CA2148596A1 - Methode de polymerisation d'alpha-olefines - Google Patents

Methode de polymerisation d'alpha-olefines

Info

Publication number: CA2148596A1
Authority: CA; Canada
Prior art keywords: carbon atoms; group; magnesium; process according; compound
Prior art date: 1992-11-06
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.): Abandoned

Application number

CA002148596A

Other languages

English (en)

Inventor

David Bell Morse

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Shell USA Inc

Original Assignee

Individual

Priority date (The priority date 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 date listed.)

1992-11-06

Filing date

1993-11-05

Publication date

1994-05-26

1993-11-05 Application filed by Individual filed Critical Individual

1994-05-26 Publication of CA2148596A1 publication Critical patent/CA2148596A1/fr

Status Abandoned legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 35
230000008569 process Effects 0.000 title claims abstract description 32
230000000379 polymerizing effect Effects 0.000 title claims abstract 3
239000004711 α-olefin Substances 0.000 title 1
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 44
239000003795 chemical substances by application Substances 0.000 claims abstract description 29
239000003054 catalyst Substances 0.000 claims abstract description 24
150000003609 titanium compounds Chemical class 0.000 claims abstract description 23
238000006116 polymerization reaction Methods 0.000 claims abstract description 19
229910052749 magnesium Inorganic materials 0.000 claims abstract description 17
239000011777 magnesium Substances 0.000 claims abstract description 17
239000010936 titanium Substances 0.000 claims abstract description 17
229910052719 titanium Inorganic materials 0.000 claims abstract description 17
-1 titanium halide Chemical class 0.000 claims abstract description 17
150000002681 magnesium compounds Chemical class 0.000 claims abstract description 15
125000000217 alkyl group Chemical group 0.000 claims abstract description 14
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims abstract description 13
150000005826 halohydrocarbons Chemical class 0.000 claims abstract description 12
150000001282 organosilanes Chemical class 0.000 claims abstract description 12
239000002253 acid Substances 0.000 claims abstract description 9
150000004703 alkoxides Chemical group 0.000 claims abstract description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 8
150000002148 esters Chemical class 0.000 claims abstract description 7
229910052736 halogen Inorganic materials 0.000 claims abstract description 7
150000002367 halogens Chemical class 0.000 claims abstract description 7
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 5
125000002877 alkyl aryl group Chemical group 0.000 claims abstract description 4
150000001875 compounds Chemical class 0.000 claims description 25
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 16
239000000203 mixture Substances 0.000 claims description 15
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 14
239000002685 polymerization catalyst Substances 0.000 claims description 9
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 9
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 9
150000001336 alkenes Chemical class 0.000 claims description 8
MGWAVDBGNNKXQV-UHFFFAOYSA-N diisobutyl phthalate Chemical group CC(C)COC(=O)C1=CC=CC=C1C(=O)OCC(C)C MGWAVDBGNNKXQV-UHFFFAOYSA-N 0.000 claims description 8
125000005843 halogen group Chemical group 0.000 claims description 8
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 8
125000003545 alkoxy group Chemical group 0.000 claims description 7
125000004429 atom Chemical group 0.000 claims description 7
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 claims description 6
XDKQUSKHRIUJEO-UHFFFAOYSA-N magnesium;ethanolate Chemical compound [Mg+2].CC[O-].CC[O-] XDKQUSKHRIUJEO-UHFFFAOYSA-N 0.000 claims description 5
IBSQPLPBRSHTTG-UHFFFAOYSA-N 1-chloro-2-methylbenzene Chemical compound CC1=CC=CC=C1Cl IBSQPLPBRSHTTG-UHFFFAOYSA-N 0.000 claims description 4
125000004104 aryloxy group Chemical group 0.000 claims description 4
125000001183 hydrocarbyl group Chemical group 0.000 claims description 4
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 4
