CA1242550A - Catalyst for alpha-olefin polymerization - Google Patents
Catalyst for alpha-olefin polymerizationInfo
- Publication number
- CA1242550A CA1242550A CA000443255A CA443255A CA1242550A CA 1242550 A CA1242550 A CA 1242550A CA 000443255 A CA000443255 A CA 000443255A CA 443255 A CA443255 A CA 443255A CA 1242550 A CA1242550 A CA 1242550A
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- chlorine
- compound
- catalyst
- formula
- 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
Links
- 238000006116 polymerization reaction Methods 0.000 title claims abstract description 28
- 239000003054 catalyst Substances 0.000 title abstract description 65
- 239000004711 α-olefin Substances 0.000 title abstract description 12
- 150000001875 compounds Chemical class 0.000 claims abstract description 63
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 39
- 239000000460 chlorine Substances 0.000 claims abstract description 39
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 28
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 27
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 27
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 21
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 15
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 13
- 238000000034 method Methods 0.000 claims abstract description 12
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims abstract description 10
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims abstract description 9
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910052740 iodine Chemical group 0.000 claims abstract description 8
- 239000011630 iodine Chemical group 0.000 claims abstract description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 7
- 230000003197 catalytic effect Effects 0.000 claims abstract description 4
- 101100277337 Arabidopsis thaliana DDM1 gene Proteins 0.000 claims description 13
- 101150113676 chr1 gene Proteins 0.000 claims description 13
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 12
- 239000005977 Ethylene Chemical group 0.000 claims description 12
- -1 ethylene, ethylene Chemical group 0.000 claims description 12
- 239000000178 monomer Substances 0.000 claims description 9
- 150000001993 dienes Chemical class 0.000 claims description 8
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 230000000379 polymerizing effect Effects 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract description 18
- 239000001257 hydrogen Substances 0.000 abstract description 18
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 17
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract description 13
- 239000000203 mixture Substances 0.000 abstract description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 6
- 125000000041 C6-C10 aryl group Chemical group 0.000 abstract description 4
- 125000003342 alkenyl group Chemical group 0.000 abstract description 4
- 125000004093 cyano group Chemical group *C#N 0.000 abstract description 4
- 125000006575 electron-withdrawing group Chemical group 0.000 abstract description 4
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 2
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical group 0.000 abstract 1
- 235000013350 formula milk Nutrition 0.000 description 36
- 229940060038 chlorine Drugs 0.000 description 29
- 235000017168 chlorine Nutrition 0.000 description 29
- 229920000642 polymer Polymers 0.000 description 28
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 20
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 17
- 239000007789 gas Substances 0.000 description 15
- 239000012190 activator Substances 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 12
- 229920002943 EPDM rubber Polymers 0.000 description 11
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 11
- JBIQAPKSNFTACH-UHFFFAOYSA-K vanadium oxytrichloride Chemical compound Cl[V](Cl)(Cl)=O JBIQAPKSNFTACH-UHFFFAOYSA-K 0.000 description 11
- KPSSIOMAKSHJJG-UHFFFAOYSA-N neopentyl alcohol Chemical compound CC(C)(C)CO KPSSIOMAKSHJJG-UHFFFAOYSA-N 0.000 description 10
- LSGOVYNHVSXFFJ-UHFFFAOYSA-N vanadate(3-) Chemical compound [O-][V]([O-])([O-])=O LSGOVYNHVSXFFJ-UHFFFAOYSA-N 0.000 description 10
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 8
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 8
- 229910052720 vanadium Inorganic materials 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- OJOWICOBYCXEKR-APPZFPTMSA-N (1S,4R)-5-ethylidenebicyclo[2.2.1]hept-2-ene Chemical compound CC=C1C[C@@H]2C[C@@H]1C=C2 OJOWICOBYCXEKR-APPZFPTMSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- CMAOLVNGLTWICC-UHFFFAOYSA-N 2-fluoro-5-methylbenzonitrile Chemical compound CC1=CC=C(F)C(C#N)=C1 CMAOLVNGLTWICC-UHFFFAOYSA-N 0.000 description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 229960004592 isopropanol Drugs 0.000 description 4
- 229960005419 nitrogen Drugs 0.000 description 4
- IZIBACDHNNVHQA-UHFFFAOYSA-N ethyl 4,4,4-trichlorobut-2-enoate Chemical compound CCOC(=O)C=CC(Cl)(Cl)Cl IZIBACDHNNVHQA-UHFFFAOYSA-N 0.000 description 3
