EP0152801B1 - Process for manufacturing benzaldehyde dialkylacetals - Google Patents

Process for manufacturing benzaldehyde dialkylacetals 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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Prior art keywords
electrolyte
benzyl
benzaldehyde
acid
electrolysis
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German (de)
French (fr)
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EP0152801A3 (en
EP0152801A2 (en
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Dieter Dr. Degner
Eckhard Roske
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BASF SE
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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

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)

Description

Diese Erfindung betrifft ein neues Verfahren zur Herstellung von Benzaldehyddialkylacetalen durch Elektrooxidation von Benzylalkylethern.This invention relates to a new process for the preparation of benzaldehyde dialkyl acetals by electrooxidation of benzyl alkyl ethers.

Die elektrochemische Oxidation von Toluolderivaten in Gegenwart eines Alkanols zu den entsprechenden Benzaldehyddialkylacetalen ist z. B. aus J. Chem. Soc. Perkin 1 (1978) 708 bis 715, DE-PS-28 48 397 oder EP-PS-12 240 bekannt. Bei diesen Verfahren werden die Benzaldehyddialkylacetale nur dann in guter Selektivität erhalten, wenn das eingesetzte Toluolderivat in 4-Stellung einen Substituenten mit Elektronendonatoreigenschaften aufweist. Das unsubstituierte Toluol läßt sich unter den Bedingungen der Elektrooxidation nur in sehr schlechten Selektivitäten in die Dialkylacetale des Benzaldehyds überführen (s. FR-PS-2 351 932).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. In these processes, 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).

Es wurde nun gefunden, daß man Benzaldehyddialkylacetale der allgemeinen Formel

Figure imgb0001
in der R eine Methyl- oder Ethylgruppe bedeutet, mit sehr guter Selektivität erhält, wenn man Benzylalkylether der allgemeinen Formel
Figure imgb0002
in Abwesenheit von Toluol und in Gegenwart eines Alkohols der Formel ROH und eines Grundelektrolyten elektrochemisch oxidiert.It has now been found that benzaldehyde dialkyl acetals of the general formula
Figure imgb0001
 in which R represents a methyl or ethyl group, with very good selectivity, if benzyl alkyl ethers of the general formula
Figure imgb0002
 electrochemically oxidized in the absence of toluene and in the presence of an alcohol of the formula ROH and a base electrolyte.

Das erfindungsgemäße Verfahren läßt sich in an sich üblichen Elektrolysezellen durchführen. Besonders gut eignet sich eine ungeteilte Durchflußzelle mit bipolarer Elektrodenanordnung. Als Anodenmaterialien kommen Edelmetalle, wie Pt oder Metalloxide, wie Pb02 oder Ru02 in Betracht. Bevorzugtes Anodenmaterial ist Graphit.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.

Als Kathodenmaterialien lassen sich z. B. Edelmetalle, wie Platin, andere Metalle, wie Nickel oder Eisen bzw. Metallegierungen, wie Stahl einsetzen. Auch Graphit ist als Kathodenmaterial geeignet. Als Grundelektrolyt kommen Basen, Neutralsalze und Säuren in Frage. Basen sind z. B. Alkalihydroxide, wie NaOH oder KOH sowie Alkalialkoholate wie NaOCH3. Als Neutralsalze werden Fluoride, wie KF, Sulfonate, wie KSO3C6H5 oder Alkylsulfate wie (CH3)4N+ SO4CH3- eingesetzt. Als Säuren dienen beispielsweise Schwefelsäuren oder Sulfonsäuren, wie CH3SO3H oder C6H5SO3H. Bei dem erfindungsgemäßen Verfahren werden als Ausgangsgemische für die elektrochemische Oxidation Elektrolyte eingesetzt, die sich aus dem Benzylalkylether, dem Alkohol und dem Grundelektrolyten zusammensetzen. Bevorzugt werden saure oder neutrale Elektrolyte eingesetzt. Die Elektrolytzusammensetzung kann in weiten Grenzen variiert werden. Vorzugsweise wird ein Elektrolyt verwendet, der einen Gehalt an dem Benzylalkylether von 10 bis 50 Gew. % und an dem Alkohol von 50 bis 90 Gew. % aufweist, wobei der Elektrolyt außerdem noch 0,1 bis 5 Gew. %, bezogen auf das Gemisch aus Benzylalkylether und Alkohol, einer Säure oder eines Neutralsalzes enthält.As 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. Examples of acids used are sulfuric acids or sulfonic acids, such as CH 3 SO 3 H or C 6 H 5 SO 3 H. In the process according to the invention, 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.

