CA2441185A1 - Double metal cyanide catalysts which can be used to prepare polyols and the processes related thereto - Google Patents
Double metal cyanide catalysts which can be used to prepare polyols and the processes related thereto Download PDFInfo
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- CA2441185A1 CA2441185A1 CA002441185A CA2441185A CA2441185A1 CA 2441185 A1 CA2441185 A1 CA 2441185A1 CA 002441185 A CA002441185 A CA 002441185A CA 2441185 A CA2441185 A CA 2441185A CA 2441185 A1 CA2441185 A1 CA 2441185A1
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- Prior art keywords
- metal cyanide
- double
- cyanide catalyst
- poly
- salt
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- 229910052751 metal Inorganic materials 0.000 title claims abstract 37
- 239000002184 metal Substances 0.000 title claims abstract 37
- 239000003054 catalyst Substances 0.000 title claims abstract 25
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 title claims abstract 20
- 238000000034 method Methods 0.000 title claims abstract 16
- 229920005862 polyol Polymers 0.000 title claims abstract 12
- 150000003077 polyols Chemical class 0.000 title claims abstract 12
- 150000003839 salts Chemical class 0.000 claims abstract 18
- 229920000642 polymer Polymers 0.000 claims abstract 9
- 230000000536 complexating effect Effects 0.000 claims abstract 5
- 239000003446 ligand Substances 0.000 claims abstract 5
- 150000002825 nitriles Chemical class 0.000 claims abstract 5
- 238000004519 manufacturing process Methods 0.000 claims abstract 4
- -1 sorbitan ester Chemical class 0.000 claims 9
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 4
- 239000004721 Polyphenylene oxide Substances 0.000 claims 4
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical group [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 claims 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims 4
- 150000001733 carboxylic acid esters Chemical class 0.000 claims 4
- 150000001875 compounds Chemical class 0.000 claims 4
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims 4
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 claims 4
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 claims 4
- 229920001515 polyalkylene glycol Polymers 0.000 claims 4
- 229920000570 polyether Polymers 0.000 claims 4
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 claims 4
- 229920002554 vinyl polymer Polymers 0.000 claims 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical group [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims 4
- 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 2
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 claims 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims 2
- 229920000858 Cyclodextrin Polymers 0.000 claims 2
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 claims 2
- 239000004354 Hydroxyethyl cellulose Substances 0.000 claims 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims 2
- 229930182556 Polyacetal Natural products 0.000 claims 2
- 239000004372 Polyvinyl alcohol Substances 0.000 claims 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 2
- 229920002125 Sokalan® Polymers 0.000 claims 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims 2
- 150000001408 amides Chemical class 0.000 claims 2
- 239000003613 bile acid Substances 0.000 claims 2
- RKBAPHPQTADBIK-UHFFFAOYSA-N cobalt;hexacyanide Chemical group [Co].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] RKBAPHPQTADBIK-UHFFFAOYSA-N 0.000 claims 2
- 229920001577 copolymer Polymers 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- 229930182470 glycoside Natural products 0.000 claims 2
- 150000002338 glycosides Chemical class 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 claims 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 2
- 239000011976 maleic acid Substances 0.000 claims 2
- 239000011574 phosphorus Substances 0.000 claims 2
- 229910052698 phosphorus Inorganic materials 0.000 claims 2
- 229920000191 poly(N-vinyl pyrrolidone) Polymers 0.000 claims 2
- 229920001446 poly(acrylic acid-co-maleic acid) Polymers 0.000 claims 2
- 229920002432 poly(vinyl methyl ether) polymer Polymers 0.000 claims 2
- 229920002401 polyacrylamide Polymers 0.000 claims 2
- 239000004584 polyacrylic acid Substances 0.000 claims 2
- 229920002239 polyacrylonitrile Polymers 0.000 claims 2
- 229920000515 polycarbonate Polymers 0.000 claims 2
- 239000004417 polycarbonate Substances 0.000 claims 2
- 229920000728 polyester Polymers 0.000 claims 2
- 229920005906 polyester polyol Polymers 0.000 claims 2
- 229920006324 polyoxymethylene Polymers 0.000 claims 2
- 229920002689 polyvinyl acetate Polymers 0.000 claims 2
- 239000011118 polyvinyl acetate Substances 0.000 claims 2
- 229920002451 polyvinyl alcohol Polymers 0.000 claims 2
- 239000001103 potassium chloride Substances 0.000 claims 2
- 235000011164 potassium chloride Nutrition 0.000 claims 2
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 claims 2
- 239000011780 sodium chloride Substances 0.000 claims 2
- 239000007858 starting material Substances 0.000 claims 2
- 150000005846 sugar alcohols Polymers 0.000 claims 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 2
- 235000005074 zinc chloride Nutrition 0.000 claims 2
- 239000011592 zinc chloride Substances 0.000 claims 2
