EP2545026A1 - Procédé de préparation de diesters d'acides alpha, oméga-dicarboxyliques linéaires - Google Patents

Procédé de préparation de diesters d'acides alpha, oméga-dicarboxyliques linéaires

Info

Publication number
EP2545026A1
EP2545026A1 EP10782585A EP10782585A EP2545026A1 EP 2545026 A1 EP2545026 A1 EP 2545026A1 EP 10782585 A EP10782585 A EP 10782585A EP 10782585 A EP10782585 A EP 10782585A EP 2545026 A1 EP2545026 A1 EP 2545026A1
Authority
EP
European Patent Office
Prior art keywords
oil
acid
reaction
catalyst
group
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.)
Withdrawn
Application number
EP10782585A
Other languages
German (de)
English (en)
Inventor
Frank-Martin Petrat
Franz-Erich Baumann
Harald HÄGER
Guido Walther
Andreas Martin
Angela KÖCKRITZ
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.)
Evonik Operations GmbH
Original Assignee
Evonik Degussa GmbH
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 Evonik Degussa GmbH filed Critical Evonik Degussa GmbH
Publication of EP2545026A1 publication Critical patent/EP2545026A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/36—Preparation of carboxylic acid esters by reaction with carbon monoxide or formates
    • C07C67/38—Preparation of carboxylic acid esters by reaction with carbon monoxide or formates by addition to an unsaturated carbon-to-carbon bond

