EP1348043A2 - 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 syntheseInfo
- Publication number
- EP1348043A2 EP1348043A2 EP01994702A EP01994702A EP1348043A2 EP 1348043 A2 EP1348043 A2 EP 1348043A2 EP 01994702 A EP01994702 A EP 01994702A EP 01994702 A EP01994702 A EP 01994702A EP 1348043 A2 EP1348043 A2 EP 1348043A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- compounds
- derivatives
- alkyl
- acid
- substituted
- 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.)
- Granted
Links
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
Definitions
- the present invention relates to a process for the preparation of alkoxylated carbonyl compounds (compounds I) of the general formula I
- R ⁇ R 2 is hydrogen or Ci to Cökkyl
- R 3 independently of one another C ⁇ ⁇ C to ß alkyl a is 0 or 1 b is 2 or 3
- R 4 , R 5 , R 6 , R 7 are hydrogen or C 1 -C 6 -alkyl
- R 5, R 6 Ci to Cg alkyl or Ci to C alkoxy ß mean in the presence of a C ⁇ ⁇ to C ⁇ 6 alkyl alcohol (compounds III)
- a conventional organic compound (compounds IV) is used as the cathodic depolarizer, which is suitable for the electrochemical reduction, and the anodic oxidation and the cathodic reduction are carried out in an undivided electrolysis cell in the presence of Ci-C ⁇ -alkyl alcohols.
- formaldehyde dimethyl acetal, trimethyl ortho-formate, acetaldehyde dimethyl acetal or trimethyl orthoacetate can be prepared from the corresponding compounds II and methanol in a particularly simple manner.
- preferred compounds I and II are those in which R 4 has the same meaning as R 7 or R 5 has the same meaning as R 6 by the number of to keep the compounds contained in the reaction mixture to be worked up as small as possible.
- such alcohols are employed whose alkyl radicals have the same meaning as the radicals R 8, R 9, or the alkyl radicals in R 5, R 6, provided that R 5, R 6 C ⁇ to C ß alkoxy.
- Suitable cathodic depolisators are conventional organic compounds which are suitable for anodic reduction, such as aromatic hydrocarbon compounds, activated olefins, carbonyl compounds, aromatic carboxylic acids and their derivatives, and also naphthalene or nucleus-substituted naphthalene derivatives.
- the process according to the invention is particularly suitable for producing the following compounds or classes of compounds:
- X is an alkoxycarbonyl, nitrile or carbamide group and R 10 is Ci to C 6 alkyl.
- phthalic acid phthalic acid alkyl esters or derivatives substituted on the aromatic nucleus of these compounds to give phthalide or nucleus-substituted phthalide derivatives, cyclohexane or cyclohexane-1, 2-dicarboxylic acid or cyclohexane or cyclohexene-1, 2-dicarboxylic acid dialkyl esters or according to the substitution pattern the phthalic acid derivatives substituted on the aromatic nucleus on the cyclohexane or cyclohexene ring substituted derivatives.
- naphthalene or nucleus-substituted naphthalene derivatives to 1,2,3,4-tetrahydronaphthalene or the corresponding 1,2,3,4-tetrahydronaphthalene derivatives
- Suitable substituents with which the aromatic nuclei in the abovementioned starting compounds can be substituted are inert, difficult-to-reduce groups such as C 1 -C 1 -alkyl, C 1 -C 6 -alkoxy or halogen.
- Phthalide itself concerns it is particularly those compounds as described in DE-A-19618854.
- the particularly suitable output connections are also detailed there.
- the molar ratio of the starting compounds for the cathode and anode reactions and the products formed in these reactions in electrolytes to one another is not critical.
- the molar ratio of the sum of the compounds I and II to the alcohols (compounds IV) is chosen from 0.1: 1 to 5: 1, preferably 0.2: 1 to 2: 1 and particularly preferably 0.3: 1 to 1: 1.
- the conductive salts contained in the electrolysis solution are generally alkali, tetra- (C 1 -C 6 -alkyl) -ammonium or tri- (C ⁇ -C ⁇ - alkyl) -benzylammonium salts.
- Sulfate, hydrogen sulfate, alkyl sulfates, alkyl sulfonates, halides, phosphates, carbonates, alkyl phosphates, alkyl carbonates, nitrate, alcoholates, tetrafluoroborate or perchlorate are suitable as counterions.
- acids derived from the above-mentioned anions can be considered as conductive salts.
- Methyltributylammonium methyl sulfate MTBS
- methyltriethylammonium methyl sulfate methyl tripropylmethylammonium methyl sulfate are preferred.
- customary cosolvents are added to the electrolysis solution. These are the inert solvents with a high oxidation potential that are common in organic chemistry. Examples include dimethyl carbonate or propylene carbonate.
- the process according to the invention can be carried out in all customary undivided types of electrolysis cells.
- One preferably works continuously with undivided flow cells.
- Plate stack cells with series-shaped stack electrodes, as described for example in DE-A-19533773, are particularly suitable.
- 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, normal pressure is used. Higher pressures are preferably used if at higher temperatures structures should be worked to avoid boiling of the starting compounds or cosolvents.
- noble metals such as platinum or metal oxides such as ruthenium or chromium oxide or mixed oxides of the Ruo x Tio x type are suitable as anode materials.
