WO2006100219A1 - Process for the preparation of an improved double metal cyanide complex catalyst, double metal cyanide catalyst and use of such catalyst - Google Patents
Process for the preparation of an improved double metal cyanide complex catalyst, double metal cyanide catalyst and use of such catalyst Download PDFInfo
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- WO2006100219A1 WO2006100219A1 PCT/EP2006/060872 EP2006060872W WO2006100219A1 WO 2006100219 A1 WO2006100219 A1 WO 2006100219A1 EP 2006060872 W EP2006060872 W EP 2006060872W WO 2006100219 A1 WO2006100219 A1 WO 2006100219A1
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- Prior art keywords
- catalyst
- dmc
- particle size
- dispersion
- process according
- Prior art date
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- 239000003054 catalyst Substances 0.000 title claims abstract description 143
- 238000000034 method Methods 0.000 title claims abstract description 32
- 229910052751 metal Inorganic materials 0.000 title claims abstract description 26
- 239000002184 metal Substances 0.000 title claims abstract description 26
- 238000002360 preparation method Methods 0.000 title claims abstract description 17
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 title claims abstract description 15
- 239000006185 dispersion Substances 0.000 claims abstract description 31
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 7
- 238000004062 sedimentation Methods 0.000 claims abstract description 5
- 239000002245 particle Substances 0.000 claims description 84
- 239000008139 complexing agent Substances 0.000 claims description 10
- 239000007864 aqueous solution Substances 0.000 claims description 9
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical group [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 229910052725 zinc Inorganic materials 0.000 claims description 6
- 239000011701 zinc Substances 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 150000002825 nitriles Chemical class 0.000 claims description 5
- 238000006116 polymerization reaction Methods 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 2
- 239000012736 aqueous medium Substances 0.000 claims description 2
- 239000000243 solution Substances 0.000 claims description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 9
- 229920005862 polyol Polymers 0.000 description 9
- 150000003077 polyols Chemical class 0.000 description 9
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 238000002441 X-ray diffraction Methods 0.000 description 6
- 239000004721 Polyphenylene oxide Substances 0.000 description 5
- 229920000570 polyether Polymers 0.000 description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 229920001451 polypropylene glycol Polymers 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- -1 cyanide compound Chemical class 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 229960004592 isopropanol Drugs 0.000 description 2
- 150000002924 oxiranes Chemical class 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- XLJKHNWPARRRJB-UHFFFAOYSA-N cobalt(2+) Chemical compound [Co+2] XLJKHNWPARRRJB-UHFFFAOYSA-N 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- ZAEAYFVVHCPYDI-UHFFFAOYSA-N dizinc;iron(2+);hexacyanide Chemical compound [Fe+2].[Zn+2].[Zn+2].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] ZAEAYFVVHCPYDI-UHFFFAOYSA-N 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- SWODCICMZQPBPU-UHFFFAOYSA-N iron(2+);nickel(2+);hexacyanide Chemical compound [Fe+2].[Ni+2].[Ni+2].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] SWODCICMZQPBPU-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 1
- 229920005906 polyester polyol Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 239000011527 polyurethane coating Substances 0.000 description 1
- 238000000634 powder X-ray diffraction Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 150000003384 small molecules Chemical group 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- YJUIKPXYIJCUQP-UHFFFAOYSA-N trizinc;iron(3+);dodecacyanide Chemical compound [Fe+3].[Fe+3].[Zn+2].[Zn+2].[Zn+2].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] YJUIKPXYIJCUQP-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
Classifications
-
- 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
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
-
- B01J35/40—
-
- 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
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
-
- 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
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/0009—Use of binding agents; Moulding; Pressing; Powdering; Granulating; Addition of materials ameliorating the mechanical properties of the product catalyst
- B01J37/0027—Powdering
- B01J37/0036—Grinding
-
- 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
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/009—Preparation by separation, e.g. by filtration, decantation, screening
-
- 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
-
- 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
Definitions
- the present invention relates to a process for the preparation of a double metal cyanide catalyst; a catalyst, which is obtainable with such a process; and a process wherein such a catalyst can be used.
