ES2297014T3 - Componentes y catalizadores para la polimerizacion de olefinas. - Google Patents
Componentes y catalizadores para la polimerizacion de olefinas. Download PDFInfo
- Publication number
- ES2297014T3 ES2297014T3 ES02779321T ES02779321T ES2297014T3 ES 2297014 T3 ES2297014 T3 ES 2297014T3 ES 02779321 T ES02779321 T ES 02779321T ES 02779321 T ES02779321 T ES 02779321T ES 2297014 T3 ES2297014 T3 ES 2297014T3
- Authority
- ES
- Spain
- Prior art keywords
- group
- polymerization
- alkyl
- olefins
- solid catalyst
- 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.)
- Expired - Lifetime
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- 239000003054 catalyst Substances 0.000 title claims abstract description 39
- 238000006116 polymerization reaction Methods 0.000 title claims abstract description 30
- 150000001336 alkenes Chemical class 0.000 title claims abstract description 14
- 239000011949 solid catalyst Substances 0.000 claims abstract description 19
- 150000002688 maleic acid derivatives Chemical class 0.000 claims abstract description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 13
- 239000001257 hydrogen Substances 0.000 claims abstract description 13
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 12
- 229910052749 magnesium Inorganic materials 0.000 claims abstract description 11
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 10
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 9
- 229910052719 titanium Inorganic materials 0.000 claims abstract description 9
- 150000002367 halogens Chemical class 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 22
- -1 alkylaluminum compound Chemical class 0.000 claims description 21
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 14
- 239000010936 titanium Substances 0.000 claims description 13
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000005842 heteroatom Chemical group 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 150000003377 silicon compounds Chemical class 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 150000003609 titanium compounds Chemical class 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 4
- JWCYDYZLEAQGJJ-UHFFFAOYSA-N dicyclopentyl(dimethoxy)silane Chemical compound C1CCCC1[Si](OC)(OC)C1CCCC1 JWCYDYZLEAQGJJ-UHFFFAOYSA-N 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
- PJSFQEVODHCOOF-UHFFFAOYSA-N (2-ethylpiperidin-1-yl)-dimethoxy-(3,3,3-trifluoropropyl)silane Chemical compound CCC1CCCCN1[Si](CCC(F)(F)F)(OC)OC PJSFQEVODHCOOF-UHFFFAOYSA-N 0.000 claims description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- MEWFSXFFGFDHGV-UHFFFAOYSA-N cyclohexyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C1CCCCC1 MEWFSXFFGFDHGV-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- HXLWJGIPGJFBEZ-UHFFFAOYSA-N tert-butyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C(C)(C)C HXLWJGIPGJFBEZ-UHFFFAOYSA-N 0.000 claims description 2