- 229910052723 transition metal Inorganic materials 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 229910001507 metal halide Inorganic materials 0.000 abstract 1
- 150000005309 metal halides Chemical class 0.000 abstract 1
Classifications
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- 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
- B01J31/165—Polymer immobilised coordination complexes, e.g. organometallic complexes
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/16—Catalysts
- C08G18/22—Catalysts containing metal 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
- 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
-
- 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
- B01J31/1805—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 the ligands containing nitrogen
-
- 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
- B01J31/22—Organic complexes
- B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
- B01J31/2208—Oxygen, e.g. acetylacetonates
-
- 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
- B01J31/22—Organic complexes
- B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
- B01J31/2208—Oxygen, e.g. acetylacetonates
- B01J31/2226—Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
- B01J31/223—At least two oxygen atoms present in one at least bidentate or bridging ligand
- B01J31/2234—Beta-dicarbonyl ligands, e.g. acetylacetonates
-
- 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
- B01J31/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24
-
- 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
- B01J31/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24
- B01J31/28—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24 of the platinum group metals, iron group metals or copper
-
- 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
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- 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
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/10—Polymerisation reactions involving at least dual use catalysts, e.g. for both oligomerisation and polymerisation
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- 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
- B01J2531/02—Compositional aspects of complexes used, e.g. polynuclearity
- B01J2531/0202—Polynuclearity
- B01J2531/0205—Bi- or polynuclear complexes, i.e. comprising two or more metal coordination centres, without metal-metal bonds, e.g. Cp(Lx)Zr-imidazole-Zr(Lx)Cp
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- 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
- B01J2531/26—Zinc
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- 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
- B01J2531/827—Iridium
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- 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
- B01J2531/84—Metals of the iron group
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- 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
- B01J2531/84—Metals of the iron group
- B01J2531/845—Cobalt
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/10—Energy storage using batteries
Abstract
The present invention is directed to double metal cyanide catalysts ("DMC") which can be used to prepare polyols. DMC catalysts of the present invention are prepared by combining i) at least one metal salt; ii) at least one metal cyanide salt; iii) at least one organic complexing ligand; iv) at least one alkaline metal salt; and, optionally, v) at least one functionalized polymer. The present invention is also directed to a process for preparing a polyol in the presence of a DMC catalyst of or prepared according to the present invention.
Surprisingly, DMC catalysts of the present invention, which are preferably prepared with at least one alkaline metal halide, have acceptable activity and can be used to catalyze oxyalkylation reactions. Additionally, DMC catalysts produced by the process of the present invention can be used to prepare polyols which have reduced levels of high molecular weight tail.
Surprisingly, DMC catalysts of the present invention, which are preferably prepared with at least one alkaline metal halide, have acceptable activity and can be used to catalyze oxyalkylation reactions. Additionally, DMC catalysts produced by the process of the present invention can be used to prepare polyols which have reduced levels of high molecular weight tail.
Claims (25)
1. A process for preparing a double-metal cyanide catalyst comprising:
combining i) at least one metal salt;
ii) at least one metal cyanide salt;
iii) at least one organic complexing ligand;
iv) at least one alkaline metal salt; and v) optionally, at least one functionalized polymer;
under conditions sufficient to form a catalyst.
combining i) at least one metal salt;
ii) at least one metal cyanide salt;
iii) at least one organic complexing ligand;
iv) at least one alkaline metal salt; and v) optionally, at least one functionalized polymer;
under conditions sufficient to form a catalyst.
2. ~The process of Claim 1 in which the metal salt is zinc chloride.
3. ~The process of Claim 1 in which the metal cyanide salt is potassium hexacyanocobaltate (III).
4. ~The process of Claim 1 in which the organic complexing ligand is tert-butyl alcohol.