Definitions

  • the invention relates to a process for the preparation of linear alpha, omega-dicarboxylic acid diesters, especially linear alpha, omega-dicarboxylic acid dialkyl esters, by conversion of triglycerides in one
  • Alpha, omega-dicarboxylic acids and their esters are important industrial chemicals used, for example, in the synthesis of polyesters and polyamides. They are also used as lubricants and plasticizers for plastics.
  • the reaction is carried out at temperatures of - 30 ° C to 49 ° C and under a CO partial pressure of less than 30 x 10 5 Nm "2
  • the reaction process can be designed batchwise or continuously, as in WO 2007/020379 A1, for example is described.
  • Methyl linoleate or methyl linolenate can be obtained.
  • Monocarboxylic acid esters were the product of the reaction of olefins without further functional groups (D.J. Cole-Hamilton et al., Chem. Commun. (2004) 1720). With similar catalyst systems, short-chain olefins, such as, for example, ethylene, can be converted into carboxylic esters (WO 98/41495 A1, WO 96/19434 A1, US Pat.
  • catalyst systems for the preparation of carboxylic acid alkyl esters contain cobalt as active metal, pyridines or quinolines as additives, reaction temperatures of 100-180 ° C are required and only unsubstituted olefins are mentioned as substrates (US 3,507,891, US 3,976,670, SU952838, JP53-015310 ).
  • the catalyst system described was a combination of Cu (I) catalysts (EP 0 105 699 A1) or Cu (I) and Ag compounds (JP58-201748) and the expensive BF 3 .
  • the technical object of the invention is therefore to provide a process for the preparation of linear alpha, omega-dicarboxylic acid diesters, which makes it possible to produce the reaction product in a single reaction step directly from triglycerides at low cost.
  • Reaction step can be produced.
  • the technical object of the invention is achieved by a process for the preparation of linear alpha, omega-dicarboxylic acid diesters, preferably alpha, omega
  • the advantage of this method over the prior art is the saving of a reaction step and, associated therewith, a substantial simplification of the technical process of such a process. By simplifying the process, it can also be carried out at lower cost.
  • a further advantage of the process according to the invention is also that the catalyst can be used in smaller amounts than known in the prior art.
  • catalytic alkoxycarbonylation is feasible not only with fatty acid monoalkyl esters as starting materials, but also with high yields and high selectivity from corresponding triglycerides containing fatty acid residues with mono- or polyunsaturated carbon chains. It was surprising that these triglycerides are comparable in their reactivity in this catalytic reaction system with the reaction behavior of the fatty acid monoalkyl esters, which are used in the prior art as the starting material for the reaction.
  • the alpha, omega-dicarboxylic acid diesters can be obtained in a simple manner directly from triglycerides, which are preferably used as vegetable oils.
  • triglycerides which are preferably used as vegetable oils.
  • the previously necessary transesterification of the fatty acid glycerol esters to the corresponding fatty acid alkyl esters is eliminated.
  • linear alpha, omega-dicarboxylic acid diesters having a carbon chain length of C12 to C23, preferably C16 to C20, and particularly preferably cis and C19, are prepared.
  • triglycerides containing fatty acid residues with mono- or polyunsaturated carbons are vegetable oils used with monounsaturated or polyunsaturated fatty acid residues.
  • triglycerides selected from the group of sunflower oil, high oleic sunflower oil, rapeseed oil, rapeseed oil with high oleic acid or high erucic acid, olive oil, castor oil, sesame oil, soybean oil, corn oil, palm oil, linseed oil, walnut oil, wheat germ oil, grapeseed oil, evening primrose oil, thistle oil, peanut oil, hemp oil, jojoba oil, Tungöl, cottonseed oil and Jathrophaöl or mixtures thereof.
  • Highly acidic sunflower oil (HO sunflower oil) or rapeseed oil rich in high oleic acid or high erucic acid are particularly preferably used as vegetable oils.
  • the triglycerides contain at least 50% by weight, preferably at least 70% by weight and more preferably
  • High oleic sunflower oil contains at least 80% by weight of fatty acids.
  • High oleic rapeseed oil contains a fatty acid content of at least 50% by weight.
  • High erucic rapeseed oil contains a fatty acid content of at least 50% by weight.
  • the catalyst used is preferably a catalyst which contains an element of group VI IIb.
  • the catalyst is preferably a
  • the catalysts used preferably contain palladium and trivalent phosphorus ligands.
  • the ligands used are particularly preferably phosphines, phosphinites or phosphonites. These ligands may be mono- or bidentate ligands, wherein at least one ligand from the group of
  • Phosphine is present.
  • Particularly preferred ligands are bis (di-tert-butylphosphinomethyl) benzene and the following ligands: Bisphosphines with
  • R alkyl (especially tert-butyl
  • R alkyl (especially tert-butyl, cyclohexyl), aryl
  • R alkyl (especially tertiary) butyl, cyclohexyl), aryl
  • the palladium is used in the form of precursor compounds, such as palladium salts or other palladium complex compounds, in which two weakly coordinated ligands can be easily replaced by the trivalent phosphorus ligands. This is done in a possible pre-reaction of the catalyst or directly in combining the palladium component and the P (III) component in situ.
  • Examples of palladium compounds that can be used are:
  • OH group donors are preferably used linear and branched aliphatic alcohols having 1 to 10 carbon atoms or water and mixtures thereof.
  • Particularly preferred alcohols are methanol, ethanol, propanol and butanol. These alcohols can be used both as OH group donors and as solvents in the reaction. Particularly preferred is the use of methanol.
  • inert aprotic solvents can additionally be used.
  • these compounds are anisole, diethyl ether, methyl tert-butyl ether, methyl pentanoate, diphenyl ether, dimethyl adipate, tetrahydrofuran, dioxane,
  • Acids with a pK s value measured at 25 ° C. of less than 3 are preferably used as the acid. These are usually medium to strong acids. They are preferably selected from the group of organic sulfonic acids,
  • Phosphoric acids halogenated carboxylic acids, phosphonic acids, sulfuric acid, nitric acid, perchloric acid, hydrohalic acid, substituted with sulfonic acid polymer or mixtures thereof.
  • a sulfonic acid substituted polymer is Nafion, which is a sulfonated tetrafluoroethylene polymer.
  • the process according to the invention is preferably carried out as a reaction by means of homogeneous catalysis in the liquid phase.
  • reaction product is then obtained directly as
  • alpha, omega-dicarboxylic acid diesters This can optionally be further purified, for example by filtration and recrystallization.
  • the catalyst is added in amounts of 0.05 to 15 mol%, preferably 0.5 to 5 mol%, based on triglyceride. It is further preferred to set the ratio Palladium to P (III) groups in the catalyst in the range of 1: 2 to 1: 12 moles / mole.
  • the triglyceride is in relation to the OH group donor in the reaction in
  • the molar ratio of added acid to triglyceride is 0.1: 1 to 0.6: 1.
  • the inventive method is preferably carried out at a reaction temperature of 0 to 130 ° C, preferably from 60 to 90 ° C.
  • the CO partial pressure during the reaction is preferably 1 .000 to 60,000 hPa, preferably 10,000 to 30,000 hPa.
  • reaction process according to the invention thus provides a cost-effective alternative to the previous production processes of alpha, omega-dicarboxylic acid diesters in the prior art.
  • a five-fold excess of ligand is used for the anaerobic preforming of the catalyst.
  • the molar amount of the 1, 19-Nonadecandicarbonklare- dimethyl ester prepared in this way is equivalent to the consumed molar amount of carbon monoxide, which can be determined from the pressure drop of the CO partial pressure during the reaction.
  • the yield is over 85% based on the triglyceride.
  • Table 1 lists the yields based on the triglyceride and selectivities of experiments with different catalyst concentrations, solvent concentrations and different CO partial pressures.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Fats And Perfumes (AREA)

