DE1237323B - Verfahren zur Herstellung von Copolymeren von AEthylen und alpha-Olefinen - Google Patents
Verfahren zur Herstellung von Copolymeren von AEthylen und alpha-OlefinenInfo
- Publication number
- DE1237323B DE1237323B DEM50656A DEM0050656A DE1237323B DE 1237323 B DE1237323 B DE 1237323B DE M50656 A DEM50656 A DE M50656A DE M0050656 A DEM0050656 A DE M0050656A DE 1237323 B DE1237323 B DE 1237323B
- Authority
- DE
- Germany
- Prior art keywords
- ethylene
- polymerization
- copolymers
- copolymer
- 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.)
- Withdrawn
Links
- 229920001577 copolymer Polymers 0.000 title claims description 47
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 title claims description 29
- 239000005977 Ethylene Substances 0.000 title claims description 29
- 238000000034 method Methods 0.000 title claims description 15
- 238000002360 preparation method Methods 0.000 title claims description 12
- 239000004711 α-olefin Substances 0.000 title description 5
- 239000003054 catalyst Substances 0.000 claims description 48
- 238000006116 polymerization reaction Methods 0.000 claims description 16
- 229910052720 vanadium Inorganic materials 0.000 claims description 12
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 claims description 12
- 239000000178 monomer Substances 0.000 claims description 11
- -1 aluminum halides Chemical class 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 7
- 229910052782 aluminium Inorganic materials 0.000 claims description 5
- FSJSYDFBTIVUFD-SUKNRPLKSA-N (z)-4-hydroxypent-3-en-2-one;oxovanadium Chemical compound [V]=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O FSJSYDFBTIVUFD-SUKNRPLKSA-N 0.000 claims description 3
- 239000012442 inert solvent Substances 0.000 claims description 3
- 125000005287 vanadyl group Chemical group 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 230000001105 regulatory effect Effects 0.000 claims 1
- 239000011701 zinc Substances 0.000 claims 1
- 229910052725 zinc Inorganic materials 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 23
- 238000007334 copolymerization reaction Methods 0.000 description 14
- 239000000203 mixture Substances 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 11
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 11
- 239000002904 solvent Substances 0.000 description 9
- 238000009835 boiling Methods 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 229920006395 saturated elastomer Polymers 0.000 description 7
- 150000003682 vanadium compounds Chemical class 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 230000003197 catalytic effect Effects 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000009826 distribution Methods 0.000 description 4
- 239000007791 liquid phase Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 230000002285 radioactive effect Effects 0.000 description 3
- 238000002441 X-ray diffraction Methods 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 125000005234 alkyl aluminium group Chemical group 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 2
- 238000005194 fractionation Methods 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 150000002902 organometallic compounds Chemical class 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- 229910021552 Vanadium(IV) chloride Inorganic materials 0.000 description 1
- 238000002083 X-ray spectrum Methods 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 125000005595 acetylacetonate group Chemical group 0.000 description 1
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical group CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- WXCZUWHSJWOTRV-UHFFFAOYSA-N but-1-ene;ethene Chemical compound C=C.CCC=C WXCZUWHSJWOTRV-UHFFFAOYSA-N 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- HRXSKIOIHQEGAI-UHFFFAOYSA-M diethylalumanylium;fluoride Chemical compound CC[Al](F)CC HRXSKIOIHQEGAI-UHFFFAOYSA-M 0.000 description 1
- CQYBWJYIKCZXCN-UHFFFAOYSA-N diethylaluminum Chemical compound CC[Al]CC CQYBWJYIKCZXCN-UHFFFAOYSA-N 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 229920001198 elastomeric copolymer Polymers 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000008246 gaseous mixture Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 150000003623 transition metal compounds Chemical class 0.000 description 1
- LSGOVYNHVSXFFJ-UHFFFAOYSA-N vanadate(3-) Chemical class [O-][V]([O-])([O-])=O LSGOVYNHVSXFFJ-UHFFFAOYSA-N 0.000 description 1
