EP0012942A2 - Procédé de préparation électrolytique de benzaldéhydes - Google Patents

Procédé de préparation électrolytique de benzaldéhydes Download PDF

Info

Publication number: EP0012942A2
Authority: EP; European Patent Office
Prior art keywords: tert; electrolysis; formula; hydrogen atom; acetate
Prior art date: 1978-12-22
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.): Granted

Application number

EP79105128A

Other languages

German (de)

English (en)

Other versions

EP0012942A3 (en

EP0012942B1 (fr

Inventor

Dieter Dr. Dipl.-Chem. Degner

Hardo Dr. Dipl.-Chem. Siegel

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.)

1978-12-22

Filing date

1979-12-13

Publication date

1980-07-09

1979-12-13 Application filed by BASF SE filed Critical BASF SE

1980-07-09 Publication of EP0012942A2 publication Critical patent/EP0012942A2/fr

1980-07-23 Publication of EP0012942A3 publication Critical patent/EP0012942A3/xx

1982-01-27 Application granted granted Critical

1982-01-27 Publication of EP0012942B1 publication Critical patent/EP0012942B1/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 19
150000003935 benzaldehydes Chemical class 0.000 title claims abstract description 10
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 11
239000002253 acid Substances 0.000 claims abstract description 9
125000000217 alkyl group Chemical group 0.000 claims abstract description 7
-1 alkyl radical Chemical class 0.000 claims abstract description 7
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
150000005840 aryl radicals Chemical class 0.000 claims abstract description 4
150000001875 compounds Chemical class 0.000 claims abstract description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 3
238000005868 electrolysis reaction Methods 0.000 claims description 36
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 21
URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims description 16
QSCOAHKJRIJKQZ-UHFFFAOYSA-N (4-tert-butylphenyl)methyl acetate Chemical compound CC(=O)OCC1=CC=C(C(C)(C)C)C=C1 QSCOAHKJRIJKQZ-UHFFFAOYSA-N 0.000 claims description 13
QCWXDVFBZVHKLV-UHFFFAOYSA-N 1-tert-butyl-4-methylbenzene Chemical compound CC1=CC=C(C(C)(C)C)C=C1 QCWXDVFBZVHKLV-UHFFFAOYSA-N 0.000 claims description 13
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
150000003839 salts Chemical class 0.000 claims description 8
235000011054 acetic acid Nutrition 0.000 claims description 7
FVEINXLJOJPHLH-UHFFFAOYSA-N p-tert-Butylbenzyl alcohol Chemical compound CC(C)(C)C1=CC=C(CO)C=C1 FVEINXLJOJPHLH-UHFFFAOYSA-N 0.000 claims description 7
QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 claims description 6
239000007858 starting material Substances 0.000 claims description 6
WDCUPFMSLUIQBH-UHFFFAOYSA-N 4-Methylbenzyl alcohol acetate Chemical compound CC(=O)OCC1=CC=C(C)C=C1 WDCUPFMSLUIQBH-UHFFFAOYSA-N 0.000 claims description 5
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
KMTDMTZBNYGUNX-UHFFFAOYSA-N 4-methylbenzyl alcohol Chemical compound CC1=CC=C(CO)C=C1 KMTDMTZBNYGUNX-UHFFFAOYSA-N 0.000 claims description 3
229940007550 benzyl acetate Drugs 0.000 claims description 3
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 2
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 2
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
235000019253 formic acid Nutrition 0.000 claims description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 claims description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 2
WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 claims description 2
235000019260 propionic acid Nutrition 0.000 claims description 2
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 2
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 2
OTXINXDGSUFPNU-UHFFFAOYSA-N 4-tert-butylbenzaldehyde Chemical compound CC(C)(C)C1=CC=C(C=O)C=C1 OTXINXDGSUFPNU-UHFFFAOYSA-N 0.000 description 15
239000003792 electrolyte Substances 0.000 description 10
239000000463 material Substances 0.000 description 9
230000003647 oxidation Effects 0.000 description 9
238000007254 oxidation reaction Methods 0.000 description 9
238000009419 refurbishment Methods 0.000 description 8
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
229910020808 NaBF Inorganic materials 0.000 description 6
230000005611 electricity Effects 0.000 description 5
239000000203 mixture Substances 0.000 description 5
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
235000019445 benzyl alcohol Nutrition 0.000 description 4
150000003938 benzyl alcohols Chemical class 0.000 description 4
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
ZZLCFHIKESPLTH-UHFFFAOYSA-N 4-Methylbiphenyl Chemical compound C1=CC(C)=CC=C1C1=CC=CC=C1 ZZLCFHIKESPLTH-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
150000001299 aldehydes Chemical class 0.000 description 2
150000004996 alkyl benzenes Chemical class 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
238000004821 distillation Methods 0.000 description 2
239000003205 fragrance Substances 0.000 description 2
229910002804 graphite Inorganic materials 0.000 description 2
239000010439 graphite Substances 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
229910000510 noble metal Inorganic materials 0.000 description 2
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
239000000047 product Substances 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
229910020366 ClO 4 Inorganic materials 0.000 description 1
241000234269 Liliales Species 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
229910000831 Steel Inorganic materials 0.000 description 1
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
229940022663 acetate Drugs 0.000 description 1
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000013543 active substance Substances 0.000 description 1
125000004423 acyloxy group Chemical group 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
239000010405 anode material Substances 0.000 description 1
150000001555 benzenes Chemical class 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
150000001733 carboxylic acid esters Chemical class 0.000 description 1
238000001816 cooling Methods 0.000 description 1
230000005518 electrochemistry Effects 0.000 description 1
239000007772 electrode material Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000000417 fungicide Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical group 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
238000002955 isolation Methods 0.000 description 1
239000011133 lead Substances 0.000 description 1
SDQFDHOLCGWZPU-UHFFFAOYSA-N lilial Chemical compound O=CC(C)CC1=CC=C(C(C)(C)C)C=C1 SDQFDHOLCGWZPU-UHFFFAOYSA-N 0.000 description 1
150000005172 methylbenzenes Chemical class 0.000 description 1
BTFQKIATRPGRBS-UHFFFAOYSA-N o-tolualdehyde Chemical compound CC1=CC=CC=C1C=O BTFQKIATRPGRBS-UHFFFAOYSA-N 0.000 description 1
FXLOVSHXALFLKQ-UHFFFAOYSA-N p-tolualdehyde Chemical compound CC1=CC=C(C=O)C=C1 FXLOVSHXALFLKQ-UHFFFAOYSA-N 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
239000010970 precious metal Substances 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
238000004064 recycling Methods 0.000 description 1
SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
239000010959 steel Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000010936 titanium Substances 0.000 description 1
229910052719 titanium Inorganic materials 0.000 description 1
238000005809 transesterification reaction Methods 0.000 description 1
230000007306 turnover Effects 0.000 description 1

