TWI227248B - Double metal cyanide catalysts for preparing polyetherpolyols - Google Patents
Double metal cyanide catalysts for preparing polyetherpolyols Download PDFInfo
- Publication number
- TWI227248B TWI227248B TW089102360A TW89102360A TWI227248B TW I227248 B TWI227248 B TW I227248B TW 089102360 A TW089102360 A TW 089102360A TW 89102360 A TW89102360 A TW 89102360A TW I227248 B TWI227248 B TW I227248B
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- Prior art keywords
- acid
- catalyst
- scope
- patent application
- metal cyanide
- Prior art date
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- 239000003054 catalyst Substances 0.000 title claims abstract description 73
- 229910052751 metal Inorganic materials 0.000 title claims abstract description 40
- 239000002184 metal Substances 0.000 title claims abstract description 40
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 title claims abstract description 6
- 150000003839 salts Chemical class 0.000 claims abstract description 31
- 239000003613 bile acid Substances 0.000 claims abstract description 28
- 150000002148 esters Chemical class 0.000 claims abstract description 20
- 239000007858 starting material Substances 0.000 claims abstract description 12
- 239000003446 ligand Substances 0.000 claims abstract description 11
- 150000002825 nitriles Chemical class 0.000 claims abstract description 11
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
- 229920000570 polyether Polymers 0.000 claims description 27
- 239000002253 acid Substances 0.000 claims description 26
- 229920005862 polyol Polymers 0.000 claims description 26
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 24
- 150000003077 polyols Chemical class 0.000 claims description 24
- KXGVEGMKQFWNSR-UHFFFAOYSA-N deoxycholic acid Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 KXGVEGMKQFWNSR-UHFFFAOYSA-N 0.000 claims description 20
- 150000001409 amidines Chemical class 0.000 claims description 15
- -1 cyanide compound Chemical class 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 15
- HSINOMROUCMIEA-FGVHQWLLSA-N (2s,4r)-4-[(3r,5s,6r,7r,8s,9s,10s,13r,14s,17r)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-methylpentanoic acid Chemical compound C([C@@]12C)C[C@@H](O)C[C@H]1[C@@H](CC)[C@@H](O)[C@@H]1[C@@H]2CC[C@]2(C)[C@@H]([C@H](C)C[C@H](C)C(O)=O)CC[C@H]21 HSINOMROUCMIEA-FGVHQWLLSA-N 0.000 claims description 14
- BHQCQFFYRZLCQQ-OELDTZBJSA-N cholic acid Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 BHQCQFFYRZLCQQ-OELDTZBJSA-N 0.000 claims description 14
- KXGVEGMKQFWNSR-LLQZFEROSA-N deoxycholic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 KXGVEGMKQFWNSR-LLQZFEROSA-N 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- BHQCQFFYRZLCQQ-UHFFFAOYSA-N (3alpha,5alpha,7alpha,12alpha)-3,7,12-trihydroxy-cholan-24-oic acid Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 BHQCQFFYRZLCQQ-UHFFFAOYSA-N 0.000 claims description 12
- 239000004380 Cholic acid Substances 0.000 claims description 12
- 229960002471 cholic acid Drugs 0.000 claims description 12
- 235000019416 cholic acid Nutrition 0.000 claims description 12
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- 238000000034 method Methods 0.000 claims description 12
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 11
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 10
- 239000007864 aqueous solution Substances 0.000 claims description 9
- 238000012644 addition polymerization Methods 0.000 claims description 8
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 7
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- 229910052725 zinc Inorganic materials 0.000 claims description 6
- RUDATBOHQWOJDD-UHFFFAOYSA-N (3beta,5beta,7alpha)-3,7-Dihydroxycholan-24-oic acid Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)CC2 RUDATBOHQWOJDD-UHFFFAOYSA-N 0.000 claims description 5
