EP0902846A1 - Process for preparing phthalides - Google Patents
Process for preparing phthalidesInfo
- Publication number
- EP0902846A1 EP0902846A1 EP97921810A EP97921810A EP0902846A1 EP 0902846 A1 EP0902846 A1 EP 0902846A1 EP 97921810 A EP97921810 A EP 97921810A EP 97921810 A EP97921810 A EP 97921810A EP 0902846 A1 EP0902846 A1 EP 0902846A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- phthalic acid
- alkyl
- phthalides
- hydrogen
- anodic
- 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
- C25B3/20—Processes
- C25B3/25—Reduction
Definitions
- a disadvantage of the described methods is the expenditure on equipment associated with the use of divided electrolysis cells, since in this case 2 cell circles are required.
- working with 2 cell circles is associated with the following further disadvantages:
- the cell circles must be separated by a membrane or a diaphragm; this means a loss of energy through ohmic heat.
- at least one chamber is usually charged with an aqueous (> 80% H 2 O) conductive salt solution.
- an aqueous (> 80% H 2 O) conductive salt solution In the case of cathodic reductions, this is the anolyte.
- the compulsion to do so severely limits the scope for using the anode reaction. Normally only hydrogen is produced as the anode product. Furthermore, there is a risk with the known methods that anode corrosion and poisoning of the cathodes occur.
- the technical problem underlying the invention was therefore to provide a technically simpler process for the production of phthalides in high purity and good yields, which does not have the disadvantages of the prior art and in particular the possibility of using the Anode reaction opened to produce products other than hydrogen.
- R 1 , R 2 , R 3 and R 4 independently of one another hydrogen, C ⁇ ⁇ bis
- R 5 and R 6 a) independently of one another -COOH or COOX, where X is Ci to C 4 alkyl,
- R 5 and R 6 together -CO-O-CO-.
- Particularly preferred are the derivatives of phthalic acid in which R 1, R 2, R 3 and R 4 are hydrogen and in particular the phthalic acid di (Ci to C 3 alkyl) esters, especially the dimethyl phthalate. 5
- Electrodes made of graphite or carbon are particularly suitable as electrode materials (both cathode and anode).
- the electrolyte is usually a 2 to 15 40% strength by weight solution of phthalic acid or a phthalic acid derivative in an organic solvent which preferably contains less than 25, particularly preferably less than 5% by weight of water.
- Suitable organic solvents are, in particular, 0 aliphatic C ⁇ to Ca alcohols, in particular methanol or ethanol, or a mixture of such alcohols with a carboxamide such as dimethylformamide or t-butylformamide.
- the electrolytes generally contain alkyl sulfates, for example methyl sulfate, or quaternary ammonium salts, in particular tetra (Ci to C 4 alkyl) ammonium halogens or tetrafluoroborates, usually in amounts of 0.4 to 10 wt. -% based on the electrolyte.
- alkyl sulfates for example methyl sulfate
- quaternary ammonium salts in particular tetra (Ci to C 4 alkyl) ammonium halogens or tetrafluoroborates, usually in amounts of 0.4 to 10 wt. -% based on the electrolyte.
- anodic coupling process it is advisable to use conventional organic compounds as anodic depolarizer, the suitability of which is generally known to the person skilled in the art for the electrochemical oxidation.
- Some of the anodic coupling processes are preferably carried out in the presence of a mediator. Possible 5 anodic coupling processes and their mediatization are described, for example, in D. Kyriakou, Modern Electroorganic Chemistry, Springer, Berlin 1994, in Chapter 4.2.
- Halogen compounds especially bromides or iodides, are particularly suitable as mediators.
- the other process parameters such as temperature and current density are concerned, these are not critical as long as they are within the normal range for electrochemical conversion of organic compounds. They are specified, for example, in DE-A-2 510 920.
- an electrolysis cell consisting of ten bipolar switched ring disks made of graphite, area per side: 147 dm 2 , with an electrode spacing of 0.7 mm, a solution of 500 g dimethyl phthalate (2.56 mol), 1600 g t. -Butylformamide and 375 g of methanol with 25 g of tetrabutylammonium tetrafluoroborate at a current of 2.5 A for 11.5 h at 60 ° C electrolyzed.