5. ~The process of Claim 1 in which the alkaline metal salt is potassium chloride, sodium chloride, sodium bromide, lithium chloride or lithium bromide.
6. ~The process of Claim 1 in which the functionalized polymer is present in an amount in the range of from about 2 to about 98 wt. %, based on the total weight of the double-metal cyanide catalyst.
7. ~The process of Claim 1 in which the functionalized polymer is a polyether; polyester; polycarbonate; polyalkylene glycol sorbitan ester; polyalkylene glycol glycidyl ether; polyacrylamide;
poly(acrylamide-co-acrylic acid), polyacrylic acid, poly(acrylic acid-co-maleic acid), poly(N-vinylpyrrolidone-co-acrylic acid), poly(acrylic acid-co-styrene) or their salts; maleic acid, styrene or maleic anhydride copolymers or their salts; polyacrylonitriles; polyalkyl acrylate; polyalkyl methacrylate; polyvinyl methyl ether; polyvinyl ethyl ether; polyvinyl acetate; polyvinyl alcohol; poly-N-vinylpyrrolidone; polyvinyl methyl ketone; poly(4-vinylphenol);
oxazoline polymer; polyalkyleneimine; hydroxyethylcellulose;
polyacetal; glycidyl ether; glycoside; carboxylic acid ester of polyhydric alcohol; bile acid or its salt, ester or amide; cyclodextrin;
phosphorus compound; unsaturated carboxylic acid ester; or an - ionic surface- or interface-active compound.
poly(acrylamide-co-acrylic acid), polyacrylic acid, poly(acrylic acid-co-maleic acid), poly(N-vinylpyrrolidone-co-acrylic acid), poly(acrylic acid-co-styrene) or their salts; maleic acid, styrene or maleic anhydride copolymers or their salts; polyacrylonitriles; polyalkyl acrylate; polyalkyl methacrylate; polyvinyl methyl ether; polyvinyl ethyl ether; polyvinyl acetate; polyvinyl alcohol; poly-N-vinylpyrrolidone; polyvinyl methyl ketone; poly(4-vinylphenol);
oxazoline polymer; polyalkyleneimine; hydroxyethylcellulose;
polyacetal; glycidyl ether; glycoside; carboxylic acid ester of polyhydric alcohol; bile acid or its salt, ester or amide; cyclodextrin;
phosphorus compound; unsaturated carboxylic acid ester; or an - ionic surface- or interface-active compound.
8. ~The double-metal cyanide catalyst prepared by the process of Claim 1.
9. ~The double-metal cyanide catalyst of Claim 8 which is comprised of at least one alkaline metal salt in an amount within the range of from about 0.4 to about 6 wt .%, based on the total weight of the double~
metal cyanide catalyst.
metal cyanide catalyst.
10. ~A process for preparing a polyol comprising:
combining i) at least one starter compound which has active hydrogen atoms; with ii) at least one oxide, in the presence of iii) at least one double-metal cyanide catalyst prepared according to the process of Claim 1;
under conditions sufficient to form a polyol.
combining i) at least one starter compound which has active hydrogen atoms; with ii) at least one oxide, in the presence of iii) at least one double-metal cyanide catalyst prepared according to the process of Claim 1;
under conditions sufficient to form a polyol.
11. ~A polyether polyol prepared by the process of Claim 10.
12. ~A polyester polyol prepared by the process of Claim 10.
13. ~A polyetherester polyol prepared by the process of Claim 10.
14.~A double-metal cyanide catalyst having the general formula M1 x([M2 x'(CN)y]z'[M3(x)(y)]).cndot. L1.ident.L2.cndot.M4 z wherein M1 represents at least one metal salt;
M2 represents at least one metal cyanide salt;
M3 represents at least one transition metal salt;
M4 represents at least one-alkaline metal salt;
L1 represents at least one organic complexing ligand;
L2 is optional and can represent at least one functionalized polymer;
and x, x', y and z are integers and are chosen such that electroneutrality of the double-metal cyanide catalyst exists.
M2 represents at least one metal cyanide salt;
M3 represents at least one transition metal salt;
M4 represents at least one-alkaline metal salt;
L1 represents at least one organic complexing ligand;
L2 is optional and can represent at least one functionalized polymer;
and x, x', y and z are integers and are chosen such that electroneutrality of the double-metal cyanide catalyst exists.
