KR20110064618A - 프로필렌 중합용 고체촉매의 제조 방법 - Google Patents
프로필렌 중합용 고체촉매의 제조 방법 Download PDFInfo
- Publication number
- KR20110064618A KR20110064618A KR1020090121300A KR20090121300A KR20110064618A KR 20110064618 A KR20110064618 A KR 20110064618A KR 1020090121300 A KR1020090121300 A KR 1020090121300A KR 20090121300 A KR20090121300 A KR 20090121300A KR 20110064618 A KR20110064618 A KR 20110064618A
- Authority
- KR
- South Korea
- Prior art keywords
- diethyl
- succinate
- isobutyl
- cyclohexyl
- cyclopentyl
- Prior art date
Links
- 239000011949 solid catalyst Substances 0.000 title claims abstract description 48
- 238000006116 polymerization reaction Methods 0.000 title claims abstract description 34
- 238000000034 method Methods 0.000 title claims abstract description 21
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 title claims abstract description 21
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 title claims abstract description 21
- 238000002360 preparation method Methods 0.000 title description 11
- -1 polypropylene Polymers 0.000 claims abstract description 37
- 229910052719 titanium Inorganic materials 0.000 claims abstract description 27
- 239000010936 titanium Substances 0.000 claims abstract description 26
- 239000003960 organic solvent Substances 0.000 claims abstract description 7
- 238000005406 washing Methods 0.000 claims abstract description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims description 29
- 239000003054 catalyst Substances 0.000 claims description 21
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 16
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 13
- 239000011777 magnesium Substances 0.000 claims description 13
- 229910052749 magnesium Inorganic materials 0.000 claims description 13
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 12
- WGFNXLQURMLAGC-UHFFFAOYSA-N diethyl 2,3-di(propan-2-yl)butanedioate Chemical compound CCOC(=O)C(C(C)C)C(C(C)C)C(=O)OCC WGFNXLQURMLAGC-UHFFFAOYSA-N 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- PYLCKGIPVKXNPB-UHFFFAOYSA-N 2-(1-cyclopentylbutyl)-2-ethyl-1,3-dioxepane-4,7-dione Chemical compound C1(CCC(=O)OC(C(CCC)C2CCCC2)(CC)O1)=O PYLCKGIPVKXNPB-UHFFFAOYSA-N 0.000 claims description 2
- BFCSERSZHHRPJN-UHFFFAOYSA-N 2-(5-ethyl-2-methylheptan-4-yl)-1,3-dioxepane-4,7-dione Chemical compound C1(CCC(=O)OC(C(C(CC)CC)CC(C)C)O1)=O BFCSERSZHHRPJN-UHFFFAOYSA-N 0.000 claims description 2
- ZTCPMFIUHHDXRX-UHFFFAOYSA-N C1(CCC(=O)OC(C(C(CC)CC)C(C)C)O1)=O Chemical compound C1(CCC(=O)OC(C(C(CC)CC)C(C)C)O1)=O ZTCPMFIUHHDXRX-UHFFFAOYSA-N 0.000 claims description 2
- QJUSVMHJWMZLTB-UHFFFAOYSA-N C1(CCC(=O)OC(C(CCC)C2CCCCC2)(CC)O1)=O Chemical compound C1(CCC(=O)OC(C(CCC)C2CCCCC2)(CC)O1)=O QJUSVMHJWMZLTB-UHFFFAOYSA-N 0.000 claims description 2
- AVLHXEDOBYYTGV-UHFFFAOYSA-N diethyl 2,3-bis(2-methylpropyl)butanedioate Chemical compound CCOC(=O)C(CC(C)C)C(CC(C)C)C(=O)OCC AVLHXEDOBYYTGV-UHFFFAOYSA-N 0.000 claims description 2