SLYCYWCVSGPDFR-UHFFFAOYSA-N octadecyltrimethoxysilane Chemical compound CCCCCCCCCCCCCCCCCC[Si](OC)(OC)OC SLYCYWCVSGPDFR-UHFFFAOYSA-N 0.000 claims description 4
125000005587 carbonate group Chemical group 0.000 claims description 3
UBCPEZPOCJYHPM-UHFFFAOYSA-N dimethoxy-methyl-octadecylsilane Chemical compound CCCCCCCCCCCCCCCCCC[Si](C)(OC)OC UBCPEZPOCJYHPM-UHFFFAOYSA-N 0.000 claims description 3
150000004820 halides Chemical class 0.000 claims description 3
230000002140 halogenating effect Effects 0.000 claims description 3
FZMJEGJVKFTGMU-UHFFFAOYSA-N triethoxy(octadecyl)silane Chemical group CCCCCCCCCCCCCCCCCC[Si](OCC)(OCC)OCC FZMJEGJVKFTGMU-UHFFFAOYSA-N 0.000 claims description 3
OESYAPCYPZGMRH-UHFFFAOYSA-N trimethoxy(triacontyl)silane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCC[Si](OC)(OC)OC OESYAPCYPZGMRH-UHFFFAOYSA-N 0.000 claims description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
DJVQMRRXRRBRIH-UHFFFAOYSA-N diethoxy-methyl-octadecylsilane Chemical compound CCCCCCCCCCCCCCCCCC[Si](C)(OCC)OCC DJVQMRRXRRBRIH-UHFFFAOYSA-N 0.000 claims 2
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
239000005977 Ethylene Substances 0.000 claims 1
150000008282 halocarbons Chemical class 0.000 claims 1
LWJZSHFCERSHME-UHFFFAOYSA-N triethoxy(triacontyl)silane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCC[Si](OCC)(OCC)OCC LWJZSHFCERSHME-UHFFFAOYSA-N 0.000 claims 1
229920000642 polymer Polymers 0.000 abstract description 18
238000009826 distribution Methods 0.000 abstract description 4
125000002370 organoaluminium group Chemical group 0.000 abstract 1
239000000047 product Substances 0.000 description 19
239000007787 solid Substances 0.000 description 8
150000002500 ions Chemical class 0.000 description 7
239000002002 slurry Substances 0.000 description 7
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
229910052799 carbon Inorganic materials 0.000 description 6
239000012071 phase Substances 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 5
230000000052 comparative effect Effects 0.000 description 5
229920001577 copolymer Polymers 0.000 description 5
VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
125000003118 aryl group Chemical group 0.000 description 4
229910052801 chlorine Inorganic materials 0.000 description 4
239000000460 chlorine Substances 0.000 description 4
239000003085 diluting agent Substances 0.000 description 4
229920001519 homopolymer Polymers 0.000 description 4
239000001257 hydrogen Substances 0.000 description 4
229910052739 hydrogen Inorganic materials 0.000 description 4
QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 4
239000000155 melt Substances 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 4
BHMLFPOTZYRDKA-IRXDYDNUSA-N (2s)-2-[(s)-(2-iodophenoxy)-phenylmethyl]morpholine Chemical compound IC1=CC=CC=C1O[C@@H](C=1C=CC=CC=1)[C@H]1OCCNC1 BHMLFPOTZYRDKA-IRXDYDNUSA-N 0.000 description 3
HRAQMGWTPNOILP-UHFFFAOYSA-N 4-Ethoxy ethylbenzoate Chemical compound CCOC(=O)C1=CC=C(OCC)C=C1 HRAQMGWTPNOILP-UHFFFAOYSA-N 0.000 description 3
229910003074 TiCl4 Inorganic materials 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
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 3
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 3
230000000694 effects Effects 0.000 description 3
239000007789 gas Substances 0.000 description 3
230000026030 halogenation Effects 0.000 description 3
238000005658 halogenation reaction Methods 0.000 description 3
239000007788 liquid Substances 0.000 description 3
239000007791 liquid phase Substances 0.000 description 3
239000000178 monomer Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000002245 particle Substances 0.000 description 3
230000009467 reduction Effects 0.000 description 3
UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 2
OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 2
UWNADWZGEHDQAB-UHFFFAOYSA-N 2,5-dimethylhexane Chemical group CC(C)CCC(C)C UWNADWZGEHDQAB-UHFFFAOYSA-N 0.000 description 2
KEVMYFLMMDUPJE-UHFFFAOYSA-N 2,7-dimethyloctane Chemical group CC(C)CCCCC(C)C KEVMYFLMMDUPJE-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
241000282326 Felis catus Species 0.000 description 2
NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 2
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