- Double metal cyanide (DMC) catalysts are well known for polymerizing alkylene oxides like propylene oxide and ethylene oxide to prepare poly (alkylene oxide) polymers, also referred to as polyether polyols.
- the catalysts can be used to make a variety of polymer products, including polyester polyols and polyetherester polyols.
- the polyols can be used for preparing polyurethanes by reacting them with poiyisocyanates under appropriate conditions.
- Poly urethane products that can be made include polyurethane coatings, elastomers, sealants, foams, and adhesives.
- the DMC catalysts are highly active, and give polyether polyols that have low unsaturation compared with similar polyols made using strong basic catalysts such as potassium hydroxide.
- WO-A-97/26080 describes a process for the preparation of a paste of double metal cyanide compound, an organic complexing agent and water, wherein the paste comprises at least about 90 wt % of particles having a particle size within the range of about 0.1 to about 10 microns.
- US-A-5900384 describes a process for the preparation of a double metal cyanide complex catalyst comprising the preparation of a slurry of double metal cyanide complex catalyst particles and drying said particles by spray drying. This method is, however, cumbersome and energy intensive and consequently costly.
- the present invention provides a process for the preparation of a double metal cyanide (DMC) catalyst comprising a) preparation of a DMC catalyst; b) dispersing the catalyst of step a) in a dispersion agent, yielding a catalyst dispersion; c) allowing sedimentation of part of the catalyst from the catalyst dispersion obtained in step b) , yielding a sedimentated catalyst and a dispersed catalyst; d) separating the dispersed catalyst from the sedimentated catalyst.
- DMC double metal cyanide
- the catalyst prepared according to the present invention is highly active.
- the process of the present invention allows one to reduce the particle size of a DMC catalyst whilst the amorphous or crystalline structure of such DMC catalyst is maintained.
- the present invention provides a catalyst obtainable by such a process and a process for use of such a catalyst.
- Figures of the invention The invention is illustrated with the following figures: Figure 1: X-ray diffraction spectrum of a DMC catalyst
- Figure 2a Particle size distribution of a catalyst A not according to the invention
- Figure 2b Particle size distribution of a catalyst B according to the invention
- Step a) of the process according to the invention may be carried out in any manner known to the skilled person to be suitable for this purpose.
- DMC catalysts can be prepared by reacting aqueous solutions of metal salts and metal cyanide salts to form a precipitate of the DMC compound.
- the catalysts are prepared in the presence of an organic complexing agent.
- organic complexing agents include ethers such as glyme (dimethoxy-ethane) or diglyme and alcohols, such as iso- propyl- alcohol or tert-butyl alcohol.
- the complexing agent favourably impacts the activity of the catalyst for epoxide polymerization.
- Other known complexing agents include ketones, esters, amides and ureas. Processes for the preparation of double metal cyanide catalysts are for example given in EP-A-654302 and WO-01/72418.
- the DMC catalyst can for example be obtained by i) combining an aqueous solution of a metal salt with an aqueous solution of a metal cyanide salt and reacting these solution wherein at least part of this reaction takes place in the presence of an organic complexing agent, thereby forming a dispersion of a solid DMC complex in an aqueous medium; ii) combining the dispersion obtained in step (i) with a liquid, which is essentially insoluble in water and which is capable of extracting the solid DMC complex allowing a two-phase system to be formed consisting of a first aqueous layer and a layer containing the DMC complex and the liquid added; iii) removing the first aqueous layer; and iv) recovering the DMC catalyst from the layer containing the DMC catalyst.
- the catalyst might also be prepared by i) intimately combining and reacting an aqueous solution of a water-soluble metal salt and an aqueous solution of a water-soluble metal cyanide salt in the present of an organic complexing agent, to obtain an aqueous mixture that contains a precipitated DMC catalyst; ii) isolating and drying the catalyst obtained in step i) .
- DMC catalysts examples include zinc hexacyanocobaltate ( II ) , zinc hexacyanoferrate (III), zinc hexacyanoferrate (II), nickel (II) hexacyanoferrate (II ) and cobalt (II ) hezxacyanocobaltate ( III ). Further examples are listed in US-A-5158922, which is herewith incorporated by reference .
- the DMC catalyst is a zinc hexacyanocobaltate, preferably complexed with a water soluble aliphatic alcohol, most preferably complexed with tert-butyl alcohol.
- the catalyst of step a) is dispersed in a dispersing agent .
- the dispersion agent is a low molecular weight compound, having a molecular weight in the range from 50 to 1000, more preferably in the range from 100 to 800.
- Preferred dispersion agents include polyols such as polypropylene glycol. Especially preferred is a polypropylene glycol having a molecular weight in the range from 200 to 700.
- the dispersion can be prepared by simply mixing of the DMC catalyst and the dispersion agent, possibly with assistance of a mechanical or magnetic stirrer. By sedimentation is understood settling of the particles under gravity or centrifugal force. Sedimentation can be achieved by allowing the catalyst dispersion to stand over a period of time. Preferably the catalyst dispersion is allowed to settle for a period in the range from 1 to 72 hours, more preferably for a period in the range from 3 to 48 hours and most preferably for a period in the range from 7 to 24 hours.
- dispersed catalyst can be separated from sedimentated catalyst.
- at least 1% by weight of the total amount of catalyst present is sedimentated, more preferably at least 5% by weight and most preferably at least 10% by weight.
- at most 70% by weight of the total amount of catalyst present is sedimentated, more preferably at most 50% by weight and most preferably at most 30% by weight.
- Preferably only part of the dispersed catalyst is used in any further steps, such as for example the preparation of polyether polyols.
- Preferably at most 80% by volume of the total volume of dispersed catalyst more preferably at most 70% by volume and most preferably at most 50% by volume.
- at least 1% by volume, more preferably at least 3% by volume and most preferably at least 5% by volume is used.
- the particle size of such a DMC catalyst is reduced to obtain a double metal cyanide (DMC) catalyst having a particle size distribution wherein 95 volume% or more of the particles have a particle size smaller than 50 micron.
- DMC double metal cyanide
- the catalyst particle size is reduced to obtain a particle size distribution wherein 98 volume% or more of the particles have a particle size smaller than 50 micron, and more preferably the catalysts has a particle size distribution wherein 99 volume% or more of the particles have a particle size smaller than 50 micron. Most preferably essentially 100% of the particles have a particle size smaller than 50 micron.
- the catalyst particle size is reduced to obtain a particle size distribution wherein 95 volume% or more of the particles have a particle size smaller than 40 micron. More preferably the catalyst has a particle size distribution wherein 98 volume% or more of the particles have a particle size smaller than 40 micron, and more preferably the catalysts has a particle size distribution wherein 99 volume% or more of the particles have a particle size smaller than 40 micron. Most preferably essentially 100% of the particles have a particle size smaller than 40 micron . In another preferred embodiment the catalyst particle size is reduced to obtain a particle size distribution wherein 85 volume% or more of the particles have a particle size smaller than 20, preferably 19 micron .
- the catalyst has a particle size distribution wherein 90 volume?; or more of the particles have a particle size smaller than 20, preferably 19 micron, and more preferably the catalysts has a particle size distribution wherein 95 volume% or more of the particles have a particle size smaller than 20, preferably 19 micron.
- the catalyst particle size is reduced to obtain a particle size distribution wherein 60 volume% or more of the particles have a particle size smaller than 10 micron. More preferably the catalyst has a particle size distribution wherein 70 volume% or more of the particles have a particle size smaller than 10 micron.
- mean particle size also sometimes called Mass
- MMD Median Diameter
- the mean particle size of the catalyst particles preferably lies in the range from 2 to 20 micron. More preferably the mean particle size is less than 15 micron and even more preferably less than 10 micron. Even more preferably the mean particle size is less than 7.5 micron. In a further preferred embodiment the mean particle size is at least 3 micron. Most preferably the mean particle size of the catalyst particles lies in the range from 3 to 7.5 micron.
- the catalyst can be mainly crystalline or mainly amorphous.
- a crystalline catalyst include the catalysts described in EP-A-1257591, EP-B-1259560 and WO-A-99/44739.
- a DMC catalyst is used which comprises i) up to 10 wt . % of crystalline DMC component and ii) at least 90 wt . % of a DMC component which is amorphous to X-rays. More preferably a DMC, a DMC catalyst is used which comprises at least 99 wt . % of a DMC component, which is amorphous to X-rays.
- amorphous is understood lacking a well-defined crystal structure or characterised by the substantial absence of sharp lines in the X-ray diffraction pattern.
- the process of the present invention advantageously allows one to reduce the particle size of a DMC catalyst whilst the amorphous or crystalline structure of such DMC catalyst is maintained.
- Powder X-ray diffraction (XRD) patterns of conventional double metal cyanide catalysts show characteristic sharp lines that correspond to the presence of a substantial proportion of a highly crystalline DMC component.
- One of the preferred DMC catalysts is a catalyst according to EP-A-654302.
- the catalysts described herein can advantageously be used for polymerization of alkylene oxides, which polymerization comprises polymerising an alkylene oxide in the presence of a DMC catalyst.
- a polymerization can for example be carried out as described in
- catalyst B had a different mean particle size and particle size distribution than catalyst A.
- the mean particle size and particle size distribution for both catalyst A as well as catalyst B are given in table 2.
- the particle size distribution is further illustrated in respectively figure 2a and figure 2b.
- PSD particle size distribution
- the MasterSizer S has a 2 milliwatts He-Ne laser which is used at a wavelength of 632.8 nm.
- a 300 RF mm lens is used giving a PSD range of 0.05-878.67 ⁇ m.
- the active beam length is 2.4 mm. The analysis is using the
- Part of the catalyst dispersion is brought into a dispersion unit filled with Ethanol 96% denaturated with 5% Methanol until an obscuration of 10-15% is reached.
- the dispersion unit is connected to the measurement cell.
- One measurement is done by performing a total of 10000 Sampling Sweeps. All 45 data channels of the apparatus were used.
- the particles are assumed to be round for the above measurements and the generated values are assumed to be values of the diameter of the particles.
- a 1.25 liter stirred tank reactor was charged with a suspension of 89 g of propoxylated glycerol having an average molecular weight of 670 and an amount of catalyst dispersion A or B as indicated in table 3.
- the reactor was heated to 130 0 C. at a pressure of 0.1 bara or less with a small nitrogen purge.
- the reactor was evacuated and propylene oxide was added at a rate of 3.25 grams per minute until the pressure reached 1.3 bara.
- the addition of propylene oxide was started again and was continued such that the pressure was kept between 0.6 and 0.8 bara.
- a polyether polyol having a molecular weight of 3000 was obtained and the addition of glycerine was started at a rate of 0.1 grams per minute.
Abstract
Description
Claims
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US11/886,796 US20090043056A1 (en) | 2005-03-22 | 2006-03-20 | Process for the Preparation of an Improved Double Metal Cyanide Complex Catalyst, Double Metal Cyanide Catalyst and Use of Such Catalyst |
EP06743210A EP1861199A1 (en) | 2005-03-22 | 2006-03-20 | Process for the preparation of an improved double metal cyanide complex catalyst, double metal cyanide catalyst and use of such catalyst |
JP2008502389A JP2008534248A (en) | 2005-03-22 | 2006-03-20 | Process for producing improved double metal cyanide complex catalyst, double metal cyanide catalyst and method of use thereof |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP05102314 | 2005-03-22 | ||
EP05102314.1 | 2005-03-22 |
Publications (1)
Publication Number | Publication Date |
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WO2006100219A1 true WO2006100219A1 (en) | 2006-09-28 |
Family
ID=34939049
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2006/060872 WO2006100219A1 (en) | 2005-03-22 | 2006-03-20 | Process for the preparation of an improved double metal cyanide complex catalyst, double metal cyanide catalyst and use of such catalyst |
Country Status (6)
Country | Link |
---|---|
US (1) | US20090043056A1 (en) |
EP (1) | EP1861199A1 (en) |
JP (1) | JP2008534248A (en) |
KR (1) | KR20070112793A (en) |
CN (1) | CN101128261A (en) |
WO (1) | WO2006100219A1 (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102008020980A1 (en) | 2008-04-25 | 2009-10-29 | Henkel Ag & Co. Kgaa | Curable compositions containing silylated polyurethanes based on polyether block polymers |
DE102009046269A1 (en) | 2009-10-30 | 2011-05-05 | Henkel Ag & Co. Kgaa | Urea-bound alkoxysilanes for use in sealants and adhesives |
EP2716682A4 (en) * | 2011-06-03 | 2015-05-20 | Sumitomo Seika Chemicals | Polyalkylene oxide particles and production method for same |
EP2716681A4 (en) * | 2011-06-03 | 2015-05-27 | Sumitomo Seika Chemicals | Polyalkylene oxide particles and production method for same |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2011160296A1 (en) * | 2010-06-23 | 2011-12-29 | Basf Se | Modified double metal cyanide catalyst |
EP3622002A1 (en) * | 2017-05-10 | 2020-03-18 | Dow Global Technologies, LLC | Catalyst complex |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1997026080A1 (en) * | 1996-01-19 | 1997-07-24 | Arco Chemical Technology, L.P. | Improved double metal cyanide catalysts and methods for making them |
US5900384A (en) * | 1996-07-18 | 1999-05-04 | Arco Chemical Technology L.P. | Double metal cyanide catalysts |
US6780813B1 (en) * | 1999-12-03 | 2004-08-24 | Bayer Aktiengesellschaft | Process for producing DMC catalysts |
US20040242937A1 (en) * | 2001-08-22 | 2004-12-02 | Eva Baum | Method for increasing the catalytic activity of multi-metal cyanide compounds |
WO2004108794A1 (en) * | 2003-06-04 | 2004-12-16 | Asahi Glass Company, Limited | Composite metal cyanide complex catalyst, process for producing the same, and use of the same |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5158922A (en) * | 1992-02-04 | 1992-10-27 | Arco Chemical Technology, L.P. | Process for preparing metal cyanide complex catalyst |
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2006
- 2006-03-20 CN CNA2006800056956A patent/CN101128261A/en active Pending
- 2006-03-20 US US11/886,796 patent/US20090043056A1/en not_active Abandoned
- 2006-03-20 JP JP2008502389A patent/JP2008534248A/en active Pending
- 2006-03-20 KR KR1020077020989A patent/KR20070112793A/en not_active Application Discontinuation
- 2006-03-20 EP EP06743210A patent/EP1861199A1/en not_active Withdrawn
- 2006-03-20 WO PCT/EP2006/060872 patent/WO2006100219A1/en not_active Application Discontinuation
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Cited By (8)
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DE102008020980A1 (en) | 2008-04-25 | 2009-10-29 | Henkel Ag & Co. Kgaa | Curable compositions containing silylated polyurethanes based on polyether block polymers |
DE102009046269A1 (en) | 2009-10-30 | 2011-05-05 | Henkel Ag & Co. Kgaa | Urea-bound alkoxysilanes for use in sealants and adhesives |
WO2011051491A1 (en) | 2009-10-30 | 2011-05-05 | Henkel Ag & Co. Kgaa | Urea-bonded alkoxysilanes for use in sealants and adhesives |
US8501903B2 (en) | 2009-10-30 | 2013-08-06 | Henkel Ag & Co. Kgaa | Urea-bonded alkoxysilanes for use in sealants and adhesives |
EP2716682A4 (en) * | 2011-06-03 | 2015-05-20 | Sumitomo Seika Chemicals | Polyalkylene oxide particles and production method for same |
EP2716681A4 (en) * | 2011-06-03 | 2015-05-27 | Sumitomo Seika Chemicals | Polyalkylene oxide particles and production method for same |
US9416226B2 (en) | 2011-06-03 | 2016-08-16 | Sumitomo Seika Chemicals Co., Ltd. | Polyalkylene oxide particles and production method for the same |
US9447237B2 (en) | 2011-06-03 | 2016-09-20 | Sumitomo Seika Chemicals Co., Ltd. | Polyalkylene oxide particles and production method for the same |
Also Published As
Publication number | Publication date |
---|---|
KR20070112793A (en) | 2007-11-27 |
JP2008534248A (en) | 2008-08-28 |
CN101128261A (en) | 2008-02-20 |
US20090043056A1 (en) | 2009-02-12 |
EP1861199A1 (en) | 2007-12-05 |
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