ES2269135T3 - Componentes y catalizadores para la polimerizacion de olefinas. - Google Patents
Componentes y catalizadores para la polimerizacion de olefinas. Download PDFInfo
- Publication number
- ES2269135T3 ES2269135T3 ES00926912T ES00926912T ES2269135T3 ES 2269135 T3 ES2269135 T3 ES 2269135T3 ES 00926912 T ES00926912 T ES 00926912T ES 00926912 T ES00926912 T ES 00926912T ES 2269135 T3 ES2269135 T3 ES 2269135T3
- Authority
- ES
- Spain
- Prior art keywords
- succinate
- hydrogen
- catalyst
- diethyl
- catalyst component
- 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
Links
- 238000006116 polymerization reaction Methods 0.000 title claims abstract description 61
- 239000003054 catalyst Substances 0.000 title claims description 72
- 150000001336 alkenes Chemical class 0.000 title claims description 17
- 239000011949 solid catalyst Substances 0.000 claims abstract description 50
- 239000001257 hydrogen Substances 0.000 claims abstract description 42
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 42
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 25
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 22
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 22
- 125000003118 aryl group Chemical group 0.000 claims abstract description 18
- 125000002877 alkyl aryl group Chemical group 0.000 claims abstract description 16
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 14
- 229910052749 magnesium Inorganic materials 0.000 claims abstract description 14
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 13
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 13
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 12
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 12
- 229910052719 titanium Inorganic materials 0.000 claims abstract description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 10
- 150000002367 halogens Chemical class 0.000 claims abstract description 10
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 8
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 5
- 150000003890 succinate salts Chemical class 0.000 claims abstract 4
- UWNADWZGEHDQAB-UHFFFAOYSA-N i-Pr2C2H4i-Pr2 Natural products CC(C)CCC(C)C UWNADWZGEHDQAB-UHFFFAOYSA-N 0.000 claims description 83
- -1 diisobutyl 2,2-dimethyl succinate Chemical compound 0.000 claims description 60
- 238000000034 method Methods 0.000 claims description 52
- 150000001875 compounds Chemical class 0.000 claims description 48
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 34
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 33
- 239000000203 mixture Substances 0.000 claims description 33
- 239000005977 Ethylene Substances 0.000 claims description 25
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 25
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims description 23
- 239000010936 titanium Substances 0.000 claims description 21
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 19
- 239000001294 propane Substances 0.000 claims description 14
- 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 13
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 150000002148 esters Chemical class 0.000 claims description 11
- 239000000047 product Substances 0.000 claims description 9
- 239000002253 acid Chemical class 0.000 claims description 8
- 125000004429 atom Chemical group 0.000 claims description 7
- 150000002430 hydrocarbons Chemical group 0.000 claims description 7
- ZWINORFLMHROGF-UHFFFAOYSA-N 9,9-bis(methoxymethyl)fluorene Chemical compound C1=CC=C2C(COC)(COC)C3=CC=CC=C3C2=C1 ZWINORFLMHROGF-UHFFFAOYSA-N 0.000 claims description 6
- 229910052782 aluminium Inorganic materials 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 150000003377 silicon compounds Chemical class 0.000 claims description 5
