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WO1996020234A1 - Procede de decyclisation d'epoxydes - Google Patents

Procede de decyclisation d'epoxydes Download PDF

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Publication number
WO1996020234A1
WO1996020234A1 PCT/EP1995/005003 EP9505003W WO9620234A1 WO 1996020234 A1 WO1996020234 A1 WO 1996020234A1 EP 9505003 W EP9505003 W EP 9505003W WO 9620234 A1 WO9620234 A1 WO 9620234A1
Authority
WO
WIPO (PCT)
Prior art keywords
carbon atoms
acid
linear
epoxy
formula
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/EP1995/005003
Other languages
German (de)
English (en)
Inventor
Peter Daute
Roland Grützmacher
Hermann Kluth
Nicole Mertscheit
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Henkel AG and Co KGaA
Original Assignee
Henkel AG and Co KGaA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Publication of WO1996020234A1 publication Critical patent/WO1996020234A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

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
    • C08G65/2669—Non-metals or compounds thereof
    • C08G65/2684—Halogens or compounds thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B41/00—Formation or introduction of functional groups containing oxygen
    • C07B41/04—Formation or introduction of functional groups containing oxygen of ether, acetal or ketal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/31—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by introduction of functional groups containing oxygen only in singly bound form
    • 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
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/36—Hydroxylated esters of higher fatty acids
    • 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
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
    • C08G59/687—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used containing sulfur
    • 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
    • C08G65/2669—Non-metals or compounds thereof
    • C08G65/2678—Sulfur or compounds thereof