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- RUDATBOHQWOJDD-BSWAIDMHSA-N chenodeoxycholic acid Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)CC1 RUDATBOHQWOJDD-BSWAIDMHSA-N 0.000 claims description 5
- 229960001091 chenodeoxycholic acid Drugs 0.000 claims description 5
- 230000002079 cooperative effect Effects 0.000 claims description 5
- 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 description 4
- SMEROWZSTRWXGI-UHFFFAOYSA-N Lithocholsaeure Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)CC2 SMEROWZSTRWXGI-UHFFFAOYSA-N 0.000 claims description 4
- SMEROWZSTRWXGI-HVATVPOCSA-N lithocholic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)CC1 SMEROWZSTRWXGI-HVATVPOCSA-N 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- AWDRATDZQPNJFN-VAYUFCLWSA-N taurodeoxycholic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(=O)NCCS(O)(=O)=O)C)[C@@]2(C)[C@@H](O)C1 AWDRATDZQPNJFN-VAYUFCLWSA-N 0.000 claims description 3
- WBWWGRHZICKQGZ-UHFFFAOYSA-N Taurocholic acid Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(=O)NCCS(O)(=O)=O)C)C1(C)C(O)C2 WBWWGRHZICKQGZ-UHFFFAOYSA-N 0.000 claims description 2
- WBWWGRHZICKQGZ-GIHLXUJPSA-N taurocholic acid Chemical compound C([C@@H]1C[C@H]2O)[C@@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@@H]([C@@H](CCC(=O)NCCS(O)(=O)=O)C)[C@@]2(C)[C@H](O)C1 WBWWGRHZICKQGZ-GIHLXUJPSA-N 0.000 claims description 2
- 241000272814 Anser sp. Species 0.000 claims 1
- 238000006392 deoxygenation reaction Methods 0.000 claims 1
- OBTSLRFPKIKXSZ-UHFFFAOYSA-N lithium potassium Chemical class [Li].[K] OBTSLRFPKIKXSZ-UHFFFAOYSA-N 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 13
- 230000000694 effects Effects 0.000 abstract description 10
- 150000001408 amides Chemical class 0.000 abstract 1
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- 239000012153 distilled water Substances 0.000 description 8
- 159000000000 sodium salts Chemical class 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 238000011049 filling Methods 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 230000006698 induction Effects 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 6
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- 229910052700 potassium Inorganic materials 0.000 description 6
- 239000011591 potassium Substances 0.000 description 6
- 229910052742 iron Inorganic materials 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 238000004140 cleaning Methods 0.000 description 4
- XLJKHNWPARRRJB-UHFFFAOYSA-N cobalt(2+) Chemical compound [Co+2] XLJKHNWPARRRJB-UHFFFAOYSA-N 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- 229920002635 polyurethane Polymers 0.000 description 4
- 239000004814 polyurethane Substances 0.000 description 4
- 239000011592 zinc chloride Substances 0.000 description 4
- 235000005074 zinc chloride Nutrition 0.000 description 4
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 3
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- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
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- 125000000217 alkyl group Chemical group 0.000 description 3
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- 229910052804 chromium Inorganic materials 0.000 description 3
- 239000011651 chromium Substances 0.000 description 3
- RKBAPHPQTADBIK-UHFFFAOYSA-N cobalt;hexacyanide Chemical compound [Co].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] RKBAPHPQTADBIK-UHFFFAOYSA-N 0.000 description 3
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- 238000000605 extraction Methods 0.000 description 3
