EP0030588A1 - Process for the preparation of p-tert.-butylbenzaldehyde - Google Patents
Process for the preparation of p-tert.-butylbenzaldehyde Download PDFInfo
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- EP0030588A1 EP0030588A1 EP80105721A EP80105721A EP0030588A1 EP 0030588 A1 EP0030588 A1 EP 0030588A1 EP 80105721 A EP80105721 A EP 80105721A EP 80105721 A EP80105721 A EP 80105721A EP 0030588 A1 EP0030588 A1 EP 0030588A1
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- tert
- anode
- butylbenzaldehyde
- butyltoluene
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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
- the present invention relates to a process for producing an aldehyde, namely p-tert. Butylbenzaldehyde.
- butylbenzaldehyde has been obtained by oxidation of p-tert. Butyltoluene with chemical oxidizing agents, especially with manganese dioxide. This procedure has serious disadvantages, in particular with regard to the manganese salts that occur in large quantities. Furthermore, the manganese dioxide used here is not supplied in the same quality, but rather in very different quality, which of course does not allow a uniform procedure.
- Butylbenzaldehyde consists in that p-tert. Butyltoluene electrochemically oxidized. Such anodic oxidation avoids using Disadvantages associated with manganese dioxide as a chemical oxidizing agent and allows p-tert. Obtaining butylbenzaldehyde in a simple manner and in high yields, and moreover as a usable by-product on the! Cathode still produces hydrogen.
- Metal anode anodes for example lead dioxide or manganese dioxide anodes, are expediently used as anodes in the electrochemical process according to the invention.
- a particularly preferred embodiment of the method according to the invention consists in using a metal oxide-titanium composite anode.
- Such composite anodes consist of a carrier made of titanium, which is provided with a metal oxide coating, an intermediate layer of a carbide or boride of the elements of the IV. And V. subgroup being applied to the titanium surface before the metal oxide coating is applied.
- Such a composite anode namely a lead dioxide-titanium composite anode, and its production is described in German Patent 2,344,645.
- An improved method for producing such an anode is described in German Offenlegungsschrift No. 2,722,840. According to the invention, such a lead dioxide-titanium composite anode is preferably used.
- manganese dioxide is used as the anode material, this can be applied either to graphite or to lead or to lead dioxide.
- graphite anodes can advantageously be used in the case of the invention.
- anode materials that can be used are precious metals, e.g. Platinum or platinum-plated titanium.
- Athodenmaterialien K used in the inventive process are not critical. Steel, nickel and copper, for example, are suitable as cathode materials.
- the electrodes both the anode and the cathode, can have customary shapes.
- the electrodes can be designed in the form of plates or grids or as expanded metal.
- the electrolysis can be carried out in undivided or in divided cells, in which case the latter can be divided with membranes or diaphragms made of conventional membrane or diaphragm materials.
- the voltages and currents used depend on the solvent used, the size of the cell and the current density used. In general, a voltage of between approximately 3 and approximately 20 V is used.
- the current density can vary within wide limits, the current densities generally between approximately 0.01 and approximately 100 mA per cm, in particular between approximately 0.4 and approximately 50 mA can be per cm 2 .
- the electrolysis according to the invention can be carried out directly in a mixture of an electrolyte and the p-tert used as the starting material. Butyltoluene are carried out using no other solvent.
- aqueous acids in particular non-oxidative mineral acids, can be used as electrolytes.
- Sulfuric acid has proven to be particularly suitable. It is expedient to work with a 5-50%, especially with a 7.5-15% aqueous sulfuric acid.
- a mixture which consists of the above-mentioned aqueous acid and an inert organic solvent, for example a hydrocarbon such as hexane, a chlorinated hydrocarbon such as dichloroethane or methylene chloride, a tertiary lower alkanol, for example tert. Butanol, or acetone.
- an inert organic solvent for example a hydrocarbon such as hexane, a chlorinated hydrocarbon such as dichloroethane or methylene chloride, a tertiary lower alkanol, for example tert. Butanol, or acetone.
- the proportion of the organic solvent in the mixture is expediently from about 10 to about 60%.
- phase transfer catalyst for example a tetraalkylammonium salt such as tetrabutylammonium hydrogen sulfate.
- a phase transfer catalyst is the dodecyl hydrogen sulfate sodium salt.
- metal oxide anodes in particular metal oxide composite anodes
- dichloroethane as the solvent
- graphite anodes acetone has proven to be particularly advantageous as solvent.
- Butylbenzaldehyde in particular when graphite anodes are used, in addition to the desired p-tert. Butylbenzaldehyde in smaller amounts the corresponding alcohol. This can be separated by distillation and returned to the process, i.e. the starting material, p-tert. Butyltoluene, can be added.
- the concentration of the starting material in the electrolyte mixture used can generally vary between about 1 and 80%, in particular between about 10 and 50%, preferably between about 10 and 20%.
- the temperature used in carrying out the method according to the invention is not critical. However, there is an upper limit on the boiling point of the solvent. Generally one works between room temperature and about 80 ° C, in particular between room temperature and about 60 C.
- Metal salts for example manganese-II salts, such as manganese-II sulfate, or cerium III salts, such as cerium-III sulfate, can be added to the electrolyte in a manner known per se, and only in small amounts, for example in an amount of about 1% based on the amount of the batch.
- an undivided electrolysis cell provided with a graphite foil with a surface area of 25 cm 2 as the anode and a nickel wire as the cathode, a solution of 2.5 ml of p-tert. Butyltoluene in 40 ml of 3N aqueous sulfuric acid and 80 ml of acetone at room temperature, 0.75 A current and 7.8-8.5 V voltage electrolyzed with stirring. After the electrolysis has ended (after 2 hours), a sample is taken and extracted with chloroform. The products are determined by gas chromatography. With a conversion of 79%, the yield of p-tert. Butylbenzaldehyde (based on converted p-tert. Butyltoluene) 60 mol%, the yield of p-tert. Butylbenzyl alcohol 10 mol%.
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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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Die vorliegende Erfindung betrifft ein Verfahren zur Herstellung eines Aldehyds, nämlich von p-tert. Butylbenzaldehyd.The present invention relates to a process for producing an aldehyde, namely p-tert. Butylbenzaldehyde.
Der p-tert. Butylbenzaldehyd wurde bisher durch Oxydation von p-tert. Butyltoluol mit chemischen Oxydationsmitteln, insbesondere mit Mangandioxyd, hergestellt. Diese Verfahrensweise hat schwerwiegende Nachteile, insbesondere im Hinblick auf die hierbei in grossen Mengen anfallenden Mangansalze. Weiterhin wird das hierbei verwendete Mangandioxyd nicht in gleichbleibender, sondern vielmehr in sehr unterschiedlicher Qualität geliefert, was naturgemäss eine einheitliche Verfahrensführung nicht ermöglicht.The p-tert. So far, butylbenzaldehyde has been obtained by oxidation of p-tert. Butyltoluene with chemical oxidizing agents, especially with manganese dioxide. This procedure has serious disadvantages, in particular with regard to the manganese salts that occur in large quantities. Furthermore, the manganese dioxide used here is not supplied in the same quality, but rather in very different quality, which of course does not allow a uniform procedure.
Es wurde nun ein Verfahren gefunden, welches nicht mit diesen Nachteilen und Schwierigkeiten verbunden ist und welches es dennoch ermöglicht, das gewünschte Produkt in hoher Ausbeute zu erhalten.A process has now been found which is not associated with these disadvantages and difficulties and which nevertheless makes it possible to obtain the desired product in high yield.
Das erfindungsgemässe Verfahren zur Herstellung von p-tert. Butylbenzaldehyd besteht darin, dass man p-tert. Butyltoluol elektrochemisch oxydiert. Eine derartige anodische Oxydation vermeidet die mit der Verwendung von Mangandioxyd als chemisches Oxydationsmittel verbundenen Nachteile und gestattet es, p-tert. Butylbenzaldehyd auf einfache Weise und mit hohen Ausbeuten zu erhalten, wobei ausserdem als gut verwertbares Nebenprodukt an der ! Kathode noch Wasserstoff anfällt.The inventive method for the production of p-tert. Butylbenzaldehyde consists in that p-tert. Butyltoluene electrochemically oxidized. Such anodic oxidation avoids using Disadvantages associated with manganese dioxide as a chemical oxidizing agent and allows p-tert. Obtaining butylbenzaldehyde in a simple manner and in high yields, and moreover as a usable by-product on the! Cathode still produces hydrogen.
Als Anoden werden beim erfindungsgemässen elektrochemischen Verfahren zweckmässig Metalloxydanoden, beispielsweise Bleidioxyd- oder Mangandioxyd-Anoden verwendet.Metal anode anodes, for example lead dioxide or manganese dioxide anodes, are expediently used as anodes in the electrochemical process according to the invention.
Eine besonders bevorzugte Ausführungsform des erfindungsgemässen Verfahrens besteht darin, dass man eine Metalloxyd-Titan-Verbundanode verwendet. Solche Verbundanoden bestehen aus einem Träger aus Titan, welcher mit einer Metalloxydauflage versehen ist, wobei auf der Titanoberfläche vor der Aufbringung des Metalloxydüberzuges eine Zwischenschicht aus einem Carbid oder Borid der Elemente der IV. und V. Nebengruppe aufgebracht wird. Eine derartige Verbundanode, nämlich eine Bleidioxyd-Titan-Verbundanode, sowie deren Herstellung ist in der deutschen Patentschrift 2 344 645 beschrieben. Ein verbessertes Verfahren zur Herstellung einer derartigen Anode ist in der deutschen Offenlegungsschrift 2 722 840 beschrieben. Erfindungsgemäss wird bevorzugt eine derartige Bleidioxyd-Titan-Verbundanode verwendet.A particularly preferred embodiment of the method according to the invention consists in using a metal oxide-titanium composite anode. Such composite anodes consist of a carrier made of titanium, which is provided with a metal oxide coating, an intermediate layer of a carbide or boride of the elements of the IV. And V. subgroup being applied to the titanium surface before the metal oxide coating is applied. Such a composite anode, namely a lead dioxide-titanium composite anode, and its production is described in German Patent 2,344,645. An improved method for producing such an anode is described in German Offenlegungsschrift No. 2,722,840. According to the invention, such a lead dioxide-titanium composite anode is preferably used.
Bei Verwendung von Mangandioxyd als Anodenmaterial kann dieses entweder auf Graphit oder auf Blei oder auch auf Bleidioxyd aufgebracht sein.If manganese dioxide is used as the anode material, this can be applied either to graphite or to lead or to lead dioxide.
Ferner können beim erfindungsgemässen mit Vorteil Graphitanoden verwendet werden.Furthermore, graphite anodes can advantageously be used in the case of the invention.
Weitere verwendbare Anodenmaterialien sind Edelmetalle, z.B. Platin oder platiniertes Titan.Other anode materials that can be used are precious metals, e.g. Platinum or platinum-plated titanium.
Die beim erfindungsgemässen Verfahren verwendeten Kathodenmaterialien sind nicht kritisch. Als Kathodenmaterialien sind beispielsweise Stahl, Nickel und Kupfer geeignet.Athodenmaterialien K used in the inventive process are not critical. Steel, nickel and copper, for example, are suitable as cathode materials.
Die Elektroden, und zwar sowohl die Anode wie auch die Kathode, können übliche Formen aufweisen. Beispielsweise können die Elektroden in Form von Platten oder Gittern oder als Streckmetall ausgebildet sein.The electrodes, both the anode and the cathode, can have customary shapes. For example, the electrodes can be designed in the form of plates or grids or as expanded metal.
Die Elektrolyse kann in ungeteilten oder in unterteilten Zellen durchgeführt werden, wobei im letzteren Falle die Unterteilung mit Membranen oder Diaphragmen aus üblichen Membran- bzw. Diaphragmen-Materialien erfolgen kann.The electrolysis can be carried out in undivided or in divided cells, in which case the latter can be divided with membranes or diaphragms made of conventional membrane or diaphragm materials.
