GB1258619A - - Google Patents
Info
- Publication number
- GB1258619A GB1258619A GB1258619DA GB1258619A GB 1258619 A GB1258619 A GB 1258619A GB 1258619D A GB1258619D A GB 1258619DA GB 1258619 A GB1258619 A GB 1258619A
- Authority
- GB
- United Kingdom
- Prior art keywords
- liquid
- acrylonitrile
- graphite
- reaction mixture
- adiponitrile
- 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
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
- C25B3/29—Coupling reactions
- C25B3/295—Coupling reactions hydrodimerisation
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)
Abstract
1,258,619. Electrolytic production of adiponitrile. BADISCHE ANILIN & SODA-FABRIK A.G. March 14, 1969 [March 16, 1968; Oct.24, 1968], No.13524/69. Heading C7B. Adiponitrile is produced by electro-chemical hydrodimerization of acrylonitrile in a reaction mixture comprising acrylonitrile, a quaternary ammonium salt, water and if desired an organic solvent for acrylonitrile, at 10-60C. and pH = 1-10; the reaction mixture being passed through a narrow gap between solid electrodes 0À05-2mm. apart, or through the gap obtained between a solid electrode immersed in, but not wetted by, a liquid electrode. The quaternary ammonium salt may a tetramethyl- or tetraethylammonium salt of a mono-alkyl sulphate, sulphate, fluoride, tetrafluoroborate, fluorosulphonate, toluene sulphonate or benzene sulphonate. The organic solvent used may be a lower aliphatic alcohol such as isopropanol, methanol or ethanol; acetonitrile; ethers which are mixible with water, such as tetrahydrofurane, dioxane and glycol monomethyl ether; an amide which may include an alkyl or dialkyl radical, e.g. formamide, diethylacetamide; N- methyl-pyrrolidone; or the end product adiponitrile. A lower aldehyde may also be present and carbon dioxide or boron trifluoride may be added during electrolysis. Various electrodes which may be used include lead; copper; silver; amalgamated lead, copper or silver magnetite; graphite; gold; platinized titanium; platinum foil adhered to graphite; graphite, nickel or titanium coated with lead dioxide; tungsten-nickel alloys or magnetite. As liquid cathode, mercury or galluim above 30C. may be used. Solid electrodes used with a liquid cathode may be of various shapes. Fig.3 illustrates apparatus for carrying out the invention using liquid cathodes. The bottom of the cell body 1 contains circular depressions 4 partly filled with the liquid cathode material. Cylindrical anodes 2, having the edges of their lower faces rounded, are immersed in the liquid cathodes. The reaction mixture is pumped by pump 11 through heatexchanger 12 and enters the cell through nozzle 9 centrally of the anodes so that a thin moving film of electrolyte is maintained between the anodes and their corresponding cathodes. Electrolyte then overflows at 10 and is recirculated.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE1693005A DE1693005C3 (en) | 1968-03-16 | 1968-03-16 | Process for the production of adipic acid dinitrile |
DE19681804809 DE1804809A1 (en) | 1968-03-16 | 1968-10-24 | Process for the production of adipic dinitrile |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1258619A true GB1258619A (en) | 1971-12-30 |
Family
ID=25754577
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB1258619D Expired GB1258619A (en) | 1968-03-16 | 1969-03-14 |
Country Status (10)
Country | Link |
---|---|
US (2) | US3642592A (en) |
AT (1) | AT289750B (en) |
BE (1) | BE729856A (en) |
