EP0029995A1 - Procédé de préparation de 4-tert-butyl-benzaldéhyde - Google Patents

Procédé de préparation de 4-tert-butyl-benzaldéhyde Download PDF

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Publication number
EP0029995A1
EP0029995A1 EP80107345A EP80107345A EP0029995A1 EP 0029995 A1 EP0029995 A1 EP 0029995A1 EP 80107345 A EP80107345 A EP 80107345A EP 80107345 A EP80107345 A EP 80107345A EP 0029995 A1 EP0029995 A1 EP 0029995A1
Authority
EP
European Patent Office
Prior art keywords
tert
butylbenzaldehyde
electrolysis
butyltoluene
acids
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.)
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Application number
EP80107345A
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German (de)
English (en)
Other versions
EP0029995B1 (fr
Inventor
Dieter Dr. Degner
Hardo Dr. Siegel
Heinz Hannebaum
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.)
BASF SE
Original Assignee
BASF SE
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Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Publication of EP0029995A1 publication Critical patent/EP0029995A1/fr
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Publication of EP0029995B1 publication Critical patent/EP0029995B1/fr
Expired legal-status Critical Current

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Classifications

    • 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 the electrochemical production of 4-tert. Butylbenzaldehyde.
  • the nucleic and side chain-substituted fatty acid esters also form as by-products in this process. Furthermore, the processing of the electrolysis discharges requires a number of separation operations. In a technical implementation of the synthesis, the fatty acids and fatty acid salts must be separated from the benzaldehydes and recycled, and then the benzaldehydes must be separated from the fatty acid esters.
  • 4-tert-butylbenzaldehyde is obtained by electrochemical oxidation of 4-tert. Butyltoluene can be produced significantly more advantageously in the presence of mineral acids if the electrochemical oxidation is carried out in the presence of alkyl, alkenyl or arylsulfonic acids. 4-tert. Butylbenzaldehyde in high yield.
  • the main advantage of the method according to the invention is the simple workup of the electrolysis discharges. Thus, after the electrolysis has ended, the 4-tert can be obtained from the organic phase obtained by phase separation. Isolate butylbenzaldehyde directly by distillation.
  • the new process can be carried out batchwise or continuously. Electrolysis does not require a special electrolysis cell. It can be carried out, for example, in the technically frequently used plate and frame cell.
  • the electrolyte consists of 4-tert. Butyltoluene and an aqueous solution of a mineral r alklare, the small amounts of an alkyl, alkenyl or A rylsulfonklare be added.
  • sulfuric acid is used as the mineral acid.
  • Long-chain alkyl sulfonic acids, alkenyl sulfonic acids or aryl sulfonic acids which additionally carry alkyl groups in the aryl radical are preferably used as sulfonic acid.
  • Long-chain alkyl sulfonic acids or alkenyl sulfonic acids are understood to mean those with at least 6 carbon atoms.
  • Suitable sulfonic acids which may be mentioned: aliphatic sulfonic acids, such as the acids of formulas C14H29S03H, C 16 H 33 SO 3 H and C 17 H 35 S0 3 H or aliphatic-aromatic sulphonic acids, such enzolsulfonkla B, on the benzene ring or alkyl radicals of the formulas C 10 -14 H 21-29 wear, or butylnaphthalenesulfonic acid. Mixtures of sulfonic acids can also be used.
  • the electrolytes used in the electrolysis have. for example the following composition: 5 to 50 wt.% 4-tert. Butyltoluene, 0.5 to 10 wt.% Sulfuric acid, 40 to 90 wt.% Of water and from 0.05 to 5 'wt.% Sulfonic acid.
  • Suitable anode materials are, for example, lead dioxide or titanium coated with lead dioxide.
  • cathodes are at for example, lead, iron, steel or graphite electrodes are used.
  • the electrolysis itself is carried out at current densities of 1 to 10 A / dm 2 and temperatures between 10 and 90 ° C.
  • the 4-tert. Butyltoluene conversion is preferably 10 to 50%.
  • the electrolysis discharges are preferably worked up by distillation. After phase separation, the organic phase is distilled in vacuo.
  • the electrolyte is pumped through a heat exchanger during the electrolysis. After the electrolysis has ended, the phases are separated and the organic phase is distilled off at two torr and 60 to 120 ° C. In addition to 180 g of unreacted 4-tert. Butyltoluene 92.4 g 4-tert-butylbenzaldehyde. This corresponds to a yield of 70.4

