CA1318440C - Vapor phase process for polymerizing carbon monoxide and olefins - Google Patents
Vapor phase process for polymerizing carbon monoxide and olefinsInfo
- Publication number
- CA1318440C CA1318440C CA000537956A CA537956A CA1318440C CA 1318440 C CA1318440 C CA 1318440C CA 000537956 A CA000537956 A CA 000537956A CA 537956 A CA537956 A CA 537956A CA 1318440 C CA1318440 C CA 1318440C
- Authority
- CA
- Canada
- Prior art keywords
- catalyst composition
- component
- carbon monoxide
- polymerization
- palladium
- 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 - Fee Related
Links
- 229910002091 carbon monoxide Inorganic materials 0.000 title claims abstract description 57
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 title claims abstract description 55
- 238000000034 method Methods 0.000 title claims abstract description 47
- 150000001336 alkenes Chemical class 0.000 title abstract 2
- 230000000379 polymerizing effect Effects 0.000 title abstract 2
- 239000012808 vapor phase Substances 0.000 title abstract 2
- 239000000203 mixture Substances 0.000 claims abstract description 85
- 239000003054 catalyst Substances 0.000 claims abstract description 67
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 56
- 229920000642 polymer Polymers 0.000 claims abstract description 50
- 239000003085 diluting agent Substances 0.000 claims abstract description 19
- 239000002253 acid Substances 0.000 claims abstract description 18
- 238000002360 preparation method Methods 0.000 claims abstract description 18
- 239000007788 liquid Substances 0.000 claims abstract description 16
- 239000003446 ligand Substances 0.000 claims abstract description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
- 150000002894 organic compounds Chemical class 0.000 claims abstract description 8
- 150000002941 palladium compounds Chemical class 0.000 claims abstract description 8
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 6
- 239000011574 phosphorus Substances 0.000 claims abstract description 6
- 150000001450 anions Chemical class 0.000 claims abstract description 5
- 229910052787 antimony Chemical group 0.000 claims abstract description 5
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical group [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052785 arsenic Inorganic materials 0.000 claims abstract description 3
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical group [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 claims abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 51
- 229920001577 copolymer Polymers 0.000 claims description 48
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 38
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 27
- 239000012876 carrier material Substances 0.000 claims description 18
- 229910052763 palladium Inorganic materials 0.000 claims description 18
- 229920001897 terpolymer Polymers 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 13
- 229910052751 metal Inorganic materials 0.000 claims description 13
- 239000002184 metal Substances 0.000 claims description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 239000000178 monomer Substances 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 6
- LVEYOSJUKRVCCF-UHFFFAOYSA-N 1,3-bis(diphenylphosphino)propane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCP(C=1C=CC=CC=1)C1=CC=CC=C1 LVEYOSJUKRVCCF-UHFFFAOYSA-N 0.000 claims description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- -1 transition metal salt Chemical class 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 150000002430 hydrocarbons Chemical class 0.000 claims description 3
- ZSLUVFAKFWKJRC-IGMARMGPSA-N 232Th Chemical compound [232Th] ZSLUVFAKFWKJRC-IGMARMGPSA-N 0.000 claims description 2
- 229910052684 Cerium Inorganic materials 0.000 claims description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 claims description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 229910052776 Thorium Inorganic materials 0.000 claims description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 2