Die elektrochemische Oxidation wird bei Stromdichten von z. B. 0,5 bis 20 A/dm2, bevorzugt bei 2 bis 10 A/dm2 durchgeführt. Die Temperaturen während der Elektrolyse können ebenfalls in weiten Grenzen gewählt werden. Vorzugsweise elektrolysiert man bei Temperaturen bis zu 5 °C unterhalb des Siedepunktes des Alkanols. Ein großer Vorteil des Verfahrens ist es, daß die Benzylalkylether zu über 50 % umgesetzt werden können, ohne daß die Selektivität der Elektrooxidation absinkt. Weiterhin können die Alkanole, die zugleich als Lösungsmittel dienen, ohne jegliche Zwischenreinigung zur Elektrolyse rückgeführt werden, ohne daß es, wie häufig bei technischen organischen Elektrolysen beobachtet, durch Belagsbildung auf den Elektroden zu einer Beeinträchtigung der Elektrolyse kommt. Das Verfahren ist somit auch kontinuierlich auf einfache Weise durchführbar.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. Furthermore, 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.

Die nach dem Verfahren erhaltenen Benzaldehydalkylacetale sind wertvolle Riechstoffe.The benzaldehyde alkyl acetals obtained by the process are valuable fragrances.

Das erfindungsgemäße Verfahren wird an folgenden Beispielen weiter verdeutlicht.The process according to the invention is further illustrated in the following examples.

Beispiel 1example 1

Elektrosynthese von Benzaldehyddimethylacetal (neutraler Elektrolyt)

  • Apparatur : ungeteilte Durchflußzelle mit 6 Elektroden
  • Anode : Graphit
  • Kathode : Nickel
  • Elektrolyt :
    • 258 g Benzylmethylether
    • 25 g KF
    • 2 370 g Methanol
  • Stromdichte : 3,3 A/dm2
  • Temperatur: 22 bis 30 °C
  • Elektrolyse mit 6 F/Mol Benzylmethylether
Electrosynthesis of benzaldehyde dimethyl acetal (neutral electrolyte)
  • Apparatus: undivided flow cell with 6 electrodes
  • Anode: graphite
  • Cathode: nickel
  • Electrolyte:
    • 258 g of benzyl methyl ether
    • 25 g KF
    • 2,370 g of methanol
  • Current density: 3.3 A / dm 2
  • Temperature: 22 to 30 ° C
  • Electrolysis with 6 F / mol benzyl methyl ether

Der Elektrolyt wird während der Elektrolyse mit 200 I/h durch die Zelle gepumpt.The electrolyte is pumped through the cell at 200 l / h during the electrolysis.

Aufarbeitung : Zunächst wird Methanol bei Normaldruck und 60 bis 70 °C abdestilliert, dann das ausgefallene Leitsalz KF über eine Drucknutsche abgetrennt und das erhaltene Filtrat bei 80 bis 120 °C und 10 bis 30 Torr (13 bis 40 mbar) reindestilliert. Hierbei erhält man neben 56,6 g Benzylmethylether (kann mit CH30H/KF zur Elektrolyse rückgeführt werden) 207,2 g Benzaldehyddimethylacetal. Hieraus ergibt sich ein Umsatz an Benzylmethylether von 78,1 %, eine Ausbeute an Benzaldehyddimethylacetal von 64,4 % und eine Selektivität für Benzaldehyddimethylacetal von 82,6 %.Working up: First, methanol is distilled off at normal pressure and 60 to 70 ° C, then the precipitated conductive salt KF is separated off using a pressure filter and the filtrate obtained is distilled at 80 to 120 ° C and 10 to 30 torr (13 to 40 mbar). In addition to 56.6 g of benzyl methyl ether (can be recycled to CH 3 0H / KF for electrolysis), 207.2 g of benzaldehyde dimethyl acetal are obtained. This results in a conversion of benzyl methyl ether of 78.1%, a yield of benzaldehyde dimethyl acetal of 64.4% and a selectivity for benzaldehyde dimethyl acetal of 82.6%.

Beispiel 2Example 2

Elektrosynthese von Benzaldehyddimethylacetal (saurer Elektrolyt)

  • Apparatur: ungeteilte Durchflußzelle mit 6 Elektroden
  • Anode : Graphit
  • Kathode : Graphit
  • Elektrolyt :
    • 457 g Benzylmethylether
    • 14,4 g Schwefelsäure
    • 3107 g Methanol
  • Stromdichte : 3,3 A/dm2
  • Temperatur: 20 bis 30 °C
  • Elektrolyse mit 4,5 F/Mol Benzylmethylether.
Electrosynthesis of benzaldehyde dimethyl acetal (acid electrolyte)
  • Apparatus: undivided flow cell with 6 electrodes
  • Anode: graphite
  • Cathode: graphite
  • Electrolyte:
    • 457 g of benzyl methyl ether
    • 14.4 g sulfuric acid
    • 3107 g of methanol
  • Current density: 3.3 A / dm 2
  • Temperature: 20 to 30 ° C
  • Electrolysis with 4.5 F / mol benzyl methyl ether.

Der Elektrolyt wird während der Elektrolyse mit 200 I/h durch die Zelle gepumpt.The electrolyte is pumped through the cell at 200 l / h during the electrolysis.

Aufarbeitung : Der Elektrolyseaustrag wird mit NaOCH3 neutralisiert und dann analog Beispiel 1 aufgearbeitet. Hierbei erhält man 21,2 g Benzylmethylether und 355,7 g Benzaldehyddimethylacetal. Hieraus ergibt sich ein Umsatz an Benzylmethylether von 95,4 %, eine Ausbeute an Benzaldehyddialkylacetal von 62,5 % und eine Selektivität für Benzaldehyddialkylacetal von 65,5 %.Workup: The electrolysis discharge is neutralized with NaOCH 3 and then worked up analogously to Example 1. This gives 21.2 g of benzyl methyl ether and 355.7 g of benzaldehyde dimethyl acetal. This results in a conversion of benzyl methyl ether of 95.4%, a yield of benzaldehyde dialkyl acetal of 62.5% and a selectivity for benzaldehyde dialkyl acetal of 65.5%.

Beispiel 3Example 3

Elektrosynthese von Benzaldehyddimethylacetal (basischer Elektrolyt)

  • Apparatur: ungeteilte Durchflußzelle mit 6 Elektroden
  • Anode : Graphit
  • Kathode : Graphit
  • Elektrolyt :
    • 360 g Benzylmethylether
    • 36 g NaOH
    • 3 204 g Methanol
  • Stromdichte : 3,3 A/dm2
  • Temperatur: 20 bis 30 °C
  • Elektrolyse mit 7 F/Mol Benzylmethylether
Electrosynthesis of benzaldehyde dimethyl acetal (basic electrolyte)
  • Apparatus: undivided flow cell with 6 electrodes
  • Anode: graphite
  • Cathode: graphite
  • Electrolyte:
    • 360 g of benzyl methyl ether
    • 36 g NaOH
    • 3 204 g of methanol
  • Current density: 3.3 A / dm 2
  • Temperature: 20 to 30 ° C
  • Electrolysis with 7 F / mol benzyl methyl ether

Der Elektrolyt wird während der Elektrolyse mit 200 I/h durch die Zelle gepumpt.The electrolyte is pumped through the cell at 200 l / h during the electrolysis.

Aufarbeitung : Der Elektrolyseaustrag wird analog Beispiel 1 aufgearbeitet. Man erhält 115,1 g Benzylmethylether und 138,7 g Benzaldehyddimethylacetal. Hieraus ergibt sich ein Umsatz an Benzylmethylether von 68,0 %, eine Ausbeute an Benzyladehyddimethylacetal von 30,9 % und eine Selektivität für Benzaldehyddimethylacetal von 45,5 %.Working up: The electrolysis discharge is worked up analogously to Example 1. 115.1 g of benzyl methyl ether and 138.7 g of benzaldehyde dimethyl acetal are obtained. This results in a conversion of benzyl methyl ether of 68.0%, a yield of benzyladehyddimethylacetal of 30.9% and a selectivity for benzaldehyde dimethyl acetal of 45.5%.