Definitions

  • the invention relates to a process for reacting epoxy compounds with nucleophiles in the presence of fluoroalkanesulfonic acids, and to the use of the ring-opening products for the production of polymers.
  • the ring opening of epoxides with nucleophiles is known, e.g. from DE-Al 32 46 612, which describes a process for the production of modified triglycerides, in which epoxidized fats or oils are reacted with mono- or polyhydric alcohols in the presence of sulfuric acid, phosphoric acid or sulfonic acids.
  • a method is known from DS-A 5,002,678 for reacting halogenated alcohols with alkylene oxides, in which the alcohol, e.g. Trifluoroethanol, in a first stage in the presence of a Lewis acid, is reacted with propylene oxide in order to then be further propoxylated in the presence of another catalyst.
  • Trifluoromethanesulfonic acid is also mentioned as a usable Lewis acid.
  • the prior art processes for ring opening of epoxides all have the disadvantage that the various acidic catalysts, but especially sulfuric acid, lead to discoloration of the reaction products when the ring is opened. If medium-strength acids such as phosphoric acid, phosphorous or hypophosphorous acids are used, light-colored products are obtained, for larger ring opening of the epoxy groups either larger amounts of catalyst have to be added or the reaction times are extremely prolonged.
  • the object of the invention was therefore to develop a process for the preparation of epoxy ring opening products which provides ring opening products with improved, lighter color and fewer by-products, such as keto compounds, after shorter reaction times.
  • the invention relates to a process for the ring opening of epoxy compounds with nucleophiles, in which the reaction is carried out in the presence of fluoroalkanesulfonic acids as a catalyst.
  • Fluoroalkanesulfonic acids are organic sulfonic acids with 1 to 12 carbon atoms, which contain at least 1 fluorine atom in the organic radical.
  • Completely fluorinated alkanesulfonic acids such as perfluorooctanesulfonic acid or perfluoroethanesulfonic acid, are preferred. Trifluoromethanesulfonic acid is particularly preferred.
  • the fluoroalkanesulfonic acids are preferably used in free form.
  • the amount of fluoroalkanesulfonic acids used can be 5 to 1,000, preferably 10 to 200 and in particular 15 to 100 ppm, based on the weight of the starting materials.
  • Epoxy compounds are known substances and can be obtained by processes known per se by epoxidation of unsaturated feedstocks. Examples include the reaction of olefins with peracetic acid in the presence of acidic catalysts [DE-Al 857 364] or with performic acid formed in situ from formic acid and hydrogen peroxide [US Pat. No. 2,485,160]. To carry out the process according to the invention, it is a prerequisite that a substantial proportion, for example 2 to 40, preferably 4 to 8.5% by weight of epoxy acid is present in the epoxy compounds. This includes the fact that not only completely but also partially epoxidized substances can be used in the sense of the method according to the invention.
  • Epoxy compounds are understood to mean compounds from the group of the al) glycidyl ethers, a2) olefin epoxides, a3) epoxidized esters of unsaturated fatty acids, a4) epoxidized esters of unsaturated fatty alcohols and a5) epoxidized triglycerides. These groups each represent preferred embodiments of the invention.
  • Glycidyl ethers are understood to mean ethers of glycidyl alcohol with aliphatic or aromatic alcohols, which are obtained by reacting epichlorohydrin with the alcohols are accessible. Examples of these are 1,6-hexanediol diglycidyl ether or 1,4-butanediol diglycidyl ether.
  • the glycidyl ethers of bisphenol A and its higher condensation products formed by self-condensation are particularly preferred.
  • R1_CH CH-R 2 (I)
  • R 1 is a linear or branched aliphatic hydrocarbon radical having 1 to 18 carbon atoms and R ⁇ is hydrogen or a linear or branched hydrocarbon radical having 1 to 8 carbon atoms, with the proviso that the sum of the carbon atoms from R 1 and R- * is at least 8.
  • Typical examples are the epoxides of Octen-1, Decen-1, Dodecen-1, Tetradecen-1, Octadecen-1 or Octadecen-9.
  • Preferred are epoxides of olefins of the formula (I) in which the sum of R 1 and R 2 is from 8 to 16 and the R 2 is hydrogen.
  • R 3 C0 represents an aliphatic acyl radical having 16 to 24 carbon atoms and 1 to 5 double bonds
  • R 4 represents a linear or branched alkyl radical having 1 to 4 carbon atoms.
  • Typical examples are the epoxides of palmitoleyl acid methyl ester, oleic acid methyl ester, elaidic acid methyl ester, petroselinic acid methyl ester, linoleic acid methyl ester or erucic acid methyl ester.
  • Epoxides of esters of the formula (II) are preferred, in which R 3 CO is an aliphatic hydrocarbon radical having 18 to 22 carbon atoms and 1 or 2 double bonds and R 4 is a methyl group.
  • R ⁇ CO represents an aliphatic acyl radical having 1 to 24 carbon atoms and 0 or 1 to 5 double bonds and R *> represents a linear or branched aliphatic hydrocarbon radical having 16 to 24 carbon atoms and 1 to 5 double bonds.
  • Typical examples are epoxides of ethyl acetate, oleic acid oleic acid or erucic acid ethyl ester.
  • Epoxides of esters of the formula (III) are preferred in which R 5 CO is an aliphatic acyl radical having 18 to 22 carbon atoms and 1 or 2 double bonds and R *> is an aliphatic hydrocarbon radical having 16 to 22 carbon atoms and 1 or 2 double bonds.
  • R 7 CO for a linear or branched aliphatic acyl radical with 16 to 24 carbon atoms and 1 to 5 double bonds
  • R O CO and R 9 CO independently of one another for a linear or branched aliphatic acyl radical with 6 to 22 carbon atoms and 0 or 1 up to 5 double bonds and their mixtures.
  • Typical examples are epoxides of peanut oil, coriander oil, cottonseed oil, olive oil, linseed oil, beef tallow, fish oil or in particular soybean oil.
  • R 7 CO, R 8 CO and R ⁇ CO independently of one another represent aliphatic acyl radicals having 18 to 22 carbon atoms and predominantly 1 or 2 double bonds.
  • Preferred nucleophiles which are required for the ring opening of the epoxy compounds are hydroxyl-containing compounds from the group bl) water, b2) monofunctional alcohols, b3) polyhydric alcohols, b4) fatty alcohol polyglycol ethers and b5) carboxylic acids:
  • R 1 ⁇ represents linear or branched aliphatic hydrocarbon radicals having 1 to 22 carbon atoms and 0 or 1 to 3 double bonds.
  • Typical examples are methanol, ethanol, propanol-1, propanol-2, n-butanol, pentanol, hexanol, octanol, decanol, lauryl alcohol, myristyl alcohol, cetyl alcohol, stearyl alcohol, oleyl alcohol, behenyl alcohol or erucyl alcohol.
  • the use of methanol and ethanol is preferred.
  • polyhydric alcohols e.g. Ethylene glycol, diethylene glycol, polyethylene glycols in the molecular weight range 300 to 1500, 1,2-propanediol, 1,3-propanediol, glycerol, oligoglycerols with degrees of condensation of 2 to 10 on average, trimethylolpropane, pentaerythritol, sorbitol and sorbitan.
  • Ethylene glycol, propane-1,2-diol, glycerol and trimethylol propane are preferred.
  • R ⁇ represents linear or branched aliphatic hydrocarbon radicals having 6 to 22 carbon atoms and 0 or 1 to 3 double bonds
  • R 12 represents hydrogen or a methyl group and n represents numbers from 1 to 30.
  • Typical Examples are adducts of an average of 1 to 30 mol of ethylene and / or propylene oxide with 1 mol of hexanol, octanol, decanol, lauric alcohol, myristyl alcohol, cetyl alcohol, stearyl alcohol, oleyl alcohol, behenyl alcohol or erucyl alcohol.
  • Preference is given to using fatty alcohol polyglycol ethers of the formula (VI) in which R 11 represents alkyl radicals having 6 to 18 carbon atoms, R 12 represents hydrogen and n represents numbers from 1 to 10.
  • R 3 represents a linear or branched hydrocarbon radical having 1 to 22 carbon atoms.
  • carboxylic acids are formic acid, acetic acid, propionic acid, fatty acids with 6 to 22 carbon atoms and benzoic acid or mixtures thereof.
  • Preferred nucleophiles are alcohols, with the polyvalent ones being particularly preferred.
  • the epoxy compounds and the nucleophiles can be used in molar ratios of 1:10 to 10: 1, preferably 1: 3 to 3: 1. In the case of polyhydric alcohols in particular, it is particularly preferred to maintain a ratio which is approximately in the range of equivalence.
  • the ring opening can take place in a manner known per se, it having proven advantageous to add the reaction the boiling point of the nucleophile used or in the temperature range from 60 to 250 ° C. at normal pressure. It is not absolutely necessary for the ring opening to proceed completely. Rather, it is also possible to produce epoxy ring opening products which still have a defined residual content of epoxy oxygen, for example 1 to 3% by weight.
  • the reaction times are generally between 1 and 6 hours.
  • the catalyst can be removed by customary processes, for example by adsorption on a solid material, or can remain in the product after neutralization with alkalis such as NaOH, KOH, LiOH or a2CO3 or amines such as ethanol in, morpholine or ammonia.
  • the epoxy ring opening products obtainable by the process according to the invention are suitable inter alia as raw materials for the production of polymers.
  • they can be condensed in alkyd resins both via the hydroxyl functions and via epoxy groups still in the molecule and represent polyfunctional polycondensation building blocks of the kind which are particularly important for the development of polyurethane foams.
  • Another object of the invention therefore relates to the use of the epoxy ring opening products according to the invention for the production of polymers.
  • they are present in the polymers in an amount of 1 to 90, preferably 10 to 70,% by weight, based on the polymers.
  • Preferred polymers are the polyurethanes, in particular polyurethane foams or coatings, which by reaction of polyfunctional isocyanates with the Hydroxyl groups of the ring opening products according to the invention are easily accessible.
  • the acid number (SZ) was determined according to DIN 53402.
  • the hydroxyl number (OHZ) was determined according to DIN 53240.
  • the ketone number (COZ) was determined according to the method of the German Society for Fat Research C-V 18 [53].
  • the color was determined by the Lovibond method (German Society for Fat Research C-V 4b [84]).
  • 1,4-butanediol 450 g were heated to 90 ° C. with stirring and 0.25 g of a 10% strength aqueous solution of trifluoromethanesulfonic acid was added. Thereafter, 818 g of epoxystearic acid methyl ester (4.89% by weight of epoxy oxygen) were added dropwise within 75 minutes. The initially exothermic reaction was ended 30 minutes after the dropwise addition (0.07% by weight epoxy oxygen).
  • the catalyst acid was neutralized with 0.5 g of ethylenediamine + 4 PO and the excess 1,4-butanediol was distilled off in vacuo (up to p about 0.5 mbar).
  • the comparative example shows that perchloroacetic acid, another extremely strong acid, at the same concentration is not as effective as the trifluoromethanesulfonic acid according to the invention.
  • Comparative example 5 was repeated. 0.33 g of a 10% solution of methyl trifluoromethanesulfonate in di-n-octyl ether was used as the catalyst.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Epoxy Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