- 239000004411 aluminium Substances 0.000 claims description 2
- 229910052782 aluminium Inorganic materials 0.000 claims description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 2
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 claims description 2
- 229910052804 chromium Inorganic materials 0.000 claims description 2
- 239000011651 chromium Substances 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 239000010949 copper Substances 0.000 claims description 2
- 150000003983 crown ethers Chemical class 0.000 claims description 2
- 229910052733 gallium Inorganic materials 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- 229910052744 lithium Inorganic materials 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 229910052718 tin Inorganic materials 0.000 claims description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 2
- 229910052720 vanadium Inorganic materials 0.000 claims description 2
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 claims description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 2
- 229940005561 1,4-benzoquinone Drugs 0.000 claims 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 claims 1
- 244000046052 Phaseolus vulgaris Species 0.000 claims 1
- 150000001224 Uranium Chemical class 0.000 claims 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 159000000003 magnesium salts Chemical class 0.000 claims 1
- 229910052759 nickel Inorganic materials 0.000 claims 1
- 150000002940 palladium Chemical class 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims 1
- 229910052723 transition metal Inorganic materials 0.000 claims 1
- 229910052726 zirconium Inorganic materials 0.000 claims 1
- 238000012685 gas phase polymerization Methods 0.000 abstract description 10
- 239000007791 liquid phase Substances 0.000 abstract description 9
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract description 3
- 238000000746 purification Methods 0.000 abstract description 2
- 238000000926 separation method Methods 0.000 abstract description 2
- 238000006243 chemical reaction Methods 0.000 description 23
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 22
- 239000012071 phase Substances 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 229910052799 carbon Inorganic materials 0.000 description 12
- 239000007789 gas Substances 0.000 description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 11
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 10
- 239000000306 component Substances 0.000 description 9
- 238000001816 cooling Methods 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 150000002431 hydrogen Chemical class 0.000 description 6
- 150000002739 metals Chemical class 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 6
- 150000002500 ions Chemical class 0.000 description 5
- 239000001294 propane Substances 0.000 description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 3
- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000011835 investigation Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 2
- 102100024133 Coiled-coil domain-containing protein 50 Human genes 0.000 description 2
- 101000910772 Homo sapiens Coiled-coil domain-containing protein 50 Proteins 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- QIVUCLWGARAQIO-OLIXTKCUSA-N (3s)-n-[(3s,5s,6r)-6-methyl-2-oxo-1-(2,2,2-trifluoroethyl)-5-(2,3,6-trifluorophenyl)piperidin-3-yl]-2-oxospiro[1h-pyrrolo[2,3-b]pyridine-3,6'-5,7-dihydrocyclopenta[b]pyridine]-3'-carboxamide Chemical compound C1([C@H]2[C@H](N(C(=O)[C@@H](NC(=O)C=3C=C4C[C@]5(CC4=NC=3)C3=CC=CN=C3NC5=O)C2)CC(F)(F)F)C)=C(F)C=CC(F)=C1F QIVUCLWGARAQIO-OLIXTKCUSA-N 0.000 description 1
- 150000004057 1,4-benzoquinones Chemical class 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 229920000856 Amylose Polymers 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 229920008712 Copo Polymers 0.000 description 1
- 206010011416 Croup infectious Diseases 0.000 description 1
- 229920000858 Cyclodextrin Polymers 0.000 description 1
- 240000007175 Datura inoxia Species 0.000 description 1
- BHTWZQKERRCPRZ-RYRKJORJSA-N Estra-4,9-diene-3,17-dione Chemical compound C1CC(=O)C=C2CC[C@@H]([C@H]3[C@@](C)(C(CC3)=O)CC3)C3=C21 BHTWZQKERRCPRZ-RYRKJORJSA-N 0.000 description 1
- UOACKFBJUYNSLK-XRKIENNPSA-N Estradiol Cypionate Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H](C4=CC=C(O)C=C4CC3)CC[C@@]21C)C(=O)CCC1CCCC1 UOACKFBJUYNSLK-XRKIENNPSA-N 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 241000820057 Ithone Species 0.000 description 1
- 101100536883 Legionella pneumophila subsp. pneumophila (strain Philadelphia 1 / ATCC 33152 / DSM 7513) thi5 gene Proteins 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 101100240664 Schizosaccharomyces pombe (strain 972 / ATCC 24843) nmt1 gene Proteins 0.000 description 1
- 229920005654 Sephadex Polymers 0.000 description 1
- 229910052770 Uranium Inorganic materials 0.000 description 1
- 229910052768 actinide Inorganic materials 0.000 description 1
- 150000001255 actinides Chemical class 0.000 description 1
- RRSCGNXXNRAXJC-UHFFFAOYSA-N bis(4-methylphenyl)phosphane Chemical compound C1=CC(C)=CC=C1PC1=CC=C(C)C=C1 RRSCGNXXNRAXJC-UHFFFAOYSA-N 0.000 description 1
- MPMBRWOOISTHJV-UHFFFAOYSA-N but-1-enylbenzene Chemical compound CCC=CC1=CC=CC=C1 MPMBRWOOISTHJV-UHFFFAOYSA-N 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 201000010549 croup Diseases 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- PBWZKZYHONABLN-UHFFFAOYSA-N difluoroacetic acid Chemical compound OC(=O)C(F)F PBWZKZYHONABLN-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 229960004592 isopropanol Drugs 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 235000019988 mead Nutrition 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- 229940017219 methyl propionate Drugs 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- DNYWZCXLKNTFFI-UHFFFAOYSA-N uranium Chemical compound [U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U] DNYWZCXLKNTFFI-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G67/00—Macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing oxygen or oxygen and carbon, not provided for in groups C08G2/00 - C08G65/00
- C08G67/02—Copolymers of carbon monoxide and aliphatic unsaturated compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
- C08L77/10—Polyamides derived from aromatically bound amino and carboxyl groups of amino-carboxylic acids or of polyamines and polycarboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Polyethers (AREA)
- Graft Or Block Polymers (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Multicomponent Fibers (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL8601348 | 1986-05-27 | ||
| NL8601348 | 1986-05-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1318440C true CA1318440C (en) | 1993-05-25 |
Family
ID=19848074
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000537956A Expired - Fee Related CA1318440C (en) | 1986-05-27 | 1987-05-26 | Vapor phase process for polymerizing carbon monoxide and olefins |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US4778876A (instruction) |
| EP (1) | EP0248483B1 (instruction) |
| JP (1) | JPH0822915B2 (instruction) |
| KR (1) | KR970000486B1 (instruction) |
| CN (1) | CN1009652B (instruction) |
| AT (1) | ATE60066T1 (instruction) |
| AU (1) | AU592872B2 (instruction) |
| BR (1) | BR8702703A (instruction) |
| CA (1) | CA1318440C (instruction) |
| DE (1) | DE3767371D1 (instruction) |
| DK (1) | DK269787A (instruction) |
| ES (1) | ES2019619B3 (instruction) |
| FI (1) | FI90783C (instruction) |
| IE (1) | IE60363B1 (instruction) |
| IL (1) | IL82635A (instruction) |
| IN (1) | IN170625B (instruction) |
| MX (1) | MX170155B (instruction) |
| NO (1) | NO168253C (instruction) |
| NZ (1) | NZ220420A (instruction) |
| ZA (1) | ZA873726B (instruction) |
Families Citing this family (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4820802A (en) * | 1987-02-03 | 1989-04-11 | Shell Oil Company | Improved process of preparing carbon monoxide/olefin copolymer with ortho substituted phosphine catalyst composition. |
| US4855399A (en) * | 1987-02-26 | 1989-08-08 | Shell Oil Company | Carbon monoxide/olefin co-polymerization process with phosphino substituted sulfonic acid catalyst |
| AU612173B2 (en) * | 1987-08-28 | 1991-07-04 | Shell Internationale Research Maatschappij B.V. | Preparation of olefin/CO copolymers |
| NL8702317A (nl) * | 1987-09-29 | 1989-04-17 | Shell Int Research | Katalysatorcomposities. |
| DE3856134T2 (de) * | 1987-12-29 | 1998-06-10 | Shell Int Research | Polymere Polyalkohole |
| CA1325306C (en) * | 1987-12-29 | 1993-12-14 | Pui Kwan Wong | Polymeric polyketone derivatives |
| CA1338577C (en) * | 1988-04-27 | 1996-09-03 | Jacobus Adrianus Bakkum | Process for the preparation of polymers of carbon monoxide with unsaturated compounds |
| CA1338578C (en) * | 1988-04-29 | 1996-09-03 | Gerrit Gerardus Rosenbrand | Process for the preparation of polymers of carbon monoxide with unsaturated compounds |
| US4948870A (en) * | 1988-05-27 | 1990-08-14 | Shell Oil Company | Polymerization process |
| US4965341A (en) * | 1988-06-08 | 1990-10-23 | Shell Oil Company | Polymerization of co/olefin with catalyst comprising sulfur bidentate ligand |
| US5077384A (en) * | 1989-08-17 | 1991-12-31 | Shell Oil Company | Carbon monoxide/olefin copolymer having wide molecular weight distribution |
| NL8902934A (nl) * | 1989-11-28 | 1991-06-17 | Shell Int Research | Bereiding van polymeren. |
| NL9000398A (nl) * | 1990-02-20 | 1991-09-16 | Shell Int Research | Bereiding van polymeren |
| US5216120A (en) * | 1991-02-26 | 1993-06-01 | Shell Oil Company | Polymerization of co/olefin with catalyst comprising palladium compound, lewis acid and bronsted acid |
| US5245123A (en) * | 1991-02-26 | 1993-09-14 | Shell Oil Company | Vapor phase polymerization of co/olefin with palladium compound, lewis acid and bidentate ligand |
| US5227464A (en) * | 1991-03-21 | 1993-07-13 | Shell Oil Company | Gas phase polymerization of co/olefin with particular catalyst support |
| US5237047A (en) * | 1991-05-01 | 1993-08-17 | Shell Oil Company | Polymerization of co/olefin wth catalyst chemically bound to particles of support |
| US5210178A (en) * | 1991-06-27 | 1993-05-11 | Shell Oil Company | Gas phase polyketone polymer preparation with preliminary addition of water |
| US5225523A (en) * | 1991-07-02 | 1993-07-06 | Shell Oil Company | Polyketone polymer preparation with tetra alkyl bis phosphine ligand and hydrogen |
| US5247064A (en) * | 1991-08-06 | 1993-09-21 | Shell Oil Company | Polymerization of co/olefin with p bidentate ligand |
| US5243026A (en) * | 1991-09-27 | 1993-09-07 | Shell Oil Company | Continuous gas phase polymerization of co/olefin with palladium and metal fluoride lewis acid catalyst |
| US5227437A (en) * | 1991-10-15 | 1993-07-13 | Shell Oil Company | Isomorphic polyketone polymer blend |
| US5644023A (en) * | 1992-04-21 | 1997-07-01 | Union Carbide Chemicals & Plastics Technology Corporation | Process for the manufacture of copolymers of ethylene and carbon monoxide |
| EP0572087A1 (en) * | 1992-05-27 | 1993-12-01 | Shell Internationale Researchmaatschappij B.V. | Process for the preparation of polymers of carbon monoxyde and olefinically unsaturated compounds |
| MX9303038A (es) * | 1992-05-27 | 1994-05-31 | Shell Int Research | Proceso para la preparacion de copolimeros de monoxido de carbono y compuestos etilenicamente insaturados. |
| JPH08501327A (ja) * | 1992-06-15 | 1996-02-13 | アクゾ ノーベル ナムローゼ フェンノートシャップ | ポリケトン類を製造するための改良された気相法 |
| US5552218A (en) * | 1992-06-26 | 1996-09-03 | Akzo Nobel N.V. | Polyketone yarn and a method of manufacturing same |
| TW305850B (instruction) * | 1992-11-17 | 1997-05-21 | Shell Int Research | |
| TW305849B (instruction) * | 1992-11-20 | 1997-05-21 | Shell Int Research | |
| US5820806A (en) * | 1993-01-13 | 1998-10-13 | Akzo Nobel Nv | Process for the preparation of polyketone fibers |
| EP0614928B1 (en) * | 1993-03-12 | 2000-02-02 | Shell Internationale Researchmaatschappij B.V. | Process for the preparation of copolymers of carbon monoxide and ethylenically unsaturated compounds |
| DE69422840T2 (de) * | 1993-03-12 | 2000-07-27 | Shell Internationale Research Maatschappij B.V., Den Haag/S'gravenhage | Verfahren zur Herstellung von Copolymeren aus Kohlenmonoxid und ethylenisch ungesättigten Verbindungen |
| ZA953387B (en) * | 1994-04-29 | 1995-11-29 | Shell Int Research | Catalyst system and process for the preparation of copolymers of carbon monoxide and olefinically unsaturated compounds |
| US5440010A (en) * | 1994-06-27 | 1995-08-08 | Akzo Nobel N.V. | Gas phase process for forming polyketones |
| EP0702045A3 (en) * | 1994-09-15 | 1996-07-17 | Shell Int Research | Gas phase process for the copolymerization of carbon monoxide and ethylenically unsaturated compounds |
| DE19746279A1 (de) * | 1997-10-20 | 1999-04-22 | Basf Ag | Verfahren zur heterogen-katalytischen Herstellung von Kohlenmonoxidcopolymeren |
| EP1055021B1 (en) | 1998-02-12 | 2004-02-04 | Acordis Industrial Fibers BV | Process for preparing polyketone fibres |
| US6548708B1 (en) | 1998-08-05 | 2003-04-15 | Sri International | Preparation of biphosphine ligands for incorporation into catalytic complexes |
| US6037442A (en) * | 1998-12-10 | 2000-03-14 | E. I. Du Pont De Nemours And Company | Preparation of olefin copolymers of sulfur dioxide or carbon monoxide |
| CN109312145B (zh) * | 2016-08-19 | 2021-03-16 | 亚洲大学校产学协力团 | 用于制备聚酮化合物的催化剂组合物、钯混合催化剂体系、利用其的聚酮化合物制备方法及聚酮聚合物 |
| CN108906021B (zh) * | 2018-06-01 | 2021-05-18 | 浙江利欧环保科技有限公司 | 一种钍掺杂硅藻土负载对甲苯磺酸催化剂及其制备方法和应用 |
| CN112142956B (zh) * | 2020-09-27 | 2021-10-19 | 中国科学院物理研究所 | 一种一氧化碳的聚合方法 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1129551A (en) * | 1965-03-18 | 1968-10-09 | Ici Ltd | Process for the manufacture of urethanes |
| GB1081304A (en) * | 1965-03-23 | 1967-08-31 | Ici Ltd | Improvements in or relating to chemical compounds |
| US3689460A (en) * | 1971-03-04 | 1972-09-05 | Shell Oil Co | Interpolymers of carbon monoxide and process for preparing same |
| US3694412A (en) * | 1971-03-04 | 1972-09-26 | Shell Oil Co | Process for preparing interpolymers of carbon monoxide in the presence of aryl phosphine-palladium halide complex |
| CA1019637A (en) * | 1972-05-09 | 1977-10-25 | Dahlgren Manufacturing Company | Method and apparatus for inking printing plates |
| US3914391A (en) * | 1973-03-26 | 1975-10-21 | Shell Oil Co | Preparation of HPd(CN){HD 3{B |
| US3835123A (en) * | 1973-03-26 | 1974-09-10 | Shell Oil Co | Process for preparing interpolymers of carbon monoxide and ethylenically unsaturated compounds |
| US3984388A (en) * | 1975-06-02 | 1976-10-05 | Shell Oil Company | Process to prepare polyketones |
| US4076911A (en) * | 1975-11-05 | 1978-02-28 | Union Oil Company Of California | Ethylene-carbon monoxide copolymers |
| GB2058074B (en) * | 1979-08-23 | 1983-10-12 | Secr Defence | Palladium complexes |
| EP0086281B2 (en) * | 1981-12-02 | 1988-10-19 | Shell Internationale Researchmaatschappij B.V. | Preparation of carbamates using a palladium-containing catalyst |
| DE3480845D1 (de) * | 1983-04-06 | 1990-02-01 | Shell Int Research | Verfahren zur herstellung von polyketonen. |
| NL8403035A (nl) * | 1984-10-05 | 1986-05-01 | Shell Int Research | Werkwijze ter bereiding van polyketonen. |
| IN168056B (instruction) * | 1986-03-05 | 1991-01-26 | Shell Int Research | |
| IN168306B (instruction) * | 1986-03-05 | 1991-03-09 | Shell Int Research |
-
1987
- 1987-05-20 IE IE132887A patent/IE60363B1/en not_active IP Right Cessation
- 1987-05-22 IL IL82635A patent/IL82635A/xx unknown
- 1987-05-22 IN IN446/DEL/87A patent/IN170625B/en unknown
- 1987-05-25 NZ NZ220420A patent/NZ220420A/xx unknown
- 1987-05-25 ZA ZA873726A patent/ZA873726B/xx unknown
- 1987-05-25 FI FI872297A patent/FI90783C/fi not_active IP Right Cessation
- 1987-05-26 EP EP87201001A patent/EP0248483B1/en not_active Expired - Lifetime
- 1987-05-26 DE DE8787201001T patent/DE3767371D1/de not_active Expired - Lifetime