- 150000004679 hydroxides Chemical class 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000012266 salt solution Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 238000002411 thermogravimetry Methods 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- WAEMQWOKJMHJLA-UHFFFAOYSA-N Manganese(2+) Chemical compound [Mn+2] WAEMQWOKJMHJLA-UHFFFAOYSA-N 0.000 description 2
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 2
- 229910002651 NO3 Inorganic materials 0.000 description 2
- VEQPNABPJHWNSG-UHFFFAOYSA-N Nickel(2+) Chemical compound [Ni+2] VEQPNABPJHWNSG-UHFFFAOYSA-N 0.000 description 2
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- 229910006069 SO3H Inorganic materials 0.000 description 2
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- 150000001450 anions Chemical class 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 229940099352 cholate Drugs 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 150000001913 cyanates Chemical class 0.000 description 2
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- WUWHFEHKUQVYLF-UHFFFAOYSA-M sodium;2-aminoacetate Chemical compound [Na+].NCC([O-])=O WUWHFEHKUQVYLF-UHFFFAOYSA-M 0.000 description 2
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- AWDBHOZBRXWRKS-UHFFFAOYSA-N tetrapotassium;iron(6+);hexacyanide Chemical compound [K+].[K+].[K+].[K+].[Fe+6].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] AWDBHOZBRXWRKS-UHFFFAOYSA-N 0.000 description 2
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- DLYVTEULDNMQAR-SRNOMOOLSA-N Cholic Acid Methyl Ester Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@H](C)CCC(=O)OC)[C@@]2(C)[C@@H](O)C1 DLYVTEULDNMQAR-SRNOMOOLSA-N 0.000 description 1
- 229910021580 Cobalt(II) chloride Inorganic materials 0.000 description 1
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- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000002309 gasification Methods 0.000 description 1
- 239000004247 glycine and its sodium salt Substances 0.000 description 1
- 235000013905 glycine and its sodium salt Nutrition 0.000 description 1
- 150000002344 gold compounds Chemical class 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000005181 hydroxyalkylaminoalkyl group Chemical group 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
- GYCHYNMREWYSKH-UHFFFAOYSA-L iron(ii) bromide Chemical compound [Fe+2].[Br-].[Br-] GYCHYNMREWYSKH-UHFFFAOYSA-L 0.000 description 1
- MMIPFLVOWGHZQD-UHFFFAOYSA-N manganese(3+) Chemical compound [Mn+3] MMIPFLVOWGHZQD-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 230000036284 oxygen consumption Effects 0.000 description 1
- 238000002161 passivation Methods 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229960003975 potassium Drugs 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Substances CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- YAYGSLOSTXKUBW-UHFFFAOYSA-N ruthenium(2+) Chemical compound [Ru+2] YAYGSLOSTXKUBW-UHFFFAOYSA-N 0.000 description 1
- NRHMKIHPTBHXPF-TUJRSCDTSA-M sodium cholate Chemical compound [Na+].C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC([O-])=O)C)[C@@]2(C)[C@@H](O)C1 NRHMKIHPTBHXPF-TUJRSCDTSA-M 0.000 description 1
- 229940029258 sodium glycinate Drugs 0.000 description 1
- JAJWGJBVLPIOOH-IZYKLYLVSA-M sodium taurocholate Chemical compound [Na+].C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(=O)NCCS([O-])(=O)=O)C)[C@@]2(C)[C@@H](O)C1 JAJWGJBVLPIOOH-IZYKLYLVSA-M 0.000 description 1
- 229940045946 sodium taurodeoxycholate Drugs 0.000 description 1
- WDFRNBJHDMUMBL-OICFXQLMSA-M sodium;(4r)-4-[(3r,5s,7r,8r,9s,10s,13r,14s,17r)-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]pentanoate Chemical compound [Na+].C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC([O-])=O)C)[C@@]2(C)CC1 WDFRNBJHDMUMBL-OICFXQLMSA-M 0.000 description 1
