WO2009100854A2 - Procédé de production d'acétals - Google Patents

Procédé de production d'acétals Download PDF

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Publication number
WO2009100854A2
WO2009100854A2 PCT/EP2009/000822 EP2009000822W WO2009100854A2 WO 2009100854 A2 WO2009100854 A2 WO 2009100854A2 EP 2009000822 W EP2009000822 W EP 2009000822W WO 2009100854 A2 WO2009100854 A2 WO 2009100854A2
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WO
WIPO (PCT)
Prior art keywords
acetals
mmol
toluene
phosphines
olefin
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/EP2009/000822
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German (de)
English (en)
Inventor
Matthias Beller
Udo Kragl
Eckhard Paetzold
Lorenz Neubert
Patrick Kollmorgen
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Cognis IP Management GmbH
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Cognis IP Management GmbH
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Publication of WO2009100854A2 publication Critical patent/WO2009100854A2/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
    • C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
    • C07D317/20—Free hydroxyl or mercaptan
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/02—Liquid carbonaceous fuels essentially based on components consisting of carbon, hydrogen, and oxygen only
    • C10L1/026—Liquid carbonaceous fuels essentially based on components consisting of carbon, hydrogen, and oxygen only for compression ignition
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/185—Ethers; Acetals; Ketals; Aldehydes; Ketones
    • C10L1/1852—Ethers; Acetals; Ketals; Orthoesters
    • C10L1/1855—Cyclic ethers, e.g. epoxides, lactides, lactones
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
    • C10M105/10—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
    • C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
    • C10M129/16—Ethers
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
    • C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
    • C10M129/16—Ethers
    • C10M129/20—Cyclic ethers having 4 or more ring atoms, e.g. furans, dioxolanes
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2072—Aldehydes-ketones
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
    • C10G2300/10—Feedstock materials
    • C10G2300/1011—Biomass
    • C10G2300/1014—Biomass of vegetal origin
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
    • C10M2207/0406—Ethers; Acetals; Ortho-esters; Ortho-carbonates used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/06—Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
    • 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
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P30/00—Technologies relating to oil refining and petrochemical industry
    • Y02P30/20—Technologies relating to oil refining and petrochemical industry using bio-feedstock

