DE2102469C2 - Verwendung von Äthylencopolymerisaten als Zusatz zu Erdöl und Erdölfraktionen - Google Patents
Verwendung von Äthylencopolymerisaten als Zusatz zu Erdöl und ErdölfraktionenInfo
- Publication number
- DE2102469C2 DE2102469C2 DE19712102469 DE2102469A DE2102469C2 DE 2102469 C2 DE2102469 C2 DE 2102469C2 DE 19712102469 DE19712102469 DE 19712102469 DE 2102469 A DE2102469 A DE 2102469A DE 2102469 C2 DE2102469 C2 DE 2102469C2
- Authority
- DE
- Germany
- Prior art keywords
- parts
- petroleum
- ethylene
- weight
- reactor
- 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
- 239000003208 petroleum Substances 0.000 title claims description 18
- 239000000654 additive Substances 0.000 title claims description 5
- 230000000996 additive effect Effects 0.000 title claims description 5
- 229920001038 ethylene copolymer Polymers 0.000 title description 7
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 25
- 239000005977 Ethylene Substances 0.000 claims description 25
- 239000003054 catalyst Substances 0.000 claims description 20
- 239000011541 reaction mixture Substances 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 11
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 claims description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 239000001301 oxygen Substances 0.000 claims description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- -1 Methy.'äthylketon Chemical compound 0.000 claims description 7
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 6
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
- 150000001298 alcohols Chemical class 0.000 claims description 4
- 239000000178 monomer Substances 0.000 claims description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims description 3
- 239000003995 emulsifying agent Substances 0.000 claims description 3
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims description 3
- FXHGMKSSBGDXIY-UHFFFAOYSA-N heptanal Chemical compound CCCCCCC=O FXHGMKSSBGDXIY-UHFFFAOYSA-N 0.000 claims description 3
- 230000000379 polymerizing effect Effects 0.000 claims description 3
- 229920001567 vinyl ester resin Polymers 0.000 claims description 3
- 125000005395 methacrylic acid group Chemical group 0.000 claims description 2
- 229920000642 polymer Polymers 0.000 description 19
- 238000006116 polymerization reaction Methods 0.000 description 17
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 11
- 229920001577 copolymer Polymers 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 238000000034 method Methods 0.000 description 7
- 239000000047 product Substances 0.000 description 5
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 4
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 238000007334 copolymerization reaction Methods 0.000 description 4
- 150000002978 peroxides Chemical class 0.000 description 4
- 239000003505 polymerization initiator Substances 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 239000013256 coordination polymer Substances 0.000 description 2
- 230000007717 exclusion Effects 0.000 description 2
- 230000009969 flowable effect Effects 0.000 description 2
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 2
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 241001233037 catfish Species 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 150000001934 cyclohexanes Chemical class 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- FWLDHHJLVGRRHD-UHFFFAOYSA-N decyl prop-2-enoate Chemical compound CCCCCCCCCCOC(=O)C=C FWLDHHJLVGRRHD-UHFFFAOYSA-N 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 description 1
- MEGHWIAOTJPCHQ-UHFFFAOYSA-N ethenyl butanoate Chemical compound CCCC(=O)OC=C MEGHWIAOTJPCHQ-UHFFFAOYSA-N 0.000 description 1
