SA97180735B1 - cycloentadienyl 3-heteroatom ubsttutedيحتوي على معقدات فلزية وعملية بلمرة الأولفين ole fin polymeirization - Google Patents

Info

Publication number

SA97180735B1

SA97180735B1 SA97180735A SA97180735A SA97180735B1 SA 97180735 B1 SA97180735 B1 SA 97180735B1 SA 97180735 A SA97180735 A SA 97180735A SA 97180735 A SA97180735 A SA 97180735A SA 97180735 B1 SA97180735 B1 SA 97180735B1

Authority

SA

Saudi Arabia

Prior art keywords

dimethyl

titanium

dimethylethyl

pyrrolidinyl

inden

Prior art date

1996-08-08

Links

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• 238000006116 polymerization reaction Methods 0.000 title claims abstract description 88
• 229910052751 metal Inorganic materials 0.000 title claims abstract description 57
• 239000002184 metal Substances 0.000 title claims abstract description 57
• 150000001336 alkenes Chemical class 0.000 title claims abstract description 49
• JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 title claims abstract description 30
• 239000003054 catalyst Substances 0.000 claims abstract description 92
• 239000003446 ligand Substances 0.000 claims abstract description 59
• 239000010936 titanium Substances 0.000 claims description 378
• 229910052719 titanium Inorganic materials 0.000 claims description 368
• RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 322
• -1 phosphorus sulfur sulfur oxygen Chemical compound 0.000 claims description 307
• 150000001875 compounds Chemical class 0.000 claims description 98
• 125000001183 hydrocarbyl group Chemical group 0.000 claims description 94
• 125000004429 atom Chemical group 0.000 claims description 41
• UBHZUDXTHNMNLD-UHFFFAOYSA-N dimethylsilane Chemical compound C[SiH2]C UBHZUDXTHNMNLD-UHFFFAOYSA-N 0.000 claims description 37
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 36
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 30
• 230000003647 oxidation Effects 0.000 claims description 30
• 238000007254 oxidation reaction Methods 0.000 claims description 30
• 239000001257 hydrogen Substances 0.000 claims description 29
• 229910052739 hydrogen Inorganic materials 0.000 claims description 29
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 26
• 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
• 150000002736 metal compounds Chemical class 0.000 claims description 25
• 125000000217 alkyl group Chemical group 0.000 claims description 21
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
• 229910052757 nitrogen Inorganic materials 0.000 claims description 20
• 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 20
• 125000004122 cyclic group Chemical group 0.000 claims description 18
• 125000003118 aryl group Chemical group 0.000 claims description 16
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
• 150000004696 coordination complex Chemical class 0.000 claims description 15
• OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 15
• 125000004432 carbon atom Chemical group C* 0.000 claims description 14
• 125000000129 anionic group Chemical group 0.000 claims description 13
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 13
• 229910052760 oxygen Inorganic materials 0.000 claims description 13
• 230000007935 neutral effect Effects 0.000 claims description 12
• ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 10
• 229910052796 boron Inorganic materials 0.000 claims description 10
• 230000000737 periodic effect Effects 0.000 claims description 9
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 9
• 239000003426 co-catalyst Substances 0.000 claims description 8
• AHAREKHAZNPPMI-UHFFFAOYSA-N hexa-1,3-diene Chemical compound CCC=CC=C AHAREKHAZNPPMI-UHFFFAOYSA-N 0.000 claims description 8
• ZWYDDDAMNQQZHD-UHFFFAOYSA-L titanium(ii) chloride Chemical compound [Cl-].[Cl-].[Ti+2] ZWYDDDAMNQQZHD-UHFFFAOYSA-L 0.000 claims description 8
• 229910052799 carbon Inorganic materials 0.000 claims description 7
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 7
• PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 claims description 7
• 125000001424 substituent group Chemical group 0.000 claims description 7
• 239000002879 Lewis base Substances 0.000 claims description 6
• 150000007527 lewis bases Chemical class 0.000 claims description 6
• PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 claims description 5
• 239000001273 butane Substances 0.000 claims description 5
• 229910052726 zirconium Inorganic materials 0.000 claims description 5
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
• 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
• RYPKRALMXUUNKS-UHFFFAOYSA-N 2-Hexene Natural products CCCC=CC RYPKRALMXUUNKS-UHFFFAOYSA-N 0.000 claims description 3
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
• 125000005843 halogen group Chemical group 0.000 claims description 3
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
• FVZVCSNXTFCBQU-UHFFFAOYSA-N phosphanyl Chemical group [PH2] FVZVCSNXTFCBQU-UHFFFAOYSA-N 0.000 claims description 3
• 125000003386 piperidinyl group Chemical group 0.000 claims description 3
• 101150036449 SIRPA gene Proteins 0.000 claims description 2
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
• DPUXQWOMYBMHRN-UHFFFAOYSA-N hexa-2,3-diene Chemical compound CCC=C=CC DPUXQWOMYBMHRN-UHFFFAOYSA-N 0.000 claims description 2
