DE1104703B - Verfahren zur Herstellung von 1, 3-Butadienpolymeren - Google Patents
Verfahren zur Herstellung von 1, 3-ButadienpolymerenInfo
- Publication number
- DE1104703B DE1104703B DEM43454A DEM0043454A DE1104703B DE 1104703 B DE1104703 B DE 1104703B DE M43454 A DEM43454 A DE M43454A DE M0043454 A DEM0043454 A DE M0043454A DE 1104703 B DE1104703 B DE 1104703B
- Authority
- DE
- Germany
- Prior art keywords
- butadiene
- molecular weight
- polymer
- polymerization
- catalyst
- 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
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 title claims description 64
- 238000000034 method Methods 0.000 title claims description 16
- 229920002587 poly(1,3-butadiene) polymer Polymers 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 3
- 239000003054 catalyst Substances 0.000 claims description 36
- 238000006116 polymerization reaction Methods 0.000 claims description 23
- 150000001875 compounds Chemical class 0.000 claims description 12
- 229910052751 metal Inorganic materials 0.000 claims description 12
- 239000002184 metal Substances 0.000 claims description 12
- 150000002739 metals Chemical class 0.000 claims description 9
- HRGXHRPMGDCKQM-UHFFFAOYSA-L dichlorocobalt;pyridine Chemical compound Cl[Co]Cl.C1=CC=NC=C1 HRGXHRPMGDCKQM-UHFFFAOYSA-L 0.000 claims description 7
- -1 ethylene, propylene, propadiene Chemical class 0.000 claims description 7
- QNRMTGGDHLBXQZ-UHFFFAOYSA-N buta-1,2-diene Chemical compound CC=C=C QNRMTGGDHLBXQZ-UHFFFAOYSA-N 0.000 claims description 5
- 230000000737 periodic effect Effects 0.000 claims description 5
- 150000001993 dienes Chemical class 0.000 claims description 4
- 230000001105 regulatory effect Effects 0.000 claims description 4
- 239000004711 α-olefin Substances 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims 1
- IZMHKHHRLNWLMK-UHFFFAOYSA-M chloridoaluminium Chemical compound Cl[Al] IZMHKHHRLNWLMK-UHFFFAOYSA-M 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- 229920000642 polymer Polymers 0.000 description 44
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 41
- 239000000126 substance Substances 0.000 description 25
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 21
- 229920002857 polybutadiene Polymers 0.000 description 20
- 239000005977 Ethylene Substances 0.000 description 19
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 18
- 238000002474 experimental method Methods 0.000 description 15
- 239000005062 Polybutadiene Substances 0.000 description 12
- 230000000694 effects Effects 0.000 description 12
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 8
- 239000000178 monomer Substances 0.000 description 6
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 5
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 5
- 150000001336 alkenes Chemical class 0.000 description 4
- 150000001555 benzenes Chemical class 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001361 allenes Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 239000000110 cooling liquid Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 239000000806 elastomer Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 241001558496 Talpa caeca Species 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000005234 alkyl aluminium group Chemical group 0.000 description 1
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical compound C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- SSNYFFFCLVXSPK-UHFFFAOYSA-N buta-1,2-diene;buta-1,3-diene Chemical compound CC=C=C.C=CC=C SSNYFFFCLVXSPK-UHFFFAOYSA-N 0.000 description 1
- JPPGWVWBAJLHCE-UHFFFAOYSA-N buta-1,3-diene;ethene Chemical compound C=C.C=CC=C JPPGWVWBAJLHCE-UHFFFAOYSA-N 0.000 description 1
- 238000003490 calendering Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001869 cobalt compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 235000013601 eggs Nutrition 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 238000000752 ionisation method Methods 0.000 description 1
- 238000009533 lab test Methods 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 230000003340 mental effect Effects 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- LVMTVPFRTKXRPH-UHFFFAOYSA-N penta-1,2-diene Chemical compound CCC=C=C LVMTVPFRTKXRPH-UHFFFAOYSA-N 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000004260 weight control Methods 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