- YXHRQQJFKOHLAP-FVCKGWAHSA-M sodium;2-[[(4r)-4-[(3r,5r,8r,9s,10s,12s,13r,14s,17r)-3,12-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]ethanesulfonate Chemical compound [Na+].C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(=O)NCCS([O-])(=O)=O)C)[C@@]2(C)[C@@H](O)C1 YXHRQQJFKOHLAP-FVCKGWAHSA-M 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- PWYYWQHXAPXYMF-UHFFFAOYSA-N strontium(2+) Chemical compound [Sr+2] PWYYWQHXAPXYMF-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 229940045948 taurine deoxycholate Drugs 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- JDLYKQWJXAQNNS-UHFFFAOYSA-L zinc;dibenzoate Chemical compound [Zn+2].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 JDLYKQWJXAQNNS-UHFFFAOYSA-L 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
- C08G65/06—Cyclic ethers having no atoms other than carbon and hydrogen outside the ring
- C08G65/08—Saturated oxiranes
- C08G65/10—Saturated oxiranes characterised by the catalysts used
-
- 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
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/24—Nitrogen compounds
- B01J27/26—Cyanides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/06—Cobalt compounds
- C07F15/065—Cobalt compounds without a metal-carbon linkage
-
- 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2642—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds characterised by the catalyst used
- C08G65/2645—Metals or compounds thereof, e.g. salts
- C08G65/2663—Metal cyanide catalysts, i.e. DMC's
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Toxicology (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Catalysts (AREA)
- Polyethers (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Investigating Or Analysing Materials By Optical Means (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19905611A DE19905611A1 (de) | 1999-02-11 | 1999-02-11 | Doppelmetallcyanid-Katalysatoren für die Herstellung von Polyetherpolyolen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TWI227248B true TWI227248B (en) | 2005-02-01 |
Family
ID=7897114
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW089102360A TWI227248B (en) | 1999-02-11 | 2000-02-11 | Double metal cyanide catalysts for preparing polyetherpolyols |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US7008900B1 (https=) |
| EP (1) | EP1165657B1 (https=) |
| JP (1) | JP4523170B2 (https=) |
| KR (1) | KR100599355B1 (https=) |
| CN (1) | CN1138811C (https=) |
| AT (1) | ATE273340T1 (https=) |
| AU (1) | AU2294300A (https=) |
| BR (1) | BR0008106B1 (https=) |
| CA (1) | CA2362503C (https=) |
| CZ (1) | CZ296405B6 (https=) |
| DE (2) | DE19905611A1 (https=) |
| ES (1) | ES2226774T3 (https=) |
| HK (1) | HK1044959B (https=) |
| HU (1) | HUP0200197A3 (https=) |
| ID (1) | ID30028A (https=) |
| PL (1) | PL349858A1 (https=) |
| PT (1) | PT1165657E (https=) |
| RU (1) | RU2235589C2 (https=) |
| TW (1) | TWI227248B (https=) |
| WO (1) | WO2000047649A1 (https=) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| DE19953546A1 (de) | 1999-11-08 | 2001-05-10 | Bayer Ag | Doppelmetallcyanid-Katalysatoren für die Herstellung von Polyetherpolyolen |
| AU2001260217A1 (en) | 2000-04-20 | 2001-11-07 | Bayer Aktiengesellschaft | Method for producing double metal cyanide (dmc) catalysts |
| US6833431B2 (en) | 2001-05-02 | 2004-12-21 | Bayer Aktiengesellschaft | Double-metal cyanide catalysts for preparing polyether polyols |
| DE10121312A1 (de) * | 2001-05-02 | 2002-11-07 | Bayer Ag | Doppelmetallcyanid-Katalysatoren für die Herstellung von Polyetherpolyolen |
| DE10138216A1 (de) | 2001-08-03 | 2003-02-20 | Bayer Ag | Aliphatische Polycarbonathomo- und -copolymere durch DMC-Katalyse |
| CN1311030C (zh) * | 2003-01-28 | 2007-04-18 | 旭硝子株式会社 | 聚醚多元醇组合物及其用途 |
| DE102006024025A1 (de) | 2006-05-23 | 2007-11-29 | Bayer Materialscience Ag | Verfahren zur Herstellung von Polyetherpolyolen |