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 claims description 4
- HSCLUIKEZDGKBP-UHFFFAOYSA-N 2,3-di(propan-2-yl)butanedioic acid Chemical compound CC(C)C(C(O)=O)C(C(C)C)C(O)=O HSCLUIKEZDGKBP-UHFFFAOYSA-N 0.000 claims description 4
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 claims description 4
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 150000002170 ethers Chemical class 0.000 claims description 4
- 125000005498 phthalate group Chemical group 0.000 claims description 4
- 150000003609 titanium compounds Chemical class 0.000 claims description 4
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 3
- 150000001721 carbon Chemical group 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 235000005985 organic acids Nutrition 0.000 claims description 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 150000007524 organic acids Chemical class 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
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims 3
- WNVMVIYFKFGESM-UHFFFAOYSA-N bis(2-methylpropyl) 2,3-di(propan-2-yl)butanedioate Chemical compound CC(C)COC(=O)C(C(C)C)C(C(C)C)C(=O)OCC(C)C WNVMVIYFKFGESM-UHFFFAOYSA-N 0.000 claims 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 1
- 150000005690 diesters Chemical class 0.000 claims 1
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 abstract 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 35
- 229920000642 polymer Polymers 0.000 description 33
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 26
- 150000003900 succinic acid esters Chemical class 0.000 description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 17
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000011777 magnesium Substances 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 9
- 239000007789 gas Substances 0.000 description 9
- 229920001155 polypropylene Polymers 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 235000011147 magnesium chloride Nutrition 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 238000011282 treatment Methods 0.000 description 8
- 229910003074 TiCl4 Inorganic materials 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 7
- 239000008096 xylene Substances 0.000 description 7
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- 239000004743 Polypropylene Substances 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- 229910001629 magnesium chloride Inorganic materials 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- 239000004711 α-olefin Substances 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000007334 copolymerization reaction Methods 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
- 229910000831 Steel Inorganic materials 0.000 description 4
- 238000013019 agitation Methods 0.000 description 4
- JWCYDYZLEAQGJJ-UHFFFAOYSA-N dicyclopentyl(dimethoxy)silane Chemical compound C1CCCC1[Si](OC)(OC)C1CCCC1 JWCYDYZLEAQGJJ-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 230000000694 effects Effects 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000010959 steel Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- WXUAQHNMJWJLTG-VKHMYHEASA-N (S)-methylsuccinic acid Chemical compound OC(=O)[C@@H](C)CC(O)=O WXUAQHNMJWJLTG-VKHMYHEASA-N 0.000 description 3
- VQNGKYXWYAHFPF-UHFFFAOYSA-N 2-cyclohexyl-3-cyclopentylbutanedioic acid Chemical compound C1CCCC1C(C(=O)O)C(C(O)=O)C1CCCCC1 VQNGKYXWYAHFPF-UHFFFAOYSA-N 0.000 description 3
- KDNUUZCIPIPBKN-UHFFFAOYSA-N 4-oxo-4-(1,1,1-trifluoropropan-2-yloxy)butanoic acid Chemical compound FC(F)(F)C(C)OC(=O)CCC(O)=O KDNUUZCIPIPBKN-UHFFFAOYSA-N 0.000 description 3
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 229940043279 diisopropylamine Drugs 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 239000010935 stainless steel Substances 0.000 description 3