- RPFNAJGCHRWCRI-UHFFFAOYSA-N diethyl 2,3-dibutylbutanedioate Chemical compound CCCCC(C(=O)OCC)C(CCCC)C(=O)OCC RPFNAJGCHRWCRI-UHFFFAOYSA-N 0.000 claims description 2
- CXKANZAMPQTLBJ-UHFFFAOYSA-N diethyl 2,3-dicyclohexylbutanedioate Chemical compound C1CCCCC1C(C(=O)OCC)C(C(=O)OCC)C1CCCCC1 CXKANZAMPQTLBJ-UHFFFAOYSA-N 0.000 claims description 2
- ISOWAXIPBFLPIC-UHFFFAOYSA-N diethyl 2,3-dicyclopentylbutanedioate Chemical compound C1CCCC1C(C(=O)OCC)C(C(=O)OCC)C1CCCC1 ISOWAXIPBFLPIC-UHFFFAOYSA-N 0.000 claims description 2
- PYQDOTSNFYFMQJ-UHFFFAOYSA-N diethyl 2,3-diethylbutanedioate Chemical compound CCOC(=O)C(CC)C(CC)C(=O)OCC PYQDOTSNFYFMQJ-UHFFFAOYSA-N 0.000 claims description 2
- ARGBPZNWFLEUFR-UHFFFAOYSA-N diethyl 2,3-dihexylbutanedioate Chemical compound CCCCCCC(C(=O)OCC)C(C(=O)OCC)CCCCCC ARGBPZNWFLEUFR-UHFFFAOYSA-N 0.000 claims description 2
- PBCHBEKHOCTNCV-UHFFFAOYSA-N diethyl 2,3-dimethylbutanedioate Chemical group CCOC(=O)C(C)C(C)C(=O)OCC PBCHBEKHOCTNCV-UHFFFAOYSA-N 0.000 claims description 2
- AMVKWGGQIXFLEH-UHFFFAOYSA-N diethyl 2,3-dipentylbutanedioate Chemical compound CCCCCC(C(=O)OCC)C(C(=O)OCC)CCCCC AMVKWGGQIXFLEH-UHFFFAOYSA-N 0.000 claims description 2
- WWIDLUJSQINFMG-UHFFFAOYSA-N diethyl 2,3-dipropylbutanedioate Chemical compound CCOC(=O)C(CCC)C(CCC)C(=O)OCC WWIDLUJSQINFMG-UHFFFAOYSA-N 0.000 claims description 2
- YTOVXAZHYWWROF-UHFFFAOYSA-N diethyl 2-cyclohexyl-3-ethylbutanedioate Chemical compound CCOC(=O)C(CC)C(C(=O)OCC)C1CCCCC1 YTOVXAZHYWWROF-UHFFFAOYSA-N 0.000 claims description 2
- POGMUHAVUHTISW-UHFFFAOYSA-N diethyl 2-cyclohexylidene-3-ethylbutanedioate Chemical compound CCOC(=O)C(CC)C(C(=O)OCC)=C1CCCCC1 POGMUHAVUHTISW-UHFFFAOYSA-N 0.000 claims description 2
- WLBLMACKKAHWTD-UHFFFAOYSA-N diethyl 2-cyclohexylidene-3-propan-2-ylbutanedioate Chemical compound CCOC(=O)C(C(C)C)C(C(=O)OCC)=C1CCCCC1 WLBLMACKKAHWTD-UHFFFAOYSA-N 0.000 claims description 2
- XLTOJQMIDBPERP-UHFFFAOYSA-N diethyl 2-cyclohexylidene-3-propylbutanedioate Chemical compound CCOC(=O)C(CCC)C(C(=O)OCC)=C1CCCCC1 XLTOJQMIDBPERP-UHFFFAOYSA-N 0.000 claims description 2
- PXFGYMQCKMAFLT-UHFFFAOYSA-N diethyl 2-cyclopentyl-3-ethylbutanedioate Chemical compound CCOC(=O)C(CC)C(C(=O)OCC)C1CCCC1 PXFGYMQCKMAFLT-UHFFFAOYSA-N 0.000 claims description 2
- ZSIRCOMUCBYNOP-UHFFFAOYSA-N diethyl 2-cyclopentyl-3-methylbutanedioate Chemical compound CCOC(=O)C(C)C(C(=O)OCC)C1CCCC1 ZSIRCOMUCBYNOP-UHFFFAOYSA-N 0.000 claims description 2
- NHNLWBQLANICTP-UHFFFAOYSA-N diethyl 2-cyclopentylidene-3-ethylbutanedioate Chemical compound CCOC(=O)C(CC)C(C(=O)OCC)=C1CCCC1 NHNLWBQLANICTP-UHFFFAOYSA-N 0.000 claims description 2
- LNIBBZAHTXVVCS-UHFFFAOYSA-N diethyl 2-cyclopentylidene-3-methylbutanedioate Chemical compound CCOC(=O)C(C)C(C(=O)OCC)=C1CCCC1 LNIBBZAHTXVVCS-UHFFFAOYSA-N 0.000 claims description 2