FYXKZNLBZKRYSS-UHFFFAOYSA-N benzene-1,2-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC=C1C(Cl)=O FYXKZNLBZKRYSS-UHFFFAOYSA-N 0.000 description 2
QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
150000001805 chlorine compounds Chemical class 0.000 description 2
238000010924 continuous production Methods 0.000 description 2
229940117389 dichlorobenzene Drugs 0.000 description 2
AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 2
JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 2
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 2
239000012467 final product Substances 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
229920000098 polyolefin Polymers 0.000 description 2
239000012429 reaction media Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
FNAIRYWIXALZFN-UHFFFAOYSA-N 1,1,1-trichloro-8-fluorooctane Chemical compound FCCCCCCCC(Cl)(Cl)Cl FNAIRYWIXALZFN-UHFFFAOYSA-N 0.000 description 1
AVGQTJUPLKNPQP-UHFFFAOYSA-N 1,1,1-trichloropropane Chemical compound CCC(Cl)(Cl)Cl AVGQTJUPLKNPQP-UHFFFAOYSA-N 0.000 description 1
SEQRDAAUNCRFIT-UHFFFAOYSA-N 1,1-dichlorobutane Chemical compound CCCC(Cl)Cl SEQRDAAUNCRFIT-UHFFFAOYSA-N 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 1
CUEJHYHGUMAGBP-UHFFFAOYSA-N 2-[2-(1h-indol-5-yl)phenyl]acetic acid Chemical compound OC(=O)CC1=CC=CC=C1C1=CC=C(NC=C2)C2=C1 CUEJHYHGUMAGBP-UHFFFAOYSA-N 0.000 description 1
CAHQGWAXKLQREW-UHFFFAOYSA-N Benzal chloride Chemical compound ClC(Cl)C1=CC=CC=C1 CAHQGWAXKLQREW-UHFFFAOYSA-N 0.000 description 1
NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
GAKBIFMUIMALON-UHFFFAOYSA-N CC(C)(C)CC(C)(Cl)C(Cl)(Cl)Cl Chemical compound CC(C)(C)CC(C)(Cl)C(Cl)(Cl)Cl GAKBIFMUIMALON-UHFFFAOYSA-N 0.000 description 1
ZFAGXQVYYWOLNK-UHFFFAOYSA-N CCO[Mg] Chemical compound CCO[Mg] ZFAGXQVYYWOLNK-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 1
VQUOFRWKEZSLML-UHFFFAOYSA-N ClC1=CC=CC=C1.ClC1=CC=CC2=CC=CC=C12 Chemical compound ClC1=CC=CC=C1.ClC1=CC=CC2=CC=CC=C12 VQUOFRWKEZSLML-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
101000740224 Homo sapiens Protein SCAI Proteins 0.000 description 1
DTAFLBZLAZYRDX-UHFFFAOYSA-N OOOOOO Chemical compound OOOOOO DTAFLBZLAZYRDX-UHFFFAOYSA-N 0.000 description 1
YAVWDJDEOLOYQO-UHFFFAOYSA-N OOOOOOOOOO Chemical compound OOOOOOOOOO YAVWDJDEOLOYQO-UHFFFAOYSA-N 0.000 description 1
239000004743 Polypropylene Substances 0.000 description 1
102100037197 Protein SCAI Human genes 0.000 description 1
230000018199 S phase Effects 0.000 description 1
241001417495 Serranidae Species 0.000 description 1
BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
CJWANOYUFBSCHS-UHFFFAOYSA-L [Br-].[Br-].CCO[Ti+2]OCC Chemical compound [Br-].[Br-].CCO[Ti+2]OCC CJWANOYUFBSCHS-UHFFFAOYSA-L 0.000 description 1
ADKPKEZZYOUGBZ-UHFFFAOYSA-N [C].[O].[Si] Chemical compound [C].[O].[Si] ADKPKEZZYOUGBZ-UHFFFAOYSA-N 0.000 description 1
MJAANYBZHGEMLW-UHFFFAOYSA-K [I-].[I-].[I-].CC(C)O[Ti+3] Chemical compound [I-].[I-].[I-].CC(C)O[Ti+3] MJAANYBZHGEMLW-UHFFFAOYSA-K 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
150000001334 alicyclic compounds Chemical class 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
RBFQJDQYXXHULB-UHFFFAOYSA-N arsane Chemical class [AsH3] RBFQJDQYXXHULB-UHFFFAOYSA-N 0.000 description 1
150000008378 aryl ethers Chemical class 0.000 description 1
230000008901 benefit Effects 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
JANBFCARANRIKJ-UHFFFAOYSA-N bis(3-methylbutyl) benzene-1,2-dicarboxylate Chemical compound CC(C)CCOC(=O)C1=CC=CC=C1C(=O)OCCC(C)C JANBFCARANRIKJ-UHFFFAOYSA-N 0.000 description 1
239000012986 chain transfer agent Substances 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
229960001701 chloroform Drugs 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
150000001923 cyclic compounds Chemical class 0.000 description 1
VEVRNHHLCPGNDU-MUGJNUQGSA-O desmosine Chemical compound OC(=O)[C@@H](N)CCCC[N+]1=CC(CC[C@H](N)C(O)=O)=C(CCC[C@H](N)C(O)=O)C(CC[C@H](N)C(O)=O)=C1 VEVRNHHLCPGNDU-MUGJNUQGSA-O 0.000 description 1
FJBFPHVGVWTDIP-UHFFFAOYSA-N dibromomethane Chemical compound BrCBr FJBFPHVGVWTDIP-UHFFFAOYSA-N 0.000 description 1
125000003963 dichloro group Chemical group Cl* 0.000 description 1