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 210000000540 fraction c Anatomy 0.000 description 1
- LNCPIMCVTKXXOY-UHFFFAOYSA-N hexyl 2-methylprop-2-enoate Chemical compound CCCCCCOC(=O)C(C)=C LNCPIMCVTKXXOY-UHFFFAOYSA-N 0.000 description 1
- LNMQRPPRQDGUDR-UHFFFAOYSA-N hexyl prop-2-enoate Chemical compound CCCCCCOC(=O)C=C LNMQRPPRQDGUDR-UHFFFAOYSA-N 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- 230000001976 improved effect Effects 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 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
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)
- Lubricants (AREA)
- Polymerisation Methods In General (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712102469 DE2102469C2 (de) | 1971-01-20 | 1971-01-20 | Verwendung von Äthylencopolymerisaten als Zusatz zu Erdöl und Erdölfraktionen |
| FR7200121A FR2122425B1 (forum.php) | 1971-01-20 | 1972-01-04 | |
| BE778122A BE778122A (fr) | 1971-01-20 | 1972-01-17 | Procede de preparation de copolymeres de l'ethylene a bas poidsmoleculaire |
| JP701172A JPS556641B1 (forum.php) | 1971-01-20 | 1972-01-19 | |
| GB249972A GB1368159A (en) | 1971-01-20 | 1972-01-19 | Manufacture of low molecular weight dthylene copolymers |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712102469 DE2102469C2 (de) | 1971-01-20 | 1971-01-20 | Verwendung von Äthylencopolymerisaten als Zusatz zu Erdöl und Erdölfraktionen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2102469A1 DE2102469A1 (de) | 1972-08-03 |
| DE2102469C2 true DE2102469C2 (de) | 1989-06-29 |
Family
ID=5796356
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712102469 Expired DE2102469C2 (de) | 1971-01-20 | 1971-01-20 | Verwendung von Äthylencopolymerisaten als Zusatz zu Erdöl und Erdölfraktionen |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS556641B1 (forum.php) |
| BE (1) | BE778122A (forum.php) |
| DE (1) | DE2102469C2 (forum.php) |
| FR (1) | FR2122425B1 (forum.php) |
| GB (1) | GB1368159A (forum.php) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1914756C3 (de) * | 1968-04-01 | 1985-05-15 | Exxon Research and Engineering Co., Linden, N.J. | Verwendung von Ethylen-Vinylacetat- Mischpolymerisaten für Erdöl-Destillate |
| CA1071865A (en) * | 1975-03-28 | 1980-02-19 | Max J. Wisotsky | Polymer combinations useful in distillate hydrocarbon oils to improve cold flow properties |
| GB8401567D0 (en) * | 1984-01-20 | 1984-02-22 | Exxon Research Engineering Co | Polyethylene wax |
| DE3607444A1 (de) * | 1986-03-07 | 1987-09-10 | Roehm Gmbh | Additive fuer mineraloele mit stockpunktverbessernder wirkung |
| DE3640613A1 (de) * | 1986-11-27 | 1988-06-09 | Ruhrchemie Ag | Verfahren zur herstellung von ethylen-mischpolymerisaten und deren verwendung als zusatz zu mineraloel und mineraloelfraktionen |
| DE3742630A1 (de) * | 1987-12-16 | 1989-06-29 | Hoechst Ag | Polymermischungen fuer die verbesserung der fliessfaehigkeit von mineraloeldestillaten in der kaelte |
| WO1992013013A1 (en) * | 1989-02-27 | 1992-08-06 | The Dow Chemical Company | Process for producing homogeneous modified copolymers of ethylene/alpha-olefin carboxylic acids or esters |
| DE4020639A1 (de) * | 1990-06-29 | 1992-01-02 | Hoechst Ag | Verfahren zur herstellung von ethylen-/vinylester-copolymerisaten |
| DE4227905A1 (de) * | 1992-08-22 | 1994-02-24 | Hoechst Ag | Mischpolymerisate des Ethylens |
| FR2698368B1 (fr) * | 1992-11-26 | 1995-01-06 | Atochem Elf Sa | Procédé de préparation de copolymères éthylène-acétate de vinyle de faible masse molaire. |
| GB9403660D0 (en) * | 1994-02-25 | 1994-04-13 | Exxon Chemical Patents Inc | Oil compositions |