Definitions

  • the invention relates to a process for the preparation of acetals and their use as fuels or as fuel additives, as solvents or as detergents.
  • Polylols are characterized by multiple hydroxy groups. Glycol, glycerol, erythritol, 1,2- and 1,3-propanediol are to serve as examples of polyols (no sugars).
  • the currently most important polyol glycerine is obtained from the saponification of natural fats and oils and in biodiesel production to a greatly increasing extent. There is an urgent need to identify variants for the sustained cost-effective application of the expected overproduction of glycerol (Plagliaro, M. et al., Angew Chem., 2007, 119, 4516-4522).
  • glycerol catalytically
  • First the decomposition in synthesis gas
  • second the conversion of one or more hydroxy groups to new functional groups.
  • the conversion of the hydroxy groups can be carried out biologically or chemically. Since glycerol is a multi-million-tonne resource, one goal of the material transformation is to be the bulk product of making low-cost consumer goods.
  • the glycerol conversion situation is described by M. Pagliaro et al. Angew. Chem., 2007, 119, 4516 - 4522 illuminated.
  • Glycerol CH 2 OH-CHOH-CH 2 OH, characterized by its extremely high hydrophilicity, can not be significantly higher in its previous applications. Glycerol itself can not be used as fuel for engines (high temperature polymerization, high boiling point, lower)
  • the variant glycerol is to implement with olefins or olefin mixtures.
  • olefins or olefin mixtures One possibility of this type is the reaction with isobutene and the formation of monomeric and higher glycerol t-butyl ethers.
  • Olefins / olefin mixtures is also known. (Behr, A., et al., Chem. Ing. Techn., 2007, 79,
  • Hydroformylation is the most important industrially used homogeneous catalytic synthesis for the preparation of aldehydes (about 9 - 10 milliliters t / a predominantly for PVC plasticizers).
  • the most commonly used alkene is propene and only the 1-butanal can be used for plasticizer main application.
  • the isobutanal also obtained in the hydroformylation is a difficult-to-sell by-product. Longer chain aldehydes are more costly and have limited availability.
  • Isobutanal reacts with glycol, 1,2-propanediol, 1,3-propanediol, glycerol, erythritol to form acetals to synthesize 5-, 6- and 7-ring acetals, preferably 5- and 6-membered rings (Scheme 1).
  • the C chain of the glycerol product after the reaction to the monoacetal is in the simplest case seven C atoms long.
  • product formation is possible even with complete conversion of all three hydroxy groups to acetals when working with an excess of aldehyde, forming the products from two glycerol molecules and three aldehydes.
  • the disadvantage of the known processes is that a promising reaction of polyols with alkenes leads only to ethers under medium pressures or the alkanals as starting materials to products, which is exactly extended by the C chain length of the respective educts.
  • Transition metal complex catalysts an extension by one carbon atom of the olefins while increasing their reactivity occurs and then synthesized aldehydes then allow a reaction with polyols to acetals.
  • aldehydes are synthesized by means of an upstream hydroformylation with transition-metal complex catalysts, which are acetalized in a subsequent reaction with polyols under acidic conditions.
  • a first subject of the present application relates to a process for the preparation of acetals from polyols, wherein hydroformylated olefins in the presence of transition metal-phosphine or -phosphite complex catalysts in a multiphase systems to aldehydes and the resulting aldehydes with polyols under acidic conditions in acetals wherein the reaction is carried out at temperatures between 25 and 200 ° C, and for the complex catalysts, the molar Transition metal / phosphorus ratios between 1: 0.5 and 1: 100, characterized in that the steps (a) and (b) takes place in a reaction vessel without separation of intermediates.
  • An essential element of the process according to the invention is that steps (a) and (b) are carried out in a reaction vessel without separation of intermediates.
  • the process thus results in a combination of both reactions in a one-pot synthesis process, so that both reactions can be carried out one behind the other in a reaction vessel.
  • aldehydes are hydroformylated, which in the subsequent reaction with polyols z. B. form acetals with polyols.
  • These products have their significance as gasoline or diesel fuels, detergents, cosmetics and additives for lubricants. Furthermore, as solvents, plasticizers, stabilizers, pharmaceuticals, fungicides and microbicides, flavorings, intermediates and as additives for various applications.
  • the transition metal complexes of the eighth subgroup can be used according to the invention as catalysts.
  • the elements cobalt and rhodium can be used in different oxidation states as cobalt (I), cobalt (II) - or as rhodium (I) -, rhodium (II) - and rhodium (III) compound.
  • cobalt (I) and rhodium (I) complexes as precursors for the catalyst species of the valence state +1 forming during the reaction is particularly favorable.
  • the molar concentration of the transition metal to the olefin should be between 1 to 10 to 1 to 1 000 000, preferably between 1 to 100 to 1 to 100 000.
  • the phosphines for the catalytic reaction may be all known from the relevant literature chiral and achiral, hydrophilic and hydrophobic phosphines and diphosphines, especially all alkyl, alkenyl, alkoxy, aryl, substituted
  • Particularly preferred complex catalysts for step (a) are phosphines and diphosphines which contain one or more alkyl or arylsulfonic acids or their salts as hydrophilic species, and in particular sulfoaryl, sulfoarylalkyl and sulfoalkylphosphines such as TPPMS, TPPTS, bis-1, r -phenyl-2,2 '- [CH 2 -P (Ph) (CH 2 ) 3 SO 3 M] 2; bis-naphthyl-2,2 '- [CH 2 -P (Ph) (CH 2 ) 3 SO 3 M] 2 PPh 2 (2-SO 3 M, 5-C 12 H 25 , -C 6 H 3 -) , Ph 2 P (CH 2 ) 3 SO 3 M, Ph 2 P (CH 2 ) 4 SO 3 M, Ph 2 PCH 2 C 6 H 4 -2-SO 3 M, Ph 2 P (CH 2 ) 2 S ( CH 2
  • the molar transition metal / phosphine ratios can be from 1: 0.5 to 1: 100, preferably between 1: 1 and 1: 20.
  • multiphase systems in which the hydrofomylation can be carried out are polar / apolar multiphase solvent systems, especially with DMF, THF, diethyl ether, dimethyl ether, DMSO, methanol, ethanol, propanol, hexane, heptane, octane, decane, benzene, toluene, xylene , Petroleum benzine and mixtures, carbon tetrachloride, chloroform, dichloromethane, trichlorethylene, dichloroethane, acetone, acetonitrile and ethyl acetate, together with polyols and water, in application.
  • protonic acids especially HCl, H 2 SO 3 , H 2 SO 4 , H 3 PO 4 but also ion exchangers, are used.
  • concentration of acids is between 1 wt .-% and 100 ppb, preferably between 0.01 wt .-% and 100 ppm.
  • the temperatures may be between 25 and 200 0 C, preferably between 50 and 150 ° C, are. Preferred ranges are between 25 and 150 ° C, preferably between 30 and 100 0 C and in particular between 35 and 80 0 C.
  • the method is preferably designed as a one-pot multiphase systems, wherein no further solvents must be used in the polar / apolar multiphase system. The procedure without solvent is thus preferred.
  • the reactions are preferably carried out under carbon monoxide / hydrogen atmosphere in a ratio CO: H 2 of preferably 1:10 to 10: 1, preferably from 1: 3 to 3: 1.
  • the total pressure can be between one and 300 bar, preferably between one and 100 bar, amount.
  • olefins of C 6 to Cj 2 are generally used under phase transfer conditions with phosphine-transition metal complexes.
  • the products obtained are n- or iso-aldehydes.
  • Olefins in the narrower sense can be pure 1-olefins, pure internal olefins, internal olefins, especially as cis or trans isomeric olefins, but also technical olefin mixtures.
  • Ethylene glycol, 1, 2-propanediol, 1,3-propanediol, glycerol, erythritol and mixtures thereof are to be regarded as examples of polyols for the purposes of this invention, but no sugars.
  • reaction sequence according to the invention namely by the hydroformylation of olefins to aldehydes and their subsequent conversion to acetals, compounds can be prepared which are extended in the carbon chain an extension by one carbon from the hydroformylation and by the number of carbon atoms of the polyol.
  • acetal formation reduces the number of hydroxy groups by at least two. Products with lower boiling points and significantly higher calorific value than the polyol are synthesized.
  • acetals so prepared can be used as solvents, detergents, in cosmetics or as other technical additives, e.g. in lubricants or hydraulic oils.
  • Another object of the application relates to the use of acetals, which have been prepared according to the method described above as a fuel for internal combustion engines or as an additive to fuels for internal combustion engines, preferably fuels based on hydrocarbons and in particular as an additive to gasoline or diesel fuels or in Kerosene, wherein use in biodiesel may be preferred.
  • the acetals prepared according to the invention may be present in the fuels preferably in amounts of from 1 to 99% by weight, with amounts of from 5 to 60% by weight and in particular from 10 to 50% by weight being particularly preferred.
  • the use of the acetals as solvents, detergents or in cosmetics, for example as an oil component or as an emulsifier claimed.
  • Another object of the application relates to the use of acetals, prepared according to the above as a lubricant, or additive in lubricants and preferably as a so-called. Friction modifier. embodiments
  • Olefin / Rh 50,000

