CA2253709A1 - Continuous process for the production of poly(1-alkenes) - Google Patents
Continuous process for the production of poly(1-alkenes) Download PDFInfo
- Publication number
- CA2253709A1 CA2253709A1 CA002253709A CA2253709A CA2253709A1 CA 2253709 A1 CA2253709 A1 CA 2253709A1 CA 002253709 A CA002253709 A CA 002253709A CA 2253709 A CA2253709 A CA 2253709A CA 2253709 A1 CA2253709 A1 CA 2253709A1
- Authority
- CA
- Canada
- Prior art keywords
- reactor
- monomer
- reaction mixture
- catalyst
- olefin
- 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.)
- Abandoned
Links
- 238000010924 continuous production Methods 0.000 title claims abstract description 6
- 238000004519 manufacturing process Methods 0.000 title description 8
- 238000000034 method Methods 0.000 claims abstract description 70
- 230000008569 process Effects 0.000 claims abstract description 49
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000001257 hydrogen Substances 0.000 claims abstract description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
- 239000003054 catalyst Substances 0.000 claims description 161
- 239000011541 reaction mixture Substances 0.000 claims description 121
- 239000000178 monomer Substances 0.000 claims description 103
- 238000006243 chemical reaction Methods 0.000 claims description 71
- 238000006116 polymerization reaction Methods 0.000 claims description 30
- 239000007788 liquid Substances 0.000 claims description 23
- 239000002904 solvent Substances 0.000 claims description 19
- 230000008859 change Effects 0.000 claims description 9
- 239000012968 metallocene catalyst Substances 0.000 claims description 8
- 238000002156 mixing Methods 0.000 claims description 8
- 150000004291 polyenes Chemical class 0.000 claims description 2
- 125000002524 organometallic group Chemical group 0.000 claims 2
- 229910052723 transition metal Inorganic materials 0.000 claims 2
- 150000003624 transition metals Chemical class 0.000 claims 2
- 229920000642 polymer Polymers 0.000 abstract description 94
- 239000000463 material Substances 0.000 abstract description 27
- 230000000379 polymerizing effect Effects 0.000 abstract 1
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 62
- 239000000203 mixture Substances 0.000 description 32
- 239000000725 suspension Substances 0.000 description 30
- 239000000047 product Substances 0.000 description 28
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 24
- 239000000523 sample Substances 0.000 description 22
- 229910001868 water Inorganic materials 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 19
- 238000010791 quenching Methods 0.000 description 19
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 18
- 238000012986 modification Methods 0.000 description 17
- 230000004048 modification Effects 0.000 description 17
- 230000003068 static effect Effects 0.000 description 14
- -1 C6-C Chemical class 0.000 description 13
- 238000000746 purification Methods 0.000 description 13
- 238000013461 design Methods 0.000 description 12
- 229910001220 stainless steel Inorganic materials 0.000 description 11
- 239000010935 stainless steel Substances 0.000 description 10
- 238000012546 transfer Methods 0.000 description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 9
- 238000009826 distribution Methods 0.000 description 9
- 239000001301 oxygen Substances 0.000 description 9
- 229910052760 oxygen Inorganic materials 0.000 description 9
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 7
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000010006 flight Effects 0.000 description 6
- 239000012530 fluid Substances 0.000 description 6
- 239000004820 Pressure-sensitive adhesive Substances 0.000 description 5
