EP1348043B1 - Verfahren zur herstellung von alkoxylierten carbonylverbindungen durch ein anodisches oxidationsverfahren unter nutzung der kathodischen koppelreaktion zur organischen synthese - Google Patents
Verfahren zur herstellung von alkoxylierten carbonylverbindungen durch ein anodisches oxidationsverfahren unter nutzung der kathodischen koppelreaktion zur organischen synthese Download PDFInfo
- Publication number
- EP1348043B1 EP1348043B1 EP01994702A EP01994702A EP1348043B1 EP 1348043 B1 EP1348043 B1 EP 1348043B1 EP 01994702 A EP01994702 A EP 01994702A EP 01994702 A EP01994702 A EP 01994702A EP 1348043 B1 EP1348043 B1 EP 1348043B1
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- EP
- European Patent Office
- Prior art keywords
- compounds
- alkyl
- derivatives
- substituted
- acid
- 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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Classifications
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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
Definitions
- the present invention relates to a process for the preparation of formaldehyde di (C 1 to C 6 alkyl) acetals, ortho-formic acid tri- (C 1 to C 6 alkyl) esters, acetaldehyde di ( C 1 - to C 6 -alkyl) - acetals or ortho-acetic tri- (C 1 - to C 6 -alkyl) esters (compounds 1) by anodic oxidation of 1,2-di- (C 1 - to C 6 - alkoxy) ethane or propane, 1,1,2,2-tetra (C 1 to C 6 alkoxy) ethane or propane, or 2,3-di- (C 1 to C 6 alkoxy) -butane (compounds II) in the presence of a C 1 - to C 6 -alkyl alcohol (compounds III) in which the cathodic depolarizer used is a customary organic compound (compounds IV) which is suitable for electrochemical reduction and in
- compounds II are 1,2-di (C 1 - to C 6 alkoxy) ethane or propane or 1,1,2,2-tetra (C 1 - to C 6 alkoxy) ethane or -propane used.
- compounds I the corresponding formaldehyde di (C 1 - to C 6 alkyl) acetals or ortho-antric acid tri (C 1 - to C 6 alkyl) esters are formed and, in the case of the propane derivatives as starting materials also acetaldehyde di- (C 1 - to C 6 alkyl) - acetals or Orthoessigklatri- (C 1 - to C 6 alkyl) ester.
- the abovementioned acetaldehyde or acetic acid derivatives can likewise be prepared from 2,3-di- (C 1 -C 6 -alkoxy) -butane.
- cathodic Depolisatoren come usual organic Compounds suitable for anodic reduction, such as aromatic hydrocarbon compounds, activated olefins, Carbonyl compounds, aromatic carboxylic acids and their derivatives and naphthalene or nucleus-substituted naphthalene derivatives.
- Suitable substituents with which the aromatic nuclei can be substituted in the abovementioned starting compounds are inert, hardly reducible groups, such as C 1 -C 12 -alkyl, C 1 -C 6 -alkoxy or halogen.
- the molar ratio of the starting compounds for cathode and Anode reaction and the products formed in these reactions in electrolytes to each other is not critical.
- Conducting salts which are contained in the electrolysis solution are generally alkali, tetra (C 1 - to C 6 -alkyl) -ammonium or tri- (C 1 - to C 6 -alkyl) -benzylammonium salts.
- Suitable counterions are sulfate, hydrogensulfate, alkyl sulfates, alkyl sulfonates, halides, phosphates, carbonates, alkyl phosphates, alkyl carbonates, nitrate, alcoholates, tetrafluoroborate or perchlorate.
- MTBS methyltributylammonium methylsulfate
- methyltriethylammonium methylsulfate methyltriethylammonium methylsulfate
- methyl tripropylmethylammonium methyl sulfates Preference is given to methyltributylammonium methylsulfate (MTBS), methyltriethylammonium methylsulfate or methyl tripropylmethylammonium methyl sulfates.
- the electrolysis solution is subjected to customary cosolvents to. These are those in organic chemistry Commonly used inert solvents with a high oxidation potential. Examples include dimethyl carbonate or Propylene carbonate.
- the process of the invention can be in all the usual undivided Electrolysis cell types are performed. Preferably works one continuously with undivided flow cells. Especially plate stack cells with serially designed stacking electrodes are suitable, as described for example in DE-A-19533773 are.
- the current densities at which the process is carried out are generally 1 to 1000, preferably 10 to 100 mA / cm 2 .
- the temperatures are usually -20 to 60 ° C, preferably 0 to 60 ° C. In general, working at atmospheric pressure. Higher pressures are preferably used when operating at higher temperatures to avoid boiling of the starting compounds or cosolvents.
