DE2257137C2 - Verfahren zur Herstellung Polybutadiens mit einem hohen Gehalt der Butadieneinheiten in cis-1,4-Struktur - Google Patents
Verfahren zur Herstellung Polybutadiens mit einem hohen Gehalt der Butadieneinheiten in cis-1,4-StrukturInfo
- Publication number
- DE2257137C2 DE2257137C2 DE2257137A DE2257137A DE2257137C2 DE 2257137 C2 DE2257137 C2 DE 2257137C2 DE 2257137 A DE2257137 A DE 2257137A DE 2257137 A DE2257137 A DE 2257137A DE 2257137 C2 DE2257137 C2 DE 2257137C2
- Authority
- DE
- Germany
- Prior art keywords
- hydrogen fluoride
- complex
- nickel
- catalyst
- polymerization
- 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
- KAKZBPTYRLMSJV-UHFFFAOYSA-N butadiene group Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 title claims description 30
- 238000000034 method Methods 0.000 title claims description 27
- 229920002857 polybutadiene Polymers 0.000 title claims description 9
- 239000005062 Polybutadiene Substances 0.000 title claims description 5
- 239000003054 catalyst Substances 0.000 claims description 47
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 19
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 19
- 239000002904 solvent Substances 0.000 claims description 19
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims description 17
- 238000006116 polymerization reaction Methods 0.000 claims description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 11
- 150000001993 dienes Chemical class 0.000 claims description 10
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 8
- 229910052782 aluminium Inorganic materials 0.000 claims description 8
- 229910052759 nickel Inorganic materials 0.000 claims description 8
- 150000002816 nickel compounds Chemical class 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 3
- OTUKPXUUYJTFFJ-UHFFFAOYSA-N F.CC(C)=O Chemical compound F.CC(C)=O OTUKPXUUYJTFFJ-UHFFFAOYSA-N 0.000 claims description 2
- HAVUZBHAXICAID-UHFFFAOYSA-N benzonitrile;hydrofluoride Chemical compound [H+].[F-].N#CC1=CC=CC=C1 HAVUZBHAXICAID-UHFFFAOYSA-N 0.000 claims description 2
- 150000001735 carboxylic acids Chemical class 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 150000002815 nickel Chemical class 0.000 claims description 2
- USIPDEFCQIYKCX-UHFFFAOYSA-N oxolane;hydrofluoride Chemical compound F.C1CCOC1 USIPDEFCQIYKCX-UHFFFAOYSA-N 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 239000000178 monomer Substances 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical group CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 239000008139 complexing agent Substances 0.000 description 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 3
- 125000005234 alkyl aluminium group Chemical group 0.000 description 3
- -1 fluorine compound benzotrifluoride Chemical class 0.000 description 3
- DVTHIMLUHWEZOM-UHFFFAOYSA-L nickel(2+);octanoate Chemical compound [Ni+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O DVTHIMLUHWEZOM-UHFFFAOYSA-L 0.000 description 3
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 3
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RBOZTFPIXJBLPK-WGDLNXRISA-N (NZ)-N-[(2Z)-1,2-bis(furan-2-yl)-2-hydroxyiminoethylidene]hydroxylamine Chemical compound O\N=C(\C(=N\O)\c1ccco1)/c1ccco1 RBOZTFPIXJBLPK-WGDLNXRISA-N 0.000 description 1
- UVPKUTPZWFHAHY-UHFFFAOYSA-L 2-ethylhexanoate;nickel(2+) Chemical compound [Ni+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O UVPKUTPZWFHAHY-UHFFFAOYSA-L 0.000 description 1
- YACTXGRTJNKUDC-UHFFFAOYSA-N 2-hydroxybenzaldehyde;nickel Chemical compound [Ni].OC1=CC=CC=C1C=O.OC1=CC=CC=C1C=O YACTXGRTJNKUDC-UHFFFAOYSA-N 0.000 description 1
- FUDNBFMOXDUIIE-UHFFFAOYSA-N 3,7-dimethylocta-1,6-diene Chemical compound C=CC(C)CCC=C(C)C FUDNBFMOXDUIIE-UHFFFAOYSA-N 0.000 description 1
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical compound CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 description 1