Selon un procédé de décyclisation de composés époxydes avec des nucléophiles, la réaction est effectuée en présence d'acides alcane-sulfoniques fluorés, notamment l'acide trifluorométhane-sulfonique, qui servent de catalyseurs.
PCT/EP1995/005003 1994-12-27 1995-12-18 Procede de decyclisation d'epoxydes Ceased WO1996020234A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19944446877 DE4446877A1 (de) 1994-12-27 1994-12-27 Verfahren zur Ringöffnung von Epoxiden
DEP4446877.6 1994-12-27

Publications (1)

Publication Number Publication Date
WO1996020234A1 true WO1996020234A1 (fr) 1996-07-04

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PCT/EP1995/005003 Ceased WO1996020234A1 (fr) 1994-12-27 1995-12-18 Procede de decyclisation d'epoxydes

Country Status (2)

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DE (1) DE4446877A1 (fr)
WO (1) WO1996020234A1 (fr)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009101141A1 (fr) * 2008-02-15 2009-08-20 Basf Se Polyéthérols hautement fonctionnels et leur production et utilisation
EP2161295A1 (fr) * 2008-09-05 2010-03-10 Basf Se Polyéthérols hautement fonctionnels ainsi que leurs fabrication et utilisation
US20120022186A1 (en) * 2009-05-14 2012-01-26 Craun Gary P Hydroxyl functional oil polyols and coating compositions prepared from hydroxyl functional oil polyols
US20140213677A1 (en) * 2011-10-14 2014-07-31 Dow Global Technologies Llc Hybrid polyester-polyether polyols for improved demold expansion in polyurethane rigid foams
US9260625B2 (en) 2011-12-21 2016-02-16 Akzo Nobel Coatings International B.V. Water-based coating compositions
US9273226B2 (en) 2011-12-21 2016-03-01 Akzo Nobel Coatings International B.V. Solvent-based coating compositions
WO2017162529A1 (fr) 2016-03-21 2017-09-28 Basf Se Polyuréthane réticulé
US11066508B2 (en) 2014-08-18 2021-07-20 Basf Se Polyester-modified polybutadienols for producing polyurethane elastomers and thermoplastic polyurethanes

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19646424A1 (de) 1996-11-11 1998-05-14 Henkel Kgaa Verwendung von Polyolen für Isocyanat-Gießharze und -Beschichtungsmassen
EP2090606A1 (fr) * 2008-02-15 2009-08-19 Basf Se Polyéthérols hautement fonctionnels ainsi que leurs fabrication et utilisation
WO2011151775A1 (fr) 2010-05-31 2011-12-08 Basf Se Polyazoles mécaniquement stabilisés
WO2013017417A1 (fr) 2011-07-29 2013-02-07 Basf Se Retardateur de flamme polymère
WO2014044529A1 (fr) 2012-09-20 2014-03-27 Basf Se Esters de l'acide phosphorique hyperramifiés
US11951083B2 (en) * 2022-06-08 2024-04-09 Cytometix, Inc. Methods of manufacturing 14,15-epoxyeicosatrienoic acid analogs and improved therapeutic delivery of same

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0139042A2 (fr) * 1983-10-27 1985-05-02 Union Carbide Corporation Produits d'addition de basse viscosité d'un composé organique à hydrogènes actifs et d'un polyépoxyde
US5002678A (en) * 1990-06-29 1991-03-26 Olin Corporation Lubricants for heat transfer fluids
WO1995017445A1 (fr) * 1993-12-21 1995-06-29 The Dow Chemical Company Procede de reaction de composes contenant des epoxydes avec des alcools aliphatiques

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0139042A2 (fr) * 1983-10-27 1985-05-02 Union Carbide Corporation Produits d'addition de basse viscosité d'un composé organique à hydrogènes actifs et d'un polyépoxyde
US5002678A (en) * 1990-06-29 1991-03-26 Olin Corporation Lubricants for heat transfer fluids
WO1995017445A1 (fr) * 1993-12-21 1995-06-29 The Dow Chemical Company Procede de reaction de composes contenant des epoxydes avec des alcools aliphatiques

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009101141A1 (fr) * 2008-02-15 2009-08-20 Basf Se Polyéthérols hautement fonctionnels et leur production et utilisation
US8946377B2 (en) 2008-02-15 2015-02-03 Basf Se Highly functional polyetherols and the production and use thereof
EP2161295A1 (fr) * 2008-09-05 2010-03-10 Basf Se Polyéthérols hautement fonctionnels ainsi que leurs fabrication et utilisation
US9133292B2 (en) 2009-03-05 2015-09-15 Akzo Nobel Coatings International B.V. Hydroxyl functional oil polyol acrylic graft copolymers
US20120022186A1 (en) * 2009-05-14 2012-01-26 Craun Gary P Hydroxyl functional oil polyols and coating compositions prepared from hydroxyl functional oil polyols
US20140213677A1 (en) * 2011-10-14 2014-07-31 Dow Global Technologies Llc Hybrid polyester-polyether polyols for improved demold expansion in polyurethane rigid foams
US9260625B2 (en) 2011-12-21 2016-02-16 Akzo Nobel Coatings International B.V. Water-based coating compositions
US9273226B2 (en) 2011-12-21 2016-03-01 Akzo Nobel Coatings International B.V. Solvent-based coating compositions
US11066508B2 (en) 2014-08-18 2021-07-20 Basf Se Polyester-modified polybutadienols for producing polyurethane elastomers and thermoplastic polyurethanes
WO2017162529A1 (fr) 2016-03-21 2017-09-28 Basf Se Polyuréthane réticulé

Also Published As

Publication number Publication date
DE4446877A1 (de) 1996-07-04

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