QNRQOLWFDOEZPK-UHFFFAOYSA-N diethoxy(dioctadecyl)silane Chemical compound CCCCCCCCCCCCCCCCCC[Si](OCC)(OCC)CCCCCCCCCCCCCCCCCC QNRQOLWFDOEZPK-UHFFFAOYSA-N 0.000 description 1
YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 description 1
IGIHUTKDVFZAMO-UHFFFAOYSA-N dimethoxy(dioctadecyl)silane Chemical compound CCCCCCCCCCCCCCCCCC[Si](OC)(OC)CCCCCCCCCCCCCCCCCC IGIHUTKDVFZAMO-UHFFFAOYSA-N 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
HWUDSKSILZNHRX-UHFFFAOYSA-N dipropan-2-yl benzene-1,4-dicarboxylate Chemical compound CC(C)OC(=O)C1=CC=C(C(=O)OC(C)C)C=C1 HWUDSKSILZNHRX-UHFFFAOYSA-N 0.000 description 1
ZMXPNWBFRPIZFV-UHFFFAOYSA-M dipropylalumanylium;chloride Chemical compound [Cl-].CCC[Al+]CCC ZMXPNWBFRPIZFV-UHFFFAOYSA-M 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
GCPCLEKQVMKXJM-UHFFFAOYSA-N ethoxy(diethyl)alumane Chemical compound CCO[Al](CC)CC GCPCLEKQVMKXJM-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001914 filtration Methods 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
238000012685 gas phase polymerization Methods 0.000 description 1
238000005227 gel permeation chromatography Methods 0.000 description 1
VHHHONWQHHHLTI-UHFFFAOYSA-N hexachloroethane Chemical compound ClC(Cl)(Cl)C(Cl)(Cl)Cl VHHHONWQHHHLTI-UHFFFAOYSA-N 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
150000002466 imines Chemical class 0.000 description 1
230000006872 improvement Effects 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 description 1
229910001629 magnesium chloride Inorganic materials 0.000 description 1
HONQAQNYJBKAMA-UHFFFAOYSA-L magnesium;ethyl carbonate Chemical compound [Mg+2].CCOC([O-])=O.CCOC([O-])=O HONQAQNYJBKAMA-UHFFFAOYSA-L 0.000 description 1
LPGLZESAVBXHSU-UHFFFAOYSA-L magnesium;iodide;phenoxide Chemical compound [Mg+2].[I-].[O-]C1=CC=CC=C1 LPGLZESAVBXHSU-UHFFFAOYSA-L 0.000 description 1
TWXDDNPPQUTEOV-FVGYRXGTSA-N methamphetamine hydrochloride Chemical compound Cl.CN[C@@H](C)CC1=CC=CC=C1 TWXDDNPPQUTEOV-FVGYRXGTSA-N 0.000 description 1
RNHXTCZZACTEMK-UHFFFAOYSA-N methyl 4-ethoxybenzoate Chemical compound CCOC1=CC=C(C(=O)OC)C=C1 RNHXTCZZACTEMK-UHFFFAOYSA-N 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
150000003003 phosphines Chemical class 0.000 description 1
150000008039 phosphoramides Chemical class 0.000 description 1
XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
229920001155 polypropylene Polymers 0.000 description 1
OGHBATFHNDZKSO-UHFFFAOYSA-N propan-2-olate Chemical compound CC(C)[O-] OGHBATFHNDZKSO-UHFFFAOYSA-N 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910000077 silane Inorganic materials 0.000 description 1
239000000779 smoke Substances 0.000 description 1
239000011949 solid catalyst Substances 0.000 description 1
239000011343 solid material Substances 0.000 description 1
229940113046 sorine Drugs 0.000 description 1
VIDRYROWYFWGSY-UHFFFAOYSA-N sotalol hydrochloride Chemical compound Cl.CC(C)NCC(O)C1=CC=C(NS(C)(=O)=O)C=C1 VIDRYROWYFWGSY-UHFFFAOYSA-N 0.000 description 1
241000894007 species Species 0.000 description 1
OUULRIDHGPHMNQ-UHFFFAOYSA-N stibane Chemical class [SbH3] OUULRIDHGPHMNQ-UHFFFAOYSA-N 0.000 description 1
UBZYKBZMAMTNKW-UHFFFAOYSA-J titanium tetrabromide Chemical compound Br[Ti](Br)(Br)Br UBZYKBZMAMTNKW-UHFFFAOYSA-J 0.000 description 1
ZLMGMVJGEULFPP-UHFFFAOYSA-J titanium(4+) trichloride phenoxide Chemical compound Cl[Ti](Cl)(Cl)OC1=CC=CC=C1 ZLMGMVJGEULFPP-UHFFFAOYSA-J 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
150000003624 transition metals Chemical class 0.000 description 1
238000011282 treatment Methods 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
239000003039 volatile agent Substances 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
- C08F4/656—Pretreating with metals or metal-containing compounds with silicon or compounds thereof
- C08F4/6562—Pretreating with metals or metal-containing compounds with silicon or compounds thereof and metals of C08F4/64 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
- 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
- C08F110/00—Homopolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F110/02—Ethene
- 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
- 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
- C08F4/6543—Pretreating with metals or metal-containing compounds with magnesium or compounds thereof halides of magnesium