- NETBVGNWMHLXRP-UHFFFAOYSA-N tert-butyl-dimethoxy-methylsilane Chemical compound CO[Si](C)(OC)C(C)(C)C NETBVGNWMHLXRP-UHFFFAOYSA-N 0.000 claims description 2
- SQBBHCOIQXKPHL-UHFFFAOYSA-N tributylalumane Chemical compound CCCC[Al](CCCC)CCCC SQBBHCOIQXKPHL-UHFFFAOYSA-N 0.000 claims description 2
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 claims description 2
- ORYGRKHDLWYTKX-UHFFFAOYSA-N trihexylalumane Chemical compound CCCCCC[Al](CCCCCC)CCCCCC ORYGRKHDLWYTKX-UHFFFAOYSA-N 0.000 claims description 2
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 claims description 2
- LFXVBWRMVZPLFK-UHFFFAOYSA-N trioctylalumane Chemical compound CCCCCCCC[Al](CCCCCCCC)CCCCCCCC LFXVBWRMVZPLFK-UHFFFAOYSA-N 0.000 claims description 2
- SJJCABYOVIHNPZ-UHFFFAOYSA-N cyclohexyl-dimethoxy-methylsilane Chemical compound CO[Si](C)(OC)C1CCCCC1 SJJCABYOVIHNPZ-UHFFFAOYSA-N 0.000 claims 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract description 11
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 abstract description 9
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 abstract description 9
- 229920000642 polymer Polymers 0.000 abstract description 8
- 239000008096 xylene Substances 0.000 abstract description 7
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 16
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 239000011777 magnesium Substances 0.000 description 11
- 235000005911 diet Nutrition 0.000 description 10
- 230000000378 dietary effect Effects 0.000 description 10
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- 235000011147 magnesium chloride Nutrition 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 238000011282 treatment Methods 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 229910001629 magnesium chloride Inorganic materials 0.000 description 5
- 230000027756 respiratory electron transport chain Effects 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidine Chemical compound CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- IEPRKVQEAMIZSS-UHFFFAOYSA-N Di-Et ester-Fumaric acid Natural products CCOC(=O)C=CC(=O)OCC IEPRKVQEAMIZSS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 229910003074 TiCl4 Inorganic materials 0.000 description 2
- 125000005234 alkyl aluminium group Chemical group 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000012662 bulk polymerization Methods 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- JLWVILKDYQLFEY-NXVVXOECSA-N diethyl (z)-2-decylbut-2-enedioate Chemical compound CCCCCCCCCC\C(C(=O)OCC)=C\C(=O)OCC JLWVILKDYQLFEY-NXVVXOECSA-N 0.000 description 2
- STRNXFOUBFLVIN-UHFFFAOYSA-N diethyl but-2-ynedioate Chemical compound CCOC(=O)C#CC(=O)OCC STRNXFOUBFLVIN-UHFFFAOYSA-N 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical class ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 2
