EP0012942B1 - Elektrolytisches Verfahren zur Herstellung von Benzaldehyden - Google Patents
Elektrolytisches Verfahren zur Herstellung von Benzaldehyden Download PDFInfo
- Publication number
- EP0012942B1 EP0012942B1 EP79105128A EP79105128A EP0012942B1 EP 0012942 B1 EP0012942 B1 EP 0012942B1 EP 79105128 A EP79105128 A EP 79105128A EP 79105128 A EP79105128 A EP 79105128A EP 0012942 B1 EP0012942 B1 EP 0012942B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- tert
- electrolysis
- formula
- acetate
- butylbenzyl
- 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
Links
- 238000000034 method Methods 0.000 title claims description 19
- 150000003935 benzaldehydes Chemical class 0.000 title description 8
- 238000005868 electrolysis reaction Methods 0.000 claims description 34
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 15
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims description 14
- 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 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 8
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 235000011054 acetic acid Nutrition 0.000 claims description 7
- 239000007858 starting material Substances 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- -1 tetrafluoroborate Chemical compound 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
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyloxyacetoaldehyde Natural products CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 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
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-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
- 150000001875 compounds Chemical class 0.000 claims description 3
- 238000002360 preparation method Methods 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
- 125000002887 hydroxy group Chemical group [H]O* 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
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 1
- OTXINXDGSUFPNU-UHFFFAOYSA-N 4-tert-butylbenzaldehyde Chemical compound CC(C)(C)C1=CC=C(C=O)C=C1 OTXINXDGSUFPNU-UHFFFAOYSA-N 0.000 description 19
- 239000003792 electrolyte Substances 0.000 description 11
- 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
- FVEINXLJOJPHLH-UHFFFAOYSA-N p-tert-Butylbenzyl alcohol Chemical compound CC(C)(C)C1=CC=C(CO)C=C1 FVEINXLJOJPHLH-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 235000019445 benzyl alcohol Nutrition 0.000 description 4
- 150000003938 benzyl alcohols Chemical class 0.000 description 4
- 230000005611 electricity Effects 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
- 150000005840 aryl radicals 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
- 229910000510 noble metal Inorganic materials 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 0 *c1ccc(C=O)cc1 Chemical compound *c1ccc(C=O)cc1 0.000 description 1
- 229910020366 ClO 4 Inorganic materials 0.000 description 1
- 241000234269 Liliales Species 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 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
- 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
- 238000006056 electrooxidation reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 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
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000005172 methylbenzenes Chemical class 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 229910017604 nitric acid Inorganic materials 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
- 239000002243 precursor Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003254 radicals Chemical class 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.
- Suitable alkyl radicals R 1 , R 2 and R 3 are those having 1 to 6, preferably 1 to 4, carbon atoms.
- aryl radicals R 1 phenyl radicals which may be substituted by alkyl, halogen, alkoxy and / or acyloxy groups may be mentioned.
- Starting materials of formula 11 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-butyltoluene, 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 111 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 111 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 NaC10 4 and Et 4 ClO 4 and sulfate such as Et 4 NS0 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 e.g. B. graphite, precious metals such as platinum and noble metal coated titanium electrodes.
- graphite, iron, steel, lead or noble 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 10A / dm 2 .
- the electrolysis itself is e.g. B. 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 e.g. B. further clean 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. But you can also isolate them before this return and according to known methods, for. B. by acidic transesterification with CH 3 0H / H 2 S0 4 , to saponify the corresponding benzyl alcohols.
- benzaldehydes obtainable by the process according to the invention are valuable intermediates for active substances and fragrances.
- 4-tert-butylbenzaldehyde takes place e.g. B. Use as a precursor 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)
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 EP0012942A2 (de) | 1980-07-09 |
| EP0012942A3 EP0012942A3 (en) | 1980-07-23 |
| EP0012942B1 true EP0012942B1 (de) | 1982-01-27 |
Family
ID=6058012
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP79105128A Expired EP0012942B1 (de) | 1978-12-22 | 1979-12-13 | Elektrolytisches Verfahren zur Herstellung von Benzaldehyden |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4235683A (enrdf_load_stackoverflow) |
| EP (1) | EP0012942B1 (enrdf_load_stackoverflow) |
| JP (1) | JPS5589487A (enrdf_load_stackoverflow) |
| DE (2) | DE2855508A1 (enrdf_load_stackoverflow) |
| DK (1) | DK149618C (enrdf_load_stackoverflow) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4164233A (en) * | 1978-03-07 | 1979-08-14 | Mcandrew James R | Vehicle covering apparatus |
| EP0030588B1 (de) * | 1979-11-16 | 1984-04-25 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | Verfahren zur Herstellung von p-tert. Butylbenzaldehyd |
| 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 |
| DE3132726A1 (de) * | 1981-08-19 | 1983-03-03 | Basf Ag, 6700 Ludwigshafen | Verfarhen zur herstellung von alkylsubstituierten benzaldehyden |
| GB8309571D0 (en) * | 1983-04-08 | 1983-05-11 | Albright & Wilson | Accelerated sealing of anodised aluminium |
| AU6672286A (en) * | 1986-01-06 | 1987-07-09 | Dow Chemical Company, The | Electrocatalytic method for producing quinone methides and dihydroxybenzophenones |
| 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 |
Family Cites Families (2)
| 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 |
| US4148696A (en) * | 1978-03-20 | 1979-04-10 | Uop Inc. | Electrochemical oxidation of activated alkyl aromatic compounds |
-
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 EP EP79105128A patent/EP0012942B1/de not_active Expired
- 1979-12-13 DE DE7979105128T patent/DE2962005D1/de 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
Also Published As
| Publication number | Publication date |
|---|---|
| DK149618B (da) | 1986-08-11 |
| DK149618C (da) | 1987-02-02 |
| DE2962005D1 (en) | 1982-03-11 |
| DK543079A (da) | 1980-06-23 |
| JPS5589487A (en) | 1980-07-07 |
| EP0012942A3 (en) | 1980-07-23 |
| US4235683A (en) | 1980-11-25 |
| DE2855508A1 (de) | 1980-07-10 |
| JPS6350434B2 (enrdf_load_stackoverflow) | 1988-10-07 |
| EP0012942A2 (de) | 1980-07-09 |
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