- 238000007792 addition Methods 0.000 description 5
- 150000001336 alkenes Chemical class 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 230000002572 peristaltic effect Effects 0.000 description 5
- XWJBRBSPAODJER-UHFFFAOYSA-N 1,7-octadiene Chemical compound C=CCCCCC=C XWJBRBSPAODJER-UHFFFAOYSA-N 0.000 description 4
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000005977 Ethylene Substances 0.000 description 4
- 229910045601 alloy Inorganic materials 0.000 description 4
- 239000000956 alloy Substances 0.000 description 4
- 239000013529 heat transfer fluid Substances 0.000 description 4
- 230000002829 reductive effect Effects 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000003017 thermal stabilizer Substances 0.000 description 4
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- 229910000831 Steel Inorganic materials 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 239000002808 molecular sieve Substances 0.000 description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 3
- 241000894007 species Species 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 239000010959 steel Substances 0.000 description 3
- 150000003623 transition metal compounds Chemical class 0.000 description 3
- JBVMSEMQJGGOFR-FNORWQNLSA-N (4e)-4-methylhexa-1,4-diene Chemical compound C\C=C(/C)CC=C JBVMSEMQJGGOFR-FNORWQNLSA-N 0.000 description 2
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 2
- VSQLAQKFRFTMNS-UHFFFAOYSA-N 5-methylhexa-1,4-diene Chemical compound CC(C)=CCC=C VSQLAQKFRFTMNS-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- 229910003074 TiCl4 Inorganic materials 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000012986 chain transfer agent Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 239000002274 desiccant Substances 0.000 description 2
- 150000001993 dienes Chemical class 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- GWUSZQUVEVMBPI-UHFFFAOYSA-N nimetazepam Chemical compound N=1CC(=O)N(C)C2=CC=C([N+]([O-])=O)C=C2C=1C1=CC=CC=C1 GWUSZQUVEVMBPI-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 230000010355 oscillation Effects 0.000 description 2
- 230000036961 partial effect Effects 0.000 description 2
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 239000004810 polytetrafluoroethylene Substances 0.000 description 2
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 238000005086 pumping Methods 0.000 description 2
- 230000000171 quenching effect Effects 0.000 description 2
- 230000000630 rising effect Effects 0.000 description 2
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 2
- YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 description 2
- 150000005671 trienes Chemical class 0.000 description 2
- DOGRYWZHOBYUMD-BQYQJAHWSA-N (4E)-5-methylhepta-1,4-diene Chemical compound CC\C(C)=C\CC=C DOGRYWZHOBYUMD-BQYQJAHWSA-N 0.000 description 1
- NZXFAMRCCGUQGQ-BQYQJAHWSA-N (4e)-4-methylhepta-1,4-diene Chemical compound CC\C=C(/C)CC=C NZXFAMRCCGUQGQ-BQYQJAHWSA-N 0.000 description 1
- TVEFFNLPYIEDLS-VQHVLOKHSA-N (4e)-deca-1,4,9-triene Chemical compound C=CCCC\C=C\CC=C TVEFFNLPYIEDLS-VQHVLOKHSA-N 0.000 description 1
- BUAQSUJYSBQTHA-BQYQJAHWSA-N (4e)-octa-1,4,7-triene Chemical compound C=CC\C=C\CC=C BUAQSUJYSBQTHA-BQYQJAHWSA-N 0.000 description 1
- GMGYODAMPOELNZ-MDZDMXLPSA-N (5e)-deca-1,5,9-triene Chemical compound C=CCC\C=C\CCC=C GMGYODAMPOELNZ-MDZDMXLPSA-N 0.000 description 1
- VOSLXTGMYNYCPW-UHFFFAOYSA-N 1,10-Undecadiene Chemical compound C=CCCCCCCCC=C VOSLXTGMYNYCPW-UHFFFAOYSA-N 0.000 description 1
- YPVPQMCSLFDIKA-UHFFFAOYSA-N 3-ethylpent-1-ene Chemical compound CCC(CC)C=C YPVPQMCSLFDIKA-UHFFFAOYSA-N 0.000 description 1
