DE2265067A1 - Verfahren zur polymerisation von monoolefinen - Google Patents
Verfahren zur polymerisation von monoolefinenInfo
- Publication number
- DE2265067A1 DE2265067A1 DE19722265067 DE2265067A DE2265067A1 DE 2265067 A1 DE2265067 A1 DE 2265067A1 DE 19722265067 DE19722265067 DE 19722265067 DE 2265067 A DE2265067 A DE 2265067A DE 2265067 A1 DE2265067 A1 DE 2265067A1
- Authority
- DE
- Germany
- Prior art keywords
- polymerization
- catalyst
- carried out
- uranium
- polymerization reaction
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 35
- 238000006116 polymerization reaction Methods 0.000 title claims description 28
- 239000003054 catalyst Substances 0.000 claims description 27
- 239000000178 monomer Substances 0.000 claims description 18
- -1 alkyl radicals Chemical class 0.000 claims description 11
- 239000002841 Lewis acid Substances 0.000 claims description 10
- 150000007517 lewis acids Chemical class 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 7
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 6
- 239000005977 Ethylene Substances 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- 229910052770 Uranium Inorganic materials 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 150000001336 alkenes Chemical class 0.000 claims description 2
- 150000001450 anions Chemical group 0.000 claims description 2
- 150000005840 aryl radicals Chemical class 0.000 claims description 2
- 150000002170 ethers Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 150000005673 monoalkenes Chemical class 0.000 claims description 2
- 150000003003 phosphines Chemical class 0.000 claims description 2
- 150000003512 tertiary amines Chemical class 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 150000008282 halocarbons Chemical class 0.000 claims 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims 1
- 229930195734 saturated hydrocarbon Natural products 0.000 claims 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 40
- 229920000642 polymer Polymers 0.000 description 36
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 23
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 22
- 239000000203 mixture Substances 0.000 description 18
- 238000004458 analytical method Methods 0.000 description 14
- 239000007787 solid Substances 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 229920001971 elastomer Polymers 0.000 description 11
- 239000000806 elastomer Substances 0.000 description 11
- 238000012360 testing method Methods 0.000 description 10
- 229920002857 polybutadiene Polymers 0.000 description 9
- 150000003671 uranium compounds Chemical class 0.000 description 7
- 150000001993 dienes Chemical class 0.000 description 6
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 5
- 239000005062 Polybutadiene Substances 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 125000005234 alkyl aluminium group Chemical group 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- VLLYOYVKQDKAHN-UHFFFAOYSA-N buta-1,3-diene;2-methylbuta-1,3-diene Chemical compound C=CC=C.CC(=C)C=C VLLYOYVKQDKAHN-UHFFFAOYSA-N 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000012552 review Methods 0.000 description 2
- 230000000707 stereoselective effect Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000004073 vulcanization Methods 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
- WZFUQSJFWNHZHM-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 WZFUQSJFWNHZHM-UHFFFAOYSA-N 0.000 description 1
- LGLDSEPDYUTBNZ-UHFFFAOYSA-N 3-phenylbuta-1,3-dien-2-ylbenzene Chemical compound C=1C=CC=CC=1C(=C)C(=C)C1=CC=CC=C1 LGLDSEPDYUTBNZ-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 229920004939 Cariflex™ Polymers 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229920013645 Europrene Polymers 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 229920000459 Nitrile rubber Polymers 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- GEOVCVGUDGBSRC-UHFFFAOYSA-N [U].CCCCCC Chemical compound [U].CCCCCC GEOVCVGUDGBSRC-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000010692 aromatic oil Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- OZNCPAQBJMPCIO-UHFFFAOYSA-N buta-1,3-diene;penta-1,3-diene Chemical compound C=CC=C.CC=CC=C OZNCPAQBJMPCIO-UHFFFAOYSA-N 0.000 description 1
- XZKRXPZXQLARHH-UHFFFAOYSA-N buta-1,3-dienylbenzene Chemical compound C=CC=CC1=CC=CC=C1 XZKRXPZXQLARHH-UHFFFAOYSA-N 0.000 description 1
- 238000003490 calendering Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 230000035622 drinking Effects 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- HYIMSNHJOBLJNT-UHFFFAOYSA-N nifedipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1[N+]([O-])=O HYIMSNHJOBLJNT-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 229920001083 polybutene Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000004071 soot Substances 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- JCMLRUNDSXARRW-UHFFFAOYSA-N trioxouranium Chemical compound O=[U](=O)=O JCMLRUNDSXARRW-UHFFFAOYSA-N 0.000 description 1
- JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C08F36/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F36/02—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F36/04—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Polymerization Catalysts (AREA)
- Polymerisation Methods In General (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT31730/71A IT946105B (it) | 1971-11-26 | 1971-11-26 | Procedimento per la polimerizzazio ne stereospecifica delle diolefine e prodotti con esso ottenuti |
| IT3028972A IT1019535B (it) | 1972-10-10 | 1972-10-10 | Procedimento per la polimerizzazio ne delle olefine e prodtti con esso ottenuti |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2265067A1 true DE2265067A1 (de) | 1976-02-19 |
Family
ID=26328874
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722265067 Pending DE2265067A1 (de) | 1971-11-26 | 1972-11-24 | Verfahren zur polymerisation von monoolefinen |
| DE2257786A Expired DE2257786C2 (de) | 1971-11-26 | 1972-11-24 | Verfahren zur Homopolymerisation von Butadien-(1,3), Isopren oder Pentadien-(1,3) und zur Mischpolymerisation von Butadien-(1,3) mit Isopren oder Pentadien-(1,3) bzw. von Butadien-(1,3) oder Isopren mit Äthylen |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2257786A Expired DE2257786C2 (de) | 1971-11-26 | 1972-11-24 | Verfahren zur Homopolymerisation von Butadien-(1,3), Isopren oder Pentadien-(1,3) und zur Mischpolymerisation von Butadien-(1,3) mit Isopren oder Pentadien-(1,3) bzw. von Butadien-(1,3) oder Isopren mit Äthylen |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US3937692A (enExample) |
| JP (1) | JPS521756B2 (enExample) |
| AT (1) | AT320963B (enExample) |
| AU (1) | AU473541B2 (enExample) |
| BE (1) | BE791709A (enExample) |
| CA (1) | CA987441A (enExample) |
| CH (1) | CH565206A5 (enExample) |
| DE (2) | DE2265067A1 (enExample) |
| FR (1) | FR2162992A5 (enExample) |
| GB (1) | GB1406461A (enExample) |
| LU (1) | LU66529A1 (enExample) |
| NL (1) | NL166033C (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19512116A1 (de) * | 1995-04-04 | 1996-10-10 | Bayer Ag | Gasphasenpolymerisation von konjugierten Dienen in Gegenwart von Allylverbindungen der seltenen Erden |
| US8598286B1 (en) | 2012-11-05 | 2013-12-03 | The Goodyear Tire & Rubber Company | High cis diene/phenylbutadiene copolymers prepared using a Ziegler/Natta neodymium catalyst |
| CN110230104A (zh) * | 2019-07-08 | 2019-09-13 | 江苏海阳化纤有限公司 | 一种抗uv尼龙6用高强丝及其制备方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1213146A (fr) * | 1958-11-04 | 1960-03-29 | Bataafsche Petroleum | Procédé de polymérisation des diènes et catalyseurs convenant à cet effet |
| GB906334A (en) * | 1959-12-31 | 1962-09-19 | Bridgestone Tire Co Ltd | Method of manufacturing cis-1,4-polybutadiene |
| NL126767C (enExample) * | 1960-06-24 | |||
| DE1520964C3 (de) * | 1963-08-10 | 1975-03-13 | Studiengesellschaft Kohle Mbh, 4330 Muelheim | Verfahren zur Oligomerisation von Olefinen |
| NL126577C (enExample) * | 1963-08-10 | 1900-01-01 | ||
| US3468866A (en) * | 1966-06-06 | 1969-09-23 | Alexandr Vasilievich Alferov | Process for polymerizing butadiene in the presence of reaction products of pi-allylic complexes of transition metal and organic electron acceptors |
| FR1583616A (enExample) * | 1967-08-23 | 1969-11-21 |
-
0
- BE BE791709D patent/BE791709A/xx unknown
-
1972
- 1972-11-09 AU AU48666/72A patent/AU473541B2/en not_active Expired
- 1972-11-17 US US05/307,373 patent/US3937692A/en not_active Expired - Lifetime
- 1972-11-21 GB GB5381572A patent/GB1406461A/en not_active Expired
- 1972-11-22 FR FR7241405A patent/FR2162992A5/fr not_active Expired
- 1972-11-24 DE DE19722265067 patent/DE2265067A1/de active Pending
- 1972-11-24 CA CA157,499A patent/CA987441A/en not_active Expired
- 1972-11-24 DE DE2257786A patent/DE2257786C2/de not_active Expired
- 1972-11-24 LU LU66529A patent/LU66529A1/xx unknown
- 1972-11-25 CH CH1719672A patent/CH565206A5/xx not_active IP Right Cessation
- 1972-11-27 AT AT1008072A patent/AT320963B/de not_active IP Right Cessation
- 1972-11-27 NL NL7216036.A patent/NL166033C/xx not_active IP Right Cessation
- 1972-11-27 JP JP47118135A patent/JPS521756B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB1406461A (en) | 1975-09-17 |
| NL7216036A (enExample) | 1973-05-29 |
| DE2257786C2 (de) | 1983-05-05 |
| FR2162992A5 (enExample) | 1973-07-20 |
| NL166033B (nl) | 1981-01-15 |
| CH565206A5 (enExample) | 1975-08-15 |
| JPS4864177A (enExample) | 1973-09-05 |
| LU66529A1 (enExample) | 1973-02-01 |
| DE2257786A1 (de) | 1973-05-30 |
| AT320963B (de) | 1975-03-10 |
| NL166033C (nl) | 1981-06-15 |
| AU4866672A (en) | 1974-05-09 |
| JPS521756B2 (enExample) | 1977-01-18 |
| BE791709A (fr) | 1973-03-16 |
| US3937692A (en) | 1976-02-10 |
| CA987441A (en) | 1976-04-13 |
| AU473541B2 (en) | 1976-06-24 |
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