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 invention relates to a method for the electrochemical production of benzaldehydes.
R 1 represents a hydrogen atom, an alkyl radical or an aryl radical
R 2 represents a hydrogen atom or an.alkyl group with 1 to 6 C atoms
R 3 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms
Suitable alkyl radicals R 1 , R 2 and R 3 are those having 1 to 6, preferably 1 to 4, carbon atoms. Phenyl radicals which can be substituted by alkyl, halogen, alkoxy and / or acyloxy groups may be mentioned as aryl radicals R 1 .
Starting materials of formula II are thus methylbenzenes, benzyl alcohols or the alkanoic acid esters of benzyl alcohols which are not substituted in the 4-position or contain the radical R 1 mentioned , such as toluene, p-xylene, p-tert-butyl-toluene, p-phenyltoluene , Benzyl alcohol, p-methylbenzyl alcohol, p-tert-butylbenzyl alcohol, benzyl acetate, p-methylbenzyl acetate and p-tert-butylbenzyl acetate.
Preferred alkanoic acids of formula III are formic acid, acetic acid and propionic acid.
a mixture of the benzene derivative of the formula II, water and the alkanoic acid of the formula III is used as the electrolyte, which may additionally contain a conductive salt to improve the conductivity.
the usual salts in organic electrochemistry can be used as the conductive salts, which are soluble in the solution to be electrolyzed and largely stable under the test conditions.
Fluoride such as NaF and KF, tetrafluoroborate such as NaBF 4 and Et 4 NBF 4 , perchlorate such as NaClO 4 and Et 4 ClO 4 and sulfate such as Et 4 NSO 4 Et are particularly advantageous as conductive salts.
the composition of the electrolyte can be chosen within wide limits.
the solutions used in electrolysis have the following composition, for example:
the electrode materials used in the process according to the invention will be those which are stable under the conditions of the electrolysis.
Suitable anode materials are, for example, graphite, noble metals such as platinum and noble metal coated titanium electrodes.
graphite, iron, steel, lead or precious metal electrodes are used as cathodes.
Current density and turnover can also be selected within wide limits. The current density is, for example, 1 to 10 A / dm 2 .
the electrolysis itself is, for example. with 2 to 12, preferably 4 to 12 F / mol of starting compound and at temperatures below 100 ° C, advantageously between 10 and 90 ° C.
the method according to the invention can be carried out both in divided and in undivided electrolysis cells.
the electrolysis discharges are generally worked up by distillation. Alkanoic acid, water and any starting materials still present are separated from the benzaldehydes by distillation and can be returned to the electrolysis.
the conductive salts used can then be separated from the aldehydes, for example by filtration, and can also be used again in the electrolysis.
the benzaldehydes can be further purified, for example, by rectification.
the carboxylic acid esters of the corresponding benzyl alcohols obtained as by-products in the process according to the invention can be returned to the electrolysis. However, they can also be isolated before this recycling and saponified to the corresponding benzyl alcohols by processes known per se, for example by acidic transesterification with CH 3 OH / H 2 SO 4 .
benzaldehydes obtainable by the process according to the invention are valuable intermediates for active substances and fragrances.
4-tert-butylbenzaldehyde finds e.g. Use as a preliminary product for fungicides and serves as a starting material for the fragrance Lilial.
the electrolyte is pumped through a heat exchanger during the electrolysis.
the electrolyte is pumped through a heat exchanger during the electrolysis.
the electrolyte is pumped through a heat exchanger during the electrolysis.
the electrolyte is pumped through a heat exchanger during the electrolysis.
the electrolyte is pumped through a heat exchanger during the electrolysis.
the electrolyte is pumped through a heat exchanger during the electrolysis.
the electrolyte is pumped through a heat exchanger during the electrolysis.
the electrolyte is pumped through a heat exchanger during the electrolysis.