- RITONZMLZWYPHW-UHFFFAOYSA-N 3-methylhex-1-ene Chemical compound CCCC(C)C=C RITONZMLZWYPHW-UHFFFAOYSA-N 0.000 description 1
- LDTAOIUHUHHCMU-UHFFFAOYSA-N 3-methylpent-1-ene Chemical compound CCC(C)C=C LDTAOIUHUHHCMU-UHFFFAOYSA-N 0.000 description 1
- AHZPYLAZRVPKIB-UHFFFAOYSA-N 4,5-dimethylhexa-1,4-diene Chemical compound CC(C)=C(C)CC=C AHZPYLAZRVPKIB-UHFFFAOYSA-N 0.000 description 1
- KSJOQAXIIGDYGV-UHFFFAOYSA-N 4-ethylhepta-1,4-diene Chemical compound CCC=C(CC)CC=C KSJOQAXIIGDYGV-UHFFFAOYSA-N 0.000 description 1
- BOCMEYDNTRRDGN-UHFFFAOYSA-N 4-ethylhexa-1,4-diene Chemical compound CCC(=CC)CC=C BOCMEYDNTRRDGN-UHFFFAOYSA-N 0.000 description 1
- YRJNKFONIFEXAQ-UHFFFAOYSA-N 4-ethylocta-1,4-diene Chemical compound CCCC=C(CC)CC=C YRJNKFONIFEXAQ-UHFFFAOYSA-N 0.000 description 1
- SUWJESCICIOQHO-UHFFFAOYSA-N 4-methylhex-1-ene Chemical compound CCC(C)CC=C SUWJESCICIOQHO-UHFFFAOYSA-N 0.000 description 1
- WHYLFTSFYNXJTQ-UHFFFAOYSA-N 4-propyldeca-1,4-diene Chemical compound CCCCCC=C(CCC)CC=C WHYLFTSFYNXJTQ-UHFFFAOYSA-N 0.000 description 1
- RKUREQAWWXZZER-UHFFFAOYSA-N 5-methylocta-1,4-diene Chemical compound CCCC(C)=CCC=C RKUREQAWWXZZER-UHFFFAOYSA-N 0.000 description 1
- 241000256844 Apis mellifera Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229910000669 Chrome steel Inorganic materials 0.000 description 1
- 244000228957 Ferula foetida Species 0.000 description 1
- 229910000760 Hardened steel Inorganic materials 0.000 description 1
- 239000004831 Hot glue Substances 0.000 description 1
- 240000001812 Hyssopus officinalis Species 0.000 description 1
- 235000010650 Hyssopus officinalis Nutrition 0.000 description 1
- 101150005470 LCL2 gene Proteins 0.000 description 1
- 241000282320 Panthera leo Species 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910010061 TiC13 Inorganic materials 0.000 description 1
- 229910010066 TiC14 Inorganic materials 0.000 description 1
- 229910010062 TiCl3 Inorganic materials 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000011437 continuous method Methods 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 238000001723 curing Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000013016 damping Methods 0.000 description 1
- TVEFFNLPYIEDLS-UHFFFAOYSA-N deca-1,4,9-triene Chemical compound C=CCCCC=CCC=C TVEFFNLPYIEDLS-UHFFFAOYSA-N 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 238000005485 electric heating Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229920001973 fluoroelastomer Polymers 0.000 description 1
- 238000007757 hot melt coating Methods 0.000 description 1
- 238000005304 joining Methods 0.000 description 1
- 230000033001 locomotion Effects 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910001092 metal group alloy Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- CPOFMOWDMVWCLF-UHFFFAOYSA-N methyl(oxo)alumane Chemical compound C[Al]=O CPOFMOWDMVWCLF-UHFFFAOYSA-N 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
- 238000005457 optimization Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920002959 polymer blend Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920005606 polypropylene copolymer Polymers 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- XTUSEBKMEQERQV-UHFFFAOYSA-N propan-2-ol;hydrate Chemical compound O.CC(C)O XTUSEBKMEQERQV-UHFFFAOYSA-N 0.000 description 1
- 238000003847 radiation curing Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000011369 resultant mixture Substances 0.000 description 1
- 230000002000 scavenging effect Effects 0.000 description 1