- 229940078552 o-xylene Drugs 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 230000000707 stereoselective effect Effects 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 2
- IWJOJVMZPDMJNU-HJWRWDBZSA-N (Z)-2-ethyl-3-pentylbut-2-enedioic acid Chemical compound C(C)/C(/C(=O)O)=C(/C(=O)O)CCCCC IWJOJVMZPDMJNU-HJWRWDBZSA-N 0.000 description 1
- FTLHGWFLRRMJKB-SREVYHEPSA-N (Z)-2-methyl-3-(2-methylpropyl)but-2-enedioic acid Chemical compound C(C(C)C)/C(/C(=O)O)=C(/C(=O)O)C FTLHGWFLRRMJKB-SREVYHEPSA-N 0.000 description 1
- DHELOSXWRJQHKQ-UPHRSURJSA-N (Z)-4-oxo-4-(3,3,3-trifluoropropoxy)but-2-enoic acid Chemical compound C(COC(=O)/C=C\C(=O)O)C(F)(F)F DHELOSXWRJQHKQ-UPHRSURJSA-N 0.000 description 1
- SEGOWPZYUBAKGW-WAYWQWQTSA-N (Z)-4-oxo-4-pentan-2-yloxybut-2-enoic acid Chemical compound CCCC(C)OC(=O)\C=C/C(O)=O SEGOWPZYUBAKGW-WAYWQWQTSA-N 0.000 description 1
- CSRPULGNFIOKDV-IHWYPQMZSA-N (z)-4-(2-cyanoethoxy)-4-oxobut-2-enoic acid Chemical compound OC(=O)\C=C/C(=O)OCCC#N CSRPULGNFIOKDV-IHWYPQMZSA-N 0.000 description 1
- KITWNHAYBHUALA-WAYWQWQTSA-N (z)-4-oxo-4-pentan-3-yloxybut-2-enoic acid Chemical compound CCC(CC)OC(=O)\C=C/C(O)=O KITWNHAYBHUALA-WAYWQWQTSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
- HRAQMGWTPNOILP-UHFFFAOYSA-N 4-Ethoxy ethylbenzoate Chemical compound CCOC(=O)C1=CC=C(OCC)C=C1 HRAQMGWTPNOILP-UHFFFAOYSA-N 0.000 description 1
- XYOGINVXBLNFCQ-NTMALXAHSA-N CCOC(=O)\C=C(\CC(C)(C)C)C(=O)OCC Chemical compound CCOC(=O)\C=C(\CC(C)(C)C)C(=O)OCC XYOGINVXBLNFCQ-NTMALXAHSA-N 0.000 description 1
- IEPRKVQEAMIZSS-WAYWQWQTSA-N Diethyl maleate Chemical compound CCOC(=O)\C=C/C(=O)OCC IEPRKVQEAMIZSS-WAYWQWQTSA-N 0.000 description 1
- WWALDYQQSKTKNJ-IHWYPQMZSA-N NCCCOC(/C=C\C(O)=O)=O Chemical compound NCCCOC(/C=C\C(O)=O)=O WWALDYQQSKTKNJ-IHWYPQMZSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- CVBUWTZVGPMNOG-ZCXUNETKSA-N bis(2-methylpropyl) (z)-2,3-bis(2-methylpropyl)but-2-enedioate Chemical compound CC(C)COC(=O)C(\CC(C)C)=C(\CC(C)C)C(=O)OCC(C)C CVBUWTZVGPMNOG-ZCXUNETKSA-N 0.000 description 1
- UGAKVTOULBYYTM-DQRAZIAOSA-N bis(2-methylpropyl) (z)-2,3-dicyclohexylbut-2-enedioate Chemical compound C1CCCCC1/C(C(=O)OCC(C)C)=C(C(=O)OCC(C)C)\C1CCCCC1 UGAKVTOULBYYTM-DQRAZIAOSA-N 0.000 description 1
- PGJWSDBGQNOWDQ-VXPUYCOJSA-N bis(2-methylpropyl) (z)-2,3-dicyclopentylbut-2-enedioate Chemical compound C1CCCC1/C(C(=O)OCC(C)C)=C(C(=O)OCC(C)C)\C1CCCC1 PGJWSDBGQNOWDQ-VXPUYCOJSA-N 0.000 description 1
- ADLSSALNIVAOPI-FLWNBWAVSA-N bis(2-methylpropyl) (z)-2,3-didecylbut-2-enedioate Chemical compound CCCCCCCCCC\C(C(=O)OCC(C)C)=C(C(=O)OCC(C)C)/CCCCCCCCCC ADLSSALNIVAOPI-FLWNBWAVSA-N 0.000 description 1
- NCPPAVPRTMLCLD-VXPUYCOJSA-N bis(2-methylpropyl) (z)-2,3-dipentylbut-2-enedioate Chemical compound CCCCC\C(C(=O)OCC(C)C)=C(/CCCCC)C(=O)OCC(C)C NCPPAVPRTMLCLD-VXPUYCOJSA-N 0.000 description 1
- PIPOXTSGUUUZAI-ZSOIEALJSA-N bis(2-methylpropyl) (z)-2-(2-methylpropyl)but-2-enedioate Chemical compound CC(C)COC(=O)\C=C(\CC(C)C)C(=O)OCC(C)C PIPOXTSGUUUZAI-ZSOIEALJSA-N 0.000 description 1