| DE102007038436A1 (de) | 2007-08-16 | 2009-02-19 | Bayer Materialscience Ag | Verfahren zur Herstellung von Polyolen |
| DE102008011683A1 (de) | 2008-02-28 | 2009-09-03 | Bayer Materialscience Ag | Verfahren zur Herstellung von Polyolen |
| DE102008028555A1 (de) | 2008-06-16 | 2009-12-17 | Bayer Materialscience Ag | Verfahren zur Herstellung von Polyolen |
| IL200997A0 (en) * | 2008-10-01 | 2010-06-30 | Bayer Materialscience Ag | Special polyether-based polyurethane formulations for the production of holographic media |
| IL200995A0 (en) * | 2008-10-01 | 2010-06-30 | Bayer Materialscience Ag | Polyether-based polyurethane formulations for the production of holographic media |
| DE102008051882A1 (de) | 2008-10-16 | 2010-04-29 | Bayer Materialscience Ag | Verfahren zur Herstellung von Polyetheresterpolyolen |
| US20100317824A1 (en) * | 2009-06-15 | 2010-12-16 | Dow Global Technologies Inc. | Polyether derivatives of secondary hydroxy fatty acids and derivatives thereof |
| DE102009031584A1 (de) | 2009-07-03 | 2011-01-05 | Bayer Materialscience Ag | Verfahren zur Herstellung von Polyetherpolyolen mit primären Hydroxyl-Endgruppen |
| DE102009042201A1 (de) | 2009-09-18 | 2011-04-14 | Bayer Materialscience Ag | Silangruppenhaltige Polyether |
| DE102009042190A1 (de) | 2009-09-18 | 2011-03-24 | Bayer Materialscience Ag | Silangruppenhaltige Reaktivverdünner |
| DE102009043616A1 (de) | 2009-09-29 | 2011-03-31 | Bayer Materialscience Ag | Verfahren zur Herstellung von aminogruppenhaltigen Polyolen |
| BR112012009266A2 (pt) | 2009-10-21 | 2016-05-31 | Bayer Materialscience Ag | hidrogel biodegradável |
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| PT2497085E (pt) | 2009-11-03 | 2014-03-27 | Bayer Ip Gmbh | Processo para a produção de um filme holográfico |
| EP2317511B1 (de) | 2009-11-03 | 2012-03-07 | Bayer MaterialScience AG | Photopolymerformulierungen mit einstellbarem mechanischem Modul Guv |
| CN102656209A (zh) | 2009-12-09 | 2012-09-05 | 陶氏环球技术有限责任公司 | 仲羟基脂肪酸及其衍生物的聚醚衍生物 |
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| DE102010008410A1 (de) | 2010-02-18 | 2011-08-18 | Bayer MaterialScience AG, 51373 | Verfahren zur Herstellung von Polyethercarbonatpolyolen |
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| US20110230581A1 (en) | 2010-03-17 | 2011-09-22 | Bayer Materialscience Llc | Process for the production of polyether polyols with a high ethylene oxide content |
| MX2012011003A (es) | 2010-03-24 | 2012-10-15 | Bayer Ip Gmbh | Procedimiento para la preparacion de polioletercarbonatos. |
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| US9115246B2 (en) | 2010-04-30 | 2015-08-25 | Basf Se | Polyether polyols, process for preparing polyether polyols and their use for producing polyurethanes |
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| US5482908A (en) | 1994-09-08 | 1996-01-09 | Arco Chemical Technology, L.P. | Highly active double metal cyanide catalysts |
| US5545601A (en) | 1995-08-22 | 1996-08-13 | Arco Chemical Technology, L.P. | Polyether-containing double metal cyanide catalysts |
| US5627120A (en) | 1996-04-19 | 1997-05-06 | Arco Chemical Technology, L.P. | Highly active double metal cyanide catalysts |
| US5714428A (en) * | 1996-10-16 | 1998-02-03 | Arco Chemical Technology, L.P. | Double metal cyanide catalysts containing functionalized polymers |
| DE19730467A1 (de) | 1997-07-16 | 1999-01-21 | Bayer Ag | Neue Zink/Metall-Hexacyanocobaltat-Katalysatoren für die Herstellung von Polyetherpolyolen |
| WO1999019063A1 (de) * | 1997-10-13 | 1999-04-22 | Bayer Aktiengesellschaft | Kristalline doppelmetallcyanid-katalysatoren für die herstellung von polyetherpolyolen |
| DE19810269A1 (de) * | 1998-03-10 | 2000-05-11 | Bayer Ag | Verbesserte Doppelmetallcyanid-Katalysatoren für die Herstellung von Polyetherpolyolen |