- QAYIFXMNFQCDCK-UHFFFAOYSA-N diethyl 2-cyclopentylidene-3-propan-2-ylbutanedioate Chemical compound CCOC(=O)C(C(C)C)C(C(=O)OCC)=C1CCCC1 QAYIFXMNFQCDCK-UHFFFAOYSA-N 0.000 claims description 2
- CSOMFVQRCADLDC-UHFFFAOYSA-N diethyl 2-cyclopentylidene-3-propylbutanedioate Chemical compound CCOC(=O)C(CCC)C(C(=O)OCC)=C1CCCC1 CSOMFVQRCADLDC-UHFFFAOYSA-N 0.000 claims description 2
- YILPHPRNRKWAAE-UHFFFAOYSA-N diethyl 2-ethyl-3-(2-methylpropyl)butanedioate Chemical compound CCOC(=O)C(CC)C(CC(C)C)C(=O)OCC YILPHPRNRKWAAE-UHFFFAOYSA-N 0.000 claims description 2
- APNRFJFSDBBDLK-UHFFFAOYSA-N diethyl 2-ethyl-3-(2-methylpropylidene)butanedioate Chemical compound CCOC(=O)C(CC)C(=CC(C)C)C(=O)OCC APNRFJFSDBBDLK-UHFFFAOYSA-N 0.000 claims description 2
- JHKBCCAFSWQGRQ-UHFFFAOYSA-N diethyl 2-ethyl-3-propan-2-ylbutanedioate Chemical compound CCOC(=O)C(CC)C(C(C)C)C(=O)OCC JHKBCCAFSWQGRQ-UHFFFAOYSA-N 0.000 claims description 2
- HHMDXJWUTGKDQY-UHFFFAOYSA-N diethyl 2-ethyl-3-propan-2-ylidenebutanedioate Chemical compound CCOC(=O)C(CC)C(=C(C)C)C(=O)OCC HHMDXJWUTGKDQY-UHFFFAOYSA-N 0.000 claims description 2
- SDHHCQNJAFPQJX-UHFFFAOYSA-N diethyl 2-methyl-3-(2-methylpropylidene)butanedioate Chemical compound CCOC(=O)C(C)C(=CC(C)C)C(=O)OCC SDHHCQNJAFPQJX-UHFFFAOYSA-N 0.000 claims description 2
- YFQCVHDCRKIAOE-UHFFFAOYSA-N diethyl 2-methyl-3-propan-2-ylidenebutanedioate Chemical compound CCOC(=O)C(C)C(=C(C)C)C(=O)OCC YFQCVHDCRKIAOE-UHFFFAOYSA-N 0.000 claims description 2
- KCTDBKWBERFBGM-UHFFFAOYSA-N diethyl 2-propan-2-ylidene-3-propylbutanedioate Chemical compound CCOC(=O)C(CCC)C(=C(C)C)C(=O)OCC KCTDBKWBERFBGM-UHFFFAOYSA-N 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- KOIAEEBEROMPKL-UHFFFAOYSA-N 1,3-dioxepane-4,7-dione Chemical compound O=C1CCC(=O)OCO1 KOIAEEBEROMPKL-UHFFFAOYSA-N 0.000 claims 1
- 229910002651 NO3 Inorganic materials 0.000 claims 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims 1
- NWHNQIAHCWWKOX-UHFFFAOYSA-N diethyl 2,3-di(cyclohexylidene)butanedioate Chemical compound C1CCCCC1=C(C(=O)OCC)C(C(=O)OCC)=C1CCCCC1 NWHNQIAHCWWKOX-UHFFFAOYSA-N 0.000 claims 1
- POPLRBNEOWUZNL-UHFFFAOYSA-N diethyl 2-(2-methylpropyl)-3-propylbutanedioate Chemical compound CCOC(=O)C(CCC)C(CC(C)C)C(=O)OCC POPLRBNEOWUZNL-UHFFFAOYSA-N 0.000 claims 1
- OKPPYOBHSXQIJJ-UHFFFAOYSA-N diethyl 2-cyclohexyl-3-(2-methylpropyl)butanedioate Chemical compound CCOC(=O)C(CC(C)C)C(C(=O)OCC)C1CCCCC1 OKPPYOBHSXQIJJ-UHFFFAOYSA-N 0.000 claims 1
- MYRINXCERJBIKE-UHFFFAOYSA-N diethyl 2-cyclohexylidene-3-(2-methylpropyl)butanedioate Chemical compound CCOC(=O)C(CC(C)C)C(C(=O)OCC)=C1CCCCC1 MYRINXCERJBIKE-UHFFFAOYSA-N 0.000 claims 1
- HYSVJHWQBIQEFR-UHFFFAOYSA-N diethyl 2-cyclohexylidene-3-methylbutanedioate Chemical compound CCOC(=O)C(C)C(C(=O)OCC)=C1CCCCC1 HYSVJHWQBIQEFR-UHFFFAOYSA-N 0.000 claims 1
- XRGMCNXSRPONPP-UHFFFAOYSA-N diethyl 2-cyclopentyl-3-propan-2-ylbutanedioate Chemical compound CCOC(=O)C(C(C)C)C(C(=O)OCC)C1CCCC1 XRGMCNXSRPONPP-UHFFFAOYSA-N 0.000 claims 1
