WO2001056969A1 - Procede de production d'acide sorbique et d'ester d'acide sorbique ou de leurs derives - Google Patents

Procede de production d'acide sorbique et d'ester d'acide sorbique ou de leurs derives Download PDF

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Publication number
WO2001056969A1
WO2001056969A1 PCT/EP2001/000787 EP0100787W WO0156969A1 WO 2001056969 A1 WO2001056969 A1 WO 2001056969A1 EP 0100787 W EP0100787 W EP 0100787W WO 0156969 A1 WO0156969 A1 WO 0156969A1
Authority
WO
WIPO (PCT)
Prior art keywords
alkyl
sorbic acid
formula
transition metal
propyne
Prior art date
Application number
PCT/EP2001/000787
Other languages
German (de)
English (en)
Inventor
Peter Rudolf
Norbert Rieber
Thomas Barth
Original Assignee
Basf Aktiengesellschaft
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 Basf Aktiengesellschaft filed Critical Basf Aktiengesellschaft
Priority to AU2001237341A priority Critical patent/AU2001237341A1/en
Publication of WO2001056969A1 publication Critical patent/WO2001056969A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/353—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by isomerisation; by change of size of the carbon skeleton
    • 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
    • C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C67/347—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by addition to unsaturated carbon-to-carbon bonds

Definitions

  • the invention relates to a process for the preparation of sorbic acid and sorbic acid esters or their derivatives.
  • Sorbic acid is currently produced on an industrial scale by reacting crotonaldehyde and ketene (DE 1 042 573, DE 1 059 899).
  • crotonaldehyde and ketene DE 1 042 573, DE 1 059 899.
  • the manufacture and handling of ketene is complex and requires complicated process engineering.
  • DE-OS 25 54 403 discloses a process for the catalytic coupling of allyl compounds to substituted olefins, with which sorbic acid esters from allyl alcohol and acrylic acid esters or acrylate and propene (but only "in traces", see Example 5) are producible.
  • EP 55 936 discloses a process by which sorbic acid can be prepared from butadiene and acetic acid via an intermediate (acetoxyhexenoic acid).
  • the present invention had for its object to provide a process for the preparation of sorbic acid and its esters or their derivatives from easily accessible starting products, which does not have the disadvantages of the prior art and in high yields in relation to the acrylic compound converted, the end product delivers.
  • This object was achieved by a process in which propyne (methylacetylene) in the presence of a transition metal catalyst system containing ruthenium with a compound of the formula II
  • the process product is a compound of formula I.
  • R 1 and R 2 can have the meanings given above.
  • the alkyl or alkylene groups R 1 and R 2 can be straight-chain or branched.
  • the ruthenium-containing transition metal catalyst system preferably consists of the transition metal compound and a phosphine ligand and / or carbonyl ligand.
  • the transition metal catalyst system can consist of single and multi-core systems. Binuclear systems are preferably used as multinuclear complexes.
  • Suitable catalysts are, for example, ruthenium complexes with phosphine and / or carbonyl ligands in a range from 0.1 to 10.0 mol% (the mol percentages given relate in each case to the compound of the formula II used).
  • Alkyl here denotes branched or unbranched C 1 -C 6 -alkyl groups, preferably C 1 -C 4 -alkyl groups, with "cycloalkyl” C 3 -C 6 -cycloalkyl groups, which may be substituted by C 1 -C 3 -alkyl groups, phenyl groups optionally substituted with "aryl”.
  • the ligands occurring in the complexes are added to the reaction solution in the range from 0.4 to 40 mol%, particularly preferably 1 to 10 mol%. Mixtures of the ligands occurring in the complexes (0.4 to 40 mol%, particularly preferably 1 to 10 mol%) and further monodentate or bidentate phosphine ligands in the range from 0.1 to 10.0 mol% can also be used. %, very particularly preferably 1 to 10 mol%, are used.
  • ligands e.g.
  • multidentate ligands e.g. Bis (diphenylphosphino) methane, ethane or propane or 1,1,1-tris (diphenylphosphinomethyl) ethane used.
  • the process according to the invention is preferably carried out in an organic solvent.
  • Suitable solvents are ethers, hydrocarbons, nitriles, cyclic amides, lactones or alcohols. Tetrahydrofuran, dioxane, acetonitrile, pyridine, ethylene glycol diethyl ether, benzene, toluene, xylene,
  • acrylates used themselves, propyne in condensed form or mixtures thereof can be used as solvents.
  • the reaction can initially lead to a compound of the formula III
  • the process is preferably reacted at 20 to 200 ° C., particularly preferably at 40 to 120 ° C., and a pressure of 1 to 60 bar, preferably 1 to 20 bar, particularly preferably 1 to 5 bar.
  • the sorbic acid or the sorbic acid esters or their derivatives are obtained as a trans-trans and cis-trans isomer mixture.
  • the propyne can be used in a mixture with other hydrocarbons in the process according to the invention.
  • This mixture can e.g. the propyne-containing fraction of the cracking gas treatment of a steam cracker or a propyne-propadiene mixture (MAPD).
  • mixtures of this type can also be used because these mixtures represent a favorable starting product base and lead to the desired product without a further refinement step.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne un procédé de production de composés de la formule (I) comprenant R1 = H, alkyle C¿1?-C6, alcényle C1-C6, cycloalkyle C3-C6 ou phényle et R?2¿ = H ou alkyle C¿1?-C3. L'invention est caractérisée en ce que propyne est mis à réagir avec un composé de la formule (II), dans laquelle R?1 et R2¿ ont les significations susmentionnées, en présence d'un système de catalyseur à métal de transition contenant du ruthénium.
PCT/EP2001/000787 2000-02-04 2001-01-25 Procede de production d'acide sorbique et d'ester d'acide sorbique ou de leurs derives WO2001056969A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2001237341A AU2001237341A1 (en) 2000-02-04 2001-01-25 Method for producing sorbic acid and sorbic acid esters or derivatives thereof

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE2000104911 DE10004911A1 (de) 2000-02-04 2000-02-04 Verfahren zur Herstellung von Sorbinsäure und Sorbinsäureestern oder deren Derivaten
DE10004911.7 2000-02-04

Publications (1)

Publication Number Publication Date
WO2001056969A1 true WO2001056969A1 (fr) 2001-08-09

Family

ID=7629806

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2001/000787 WO2001056969A1 (fr) 2000-02-04 2001-01-25 Procede de production d'acide sorbique et d'ester d'acide sorbique ou de leurs derives

Country Status (3)

Country Link
AU (1) AU2001237341A1 (fr)
DE (1) DE10004911A1 (fr)
WO (1) WO2001056969A1 (fr)

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0737663A1 (fr) * 1995-04-12 1996-10-16 BASF Aktiengesellschaft Procédé pour la préparation de composés acétyléniquement insaturés
DE19835783A1 (de) * 1998-08-07 2000-02-17 Basf Ag Verfahren zur Herstellung von Sorbinsäure und Sorbinsäureestern oder deren Derivaten

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0737663A1 (fr) * 1995-04-12 1996-10-16 BASF Aktiengesellschaft Procédé pour la préparation de composés acétyléniquement insaturés
DE19835783A1 (de) * 1998-08-07 2000-02-17 Basf Ag Verfahren zur Herstellung von Sorbinsäure und Sorbinsäureestern oder deren Derivaten

Also Published As

Publication number Publication date
DE10004911A1 (de) 2001-08-09
AU2001237341A1 (en) 2001-08-14

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