DE2014394A1 - Verfahren zur Polymerisation von Vinylidenkohlenwasserstoffen, gegebenenfalls im Gemisch mit anderen Olefinen - Google Patents
Verfahren zur Polymerisation von Vinylidenkohlenwasserstoffen, gegebenenfalls im Gemisch mit anderen OlefinenInfo
- Publication number
- DE2014394A1 DE2014394A1 DE19702014394 DE2014394A DE2014394A1 DE 2014394 A1 DE2014394 A1 DE 2014394A1 DE 19702014394 DE19702014394 DE 19702014394 DE 2014394 A DE2014394 A DE 2014394A DE 2014394 A1 DE2014394 A1 DE 2014394A1
- Authority
- DE
- Germany
- Prior art keywords
- vanadium
- polymerization
- olefins
- mixture
- optionally
- 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
- -1 vinylidene hydrocarbons Chemical class 0.000 title claims description 24
- 238000000034 method Methods 0.000 title claims description 18
- 238000006116 polymerization reaction Methods 0.000 title claims description 16
- 239000000203 mixture Substances 0.000 title claims description 15
- 150000001336 alkenes Chemical class 0.000 title claims description 10
- 229930195733 hydrocarbon Natural products 0.000 title claims description 8
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 35
- 239000003054 catalyst Substances 0.000 claims description 16
- 229910052720 vanadium Inorganic materials 0.000 claims description 15
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 claims description 6
- 229910021552 Vanadium(IV) chloride Inorganic materials 0.000 claims description 5
- JTJFQBNJBPPZRI-UHFFFAOYSA-J vanadium tetrachloride Chemical compound Cl[V](Cl)(Cl)Cl JTJFQBNJBPPZRI-UHFFFAOYSA-J 0.000 claims description 5
- CMAOLVNGLTWICC-UHFFFAOYSA-N 2-fluoro-5-methylbenzonitrile Chemical compound CC1=CC=C(F)C(C#N)=C1 CMAOLVNGLTWICC-UHFFFAOYSA-N 0.000 claims description 4
- 229910021551 Vanadium(III) chloride Inorganic materials 0.000 claims description 4
- HQYCOEXWFMFWLR-UHFFFAOYSA-K vanadium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[V+3] HQYCOEXWFMFWLR-UHFFFAOYSA-K 0.000 claims description 4
- 150000001993 dienes Chemical class 0.000 claims description 3
- JBIQAPKSNFTACH-UHFFFAOYSA-K vanadium oxytrichloride Chemical compound Cl[V](Cl)(Cl)=O JBIQAPKSNFTACH-UHFFFAOYSA-K 0.000 claims description 3
- 229910052782 aluminium Inorganic materials 0.000 claims 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 6
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- ZHXZNKNQUHUIGN-UHFFFAOYSA-N chloro hypochlorite;vanadium Chemical compound [V].ClOCl ZHXZNKNQUHUIGN-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 description 2
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 2
- UAIZDWNSWGTKFZ-UHFFFAOYSA-L ethylaluminum(2+);dichloride Chemical compound CC[Al](Cl)Cl UAIZDWNSWGTKFZ-UHFFFAOYSA-L 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 239000001282 iso-butane Substances 0.000 description 2
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 description 2
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 2
- WWUVJRULCWHUSA-UHFFFAOYSA-N 2-methyl-1-pentene Chemical compound CCCC(C)=C WWUVJRULCWHUSA-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229920002367 Polyisobutene Polymers 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000005234 alkyl aluminium group Chemical group 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- RYPKRALMXUUNKS-UHFFFAOYSA-N hex-2-ene Chemical compound CCCC=CC RYPKRALMXUUNKS-UHFFFAOYSA-N 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 239000003039 volatile agent Substances 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
- C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F10/14—Monomers containing five or more carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702014394 DE2014394A1 (de) | 1970-03-25 | 1970-03-25 | Verfahren zur Polymerisation von Vinylidenkohlenwasserstoffen, gegebenenfalls im Gemisch mit anderen Olefinen |
| LU62838D LU62838A1 (cg-RX-API-DMAC10.html) | 1970-03-25 | 1971-03-23 | |
| NL7103944A NL7103944A (cg-RX-API-DMAC10.html) | 1970-03-25 | 1971-03-24 | |
| BE764821A BE764821A (fr) | 1970-03-25 | 1971-03-25 | Procede de polymerisation des hydrocarbures de vinylidene en melange avec d'autres olefines |
| FR7110649A FR2087838A5 (cg-RX-API-DMAC10.html) | 1970-03-25 | 1971-03-25 | |
| GB2528971A GB1310064A (en) | 1970-03-25 | 1971-04-19 | Method of polymerising vinylidene hydrocarbons optionally mixed with other olefins |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702014394 DE2014394A1 (de) | 1970-03-25 | 1970-03-25 | Verfahren zur Polymerisation von Vinylidenkohlenwasserstoffen, gegebenenfalls im Gemisch mit anderen Olefinen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2014394A1 true DE2014394A1 (de) | 1971-10-14 |
Family
ID=5766278
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702014394 Pending DE2014394A1 (de) | 1970-03-25 | 1970-03-25 | Verfahren zur Polymerisation von Vinylidenkohlenwasserstoffen, gegebenenfalls im Gemisch mit anderen Olefinen |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE764821A (cg-RX-API-DMAC10.html) |
| DE (1) | DE2014394A1 (cg-RX-API-DMAC10.html) |
| FR (1) | FR2087838A5 (cg-RX-API-DMAC10.html) |
| GB (1) | GB1310064A (cg-RX-API-DMAC10.html) |
| LU (1) | LU62838A1 (cg-RX-API-DMAC10.html) |
| NL (1) | NL7103944A (cg-RX-API-DMAC10.html) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0641810A1 (de) * | 1993-09-04 | 1995-03-08 | Basf Aktiengesellschaft | Carboxylgruppenhaltige Isobuten-Copolymerisate |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3329877A1 (de) * | 1983-08-18 | 1985-03-07 | Rudolf 8000 München Hinterwaldner | Hydrophobe und/oder abhaesive masse, reaktiver verduenner und weichmacher und deren verwendung |
| US4940846A (en) * | 1983-08-18 | 1990-07-10 | Rudolf Hinterwaldner | Hydrophobic and/or abhesive materials, reactive diluents |
| US5210121A (en) * | 1983-08-18 | 1993-05-11 | The Permethyl Corporation | Hydrophobic and/or abhesive materials, reactive diluents, and reactive plasticizers |
-
1970
- 1970-03-25 DE DE19702014394 patent/DE2014394A1/de active Pending
-
1971
- 1971-03-23 LU LU62838D patent/LU62838A1/xx unknown
- 1971-03-24 NL NL7103944A patent/NL7103944A/xx unknown
- 1971-03-25 FR FR7110649A patent/FR2087838A5/fr not_active Expired
- 1971-03-25 BE BE764821A patent/BE764821A/xx unknown
- 1971-04-19 GB GB2528971A patent/GB1310064A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0641810A1 (de) * | 1993-09-04 | 1995-03-08 | Basf Aktiengesellschaft | Carboxylgruppenhaltige Isobuten-Copolymerisate |
Also Published As
| Publication number | Publication date |
|---|---|
| BE764821A (fr) | 1971-08-16 |
| FR2087838A5 (cg-RX-API-DMAC10.html) | 1971-12-31 |
| GB1310064A (en) | 1973-03-14 |
| NL7103944A (cg-RX-API-DMAC10.html) | 1971-09-28 |
| LU62838A1 (cg-RX-API-DMAC10.html) | 1971-08-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHW | Rejection |