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidine Chemical compound CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 2
- AJLCTEPRECBBKT-UHFFFAOYSA-N 2,3-bis(3-methylbutyl)butanedioic acid Chemical compound CC(C)CCC(C(O)=O)C(C(O)=O)CCC(C)C AJLCTEPRECBBKT-UHFFFAOYSA-N 0.000 description 2
- FUFSLRDLUNRCHM-UHFFFAOYSA-N 2,3-diethyl-2,3-di(propan-2-yl)butanedioic acid Chemical compound CCC(C(C)C)(C(O)=O)C(CC)(C(C)C)C(O)=O FUFSLRDLUNRCHM-UHFFFAOYSA-N 0.000 description 2
- BEHQZIRZSPNOIT-UHFFFAOYSA-N 2,3-diethyl-2-propan-2-ylbutanedioic acid Chemical compound CCC(C(O)=O)C(CC)(C(C)C)C(O)=O BEHQZIRZSPNOIT-UHFFFAOYSA-N 0.000 description 2
- AVIFPSNRFRVXMI-UHFFFAOYSA-N 2-benzyl-2-propan-2-ylbutanedioic acid Chemical compound OC(=O)CC(C(C)C)(C(O)=O)CC1=CC=CC=C1 AVIFPSNRFRVXMI-UHFFFAOYSA-N 0.000 description 2
- UFSJLOVZESXSHD-UHFFFAOYSA-N 2-butyl-2-phenylbutanedioic acid Chemical compound CCCCC(CC(O)=O)(C(O)=O)C1=CC=CC=C1 UFSJLOVZESXSHD-UHFFFAOYSA-N 0.000 description 2
- VZWZBFDXXQFDHW-UHFFFAOYSA-N 2-cyclohexyl-3-(3-methylbutyl)butanedioic acid Chemical compound CC(C)CCC(C(O)=O)C(C(O)=O)C1CCCCC1 VZWZBFDXXQFDHW-UHFFFAOYSA-N 0.000 description 2
- LIJMAHQYXMQISA-UHFFFAOYSA-N 2-cyclohexyl-3-propan-2-ylbutanedioic acid Chemical compound CC(C)C(C(O)=O)C(C(O)=O)C1CCCCC1 LIJMAHQYXMQISA-UHFFFAOYSA-N 0.000 description 2
- GIPUHGMDLPLFGZ-UHFFFAOYSA-N 2-cyclopentyl-2-propylbutanedioic acid Chemical compound CCCC(CC(O)=O)(C(O)=O)C1CCCC1 GIPUHGMDLPLFGZ-UHFFFAOYSA-N 0.000 description 2
- ZTPFWDMGYSWDAI-UHFFFAOYSA-N 2-methyl-2-propan-2-ylbutanedioic acid Chemical compound CC(C)C(C)(C(O)=O)CC(O)=O ZTPFWDMGYSWDAI-UHFFFAOYSA-N 0.000 description 2
- 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 2
- IFNUNBGGVMUJNV-UHFFFAOYSA-N 4-(1-cyclohexylethoxy)-4-oxobutanoic acid Chemical compound OC(=O)CCC(=O)OC(C)C1CCCCC1 IFNUNBGGVMUJNV-UHFFFAOYSA-N 0.000 description 2
- RQPUMSMXKHBGMO-UHFFFAOYSA-N 4-(9H-fluoren-9-yloxy)-4-oxobutanoic acid Chemical compound C1=CC=C2C(OC(=O)CCC(=O)O)C3=CC=CC=C3C2=C1 RQPUMSMXKHBGMO-UHFFFAOYSA-N 0.000 description 2
- HZXMLBSUEZTYHZ-UHFFFAOYSA-N 4-(cyclohexylmethoxy)-4-oxobutanoic acid Chemical compound OC(=O)CCC(=O)OCC1CCCCC1 HZXMLBSUEZTYHZ-UHFFFAOYSA-N 0.000 description 2
- CQBVVSONJDUVEJ-UHFFFAOYSA-N 4-cyclohexyloxy-4-oxobutanoic acid Chemical compound OC(=O)CCC(=O)OC1CCCCC1 CQBVVSONJDUVEJ-UHFFFAOYSA-N 0.000 description 2
- RQNNLQNFSREFER-UHFFFAOYSA-N CC(C)CC(C)OC(=O)CCC(=O)O Chemical compound CC(C)CC(C)OC(=O)CCC(=O)O RQNNLQNFSREFER-UHFFFAOYSA-N 0.000 description 2
- GFQUHXOKHFFPGI-UHFFFAOYSA-N CCC(CC)COC(=O)CCC(O)=O Chemical compound CCC(CC)COC(=O)CCC(O)=O GFQUHXOKHFFPGI-UHFFFAOYSA-N 0.000 description 2
- XHLXMRJWRKQMCP-UHFFFAOYSA-N Diethyl methylsuccinate Chemical compound CCOC(=O)CC(C)C(=O)OCC XHLXMRJWRKQMCP-UHFFFAOYSA-N 0.000 description 2
- 235000019502 Orange oil Nutrition 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000005234 alkyl aluminium group Chemical group 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- RREHKLQGUDYKJV-UHFFFAOYSA-N bis(2-methylpropyl) 2,2,3-trimethylbutanedioate Chemical compound CC(C)COC(=O)C(C)C(C)(C)C(=O)OCC(C)C RREHKLQGUDYKJV-UHFFFAOYSA-N 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 150000001934 cyclohexanes Chemical class 0.000 description 2
- SJJCABYOVIHNPZ-UHFFFAOYSA-N cyclohexyl-dimethoxy-methylsilane Chemical compound CO[Si](C)(OC)C1CCCCC1 SJJCABYOVIHNPZ-UHFFFAOYSA-N 0.000 description 2
- JVQDNCKPHSZFSO-UHFFFAOYSA-N diethyl 2-phenylbutanedioate Chemical compound CCOC(=O)CC(C(=O)OCC)C1=CC=CC=C1 JVQDNCKPHSZFSO-UHFFFAOYSA-N 0.000 description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 2
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 2
- 230000004907 flux Effects 0.000 description 2