- 238000007790 scraping Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000013517 stratification Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- XMRSTLBCBDIKFI-UHFFFAOYSA-N tetradeca-1,13-diene Chemical compound C=CCCCCCCCCCCC=C XMRSTLBCBDIKFI-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 239000005341 toughened glass Substances 0.000 description 1
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 1
- 238000013022 venting Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/18—Stationary reactors having moving elements inside
- B01J19/20—Stationary reactors having moving elements inside in the form of helices, e.g. screw reactors
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/18—Stationary reactors having moving elements inside
- B01J19/1812—Tubular reactors
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/24—Stationary reactors without moving elements inside
- B01J19/2415—Tubular reactors
-
- 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
- C08F110/00—Homopolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F110/14—Monomers containing five or more carbon atoms
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00002—Chemical plants
- B01J2219/00027—Process aspects
- B01J2219/00033—Continuous processes
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00002—Chemical plants
- B01J2219/00027—Process aspects
- B01J2219/0004—Processes in series
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00049—Controlling or regulating processes
- B01J2219/00051—Controlling the temperature
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polymerisation Methods In General (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/644,611 US5644007A (en) | 1996-04-26 | 1996-04-26 | Continuous process for the production of poly(1-alkenes) |
| US08/644,611 | 1996-04-26 | ||
| PCT/US1996/018776 WO1997041162A1 (en) | 1996-04-26 | 1996-11-21 | Continuous process for the production of poly(1-alkenes) |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2253709A1 true CA2253709A1 (en) | 1997-11-06 |
Family
ID=24585632
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002253709A Abandoned CA2253709A1 (en) | 1996-04-26 | 1996-11-21 | Continuous process for the production of poly(1-alkenes) |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US5644007A (cg-RX-API-DMAC7.html) |
| EP (1) | EP0895515B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP3856840B2 (cg-RX-API-DMAC7.html) |
| KR (1) | KR20000028539A (cg-RX-API-DMAC7.html) |
| CN (1) | CN1217000A (cg-RX-API-DMAC7.html) |
| AU (1) | AU1122297A (cg-RX-API-DMAC7.html) |
| CA (1) | CA2253709A1 (cg-RX-API-DMAC7.html) |
| DE (1) | DE69610338T2 (cg-RX-API-DMAC7.html) |
| WO (1) | WO1997041162A1 (cg-RX-API-DMAC7.html) |
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| US6015779A (en) | 1996-03-19 | 2000-01-18 | Energy & Environmental International, L.C. | Methods for forming amorphous ultra-high molecular weight polyalphaolefin drag reducing agents |
| JP3836228B2 (ja) * | 1996-12-26 | 2006-10-25 | 三井化学株式会社 | 分離流による重合方法 |
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| JP4495846B2 (ja) * | 2000-10-19 | 2010-07-07 | 日本ポリプロ株式会社 | α−オレフィンの重合方法 |
| US6815011B2 (en) | 2000-11-27 | 2004-11-09 | Energy & Environmental International, L.C. | Alpha olefin monomer partitioning agents for drag reducing agents and methods of forming drag reducing agents using alpha olefin monomer partitioning agents |
| CA2434795C (en) | 2001-01-16 | 2010-01-26 | Energy & Environmental International, L.C. | Methods for forming amorphous ultra-high molecular weight polyolefins for use as drag reducing agents |
| US7514263B2 (en) * | 2001-04-02 | 2009-04-07 | 3M Innovative Properties Company | Continuous process for the production of combinatorial libraries of materials |
