin oligomerization catalysts and methods of using same |
KR20130142151A (ko) * | 2010-12-29 | 2013-12-27 | 셰브론 필립스 케미컬 컴퍼니 엘피 | 올레핀 올리고머화 촉매 및 제조 및 사용방법 |
KR20150058049A (ko) * | 2013-11-18 | 2015-05-28 | 주식회사 엘지화학 | 리간드 화합물, 올레핀 올리고머화용 촉매계, 및 이를 이용한 올레핀 올리고머화 방법 |
WO2015083053A1 (en) * | 2013-12-05 | 2015-06-11 | Nova Chemicals (International) S.A. | Ethylene oligomerization with mixed ligands |
-
2016
- 2016-10-21 WO PCT/KR2016/011919 patent/WO2017069575A1/ko active Application Filing
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2008014139A2 (en) * | 2006-07-25 | 2008-01-31 | Chevron Phillips Chemical Company Lp | Olefin oligomerization catalysts and methods of using same |
KR20130142151A (ko) * | 2010-12-29 | 2013-12-27 | 셰브론 필립스 케미컬 컴퍼니 엘피 | 올레핀 올리고머화 촉매 및 제조 및 사용방법 |
KR20150058049A (ko) * | 2013-11-18 | 2015-05-28 | 주식회사 엘지화학 | 리간드 화합물, 올레핀 올리고머화용 촉매계, 및 이를 이용한 올레핀 올리고머화 방법 |
WO2015083053A1 (en) * | 2013-12-05 | 2015-06-11 | Nova Chemicals (International) S.A. | Ethylene oligomerization with mixed ligands |
Non-Patent Citations (1)
Title |
---|
KUHLMANN, S. ET AL.: "N-substituted Diphosphinoamines: Toward Rational Ligand Design for the Efficient Tetramerization of Ethylene", vol. 245, no. 2, 2007, pages 279 - 284, XP005755888, Retrieved from the Internet <URL:JournalofCatalysis> * |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP6153278B2 (ja) | リガンド化合物、オレフィンオリゴマー化用触媒系、およびこれを用いたオレフィンオリゴマー化方法 | |
JP5954914B2 (ja) | リガンド化合物、オレフィンオリゴマー化用触媒系、およびこれを用いたオレフィンオリゴマー化方法 | |
JP6247758B2 (ja) | リガンド化合物、オレフィンオリゴマー化用触媒系、およびこれを用いたオレフィンオリゴマー化方法 | |
JP6126741B2 (ja) | リガンド化合物、オレフィンオリゴマー化用触媒系、およびこれを用いたオレフィンオリゴマー化方法 | |
JP6506848B2 (ja) | リガンド化合物、オリゴマー化触媒系およびこれを利用したオレフィンオリゴマー化方法 | |
US9643170B2 (en) | Ligand compound, catalyst system for olefin oligomerization, and method for olefin oligomerization using the same | |
JP6524330B2 (ja) | 1−オクテン組成物 | |
WO2015072810A1 (ko) | 리간드 화합물, 올레핀 올리고머화용 촉매계, 및 이를 이용한 올레핀 올리고머화 방법 | |
JP6389332B2 (ja) | リガンド化合物、オレフィンオリゴマー化用触媒系、およびこれを用いたオレフィンオリゴマー化方法 | |
WO2016195168A1 (ko) | 1-옥텐 조성물 | |
WO2017069575A1 (ko) | 리간드 화합물, 올레핀 올리고머화용 촉매계, 및 이를 이용한 올레핀 올리고머화 방법 | |
JP6453458B2 (ja) | リガンド化合物、オレフィンオリゴマー化用触媒系、およびこれを用いたオレフィンオリゴマー化方法 | |
WO2015072799A1 (ko) | 리간드 화합물, 올레핀 올리고머화용 촉매계, 및 이를 이용한 올레핀 올리고머화 방법 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
ENP | Entry into the national phase |
Ref document number: 2017522356 Country of ref document: JP Kind code of ref document: A |
|
WWE | Wipo information: entry into national phase |
Ref document number: 15527898 Country of ref document: US |
|
REEP | Request for entry into the european phase |
Ref document number: 2016857832 Country of ref document: EP |
|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 16857832 Country of ref document: EP Kind code of ref document: A1 |
|
NENP | Non-entry into the national phase |
Ref country code: DE |