Die angewandten Spannungen und Stromstärken richten sich nach dem verwendeten Lösungsmittel, nach der Grösse der Zelle und nach der angewandten Stromdichte. Im allgemeinen arbeitet man mit einer Spannung zwischen etwa 3 und etwa 20 V. Die Stromdichte kann innerhalb weiter Grenzen schwanken, wobei die Stromdichten im allgemeinen zwisehen etwa 0,01 und etwa 100 mA pro cm , insbesondere zwischen etwa 0,4 und etwa 50 mA pro cm2 betragen können.The voltages and currents used depend on the solvent used, the size of the cell and the current density used. In general, a voltage of between approximately 3 and approximately 20 V is used. The current density can vary within wide limits, the current densities generally between approximately 0.01 and approximately 100 mA per cm, in particular between approximately 0.4 and approximately 50 mA can be per cm 2 .
Die erfindungsgemässe Elektrolyse kann direkt in einem Gemisch eines Elektrolyten und des als Ausgangsmaterial verwendeten p-tert. Butyltoluol durchgeführt werden, wobei kein weiteres Lösungsmittel verwendet wird. Als Elektrolyten können beispielsweise wässrige Säuren, insbesondere nicht-oxidative Mineralsäuren verwendet werden. Als besonders geeignet hat sich hierbei die Schwefelsäure erwiesen. Zweckmässig arbeitet man hierbei mit einer 5-50%igen, insbesondere mit einer 7,5-15%igen wässrigen Schwefelsäure.The electrolysis according to the invention can be carried out directly in a mixture of an electrolyte and the p-tert used as the starting material. Butyltoluene are carried out using no other solvent. For example, aqueous acids, in particular non-oxidative mineral acids, can be used as electrolytes. Sulfuric acid has proven to be particularly suitable. It is expedient to work with a 5-50%, especially with a 7.5-15% aqueous sulfuric acid.
Besonders bevorzugt ist die Verwendung eines Gemisches, welches aus der oben genannten wässrigen Säure und einem inerten organischen Lösungsmittel besteht, beispielsweise einem Kohlenwasserstoff, wie Hexan, einem chlorierten Kohlenwasserstoff, wie Dichloräthan oder Methylenchlorid, einem tertiären niederen Alkanol, beispielsweise tert. Butanol, oder Aceton. Zweckmässig beträgt der Anteil des organischen Lösungsmittels im Gemisch etwa 10 bis etwa 60%. Wenn ein derartiges Gemisch als organische Komponente ein mit Wasser nicht mischbares organisches Lösungsmittel enthält oder wenn man überhaupt ohne Verwendung eines zusätzlichen Lösungsmittels arbeitet (Verwendung des Ausgangsmaterials als Lösungsmittel) wird zweckmässigerweise ein Phasentransferkatalysator verwendet, beispielsweise ein Tetraalkylammoniumsalz, wie Tetrabutylammoniumhydrogensulfat. Ein weiteres Beispiel eines solchen Phasentransfer-Katalysators ist das Dodecylhydrogensulfat-Natriumsalz.It is particularly preferred to use a mixture which consists of the above-mentioned aqueous acid and an inert organic solvent, for example a hydrocarbon such as hexane, a chlorinated hydrocarbon such as dichloroethane or methylene chloride, a tertiary lower alkanol, for example tert. Butanol, or acetone. The proportion of the organic solvent in the mixture is expediently from about 10 to about 60%. If such a mixture contains as an organic component a water-immiscible organic solvent or if one works at all without the use of an additional solvent (use of the starting material as solvent), a phase transfer catalyst is expediently used, for example a tetraalkylammonium salt such as tetrabutylammonium hydrogen sulfate. Another example of such a phase transfer catalyst is the dodecyl hydrogen sulfate sodium salt.
Bei Verwendung von Metalloxydanoden, insbesondere von Metalloxyd-Verbundanoden hat es sich als besonders zweckmässig erwiesen, als Lösungsmittel Dichloräthan zu verwenden, während sich bei Verwendung von Graphitanoden Aceton als Lösungsmittel als besonders vorteilhaft erwiesen hat.When using metal oxide anodes, in particular metal oxide composite anodes, it has proven to be particularly expedient to use dichloroethane as the solvent, while when using graphite anodes, acetone has proven to be particularly advantageous as solvent.
Insbesondere bei Verwendung von Graphitanoden bildet sich neben dem gewünschten p-tert. Butylbenzaldehyd in geringeren Mengen der entsprechende Alkohol. Dieser kann durch Destillation abgetrennt und in das Verfahren zurückgeführt, d.h. dem Ausgangsmaterial, p-tert. Butyltoluol, zugemischt werden.In particular when graphite anodes are used, in addition to the desired p-tert. Butylbenzaldehyde in smaller amounts the corresponding alcohol. This can be separated by distillation and returned to the process, i.e. the starting material, p-tert. Butyltoluene, can be added.
Die Konzentration des Ausgangsmaterials im verwendeten Elektrolytgemisch kann im allgemeinen zwischen etwa 1 und 80% schwanken, insbesondere zwischen etwa 10 und 50%, vorzugsweise zwischen etwa 10 und 20%.The concentration of the starting material in the electrolyte mixture used can generally vary between about 1 and 80%, in particular between about 10 and 50%, preferably between about 10 and 20%.
Die bei der Ausführung des erfindungsgemässen Verfahrens angewandte Temperatur ist nicht kritisch. Sie wird jedoch nach oben hin durch den Siedepunkt des Lö- sungsmittels begrenzt. Im allgemeinen arbeitet man zwischen Raumtemperatur und etwa 80°C, insbesondere zwischen Raumtemperatur und etwa 60 C.The temperature used in carrying out the method according to the invention is not critical. However, there is an upper limit on the boiling point of the solvent. Generally one works between room temperature and about 80 ° C, in particular between room temperature and about 60 C.
Dem Elektrolyten können in an sich bekannter Weise Metallsalze, beispielsweise Mangan-II-Salze, wie Mangan-II-Sulfat oder Cer-III-Salze, wie Cer-III-Sulfat zugesetzt werden und zwar in nur geringen Mengen, beispielsweise in einer Menge von etwa 1%o bezogen auf die Menge des Ansatzes.Metal salts, for example manganese-II salts, such as manganese-II sulfate, or cerium III salts, such as cerium-III sulfate, can be added to the electrolyte in a manner known per se, and only in small amounts, for example in an amount of about 1% based on the amount of the batch.
Während der Elektrolyse ist für kräftiges Durchmischen des Ansatzes zu sorgen.Ensure that the batch is thoroughly mixed during the electrolysis.
In ein Glasgefäss mit Deckel werden 2,5 ml p-tert. Butyltoluol, 10 ml Dichloräthan und 110 ml 10N Schwefelsäure gegeben und unter Magnetrührung emulgiert. Als Anode wird Titanstreckmetall (5 x 5 cm), beschichtet mit Blei- dioxyd, verwendet [Bleidioxyd-Titan-Verbundelektrode, beschrieben in Zeitschrift für Naturforschung "316, 39-50 (1976)], als Kathode dient ein Nickeldraht im Abstand von 3 cm von der Anode. Zwischen den Elektroden wird eine Spannung von 3,4 Volt angelegt, worauf sich ein Strom von 50 mA einstellt. Die Temperatur wird durch extreme Kühlung auf 25°C gehalten. Nach dem Durchgang von 1,55 Ah, was 100% des theoretisch benötigten Stromes entspricht, wird die Elektrolyse abgebrochen. Die Reaktionslösung wird dreimal mit je 60 ml Chloroform extrahiert und der kombinierte Extrakt im Gaschromatogramm quantitativ analysiert. Bei einem Umsatz von 83% resultiert eine Ausbeute an p-tert. Butylbenzaldehyd von 77% der Theorie.2.5 ml of p-tert are placed in a glass vessel with a lid. Butyltoluene, 10 ml dichloroethane and 110 ml 10N sulfuric acid and emulsified with magnetic stirring. Expanded titanium (5 x 5 cm) coated with lead dioxide is used as the anode [lead dioxide-titanium composite electrode, described in journal for natural research "316, 39-50 (1976)], a nickel wire at a distance of 3 is used as the cathode cm from the anode. A voltage of 3.4 volts is applied between the electrodes, which results in a current of 50 mA. The temperature is kept at 25 ° C. by extreme cooling. After the passage of 1.55 Ah, which is 100 % of the theoretically required current, the electrolysis is stopped, the reaction solution is extracted three times with 60 ml of chloroform and the combined extract is quantitatively analyzed in a gas chromatogram. With a conversion of 83%, a yield of p-tert-butylbenzaldehyde of 77% of the Theory.
In einer ungeteilten Elektrolysezelle, versehen mit einer Graphitfolie von 25 cm2 Oberfläche als Anode und einem Nickeldraht als Kathode, wird eine Lösung von 2,5 ml p-tert. Butyltoluol in 40 ml 3N wässriger Schwefelsäure und 80 ml Aceton bei Raumtemperatur, 0,75 A Stromstärke und 7,8-8,5 V Spannung unter Rühren elektrolysiert. Nach Beendigung der Elektrolyse (nach 2 Stunden) wird eine Probe entnommen.und mit Chloroform extrahiert. Die Produkte werden gaschromatographisch bestimmt. Bei einem Umsatz von 79% beträgt die Ausbeute an p-tert. Butylbenzaldehyd (bezogen, auf umgesetztes p-tert. Butyltoluol) 60 Mol%, die Ausbeute an p-tert. Butylbenzylalkohol 10 Mol%.In an undivided electrolysis cell, provided with a graphite foil with a surface area of 25 cm 2 as the anode and a nickel wire as the cathode, a solution of 2.5 ml of p-tert. Butyltoluene in 40 ml of 3N aqueous sulfuric acid and 80 ml of acetone at room temperature, 0.75 A current and 7.8-8.5 V voltage electrolyzed with stirring. After the electrolysis has ended (after 2 hours), a sample is taken and extracted with chloroform. The products are determined by gas chromatography. With a conversion of 79%, the yield of p-tert. Butylbenzaldehyde (based on converted p-tert. Butyltoluene) 60 mol%, the yield of p-tert. Butylbenzyl alcohol 10 mol%.
Claims (6)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT80105721T ATE7235T1 (en) | 1979-11-16 | 1980-09-24 | PROCESS FOR THE PRODUCTION OF P-TERT. BUTYLBENZALDEHYDE. |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH10254/79 | 1979-11-16 | ||
| CH1025479 | 1979-11-16 | ||
| CH6034/80 | 1980-08-08 | ||
| CH603480 | 1980-08-08 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0030588A1 true EP0030588A1 (en) | 1981-06-24 |
| EP0030588B1 EP0030588B1 (en) | 1984-04-25 |
Family
ID=25698867
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP80105721A Expired EP0030588B1 (en) | 1979-11-16 | 1980-09-24 | Process for the preparation of p-tert.-butylbenzaldehyde |
Country Status (2)
| Country | Link |
|---|---|
| EP (1) | EP0030588B1 (en) |
| DE (1) | DE3067628D1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4539081A (en) * | 1983-06-22 | 1985-09-03 | Basf Aktiengesellschaft | Preparation of benzaldehyde dialkyl acetals |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2351932A1 (en) * | 1976-05-21 | 1977-12-16 | Rhone Poulenc Ind | Anodic oxidn. of toluene and xylene(s) - to produce methyl benzyl ether(s) and methoxy benzaldehyde(s) |
| US4148696A (en) * | 1978-03-20 | 1979-04-10 | Uop Inc. | Electrochemical oxidation of activated alkyl aromatic compounds |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2855508A1 (en) * | 1978-12-22 | 1980-07-10 | Basf Ag | METHOD FOR PRODUCING BENZALDEHYDES |
-
1980
- 1980-09-24 EP EP80105721A patent/EP0030588B1/en not_active Expired
- 1980-09-24 DE DE8080105721T patent/DE3067628D1/en not_active Expired
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2351932A1 (en) * | 1976-05-21 | 1977-12-16 | Rhone Poulenc Ind | Anodic oxidn. of toluene and xylene(s) - to produce methyl benzyl ether(s) and methoxy benzaldehyde(s) |
| US4148696A (en) * | 1978-03-20 | 1979-04-10 | Uop Inc. | Electrochemical oxidation of activated alkyl aromatic compounds |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4539081A (en) * | 1983-06-22 | 1985-09-03 | Basf Aktiengesellschaft | Preparation of benzaldehyde dialkyl acetals |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0030588B1 (en) | 1984-04-25 |
| DE3067628D1 (en) | 1984-05-30 |
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