- C08F136/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F136/02—Homopolymers 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
- C08F136/04—Homopolymers 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
- C08F136/06—Butadiene
-
- 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
- C08F4/70—Iron group metals, platinum group metals or compounds thereof
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)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT1750058 | 1958-11-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1104703B true DE1104703B (de) | 1961-04-13 |
Family
ID=11150390
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEM43454A Pending DE1104703B (de) | 1958-11-26 | 1959-11-21 | Verfahren zur Herstellung von 1, 3-Butadienpolymeren |
Country Status (10)
| Country | Link |
|---|---|
| BE (1) | BE584997A (en, 2012) |
| CH (1) | CH393747A (en, 2012) |
| DE (1) | DE1104703B (en, 2012) |
| DK (1) | DK127601B (en, 2012) |
| ES (1) | ES253709A1 (en, 2012) |
| FR (1) | FR1241011A (en, 2012) |
| GB (1) | GB926036A (en, 2012) |
| LU (1) | LU37959A1 (en, 2012) |
| NL (2) | NL245747A (en, 2012) |
| SE (1) | SE218830C1 (en, 2012) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1135664B (de) * | 1960-06-07 | 1962-08-30 | Montedison Spa | Verfahren zur Polymerisation von Butadien zu cis-1, 4-Polybutadien mit mittlerem Molekulargewicht |
| DE1152823B (de) | 1958-12-08 | 1963-08-14 | Shell Int Research | Verfahren zur selektiven Polymerisation von Butadien zu cis-1,4-Polybutadien |
| US3220999A (en) * | 1961-03-13 | 1965-11-30 | Shell Oil Co | Process for polymerizing conjugated dienes |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1310146A (en, 2012) * | 1960-12-05 | 1963-03-06 | ||
| US3247175A (en) * | 1962-07-12 | 1966-04-19 | Copolymer Rubber & Chem Corp | Process for preparing high cis-1, 4-polybutadiene |
| US4224426A (en) | 1978-11-13 | 1980-09-23 | The B. F. Goodrich Company | Polymerization process for cis-1,4-polybutadiene using cycloalkane solvents and an aromatic polymerization regulator |
| US4983695A (en) * | 1982-04-26 | 1991-01-08 | The Goodyear Tire & Rubber Company | Molecular weight control of polybutadiene |
| CA1236648A (en) * | 1982-04-26 | 1988-05-10 | Ken W. Donbar | Controlling the molecular weight of polybutadiene |
| DE3538130A1 (de) * | 1985-10-26 | 1987-04-30 | Bunawerke Huels Gmbh | Verfahren und katalysator zur herstellung von syndiotaktischem 1,2-polybutadien |
| DE19806931A1 (de) * | 1998-02-19 | 1999-08-26 | Bayer Ag | Verfahren zur Herstellung von Polydienen mit geregelter Mooney-Viskosität |
| US20120296055A1 (en) | 2010-01-15 | 2012-11-22 | Reliance Industries Limited | High-cis polybutadiene rubber in benign solvents and process for preparation thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE543292A (en, 2012) * | 1954-12-02 |
-
0
- NL NL129664D patent/NL129664C/xx active
- NL NL245747D patent/NL245747A/xx unknown
- BE BE584997D patent/BE584997A/xx unknown
- LU LU37959D patent/LU37959A1/xx unknown
-
1959
- 1959-11-20 GB GB39486/59A patent/GB926036A/en not_active Expired
- 1959-11-21 DE DEM43454A patent/DE1104703B/de active Pending
- 1959-11-21 SE SE1095659A patent/SE218830C1/sl unknown
- 1959-11-23 FR FR810947A patent/FR1241011A/fr not_active Expired
- 1959-11-25 ES ES0253709A patent/ES253709A1/es not_active Expired
- 1959-11-25 CH CH8105659A patent/CH393747A/de unknown
- 1959-11-25 DK DK427459AA patent/DK127601B/da unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE543292A (en, 2012) * | 1954-12-02 |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1152823B (de) | 1958-12-08 | 1963-08-14 | Shell Int Research | Verfahren zur selektiven Polymerisation von Butadien zu cis-1,4-Polybutadien |
| DE1135664B (de) * | 1960-06-07 | 1962-08-30 | Montedison Spa | Verfahren zur Polymerisation von Butadien zu cis-1, 4-Polybutadien mit mittlerem Molekulargewicht |
| US3220999A (en) * | 1961-03-13 | 1965-11-30 | Shell Oil Co | Process for polymerizing conjugated dienes |
Also Published As
| Publication number | Publication date |
|---|---|
| CH393747A (de) | 1965-06-15 |
| SE218830C1 (en, 2012) | 1968-02-13 |
| NL129664C (en, 2012) | |
| BE584997A (en, 2012) | |
| ES253709A1 (es) | 1960-06-01 |
| NL245747A (en, 2012) | |
| DK127601B (da) | 1973-12-03 |
| FR1241011A (fr) | 1960-09-09 |
| LU37959A1 (en, 2012) | |
| GB926036A (en) | 1963-05-15 |
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