- XUTVVNBJMQDOFX-HNENSFHCSA-N bis(2-methylpropyl) (z)-2-butyl-3-pentylbut-2-enedioate Chemical compound CCCCC\C(C(=O)OCC(C)C)=C(/CCCC)C(=O)OCC(C)C XUTVVNBJMQDOFX-HNENSFHCSA-N 0.000 description 1
- AYNYZGGRJPGGDI-HNENSFHCSA-N bis(2-methylpropyl) (z)-2-cyclohexyl-3-propan-2-ylbut-2-enedioate Chemical compound CC(C)COC(=O)C(\C(C)C)=C(C(=O)OCC(C)C)\C1CCCCC1 AYNYZGGRJPGGDI-HNENSFHCSA-N 0.000 description 1
- AEVCTEYSPQZLDW-YBEGLDIGSA-N bis(2-methylpropyl) (z)-2-cyclohexylbut-2-enedioate Chemical compound CC(C)COC(=O)\C=C(C(=O)OCC(C)C)\C1CCCCC1 AEVCTEYSPQZLDW-YBEGLDIGSA-N 0.000 description 1
- QKXUHRSXBFNCMN-DHDCSXOGSA-N bis(2-methylpropyl) (z)-2-cyclopentylbut-2-enedioate Chemical compound CC(C)COC(=O)\C=C(C(=O)OCC(C)C)\C1CCCC1 QKXUHRSXBFNCMN-DHDCSXOGSA-N 0.000 description 1
- YXZNZFCPOBHHBC-HKWRFOASSA-N bis(2-methylpropyl) (z)-2-decylbut-2-enedioate Chemical compound CCCCCCCCCC\C(C(=O)OCC(C)C)=C\C(=O)OCC(C)C YXZNZFCPOBHHBC-HKWRFOASSA-N 0.000 description 1
- LDAVSTVRYUVSAR-PFONDFGASA-N bis(2-methylpropyl) (z)-2-methyl-3-(2-methylpropyl)but-2-enedioate Chemical compound CC(C)COC(=O)C(\C)=C(\CC(C)C)C(=O)OCC(C)C LDAVSTVRYUVSAR-PFONDFGASA-N 0.000 description 1
- MQNFMAQFNMWVCO-GDNBJRDFSA-N bis(2-methylpropyl) (z)-2-pentylbut-2-enedioate Chemical compound CCCCC\C(C(=O)OCC(C)C)=C\C(=O)OCC(C)C MQNFMAQFNMWVCO-GDNBJRDFSA-N 0.000 description 1
- LCSBBYDVURYNNO-YPKPFQOOSA-N bis(3,3,3-trifluoropropyl) (z)-2,3-bis(2-methylpropyl)but-2-enedioate Chemical compound FC(F)(F)CCOC(=O)C(/CC(C)C)=C(/CC(C)C)C(=O)OCCC(F)(F)F LCSBBYDVURYNNO-YPKPFQOOSA-N 0.000 description 1
- SLAGLRZEZMHSGH-NTMALXAHSA-N bis(3,3,3-trifluoropropyl) (z)-2-(2-methylpropyl)but-2-enedioate Chemical compound FC(F)(F)CCOC(=O)C(/CC(C)C)=C\C(=O)OCCC(F)(F)F SLAGLRZEZMHSGH-NTMALXAHSA-N 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 150000004699 copper complex Chemical class 0.000 description 1
- HJRJDOWDYGURNY-UHFFFAOYSA-N copper(1+) methylsulfanylmethane Chemical compound [Cu+].CSC HJRJDOWDYGURNY-UHFFFAOYSA-N 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- NVIAHYICUFIYJC-ZCXUNETKSA-N dibutyl (z)-2,3-bis(2-methylpropyl)but-2-enedioate Chemical compound CCCCOC(=O)C(\CC(C)C)=C(\CC(C)C)C(=O)OCCCC NVIAHYICUFIYJC-ZCXUNETKSA-N 0.000 description 1
- XNPJNYBSKLALIF-DQRAZIAOSA-N dibutyl (z)-2,3-dicyclohexylbut-2-enedioate Chemical compound C1CCCCC1/C(C(=O)OCCCC)=C(C(=O)OCCCC)\C1CCCCC1 XNPJNYBSKLALIF-DQRAZIAOSA-N 0.000 description 1
- MNLXWJQPWZPLBR-OWBHPGMISA-N dibutyl (z)-2-(2-methylpropyl)but-2-enedioate Chemical compound CCCCOC(=O)\C=C(\CC(C)C)C(=O)OCCCC MNLXWJQPWZPLBR-OWBHPGMISA-N 0.000 description 1
- QOCRYVQHSSGJHZ-VXPUYCOJSA-N dibutyl (z)-2-butan-2-yl-3-cyclohexylbut-2-enedioate Chemical compound CCCCOC(=O)C(\C(C)CC)=C(C(=O)OCCCC)\C1CCCCC1 QOCRYVQHSSGJHZ-VXPUYCOJSA-N 0.000 description 1