- JBIQAPKSNFTACH-UHFFFAOYSA-K vanadium oxytrichloride Chemical compound Cl[V](Cl)(Cl)=O JBIQAPKSNFTACH-UHFFFAOYSA-K 0.000 description 1
- JTJFQBNJBPPZRI-UHFFFAOYSA-J vanadium tetrachloride Chemical compound Cl[V](Cl)(Cl)Cl JTJFQBNJBPPZRI-UHFFFAOYSA-J 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
- C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
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)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT1849660 | 1960-10-26 | ||
| IT397962 | 1962-02-27 | ||
| IT763862 | 1962-04-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1237323B true DE1237323B (de) | 1967-03-23 |
Family
ID=27272605
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEM50656A Withdrawn DE1237323B (de) | 1960-10-26 | 1961-10-23 | Verfahren zur Herstellung von Copolymeren von AEthylen und alpha-Olefinen |
| DE19631520288 Withdrawn DE1520288B2 (de) | 1960-10-26 | 1963-02-25 | Verfahren zur herstellung von copolymeren von aethylen und alpha olefinen |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19631520288 Withdrawn DE1520288B2 (de) | 1960-10-26 | 1963-02-25 | Verfahren zur herstellung von copolymeren von aethylen und alpha olefinen |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3369011A (en, 2012) |
| BE (3) | BE609581A (en, 2012) |
| CH (1) | CH428224A (en, 2012) |
| DE (2) | DE1237323B (en, 2012) |
| DK (1) | DK132227C (en, 2012) |
| FR (1) | FR1304407A (en, 2012) |
| GB (3) | GB957068A (en, 2012) |
| LU (3) | LU40742A1 (en, 2012) |
| NL (3) | NL269998A (en, 2012) |
| SE (1) | SE323207B (en, 2012) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL123463C (en, 2012) * | 1964-04-08 | |||
| US3496135A (en) * | 1968-02-02 | 1970-02-17 | Du Pont | Crude epdm copolymer stabilized with a lewis base |
| JPS52156195A (en) * | 1976-06-22 | 1977-12-26 | Mitsubishi Chem Ind Ltd | Production of solid catalyst and olefin polymers |
| US4559318A (en) * | 1983-04-26 | 1985-12-17 | Phillips Petroleum Company | Supported vanadium dihalide-ether complex catalyst |
| US5210161A (en) * | 1983-04-26 | 1993-05-11 | Phillips Petroleum Company | Supported vanadium dihalide-ether complex catalyst |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE564772A (en, 2012) * | ||||
| BE554242A (en, 2012) * | 1956-01-18 | |||
| BE559727A (en, 2012) * | 1956-08-02 | |||
| BE574129A (en, 2012) * | 1957-12-23 | |||
| US2996459A (en) * | 1958-02-03 | 1961-08-15 | Monsanto Chemicals | Method for preparing a ziegler polymerization catalyst |
| US3205216A (en) * | 1962-04-05 | 1965-09-07 | Monsanto Co | Polymerization process with ziegler catalysts |
-
0
- BE BE631164D patent/BE631164A/xx unknown
- NL NL289135D patent/NL289135A/xx unknown
- NL NL291400D patent/NL291400A/xx unknown
- BE BE628896D patent/BE628896A/xx unknown
- BE BE609581D patent/BE609581A/xx unknown
- NL NL269998D patent/NL269998A/xx unknown
-
1961
- 1961-09-11 GB GB32540/61A patent/GB957068A/en not_active Expired
- 1961-10-21 LU LU40742A patent/LU40742A1/xx unknown
- 1961-10-21 CH CH1221161A patent/CH428224A/de unknown
- 1961-10-23 DK DK419661A patent/DK132227C/da active
- 1961-10-23 DE DEM50656A patent/DE1237323B/de not_active Withdrawn
- 1961-10-24 FR FR876852A patent/FR1304407A/fr not_active Expired
-
1963
- 1963-02-22 GB GB7318/63A patent/GB985594A/en not_active Expired
- 1963-02-25 DE DE19631520288 patent/DE1520288B2/de not_active Withdrawn
- 1963-02-26 LU LU43254D patent/LU43254A1/xx unknown
- 1963-02-26 SE SE2068/63A patent/SE323207B/xx unknown
- 1963-04-13 LU LU43558D patent/LU43558A1/xx unknown
- 1963-04-16 GB GB14862/63A patent/GB985884A/en not_active Expired
-
1966
- 1966-10-19 US US587936A patent/US3369011A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DK132227C (da) | 1976-04-12 |
| SE323207B (en, 2012) | 1970-04-27 |
| LU40742A1 (en, 2012) | 1962-10-22 |
| BE609581A (en, 2012) | |
| LU43254A1 (en, 2012) | 1964-02-26 |
| NL289135A (en, 2012) | |
| FR1304407A (fr) | 1962-09-21 |
| BE631164A (en, 2012) | |
| BE628896A (en, 2012) | |
| NL291400A (en, 2012) | |
| LU43558A1 (en, 2012) | 1964-04-13 |
| CH428224A (de) | 1967-01-15 |
| GB985884A (en) | 1965-03-10 |
| DK132227B (da) | 1975-11-10 |
| GB957068A (en) | 1964-05-06 |
| DE1520288A1 (de) | 1969-02-20 |
| US3369011A (en) | 1968-02-13 |
| GB985594A (en) | 1965-03-10 |
| NL269998A (en, 2012) | |
| DE1520288B2 (de) | 1971-09-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| E77 | Valid patent as to the heymanns-index 1977 | ||
| EHJ | Ceased/non-payment of the annual fee |