CA2863836C - Procede de production de polyisobutylene de haut poids moleculaire - Google Patents
Procede de production de polyisobutylene de haut poids moleculaire Download PDFInfo
- Publication number
- CA2863836C CA2863836C CA2863836A CA2863836A CA2863836C CA 2863836 C CA2863836 C CA 2863836C CA 2863836 A CA2863836 A CA 2863836A CA 2863836 A CA2863836 A CA 2863836A CA 2863836 C CA2863836 C CA 2863836C
- Authority
- CA
- Canada
- Prior art keywords
- polymerization
- process according
- isobutene
- temperatures
- molecular weight
- 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.)
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- 238000004519 manufacturing process Methods 0.000 title claims description 8
- 229920002367 Polyisobutene Polymers 0.000 title description 12
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims abstract description 117
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 72
- 238000006243 chemical reaction Methods 0.000 claims abstract description 40
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 29
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 25
- 229920001519 homopolymer Polymers 0.000 claims abstract description 22
- 239000012442 inert solvent Substances 0.000 claims abstract description 20
- 239000002685 polymerization catalyst Substances 0.000 claims abstract description 17
- 239000002841 Lewis acid Substances 0.000 claims abstract description 13
- 150000007517 lewis acids Chemical class 0.000 claims abstract description 13
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 4
- 229930195734 saturated hydrocarbon Natural products 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 42
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 37
- 239000000203 mixture Substances 0.000 claims description 20
- 229910015900 BF3 Inorganic materials 0.000 claims description 18
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 14
- 229910052782 aluminium Inorganic materials 0.000 claims description 14
- -1 iron halides Chemical class 0.000 claims description 14
- 238000001816 cooling Methods 0.000 claims description 13
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 12
- FXNDIJDIPNCZQJ-UHFFFAOYSA-N 2,4,4-trimethylpent-1-ene Chemical compound CC(=C)CC(C)(C)C FXNDIJDIPNCZQJ-UHFFFAOYSA-N 0.000 claims description 9
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 8
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 claims description 8
- 238000000746 purification Methods 0.000 claims description 8
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 7
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 6
- 150000001299 aldehydes Chemical class 0.000 claims description 6
- 150000002576 ketones Chemical class 0.000 claims description 6
- 239000001294 propane Substances 0.000 claims description 6
- 150000001241 acetals Chemical class 0.000 claims description 5
- 150000002170 ethers Chemical class 0.000 claims description 5
- 150000002373 hemiacetals Chemical class 0.000 claims description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 5
- 229910052742 iron Inorganic materials 0.000 claims description 5
- 239000007791 liquid phase Substances 0.000 claims description 5
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims description 4
- 239000003999 initiator Substances 0.000 claims description 4
- 239000001282 iso-butane Substances 0.000 claims description 4
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims description 4
- 150000003460 sulfonic acids Chemical class 0.000 claims description 4
- QYSGYZVSCZSLHT-UHFFFAOYSA-N octafluoropropane Chemical compound FC(F)(F)C(F)(F)C(F)(F)F QYSGYZVSCZSLHT-UHFFFAOYSA-N 0.000 claims description 3
- 229960004065 perflutren Drugs 0.000 claims description 3
- YFMFNYKEUDLDTL-UHFFFAOYSA-N 1,1,1,2,3,3,3-heptafluoropropane Chemical compound FC(F)(F)C(F)C(F)(F)F YFMFNYKEUDLDTL-UHFFFAOYSA-N 0.000 claims description 2
- 150000001733 carboxylic acid esters Chemical group 0.000 claims description 2
- 125000001033 ether group Chemical group 0.000 claims description 2