- KRDMOZGLJXXSBQ-PEZBUJJGSA-N dibutyl (z)-2-cyclohexylbut-2-enedioate Chemical compound CCCCOC(=O)\C=C(C(=O)OCCCC)\C1CCCCC1 KRDMOZGLJXXSBQ-PEZBUJJGSA-N 0.000 description 1
- ZOBOGPBFVNLURY-PFONDFGASA-N dibutyl (z)-2-methyl-3-(2-methylpropyl)but-2-enedioate Chemical compound CCCCOC(=O)C(\C)=C(\CC(C)C)C(=O)OCCCC ZOBOGPBFVNLURY-PFONDFGASA-N 0.000 description 1
- WLXWYFSEDCUYPD-FCQUAONHSA-N didecyl (z)-2-methylbut-2-enedioate Chemical compound CCCCCCCCCCOC(=O)\C=C(\C)C(=O)OCCCCCCCCCC WLXWYFSEDCUYPD-FCQUAONHSA-N 0.000 description 1
- ORHXMVRSOXJFRO-NXVVXOECSA-N diethyl (Z)-2,3-bis(3-methylbutyl)but-2-enedioate Chemical compound CCOC(=O)C(\CCC(C)C)=C(\CCC(C)C)C(=O)OCC ORHXMVRSOXJFRO-NXVVXOECSA-N 0.000 description 1
- YULCXIXHLRTIOT-YPKPFQOOSA-N diethyl (z)-2,3-bis(2,2-dimethylpropyl)but-2-enedioate Chemical compound CCOC(=O)C(\CC(C)(C)C)=C(\CC(C)(C)C)C(=O)OCC YULCXIXHLRTIOT-YPKPFQOOSA-N 0.000 description 1
- UKGPJHMCLZJZOJ-YPKPFQOOSA-N diethyl (z)-2,3-bis(2-methylpropyl)but-2-enedioate Chemical compound CCOC(=O)C(\CC(C)C)=C(\CC(C)C)C(=O)OCC UKGPJHMCLZJZOJ-YPKPFQOOSA-N 0.000 description 1
- PEJGJUZQXNJNRN-ZCXUNETKSA-N diethyl (z)-2,3-dicyclohexylbut-2-enedioate Chemical compound C1CCCCC1/C(C(=O)OCC)=C(C(=O)OCC)\C1CCCCC1 PEJGJUZQXNJNRN-ZCXUNETKSA-N 0.000 description 1
- RJWRITVZLYWBGJ-NXVVXOECSA-N diethyl (z)-2,3-dicyclopentylbut-2-enedioate Chemical compound C1CCCC1/C(C(=O)OCC)=C(C(=O)OCC)\C1CCCC1 RJWRITVZLYWBGJ-NXVVXOECSA-N 0.000 description 1
- MCJYECSJHCLPAD-QPLCGJKRSA-N diethyl (z)-2,3-didecylbut-2-enedioate Chemical compound CCCCCCCCCC\C(C(=O)OCC)=C(C(=O)OCC)/CCCCCCCCCC MCJYECSJHCLPAD-QPLCGJKRSA-N 0.000 description 1
- LLKGSLDFLYDTMI-FPLPWBNLSA-N diethyl (z)-2,3-dimethylbut-2-enedioate Chemical compound CCOC(=O)C(\C)=C(\C)C(=O)OCC LLKGSLDFLYDTMI-FPLPWBNLSA-N 0.000 description 1
- IYNBRDAONWYDLW-NXVVXOECSA-N diethyl (z)-2,3-dipentylbut-2-enedioate Chemical compound CCCCC\C(C(=O)OCC)=C(C(=O)OCC)/CCCCC IYNBRDAONWYDLW-NXVVXOECSA-N 0.000 description 1
- CIGUSIACNVMZHH-NTMALXAHSA-N diethyl (z)-2-(2-methylpropyl)but-2-enedioate Chemical compound CCOC(=O)\C=C(\CC(C)C)C(=O)OCC CIGUSIACNVMZHH-NTMALXAHSA-N 0.000 description 1
- NZPXZLRNZYHLKO-QBFSEMIESA-N diethyl (z)-2-benzylbut-2-enedioate Chemical compound CCOC(=O)\C=C(C(=O)OCC)\CC1=CC=CC=C1 NZPXZLRNZYHLKO-QBFSEMIESA-N 0.000 description 1
- MJXUIWOBYQQHRY-KTKRTIGZSA-N diethyl (z)-2-butylbut-2-enedioate Chemical compound CCCC\C(C(=O)OCC)=C\C(=O)OCC MJXUIWOBYQQHRY-KTKRTIGZSA-N 0.000 description 1
- WZRHHXXSMZRMDV-BENRWUELSA-N diethyl (z)-2-cyclohexylbut-2-enedioate Chemical compound CCOC(=O)\C=C(C(=O)OCC)\C1CCCCC1 WZRHHXXSMZRMDV-BENRWUELSA-N 0.000 description 1
- BTFXYBXWLNJQSA-LUAWRHEFSA-N diethyl (z)-2-cyclopentylbut-2-enedioate Chemical compound CCOC(=O)\C=C(C(=O)OCC)\C1CCCC1 BTFXYBXWLNJQSA-LUAWRHEFSA-N 0.000 description 1
- YPTLFOZCUOHVFO-SREVYHEPSA-N diethyl (z)-2-methylbut-2-enedioate Chemical compound CCOC(=O)\C=C(\C)C(=O)OCC YPTLFOZCUOHVFO-SREVYHEPSA-N 0.000 description 1