Abstract

L'invention concerne un procédé de préparation de diesters d'acides alpha, oméga-dicarboxyliques linéaires, selon lequel un triglycéride contenant des radicaux acides gras renfermant des chaînes carbone monoinsaturées ou polyinsaturées est mis en réaction avec du monoxyde de carbone, un acide et un donneur de groupes OH en présence d'un catalyseur, la réaction étant réalisée en une étape de réaction.
EP10782585A 2010-03-12 2010-11-19 Procédé de préparation de diesters d'acides alpha, oméga-dicarboxyliques linéaires Withdrawn EP2545026A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102010002809A DE102010002809A1 (de) 2010-03-12 2010-03-12 Verfahren zur Herstellung von linearen alpha,omega-Dicarbonsäurediestern
PCT/EP2010/067800 WO2011110249A1 (fr) 2010-03-12 2010-11-19 Procédé de préparation de diesters d'acides alpha, oméga-dicarboxyliques linéaires

Publications (1)

Publication Number Publication Date
EP2545026A1 true EP2545026A1 (fr) 2013-01-16

Family

ID=43431215

Family Applications (1)

Application Number Title Priority Date Filing Date
EP10782585A Withdrawn EP2545026A1 (fr) 2010-03-12 2010-11-19 Procédé de préparation de diesters d'acides alpha, oméga-dicarboxyliques linéaires

Country Status (8)

Country Link
US (1) US8604227B2 (fr)
EP (1) EP2545026A1 (fr)
JP (2) JP2013522248A (fr)
CN (1) CN102781902A (fr)
BR (1) BR112012023057A2 (fr)
DE (1) DE102010002809A1 (fr)
SG (1) SG183903A1 (fr)
WO (1) WO2011110249A1 (fr)

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EP2602328A1 (fr) 2011-12-05 2013-06-12 Evonik Industries AG Procédé d'oxydation d'alcanes en utilisant d'une alcane 1-mono-oxygénase AlkB
EP2607479A1 (fr) 2011-12-22 2013-06-26 Evonik Industries AG Production bio-technologique d'alcools et dérivés associés
EP2631298A1 (fr) 2012-02-22 2013-08-28 Evonik Industries AG Procédé biotechnologique et procédé de production de butanol et d'acide butyrique
EP2639308A1 (fr) 2012-03-12 2013-09-18 Evonik Industries AG Omega-oxydation et -amination enzymatique d'acides gras
EP2647696A1 (fr) 2012-04-02 2013-10-09 Evonik Degussa GmbH Procédé de fabrication aérobie d'alanine ou d'une liaison établie sous consommation d'alanine
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EP3922758A1 (fr) 2020-06-10 2021-12-15 Evonik Operations GmbH Procédé de fabrication électrochimique d'acides alcanicarboxyliques par oxydation avec ouverture de cycle au moyen d'une électrode en mousse ni(o)oh dopée
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EP4253602A1 (fr) 2022-03-28 2023-10-04 Evonik Operations GmbH Oxydation électrochimique des cycloalcènes et des cycloalcanes en acides alpha,oméga-dicarboniques ou en acides cétocarboniques et en composés de cycloalkanones

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Also Published As

Publication number Publication date
CN102781902A (zh) 2012-11-14
US20130006005A1 (en) 2013-01-03
JP2013522248A (ja) 2013-06-13
US8604227B2 (en) 2013-12-10
DE102010002809A1 (de) 2011-11-17
WO2011110249A1 (fr) 2011-09-15
SG183903A1 (en) 2012-10-30
BR112012023057A2 (pt) 2016-05-17
JP2015166371A (ja) 2015-09-24

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