- Suitable anode materials are, for example, noble metals such as platinum or metal oxides such as ruthenium or chromium oxide or mixed oxides of the type Ruo x Tio x . Preference is given to graphite or carbon electrodes.
- cathode materials are, for example, iron, steel, stainless steel, Nickel or precious metals such as platinum and graphite or carbon materials into consideration.
- the system is graphite Anode and cathode as well as graphite as anode and nickel, stainless steel or steel as a cathode.
- the electrolyte solution is after worked up general separation methods.
- the electrolysis solution generally distilled first and the individual Compounds separated in the form of different fractions won. Further purification can be carried out, for example, by crystallization, Distillation or by chromatography.
- 11 ring disk electrodes each having a surface area of 140 cm 2 and an outer diameter of 14 cm are arranged so as to form a stack. By spacers, the discs are set to a distance of 1 mm, resulting in 10 gaps between the annular discs.
- the electrode material is graphite. Under electrolysis conditions, the inner 0.5 cm thick disks are bipolar.
- the top electrode is anodically contacted by means of a graphite punch and a cover plate, the bottom electrode is cathodically contacted, the cathodic contact extends over the bottom plate of the cell.
- the electrolyte flows through the central bore of the bottom plate into the cell, spreads over the column and leaves the cell above the top electrode.
- the cell is part of a circulating apparatus in which the electrolyte is circulated, heated or cooled.
- the electrolysis effluent contained 24.4% butanetetracarboxylic acid methyl ester, 14.2% trimethyl orthoformate, 25.6% tetramethoxyethane and 1.7% maleic dimethyl ester.
- the selectivity the orthoester formation was 82%.
- the composition of the electrolysis discharge was determined by gas chromatograph and is in area% (GC area%).
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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)
Description
wobei man als kathodischen Depolarisator eine übliche organische Verbindung (Verbindungen IV) einsetzt, die sich für die elektrochemische Reduktion eignet und wobei man die anodische Oxidation und die kathodische Reduktion in einer ungeteilten Elektrolysezelle in Gegenwart von C1-C6-Alkylalkoholen ausführt.
Claims (5)
- Verfahren zur Herstellung von Formaldehyd-di-(C1- bis C6-Alkyl)-acetalen, Ortho-ameisen-säure-tri-(C1- bis C6-alkyl) estern, Acetaldehyd-di-(C1- bis C6-alkyl)- acetalen oder Ortho-essigsäuretri-(C1- bis C6-alkyl)-estern (Verbindungen 1)
durch anodische Oxidation von
1,2-Di-(C1- bis C6-alkoxy)-ethan oder -propan, 1,1,2,2-Tetra(C1- bis C6-alkoxy) -ethan oder -propan, oder 2,3-Di-(C1- bis C6-alkoxy)-butan (Verbindungen II)
in Gegenwart eines C1- bis C6-Alkylalkohols (Verbindungen III), wobei man als kathodischen Depolarisator eine übliche organische Verbindung (Verbindung IV) einsetzt, die sich für die elektrochemische Reduktion eignet und wobei man die anodische Oxidation und die kathodische Reduktion in einer ungeteilten Elektrolysezelle in Gegenwart von C1-C6-Alkylalkoholen ausführt. - Verfahren nach Anspruch 1, wobei die Verbindungen I Orthoameisensäuretrimethylester oder Formaldehyddimethylacetal sind, wobei diese Verbindungen auch in Form einer Mischung gebildet werden können.
- Verfahren nach Anspruch 1 oder 2, wobei es sich bei der Verbindung IV um aromatische Kohlenwasserstoffverbindungen, aktivierte Olefine, aromatische Carbonsäuren und deren Derivate, Carbonylverbindungen, Imine, Heterocyclen, Naphthalin oder kernsubstituierte Naphthalinderivate handelt.