- FOCVPBCYBCRXFC-KHPPLWFESA-N diethyl (z)-2-pentylbut-2-enedioate Chemical compound CCCCC\C(C(=O)OCC)=C\C(=O)OCC FOCVPBCYBCRXFC-KHPPLWFESA-N 0.000 description 1
- 239000003085 diluting agent Substances 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
- XRMFFMYQZPXEFQ-YPKPFQOOSA-N dimethyl (z)-2,3-dicyclopentylbut-2-enedioate Chemical compound C1CCCC1/C(C(=O)OC)=C(C(=O)OC)\C1CCCC1 XRMFFMYQZPXEFQ-YPKPFQOOSA-N 0.000 description 1
- CPYCIMQVKWHLCF-CLFYSBASSA-N dimethyl (z)-2-cyclopentylbut-2-enedioate Chemical compound COC(=O)\C=C(C(=O)OC)\C1CCCC1 CPYCIMQVKWHLCF-CLFYSBASSA-N 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000008570 general process Effects 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- UWNADWZGEHDQAB-UHFFFAOYSA-N i-Pr2C2H4i-Pr2 Natural products CC(C)CCC(C)C UWNADWZGEHDQAB-UHFFFAOYSA-N 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- YSMZEMQBSONIMJ-UHFFFAOYSA-M magnesium;2-methanidylpropane;chloride Chemical compound [Mg+2].[Cl-].CC(C)[CH2-] YSMZEMQBSONIMJ-UHFFFAOYSA-M 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 150000002689 maleic acids Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000012798 spherical particle Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000725 trifluoropropyl group Chemical group [H]C([H])(*)C([H])([H])C(F)(F)F 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 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
-
- 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
- C08F4/651—Pretreating with non-metals or metal-free 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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01203468 | 2001-09-13 | ||
| EP01203468 | 2001-09-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2297014T3 true ES2297014T3 (es) | 2008-05-01 |
Family
ID=8180925
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES02779321T Expired - Lifetime ES2297014T3 (es) | 2001-09-13 | 2002-09-04 | Componentes y catalizadores para la polimerizacion de olefinas. |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US7015170B2 (OSRAM) |
| EP (1) | EP1425317B1 (OSRAM) |
| JP (1) | JP4295101B2 (OSRAM) |
| KR (1) | KR20040028674A (OSRAM) |
| CN (1) | CN100415778C (OSRAM) |
| AT (1) | ATE381579T1 (OSRAM) |
| BR (1) | BR0206037A (OSRAM) |
| DE (1) | DE60224205T2 (OSRAM) |
| ES (1) | ES2297014T3 (OSRAM) |
| WO (1) | WO2003022894A1 (OSRAM) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100338018C (zh) | 2004-10-29 | 2007-09-19 | 中国石油化工股份有限公司 | 一种环戊酯类化合物及其合成方法和应用 |
| CN101824108B (zh) * | 2009-03-04 | 2012-03-07 | 中国石油天然气股份有限公司 | 一种齐格勒-纳塔催化剂 |
| CN101824106B (zh) * | 2009-03-04 | 2012-05-30 | 中国石油天然气股份有限公司 | 烯烃聚合用催化组分及其催化剂 |
| WO2012070753A2 (ko) * | 2010-11-24 | 2012-05-31 | 삼성토탈 주식회사 | 프로필렌 중합용 고체촉매 및 그 제조 방법 |
| KR101235445B1 (ko) | 2010-01-13 | 2013-02-20 | 삼성토탈 주식회사 | 프로필렌 중합용 고체촉매의 제조 방법 |