Abstract
Description
Claims
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19618854A DE19618854A1 (en) | 1996-05-10 | 1996-05-10 | Process for the production of phthalides |
DE19618854 | 1996-05-10 | ||
PCT/EP1997/002185 WO1997043464A1 (en) | 1996-05-10 | 1997-04-28 | Process for preparing phthalides |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0902846A1 true EP0902846A1 (en) | 1999-03-24 |
EP0902846B1 EP0902846B1 (en) | 2000-07-26 |
Family
ID=7793943
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP97921810A Expired - Lifetime EP0902846B1 (en) | 1996-05-10 | 1997-04-28 | Process for preparing phthalides |
Country Status (8)
Country | Link |
---|---|
US (1) | US6063256A (en) |
EP (1) | EP0902846B1 (en) |
JP (1) | JP3946260B2 (en) |
CN (1) | CN1058302C (en) |
CA (1) | CA2254788C (en) |
DE (2) | DE19618854A1 (en) |
ES (1) | ES2150770T3 (en) |
WO (1) | WO1997043464A1 (en) |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AR018507A1 (en) * | 1997-09-19 | 2001-11-28 | Basf Se | RECOVERY PROCESS OF A COMPOUND DERIVED FROM THE PHTALIC ACID OF A REACTION MIXTURE IN WHICH THIS COMPOUND IS SYNTHESIZED |
DE19741423A1 (en) * | 1997-09-19 | 1999-03-25 | Basf Ag | Pure phthalide or derivative preparation in high yield |
DE19808296A1 (en) * | 1998-02-27 | 1999-09-02 | Basf Ag | Process for the selective hydrolysis of acetals or ketals in the presence of phthalides |
DE19944989A1 (en) | 1999-09-20 | 2001-03-22 | Basf Ag | Process for the electrolytic conversion of furan derivatives |
DE19944990A1 (en) | 1999-09-20 | 2001-03-22 | Basf Ag | Process for the electrolytic conversion of organic compounds |
CN1182127C (en) * | 2000-06-28 | 2004-12-29 | 中国医学科学院药物研究所 | Substituted 2-benzo [c] furanone compound, its preparing process and medicinal composition containing it |
DE10057888A1 (en) * | 2000-11-22 | 2002-05-23 | Basf Ag | Production of butanetetracarboxylic acid derivatives useful as intermediates for e.g. plant protectants, dyes, complexing agents, polymers by cathodic reduction of maleate or fumarate esters and producing co-product at anode |
DE10058304A1 (en) * | 2000-11-24 | 2002-05-29 | Basf Ag | Process for the preparation of alkoxylated carbonyl compounds by an anodic oxidation process using the cathodic coupling reaction for organic synthesis |
CA2876566A1 (en) * | 2012-06-15 | 2013-12-19 | Basf Se | Anodic oxidation of organic substrates in the presence of nucleophiles |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2510920A1 (en) * | 1975-03-13 | 1976-09-30 | Basf Ag | Electrochemical prepn of phthalide - from phthalic acid or anhydride, with final acidificn at controlled temp |
DE2630927A1 (en) * | 1976-07-09 | 1978-01-19 | Basf Ag | METHOD FOR PRODUCING PHTHALIDOCARBONIC ACID- (5) |
-
1996
- 1996-05-10 DE DE19618854A patent/DE19618854A1/en not_active Withdrawn
-
1997
- 1997-04-28 ES ES97921810T patent/ES2150770T3/en not_active Expired - Lifetime
- 1997-04-28 JP JP54044397A patent/JP3946260B2/en not_active Expired - Fee Related
- 1997-04-28 CA CA002254788A patent/CA2254788C/en not_active Expired - Fee Related
- 1997-04-28 DE DE59702087T patent/DE59702087D1/en not_active Expired - Fee Related
- 1997-04-28 US US09/125,019 patent/US6063256A/en not_active Expired - Fee Related
- 1997-04-28 WO PCT/EP1997/002185 patent/WO1997043464A1/en active IP Right Grant
- 1997-04-28 CN CN97192040A patent/CN1058302C/en not_active Expired - Fee Related
- 1997-04-28 EP EP97921810A patent/EP0902846B1/en not_active Expired - Lifetime
Non-Patent Citations (1)
Title |
---|
See references of WO9743464A1 * |
Also Published As
Publication number | Publication date |
---|---|
CA2254788C (en) | 2005-03-01 |
JP3946260B2 (en) | 2007-07-18 |
WO1997043464A1 (en) | 1997-11-20 |
DE59702087D1 (en) | 2000-08-31 |
CA2254788A1 (en) | 1997-11-20 |
DE19618854A1 (en) | 1997-11-13 |
US6063256A (en) | 2000-05-16 |
EP0902846B1 (en) | 2000-07-26 |
JP2000511592A (en) | 2000-09-05 |
ES2150770T3 (en) | 2000-12-01 |
CN1210564A (en) | 1999-03-10 |
CN1058302C (en) | 2000-11-08 |
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