| US6617020B2 (en) | 2001-04-04 | 2003-09-09 | 3M Innovative Properties Company | Hot melt processable pressure sensitive adhesive comprising organophilic clay plate-like particles, a method of making, and articles made therefrom |
| US7012046B2 (en) * | 2001-06-08 | 2006-03-14 | Eaton Gerald B | Drag reducing agent slurries having alfol alcohols and processes for forming drag reducing agent slurries having alfol alcohols |
| RU2297877C2 (ru) | 2001-06-13 | 2007-04-27 | Энерджи Энд Энвиронментал Интернэшнл, Л.К. | Реакторы для полимеризации в объеме и способы такой полимеризации |
| WO2003026791A1 (en) * | 2001-09-26 | 2003-04-03 | Bp Corporation North America Inc. | Integrated chemical process control |
| US6962946B2 (en) | 2001-11-21 | 2005-11-08 | 3M Innovative Properties Company | Nanoparticles having a rutile-like crystalline phase and method of preparing same |
| AU2002365414A1 (en) * | 2001-11-29 | 2003-06-10 | Parallel Solutions, Inc. | Copolymer libraries and production and use thereof |
| US6686026B2 (en) | 2002-04-08 | 2004-02-03 | 3M Innovative Properties Company | Micro-channeled protective film |
| US6903173B2 (en) * | 2002-08-02 | 2005-06-07 | 3M Innovative Properties Co. | Fluorinated polymers |
| US7632916B2 (en) * | 2002-08-02 | 2009-12-15 | 3M Innovative Properties Company | Process to modify polymeric materials and resulting compositions |
| US7157283B2 (en) * | 2002-08-02 | 2007-01-02 | 3M Innovative Properties Company | Continuous process for the production of combinatorial libraries of modified materials |
| US7133784B2 (en) * | 2002-10-28 | 2006-11-07 | Bp Corporation North America, Inc. | Process and method for chemical manufacturing using transformation of on-line instrumentation data |
| US6716935B1 (en) | 2002-12-19 | 2004-04-06 | 3M Innovative Properties Company | Continuous process for the production of controlled architecture materials under high solids loading conditions |
| US6969490B2 (en) * | 2003-06-26 | 2005-11-29 | 3M Innovative Properties Company | Device for the continuous process for the production of controlled architecture materials |
| US6842288B1 (en) | 2003-10-30 | 2005-01-11 | 3M Innovative Properties Company | Multilayer optical adhesives and articles |
| JP4116529B2 (ja) * | 2003-12-01 | 2008-07-09 | 日東電工株式会社 | 素練りゴムの製造方法 |
| ES2285686T3 (es) * | 2004-02-13 | 2007-11-16 | Total Petrochemicals Research Feluy | Procedimiento y aparato para preparar y suministrar dispersion de catalizadores a un reactor de polimerizacion. |
| DE102005031114A1 (de) * | 2005-07-04 | 2007-01-18 | Basf Ag | Verwendung einer Vorrichtung zur Zugabe mindestens eines Zusatzstoffes in einen Reaktorinnenraum |
| JP5611237B2 (ja) * | 2009-01-23 | 2014-10-22 | エボニック デグサ ゲーエムベーハーＥｖｏｎｉｋ Ｄｅｇｕｓｓａ ＧｍｂＨ | Ｐｅ ｍｉｂスラリー重合 |
| CN102190832B (zh) * | 2010-03-12 | 2013-06-12 | 青岛科技大学 | 聚1-丁烯弹性体材料的制备方法 |
| JP2015530430A (ja) | 2012-08-14 | 2015-10-15 | スリーエム イノベイティブ プロパティズ カンパニー | グラフトイソブチレンコポリマーを含む接着剤 |
| CN105664830B (zh) * | 2016-02-04 | 2017-12-12 | 河南心连心化肥有限公司 | 一体化管式反应装置及其反应方法 |
| EP3758912B1 (en) | 2018-02-28 | 2025-06-04 | 3M Innovative Properties Company | Coextruded polymeric article and method of making the same |
| WO2019166936A1 (en) | 2018-02-28 | 2019-09-06 | 3M Innovative Properties Company | Coextruded polymeric article and method of making the same |
| US12258495B2 (en) | 2018-12-28 | 2025-03-25 | Saint-Gobain Performance Plastics Corporation | Adhesive composition and methods of forming the same |
| US20210094253A1 (en) * | 2019-09-27 | 2021-04-01 | Saint-Gobain Performance Plastics Corporation | Multilayer tube and method for making same |
| CN114524894B (zh) * | 2022-02-22 | 2023-07-25 | 拓烯科技(衢州)有限公司 | 一种聚4-甲基-1-戊烯的制备方法 |