- MQRWBMAEBQOWAF-UHFFFAOYSA-N acetic acid;nickel Chemical compound [Ni].CC(O)=O.CC(O)=O MQRWBMAEBQOWAF-UHFFFAOYSA-N 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- HECLRDQVFMWTQS-HORUIINNSA-N bis[cyclopentadiene] Chemical compound C1C2[C@H]3CC=C[C@H]3C1C=C2 HECLRDQVFMWTQS-HORUIINNSA-N 0.000 description 1
- 238000012662 bulk polymerization Methods 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- LXHKZDOLHOQBTR-UHFFFAOYSA-L hexadecanoate;nickel(2+) Chemical compound [Ni+2].CCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCC([O-])=O LXHKZDOLHOQBTR-UHFFFAOYSA-L 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- UIEKYBOPAVTZKW-UHFFFAOYSA-L naphthalene-2-carboxylate;nickel(2+) Chemical compound [Ni+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 UIEKYBOPAVTZKW-UHFFFAOYSA-L 0.000 description 1
- 229940078494 nickel acetate Drugs 0.000 description 1
- BMGNSKKZFQMGDH-FDGPNNRMSA-L nickel(2+);(z)-4-oxopent-2-en-2-olate Chemical compound [Ni+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O BMGNSKKZFQMGDH-FDGPNNRMSA-L 0.000 description 1
- GAIQJSWQJOZOMI-UHFFFAOYSA-L nickel(2+);dibenzoate Chemical compound [Ni+2].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 GAIQJSWQJOZOMI-UHFFFAOYSA-L 0.000 description 1
- JMWUYEFBFUCSAK-UHFFFAOYSA-L nickel(2+);octadecanoate Chemical compound [Ni+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O JMWUYEFBFUCSAK-UHFFFAOYSA-L 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000037048 polymerization activity Effects 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- SQBBHCOIQXKPHL-UHFFFAOYSA-N tributylalumane Chemical compound CCCC[Al](CCCC)CCCC SQBBHCOIQXKPHL-UHFFFAOYSA-N 0.000 description 1
- ORYGRKHDLWYTKX-UHFFFAOYSA-N trihexylalumane Chemical compound CCCCCC[Al](CCCCCC)CCCCCC ORYGRKHDLWYTKX-UHFFFAOYSA-N 0.000 description 1
- LFXVBWRMVZPLFK-UHFFFAOYSA-N trioctylalumane Chemical compound CCCCCCCC[Al](CCCCCCCC)CCCCCCCC LFXVBWRMVZPLFK-UHFFFAOYSA-N 0.000 description 1
- JOJQVUCWSDRWJE-UHFFFAOYSA-N tripentylalumane Chemical compound CCCCC[Al](CCCCC)CCCCC JOJQVUCWSDRWJE-UHFFFAOYSA-N 0.000 description 1
- CNWZYDSEVLFSMS-UHFFFAOYSA-N tripropylalumane Chemical compound CCC[Al](CCC)CCC CNWZYDSEVLFSMS-UHFFFAOYSA-N 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 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
- C08F36/06—Butadiene
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US20202471A | 1971-11-24 | 1971-11-24 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2257137A1 DE2257137A1 (de) | 1973-05-30 |
| DE2257137C2 true DE2257137C2 (de) | 1987-05-07 |
Family
ID=22748249
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2257137A Expired DE2257137C2 (de) | 1971-11-24 | 1972-11-17 | Verfahren zur Herstellung Polybutadiens mit einem hohen Gehalt der Butadieneinheiten in cis-1,4-Struktur |
Country Status (12)
| Country | Link |
|---|---|
| JP (1) | JPS5610321B2 (enExample) |
| AU (1) | AU465652B2 (enExample) |
| BE (1) | BE791768A (enExample) |
| BR (1) | BR7208163D0 (enExample) |
| CA (1) | CA977498A (enExample) |
| DD (1) | DD100270A5 (enExample) |
| DE (1) | DE2257137C2 (enExample) |
| FR (1) | FR2162961A5 (enExample) |
| GB (1) | GB1376027A (enExample) |
| IT (1) | IT973674B (enExample) |
| NL (1) | NL176081C (enExample) |
| ZA (1) | ZA727547B (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8372925B2 (en) * | 2007-04-10 | 2013-02-12 | Bridgestone Corporation | Nickel-based catalyst composition |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1142178A (en) * | 1967-02-23 | 1969-02-05 | Goodyear Tire & Rubber | Polymerization catalyst for dienes |
| US3483177A (en) * | 1967-12-15 | 1969-12-09 | Goodyear Tire & Rubber | Method for the polymerization of butadiene and butadiene in mixture with other diolefins using (1) organometallics,(2) organic ni or co,and (3) bf3 complexed with aldehydes,ketones,esters and nitriles |
| FR2047846A5 (enExample) * | 1969-05-19 | 1971-03-12 | Sumitomo Chemical Co |