Beispiel 4Example 4

Elektrosynthese von Benzaldehyddiethylacetal

  • Apparatur : ungeteilte Durchflußzelle mit 6 Elektroden
  • Anode : Graphit
  • Kathode : Graphit
  • Elektrolyt :
    • 345 g Benzylethylether
    • 18 g Schwefelsäure
    • 3 237 g Ethanol
  • Stromdichte : 3,3 A/dm2
  • Temperatur : 25 bis 35 °C
  • Elektrolyse mit 4,2 F/Mol Benzylethylether
Electrosynthesis of benzaldehyde diethylacetal
  • Apparatus: undivided flow cell with 6 electrodes
  • Anode: graphite
  • Cathode: graphite
  • Electrolyte:
    • 345 g benzyl ethyl ether
    • 18 g sulfuric acid
    • 3,237 g of ethanol
  • Current density: 3.3 A / dm 2
  • Temperature: 25 to 35 ° C
  • Electrolysis with 4.2 F / mol benzyl ethyl ether

Der Elektrolyt wird während der Elektrolyse mit 200 I/h durch die Zelle gepumpt.The electrolyte is pumped through the cell at 200 l / h during the electrolysis.

Aufarbeitung : Der Elektrolyseaustrag wird zunächst mit NaOH neutralisiert. Dann wird Ethanol bei Normaldruck und 75 bis 90 °C abdestilliert. Das ausgefallene Salz wird über eine Drucknutsche abgetrennt und das Filtrat bei 80 bis 100 °C und 10 bis 20 Torr (13 bis 26 mbar) fraktioniert. Hierbei erhält man 123,6 g Benzylethylether und 262,5 g Benzaldehyddiethylacetal. Hieraus ergibt sich ein Umsatz an Benzylethylether von 64,2 %, eine Ausbeute an Benzaldehyddiethylacetal von 57,5 % und eine Selektivität für Benzaldehyddiethylacetal von 89,6 %.Processing: 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%.

Claims (8)

1. A process for the preparation of a benzaldehyde dialkylacetal of the general formula
Figure imgb0005
where R is methyl or ethyl, wherein a benzyl alkylether of the general formula
Figure imgb0006
is oxidized electrochemically in the absence of toluene and in the presence of an alcohol of the formula ROH and of a base electrolyte.
2. A process as claimed in claim 1, wherein the electrochemical oxidation is carried out in a non- partitioned through-circulation cell at graphite anodes.
3. A process as claimed in claim 1, wherein a neutral salt is used as the base electrolyte.
4. A process as claimed in claim 1, wherein potassium fluoride or potassium benzosulphonate is used as the base electrolyte.
5. A process as claimed in claim 1, wherein an acid is used as the base electrolyte.
6. A process as claimed in claim 1, wherein sulphuric acid, methylsulphuric acid or benzenesulphonic acid is used as the base electrolyte.
7. A process as claimed in claim 1, wherein an electrolyte, containing from 10 to 50 % by weight of benzyl alkylether and from 90 to 50 % by weight of alkanol, and additionally containing from 0.1 to 5 % by weight, based on the mixture of benzyl alkylether and alkanol, of an acid or a neutral salt, is used as the starting mixture for the electrochemical oxidation.
8. A process as claimed in claim 1, wherein the electrochemical oxidation is carried out at a current density of from 0.5 to 20 A/dm2 and at a temperature of up to 5 °C below the boiling point of the alkanol.
EP85100746A 1984-02-03 1985-01-25 Process for manufacturing benzaldehyde dialkylacetals Expired EP0152801B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3403789 1984-02-03
DE19843403789 DE3403789A1 (en) 1984-02-03 1984-02-03 METHOD FOR PRODUCING BENZALDEHYDDIALKYL ACETALES

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

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3708337A1 (en) * 1987-03-14 1988-09-22 Basf Ag METHOD FOR PRODUCING METHOXIACETALDEHYDDIALKYLACETALS
DE3913166A1 (en) * 1989-04-21 1990-10-25 Basf Ag METHOD FOR PRODUCING BENZALDEHYDDIALKYLACETALS AND NEW BENZALDEHYDDIALKYLACETALS AND BENZYL ESTERS
DE4201544A1 (en) * 1992-01-22 1993-07-29 Basf Ag METHOD FOR THE PRODUCTION OF BENZALDEHYDACETALES

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DE2848397C2 (en) * 1978-11-08 1982-09-23 Basf Ag, 6700 Ludwigshafen Electrochemical production of benzaldehyde dialkyl acetals substituted in the 4-position

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DE3560200D1 (en) 1987-07-02
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DE3403789A1 (en) 1985-08-08

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