15. The double metal cyanide catalyst of Claim 14 in which the metal salt is zinc chloride.
16. The double metal cyanide catalyst of Claim 14 in which the metal cyanide salt is potassium hexacyanocobaltate (III).
17. The double metal cyanide catalyst of Claim 14 in which the organic complexing ligand is tert-butyl alcohol.
18. The double metal cyanide catalyst of Claim 14 in which the alkaline metal salt is potassium chloride, sodium chloride, sodium bromide, lithium chloride or lithium bromide.
19. The double metal cyanide catalyst of Claim 14 in which the functionalized polymer is present in an amount in the range of from about 2 to about 98 wt. %, based on the total weight of the double-metal cyanide catalyst.
20. The double metal cyanide catalyst of Claim 14 in which the functionalized polymer is a polyether; polyester; polycarbonate;
polyalkylene glycol sorbitan ester; polyalkylene glycol glycidyl ether;
polyacrylamide; poly(acrylamide-co-acrylic acid), polyacrylic acid, poly(acrylic acid-co-maleic acid), poly(N-vinylpyrrolidone-co-acrylic acid), poly(acrylic acid-co-styrene) or their salts; maleic acid, styrene or maleic anhydride copolymer; or their salts;
polyacrylonitriles; polyalkyl acrylate; polyalkyl methacrylate;
polyvinyl methyl ether; polyvinyl ethyl ether; polyvinyl acetate;
polyvinyl alcohol; poly-N-vinylpyrrolidone; polyvinyl methyl ketone;
poly(4-vinylphenol); oxazoline polymer; polyalkyleneimine;
hydroxyethylcellulose; polyacetal; glycidyl ether; glycoside;
carboxylic acid ester of polyhydric alcohol; bile acid or its salt, ester or amide; cyclodextrin; phosphorus compound; unsaturated carboxylic acid ester; or an ionic surface- or interface-active compound.~
polyalkylene glycol sorbitan ester; polyalkylene glycol glycidyl ether;
polyacrylamide; poly(acrylamide-co-acrylic acid), polyacrylic acid, poly(acrylic acid-co-maleic acid), poly(N-vinylpyrrolidone-co-acrylic acid), poly(acrylic acid-co-styrene) or their salts; maleic acid, styrene or maleic anhydride copolymer; or their salts;
polyacrylonitriles; polyalkyl acrylate; polyalkyl methacrylate;
polyvinyl methyl ether; polyvinyl ethyl ether; polyvinyl acetate;
polyvinyl alcohol; poly-N-vinylpyrrolidone; polyvinyl methyl ketone;
poly(4-vinylphenol); oxazoline polymer; polyalkyleneimine;
hydroxyethylcellulose; polyacetal; glycidyl ether; glycoside;
carboxylic acid ester of polyhydric alcohol; bile acid or its salt, ester or amide; cyclodextrin; phosphorus compound; unsaturated carboxylic acid ester; or an ionic surface- or interface-active compound.~
21. The double-metal cyanide catalyst of Claim 14 in which alkaline metal salt is present in an amount within the range of from about 0.4 to about 6 wt .%, based on the total weight of the double metal cyanide catalyst.
22. A process for preparing a polyol comprising:
combining i) at least one starter compound which has active hydrogen atoms; with ii) at least one oxide;
in the presence of iii) at least ore double-metal cyanide catalyst of Claim 14;
under conditions sufficient to form a polyol.
combining i) at least one starter compound which has active hydrogen atoms; with ii) at least one oxide;
in the presence of iii) at least ore double-metal cyanide catalyst of Claim 14;
under conditions sufficient to form a polyol.
23. A polyether polyol prepared by the process of Claim 22.
24. A polyester polyol prepared by the process of Claim 22.
25. A polyetherester polyol prepared by the process of Claim 22.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/251,155 | 2002-09-20 | ||
| US10/251,155 US6696383B1 (en) | 2002-09-20 | 2002-09-20 | Double-metal cyanide catalysts which can be used to prepare polyols and the processes related thereto |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2441185A1 true CA2441185A1 (en) | 2004-03-20 |
| CA2441185C CA2441185C (en) | 2012-07-24 |
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| Application Number | Title | Priority Date | Filing Date |
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| CA2441185A Expired - Fee Related CA2441185C (en) | 2002-09-20 | 2003-09-17 | Double metal cyanide catalysts which can be used to prepare polyols and the processes related thereto |
Country Status (15)
| Country | Link |
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| US (3) | US6696383B1 (en) |
| EP (1) | EP1400281B1 (en) |
| JP (1) | JP4949605B2 (en) |
| KR (1) | KR101065163B1 (en) |
| CN (2) | CN101077480A (en) |
| AT (1) | ATE475479T1 (en) |
| BR (1) | BR0304147B1 (en) |
| CA (1) | CA2441185C (en) |
| DE (1) | DE60333524D1 (en) |
| ES (1) | ES2347868T3 (en) |
| HK (1) | HK1065739A1 (en) |
| MX (1) | MXPA03008434A (en) |
| PL (1) | PL362241A1 (en) |
| RU (1) | RU2341328C2 (en) |
| SG (1) | SG107154A1 (en) |
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-
2002
- 2002-09-20 US US10/251,155 patent/US6696383B1/en not_active Expired - Lifetime
-
2003
- 2003-09-09 DE DE60333524T patent/DE60333524D1/en not_active Expired - Lifetime
- 2003-09-09 AT AT03019677T patent/ATE475479T1/en not_active IP Right Cessation
- 2003-09-09 ES ES03019677T patent/ES2347868T3/en not_active Expired - Lifetime
- 2003-09-09 EP EP03019677A patent/EP1400281B1/en not_active Expired - Lifetime
- 2003-09-16 BR BRPI0304147-6B1A patent/BR0304147B1/en not_active IP Right Cessation
- 2003-09-17 CA CA2441185A patent/CA2441185C/en not_active Expired - Fee Related
- 2003-09-17 SG SG200305634A patent/SG107154A1/en unknown
- 2003-09-17 PL PL03362241A patent/PL362241A1/en not_active Application Discontinuation
- 2003-09-18 MX MXPA03008434A patent/MXPA03008434A/en active IP Right Grant
- 2003-09-19 RU RU2003128081/04A patent/RU2341328C2/en not_active IP Right Cessation
- 2003-09-19 CN CNA2007101101989A patent/CN101077480A/en active Pending
- 2003-09-19 CN CNB031327761A patent/CN1331600C/en not_active Expired - Fee Related
- 2003-09-19 JP JP2003327513A patent/JP4949605B2/en not_active Expired - Fee Related
- 2003-09-19 KR KR1020030064955A patent/KR101065163B1/en active IP Right Grant
- 2003-11-19 US US10/717,094 patent/US6867162B2/en not_active Expired - Lifetime
- 2003-11-19 US US10/717,093 patent/US7223832B2/en active Active
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- 2004-11-01 HK HK04108537A patent/HK1065739A1/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| KR20040025838A (en) | 2004-03-26 |
| MXPA03008434A (en) | 2004-10-29 |
| PL362241A1 (en) | 2004-03-22 |
| ES2347868T3 (en) | 2010-11-24 |
| RU2341328C2 (en) | 2008-12-20 |
| HK1065739A1 (en) | 2005-03-04 |
| CA2441185C (en) | 2012-07-24 |
| DE60333524D1 (en) | 2010-09-09 |
| US20040102314A1 (en) | 2004-05-27 |
| BR0304147B1 (en) | 2013-10-01 |
| SG107154A1 (en) | 2004-11-29 |
| US20040116281A1 (en) | 2004-06-17 |
| EP1400281A1 (en) | 2004-03-24 |
| CN1494946A (en) | 2004-05-12 |
| CN1331600C (en) | 2007-08-15 |
| KR101065163B1 (en) | 2011-09-15 |
| JP4949605B2 (en) | 2012-06-13 |
| BR0304147A (en) | 2004-09-08 |
| US6696383B1 (en) | 2004-02-24 |
| US7223832B2 (en) | 2007-05-29 |
| JP2004114037A (en) | 2004-04-15 |
| US6867162B2 (en) | 2005-03-15 |
| CN101077480A (en) | 2007-11-28 |
| ATE475479T1 (en) | 2010-08-15 |
| EP1400281B1 (en) | 2010-07-28 |
| RU2003128081A (en) | 2005-03-27 |
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