- SNFGYHXDYWUXIA-UHFFFAOYSA-N methyl 4,4,4-trichloro-2-methylbut-2-enoate Chemical compound COC(=O)C(C)=CC(Cl)(Cl)Cl SNFGYHXDYWUXIA-UHFFFAOYSA-N 0.000 description 3
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 238000004566 IR spectroscopy Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical group 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 235000011089 carbon dioxide Nutrition 0.000 description 2
- 239000003426 co-catalyst Substances 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000002685 polymerization catalyst Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- PRBHEGAFLDMLAL-GQCTYLIASA-N (4e)-hexa-1,4-diene Chemical compound C\C=C\CC=C PRBHEGAFLDMLAL-GQCTYLIASA-N 0.000 description 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- 101100448208 Human herpesvirus 6B (strain Z29) U69 gene Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910021552 Vanadium(IV) chloride Inorganic materials 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 229920005603 alternating copolymer Polymers 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 125000005140 aralkylsulfonyl group Chemical group 0.000 description 1
- 230000006583 body weight regulation Effects 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- AMRCYPCPQPCRDN-UHFFFAOYSA-N chloroperoxy hypochlorite vanadium Chemical compound O(OOCl)Cl.[V] AMRCYPCPQPCRDN-UHFFFAOYSA-N 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000003317 industrial substance Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- LMAZKPOSWVOFGY-FBAUPLQOSA-N orine Natural products CO[C@H]1C[C@H](O[C@H]2CC[C@]3(C)[C@H]4C[C@@H](OC(=O)C=Cc5ccccc5)[C@]6(C)[C@@](O)(CC[C@]6(O)[C@]4(O)CC=C3C2)[C@H](C)OC(=O)C=Cc7ccccc7)O[C@H](C)[C@H]1O LMAZKPOSWVOFGY-FBAUPLQOSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920013639 polyalphaolefin Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000004951 trihalomethoxy group Chemical group 0.000 description 1
- JTJFQBNJBPPZRI-UHFFFAOYSA-J vanadium tetrachloride Chemical group Cl[V](Cl)(Cl)Cl JTJFQBNJBPPZRI-UHFFFAOYSA-J 0.000 description 1
Landscapes
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US44936882A | 1982-12-14 | 1982-12-14 | |
| US44981182A | 1982-12-14 | 1982-12-14 | |
| US449,811 | 1982-12-14 | ||
| US449,368 | 1982-12-14 | ||
| US52802083A | 1983-08-31 | 1983-08-31 | |
| US52820283A | 1983-08-31 | 1983-08-31 | |
| US528,202 | 1983-08-31 | ||
| US528,020 | 1983-08-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1242550A true CA1242550A (en) | 1988-09-27 |
Family
ID=27503969
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000443255A Expired CA1242550A (en) | 1982-12-14 | 1983-12-14 | Catalyst for alpha-olefin polymerization |
| CA000443256A Expired CA1215073A (en) | 1982-12-14 | 1983-12-14 | CATALYST ACTIVATOR FOR .alpha. OLEFIN POLYMERIZATION |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000443256A Expired CA1215073A (en) | 1982-12-14 | 1983-12-14 | CATALYST ACTIVATOR FOR .alpha. OLEFIN POLYMERIZATION |
Country Status (4)
| Country | Link |
|---|---|
| AU (2) | AU573196B2 (cs) |
| BR (2) | BR8306822A (cs) |
| CA (2) | CA1242550A (cs) |
| IN (2) | IN160181B (cs) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2640978B1 (cs) * | 1988-12-22 | 1991-04-19 | Bp Chimie Sa | |
| US5786504A (en) * | 1996-05-15 | 1998-07-28 | Uniroyal Chemical Company, Inc. | Polymerization catalyst promoter |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU459046B2 (en) * | 1970-08-11 | 1975-03-13 | Ciba-Geigy Ag | Process forthe manufacture of tertiary butylates |
| US4189558A (en) * | 1977-02-14 | 1980-02-19 | Bayer Aktiengesellschaft | Process for the production of butadiene-propylene copolymers |
| DE2933885C3 (de) * | 1979-08-22 | 1982-05-06 | Chemische Werke Hüls AG, 4370 Marl | Verfahren zur Herstellung von Copolymeren des Ethylens mit mindestens einem anderen 1-Monoolefin und ggf. einem nicht-konjugierten Dien |
| AU1587683A (en) * | 1983-06-17 | 1984-12-20 | Merck & Co., Inc. | 2,3-dihalo-2,3-disubstituted propanoates |
-
1983
- 1983-12-05 IN IN818/DEL/83A patent/IN160181B/en unknown
- 1983-12-05 AU AU21990/83A patent/AU573196B2/en not_active Ceased
- 1983-12-05 IN IN819/DEL/83A patent/IN160356B/en unknown
- 1983-12-05 AU AU21989/83A patent/AU575547B2/en not_active Ceased
- 1983-12-12 BR BR8306822A patent/BR8306822A/pt unknown
- 1983-12-12 BR BR8306821A patent/BR8306821A/pt not_active IP Right Cessation
- 1983-12-14 CA CA000443255A patent/CA1242550A/en not_active Expired
- 1983-12-14 CA CA000443256A patent/CA1215073A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| AU575547B2 (en) | 1988-08-04 |
| IN160356B (cs) | 1987-07-11 |
| AU2199083A (en) | 1984-06-21 |
| AU2198983A (en) | 1984-06-21 |
| BR8306822A (pt) | 1984-11-13 |
| BR8306821A (pt) | 1984-11-13 |
| AU573196B2 (en) | 1988-06-02 |
| IN160181B (cs) | 1987-06-27 |
| CA1215073A (en) | 1986-12-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |