CN1347429A - 在含水介质中用水溶性金属络合物和增溶剂制备一氧化碳共聚物的方法 - Google Patents

在含水介质中用水溶性金属络合物和增溶剂制备一氧化碳共聚物的方法 Download PDF

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Publication number: CN1347429A
Authority: CN; China
Prior art keywords: carbon atom; group; aryl; acid; alkyl
Prior art date: 1999-04-20
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.): Pending

Application number

CN 00806450

Other languages

English (en)

Chinese (zh)

Inventor

J·奎瑟

G·E·麦基

M·杰普拉格斯

E·林德纳

M·施密德

J·沃尔多

P·韦格纳

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

BASF SE

Original Assignee

BASF SE

Priority date (The priority date 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 date listed.)

1999-04-20

Filing date

2000-04-11

Publication date

2002-05-01

2000-04-11 Application filed by BASF SE filed Critical BASF SE

2002-05-01 Publication of CN1347429A publication Critical patent/CN1347429A/zh

Status Pending legal-status Critical Current

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229910052751 metal Inorganic materials 0.000 title claims abstract description 42
239000002184 metal Substances 0.000 title claims abstract description 32
239000002904 solvent Substances 0.000 title claims abstract description 26
229920001577 copolymer Polymers 0.000 title claims description 5
239000012736 aqueous medium Substances 0.000 title abstract 2
238000004519 manufacturing process Methods 0.000 title description 5
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 65
150000001875 compounds Chemical class 0.000 claims abstract description 52
229910002091 carbon monoxide Inorganic materials 0.000 claims abstract description 44
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims abstract description 43
238000000034 method Methods 0.000 claims abstract description 43
229920005603 alternating copolymer Polymers 0.000 claims abstract description 6
229910052799 carbon Inorganic materials 0.000 claims description 64
239000003446 ligand Substances 0.000 claims description 50
125000003118 aryl group Chemical group 0.000 claims description 34
239000002253 acid Substances 0.000 claims description 29
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 24
230000000737 periodic effect Effects 0.000 claims description 24
150000003254 radicals Chemical class 0.000 claims description 23
150000004696 coordination complex Chemical class 0.000 claims description 22
150000002500 ions Chemical class 0.000 claims description 21
125000002877 alkyl aryl group Chemical group 0.000 claims description 20
125000000524 functional group Chemical group 0.000 claims description 20
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
150000003839 salts Chemical class 0.000 claims description 18
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 17
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 17
125000004429 atom Chemical group 0.000 claims description 15
125000002843 carboxylic acid group Chemical group 0.000 claims description 14
238000002360 preparation method Methods 0.000 claims description 13
239000003995 emulsifying agent Substances 0.000 claims description 11
239000001257 hydrogen Substances 0.000 claims description 11
229910052739 hydrogen Inorganic materials 0.000 claims description 11
239000000463 material Substances 0.000 claims description 10
229910019142 PO4 Inorganic materials 0.000 claims description 9
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 9
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 9
239000010452 phosphate Substances 0.000 claims description 9
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
125000004122 cyclic group Chemical group 0.000 claims description 7
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 6
KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
239000002841 Lewis acid Substances 0.000 claims description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
150000007513 acids Chemical class 0.000 claims description 6
150000007517 lewis acids Chemical class 0.000 claims description 6
230000002378 acidificating effect Effects 0.000 claims description 5
125000000623 heterocyclic group Chemical group 0.000 claims description 5
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 4
230000007935 neutral effect Effects 0.000 claims description 4
229910021630 Antimony pentafluoride Inorganic materials 0.000 claims description 2
229910015900 BF3 Inorganic materials 0.000 claims description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 2
VBVBHWZYQGJZLR-UHFFFAOYSA-I antimony pentafluoride Chemical compound F[Sb](F)(F)(F)F VBVBHWZYQGJZLR-UHFFFAOYSA-I 0.000 claims description 2
230000000536 complexating effect Effects 0.000 claims 2
238000011177 media preparation Methods 0.000 claims 1
238000007334 copolymerization reaction Methods 0.000 abstract description 4
150000002440 hydroxy compounds Chemical class 0.000 abstract description 2
-1 amino, carboxyl Chemical group 0.000 description 53
NNOBHPBYUHDMQF-UHFFFAOYSA-N propylphosphine Chemical compound CCCP NNOBHPBYUHDMQF-UHFFFAOYSA-N 0.000 description 42
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 30
238000006243 chemical reaction Methods 0.000 description 29
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 23
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 18
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 18
239000000203 mixture Substances 0.000 description 18
150000001336 alkenes Chemical class 0.000 description 17
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
229920001470 polyketone Polymers 0.000 description 16
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
239000001294 propane Substances 0.000 description 15
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
238000002474 experimental method Methods 0.000 description 13
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 12
230000000694 effects Effects 0.000 description 12
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 11
239000000178 monomer Substances 0.000 description 11
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 11
239000004711 α-olefin Substances 0.000 description 11
QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 10
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 10
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 10
229910052757 nitrogen Inorganic materials 0.000 description 9
229920000642 polymer Polymers 0.000 description 9
238000006277 sulfonation reaction Methods 0.000 description 9
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 8
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 8
XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 8
125000001931 aliphatic group Chemical group 0.000 description 8
125000000217 alkyl group Chemical group 0.000 description 8
XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 8
239000003054 catalyst Substances 0.000 description 8
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
229910052698 phosphorus Inorganic materials 0.000 description 8
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 8
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 7
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 7
239000002585 base Substances 0.000 description 7
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
239000011574 phosphorus Substances 0.000 description 7
KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 6
BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 6
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
239000012190 activator Substances 0.000 description 6
125000001118 alkylidene group Chemical group 0.000 description 6
JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 6
239000000084 colloidal system Substances 0.000 description 6
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
238000006116 polymerization reaction Methods 0.000 description 6
230000001681 protective effect Effects 0.000 description 6
239000000126 substance Substances 0.000 description 6
229910052723 transition metal Inorganic materials 0.000 description 6
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 5
125000002091 cationic group Chemical group 0.000 description 5
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 5
150000003624 transition metals Chemical class 0.000 description 5
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 4
229910002651 NO3 Inorganic materials 0.000 description 4
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical group [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 4
229910052783 alkali metal Inorganic materials 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
125000005843 halogen group Chemical group 0.000 description 4
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
150000002431 hydrogen Chemical class 0.000 description 4
HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 4
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 4
125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
230000009467 reduction Effects 0.000 description 4
125000001424 substituent group Chemical group 0.000 description 4
239000000725 suspension Substances 0.000 description 4
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
239000005977 Ethylene Substances 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 3
239000004141 Sodium laurylsulphate Substances 0.000 description 3
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
229910000085 borane Inorganic materials 0.000 description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
238000001816 cooling Methods 0.000 description 3
150000001925 cycloalkenes Chemical class 0.000 description 3
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 3
239000012153 distilled water Substances 0.000 description 3
238000001035 drying Methods 0.000 description 3
230000002349 favourable effect Effects 0.000 description 3
125000004836 hexamethylene group Chemical class [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 3
TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 3
150000002825 nitriles Chemical class 0.000 description 3
125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 description 3
230000000269 nucleophilic effect Effects 0.000 description 3
229910052763 palladium Inorganic materials 0.000 description 3
VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 3
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
ONQDVAFWWYYXHM-UHFFFAOYSA-M potassium lauryl sulfate Chemical compound [K+].CCCCCCCCCCCCOS([O-])(=O)=O ONQDVAFWWYYXHM-UHFFFAOYSA-M 0.000 description 3
229910052709 silver Inorganic materials 0.000 description 3
239000011734 sodium Substances 0.000 description 3
235000019333 sodium laurylsulphate Nutrition 0.000 description 3
239000000243 solution Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 3
125000000008 (C1-C10) alkyl group Chemical group 0.000 description 2
VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 2
RILZRCJGXSFXNE-UHFFFAOYSA-N 2-[4-(trifluoromethoxy)phenyl]ethanol Chemical compound OCCC1=CC=C(OC(F)(F)F)C=C1 RILZRCJGXSFXNE-UHFFFAOYSA-N 0.000 description 2
QGHDLJAZIIFENW-UHFFFAOYSA-N 4-[1,1,1,3,3,3-hexafluoro-2-(4-hydroxy-3-prop-2-enylphenyl)propan-2-yl]-2-prop-2-enylphenol Chemical group C1=C(CC=C)C(O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(O)C(CC=C)=C1 QGHDLJAZIIFENW-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 2
239000004908 Emulsion polymer Substances 0.000 description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
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 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
239000002879 Lewis base Substances 0.000 description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 2
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
239000004372 Polyvinyl alcohol Substances 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
150000008055 alkyl aryl sulfonates Chemical group 0.000 description 2
XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 2
239000004411 aluminium Substances 0.000 description 2
229910052782 aluminium Inorganic materials 0.000 description 2
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
229910052787 antimony Inorganic materials 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
229910021538 borax Inorganic materials 0.000 description 2
BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
229960002798 cetrimide Drugs 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
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239000011737 fluorine Substances 0.000 description 2
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150000007527 lewis bases Chemical class 0.000 description 2
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125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 2
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150000003003 phosphines Chemical class 0.000 description 2
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229910000073 phosphorus hydride Inorganic materials 0.000 description 2
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239000011591 potassium Substances 0.000 description 2
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239000002243 precursor Substances 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
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239000004332 silver Substances 0.000 description 2
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239000000344 soap Substances 0.000 description 2
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238000004611 spectroscopical analysis Methods 0.000 description 2
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ZPQOPVIELGIULI-UHFFFAOYSA-N 1,3-dichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1 ZPQOPVIELGIULI-UHFFFAOYSA-N 0.000 description 1
UEMGWPRHOOEKTA-UHFFFAOYSA-N 1,3-difluorobenzene Chemical compound FC1=CC=CC(F)=C1 UEMGWPRHOOEKTA-UHFFFAOYSA-N 0.000 description 1
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239000005715 Fructose Substances 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
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238000005654 Michaelis-Arbuzov synthesis reaction Methods 0.000 description 1
KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
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239000004698 Polyethylene Substances 0.000 description 1
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WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
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230000003081 coactivator Effects 0.000 description 1
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229910052737 gold Inorganic materials 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
150000005826 halohydrocarbons Chemical class 0.000 description 1
125000001072 heteroaryl group Chemical group 0.000 description 1
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229910052742 iron Inorganic materials 0.000 description 1
230000001678 irradiating effect Effects 0.000 description 1
238000006317 isomerization reaction Methods 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
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150000002736 metal compounds Chemical class 0.000 description 1
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125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
238000002156 mixing Methods 0.000 description 1
238000000465 moulding Methods 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
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125000001624 naphthyl group Chemical group 0.000 description 1
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239000012299 nitrogen atmosphere Substances 0.000 description 1
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239000003960 organic solvent Substances 0.000 description 1
150000002902 organometallic compounds Chemical class 0.000 description 1
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239000001301 oxygen Substances 0.000 description 1
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
239000005022 packaging material Substances 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
TZMFJUDUGYTVRY-UHFFFAOYSA-N pentane-2,3-dione Chemical compound CCC(=O)C(C)=O TZMFJUDUGYTVRY-UHFFFAOYSA-N 0.000 description 1
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
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VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 1
125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
238000007348 radical reaction Methods 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
229910052703 rhodium Inorganic materials 0.000 description 1
239000010948 rhodium Substances 0.000 description 1
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
229910052707 ruthenium Inorganic materials 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
229910052710 silicon Inorganic materials 0.000 description 1
239000010703 silicon Substances 0.000 description 1
HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
229910001494 silver tetrafluoroborate Inorganic materials 0.000 description 1
WCGIGOVLOFXAMG-UHFFFAOYSA-N silver;trifluoromethanesulfonic acid Chemical compound [Ag].OS(=O)(=O)C(F)(F)F WCGIGOVLOFXAMG-UHFFFAOYSA-N 0.000 description 1
APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
229940080264 sodium dodecylbenzenesulfonate Drugs 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
MZSDGDXXBZSFTG-UHFFFAOYSA-M sodium;benzenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC=CC=C1 MZSDGDXXBZSFTG-UHFFFAOYSA-M 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
125000003107 substituted aryl group Chemical group 0.000 description 1
150000003871 sulfonates Chemical class 0.000 description 1
125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
238000001308 synthesis method Methods 0.000 description 1
238000010189 synthetic method Methods 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
239000011135 tin Substances 0.000 description 1
229910052718 tin Inorganic materials 0.000 description 1
150000003609 titanium compounds Chemical class 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
230000007704 transition Effects 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
229950000477 triflutate Drugs 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical compound C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-UHFFFAOYSA-N 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
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238000009736 wetting 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
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
- 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
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/10—Complexes comprising metals of Group I (IA or IB) as the central metal
- 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
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/20—Complexes comprising metals of Group II (IIA or IIB) as the central metal
- 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
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- 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
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/824—Palladium

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Chemical & Material Sciences (AREA)
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CN 00806450 1999-04-20 2000-04-11 在含水介质中用水溶性金属络合物和增溶剂制备一氧化碳共聚物的方法 Pending CN1347429A (zh)

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Application Number	Priority Date	Filing Date	Title
DE19917920.4		1999-04-20
DE1999117920 DE19917920A1 (de)	1999-04-20	1999-04-20	Verfahren zur Herstellung von Kohlenmonoxidcopolymeren in wässrigem Medium unter Verwendung wasserlöslicher Metallkomplexe und Lösungsvermittlern

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CN1347429A true CN1347429A (zh)	2002-05-01

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CN 00806450 Pending CN1347429A (zh)	1999-04-20	2000-04-11	在含水介质中用水溶性金属络合物和增溶剂制备一氧化碳共聚物的方法

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Country	Link
EP (1)	EP1171506A1 (de)
JP (1)	JP2002542355A (de)
CN (1)	CN1347429A (de)
AU (1)	AU3819900A (de)
BR (1)	BR0009386A (de)
DE (1)	DE19917920A1 (de)
WO (1)	WO2000063277A1 (de)

Cited By (1)

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CN110628015A (zh) *	2019-10-10	2019-12-31	黄河三角洲京博化工研究院有限公司	一种复配催化剂和聚酮的制备方法

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DE10061877A1 (de) *	2000-12-12	2002-06-13	Basf Ag	Verfahren zur Herstellung wässriger Copolymerisatdispersionen von Copolymerisaten aus Kohlenmonoxid und wenigstens einer olefinisch ungesättigten Verbindung
DE10125138A1 (de)	2001-05-22	2002-12-05	Basf Ag	Verfahren zur Herstellung von Copolymerisaten aus Kohlenmonoxid und einer olefinisch ungesättigten Verbindung in wässrigem Medium
DE10133042A1 (de) *	2001-07-11	2003-01-23	Basf Ag	Verfahren zur Herstellung wässriger Copolymerisatdispersionen von Copolymerisaten aus Kohlenmonoxid und olefinisch ungesättigten Verbindungen
DE10303312A1 (de) *	2003-01-28	2004-07-29	Basf Ag	Verfahren zur Herstellung wässriger Polymerisatdispersionen auf Basis von Olefinen durch metallkomplexkatalytische Polymersation
DE10322466A1 (de)	2003-05-16	2004-12-02	Basf Ag	Verfahren zur Herstellung wässriger Polymerisatdispersionen
DE10322787A1 (de)	2003-05-19	2004-12-09	Basf Ag	Verfahren zur Herstellung von Polymerpulvern
DE10326127A1 (de)	2003-06-06	2004-12-23	Basf Ag	Verfahren zur Herstellung einer wässrigen Polymerisatdispersion

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EP0605062B1 (de) *	1992-12-31	1999-07-14	Shell Internationale Researchmaatschappij B.V.	Herstellung von Copolymeren aus Kohlenmonoxid und ethylenisch ungesättigten Verbindungen
DE19816190A1 (de) *	1998-04-14	1999-10-21	Basf Ag	Cis-verbrückte Metallkomplexe sowie Katalysatorsysteme für die Herstellung von Copolymerisaten aus Kohlenmonoxid und olefinisch ungesättigten Verbindungen
DE19829519A1 (de) *	1998-07-02	2000-01-05	Basf Ag	Wasserlösliche Übergangsmetallkomplexe
DE19829520A1 (de) *	1998-07-02	2000-01-05	Basf Ag	Katalysatorsysteme auf der Basis von Übergangsmetallkomplexen für die Kohlenmonoxidcopolymerisation in einem wässrigen Medium
DE19830886A1 (de) *	1998-07-10	2000-01-13	Basf Ag	Wasserlösliche Übergangsmetallkomplexe

1999
- 1999-04-20 DE DE1999117920 patent/DE19917920A1/de not_active Withdrawn
2000
- 2000-04-11 EP EP00917073A patent/EP1171506A1/de not_active Withdrawn
- 2000-04-11 JP JP2000612361A patent/JP2002542355A/ja not_active Withdrawn
- 2000-04-11 BR BR0009386-6A patent/BR0009386A/pt not_active Application Discontinuation
- 2000-04-11 AU AU38199/00A patent/AU3819900A/en not_active Abandoned
- 2000-04-11 WO PCT/EP2000/003228 patent/WO2000063277A1/de not_active Application Discontinuation
- 2000-04-11 CN CN 00806450 patent/CN1347429A/zh active Pending

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN110628015A (zh) *	2019-10-10	2019-12-31	黄河三角洲京博化工研究院有限公司	一种复配催化剂和聚酮的制备方法

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DE19917920A1 (de)	2000-10-26
JP2002542355A (ja)	2002-12-10
BR0009386A (pt)	2002-01-08
AU3819900A (en)	2000-11-02
EP1171506A1 (de)	2002-01-16
WO2000063277A1 (de)	2000-10-26

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CN1347429A - 在含水介质中用水溶性金属络合物和增溶剂制备一氧化碳共聚物的方法 - Google Patents

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