EP0029995B1 - Verfahren zur Herstellung von 4-tert. Butylbenzaldehyd - Google Patents

Verfahren zur Herstellung von 4-tert. Butylbenzaldehyd Download PDF

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Publication number
EP0029995B1
EP0029995B1 EP80107345A EP80107345A EP0029995B1 EP 0029995 B1 EP0029995 B1 EP 0029995B1 EP 80107345 A EP80107345 A EP 80107345A EP 80107345 A EP80107345 A EP 80107345A EP 0029995 B1 EP0029995 B1 EP 0029995B1
Authority
EP
European Patent Office
Prior art keywords
tert
acid
electrolysis
butylbenzaldehyde
butyltoluene
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.)
Expired
Application number
EP80107345A
Other languages
German (de)
English (en)
French (fr)
Other versions
EP0029995A1 (de
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
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 SE filed Critical BASF SE
Publication of EP0029995A1 publication Critical patent/EP0029995A1/de
Application granted granted Critical
Publication of EP0029995B1 publication Critical patent/EP0029995B1/de
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. When the synthesis is carried out industrially, 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 in the presence of mineral acids can be produced considerably more advantageously if the electrochemical oxidation is carried out in the presence of additional alkyl, alkenyl or arylsulfonic acids. 4-tert. Butylbenzaldehyde in high yield.
  • Another major advantage of the method according to the invention is the simple processing 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. You can e.g. B. in the technically frequently used plate and frame cell.
  • the electrolyte consists of 4-tert. Butyltoluene and an aqueous solution of a mineral acid to which small amounts of an alkyl, alkenyl or arylsulfonic acid are added.
  • a mineral acid to which small amounts of an alkyl, alkenyl or arylsulfonic acid are 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 are: aliphatic sulfonic acids, such as the acids of the formulas C 14 H 29 SO 3 H, C 16 H 33 SO 3 H and C 17 H 35 SO 3 H, or aliphatic-aromatic sulfonic acids, such as benzenesulfonic acids, on the benzene ring still carry alkyl radicals of the formulas C 10-14 H 21-29 , or butylnaphthalenesulfonic acid. Mixtures of sulfonic acids can also be used.
  • Suitable anode materials are e.g. B. lead dioxide or titanium coated with lead dioxide.
  • lead, iron, steel or graphite electrodes are used as cathodes.
  • 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.

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 Verfahren zur Herstellung von 4-tert. Butylbenzaldehyd Expired EP0029995B1 (de)

Applications Claiming Priority (2)

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

Publications (2)

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

Family

ID=6087391

Family Applications (1)

Application Number Title Priority Date Filing Date
EP80107345A Expired EP0029995B1 (de) 1979-12-01 1980-11-25 Verfahren zur Herstellung von 4-tert. Butylbenzaldehyd

Country Status (5)

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

Families Citing this family (6)

* 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
DE3913166A1 (de) * 1989-04-21 1990-10-25 Basf Ag Verfahren zur herstellung von benzaldehyddialkylacetalen und neue benzaldehyddialkylacetale und benzylester
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
JP2013519637A (ja) 2010-02-11 2013-05-30 ビーエーエスエフ ソシエタス・ヨーロピア 触媒としてイオン液体を用いる異性化によるｍ−置換アルキルトルエンの製造方法

Family Cites Families (2)

* 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
DE2855508A1 (de) * 1978-12-22 1980-07-10 Basf Ag Verfahren zur herstellung von benzaldehyden

Also Published As

Publication number Publication date
EP0029995A1 (de) 1981-06-10
DE2948455A1 (de) 1981-06-11
US4298438A (en) 1981-11-03
JPS5693882A (en) 1981-07-29
DE3063185D1 (en) 1983-06-16
CA1152936A (en) 1983-08-30
JPS6330992B2 (enrdf_load_stackoverflow) 1988-06-21

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