• 125000002757 morpholinyl group Chemical group 0.000 claims description 2
• UZGLIIJVICEWHF-UHFFFAOYSA-N octogen Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)CN([N+]([O-])=O)C1 UZGLIIJVICEWHF-UHFFFAOYSA-N 0.000 claims description 2
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
• KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims 2
• 240000007681 Catha edulis Species 0.000 claims 2
• 235000006696 Catha edulis Nutrition 0.000 claims 2
• APPOKADJQUIAHP-GGWOSOGESA-N (2e,4e)-hexa-2,4-diene Chemical compound C\C=C\C=C\C APPOKADJQUIAHP-GGWOSOGESA-N 0.000 claims 1
• GUPMCMZMDAGSPF-UHFFFAOYSA-N 1-phenylbuta-1,3-dienylbenzene Chemical compound C=1C=CC=CC=1[C](C=C[CH2])C1=CC=CC=C1 GUPMCMZMDAGSPF-UHFFFAOYSA-N 0.000 claims 1
• 244000198134 Agave sisalana Species 0.000 claims 1
• 241000282326 Felis catus Species 0.000 claims 1
• 125000004915 dibutylamino group Chemical group C(CCC)N(CCCC)* 0.000 claims 1
• 229910052735 hafnium Inorganic materials 0.000 claims 1
• XTJLXXCARCJVPJ-UHFFFAOYSA-N hepta-2,4-diene Chemical compound CCC=CC=CC XTJLXXCARCJVPJ-UHFFFAOYSA-N 0.000 claims 1
• 150000004687 hexahydrates Chemical class 0.000 claims 1
• 150000002431 hydrogen Chemical class 0.000 claims 1
• 125000005394 methallyl group Chemical group 0.000 claims 1
• 125000000168 pyrrolyl group Chemical group 0.000 claims 1
• CMWCOKOTCLFJOP-UHFFFAOYSA-N titanium(3+) Chemical compound [Ti+3] CMWCOKOTCLFJOP-UHFFFAOYSA-N 0.000 claims 1
• JFLKFZNIIQFQBS-FNCQTZNRSA-N trans,trans-1,4-Diphenyl-1,3-butadiene Chemical group C=1C=CC=CC=1\C=C\C=C\C1=CC=CC=C1 JFLKFZNIIQFQBS-FNCQTZNRSA-N 0.000 claims 1
• VPGLGRNSAYHXPY-UHFFFAOYSA-L zirconium(2+);dichloride Chemical compound Cl[Zr]Cl VPGLGRNSAYHXPY-UHFFFAOYSA-L 0.000 claims 1
• 229920000642 polymer Polymers 0.000 abstract description 59
• 125000000058 cyclopentadienyl group Chemical class C1(=CC=CC1)* 0.000 abstract description 16
• ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 abstract description 16
• 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 abstract description 16
• 230000003197 catalytic effect Effects 0.000 abstract description 14
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 411
• 239000000243 solution Substances 0.000 description 165
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 115
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 110
• 239000000203 mixture Substances 0.000 description 88
• 238000002360 preparation method Methods 0.000 description 84
• 239000002904 solvent Substances 0.000 description 82
• 239000000047 product Substances 0.000 description 81
• 238000000034 method Methods 0.000 description 80
• 230000002829 reductive effect Effects 0.000 description 73
• 239000007787 solid Substances 0.000 description 69
• 239000000178 monomer Substances 0.000 description 67
• 238000006243 chemical reaction Methods 0.000 description 59
• 238000003756 stirring Methods 0.000 description 48
• 239000013078 crystal Substances 0.000 description 46
• VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 45
• 229910052744 lithium Inorganic materials 0.000 description 44
• 239000005977 Ethylene Substances 0.000 description 43
• WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 43
• 230000008569 process Effects 0.000 description 42
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 40
• 239000002244 precipitate Substances 0.000 description 38
• 150000001993 dienes Chemical class 0.000 description 35
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 32
• 238000007792 addition Methods 0.000 description 31
• 238000001914 filtration Methods 0.000 description 31
• 125000003963 dichloro group Chemical group Cl* 0.000 description 29
• 229910052782 aluminium Inorganic materials 0.000 description 28
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• 239000003921 oil Substances 0.000 description 27
• 235000019198 oils Nutrition 0.000 description 27
• 239000007788 liquid Substances 0.000 description 25
• DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 25
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• 239000012071 phase Substances 0.000 description 24
• 239000000126 substance Substances 0.000 description 24
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 23
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• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 22
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• 239000003795 chemical substances by application Substances 0.000 description 21
• 229910000077 silane Inorganic materials 0.000 description 21
• 229910003002 lithium salt Inorganic materials 0.000 description 20
• 159000000002 lithium salts Chemical class 0.000 description 20
• 150000003839 salts Chemical class 0.000 description 20
• 150000001412 amines Chemical class 0.000 description 19
• BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 18
• 238000012937 correction Methods 0.000 description 18
• 229920002943 EPDM rubber Polymers 0.000 description 16
• 150000001768 cations Chemical class 0.000 description 16
• 239000000706 filtrate Substances 0.000 description 16
• 239000011777 magnesium Substances 0.000 description 16
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 16
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• 230000006870 function Effects 0.000 description 11
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