- LHULZUARHMSEAL-UHFFFAOYSA-N diethyl 2-cyclopentyl-3-propylbutanedioate Chemical compound CCOC(=O)C(CCC)C(C(=O)OCC)C1CCCC1 LHULZUARHMSEAL-UHFFFAOYSA-N 0.000 claims 1
- GLICVMZCNWSOGS-UHFFFAOYSA-N diethyl 2-cyclopentylidene-3-(2-methylpropyl)butanedioate Chemical compound CCOC(=O)C(CC(C)C)C(C(=O)OCC)=C1CCCC1 GLICVMZCNWSOGS-UHFFFAOYSA-N 0.000 claims 1
- ILLRNSFRMUOCHV-UHFFFAOYSA-N diethyl 2-propan-2-yl-3-propylbutanedioate Chemical compound CCOC(=O)C(CCC)C(C(C)C)C(=O)OCC ILLRNSFRMUOCHV-UHFFFAOYSA-N 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 238000009826 distribution Methods 0.000 abstract description 16
- 239000004743 Polypropylene Substances 0.000 abstract description 15
- 229920001155 polypropylene Polymers 0.000 abstract description 14
- 239000000126 substance Substances 0.000 abstract description 3
- 230000000379 polymerizing effect Effects 0.000 abstract description 2
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
- 229920000642 polymer Polymers 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
- 239000002245 particle Substances 0.000 description 7
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 6
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 5
- 230000003197 catalytic effect Effects 0.000 description 5
- 238000007334 copolymerization reaction Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000002002 slurry Substances 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- 229910001629 magnesium chloride Inorganic materials 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 230000037048 polymerization activity Effects 0.000 description 3
- 239000006228 supernatant Substances 0.000 description 3
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 3
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- 230000032683 aging Effects 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- ZEZXMFBCRYGNNP-UHFFFAOYSA-N butyl(diethoxy)silane Chemical compound CCCC[SiH](OCC)OCC ZEZXMFBCRYGNNP-UHFFFAOYSA-N 0.000 description 2
- XGZGKDQVCBHSGI-UHFFFAOYSA-N butyl(triethoxy)silane Chemical compound CCCC[Si](OCC)(OCC)OCC XGZGKDQVCBHSGI-UHFFFAOYSA-N 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- JWCYDYZLEAQGJJ-UHFFFAOYSA-N dicyclopentyl(dimethoxy)silane Chemical compound C1CCCC1[Si](OC)(OC)C1CCCC1 JWCYDYZLEAQGJJ-UHFFFAOYSA-N 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- MGWAVDBGNNKXQV-UHFFFAOYSA-N diisobutyl phthalate Chemical compound CC(C)COC(=O)C1=CC=CC=C1C(=O)OCC(C)C MGWAVDBGNNKXQV-UHFFFAOYSA-N 0.000 description 2
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- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 1
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- RKAFKUROUOLPOL-UHFFFAOYSA-N 2-propan-2-ylbutanedioic acid Chemical compound CC(C)C(C(O)=O)CC(O)=O RKAFKUROUOLPOL-UHFFFAOYSA-N 0.000 description 1
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- 230000004913 activation Effects 0.000 description 1