Landscapes

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)

EP79105128A 1978-12-22 1979-12-13 Procédé de préparation électrolytique de benzaldéhydes Expired EP0012942B1 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19782855508 DE2855508A1 (de)	1978-12-22	1978-12-22	Verfahren zur herstellung von benzaldehyden
DE2855508		1978-12-22

Publications (3)

Publication Number	Publication Date
EP0012942A2 true EP0012942A2 (fr)	1980-07-09
EP0012942A3 EP0012942A3 (en)	1980-07-23
EP0012942B1 EP0012942B1 (fr)	1982-01-27

Family

ID=6058012

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
EP79105128A Expired EP0012942B1 (fr)	1978-12-22	1979-12-13	Procédé de préparation électrolytique de benzaldéhydes

Country Status (5)

Country	Link
US (1)	US4235683A (fr)
EP (1)	EP0012942B1 (fr)
JP (1)	JPS5589487A (fr)
DE (2)	DE2855508A1 (fr)
DK (1)	DK149618C (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0072914A1 (fr) *	1981-08-19	1983-03-02	BASF Aktiengesellschaft	Procédé de préparation de benzaldéhydes alcoxy-substitués
EP0030588B1 (fr) *	1979-11-16	1984-04-25	F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft	Procédé de préparation de p-tert.-butylbenzaldéhyde
EP0231053A1 (fr) *	1986-01-06	1987-08-05	The Dow Chemical Company	Procédé électrocatalytique pour la préparation de méthides de quinone et de dihydroxybenzophénones

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4164233A (en) *	1978-03-07	1979-08-14	Mcandrew James R	Vehicle covering apparatus
DE2948455A1 (de) *	1979-12-01	1981-06-11	Basf Ag, 6700 Ludwigshafen	Verfahren zur herstellung von 4-tert. butylbenzaldehyd.
US4387007A (en) *	1980-11-17	1983-06-07	Hoffmann-La Roche Inc.	Process for the manufacture of an aldehyde
GB8309571D0 (en) *	1983-04-08	1983-05-11	Albright & Wilson	Accelerated sealing of anodised aluminium
DE3913166A1 (de) *	1989-04-21	1990-10-25	Basf Ag	Verfahren zur herstellung von benzaldehyddialkylacetalen und neue benzaldehyddialkylacetale und benzylester
KR102307579B1 (ko) *	2019-09-18	2021-10-05	한국과학기술연구원	벤즈알데하이드 제조방법

Citations (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4148696A (en) *	1978-03-20	1979-04-10	Uop Inc.	Electrochemical oxidation of activated alkyl aromatic compounds