| CN102268109B (zh) * | 2010-06-04 | 2012-11-14 | 中国石油天然气股份有限公司 | 一种用于烯烃聚合的固体钛催化剂 |
| CN102212153B (zh) * | 2011-04-19 | 2014-04-02 | 中国科学院化学研究所 | 含马来酸二酯的烯烃聚合催化剂固体组分及其制备方法 |
| US10308740B2 (en) | 2014-02-07 | 2019-06-04 | Eastman Chemical Company | Amorphous propylene-ethylene copolymers |
| US9399686B2 (en) | 2014-02-07 | 2016-07-26 | Eastman Chemical Company | Amorphous propylene-ethylene copolymers |
| US11267916B2 (en) | 2014-02-07 | 2022-03-08 | Eastman Chemical Company | Adhesive composition comprising amorphous propylene-ethylene copolymer and polyolefins |
| US10696765B2 (en) | 2014-02-07 | 2020-06-30 | Eastman Chemical Company | Adhesive composition comprising amorphous propylene-ethylene copolymer and propylene polymer |
| US10647795B2 (en) | 2014-02-07 | 2020-05-12 | Eastman Chemical Company | Adhesive composition comprising amorphous propylene-ethylene copolymer and polyolefins |
| US10723824B2 (en) | 2014-02-07 | 2020-07-28 | Eastman Chemical Company | Adhesives comprising amorphous propylene-ethylene copolymers |
| US10626199B2 (en) | 2014-12-22 | 2020-04-21 | Borealis Ag | Process for producing polypropylene |
| CN106608934B (zh) * | 2015-10-27 | 2019-03-22 | 中国石油化工股份有限公司 | 催化剂组分及其制备方法和应用和用于烯烃聚合的催化剂体系及其应用和烯烃聚合方法 |
| CN106608923B (zh) * | 2015-10-27 | 2019-03-26 | 中国石油化工股份有限公司 | 催化剂组分及其制备方法和应用和用于烯烃聚合的催化剂体系及其应用和烯烃聚合方法 |
| US11466107B2 (en) * | 2018-02-05 | 2022-10-11 | Basell Poliolefine Italia S.R.L. | Components and catalysts for the polymerization of olefins |
| US12234351B2 (en) * | 2019-01-15 | 2025-02-25 | Borealis Ag | Random propylene polymer composition and use in extrusion blow moulding |
| CN116041577B (zh) | 2021-10-28 | 2024-12-06 | 中国石油化工股份有限公司 | 烯烃聚合催化剂组分、催化剂体系及应用和烯烃聚合方法 |
| EP4617293A1 (en) | 2024-03-14 | 2025-09-17 | Lummus Novolen Technology GmbH | Phtalate-free ziegler-natta catalysts using mixed internal donors to adjust achievable xs range |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK133012C (da) | 1968-11-21 | 1976-08-09 | Montedison Spa | Katalysator til polymerisation af alkener |
| YU35844B (en) | 1968-11-25 | 1981-08-31 | Montedison Spa | Process for obtaining catalysts for the polymerization of olefines |
| GB1603724A (en) | 1977-05-25 | 1981-11-25 | Montedison Spa | Components and catalysts for the polymerisation of alpha-olefins |
| IT1096661B (it) | 1978-06-13 | 1985-08-26 | Montedison Spa | Procedimento per la preparazione di prodotti in forma sferoidale solidi a temperatura ambiente |
| IT1098272B (it) | 1978-08-22 | 1985-09-07 | Montedison Spa | Componenti,di catalizzatori e catalizzatori per la polimerizzazione delle alfa-olefine |
| IT1209255B (it) | 1980-08-13 | 1989-07-16 | Montedison Spa | Catalizzatori per la polimerizzazione di olefine. |
| JPS58138708A (ja) | 1982-02-12 | 1983-08-17 | Mitsui Petrochem Ind Ltd | オレフイン系重合体の製造方法 |
