EP0152801B1 - Procédé de production de dialkylacétals de benzaldéhyde - Google Patents

Procédé de production de dialkylacétals de benzaldéhyde Download PDF

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Publication number
EP0152801B1
EP0152801B1 EP85100746A EP85100746A EP0152801B1 EP 0152801 B1 EP0152801 B1 EP 0152801B1 EP 85100746 A EP85100746 A EP 85100746A EP 85100746 A EP85100746 A EP 85100746A EP 0152801 B1 EP0152801 B1 EP 0152801B1
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EP
European Patent Office
Prior art keywords
electrolyte
benzyl
benzaldehyde
acid
electrolysis
Prior art date
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Expired
Application number
EP85100746A
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German (de)
English (en)
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EP0152801A2 (fr
EP0152801A3 (en
Inventor
Dieter Dr. Degner
Eckhard Roske
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BASF SE
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BASF SE
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Publication date
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Publication of EP0152801A2 publication Critical patent/EP0152801A2/fr
Publication of EP0152801A3 publication Critical patent/EP0152801A3/de
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    • C—CHEMISTRY; METALLURGY
    • C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
    • C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
    • C25B3/00—Electrolytic production of organic compounds
    • C25B3/20—Processes
    • C25B3/23—Oxidation
    • C—CHEMISTRY; METALLURGY
    • C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
    • C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
    • C25B3/00—Electrolytic production of organic compounds
    • C25B3/01—Products
    • C25B3/07—Oxygen containing compounds

Definitions

  • This invention relates to a new process for the preparation of benzaldehyde dialkyl acetals by electrooxidation of benzyl alkyl ethers.
  • the electrochemical oxidation of toluene derivatives in the presence of an alkanol to the corresponding benzaldehyde dialkyl acetals is e.g. B. from J. Chem. Soc. Perkin 1 (1978) 708 to 715, DE-PS-28 48 397 or EP-PS-12 240.
  • the benzaldehyde dialkyl acetals are only obtained with good selectivity if the toluene derivative used has a substituent with electron donor properties in the 4-position.
  • the unsubstituted toluene can only be converted into the dialkylacetals of benzaldehyde in very poor selectivities under the conditions of electrooxidation (see FR-PS-2 351 932).
  • the process according to the invention can be carried out in electrolysis cells which are conventional per se.
  • An undivided flow cell with a bipolar electrode arrangement is particularly suitable.
  • Precious metals such as Pt or metal oxides such as Pb0 2 or Ru0 2 are suitable as anode materials.
  • the preferred anode material is graphite.
  • cathode materials such.
  • B. use precious metals such as platinum, other metals such as nickel or iron or metal alloys such as steel.
  • Graphite is also suitable as the cathode material.
  • Bases, neutral salts and acids can be used as the basic electrolyte.
  • Bases are e.g. B. alkali metal hydroxides such as NaOH or KOH and alkali metal alcoholates such as NaOCH 3rd Fluorides such as KF, sulfonates such as KSO 3 C 6 H 5 or alkyl sulfates such as (CH 3 ) 4 N + SO 4 CH 3 - are used as neutral salts.
  • electrolytes are used as starting mixtures for the electrochemical oxidation, which are composed of the benzyl alkyl ether, the alcohol and the basic electrolyte. Acidic or neutral electrolytes are preferably used.
  • the electrolyte composition can be varied within wide limits.
  • An electrolyte is preferably used which has a content of 10 to 50% by weight of the benzyl alkyl ether and 50 to 90% by weight of the alcohol, the electrolyte also containing 0.1 to 5% by weight, based on the mixture from benzyl alkyl ether and alcohol, an acid or a neutral salt.
  • the electrochemical oxidation is carried out at current densities of e.g. B. 0.5 to 20 A / dm 2 , preferably carried out at 2 to 10 A / dm 2 .
  • the temperatures during the electrolysis can also be selected within wide limits.
  • Electrolysis is preferably carried out at temperatures up to 5 ° C. below the boiling point of the alkanol.
  • a great advantage of the process is that more than 50% of the benzylalkyl ethers can be converted without reducing the selectivity of the electrooxidation.
  • the alkanols, which also serve as solvents can be returned to the electrolysis without any intermediate cleaning, without the electrolysis being adversely affected by the formation of deposits on the electrodes, as is frequently observed in industrial organic electrolysis.
  • the method can thus also be carried out continuously in a simple manner.
  • the benzaldehyde alkyl acetals obtained by the process are valuable fragrances.
  • the electrolyte is pumped through the cell at 200 l / h during the electrolysis.
  • the electrolyte is pumped through the cell at 200 l / h during the electrolysis.
  • the electrolyte is pumped through the cell at 200 l / h during the electrolysis.
  • the electrolyte is pumped through the cell at 200 l / h during the electrolysis.
  • the electrolysis discharge is first neutralized with NaOH. Then ethanol is distilled off at normal pressure and 75 to 90 ° C. The precipitated salt is separated off using a pressure filter and the filtrate is fractionated at 80 to 100 ° C. and 10 to 20 torr (13 to 26 mbar). This gives 123.6 g of benzyl ethyl ether and 262.5 g of benzaldehyde diethylacetal. This results in a conversion of benzyl ethyl ether of 64.2%, a yield of benzaldehyde diethylacetal of 57.5% and a selectivity for benzaldehyde diethylacetal of 89.6%.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Electrochemistry (AREA)
  • Materials Engineering (AREA)
  • Metallurgy (AREA)
  • Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)