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| US2894824A (en) * | 1955-02-11 | 1959-07-14 | Phillips Petroleum Co | Polymerization apparatus |
| US3074922A (en) * | 1958-07-21 | 1963-01-22 | Phillips Petroleum Co | Polymerization process and apparatus |
| DE1594063A1 (de) * | 1965-08-27 | 1970-07-09 | Johnson & Johnson | Druckempfindliche selbstklebende Folien und Baender |
| CH496791A (de) * | 1967-03-08 | 1970-09-30 | Geigy Ag J R | Klebstoffmassen |
| DE2436259A1 (de) * | 1974-07-27 | 1976-02-12 | Erdoelchemie Gmbh | Verfahren zur substanzpolymerisation von alpha-olefinen |
| US3954697A (en) * | 1975-03-31 | 1976-05-04 | Eastman Kodak Company | Poly(higher-1-olefin-co-propylene) copolymers as hot-melt, pressure-sensitive adhesives |
| US4071325A (en) * | 1976-08-16 | 1978-01-31 | National Distillers And Chemical Corporation | Ethylene polymerization reactor |
| US4178272A (en) * | 1977-03-02 | 1979-12-11 | Eastman Kodak Company | Hot-melt adhesvies for bonding polyethylene |
| US4288358A (en) * | 1979-08-30 | 1981-09-08 | Eastman Kodak Company | Blends of propylene/1-butene or 1-pentene/higher α-olefin copolymers, compatible tackifying resins and plasticizing oils useful as hot-melt, pressure-sensitive adhesives |
| US4482687A (en) * | 1979-10-26 | 1984-11-13 | Union Carbide Corporation | Preparation of low-density ethylene copolymers in fluid bed reactor |
| JPS57101A (en) * | 1980-06-04 | 1982-01-05 | Mitsui Petrochem Ind Ltd | Method and apparatus for polymerization |
| US4530914A (en) * | 1983-06-06 | 1985-07-23 | Exxon Research & Engineering Co. | Process and catalyst for producing polyethylene having a broad molecular weight distribution |
| US4792595A (en) * | 1983-06-15 | 1988-12-20 | Exxon Research & Engineering Co. | Narrow MWD alpha-olefin copolymers |
| US4808561A (en) * | 1985-06-21 | 1989-02-28 | Exxon Chemical Patents Inc. | Supported polymerization catalyst |
| US4892851A (en) * | 1988-07-15 | 1990-01-09 | Fina Technology, Inc. | Process and catalyst for producing syndiotactic polyolefins |
| US5436305A (en) * | 1991-05-09 | 1995-07-25 | Phillips Petroleum Company | Organometallic fluorenyl compounds, preparation, and use |
| US5296433A (en) * | 1992-04-14 | 1994-03-22 | Minnesota Mining And Manufacturing Company | Tris(pentafluorophenyl)borane complexes and catalysts derived therefrom |
| US5521263A (en) * | 1994-10-18 | 1996-05-28 | Eastman Chemical Company | Catalysts and synthesis of high molecular weight amorphous polyolefins and recovery thereof |
-
1996
- 1996-04-26 US US08/644,611 patent/US5644007A/en not_active Expired - Lifetime
- 1996-11-21 WO PCT/US1996/018776 patent/WO1997041162A1/en not_active Ceased
- 1996-11-21 CN CN96180267A patent/CN1217000A/zh active Pending
- 1996-11-21 KR KR1019980708564A patent/KR20000028539A/ko not_active Withdrawn
- 1996-11-21 JP JP53884897A patent/JP3856840B2/ja not_active Expired - Lifetime
- 1996-11-21 CA CA002253709A patent/CA2253709A1/en not_active Abandoned
- 1996-11-21 EP EP96942043A patent/EP0895515B1/en not_active Expired - Lifetime
- 1996-11-21 DE DE69610338T patent/DE69610338T2/de not_active Expired - Lifetime
- 1996-11-21 AU AU11222/97A patent/AU1122297A/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| JP3856840B2 (ja) | 2006-12-13 |
| DE69610338D1 (de) | 2000-10-19 |
| EP0895515A1 (en) | 1999-02-10 |
| KR20000028539A (ko) | 2000-05-25 |
| WO1997041162A1 (en) | 1997-11-06 |
| EP0895515B1 (en) | 2000-09-13 |
| DE69610338T2 (de) | 2001-05-31 |
| AU1122297A (en) | 1997-11-19 |
| CN1217000A (zh) | 1999-05-19 |
| US5644007A (en) | 1997-07-01 |
| JP2000509095A (ja) | 2000-07-18 |
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