CA1064197A - Polymerization of ethylene with oxygen and organic initiators - Google Patents
Polymerization of ethylene with oxygen and organic initiatorsInfo
- Publication number
- CA1064197A CA1064197A CA232,646A CA232646A CA1064197A CA 1064197 A CA1064197 A CA 1064197A CA 232646 A CA232646 A CA 232646A CA 1064197 A CA1064197 A CA 1064197A
- Authority
- CA
- Canada
- Prior art keywords
- organic
- initiators
- initiator
- reactor
- free radical
- 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
- 239000003999 initiator Substances 0.000 title claims abstract description 84
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 title claims abstract description 21
- 239000005977 Ethylene Substances 0.000 title claims abstract description 21
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 title abstract description 21
- 239000001301 oxygen Substances 0.000 title abstract description 21
- 229910052760 oxygen Inorganic materials 0.000 title abstract description 21
- 238000006116 polymerization reaction Methods 0.000 title abstract description 13
- 239000000178 monomer Substances 0.000 claims abstract description 39
- 229920000642 polymer Polymers 0.000 claims abstract description 25
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims abstract description 23
- 230000003287 optical effect Effects 0.000 claims abstract description 7
- 239000012632 extractable Substances 0.000 claims abstract description 5
- 238000000034 method Methods 0.000 claims description 20
- 230000000977 initiatory effect Effects 0.000 claims description 13
- 150000003254 radicals Chemical class 0.000 claims description 10
- 239000012986 chain transfer agent Substances 0.000 claims description 8
- 238000005086 pumping Methods 0.000 claims description 3
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 claims description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- 229910001882 dioxygen Inorganic materials 0.000 claims description 2
- 229920001519 homopolymer Polymers 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 25
- 239000003795 chemical substances by application Substances 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- -1 cyclic peroxides Chemical class 0.000 description 9
- 239000011347 resin Substances 0.000 description 7
- 229920005989 resin Polymers 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 150000002978 peroxides Chemical class 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000002671 adjuvant Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000011953 free-radical catalyst Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000012969 di-tertiary-butyl peroxide Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 238000009413 insulation Methods 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- MHCVCKDNQYMGEX-UHFFFAOYSA-N 1,1'-biphenyl;phenoxybenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1OC1=CC=CC=C1 MHCVCKDNQYMGEX-UHFFFAOYSA-N 0.000 description 1
- 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-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- HXWHLVCLDRKXPQ-UHFFFAOYSA-N bis(tert-butylperoxy)-dimethylsilane Chemical compound CC(C)(C)OO[Si](C)(C)OOC(C)(C)C HXWHLVCLDRKXPQ-UHFFFAOYSA-N 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 229950005499 carbon tetrachloride Drugs 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012933 diacyl peroxide Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 229910052736 halogen Chemical group 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- NFMHSPWHNQRFNR-UHFFFAOYSA-N hyponitrous acid Chemical class ON=NO NFMHSPWHNQRFNR-UHFFFAOYSA-N 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 150000002976 peresters Chemical class 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- KOPQZJAYZFAPBC-UHFFFAOYSA-N propanoyl propaneperoxoate Chemical compound CCC(=O)OOC(=O)CC KOPQZJAYZFAPBC-UHFFFAOYSA-N 0.000 description 1
- 235000015096 spirit Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-UHFFFAOYSA-N 0.000 description 1
- PFBLRDXPNUJYJM-UHFFFAOYSA-N tert-butyl 2-methylpropaneperoxoate Chemical compound CC(C)C(=O)OOC(C)(C)C PFBLRDXPNUJYJM-UHFFFAOYSA-N 0.000 description 1
- XTXFUQOLBKQKJU-UHFFFAOYSA-N tert-butylperoxy(trimethyl)silane Chemical compound CC(C)(C)OO[Si](C)(C)C XTXFUQOLBKQKJU-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 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
- C08F10/02—Ethene
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)
- Polymerization Catalysts (AREA)
- Polymerisation Methods In General (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/501,701 US4000357A (en) | 1974-08-29 | 1974-08-29 | Polymerization of ethylene with oxygen and organic initiators |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1064197A true CA1064197A (en) | 1979-10-09 |
Family
ID=23994679
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA232,646A Expired CA1064197A (en) | 1974-08-29 | 1975-07-31 | Polymerization of ethylene with oxygen and organic initiators |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4000357A (https=) |