| EP0350170B2 (en) * | 1988-06-17 | 2001-09-12 | Mitsui Chemicals, Inc. | Process for polymerising olefins and polymerisation catalyst therefor |
| IT1230134B (it) | 1989-04-28 | 1991-10-14 | Himont Inc | Componenti e catalizzatori per la polimerizzazione di olefine. |
| DE3932553A1 (de) | 1989-09-29 | 1991-04-11 | Basf Ag | Katalysatorsysteme vom typ der ziegler-natta-katalysatoren |
| FI90985C (fi) | 1991-10-02 | 1994-04-25 | Neste Oy | Tehokkaan elektronidonorin sisältävä polymerointikatalyytin prokatalyyttikompositio |
| IT1262934B (it) | 1992-01-31 | 1996-07-22 | Montecatini Tecnologie Srl | Componenti e catalizzatori per la polimerizzazione di olefine |
| IT1262935B (it) | 1992-01-31 | 1996-07-22 | Montecatini Tecnologie Srl | Componenti e catalizzatori per la polimerizzazione di olefine |
| IT1256648B (it) | 1992-12-11 | 1995-12-12 | Montecatini Tecnologie Srl | Componenti e catalizzatori per la polimerizzazione delle olefine |
| ES2213898T3 (es) | 1997-03-29 | 2004-09-01 | Basell Poliolefine Italia S.P.A. | Aductos de dicloruro de magnesio/alcohol, procedimiento para su preparacion y componentes catalizadores obtenidos a partir de estos. |
| IT1292107B1 (it) * | 1997-06-09 | 1999-01-25 | Montell North America Inc | Componenti e catalizzatori per la polimerizzazione di olefine |
| WO2000039171A1 (en) | 1998-12-25 | 2000-07-06 | Toho Titanium Co., Ltd. | Solid catalyst component for propylene polymerization and catalyst |
| US6469112B2 (en) | 2000-08-22 | 2002-10-22 | Engelhard Corporation | (Cycloalkyl)methyl silanes as external donors for polyolefin catalysts |
-
2002
- 2002-09-04 CN CNB028028856A patent/CN100415778C/zh not_active Expired - Lifetime
- 2002-09-04 EP EP02779321A patent/EP1425317B1/en not_active Expired - Lifetime
- 2002-09-04 ES ES02779321T patent/ES2297014T3/es not_active Expired - Lifetime
- 2002-09-04 US US10/415,025 patent/US7015170B2/en not_active Expired - Lifetime
- 2002-09-04 AT AT02779321T patent/ATE381579T1/de not_active IP Right Cessation
- 2002-09-04 KR KR10-2003-7005993A patent/KR20040028674A/ko not_active Withdrawn
- 2002-09-04 WO PCT/EP2002/010049 patent/WO2003022894A1/en not_active Ceased
- 2002-09-04 BR BR0206037-0A patent/BR0206037A/pt not_active IP Right Cessation
- 2002-09-04 JP JP2003526965A patent/JP4295101B2/ja not_active Expired - Lifetime
- 2002-09-04 DE DE60224205T patent/DE60224205T2/de not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US7015170B2 (en) | 2006-03-21 |
| CN100415778C (zh) | 2008-09-03 |
| JP4295101B2 (ja) | 2009-07-15 |
| ATE381579T1 (de) | 2008-01-15 |
| KR20040028674A (ko) | 2004-04-03 |
| EP1425317B1 (en) | 2007-12-19 |
| EP1425317A1 (en) | 2004-06-09 |
| US20040014595A1 (en) | 2004-01-22 |
| JP2005502743A (ja) | 2005-01-27 |
| BR0206037A (pt) | 2003-09-09 |
| WO2003022894A1 (en) | 2003-03-20 |
| CN1714105A (zh) | 2005-12-28 |
| DE60224205D1 (de) | 2008-01-31 |
| DE60224205T2 (de) | 2008-12-11 |
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