- 150000002894 organic compounds Chemical class 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 abstract description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000000047 product Substances 0.000 description 17
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 16
- 239000007788 liquid Substances 0.000 description 14
- 229920000642 polymer Polymers 0.000 description 12
- 150000001298 alcohols Chemical class 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 239000003054 catalyst Substances 0.000 description 10
- 239000000178 monomer Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 239000002002 slurry Substances 0.000 description 7
- 239000004215 Carbon black (E152) Substances 0.000 description 6
- 238000007872 degassing Methods 0.000 description 5
- 239000012530 fluid Substances 0.000 description 5
- 238000010626 work up procedure Methods 0.000 description 5
- WGECXQBGLLYSFP-UHFFFAOYSA-N 2,3-dimethylpentane Chemical compound CCC(C)C(C)C WGECXQBGLLYSFP-UHFFFAOYSA-N 0.000 description 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 4
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- BZHMBWZPUJHVEE-UHFFFAOYSA-N 2,3-dimethylpentane Natural products CC(C)CC(C)C BZHMBWZPUJHVEE-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 229910000831 Steel Inorganic materials 0.000 description 3
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- 239000010959 steel Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- CTMHWPIWNRWQEG-UHFFFAOYSA-N 1-methylcyclohexene Chemical compound CC1=CCCCC1 CTMHWPIWNRWQEG-UHFFFAOYSA-N 0.000 description 2
- FLTJDUOFAQWHDF-UHFFFAOYSA-N 2,2-dimethylhexane Chemical compound CCCCC(C)(C)C FLTJDUOFAQWHDF-UHFFFAOYSA-N 0.000 description 2
- CXOWYJMDMMMMJO-UHFFFAOYSA-N 2,2-dimethylpentane Chemical compound CCCC(C)(C)C CXOWYJMDMMMMJO-UHFFFAOYSA-N 0.000 description 2
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical compound CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 2
- GXDHCNNESPLIKD-UHFFFAOYSA-N 2-methylhexane Chemical compound CCCCC(C)C GXDHCNNESPLIKD-UHFFFAOYSA-N 0.000 description 2
- KUMXLFIBWFCMOJ-UHFFFAOYSA-N 3,3-dimethylhexane Chemical compound CCCC(C)(C)CC KUMXLFIBWFCMOJ-UHFFFAOYSA-N 0.000 description 2
- LAIUFBWHERIJIH-UHFFFAOYSA-N 3-Methylheptane Chemical compound CCCCC(C)CC LAIUFBWHERIJIH-UHFFFAOYSA-N 0.000 description 2
- AORMDLNPRGXHHL-UHFFFAOYSA-N 3-ethylpentane Chemical compound CCC(CC)CC AORMDLNPRGXHHL-UHFFFAOYSA-N 0.000 description 2
- VLJXXKKOSFGPHI-UHFFFAOYSA-N 3-methylhexane Chemical compound CCCC(C)CC VLJXXKKOSFGPHI-UHFFFAOYSA-N 0.000 description 2
- PFEOZHBOMNWTJB-UHFFFAOYSA-N 3-methylpentane Chemical compound CCC(C)CC PFEOZHBOMNWTJB-UHFFFAOYSA-N 0.000 description 2
- CHBAWFGIXDBEBT-UHFFFAOYSA-N 4-methylheptane Chemical compound CCCC(C)CCC CHBAWFGIXDBEBT-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- 229930040373 Paraformaldehyde Natural products 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000012190 activator Substances 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- 238000010538 cationic polymerization reaction Methods 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 239000002826 coolant Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- RWRIWBAIICGTTQ-UHFFFAOYSA-N difluoromethane Chemical compound FCF RWRIWBAIICGTTQ-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000003701 inert diluent Substances 0.000 description 2
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 2
- 238000012423 maintenance Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229940050176 methyl chloride Drugs 0.000 description 2
- 229920002866 paraformaldehyde Polymers 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- JXPOLSKBTUYKJB-UHFFFAOYSA-N xi-2,3-Dimethylhexane Chemical compound CCCC(C)C(C)C JXPOLSKBTUYKJB-UHFFFAOYSA-N 0.000 description 2
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- FCBJLBCGHCTPAQ-UHFFFAOYSA-N 1-fluorobutane Chemical compound CCCCF FCBJLBCGHCTPAQ-UHFFFAOYSA-N 0.000 description 1
- JRHNUZCXXOTJCA-UHFFFAOYSA-N 1-fluoropropane Chemical compound CCCF JRHNUZCXXOTJCA-UHFFFAOYSA-N 0.000 description 1