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
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  • Emergency Medicine (AREA)
  • Engineering & Computer Science (AREA)
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  • Epidemiology (AREA)
  • Dermatology (AREA)
  • Wood Science & Technology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne un procédé permettant de produire des acétals et leur utilisation comme combustibles ou comme auxiliaires combustibles, comme solvants ou comme détergents à base de polyols, par une succession de deux réactions selon le procédé de réaction monotope: d'une part, par hydroformylation d'oléfines avec des catalyseurs complexes métal de transition-phosphine dans des systèmes à plusieurs phases. La réaction de formation de liaisons C-C s'effectue dans le mélange de plusieurs phases en présence de phosphines et de diphosphines avec des éléments de sous-groupes tels que le cobalt ou le rhodium à des températures comprises entre 0 et 200°C. Pour les catalyseurs complexes, les rapports molaires métal de transition/phosphine sont compris entre 1:05 et 1:100. D'autre part, les acétals sont obtenus en mode monotope, par réaction consécutive des aldéhydes synthétisés avec des polyols dans des conditions acides. La chaîne carbone de l'oléfine est prolongée de plus d'un atome de C que celle du polyol utilisé, pour augmenter l'indice de combustion des produits et abaisser la température de vaporisation par rapport au polyol. L'utilisation d'oléfines > C3 lors de l'hydroformylation permet d'obtenir des résultats qui satisfont aux exigences d'ordre industriel, notamment en ce qui concerne l'acétalisation de la glycérine.
PCT/EP2009/000822 2008-02-14 2009-02-06 Procédé de production d'acétals Ceased WO2009100854A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102008009103A DE102008009103A1 (de) 2008-02-14 2008-02-14 Verfahren zur Herstellung von Acetalen
DE102008009103.0 2008-02-14

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Publication Number Publication Date
WO2009100854A2 true WO2009100854A2 (fr) 2009-08-20

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2953828A1 (fr) * 2009-12-16 2011-06-17 Inst Francais Du Petrole Procede de fabrication d'additifs pour base carburant en une etape par hydroformylation d'une charge contenant au moins une olefine en presence d'au moins un alcool
RU2708256C1 (ru) * 2018-11-06 2019-12-05 Дмитрий Николаевич Горбунов Способ функционализации полиолов путем тандемной реакции гидроформилирования-ацетализации с применением водорастворимой каталитической системы
CN112876395A (zh) * 2021-01-15 2021-06-01 万华化学集团股份有限公司 一种维生素a醋酸酯的制备方法

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2436681A1 (fr) * 2010-09-06 2012-04-04 Cognis IP Management GmbH Dérivation de mélanges d'hydroxy-acétales et d'acétales
CN112679554B (zh) * 2020-12-31 2022-11-29 昆明贵金属研究所 制备铑(I)酸盐[RhL2]+A-及[RhI(CO)2Cl]2络合物的方法

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IL97364A (en) 1991-02-26 1994-07-31 Ramot Arie Chair

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2953828A1 (fr) * 2009-12-16 2011-06-17 Inst Francais Du Petrole Procede de fabrication d'additifs pour base carburant en une etape par hydroformylation d'une charge contenant au moins une olefine en presence d'au moins un alcool
RU2708256C1 (ru) * 2018-11-06 2019-12-05 Дмитрий Николаевич Горбунов Способ функционализации полиолов путем тандемной реакции гидроформилирования-ацетализации с применением водорастворимой каталитической системы
CN112876395A (zh) * 2021-01-15 2021-06-01 万华化学集团股份有限公司 一种维生素a醋酸酯的制备方法

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