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- 150000007824 aliphatic compounds Chemical class 0.000 description 1
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- 230000008025 crystallization Effects 0.000 description 1
- DTWBSVFCEPCAOL-UHFFFAOYSA-N cycloheptyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C1CCCCCC1 DTWBSVFCEPCAOL-UHFFFAOYSA-N 0.000 description 1
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- UOQJOHZBTJKWBG-UHFFFAOYSA-N cycloheptyl-diethoxy-ethylsilane Chemical compound CCO[Si](CC)(OCC)C1CCCCCC1 UOQJOHZBTJKWBG-UHFFFAOYSA-N 0.000 description 1
- KKZDIILZUJLDKA-UHFFFAOYSA-N cycloheptyl-diethoxy-methylsilane Chemical compound CCO[Si](C)(OCC)C1CCCCCC1 KKZDIILZUJLDKA-UHFFFAOYSA-N 0.000 description 1
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- MEWFSXFFGFDHGV-UHFFFAOYSA-N cyclohexyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C1CCCCC1 MEWFSXFFGFDHGV-UHFFFAOYSA-N 0.000 description 1
- SFEWPQUOONCGJP-UHFFFAOYSA-N cyclohexyl-diethoxy-ethylsilane Chemical compound CCO[Si](CC)(OCC)C1CCCCC1 SFEWPQUOONCGJP-UHFFFAOYSA-N 0.000 description 1
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- 230000006866 deterioration Effects 0.000 description 1
- XVYDOHRNOUNBJI-UHFFFAOYSA-N di(cycloheptyl)-diethoxysilane Chemical compound C1CCCCCC1[Si](OCC)(OCC)C1CCCCCC1 XVYDOHRNOUNBJI-UHFFFAOYSA-N 0.000 description 1
- JPVSOBGZRHNVHP-UHFFFAOYSA-N di(cycloheptyl)-dimethoxysilane Chemical compound C1CCCCCC1[Si](OC)(OC)C1CCCCCC1 JPVSOBGZRHNVHP-UHFFFAOYSA-N 0.000 description 1
- CGYGEZLIGMBRKL-UHFFFAOYSA-N dicyclohexyl(diethoxy)silane Chemical compound C1CCCCC1[Si](OCC)(OCC)C1CCCCC1 CGYGEZLIGMBRKL-UHFFFAOYSA-N 0.000 description 1
- ZVMRWPHIZSSUKP-UHFFFAOYSA-N dicyclohexyl(dimethoxy)silane Chemical compound C1CCCCC1[Si](OC)(OC)C1CCCCC1 ZVMRWPHIZSSUKP-UHFFFAOYSA-N 0.000 description 1
- FVAXOELGJXMINU-UHFFFAOYSA-N dicyclopentyl(diethoxy)silane Chemical compound C1CCCC1[Si](OCC)(OCC)C1CCCC1 FVAXOELGJXMINU-UHFFFAOYSA-N 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000000378 dietary effect Effects 0.000 description 1
- PRODGEYRKLMWHE-UHFFFAOYSA-N diethoxy(2-phenylethyl)silane Chemical compound CCO[SiH](OCC)CCC1=CC=CC=C1 PRODGEYRKLMWHE-UHFFFAOYSA-N 0.000 description 1
- ZZNQQQWFKKTOSD-UHFFFAOYSA-N diethoxy(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](OCC)(OCC)C1=CC=CC=C1 ZZNQQQWFKKTOSD-UHFFFAOYSA-N 0.000 description 1
- DVAZURRZYNXADH-UHFFFAOYSA-N diethoxy(pentyl)silane Chemical compound CCCCC[SiH](OCC)OCC DVAZURRZYNXADH-UHFFFAOYSA-N 0.000 description 1
- FZQNBVBLHJXOEA-UHFFFAOYSA-N diethoxy(propyl)silane Chemical compound CCC[SiH](OCC)OCC FZQNBVBLHJXOEA-UHFFFAOYSA-N 0.000 description 1
- WOZOEHNJNZTJDH-UHFFFAOYSA-N diethoxy-bis(2-methylpropyl)silane Chemical compound CCO[Si](CC(C)C)(CC(C)C)OCC WOZOEHNJNZTJDH-UHFFFAOYSA-N 0.000 description 1