- XTDQDBVBDLYELW-UHFFFAOYSA-N 2,2,3-trimethylpentane Chemical compound CCC(C)C(C)(C)C XTDQDBVBDLYELW-UHFFFAOYSA-N 0.000 description 1
- FOLREJCGDZQHJL-UHFFFAOYSA-N 2-methylbutane;propane Chemical compound CCC.CCC(C)C FOLREJCGDZQHJL-UHFFFAOYSA-N 0.000 description 1
- ZRNSSRODJSSVEJ-UHFFFAOYSA-N 2-methylpentacosane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCC(C)C ZRNSSRODJSSVEJ-UHFFFAOYSA-N 0.000 description 1
- SFRKSDZMZHIISH-UHFFFAOYSA-N 3-ethylhexane Chemical compound CCCC(CC)CC SFRKSDZMZHIISH-UHFFFAOYSA-N 0.000 description 1
- DFVOXRAAHOJJBN-UHFFFAOYSA-N 6-methylhept-1-ene Chemical compound CC(C)CCCC=C DFVOXRAAHOJJBN-UHFFFAOYSA-N 0.000 description 1
- KJQMOGOKAYDMOR-UHFFFAOYSA-N CC(=C)C=C.CC(=C)C=C Chemical compound CC(=C)C=C.CC(=C)C=C KJQMOGOKAYDMOR-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001348 alkyl chlorides Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical class CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001735 carboxylic acids Chemical class 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
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000004035 construction material Substances 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 150000001983 dialkylethers Chemical class 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- UHCBBWUQDAVSMS-UHFFFAOYSA-N fluoroethane Chemical compound CCF UHCBBWUQDAVSMS-UHFFFAOYSA-N 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 229940015043 glyoxal Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N monofluoromethane Natural products FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 238000013021 overheating Methods 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- YLQLIQIAXYRMDL-UHFFFAOYSA-N propylheptyl alcohol Chemical compound CCCCCC(CO)CCC YLQLIQIAXYRMDL-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 238000012958 reprocessing Methods 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-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
- C08F10/04—Monomers containing three or four carbon atoms
- C08F10/08—Butenes
- C08F10/10—Isobutene
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)
Abstract
L'invention concerne un procédé de production d'homopolymères d'isobutène de masse moléculaire moyenne en poids de 75.000 à 10.000.000 par polymérisation d'isobutène, comprenant les étapes consistant à : (a) effectuer la polymérisation à une température comprise entre -80°C et -190°C, (b) utiliser comme solvant inerte des hydrocarbures en C1- à C5- éventuellement halogénés, (c) introduire comme catalyseur de polymérisation un complexe de l'acide de Lewis (d) effectuer la polymérisation en présence d'au moins un accélérateur de réaction sous la forme d'un composé d'hydrocarbure éthyléniquement saturé, lequel contient un atome d'oxygène et est dépourvu de proton détachable, et effectuer la polymérisation en présence d'au moins un régulateur de longueur de chaîne, lequel contient un atome de carbone oléfinique tertiaire.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP12155872 | 2012-02-17 | ||
| EP12155872.0 | 2012-02-17 | ||
| PCT/EP2013/053042 WO2013120984A1 (fr) | 2012-02-17 | 2013-02-15 | Procédé de production de polyisobutylène de haut poids moléculaire |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2863836A1 CA2863836A1 (fr) | 2013-08-22 |
| CA2863836C true CA2863836C (fr) | 2020-06-30 |
Family
ID=47714125
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2863836A Active CA2863836C (fr) | 2012-02-17 | 2013-02-15 | Procede de production de polyisobutylene de haut poids moleculaire |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP2814851A1 (fr) |
| JP (2) | JP6234382B2 (fr) |
| KR (1) | KR101974337B1 (fr) |
| CN (1) | CN104136470B (fr) |
| CA (1) | CA2863836C (fr) |
| MY (1) | MY168940A (fr) |
| SG (2) | SG10201606861XA (fr) |
| WO (1) | WO2013120984A1 (fr) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9458262B2 (en) * | 2011-10-21 | 2016-10-04 | Basf Se | Process for preparing isobutene homopolymers or copolymers |
| WO2017011224A1 (fr) | 2015-07-10 | 2017-01-19 | Uop Llc | Procédés d'alkylation à l'aide de catalyseurs à acide de lewis liquide |