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)

CA002148596A 1992-11-06 1993-11-05 Methode de polymerisation d'alpha-olefines Abandoned CA2148596A1 (fr)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US97240292A	1992-11-06	1992-11-06
US972,402		1992-11-06
PCT/US1993/010653 WO1994011409A1 (fr)	1992-11-06	1993-11-05	Procede de polymerisation d'alpha-olefines

Publications (1)

Publication Number	Publication Date
CA2148596A1 true CA2148596A1 (fr)	1994-05-26

Family

ID=25519617

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002148596A Abandoned CA2148596A1 (fr)	1992-11-06	1993-11-05	Methode de polymerisation d'alpha-olefines

Country Status (8)

Country	Link
EP (1)	EP0667875A1 (fr)
KR (1)	KR950704372A (fr)
CN (1)	CN1092431A (fr)
AU (1)	AU5458394A (fr)
BR (1)	BR9307390A (fr)
CA (1)	CA2148596A1 (fr)
MX (1)	MX9306919A (fr)
WO (1)	WO1994011409A1 (fr)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU706739B2 (en) *	1994-05-12	1999-06-24	Showa Denko Kabushiki Kaisha	A method for the production of propylene-based polymers, catalyst component or polymerization and method for its production
US7005399B2 (en) *	2000-09-29	2006-02-28	Toho Titanium Co., Ltd.	Catalyst for polymerization of olefins
JP4371305B2 (ja)	2002-04-24	2009-11-25	シミックス・ソルーションズ・インコーポレーテッド	架橋ビス芳香族リガンド、錯体、触媒、または、重合方法およびそれにより得られるポリマー
US7060848B2 (en)	2002-04-24	2006-06-13	Symyx Technologies, Inc.	Bridged bi-aromatic catalysts, complexes, and methods of using the same
US7091292B2 (en)	2002-04-24	2006-08-15	Symyx Technologies, Inc.	Bridged bi-aromatic catalysts, complexes, and methods of using the same
CN1955195B (zh) *	2005-10-26	2010-06-16	中国石油化工股份有限公司	用于烯烃聚合或共聚合的催化剂、制备方法及应用
WO2008142130A1 (fr) *	2007-05-22	2008-11-27	Borealis Technology Oy	Système de catalyseur pour des copolymères de polypropylène
US20120208968A1 (en) *	2009-10-22	2012-08-16	Basell Polyolefine Gmbh	Catalyst components for the polymerization of olefins and catalysts therefrom obtained
CN102898556B (zh) *	2011-07-26	2015-06-17	中国石油化工股份有限公司	一种催化剂组分在烯烃聚合中的应用
CN102898555B (zh) *	2011-07-26	2015-06-17	中国石油化工股份有限公司	一种催化剂组分在烯烃聚合中的应用
CN102898557B (zh) *	2011-07-26	2015-06-17	中国石油化工股份有限公司	一种催化剂组分在烯烃聚合中的应用
CN102898558B (zh) *	2011-07-26	2015-06-17	中国石油化工股份有限公司	一种催化剂组分在烯烃聚合中的应用