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Electrochemistry (AREA)
  • Materials Engineering (AREA)
  • Metallurgy (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)
EP80107345A 1979-12-01 1980-11-25 Procédé de préparation de 4-tert-butyl-benzaldéhyde Expired EP0029995B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19792948455 DE2948455A1 (de) 1979-12-01 1979-12-01 Verfahren zur herstellung von 4-tert. butylbenzaldehyd.
DE2948455 1979-12-01

Publications (2)

Publication Number Publication Date
EP0029995A1 true EP0029995A1 (fr) 1981-06-10
EP0029995B1 EP0029995B1 (fr) 1983-05-11

Family

ID=6087391

Family Applications (1)

Application Number Title Priority Date Filing Date
EP80107345A Expired EP0029995B1 (fr) 1979-12-01 1980-11-25 Procédé de préparation de 4-tert-butyl-benzaldéhyde

Country Status (5)

Country Link
US (1) US4298438A (fr)
EP (1) EP0029995B1 (fr)
JP (1) JPS5693882A (fr)
CA (1) CA1152936A (fr)
DE (2) DE2948455A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5078838A (en) * 1989-04-21 1992-01-07 Basf Aktiengesellschaft Preparation of benzaldehyde dialkyl acetals and novel benzaldehyde dialkyl acetals and benzyl esters
US8367875B2 (en) 2010-02-11 2013-02-05 Basf Se Process for the preparation of m-substituted alkyltoluenes by isomerization with ionic liquids as catalysts

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS58502027A (ja) * 1981-11-23 1983-11-24 バロ−ス・コ−ポレ−ション 低デ−タ転送率の直列入出力インタ−フェイスをモニタするようにされた周辺装置
US4402804A (en) * 1982-05-17 1983-09-06 Ppg Industries, Inc. Electrolytic synthesis of aryl alcohols, aryl aldehydes, and aryl acids
DE3322399A1 (de) * 1983-06-22 1985-01-10 Basf Ag, 6700 Ludwigshafen Verfahren zur herstellung von benz aldehyddialkylacetalen
MX2012008474A (es) 2010-02-11 2012-08-15 Basf Se Proceso para preparar alquiltoluenos m - sustituidos por isomerizacion con liquidos ionicos como catalizadores.

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2351932A1 (fr) * 1976-05-21 1977-12-16 Rhone Poulenc Ind Procede d'oxydation anodique de methylbenzenes

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2855508A1 (de) * 1978-12-22 1980-07-10 Basf Ag Verfahren zur herstellung von benzaldehyden

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2351932A1 (fr) * 1976-05-21 1977-12-16 Rhone Poulenc Ind Procede d'oxydation anodique de methylbenzenes

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5078838A (en) * 1989-04-21 1992-01-07 Basf Aktiengesellschaft Preparation of benzaldehyde dialkyl acetals and novel benzaldehyde dialkyl acetals and benzyl esters
US8367875B2 (en) 2010-02-11 2013-02-05 Basf Se Process for the preparation of m-substituted alkyltoluenes by isomerization with ionic liquids as catalysts

Also Published As

Publication number Publication date
US4298438A (en) 1981-11-03
EP0029995B1 (fr) 1983-05-11
CA1152936A (fr) 1983-08-30
DE2948455A1 (de) 1981-06-11
JPS6330992B2 (fr) 1988-06-21
JPS5693882A (en) 1981-07-29
DE3063185D1 (en) 1983-06-16

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