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS583035B2 (ja) *	1976-04-12	1983-01-19	株式会社クラレ	パラフェノキシトルエンの酸化方法

1978
- 1978-12-22 DE DE19782855508 patent/DE2855508A1/de not_active Withdrawn
1979
- 1979-12-05 US US06/100,654 patent/US4235683A/en not_active Expired - Lifetime
- 1979-12-13 DE DE7979105128T patent/DE2962005D1/de not_active Expired
- 1979-12-13 EP EP79105128A patent/EP0012942B1/fr not_active Expired
- 1979-12-19 DK DK543079A patent/DK149618C/da not_active IP Right Cessation
- 1979-12-21 JP JP16580779A patent/JPS5589487A/ja active Granted

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4148696A (en) *	1978-03-20	1979-04-10	Uop Inc.	Electrochemical oxidation of activated alkyl aromatic compounds

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, Band 19 (1925), Seite 783, C.A. MANN et al.: "Electrochemical oxidation of toluene to benzaldehyde", & Trans.Am.Electrochem.Soc. 47 (preprint), 1925. *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0030588B1 (fr) *	1979-11-16	1984-04-25	F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft	Procédé de préparation de p-tert.-butylbenzaldéhyde
EP0072914A1 (fr) *	1981-08-19	1983-03-02	BASF Aktiengesellschaft	Procédé de préparation de benzaldéhydes alcoxy-substitués
EP0231053A1 (fr) *	1986-01-06	1987-08-05	The Dow Chemical Company	Procédé électrocatalytique pour la préparation de méthides de quinone et de dihydroxybenzophénones

Also Published As

Publication number	Publication date
DE2962005D1 (en)	1982-03-11
EP0012942A3 (en)	1980-07-23
DK149618C (da)	1987-02-02
DK543079A (da)	1980-06-23
JPS6350434B2 (fr)	1988-10-07
JPS5589487A (en)	1980-07-07
US4235683A (en)	1980-11-25
DK149618B (da)	1986-08-11
EP0012942B1 (fr)	1982-01-27
DE2855508A1 (de)	1980-07-10

Publication	Publication Date	Title
EP0011712B1 (fr)	1983-06-15	La préparation de dialcoylacétals de benzaldéhyd substitués en position 4
DE2343054B1 (de)	1975-02-06	Verfahren zur elektrochemischen Herstellung von Pinacolen
EP0012942B1 (fr)	1982-01-27	Procédé de préparation électrolytique de benzaldéhydes
EP0072914B1 (fr)	1984-10-31	Procédé de préparation de benzaldéhydes alcoxy-substitués
EP0275489B1 (fr)	1989-08-09	Dérivés de benzaldéhyde, leur fabrication et leur utilisation
EP0902846B1 (fr)	2000-07-26	Procede pour preparer des phtalides
EP0287954A2 (fr)	1988-10-26	Acétals dialkyls de benzaldéhyde, leur préparation et leur utilisation
DE3322399A1 (de)	1985-01-10	Verfahren zur herstellung von benz aldehyddialkylacetalen
EP0638665B1 (fr)	1996-10-30	Procédé pour la préparation d'acetals dialkyls de benzaldehyde
EP0502372B1 (fr)	1995-05-17	Dialkylacétals de 4-tert-alkyl-2-méthylbenzaldéhydes
EP0029995B1 (fr)	1983-05-11	Procédé de préparation de 4-tert-butyl-benzaldéhyde
EP0393668B1 (fr)	1994-02-02	Procédé de préparation d'acétals dialkyls de benzaldéhyde et acétals dialkyls de benzaldéhyde
EP0347690B1 (fr)	1992-10-21	Procédé de préparation de dérivés du benzène et dérivés du benzène
EP0152801B1 (fr)	1987-05-27	Procédé de production de dialkylacétals de benzaldéhyde
US3396093A (en)	1968-08-06	Electrochemical synthesis of ketones
EP0292889B1 (fr)	1992-09-02	Dérivés de la benzaldéhyde, leur préparation et leur utilisation
EP0053261B1 (fr)	1983-12-21	Procédé pour la préparation d'un mélange de cétals de la triméthyl p-benzoquinone
EP0525351B1 (fr)	1995-04-05	Esters alkylique d'acide 2-aryle-2,2-dialcoxyacétique, procédé pour leur préparation et utilisation dans la préparation d'esters d'acide aryleglyoxylique
EP0164705A2 (fr)	1985-12-18	Procédé de production de phtalaldéhydacétals
EP0339521B1 (fr)	1992-03-18	Procédé de préparation de dérivés de tétraline et dérivés de tétraline
DE2345461C3 (de)	1977-02-24	Verfahren zur Herstellung von Pinacol durch elektrolytische Hydrodimerisierung von Aceton
DE2758882A1 (de)	1979-07-05	Verfahren zur herstellung von cis-7,8-epoxy-2-methyloctadecan
DD158650A1 (de)	1983-01-26	Verfahren zur herstellung von 2-(2,2-dichlorvinyloxy)-bzw.2-(2,2-dichlervinylthio)-carbonsaeuren sowie ihrer ester
EP0711851A1 (fr)	1996-05-15	Procédé de production de p-Hydroxybenzaldéhydes
DD283162A5 (de)	1990-10-03	Verfahren zur herstellung von 4-ethoxybenzaldehydacetalen