-
0
- BE BE791768D patent/BE791768A/xx not_active IP Right Cessation
-
1972
- 1972-10-23 CA CA154,612A patent/CA977498A/en not_active Expired
- 1972-10-24 GB GB4895472A patent/GB1376027A/en not_active Expired
- 1972-10-24 ZA ZA727547A patent/ZA727547B/xx unknown
- 1972-10-26 AU AU48207/72A patent/AU465652B2/en not_active Expired
- 1972-11-17 DE DE2257137A patent/DE2257137C2/de not_active Expired
- 1972-11-21 JP JP11707272A patent/JPS5610321B2/ja not_active Expired
- 1972-11-21 FR FR7241245A patent/FR2162961A5/fr not_active Expired
- 1972-11-21 BR BR008163/72A patent/BR7208163D0/pt unknown
- 1972-11-22 DD DD167132A patent/DD100270A5/xx unknown
- 1972-11-22 IT IT54197/72A patent/IT973674B/it active
- 1972-11-23 NL NLAANVRAGE7215893,A patent/NL176081C/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JPS4864180A (enExample) | 1973-09-05 |
| JPS5610321B2 (enExample) | 1981-03-07 |
| FR2162961A5 (enExample) | 1973-07-20 |
| BR7208163D0 (pt) | 1973-08-23 |
| DE2257137A1 (de) | 1973-05-30 |
| AU465652B2 (en) | 1975-10-02 |
| AU4820772A (en) | 1974-05-02 |
| BE791768A (fr) | 1973-03-16 |
| IT973674B (it) | 1974-06-10 |
| GB1376027A (en) | 1974-12-04 |
| NL176081C (nl) | 1985-02-18 |
| DD100270A5 (enExample) | 1973-09-12 |
| CA977498A (en) | 1975-11-04 |
| ZA727547B (en) | 1973-07-25 |
| NL7215893A (enExample) | 1973-05-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0007027B1 (de) | Lösungspolymerisation von konjugierten Dienen | |
| EP0011184B1 (de) | Katalysator, dessen Herstellung und Verwendung zur Lösungspolymerisation von konjugierten Dienen | |
| DE69408265T2 (de) | Verfahren zur Herstellung von Polybutadien mit hochaktiven Katalysatoren | |
| DE1213120B (de) | Verfahren zur Polymerisation von Butadien | |
| DE1223559B (de) | Verfahren zur Herstellung von cis-1, 4-Polyisopren | |
| DE1809495A1 (de) | Verfahren zum Polymerisieren von Butadien | |
| DE2704763C2 (enExample) | ||
| DE2936653C2 (de) | Verfahren zur Polymerisation von 1,3-Butadien bzw. zu dessen Copolymerisation mit Isopren und/oder Styrol | |
| DE2360152A1 (de) | Verfahren zur herstellung eines ticl tief 3-katalysators fuer die herstellung von polyisopren | |
| DE1770587A1 (de) | Verfahren zum Herstellen von Polybutadien | |
| DE2615953C2 (de) | Verfahren zur Herstellung von festem kautschukartigem Polybutadien mit einem hohen Gehalt von mehr als 95 % der Butadieneinheiten in cis-1,4-Konfiguration | |
| DE1620927C3 (de) | Verfahren zur Herstellung von cis-1,4-Polybutadien | |
| DE69706620T2 (de) | Kobalt enthaltender Katalysator | |
| DE2053484A1 (de) | Verfahren zur Herstellung von flussi gem Polybutadien | |
| DE2619488A1 (de) | Verfahren zur polymerisation von butadien | |
| DE1809854A1 (de) | Verfahren zum Polymerisieren von Butadien und Butadien im Gemisch mit weiteren konjugierten Diolefinen | |
| DE2257137C2 (de) | Verfahren zur Herstellung Polybutadiens mit einem hohen Gehalt der Butadieneinheiten in cis-1,4-Struktur | |
| DE2945514C2 (de) | Verfahren zur Polymerisation von Butadien-1,3 | |
| DE2441015A1 (de) | Katalysatorsysteme fuer die polymerisation von konjugierten diolefinen | |
| DE2933609A1 (de) | Verfahren zur herstellung von 1.2-polybutadienen | |
| DE1620931A1 (de) | Verfahren zur Polymerisation und Mischpolymerisation konjugierter Diene | |
| DE2224388C3 (de) | Verfahren zur Herstellung von trans- 1,4-Polyisopren oder trans- 1,4-Polybutadien | |
| DD265150A1 (de) | Verfahren zur herstellung von polybutadien mit hohem 1,4-cis-gehalt | |
| DE2113527A1 (de) | Katalysatorsystem zum Polymerisieren konjugierter Diolefine | |
| DE2911307A1 (de) | Verfahren zur copolymerisation von cis-1,3-pentadien und trans-1,3-piperylen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| 8128 | New person/name/address of the agent |
Representative=s name: DEUFEL, P., DIPL.-CHEM.DIPL.-WIRTSCH.-ING.DR.RER.N |
|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition |