WO2011085772A1 - Procédé pour la préparation de polyols catalysée par un dmc - Google Patents

Procédé pour la préparation de polyols catalysée par un dmc Download PDF

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Publication number
WO2011085772A1
WO2011085772A1 PCT/EP2010/007641 EP2010007641W WO2011085772A1 WO 2011085772 A1 WO2011085772 A1 WO 2011085772A1 EP 2010007641 W EP2010007641 W EP 2010007641W WO 2011085772 A1 WO2011085772 A1 WO 2011085772A1
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WIPO (PCT)
Prior art keywords
ppm
din
propylene oxide
content
determined
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PCT/EP2010/007641
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English (en)
Inventor
Raimund Ruppel
Jürgen Winkler
Thomas Ostrowski
Achim LÖFFLER
Hermann Graf
Original Assignee
Basf Se
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Priority to SG2012039707A priority Critical patent/SG181448A1/en
Publication of WO2011085772A1 publication Critical patent/WO2011085772A1/fr

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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
    • C08G65/26—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
    • 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
    • C08G65/2696—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 process or apparatus used

Definitions

  • the present invention relates to an improved process for preparing polyether alcohols by means of DMC catalysis, to the polyether alcohols prepared with the process, and to their use, in particular for producing polyurethanes.
  • the preparation of polyether alcohols by means of DMC catalysis is now prior art, especially for polyols for slabstock and CASE polyols.
  • the advantages of the DMC catalysts are firstly that the addition reaction of the alkylene oxides proceeds at a higher reaction rate, and secondly the polyether alcohols prepared in this way are characterized by a lower content of unsaturated fractions in the polyether chain.
  • the DMC catalysts can be used particularly advantageously in the preparation of polyether alcohols with high molecular weight and low functionality, as are used in particular for producing polyurethane flexible foams.
  • polyether alcohols with a high functionality in particular those with a functionality of at least 4, are used.
  • the object of the invention was to improve the process such that these disturbances no longer occur.
  • PO propylene oxide
  • aldehydes e.g. acetaldehyde
  • ketones e.g. acetone
  • hydrocarbons for example lower saturated and unsaturated hydrocarbons
  • acids for example carboxylic acids such as acetic acid.
  • the invention provides a process for preparing polyols by means of the addition reaction of alkylene oxides onto H-functional starter molecules in the presence of D C catalysts, wherein, during the alkoxylation, propylene oxide is used in which the sum of the contents of organo- halogen compounds, in particular chlorine compounds and bromine compounds, determined according to DIN 51408-2 and EN ISO 10304, is not more than 150 ppm, for example not more than 60 ppm, or even not more than 30 ppm; in which the sum of the contents of aldehydes and ketones, determined according to VDI 3862 Part 2, is not more than 300 ppm, for example not more than 120 ppm, or even not more than 60 ppm; whose content of allyl alcohol, determined by means of gas chromatography analogously to DIN 51405, is not more than 8500 ppm, for example not more than 3400 ppm, or even not more than 1700 ppm; whose content of hydrocarbons, the content of which is determined by means of gas
  • propylene oxide is used whose content of water, determined by Karl-Fischer titration according to DIN EN 13267, is not more than 500 ppm, for example not more than 200 ppm, or even not more than 100 ppm.
  • propylene oxide is used whose content of acid, expressed by the value determined by means of acid-base titration according to DIN EN 62021-2 or DIN 12634 and calculated for acetic acid, is not more than 100 ppm, for example not more than 40 ppm, or even not more than 20 ppm.
  • propylene oxide is used whose content of ethylene oxide, determined by gas chromatography analogously to DIN 51405, is not more than 100 ppm.
  • the invention also provides the polyols prepared with the process according to the invention and also the use thereof for producing polyurethanes, for example polyurethane foams or polyurethanes for coatings, adhesives, sealing compositions or elastomers (CASE) .
  • polyurethanes for example polyurethane foams or polyurethanes for coatings, adhesives, sealing compositions or elastomers (CASE) .
  • Polyurethanes are produced in large amounts. They are usually produced by reacting polyisocyanates with compounds having hydrogen atoms that are reactive towards isocyanate groups, in particular polyether alcohols and/or polyester alcohols .
  • Polyester alcohols are in most cases prepared by reacting polyfunctional alcohols with polyfunctional carboxylic acids.
  • Polyfunctional alcohols which may be used are the polyols prepared according to the invention.
  • the preparation of polyether alcohols takes place according to the invention by the addition reaction of alkylene oxides onto H-functional starter molecules in the presence of DMC catalysts.
  • H-functional starter substances which may be used are, for example, alcohols, in particular alcohols having 1 to 8 hydroxyl groups, preferably aliphatic and cycloaliphatic alcohols having 2 to 8 carbon atoms in the branched or unbranched alkyl chain or in the cycloaliphatic backbone .
  • the polyfunctional alcohols are selected from the group comprising glycerol, trimethylolpropane, pentaerythritol, di- and tripentaerythritol, ethylene glycol and its homologs, in particular ethylene glycol and/or diethylene glycol, propylene glycol and its higher homologs, in particular propylene glycol and/or dipropylene glycol, 1, 3-propanediol, 1,2-, 1,3-, 2,3- and 1,4-butane- diol, pentane- and hexanediols, in particular 1,5-pentane- diol and 1, 6-hexanediol .
  • starters are hydroxycarboxylic acids, hydroxyaldehydes, hydroxyketones ; tridecanol N and polymers thereof; esters of acrylic acid and methacrylic acid with difunctional alcohols such as HEA, HPA, HEMA, HP A; vinyl ethers such as HBVE; isoprenol; polyesterols ; lower alkoxylates of the aforementioned starters, of sucrose or sorbitol.
  • the starters can be introduced as initial charge or, if appropriate, also be metered in during the process.
  • Alkylene oxides which can be used are, for example, ethylene oxide, propylene oxide, 1,2- or 2,3-butylene oxide, 1, 2-isobutylene oxide, and also any desired mixtures thereof. In one embodiment of the invention, ethylene oxide, propylene oxide or mixtures thereof are used. In a further embodiment, exclusively propylene oxide is used.
  • the alkylene oxides can be added onto the starter molecules individually in the form of so-called blocks and, in the event of using different alkylene oxides, in any desired mixing ratio as mixed blocks. Moreover, the mixing ratio of the alkylene oxides during the synthesis can be varied discontinuously and also continuously.
  • Suitable DMC catalysts are described, for example, in EP 0 761 708 A2 and in EP 0 862 947 Al, both of which are hereby incorporated into this application by reference.
  • the double metal cyanide catalysts satisfy the formula: in which
  • M 1 is a metal ion selected from the group consisting of Zn 2+ , Fe 2+ , Co 3+ , Ni 2+ , Mn 2+ , Co + , Sn 2+ , Pb 2+ , Mo + , Mo 6+ , Al 3+ , V 4+ , V 5+ , Sr 2+ , W + , W 6+ , Cr 2+ , Cr 3+ , Cd 2+ , La 3+ , Ce 3+ , Ce 4+ , Eu 3+ , Mg 2+ , Ti 3+ , Ti + , Ag + , Rh 1+ , Ru 2+ , Ru 3+ , Pd 2+ ;
  • M 2 is a metal ion selected from the group consisting of Fe 2+ , Fe 3+ , Co + , Co 3+ , Mn 2+ , Mn 3+ , V 4+ , V 5+ , Cr 2+ , Cr 3+ , Rh 3+ , Ru + , lr 3+ ; and M 1 and M 2 are different;
  • A is an anion selected from the group consisting of halide, hydroxide, sulfate, carbonate, cyanide, thiocyanate, isocyanate, cyanate, carboxylate, oxalate and nitrate;
  • X is an anion selected from the group consisting of halide, hydroxide, sulfate, carbonate, cyanide, thiocyanate, isocyanate, cyanate, carboxylate, oxalate and nitrate;
  • L is a water-miscible ligand selected from the group consisting of alcohols, aldehydes, ketones, ethers, polyethers, esters, polyesters, polycarbonates, ureas, amides, nitriles and sulfides and mixtures thereof;
  • P is an organic additive selected from the group consisting of polyethers, polyesters, polycarbonates, polyalkylene glycol sorbitan esters, polyalkylene glycol glycidyl ethers, polyacrylamide, poly (acrylamide-co-acrylic acid), polyacrylic acid, poly (acrylamide-co-maleic acid), polyacrylonitrile, polyalkyl acrylates, polyalkyl methacrylates, polyvinyl methyl ethers, polyvinyl ethyl ether, polyvinyl acetate, polyvinyl alcohol, poly-N- vinylpyrrolidone, poly (N-vinylpyrrolidone-co-acrylic acid), polyvinyl methyl ketone, poly (4-vinylphenol) , poly(acrylic acid-co-styrene) , oxazoline polymers, polyalkyleneimines, maleic acid and maleic anhydride copolymers, hydroxyethylcellulose, polyacetates, ionic surface
  • f and k are zero if c is not zero and A is carboxylate, oxalate or nitrate.
  • the catalyst may be crystalline or amorphous. If k is zero, crystalline double metal cyanide compounds are preferred. If k is greater than zero, both crystalline, partially crystalline and also essentially amorphous catalysts are preferred.
  • the catalyst of the formula (I) has a value for k which is greater than zero.
  • the catalyst then comprises at least one multimetal cyanide compound, at least one organic ligand L; and at least one organic additive P.
  • k is zero or assumes a value such that the content of component P is not more than 4% by weight, based on the compound of the formula (I) .
  • e is likewise zero and X is exclusively carboxylate, preferably formate, acetate or propionate.
  • f is greater than zero, preferably zero to 6.
  • the catalyst in which one metal salt is present in the DMC catalyst, the catalyst has a structure which exhibits a particularly high catalytic activity. In this embodiment, the catalyst preferably has a crystalline structure .
  • the DMC catalysts comprise a water-miscible organic ligand, mostly in an amount of from 0.5 to 30% by weight, and an organic additive, for example a polyether alcohol, mostly in an amount of from 5 to 80% by weight, as described e.g. in WO 98/16310 Al, which is hereby incorporated into this application by reference.
  • the DMC catalyst is crystalline and has a platelet-like morphology. Such catalysts are described in WO 00/74845, which is hereby incorporated into this application by reference.
  • M 1 is Zn 2+ and M 2 is Co 3+ , i.e. the multimetal cyanide compound is a zinc hexacyanocobaltate .
  • the multimetal cyanide compound is a zinc hexacyanocobaltate .
  • crystalline multimetal cyanide compounds in which the anion X is formate, acetate or propionate and f is greater than 0, and which exhibit X-ray diffractograms as are described in DE 197 42 978 Al, which is hereby incorporated into this application by reference.
  • preference is in turn given to those in which the anion X is acetate and in particular those which crystallize in a monoclinic crystal system.
  • Crystalline DMC catalysts which can be used in the process according to the invention are also described in US 6, 303,833 Bl, US 6,613,714 B2, US 6, 689, 710 B2 ,
  • DMC catalysts has the advantage that the addition reaction of alkylene oxides proceeds at a relatively high reaction rate and the formation of undesired by-products is reduced compared to alkali metal hydroxide catalysis.
  • the heat of reaction which forms during the alkoxylation can be dissipated either by an internal heat exchanger or else by an external one, or by means of a combination of the two.
  • an external heat exchanger the reaction contents are fed to and discharged from the heat exchanger by pumped circulation.
  • the sum of the contents of organohalogen compounds, in particular chlorine compounds and bromine compounds, determined according to DIN 51408-2 and EN ISO 10304, is not more than 150 ppm, for example not more than 60 ppm, or even not more than 30 ppm; the sum of the contents of aldehydes and ketones, determined according to VDI 3862 Part 2, is not more than 300 ppm, for example not more than 120 ppm, or even not more than 60 ppm; the content of allyl alcohol, determined by means of gas chromatography analogously to DIN 51405, is not more than 8500 ppm, for example not more than 3400 ppm, or even not more than 1700 ppm; and the content of hydrocarbons, determined by means of gas chromatography analogously to DIN 51405 and expressed as the sum value, is not more than 500 ppm, for example not more than 200 ppm, or even not more than 100 ppm.
  • the propylene oxide has a halogen content of not more than 60 ppm, a content of aldehydes and ketones of not more than 120 ppm, a content of allyl alcohol of not more than 3400 ppm and a hydrocarbon content of not more than 200 ppm.
  • the propylene oxide has a halogen content of not more than 30 ppm, a content of aldehydes and ketones of not more than 60 ppm, a content of allyl alcohol of not more than 1700 ppm and a hydrocarbon content of not more than 100 ppm.
  • the propylene oxide has a water content, determined by Karl-Fischer titration according to DIN EN 13267, of not more than 500 ppm, for example not more than 200 ppm, or even not more than 100 ppm.
  • the propylene oxide has an acid content, expressed by the value determined by means of acid-base titration according to DIN EN 62021-2 or DIN 12634 and calculated for acetic acid, of not more than 100 ppm, for example not more than 40 ppm, or even not more than 20 ppm.
  • Propylene oxide suitable for use in the process according to the invention can be obtained, for example, by subjecting propylene oxide prepared by means of the epichlorohydrin process, the SM/PO process, the HPPO process or the MTBE/PO process to a purification process in which the content of the aforementioned compounds in the propylene oxide is reduced to concentrations below the critical threshold values.
  • impurities can be removed by extractive distillation of the propylene oxide, as is described, for example, in US 2005/082159 A, US 2003/102206,
  • the propylene oxide can also be treated with suitable adsorbents, as is taught, for example, in EP 0 675 119 A2 or GB 1,035,866 A, which are both hereby incorporated into the present application by reference.
  • Suitable methods for the purification of PO which has been prepared by means of the SM/PO process are, for example, treatment with ion exchange resins, as disclosed in US 5,107,007 A, or extractive distillation, as disclosed, for example, in US 3,909,366 A, which are both hereby incorporated into the present application by reference.
  • a suitable method is, for example, extractive distillation, as disclosed in US 5,006,206 A, which is hereby incorporated into the present application by reference, or in US 5,133,839 A.
  • a suitable method is, for example, fractional distillation with subsequent stripping of the side stream, as is proposed in US 3,398,062 A, which is hereby incorporated into the present application by reference .
  • a suitable method is, for example, extractive distillation, as disclosed in WO 2004/092150 Al, which is hereby incorporated into the present application by reference.
  • the starter polyol used was a polypropylene glycol with molar mass 400 which was prepared with KOH catalysis and from which the catalyst was removed by means of phosphoric acid precipitation, filtration and subsequent treatment with Ambosol ® , a commercially available magnesium silicate.
  • the DMC catalyst used was prepared as in EP 0 862 947 and employed as a solid.
  • phase 1 Into a 300 ml autoclave, 40 g of polypropylene glycol with OH number 100 and functionality 1.98 and 70 ppm of DMC catalyst (based on the final amount of the polyol) were introduced as initial charge. At 130°C and with stirring, flushing with nitrogen was carried out twice at 5 bar. 7 bar of nitrogen was then applied for 20 min. The system was then held under vacuum for 25 min. In phase 1 of the test, with stirring, 4.8 ml of in total 151 g of PO were introduced at 2.5 ml/min at 130°C and max. 4 bar. Phase 2 followed when the exothermic initiation reaction had subsided and the pressure had dropped below 0.7 bar; if not, phase 1 was repeated.
  • phase 2 at 100°C and initially vacuum, the remaining PO was added over the course of 22 min, the introduction rate being increased in stages from 0 to 5.0 ml/min; during this, a pressure from 1.9 to 5.5 bar was established. A post-reaction time of 60 min then followed. The mixture was worked-up as follows: holding at vacuum for 25 min at 100°C, then cooling to 25°C and flushing with 2 bar of nitrogen. OH number and viscosity were determined for the product (theoretical OH number: 22 mg KOH/g) .
  • the initiation time is in some cases significantly extended, the extent of the extension depending on the concentration of the troublesome substance in question. In some cases, no reasonable yield is achieved and deviations in the product properties result.
  • Test A results of Test A, (initiation time, T max and p ma x) and Test B (yield, OH number and

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Toxicology (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Polyethers (AREA)

Abstract

La présente invention porte sur un procédé perfectionné permettant de préparer des alcools de polyéthers au moyen d'une catalyse par un DMC, sur les alcools de polyéthers préparés avec le procédé et sur leur utilisation, en particulier pour la production de polyuréthanes.
PCT/EP2010/007641 2010-01-15 2010-12-15 Procédé pour la préparation de polyols catalysée par un dmc WO2011085772A1 (fr)

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SG2012039707A SG181448A1 (en) 2010-01-15 2010-12-15 "process for the dmc-catalyzed preparation of polyols"

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EP10000350.8 2010-01-15
EP10000350 2010-01-15

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9120731B2 (en) 2010-08-09 2015-09-01 Basf Se Process for preparing polyether alcohols
CN106248807A (zh) * 2015-06-10 2016-12-21 中国石油天然气股份有限公司 丙烯氧化反应液相产物中乙酸含量的分析方法
US10258953B2 (en) 2016-08-05 2019-04-16 Covestro Llc Systems and processes for producing polyether polyols

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EP0540225A1 (fr) 1991-11-01 1993-05-05 Texaco Chemical Company Purification de l'oxyde de propylène par distillation extractive
EP0675119A2 (fr) 1994-03-28 1995-10-04 Texaco Development Corporation Préparation d'oxyde de propylène substantiellement anhydre
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