- 230000004927 fusion Effects 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical class ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 229940078552 o-xylene Drugs 0.000 description 2
- 239000010502 orange oil Substances 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000012798 spherical particle Substances 0.000 description 2
- 235000011149 sulphuric acid Nutrition 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000003039 volatile agent Substances 0.000 description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- RIFKADJTWUGDOV-UHFFFAOYSA-N 1-cyclohexylethanone Chemical compound CC(=O)C1CCCCC1 RIFKADJTWUGDOV-UHFFFAOYSA-N 0.000 description 1
- CQCFISPMNREOQX-UHFFFAOYSA-N 2,2,3,3-tetraethylbutanedioic acid Chemical compound CCC(CC)(C(O)=O)C(CC)(CC)C(O)=O CQCFISPMNREOQX-UHFFFAOYSA-N 0.000 description 1
- XDMIOWTZXSLEKJ-UHFFFAOYSA-N 2,2,3,3-tetrapropylbutanedioic acid Chemical compound CCCC(CCC)(C(O)=O)C(CCC)(CCC)C(O)=O XDMIOWTZXSLEKJ-UHFFFAOYSA-N 0.000 description 1
- GOHPTLYPQCTZSE-UHFFFAOYSA-N 2,2-dimethylsuccinic acid Chemical compound OC(=O)C(C)(C)CC(O)=O GOHPTLYPQCTZSE-UHFFFAOYSA-N 0.000 description 1
- NVSRLSRGXUGMCX-UHFFFAOYSA-N 2,3-bis(2,2-dimethylpropyl)butanedioic acid Chemical compound CC(C)(C)CC(C(O)=O)C(C(O)=O)CC(C)(C)C NVSRLSRGXUGMCX-UHFFFAOYSA-N 0.000 description 1
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- RQPNECGZAMRIRP-UHFFFAOYSA-N diethyl 2-cyclohexylbutanedioate Chemical compound CCOC(=O)CC(C(=O)OCC)C1CCCCC1 RQPNECGZAMRIRP-UHFFFAOYSA-N 0.000 description 1
- XMVGCOWCTAZJNT-UHFFFAOYSA-N diethyl 2-cyclopropylbutanedioate Chemical compound CCOC(=O)CC(C(=O)OCC)C1CC1 XMVGCOWCTAZJNT-UHFFFAOYSA-N 0.000 description 1
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- JYEMURZLFONTNE-UHFFFAOYSA-N ethyl 1-(2-ethoxyacetyl)-2,6-dimethylcyclohexane-1-carboxylate Chemical compound CCOCC(=O)C1(C(=O)OCC)C(C)CCCC1C JYEMURZLFONTNE-UHFFFAOYSA-N 0.000 description 1
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- IIDVGIFOWJJSIJ-UHFFFAOYSA-M lithium;2-methylpropanoate Chemical compound [Li+].CC(C)C([O-])=O IIDVGIFOWJJSIJ-UHFFFAOYSA-M 0.000 description 1
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- 238000005259 measurement Methods 0.000 description 1
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- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 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
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- 239000011148 porous material Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
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- 239000012429 reaction media Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011833 salt mixture Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 239000011780 sodium chloride Substances 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
- 238000001228 spectrum Methods 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 238000012721 stereospecific polymerization Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 235000011044 succinic acid Nutrition 0.000 description 1
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- 229920001897 terpolymer Polymers 0.000 description 1
- 238000002076 thermal analysis method Methods 0.000 description 1
- ZWYDDDAMNQQZHD-UHFFFAOYSA-L titanium(ii) chloride Chemical compound [Cl-].[Cl-].[Ti+2] ZWYDDDAMNQQZHD-UHFFFAOYSA-L 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
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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
- C08F4/651—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
- 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
- C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F10/02—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
- 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
- C08F4/42—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