| ES2286005T3 (es) * | 1999-02-11 | 2007-12-01 | Bayer Materialscience Ag | Catalizadores de cianuro bimetalico para la preparacion de polioleteres. |
| DE19958355A1 (de) * | 1999-12-03 | 2001-06-07 | Bayer Ag | Verfahren zur Herstellung von DMC-Katalysatoren |
| AU2001260217A1 (en) * | 2000-04-20 | 2001-11-07 | Bayer Aktiengesellschaft | Method for producing double metal cyanide (dmc) catalysts |
| DE10122019A1 (de) * | 2001-05-07 | 2002-11-14 | Bayer Ag | Doppelmetallcyanid-Katalysatoren für die Herstellung von Polyetherpolyolen |
| US6797665B2 (en) * | 2002-05-10 | 2004-09-28 | Bayer Antwerpen | Double-metal cyanide catalysts for preparing polyether polyols |
| US6764978B2 (en) * | 2002-08-28 | 2004-07-20 | Basf Aktiengesellschaft | Multimetal cyanide compounds |
| US6696383B1 (en) * | 2002-09-20 | 2004-02-24 | Bayer Polymers Llc | Double-metal cyanide catalysts which can be used to prepare polyols and the processes related thereto |
-
1999
- 1999-02-11 DE DE19905611A patent/DE19905611A1/de not_active Withdrawn
-
2000
- 2000-01-31 AT AT00901607T patent/ATE273340T1/de not_active IP Right Cessation
- 2000-01-31 CA CA002362503A patent/CA2362503C/en not_active Expired - Fee Related
- 2000-01-31 AU AU22943/00A patent/AU2294300A/en not_active Abandoned
- 2000-01-31 ES ES00901607T patent/ES2226774T3/es not_active Expired - Lifetime
- 2000-01-31 ID IDW00200101907A patent/ID30028A/id unknown
- 2000-01-31 US US09/890,889 patent/US7008900B1/en not_active Expired - Lifetime
- 2000-01-31 BR BRPI0008106-0A patent/BR0008106B1/pt not_active IP Right Cessation
- 2000-01-31 HK HK02106361.6A patent/HK1044959B/zh not_active IP Right Cessation
- 2000-01-31 HU HU0200197A patent/HUP0200197A3/hu unknown
- 2000-01-31 PL PL00349858A patent/PL349858A1/xx not_active Application Discontinuation
- 2000-01-31 CN CNB008035660A patent/CN1138811C/zh not_active Expired - Lifetime
- 2000-01-31 CZ CZ20012882A patent/CZ296405B6/cs not_active IP Right Cessation
- 2000-01-31 DE DE50007385T patent/DE50007385D1/de not_active Expired - Lifetime
- 2000-01-31 PT PT00901607T patent/PT1165657E/pt unknown
- 2000-01-31 RU RU2001124862/04A patent/RU2235589C2/ru not_active IP Right Cessation
- 2000-01-31 JP JP2000598563A patent/JP4523170B2/ja not_active Expired - Fee Related
- 2000-01-31 EP EP00901607A patent/EP1165657B1/de not_active Expired - Lifetime
- 2000-01-31 WO PCT/EP2000/000727 patent/WO2000047649A1/de not_active Ceased
- 2000-01-31 KR KR1020017010106A patent/KR100599355B1/ko not_active Expired - Lifetime
- 2000-02-11 TW TW089102360A patent/TWI227248B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| RU2235589C2 (ru) | 2004-09-10 |
| PT1165657E (pt) | 2004-11-30 |
| PL349858A1 (en) | 2002-09-23 |
| ID30028A (id) | 2001-11-01 |
| ES2226774T3 (es) | 2005-04-01 |
| KR100599355B1 (ko) | 2006-07-12 |
| BR0008106A (pt) | 2001-11-13 |
| US7008900B1 (en) | 2006-03-07 |
| HUP0200197A2 (hu) | 2002-05-29 |
| BR0008106B1 (pt) | 2010-02-09 |
| CZ20012882A3 (cs) | 2001-10-17 |
| KR20010102029A (ko) | 2001-11-15 |
| CA2362503A1 (en) | 2000-08-17 |
| WO2000047649A1 (de) | 2000-08-17 |
| CZ296405B6 (cs) | 2006-03-15 |
| DE50007385D1 (de) | 2004-09-16 |
| DE19905611A1 (de) | 2000-08-17 |
| HUP0200197A3 (en) | 2003-08-28 |
| CA2362503C (en) | 2009-12-01 |
| EP1165657A1 (de) | 2002-01-02 |
| HK1044959B (zh) | 2004-12-17 |
| ATE273340T1 (de) | 2004-08-15 |
| JP2002536177A (ja) | 2002-10-29 |
| AU2294300A (en) | 2000-08-29 |
| EP1165657B1 (de) | 2004-08-11 |
| CN1138811C (zh) | 2004-02-18 |
| CN1340071A (zh) | 2002-03-13 |
| JP4523170B2 (ja) | 2010-08-11 |
| HK1044959A1 (en) | 2002-11-08 |
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| MM4A | Annulment or lapse of patent due to non-payment of fees |