- VVKJJEAEVBNODX-UHFFFAOYSA-N diethoxy-di(propan-2-yl)silane Chemical compound CCO[Si](C(C)C)(C(C)C)OCC VVKJJEAEVBNODX-UHFFFAOYSA-N 0.000 description 1
- MNFGEHQPOWJJBH-UHFFFAOYSA-N diethoxy-methyl-phenylsilane Chemical compound CCO[Si](C)(OCC)C1=CC=CC=C1 MNFGEHQPOWJJBH-UHFFFAOYSA-N 0.000 description 1
- PFAAOIPGMUCNMN-UHFFFAOYSA-N diethyl 2-(2-methylpropylidene)-3-propylbutanedioate Chemical compound CCOC(=O)C(CCC)C(=CC(C)C)C(=O)OCC PFAAOIPGMUCNMN-UHFFFAOYSA-N 0.000 description 1
- FIAGTMBLOZDSSD-UHFFFAOYSA-N diethyl 2-cyclohexyl-3-methylbutanedioate Chemical compound CCOC(=O)C(C)C(C(=O)OCC)C1CCCCC1 FIAGTMBLOZDSSD-UHFFFAOYSA-N 0.000 description 1
- MYRFWIPQLLEEQZ-UHFFFAOYSA-N diethyl 2-methyl-3-(2-methylpropyl)butanedioate Chemical compound CCOC(=O)C(C)C(CC(C)C)C(=O)OCC MYRFWIPQLLEEQZ-UHFFFAOYSA-N 0.000 description 1
- WJSDXQNXRANRTM-UHFFFAOYSA-N diethyl 2-methyl-3-propan-2-ylbutanedioate Chemical compound CCOC(=O)C(C)C(C(C)C)C(=O)OCC WJSDXQNXRANRTM-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- AHUXYBVKTIBBJW-UHFFFAOYSA-N dimethoxy(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](OC)(OC)C1=CC=CC=C1 AHUXYBVKTIBBJW-UHFFFAOYSA-N 0.000 description 1
- SGKDAFJDYSMACD-UHFFFAOYSA-N dimethoxy(propyl)silane Chemical compound CCC[SiH](OC)OC SGKDAFJDYSMACD-UHFFFAOYSA-N 0.000 description 1
- NHYFIJRXGOQNFS-UHFFFAOYSA-N dimethoxy-bis(2-methylpropyl)silane Chemical compound CC(C)C[Si](OC)(CC(C)C)OC NHYFIJRXGOQNFS-UHFFFAOYSA-N 0.000 description 1
- VHPUZTHRFWIGAW-UHFFFAOYSA-N dimethoxy-di(propan-2-yl)silane Chemical compound CO[Si](OC)(C(C)C)C(C)C VHPUZTHRFWIGAW-UHFFFAOYSA-N 0.000 description 1
- CVQVSVBUMVSJES-UHFFFAOYSA-N dimethoxy-methyl-phenylsilane Chemical compound CO[Si](C)(OC)C1=CC=CC=C1 CVQVSVBUMVSJES-UHFFFAOYSA-N 0.000 description 1
- JWYGLBSNXMQPFL-UHFFFAOYSA-N dimethoxy-phenyl-propylsilane Chemical compound CCC[Si](OC)(OC)C1=CC=CC=C1 JWYGLBSNXMQPFL-UHFFFAOYSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- XDKQUSKHRIUJEO-UHFFFAOYSA-N magnesium;ethanolate Chemical compound [Mg+2].CC[O-].CC[O-] XDKQUSKHRIUJEO-UHFFFAOYSA-N 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 150000003961 organosilicon compounds Chemical class 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- SQBBHCOIQXKPHL-UHFFFAOYSA-N tributylalumane Chemical compound CCCC[Al](CCCC)CCCC SQBBHCOIQXKPHL-UHFFFAOYSA-N 0.000 description 1
- ALVYUZIFSCKIFP-UHFFFAOYSA-N triethoxy(2-methylpropyl)silane Chemical compound CCO[Si](CC(C)C)(OCC)OCC ALVYUZIFSCKIFP-UHFFFAOYSA-N 0.000 description 1
- FHVAUDREWWXPRW-UHFFFAOYSA-N triethoxy(pentyl)silane Chemical compound CCCCC[Si](OCC)(OCC)OCC FHVAUDREWWXPRW-UHFFFAOYSA-N 0.000 description 1
- JCVQKRGIASEUKR-UHFFFAOYSA-N triethoxy(phenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC=C1 JCVQKRGIASEUKR-UHFFFAOYSA-N 0.000 description 1
- BJDLPDPRMYAOCM-UHFFFAOYSA-N triethoxy(propan-2-yl)silane Chemical compound CCO[Si](OCC)(OCC)C(C)C BJDLPDPRMYAOCM-UHFFFAOYSA-N 0.000 description 1