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB2143834B (en) *	1983-07-20	1987-06-03	Toho Titanium Co Ltd	Polymerization catalyst
JPH06104693B2 (ja) *	1986-01-06	1994-12-21	東邦チタニウム株式会社	オレフイン類重合用触媒
CA1310955C (fr) *	1987-03-13	1992-12-01	Mamoru Kioka	Procede de polymerisation d'olefines et catalyseur correspondant

1993
- 1993-11-05 WO PCT/US1993/010653 patent/WO1994011409A1/fr not_active Ceased
- 1993-11-05 CA CA002148596A patent/CA2148596A1/fr not_active Abandoned
- 1993-11-05 AU AU54583/94A patent/AU5458394A/en not_active Abandoned
- 1993-11-05 KR KR1019950701794A patent/KR950704372A/ko not_active Withdrawn
- 1993-11-05 MX MX9306919A patent/MX9306919A/es unknown
- 1993-11-05 EP EP93925170A patent/EP0667875A1/fr not_active Ceased
- 1993-11-05 BR BR9307390-9A patent/BR9307390A/pt not_active Application Discontinuation
- 1993-11-06 CN CN93112706A patent/CN1092431A/zh active Pending

Also Published As

Publication number	Publication date
EP0667875A1 (fr)	1995-08-23
AU5458394A (en)	1994-06-08
KR950704372A (ko)	1995-11-20
WO1994011409A1 (fr)	1994-05-26
BR9307390A (pt)	1999-08-31
CN1092431A (zh)	1994-09-21
MX9306919A (es)	1995-01-31

Legal Events

Date	Code	Title	Description
1997-11-05	FZDE	Dead

Publication	Publication Date	Title
CA1187863A (fr)	1985-05-28	Catalyseur de polymerisation
CA1163617A (fr)	1984-03-13	Catalyseur de polymerisation des olefines, et procede qui y fait appel
AU763949B2 (en)	2003-08-07	Methods of making magnesium/transition metal alkoxide complexes and polymerization catalysts made therefrom
EP2420519B1 (fr)	2018-06-13	Composant catalytique utilisé pour la polymérisation d'oléfines, procédé pour le préparer, et catalyseur le contenant
CA1160202A (fr)	1984-01-10	Solide a teneur de magnesium
CA2148596A1 (fr)	1994-05-26	Methode de polymerisation d'alpha-olefines
US4707530A (en)	1987-11-17	Polymerization catalyst
US5049533A (en)	1991-09-17	Catalyst, process for preparation of same, and process for polymerization of olefins using same
AU672637B2 (en)	1996-10-10	Process for polymerizing alpha-olefin
EP0677066B1 (fr)	1998-10-14	Catalyseur de polymerisation d'olefine
JP3340729B2 (ja)	2002-11-05	α−オレフィンの重合方法
WO1994006833A1 (fr)	1994-03-31	Procede de polymerisation d'alpha-olefines
CA1338444C (fr)	1996-07-09	Constituants catalytiques solides pour la polymerisation d'alcenes; methode de preparation
CA1248694A (fr)	1989-01-10	Methode de preparation de poly(butene-1)
CA1306990C (fr)	1992-09-01	COMPOSANTS DE CATALYSEURS POUR DES CATALYSEURS DE POLYMERISATION D'.alpha.-OLEFINES ET METHODE POUR LEUR PRODUCTION
CA2001411C (fr)	1999-09-28	Procede de polymerisation d'alcenes et compositions catalysantes
US5328877A (en)	1994-07-12	Solid alkene polymerization catalyst components and process for their preparation
JPH0118926B2 (fr)	1989-04-07
JP3415912B2 (ja)	2003-06-09	結晶性ポリプロピレン
JPS5812886B2 (ja)	1983-03-10	ポリオレフインノセイゾウホウホウ
JPH0118928B2 (fr)	1989-04-07
JPH0134247B2 (fr)	1989-07-18
ZA200109190B (en)	2002-11-07	Methods of making magnesium/transition metal alkoxide complexes and polymerization catalysts made therefrom.
JPH0358371B2 (fr)	1991-09-05