- C08F4/647—Catalysts containing a specific non-metal or metal-free compound
- C08F4/649—Catalysts containing a specific non-metal or metal-free compound organic
- C08F4/6494—Catalysts containing a specific non-metal or metal-free compound organic containing oxygen
-
- 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
- C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F210/16—Copolymers of ethene with alpha-alkenes, e.g. EP rubbers
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)
- Emergency Medicine (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP99201172 | 1999-04-15 | ||
| EP99201172 | 1999-04-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2269135T3 true ES2269135T3 (es) | 2007-04-01 |
Family
ID=8240100
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES00926912T Expired - Lifetime ES2269135T3 (es) | 1999-04-15 | 2000-04-12 | Componentes y catalizadores para la polimerizacion de olefinas. |
Country Status (22)
| Country | Link |
|---|---|
| US (2) | US6818583B1 (https=) |
| EP (1) | EP1088009B1 (https=) |
| JP (2) | JP4717219B2 (https=) |
| KR (1) | KR100700957B1 (https=) |
| CN (2) | CN1240729C (https=) |
| AR (1) | AR043275A1 (https=) |
| AT (1) | ATE335014T1 (https=) |
| AU (1) | AU777683B2 (https=) |
| BR (1) | BR0006095B1 (https=) |
| CA (1) | CA2334743C (https=) |
| DE (1) | DE60029714T2 (https=) |
| ES (1) | ES2269135T3 (https=) |
| HU (1) | HUP0103083A3 (https=) |
| ID (1) | ID28200A (https=) |
| IL (1) | IL140154A (https=) |
| MY (1) | MY124016A (https=) |
| NO (1) | NO20006388L (https=) |
| PL (1) | PL345209A1 (https=) |
| RU (1) | RU2225415C2 (https=) |
| SA (1) | SA00210385B1 (https=) |
| TW (1) | TWI229086B (https=) |
| WO (1) | WO2000063261A1 (https=) |
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2000
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- 2000-04-12 KR KR1020007014289A patent/KR100700957B1/ko not_active Expired - Lifetime
- 2000-04-12 AT AT00926912T patent/ATE335014T1/de active
- 2000-04-12 AU AU45486/00A patent/AU777683B2/en not_active Ceased
- 2000-04-12 DE DE60029714T patent/DE60029714T2/de not_active Expired - Lifetime
- 2000-04-12 IL IL140154A patent/IL140154A/en active IP Right Grant
- 2000-04-12 RU RU2001101489/04A patent/RU2225415C2/ru active
- 2000-04-12 CN CNB008011230A patent/CN1240729C/zh not_active Expired - Lifetime
- 2000-04-12 ES ES00926912T patent/ES2269135T3/es not_active Expired - Lifetime
- 2000-04-12 WO PCT/EP2000/003333 patent/WO2000063261A1/en not_active Ceased
- 2000-04-12 JP JP2000612346A patent/JP4717219B2/ja not_active Expired - Lifetime
- 2000-04-12 HU HU0103083A patent/HUP0103083A3/hu unknown
- 2000-04-12 EP EP00926912A patent/EP1088009B1/en not_active Expired - Lifetime
- 2000-04-12 BR BRPI0006095-0B1A patent/BR0006095B1/pt active IP Right Grant
- 2000-04-12 US US09/762,363 patent/US6818583B1/en not_active Expired - Lifetime
- 2000-04-12 CN CNB2003101242368A patent/CN1294159C/zh not_active Expired - Lifetime
- 2000-04-12 PL PL00345209A patent/PL345209A1/xx not_active IP Right Cessation
- 2000-04-12 ID IDW20010114A patent/ID28200A/id unknown
- 2000-04-13 TW TW089106866A patent/TWI229086B/zh not_active IP Right Cessation
- 2000-04-14 MY MYPI20001602A patent/MY124016A/en unknown
- 2000-04-17 AR ARP000101780A patent/AR043275A1/es active IP Right Grant
- 2000-09-24 SA SA00210385A patent/SA00210385B1/ar unknown
- 2000-12-14 NO NO20006388A patent/NO20006388L/no not_active Application Discontinuation
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2004
- 2004-08-31 US US10/930,452 patent/US20050032633A1/en not_active Abandoned
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- 2011-01-11 JP JP2011003209A patent/JP5372030B2/ja not_active Expired - Lifetime
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