- NBXZNTLFQLUFES-UHFFFAOYSA-N triethoxy(propyl)silane Chemical compound CCC[Si](OCC)(OCC)OCC NBXZNTLFQLUFES-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
- XYJRNCYWTVGEEG-UHFFFAOYSA-N trimethoxy(2-methylpropyl)silane Chemical compound CO[Si](OC)(OC)CC(C)C XYJRNCYWTVGEEG-UHFFFAOYSA-N 0.000 description 1
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 1
- LGROXJWYRXANBB-UHFFFAOYSA-N trimethoxy(propan-2-yl)silane Chemical compound CO[Si](OC)(OC)C(C)C LGROXJWYRXANBB-UHFFFAOYSA-N 0.000 description 1
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- LFXVBWRMVZPLFK-UHFFFAOYSA-N trioctylalumane Chemical compound CCCCCCCC[Al](CCCCCCCC)CCCCCCCC LFXVBWRMVZPLFK-UHFFFAOYSA-N 0.000 description 1
- CNWZYDSEVLFSMS-UHFFFAOYSA-N tripropylalumane Chemical compound CCC[Al](CCC)CCC CNWZYDSEVLFSMS-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C08F4/64—Titanium, zirconium, hafnium or compounds thereof
- C08F4/65—Pretreating the metal or compound covered by group C08F4/64 before the final contacting with the metal or compound covered by group C08F4/44
- C08F4/652—Pretreating with metals or metal-containing compounds
- C08F4/654—Pretreating with metals or metal-containing compounds with magnesium or compounds thereof
-
- 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
- C08F110/00—Homopolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F110/04—Monomers containing three or four carbon atoms
- C08F110/06—Propene
-
- 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
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
-
- 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
- C08F10/04—Monomers containing three or four carbon atoms
- C08F10/06—Propene
-
- 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
- C08F4/28—Oxygen or compounds releasing free oxygen
- C08F4/32—Organic compounds
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Abstract
Description
예 | 활성 (kg-PP/g-Cat) |
입체규칙성 (X.I., wt.%) |
용융흐름지수 (MFR, g/10 min) |
분자량 분포 (P.I.) |
실시예 1 | 42.0 | 98.0 | 2.2 | 7.0 |
실시예 2 | 44.8 | 98.5 | 1.9 | 6.9 |
실시예 3 | 45.9 | 98.6 | 1.7 | 6.8 |
실시예 4 | 40.8 | 97.8 | 3.0 | 7.5 |
비교예 1 | 26.0 | 97.3 | 5.6 | 4.8 |
비교예 2 | 45.5 | 98.5 | 0.8 | 6.3 |
비교예 3 | 22.7 | 97.8 | 2.5 | 5.0 |
Claims (4)
- 다음의 단계들을 포함하는 것을 특징으로 하는 프로필렌 중합용 고체촉매의 제조 방법:(1) 유기용매의 존재 하에서 디알콕시마그네슘과 티타늄할라이드를 반응시키는 단계;(2) 80~130℃의 온도로 승온시키면서, 상기 단계 (1)의 결과물에 하기 일반식(Ⅱ)로부터 선택되는 내부전자공여체와 함께 일반식(III) 또는 일반식(Ⅳ)로부터 선택되는 내부전자공여체를 혼합투입하여 반응시키는 단계,(여기에서, R1, R2, R3 및 R4는 독립적으로 탄소원자 1~10개의 선형, 가지형 또는 고리형 알킬기 또는 수소원자이다)(여기에서, R1 및 R2는 독립적으로 탄소원자 1~10개의 선형, 가지형 또는 고 리형 알킬기 또는 수소원자이고, R3 및 R4는 독립적으로 탄소원자 1~10개의 선형, 가지형 또는 고리형 알킬기이다)(여기에서, R1, R2 및 R4는 독립적으로 탄소원자 1~10개의 선형, 가지형 또는 고리형 알킬기 또는 수소원자이고, R3은 탄소원자 1~10개의 선형, 가지형 또는 고리형 알킬기이다); 및(3) 80~130℃의 온도에서 상기 단계 (2)의 결과물과 티타늄할라이드를 반응시키고, 결과물을 세척하는 단계.
- 제1항에 있어서, 상기 고체촉매는 마그네슘 5~40중량%, 티타늄 0.5~10중량%, 할로겐 50~85중량% 및 내부전자공여체 2.5~30중량%를 포함하는 것을 특징으로 하는 프로필렌 중합용 고체촉매의 제조 방법.