| CN107522816B (zh) * | 2017-09-26 | 2021-07-09 | 青岛瑞林材料科技有限公司 | 一种合成高顺式二烯烃聚合物的方法 |
| CN107522817A (zh) * | 2017-09-26 | 2017-12-29 | 青岛瑞林材料科技有限公司 | 一种高顺式聚二烯烃的制备方法 |
| CN107652381B (zh) * | 2017-09-26 | 2021-07-09 | 青岛瑞林材料科技有限公司 | 一种高顺式二烯烃聚合物的制备方法 |
| CN107501472A (zh) * | 2017-09-26 | 2017-12-22 | 青岛瑞林材料科技有限公司 | 一种高顺式二烯烃聚合物的合成方法 |
| CN107602747B (zh) * | 2017-09-26 | 2021-01-12 | 青岛瑞林材料科技有限公司 | 一种高顺式聚二烯烃的合成方法 |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB590595A (en) * | 1944-03-14 | 1947-07-23 | Standard Oil Dev Co | Improved process and apparatus for the polymerisation of iso-olefins |
| US2405480A (en) * | 1944-10-05 | 1946-08-06 | Standard Oil Dev Co | Polymerization process |
| US2559062A (en) * | 1945-11-27 | 1951-07-03 | Standard Oil Dev Co | Friedel-crafts metal halide-ether complexes as polymerization catalysts |
| US2585867A (en) * | 1948-03-05 | 1952-02-12 | Jasco Inc | Process for polymerizing isoolefins using methyl chloride solution of bf as catalyst |
| US2553426A (en) * | 1948-05-26 | 1951-05-15 | Standard Oil Dev Co | Method for terminating a low temperature polymerization process |
| DE2061289B2 (de) | 1970-12-12 | 1978-06-29 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Polymerisation von Isobutylen |
| FR2117121A5 (fr) * | 1970-12-12 | 1972-07-21 | Basf Ag | |
| SU478022A1 (ru) * | 1973-12-07 | 1975-07-25 | Предприятие П/Я А-7942 | Способ регулировани процесса низкотемпературной полимеризации изобутилена |
| DE3332629A1 (de) * | 1983-09-09 | 1985-03-28 | Hermann Berstorff Maschinenbau Gmbh, 3000 Hannover | Verfahren und vorrichtung zum pulverisieren von polymeren |
| DE3404764A1 (de) * | 1984-02-10 | 1985-08-14 | Basf Ag, 6700 Ludwigshafen | Verfahren zur polymerisation von isobutylen |
| US4946899A (en) * | 1988-12-16 | 1990-08-07 | The University Of Akron | Thermoplastic elastomers of isobutylene and process of preparation |
| WO2000011040A1 (fr) * | 1998-08-25 | 2000-03-02 | Nippon Petrochemicals Company, Limited | Procede de production de polymere butenique |
| CA2316741A1 (fr) * | 2000-08-24 | 2002-02-24 | Bayer Inc. | Butylcaoutchouc a transformabilite amelioree et methode de production |
| US7662900B2 (en) * | 2005-10-11 | 2010-02-16 | Basf Aktiengesellschaft | Method for producing polyisobutene |
| DE102005048698A1 (de) * | 2005-10-11 | 2007-04-12 | Basf Ag | Verfahren zur Herstellung von Polyisobuten |
| WO2007113196A1 (fr) | 2006-04-05 | 2007-10-11 | Basf Se | Procede de fabrication d'homopolymeres d'isobutene de masse moleculaire elevee par polymerisation dans un appareil presentant des proprietes de melange et de promotion |
| CN101602823B (zh) * | 2008-06-13 | 2011-04-20 | 中国石油化工股份有限公司 | 一种阳离子聚合引发体系及其应用 |
| EP2646478A2 (fr) | 2010-11-30 | 2013-10-09 | Basf Se | Préparation de dérivés d'homopolymères ou de copolymères d'isobutène |
-
2013
- 2013-02-15 EP EP13704127.3A patent/EP2814851A1/fr not_active Ceased
- 2013-02-15 WO PCT/EP2013/053042 patent/WO2013120984A1/fr active Application Filing
- 2013-02-15 JP JP2014557050A patent/JP6234382B2/ja active Active
- 2013-02-15 SG SG10201606861XA patent/SG10201606861XA/en unknown
- 2013-02-15 MY MYPI2014002038A patent/MY168940A/en unknown
- 2013-02-15 SG SG11201403863YA patent/SG11201403863YA/en unknown
- 2013-02-15 CA CA2863836A patent/CA2863836C/fr active Active
- 2013-02-15 CN CN201380009872.8A patent/CN104136470B/zh active Active
- 2013-02-15 KR KR1020147025472A patent/KR101974337B1/ko active IP Right Grant
-
2017
- 2017-07-21 JP JP2017141991A patent/JP2017186577A/ja not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| CA2863836A1 (fr) | 2013-08-22 |
| CN104136470B (zh) | 2016-08-24 |
| KR20140122757A (ko) | 2014-10-20 |
| EP2814851A1 (fr) | 2014-12-24 |
| JP2017186577A (ja) | 2017-10-12 |
| KR101974337B1 (ko) | 2019-05-02 |
| MY168940A (en) | 2019-01-10 |
| JP2015507069A (ja) | 2015-03-05 |
| CN104136470A (zh) | 2014-11-05 |
| SG11201403863YA (en) | 2014-10-30 |
| WO2013120984A1 (fr) | 2013-08-22 |
| SG10201606861XA (en) | 2016-10-28 |
| JP6234382B2 (ja) | 2017-11-22 |
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Effective date: 20180214 |