- 1987-05-26 DK DK269787A patent/DK269787A/da not_active Application Discontinuation
- 1987-05-26 US US07/053,780 patent/US4778876A/en not_active Expired - Lifetime
- 1987-05-26 BR BR8702703A patent/BR8702703A/pt not_active Application Discontinuation
- 1987-05-26 CA CA000537956A patent/CA1318440C/en not_active Expired - Fee Related
- 1987-05-26 ES ES87201001T patent/ES2019619B3/es not_active Expired - Lifetime
- 1987-05-26 CN CN87104681A patent/CN1009652B/zh not_active Expired
- 1987-05-26 NO NO872209A patent/NO168253C/no unknown
- 1987-05-26 AU AU73406/87A patent/AU592872B2/en not_active Ceased
- 1987-05-26 AT AT87201001T patent/ATE60066T1/de not_active IP Right Cessation
- 1987-05-27 JP JP62128554A patent/JPH0822915B2/ja not_active Expired - Lifetime
- 1987-05-27 KR KR1019870005349A patent/KR970000486B1/ko not_active Expired - Fee Related
- 1987-05-27 MX MX006660A patent/MX170155B/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ATE60066T1 (de) | 1991-02-15 |
| CN1009652B (zh) | 1990-09-19 |
| IN170625B (instruction) | 1992-04-25 |
| NZ220420A (en) | 1989-06-28 |
| ZA873726B (en) | 1988-08-31 |
| ES2019619B3 (es) | 1991-07-01 |
| IE60363B1 (en) | 1994-07-13 |
| FI90783B (fi) | 1993-12-15 |
| KR970000486B1 (ko) | 1997-01-13 |
| DK269787D0 (da) | 1987-05-26 |
| EP0248483A3 (en) | 1988-03-16 |
| KR870011169A (ko) | 1987-12-21 |
| JPH0822915B2 (ja) | 1996-03-06 |
| EP0248483B1 (en) | 1991-01-16 |
| CN87104681A (zh) | 1987-12-23 |
| NO872209L (no) | 1987-11-30 |
| AU7340687A (en) | 1987-12-03 |
| NO168253C (no) | 1992-01-29 |
| EP0248483A2 (en) | 1987-12-09 |
| FI90783C (fi) | 1994-03-25 |
| AU592872B2 (en) | 1990-01-25 |
| DE3767371D1 (de) | 1991-02-21 |
| BR8702703A (pt) | 1988-03-01 |
| MX170155B (es) | 1993-08-10 |
| NO168253B (no) | 1991-10-21 |
| FI872297L (fi) | 1987-11-28 |
| IL82635A0 (en) | 1987-11-30 |
| JPS62285919A (ja) | 1987-12-11 |
| IL82635A (en) | 1991-03-10 |
| DK269787A (da) | 1987-11-28 |
| IE871328L (en) | 1987-11-27 |
| FI872297A0 (fi) | 1987-05-25 |
| US4778876A (en) | 1988-10-18 |
| NO872209D0 (no) | 1987-05-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1318440C (en) | Vapor phase process for polymerizing carbon monoxide and olefins | |
| EP0305011B1 (en) | Preparation of olefin/CO copolymers | |
| EP0213671B1 (en) | New polymers of carbon monoxide and ethene | |
| CA1271877A (en) | Polymer preparation | |
| KR960009687B1 (ko) | 신규 촉매 조성물 | |
| CA1324456C (en) | Catalyst compositions | |
| CA1305695C (en) | Catalyst compositions and process for olefin/co copolymerization | |
| US4940776A (en) | Catalytic polymerization of carbon monoxide/olefin in the presence of insoluble particulate solid matter | |
| EP0253416A1 (en) | Catalyst compositions | |
| CA1338576C (en) | Polyketone polymer preparation | |
| US5041530A (en) | Linear copolymer of co/olefin having spiro ketal units | |
| EP0262745B1 (en) | Polymer preparation | |
| CA1316624C (en) | Polymers | |
| CA1338582C (en) | Process for the preparation of polymers | |
| EP0280380A2 (en) | Catalyst compositions and process for copolymerizing Co with one or more olefinically unsaturated compounds | |
| CA1338578C (en) | Process for the preparation of polymers of carbon monoxide with unsaturated compounds | |
| CA2043513A1 (en) | Preparation of polymers of carbon monoxide with olefinically unsaturated compounds | |
| CA2014627A1 (en) | Preparation of copolymers of carbon monoxide | |
| AU682327B2 (en) | Preparation of copolymers of carbon monoxide and olefinically unsaturated compounds | |
| CA2061720A1 (en) | Catalyst compositions | |
| CA2063481A1 (en) | Catalyst compositions | |
| CA2029788A1 (en) | Preparation of polymers of carbon monoxide with unsaturated compounds | |
| EP0360359A1 (en) | Preparation of catalyst solution | |
| US5010170A (en) | Polymerization of carbon monoxide/olefin with at least one tetra aryl diphosphine ligand | |
| US5001221A (en) | Polymerization of carbon monoxide/olefin with catalyst/diluent recycle |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKLA | Lapsed |