- Verfahren nach Anspruch 3, wobei es sich bei der kathodischen Depolarisation um eine der folgenden Umsetzungen handelt:a) Maleinsäure bzw. Derivate der Maleinsäure, bei denen die Säurefunktion in Form von Alkylestern vorliegt zu einem Butantetracarbonsäuretetraalkylester unter Hydrodimerisierungb) von Phthalsäure- oder Phthalsäurederivaten verschiedene Benzolmono-, di-, oder tricarbonsäuren, bzw. Derivate dieser Verbindungen, bei denen die Säurefunktion in Form von Alkylestern vorliegt oder am aromatischen Kern substiuierte Derivate, zu den entsprechenden Mono-, Di- und Triformylbenzolverbindungen,.bei denen die Formylgruppen in Form eines Acetals vorliegtc) Acrylsäure, Acrylsäurealkylester, Acrylamid oder Acrylnitril oder Homologe dieser Verbindungen zu den entsprechenden Hydrodimerisierungsproduktend) Phthalsäure, Phthalsäurealkylester oder am aromatischen Kern substituierte Derivate dieser Verbindungen zu Phthalid bzw. kernsubstituierten Phthalidderivaten, Cyclohexan- oder Cyclohexen-1,2-dicarbonsäure, Cyclohexan- oder Cyclohexen-1;2-dicarbonsäuredialkylestern bzw. entsprechend dem Substitutionsmuster der am aromatischen Kern substituierten Phthalsäurederivate am Cyclohexan- bzw. Cyclohexenring substituierte Derivate.e) Naphthalin oder kernsubstituierte Naphthalinderivate zu 1,2,3,4-Tetrahydronaphthalin bzw. den entsprechenden 1,2,3,4-Tetrahydronaphthalinderivatenf) Pyridin oder kernsubstituierte Pyridinderivate zu 1,4,-Dihydropyridin bzw. den entsprechenden 1,4-Dihydropyridinderivaten.
- Verfahren nach den Ansprüchen 1 bis 4, wobei man das Verfahren in einer Plattenstapelzelle mit seriell geschalteten Stapelelektroden durchführt.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10058304 | 2000-11-24 | ||
DE10058304A DE10058304A1 (de) | 2000-11-24 | 2000-11-24 | Verfahren zur Herstellung von alkoxylierten Carbonylverbindungen durch ein anodisches Oxidationsverfahren unter Nutzung der kathodischen Koppelreaktion zur organischen Synthese |
PCT/EP2001/013587 WO2002042524A2 (de) | 2000-11-24 | 2001-11-22 | Verfahren zur herstellung von alkoxylierten carbonylverbindungen durch ein anodisches oxidationsverfahren unter nutzung der kathodischen koppelreaktion zur organischen synthese |
Publications (2)
Publication Number | Publication Date |
---|---|
EP1348043A2 EP1348043A2 (de) | 2003-10-01 |
EP1348043B1 true EP1348043B1 (de) | 2005-03-09 |
Family
ID=7664478
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP01994702A Expired - Lifetime EP1348043B1 (de) | 2000-11-24 | 2001-11-22 | Verfahren zur herstellung von alkoxylierten carbonylverbindungen durch ein anodisches oxidationsverfahren unter nutzung der kathodischen koppelreaktion zur organischen synthese |
Country Status (11)
Country | Link |
---|---|
US (1) | US6822124B2 (de) |
EP (1) | EP1348043B1 (de) |
JP (1) | JP3906153B2 (de) |
CN (1) | CN1329556C (de) |
AT (1) | ATE290616T1 (de) |
AU (1) | AU2002224874A1 (de) |
CA (1) | CA2429450A1 (de) |
DE (2) | DE10058304A1 (de) |
ES (1) | ES2238501T3 (de) |
NO (1) | NO20032335L (de) |
WO (1) | WO2002042524A2 (de) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2013186094A2 (en) | 2012-06-15 | 2013-12-19 | Basf Se | Anodic oxidation of organic substrates in the presence of nucleophiles |
Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE10146566A1 (de) * | 2001-09-21 | 2003-07-17 | Basf Ag | Verfahren zur Herstellung von Orthocarbonsäuretrialkylestern |
DE10355087A1 (de) * | 2003-11-24 | 2005-06-09 | Basf Ag | Verfahren zur elektrochemischen Herstellung eines kristallinen porösen metallorganischen Gerüstmaterials |
FR2910784B1 (fr) | 2006-12-27 | 2009-02-20 | Arkema France | Utilisation de composes pour la conservation du corps humain ou animal et compositions les comprenant |
DE102007008668A1 (de) * | 2007-02-20 | 2008-08-21 | Tesa Ag | Verfahren zum Beschriften oder Markieren von Oberflächen |
US8889920B2 (en) * | 2010-02-12 | 2014-11-18 | Basf Se | Process for preparing 4-isopropylcyclohexylmethanol |
ES2719585T3 (es) * | 2010-02-12 | 2019-07-11 | Basf Se | Procedimiento para la preparación de 4-isopropilciclohexilmetanol |
CN107473945B (zh) * | 2016-06-08 | 2020-09-01 | 中国科学院大连化学物理研究所 | 一种催化甲醇直接氧化酯化制四甲氧基甲烷的方法 |
CN106591877A (zh) * | 2016-11-14 | 2017-04-26 | 江苏科技大学 | 一种中心原子可变换的偶联剂及其制备方法 |
WO2018097725A1 (en) * | 2016-11-24 | 2018-05-31 | Avantium Knowledge Centre B.V. | Process for treating a furan-2,5-dicarboxylic acid composition |
DE102017113141A1 (de) * | 2017-06-14 | 2018-12-20 | Westfälische Wilhelms-Universität Münster | Elektrolyt für Lithium-Ionen-Batterien |
DE102017012021A1 (de) | 2017-12-22 | 2019-06-27 | Friedrich-Schiller-Universität Jena | Acetalischer Elektrolyt |
JP7105418B2 (ja) * | 2018-02-08 | 2022-07-25 | Eneos株式会社 | シス-二置換非芳香族化合物の製造装置および製造方法 |
CN108677210B (zh) * | 2018-04-17 | 2019-10-29 | 大连理工大学 | 一种酮与羧酸在电化学氢泵反应器中一步加氢酯化的方法 |
CN112195481B (zh) * | 2020-11-02 | 2021-12-10 | 上海漫关越水处理有限公司 | 膜电解合成四甲氧基乙烷的方法 |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3000243A1 (de) | 1980-01-05 | 1981-07-09 | Hoechst Ag, 6230 Frankfurt | Verfahren zur elektrochemischen alkoxylierung von aliphatischen ethern |
US4450055A (en) * | 1983-03-30 | 1984-05-22 | Celanese Corporation | Electrogenerative partial oxidation of organic compounds |
US4648948A (en) * | 1985-05-23 | 1987-03-10 | Meshbesher Thomas M | Electrogenerative oxidation of lower alcohols to useful products |
US5223102A (en) * | 1992-03-03 | 1993-06-29 | E. I. Du Pont De Nemours And Company | Process for the electrooxidation of methanol to formaldehyde and methylal |
DE19618854A1 (de) * | 1996-05-10 | 1997-11-13 | Basf Ag | Verfahren zur Herstellung von Phthaliden |
DE19741423A1 (de) * | 1997-09-19 | 1999-03-25 | Basf Ag | Verfahren zur Herstellung von Phthaliden |
-
2000
- 2000-11-24 DE DE10058304A patent/DE10058304A1/de active Pending
-
2001
- 2001-11-22 AT AT01994702T patent/ATE290616T1/de not_active IP Right Cessation
- 2001-11-22 EP EP01994702A patent/EP1348043B1/de not_active Expired - Lifetime
- 2001-11-22 DE DE50105570T patent/DE50105570D1/de not_active Expired - Fee Related
- 2001-11-22 ES ES01994702T patent/ES2238501T3/es not_active Expired - Lifetime
- 2001-11-22 WO PCT/EP2001/013587 patent/WO2002042524A2/de active IP Right Grant
- 2001-11-22 US US10/432,249 patent/US6822124B2/en not_active Expired - Fee Related
- 2001-11-22 JP JP2002545221A patent/JP3906153B2/ja not_active Expired - Fee Related
- 2001-11-22 CA CA002429450A patent/CA2429450A1/en not_active Abandoned
- 2001-11-22 CN CNB018194397A patent/CN1329556C/zh not_active Expired - Fee Related
- 2001-11-22 AU AU2002224874A patent/AU2002224874A1/en not_active Abandoned
-
2003
- 2003-05-23 NO NO20032335A patent/NO20032335L/no unknown
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2013186094A2 (en) | 2012-06-15 | 2013-12-19 | Basf Se | Anodic oxidation of organic substrates in the presence of nucleophiles |
Also Published As
Publication number | Publication date |
---|---|
NO20032335L (no) | 2003-07-14 |
ATE290616T1 (de) | 2005-03-15 |
DE10058304A1 (de) | 2002-05-29 |
ES2238501T3 (es) | 2005-09-01 |
JP3906153B2 (ja) | 2007-04-18 |
WO2002042524A3 (de) | 2003-03-13 |
EP1348043A2 (de) | 2003-10-01 |
DE50105570D1 (de) | 2005-04-14 |
JP2004514791A (ja) | 2004-05-20 |
CA2429450A1 (en) | 2002-05-30 |
NO20032335D0 (no) | 2003-05-23 |
US20040026263A1 (en) | 2004-02-12 |
CN1476491A (zh) | 2004-02-18 |
AU2002224874A1 (en) | 2002-06-03 |
CN1329556C (zh) | 2007-08-01 |
WO2002042524A2 (de) | 2002-05-30 |
US6822124B2 (en) | 2004-11-23 |
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