- Graphite or carbon electrodes are preferred.
- cathode materials are iron, steel, stainless steel, nickel or precious metals such as platinum and graphite or carbon materials.
- the system is preferably graphite as anode and cathode and graphite as anode and nickel, stainless steel or steel as cathode.
- the electrolyte solution is worked up using general separation methods.
- the electrolysis solution is generally first distilled and the individual compounds are obtained separately in the form of different fractions. Further purification can be carried out, for example, by crystallization, distillation or by chromatography.
- annular disk electrodes each with an area of 140 cm 2 and an outer diameter of 14 cm, are arranged so that they form a stack.
- the disks are set to a distance of 1 mm using spacers, thus creating 10 gaps between the ring disks.
- the electrode material is graphite.
- the inner 0.5 cm thick disks are switched bipolar under electrolysis conditions.
- the top electrode is anodically contacted by means of a graphite stamp and a cover disk, the bottom electrode is contacted cathodically, the cathodic contact runs over the base plate of the cell.
- the electrolyte flows through the central hole in the base plate into the cell, spreads over the gaps and leaves the cell above the top electrode.
- the cell is part of a circulation apparatus in which the electrolyte is pumped around, heated or cooled.
- 975 g of tetramethoxyethane, 936 g of dimethyl maleate, 170 g of a 60% methanolic solution of methyltributylammonium methyl sulfate and 419 g of methanol were electrolyzed at a current of 3 A, the current strength decreased to 2.5 A during the electrolysis, the voltage per gap rose from 5 V to 6 V, electrolysis was continued until 95% of the dimethyl maleate had been converted.
- the electrolysis discharge contained 24.4% methyl butanetetracarboxylic acid, 14.2% trimethyl orthoformate, 25.6% tetramethoxyethane and 1.7% dimethyl maleate.
- the selectivity of the ortho ester formation was 82%.
- the composition of the electrolysis discharge was determined using a gas chromatograph and is shown in% by area (GC area%).
- a cell according to Example 1 was used, the number of columns was 7.
- a cell according to Example 2 was used.
- the cell and the cell circuit are constructed analogously to example 1, 11 electrodes with a diameter of 65 mm and an area of 31.6 cm 2 form 10 gaps.
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)
Description
Claims
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
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 |
DE10058304 | 2000-11-24 | ||
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 true EP1348043A2 (de) | 2003-10-01 |
EP1348043B1 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) |
Families Citing this family (15)
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 |
ES2719585T3 (es) * | 2010-02-12 | 2019-07-11 | Basf Se | Procedimiento para la preparación de 4-isopropilciclohexilmetanol |
US8889920B2 (en) * | 2010-02-12 | 2014-11-18 | Basf Se | Process for preparing 4-isopropylcyclohexylmethanol |
EP2861785A2 (de) | 2012-06-15 | 2015-04-22 | Basf Se | Anodische oxidation organischer substrate in gegenwart von nukleophilen |
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 |
EP3545121B1 (de) * | 2016-11-24 | 2021-06-09 | Avantium Knowledge Centre B.v. | Verfahren zur behandlung einer dicarbonsäurezusammensetzung |
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 US US10/432,249 patent/US6822124B2/en not_active Expired - Fee Related
- 2001-11-22 WO PCT/EP2001/013587 patent/WO2002042524A2/de active IP Right Grant
- 2001-11-22 CA CA002429450A patent/CA2429450A1/en not_active Abandoned
- 2001-11-22 ES ES01994702T patent/ES2238501T3/es not_active Expired - Lifetime
- 2001-11-22 JP JP2002545221A patent/JP3906153B2/ja not_active Expired - Fee Related
- 2001-11-22 AU AU2002224874A patent/AU2002224874A1/en not_active Abandoned
- 2001-11-22 EP EP01994702A patent/EP1348043B1/de not_active Expired - Lifetime
- 2001-11-22 CN CNB018194397A patent/CN1329556C/zh not_active Expired - Fee Related
- 2001-11-22 AT AT01994702T patent/ATE290616T1/de not_active IP Right Cessation
- 2001-11-22 DE DE50105570T patent/DE50105570D1/de not_active Expired - Fee Related
-
2003
- 2003-05-23 NO NO20032335A patent/NO20032335L/no unknown
Non-Patent Citations (1)
Title |
---|
See references of WO0242524A2 * |
Also Published As
Publication number | Publication date |
---|---|
CN1476491A (zh) | 2004-02-18 |
CA2429450A1 (en) | 2002-05-30 |
DE10058304A1 (de) | 2002-05-29 |
NO20032335L (no) | 2003-07-14 |
AU2002224874A1 (en) | 2002-06-03 |
US20040026263A1 (en) | 2004-02-12 |
ATE290616T1 (de) | 2005-03-15 |
CN1329556C (zh) | 2007-08-01 |
JP3906153B2 (ja) | 2007-04-18 |
NO20032335D0 (no) | 2003-05-23 |
EP1348043B1 (de) | 2005-03-09 |
WO2002042524A3 (de) | 2003-03-13 |
US6822124B2 (en) | 2004-11-23 |
JP2004514791A (ja) | 2004-05-20 |
WO2002042524A2 (de) | 2002-05-30 |
DE50105570D1 (de) | 2005-04-14 |
ES2238501T3 (es) | 2005-09-01 |
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