- 제1항에 있어서, 상기 내부전자공여체는 디에틸-2,3-디메틸숙시네이트, 디에틸-2,3-디에틸숙시네이트, 디에틸-2,3-디프로필숙시네이트, 디에틸-2,3-디이소프로필숙시네이트, 디에틸-2,3-디부틸숙시네이트, 디에틸-2,3-디이소부틸숙시네이트, 디에틸-2,3-디펜틸숙시네이트, 디에틸-2,3-디헥실숙시네이트, 디에틸-2,3-디시클로펜틸숙시네이트, 디에틸-2,3-디시클로헥실숙시네이트, 디에틸-2-시클로펜틸-3-메틸숙시네이트, 디에틸-2-시클로헥실-3-메틸숙시네이트, 디에틸-2-이소프로필-3-메틸숙시네이트, 디에틸-2-이소부틸-3-메틸숙시네이트, 디에틸-2-시클로펜틸-3-에틸숙시네이트, 디에틸-2-시클로헥실-3-에틸숙시네이트, 디에틸-2-이소프로필-3-에틸숙시네이트, 디에틸-2-이소부틸-3-에틸숙시네이트, 디에틸-2-시클로펜틸-3-프로필숙시네이트, 디에틸-2-시클로헥실-3-프로필숙시네이트, 디에틸-2-이소프로필-3-프로필숙시네이트, 디에틸-2-이소부틸-3-프로필숙시네이트, 디에틸-2-시클로펜틸-3-이소프로필숙시네이트, 디에틸-2-시클로헥실-3-이소프로필숙시네이트, 디에틸-2-이소부틸-3-이소프로필숙시네이트, 디에틸-2-시클로펜틸-3-이소부틸숙시네이트, 디에틸-2-시클로헥실-3-이소부틸숙시네이트, 디에틸-2-이소프로필-3-이소부틸필숙시네이트, 디에틸-2,3-디메틸리덴숙시네이트, 디에틸-2,3-디에틸리덴숙시네이트, 디에틸-2,3-디프로필리덴숙시네이트, 디에틸-2,3-디이소프로필리덴숙시네이트, 디에틸-2,3-디부틸리덴숙시네이트, 디에틸-2,3-디이소부틸리덴숙시네이트, 디에틸-2,3-디펜틸리덴숙시네이트, 디에틸-2,3-디헥실리덴숙시네이트, 디에틸-2,3-디시클로펜틸리덴숙시네이트, 디에틸-2,3-디시클로헥실리덴숙시네이트, 디에틸-2-시클로펜틸-3-메틸리덴숙시네이트, 디에틸-2-시클로헥실-3-메틸리덴숙시네이트, 디에틸-2-이소프로필-3-메틸리덴숙시네이트, 디에틸-2-이소부틸-3-메틸리덴숙시네이트, 디에틸-2-시클로펜틸-3-에틸리덴숙시네이트, 디에틸-2-시클로헥실-3-에틸리덴숙시네이트, 디에틸-2-이소프로필-3-에틸리덴숙시네이트, 디에틸-2-이소부틸-3-에틸리덴숙시네이 트, 디에틸-2-시클로펜틸-3-프로필리덴숙시네이트, 디에틸-2-시클로헥실-3-프로필리덴숙시네이트, 디에틸-2-이소프로필-3-프로필리덴숙시네이트, 디에틸-2-이소부틸-3-프로필리덴숙시네이트, 디에틸-2-시클로펜틸-3-이소프로필리덴숙시네이트, 디에틸-2-시클로헥실-3-이소프로필리덴숙시네이트, 디에틸-2-이소부틸-3-이소프로필리덴숙시네이트, 디에틸-2-시클로펜틸-3-이소부틸리덴숙시네이트, 디에틸-2-시클로헥실-3-이소부틸리덴숙시네이트, 디에틸-2-이소프로필-3-이소부틸리덴필숙시네이트, 디에틸-2-시클로펜틸리덴-3-메틸숙시네이트, 디에틸-2-시클로헥실리덴-3-메틸숙시네이트, 디에틸-2-이소프로필리덴-3-메틸숙시네이트, 디에틸-2-이소부틸리덴-3-메틸숙시네이트, 디에틸-2-시클로펜틸리덴-3-에틸숙시네이트, 디에틸-2-시클로헥실리덴-3-에틸숙시네이트, 디에틸-2-이소프로필리덴-3-에틸숙시네이트, 디에틸-2-이소부틸리덴-3-에틸숙시네이트, 디에틸-2-시클로펜틸리덴-3-프로필숙시네이트, 디에틸-2-시클로헥실리덴-3-프로필숙시네이트, 디에틸-2-이소프로필리덴-3-프로필숙시네이트, 디에틸-2-이소부틸리덴-3-프로필숙시네이트, 디에틸-2-시클로펜틸리덴-3-이소프로필숙시네이트, 디에틸-2-시클로헥실리덴-3-이소프로필숙시네이트, 디에틸-2-이소부틸리덴-3-이소프로필숙시네이트, 디에틸-2-시클로펜틸리덴-3-이소부틸숙시네이트, 디에틸-2-시클로헥실리덴-3-이소부틸숙시네이트, 및 디에틸-2-이소프로필리덴-3-이소부틸필숙시네이트 중에서 선택되는 것을 특징으로 하는 프로필렌 중합용 고체촉매의 제조방법.
- 제 1항 내지 제 3항 중 어느 한 항에 있어서, 상기 디알콕시마그네슘 1몰에 대하여 상기 내부전자공여체 0.1~1.0몰을 사용하는 것을 특징으로 하는 프로필렌 중합용 고체촉매 제조방법.
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