CH (1) | CH517708A (en) |
DE (2) | DE1693005C3 (en) |
ES (1) | ES364863A1 (en) |
FR (1) | FR2004052A1 (en) |
GB (1) | GB1258619A (en) |
LU (1) | LU58169A1 (en) |
NL (1) | NL6903828A (en) |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3755100A (en) * | 1972-06-09 | 1973-08-28 | Nalco Chemical Co | Method for producing acrylamide from acrylonitrile |
DE2502167C2 (en) * | 1975-01-21 | 1982-09-23 | Basf Ag, 6700 Ludwigshafen | Electrochemical cell with bipolar electrodes |
US4087336A (en) * | 1976-12-27 | 1978-05-02 | Monsanto Company | Electrolytic reductive coupling of hydroxybenzaldehydes |
US4155818A (en) * | 1978-07-17 | 1979-05-22 | Monsanto Company | Semi-continuous electro-hydrodimerization of acrylonitrile to adiponitrile with replating of cathode |
US4472252A (en) * | 1983-03-25 | 1984-09-18 | Ppg Industries, Inc. | Electrolytic synthesis of organic compounds from gaseous reactants |
US4636286A (en) * | 1983-03-25 | 1987-01-13 | Ppg Industries, Inc. | Electro organic method |
US4472251A (en) * | 1983-03-25 | 1984-09-18 | Ppg Industries, Inc. | Electrolytic synthesis of organic compounds from gaseous reactant |
US4462876A (en) * | 1983-03-25 | 1984-07-31 | Ppg Industries, Inc. | Electro organic method and apparatus for carrying out same |
CN113774413A (en) * | 2021-09-30 | 2021-12-10 | 大连理工大学 | Method for preparing adiponitrile by safely and efficiently electrolyzing acrylonitrile in single-phase solution |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3193574A (en) * | 1960-05-08 | 1965-07-06 | Katchalsky Aharon | Process for the preparation of adiponitrile by dimerization of acrylonitrile |
DE1146481B (en) * | 1961-07-17 | 1963-04-04 | Uhde Gmbh Friedrich | Process for the electrolysis of alkali chloride solutions according to the amalgam process using graphite anodes |
NL291762A (en) * | 1962-04-20 | |||
US3193479A (en) * | 1962-08-13 | 1965-07-06 | Monsanto Co | Electrolytic coupling of an olefinic compound with a ketone |
FR1404896A (en) * | 1964-08-12 | 1965-07-02 | Process for electrolysis of solutions and molten salts of electrolytes |
-
1968
- 1968-03-16 DE DE1693005A patent/DE1693005C3/en not_active Expired
- 1968-10-24 DE DE19681804809 patent/DE1804809A1/en active Pending
-
1969
- 1969-03-10 LU LU58169D patent/LU58169A1/xx unknown
- 1969-03-11 CH CH364169A patent/CH517708A/en not_active IP Right Cessation
- 1969-03-12 NL NL6903828A patent/NL6903828A/xx unknown
- 1969-03-13 FR FR6907088A patent/FR2004052A1/fr not_active Withdrawn
- 1969-03-14 GB GB1258619D patent/GB1258619A/en not_active Expired
- 1969-03-14 BE BE729856D patent/BE729856A/xx unknown
- 1969-03-14 AT AT251769A patent/AT289750B/en not_active IP Right Cessation
- 1969-03-15 ES ES364863A patent/ES364863A1/en not_active Expired
- 1969-03-17 US US807895A patent/US3642592A/en not_active Expired - Lifetime
- 1969-03-17 US US807896A patent/US3616320A/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
DE1693005C3 (en) | 1974-12-19 |
ES364863A1 (en) | 1971-01-01 |
US3642592A (en) | 1972-02-15 |
US3616320A (en) | 1971-10-26 |
FR2004052A1 (en) | 1969-11-21 |
CH517708A (en) | 1972-01-15 |
NL6903828A (en) | 1969-09-18 |
DE1693005A1 (en) | 1971-09-02 |
AT289750B (en) | 1971-05-10 |
LU58169A1 (en) | 1969-07-09 |
BE729856A (en) | 1969-09-15 |
DE1804809A1 (en) | 1970-06-04 |
DE1693005B2 (en) | 1974-05-02 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PS | Patent sealed [section 19, patents act 1949] | ||
PLNP | Patent lapsed through nonpayment of renewal fees |