| JP (1) | JPS5150387A (https=) |
| AU (1) | AU501340B2 (https=) |
| BR (1) | BR7505513A (https=) |
| CA (1) | CA1064197A (https=) |
| ES (1) | ES440547A1 (https=) |
| FI (1) | FI61497C (https=) |
| GB (1) | GB1516146A (https=) |
| IN (1) | IN143620B (https=) |
| IT (1) | IT1042145B (https=) |
| NO (1) | NO752958L (https=) |
| SE (1) | SE423817B (https=) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4452956A (en) * | 1979-11-09 | 1984-06-05 | Union Carbide Corporation | Discrete spiral flow imparting device |
| DE3912975A1 (de) * | 1989-04-20 | 1990-11-08 | Basf Ag | Polyethylen sowie copolymerisate aus ueberwiegenden anteilen von ethylen |
| US6359083B1 (en) * | 2000-05-02 | 2002-03-19 | Eastman Chemical Company | Olefin polymerization process |
| DE10064752A1 (de) * | 2000-12-22 | 2002-07-04 | Basell Polyolefine Gmbh | Geruchlose Polyethylenhomo- und copolymere mit guten mechanischen Eigenschaften |
| WO2003019252A1 (fr) * | 2001-08-31 | 2003-03-06 | Fuji Photo Film Co., Ltd. | Procede permettant la production de composants optiques en plastique |
| ES3055648T3 (en) * | 2018-06-12 | 2026-02-13 | Nouryon Chemicals Int Bv | Process for the production of composite articles |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3142666A (en) * | 1959-03-05 | 1964-07-28 | Monsanto Co | Ethylene polymerization utilizing two organic peroxygen compounds as catalysts |
| US3092614A (en) * | 1962-02-15 | 1963-06-04 | Union Carbide Corp | Ethylene polymerization process |
| US3293233A (en) * | 1963-04-09 | 1966-12-20 | Rexall Drug Chemical | Process for polymerizing ethylene at high pressures in the presence of a mixture of peroxides having different half lives |
| US3691145A (en) * | 1970-08-06 | 1972-09-12 | Basf Ag | Production of polyethylene by the high pressure process using a mixture of tertiary butyl hydroperoxide and oxygen as the initiator |
-
1974
- 1974-08-29 US US05/501,701 patent/US4000357A/en not_active Expired - Lifetime
-
1975
- 1975-07-31 CA CA232,646A patent/CA1064197A/en not_active Expired
- 1975-08-27 AU AU84295/75A patent/AU501340B2/en not_active Expired
- 1975-08-28 BR BR7505513A patent/BR7505513A/pt unknown
- 1975-08-28 JP JP50103545A patent/JPS5150387A/ja active Pending
- 1975-08-28 FI FI752418A patent/FI61497C/fi not_active IP Right Cessation
- 1975-08-28 ES ES440547A patent/ES440547A1/es not_active Expired
- 1975-08-28 NO NO752958A patent/NO752958L/no unknown
- 1975-08-28 SE SE7509588A patent/SE423817B/xx not_active IP Right Cessation
- 1975-08-28 IN IN1663/CAL/75A patent/IN143620B/en unknown
- 1975-08-28 GB GB35494/75A patent/GB1516146A/en not_active Expired
- 1975-08-28 IT IT26700/75A patent/IT1042145B/it active
Also Published As
| Publication number | Publication date |
|---|---|
| GB1516146A (en) | 1978-06-28 |
| US4000357A (en) | 1976-12-28 |
| BR7505513A (pt) | 1977-03-15 |
| ES440547A1 (es) | 1977-03-01 |
| JPS5150387A (en) | 1976-05-01 |
| FI61497C (fi) | 1982-08-10 |
| FI61497B (fi) | 1982-04-30 |
| AU501340B2 (en) | 1979-06-14 |
| NO752958L (https=) | 1976-03-02 |
| SE423817B (sv) | 1982-06-07 |
| FI752418A7 (https=) | 1976-03-01 |
| IT1042145B (it) | 1980-01-30 |
| IN143620B (https=) | 1978-01-07 |
| SE7509588L (sv) | 1976-05-03 |
| AU8429575A (en) | 1977-03-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US6844408B2 (en) | Preparation of polyethylene | |
| CN103261244B (zh) | 在自由基聚合引发剂存在下通过使乙烯、双官能或多官能共聚单体和任选的其它共聚单体共聚来制备乙烯共聚物的方法 | |
| KR101708136B1 (ko) | 에틸렌과 비닐 알코올 에스테르의 공중합 공정 | |
| US4794004A (en) | Preparation of copolymers of ethylene with vinyl esters in a tubular reactor at above 500 bar | |
| EP1678216B1 (en) | Continuous preparation of ethylene homopolymers or copolymers | |
| CA1064197A (en) | Polymerization of ethylene with oxygen and organic initiators | |
| US3642726A (en) | Thermoplastic crosslinked polyester material and method of molding | |
| US4076919A (en) | Manufacture of ethylene polymers in a two-zone tubular reactor at pressure above 500 bars | |
| CN1266171C (zh) | 乙烯高压聚合方法 | |
| KR102181338B1 (ko) | 폴리에틸렌의 제조 방법 | |
| US6894126B2 (en) | Method for producing ethylene homopolymers and copolymers by means of radical high pressure polymerization | |
| US4074040A (en) | Manufacture of ethylene polymers in an autoclave reactor | |
| US5306791A (en) | Ethylene homopolymers and ethylene copolymers and a process for their preparation | |
| US10858462B2 (en) | Ethylene copolymers and process for the production thereof | |
| JPS5831088B2 (ja) | 酸素および有機開始剤類によるエチレン重合 | |
| US4177340A (en) | Manufacture of high-pressure polyethylene | |
| US3299177A (en) | Polyethylene modified with branched polyethylene wax | |
| US6262225B1 (en) | Carbon monoxide containing polymers derived from synthesis gas (KWP-0002) | |
| JPH05339318A (ja) | 多官能性有機過酸化物重合開始剤による押出コ−ティング用エチレン重合体の製造方法 | |
| US3560463A (en) | Copolymers of ethylene with cetyl vinyl ether or n-octadecyl vinyl ether | |
| US4617365A (en) | Ethylene copolymer | |
| KR20240051235A (ko) | 가변 온도 관형 반응기 프로파일 및 이로부터 제조된 중밀도 폴리에틸렌 조성물 |