Claims (8)

1. Procédé de préparation de benzaldéhyde-diakylacétals de formule générale
Figure imgb0007
dans laquelle R représente un groupement méthyle ou éthyle, caractérisé en ce qu'on oxyde électrochimiquement des benzylalkyléthers de formule générale
Figure imgb0008
en l'absence de toluène et en présence d'un alcool de formule ROH et d'un électrolyte de base.
2. Procédé selon la revendication 1, caractérisé en ce qu'on effectue l'oxydation électrochimique sur des anodes de graphite dans une cuve à circulation non cloisonnée.
3. Procédé selon la revendication 1, caractérisé en ce qu'on utilise un sel neutre comme électrolyte de base.
4. Procédé selon la revendication 1, caractérisé en ce qu'on utilise, comme électrolyte de base, le fluorure de potassium ou le benzénesulfonate de potassium.
5. Procédé selon la revendication 1, caractérisé en ce qu'on utilise des acides comme électrolyte de base.
6. Procédé selon la revendication 1, caractérisé en ce qu'on utilise, comme électrolyte de base, l'acide sulfurique, l'acide méthanesulfonique ou l'acide benzènesulfonique.
7. Procédé selon la revendication 1, caractérisé en ce qu'on utilise, comme mélange de départ pour l'oxydation électrochimique, un électrolyte qui présente une teneur en benzylalkyléther de 10 à 50 % en poids et une teneur en alcanol de 90 à 50 % en poids et qui contient en plus, sur la base du mélange de benzylalkyléther et d'alcanol, 0,1 à 5 % en poids d'un acide ou d'un sel neutre.
8. Procédé selon la revendication 1, caractérisé en ce qu'on effectue l'oxydation électrochimique à des densités de courant de 0,5 à 20 A/dm2 et à des températures pouvant aller jusqu'à 5 °C au-dessous de la température d'ébullition de l'alcanol.
EP85100746A 1984-02-03 1985-01-25 Procédé de production de dialkylacétals de benzaldéhyde Expired EP0152801B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3403789 1984-02-03
DE19843403789 DE3403789A1 (de) 1984-02-03 1984-02-03 Verfahren zur herstellung von benzaldehyddialkylacetalen

Publications (3)

Publication Number Publication Date
EP0152801A2 EP0152801A2 (fr) 1985-08-28
EP0152801A3 EP0152801A3 (en) 1985-09-25
EP0152801B1 true EP0152801B1 (fr) 1987-05-27

Family

ID=6226702

Family Applications (1)

Application Number Title Priority Date Filing Date
EP85100746A Expired EP0152801B1 (fr) 1984-02-03 1985-01-25 Procédé de production de dialkylacétals de benzaldéhyde

Country Status (2)

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EP (1) EP0152801B1 (fr)
DE (2) DE3403789A1 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3708337A1 (de) * 1987-03-14 1988-09-22 Basf Ag Verfahren zur herstellung von methoxiacetaldehyddialkylacetalen
DE3913166A1 (de) * 1989-04-21 1990-10-25 Basf Ag Verfahren zur herstellung von benzaldehyddialkylacetalen und neue benzaldehyddialkylacetale und benzylester
DE4201544A1 (de) * 1992-01-22 1993-07-29 Basf Ag Verfahren zur herstellung von benzaldehydacetalen

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2848397C2 (de) * 1978-11-08 1982-09-23 Basf Ag, 6700 Ludwigshafen Elektrochemische Herstellung von in 4-Stellung substituierten Benzaldehyddialkylacetalen

Also Published As

Publication number Publication date
DE3560200D1 (en) 1987-07-02
DE3403789A1 (de) 1985-08-08
EP0152801A2 (fr) 1985-08-28
EP0152801A3 (en) 1985-09-25

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