Legal Events

Date	Code	Title	Description
1980-05-13	PUAI	Public reference made under article 153(3) epc to a published international application that has entered the european phase	Free format text: ORIGINAL CODE: 0009012
1980-05-22	PUAL	Search report despatched	Free format text: ORIGINAL CODE: 0009013
1980-07-09	AK	Designated contracting states	Designated state(s): CH DE FR GB IT SE
1980-07-23	AK	Designated contracting states	Designated state(s): CH DE FR GB IT SE
1980-11-26	17P	Request for examination filed
1981-10-02	ITF	It: translation for a ep patent filed
1981-11-27	GRAA	(expected) grant	Free format text: ORIGINAL CODE: 0009210
1981-11-27	STAA	Information on the status of an ep patent application or granted ep patent	Free format text: STATUS: THE PATENT HAS BEEN GRANTED
1982-01-27	AK	Designated contracting states	Designated state(s): CH DE FR GB IT SE
1982-03-11	REF	Corresponds to:	Ref document number: 2962005 Country of ref document: DE Date of ref document: 19820311
1990-12-31	ITTA	It: last paid annual fee
1995-01-31	EAL	Se: european patent in force in sweden	Ref document number: 79105128.7
1998-11-27	PGFP	Annual fee paid to national office [announced via postgrant information from national office to epo]	Ref country code: FR Payment date: 19981127 Year of fee payment: 20
1998-11-30	PGFP	Annual fee paid to national office [announced via postgrant information from national office to epo]	Ref country code: SE Payment date: 19981130 Year of fee payment: 20
1998-12-03	PGFP	Annual fee paid to national office [announced via postgrant information from national office to epo]	Ref country code: GB Payment date: 19981203 Year of fee payment: 20
1998-12-08	PGFP	Annual fee paid to national office [announced via postgrant information from national office to epo]	Ref country code: CH Payment date: 19981208 Year of fee payment: 20
1998-12-24	PGFP	Annual fee paid to national office [announced via postgrant information from national office to epo]	Ref country code: DE Payment date: 19981224 Year of fee payment: 20
1999-12-12	PG25	Lapsed in a contracting state [announced via postgrant information from national office to epo]	Ref country code: GB Free format text: LAPSE BECAUSE OF EXPIRATION OF PROTECTION Effective date: 19991212 Ref country code: CH Free format text: LAPSE BECAUSE OF EXPIRATION OF PROTECTION Effective date: 19991212
1999-12-30	PG25	Lapsed in a contracting state [announced via postgrant information from national office to epo]	Ref country code: SE Free format text: THE PATENT HAS BEEN ANNULLED BY A DECISION OF A NATIONAL AUTHORITY Effective date: 19991230
2000-01-12	REG	Reference to a national code	Ref country code: GB Ref legal event code: PE20 Effective date: 19991212
2000-01-14	REG	Reference to a national code	Ref country code: CH Ref legal event code: PL
2000-02-28	EUG	Se: european patent has lapsed	Ref document number: 79105128.7
2016-09-14	PLBE	No opposition filed within time limit	Free format text: ORIGINAL CODE: 0009261

EP0012942A2 - Procédé de préparation électrolytique de benzaldéhydes - Google Patents

Info

Links

Classifications

Definitions

Landscapes

Applications Claiming Priority (2)

Publications (3)

Family

ID=6058012

Family Applications (1)

Country Status (5)

Cited By (3)

Families Citing this family (6)

Citations (1)

Family Cites Families (1)

Patent Citations (1)

Non-Patent Citations (1)

Cited By (3)

Also Published As

Similar Documents

Legal Events