| DE19644269A1 (de) * | 1996-10-24 | 1998-04-30 | Basf Ag | Verfahren zur Herstellung ketogruppenenthaltender Polyethylenwachse |
| DE19729057A1 (de) * | 1997-07-08 | 1999-01-14 | Clariant Gmbh | Copolymere auf Basis von Ethylen und ungesättigten Carbonsäureestern und ihre Verwendung als Mineralöladditive |
| DE10356595A1 (de) | 2003-12-04 | 2005-06-30 | Basf Ag | Brennstoffölzusammensetzungen mit verbesserten Kaltfließeigenschaften |
| EP1923454A1 (de) | 2006-11-17 | 2008-05-21 | Basf Se | Kaltfliessverbesserer |
| US9574146B2 (en) | 2012-12-18 | 2017-02-21 | Basf Se | Polymeric compositions composed of ethylene-vinyl ester copolymers alkyl (meth)acrylates, processes for production thereof and use thereof as pour point depressants for crude oils, mineral oils or mineral oil products |
| RU2015129303A (ru) | 2012-12-18 | 2017-01-26 | Басф Се | Полимерные композиции в растворителях с высокой температурой воспламенения, способ их получения и их применение в качестве депрессантных присадок, понижающих температуру застывания сырых нефтей, нефтяных топлив или нефтепродуктов |
| BR112015013238B1 (pt) | 2012-12-18 | 2021-05-25 | Basf Se | composição polimérica, e, uso de uma composição polimérica |
| EA035184B1 (ru) | 2015-11-27 | 2020-05-12 | Басф Се | Сополимеры, содержащие -олефины и олефиновые эфиры дикарбоновой кислоты, способ их получения и их применение в качестве понизителей температуры застывания для неочищенной нефти, минеральных масел и полученных из минеральных масел продуктов |
| AU2019233664A1 (en) * | 2018-03-16 | 2020-09-24 | Basf Se | A high-pressure polymerization process for liquid ethylene copolymers |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3117110A (en) * | 1959-04-28 | 1964-01-07 | Union Carbide Corp | Process for producing solid chain-terminated polymers of ethylene and alkyl acrylates |
| US3048479A (en) * | 1959-08-03 | 1962-08-07 | Exxon Research Engineering Co | Ethylene-vinyl ester pour depressant for middle distillates |
| US3093623A (en) * | 1960-01-05 | 1963-06-11 | Exxon Research Engineering Co | Process for the manufacture of improved pour depressants for middle distillates |
| FR1379344A (fr) * | 1963-01-04 | 1964-11-20 | Monsanto Chemicals | Procédé de polymérisation et de copolymérisation de l'éthylène pour former desrésines |
| NO121523B (forum.php) * | 1964-12-11 | 1971-03-08 | Exxon Co | |
| NL134313C (forum.php) * | 1966-06-01 | |||
| DE1914756C3 (de) * | 1968-04-01 | 1985-05-15 | Exxon Research and Engineering Co., Linden, N.J. | Verwendung von Ethylen-Vinylacetat- Mischpolymerisaten für Erdöl-Destillate |
| US3449251A (en) * | 1968-05-28 | 1969-06-10 | Exxon Research Engineering Co | Wax crystal modifiers for hydrocarbon oils |
-
1971
- 1971-01-20 DE DE19712102469 patent/DE2102469C2/de not_active Expired
-
1972
- 1972-01-04 FR FR7200121A patent/FR2122425B1/fr not_active Expired
- 1972-01-17 BE BE778122A patent/BE778122A/xx not_active IP Right Cessation
- 1972-01-19 JP JP701172A patent/JPS556641B1/ja active Pending
- 1972-01-19 GB GB249972A patent/GB1368159A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2102469A1 (de) | 1972-08-03 |
| JPS556641B1 (forum.php) | 1980-02-19 |
| FR2122425A1 (forum.php) | 1972-09-01 |
| GB1368159A (en) | 1974-09-25 |
| FR2122425B1 (forum.php) | 1976-06-11 |
| BE778122A (fr) | 1972-07-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8125 | Change of the main classification |
Ipc: C10L 1/18 |
|
| D2 | Grant after examination | ||
| 8363 | Opposition against the patent | ||
| 8366 | Restricted maintained after opposition proceedings | ||
| 8305 | Restricted maintenance of patent after opposition | ||
| D4 | Patent maintained restricted |