ES341745A1 - Adiponitrile production by the electrolytic hydrodimerization of acrylonitrile - Google Patents
Adiponitrile production by the electrolytic hydrodimerization of acrylonitrileInfo
- Publication number
- ES341745A1 ES341745A1 ES341745A ES341745A ES341745A1 ES 341745 A1 ES341745 A1 ES 341745A1 ES 341745 A ES341745 A ES 341745A ES 341745 A ES341745 A ES 341745A ES 341745 A1 ES341745 A1 ES 341745A1
- Authority
- ES
- Spain
- Prior art keywords
- acrylonitrile
- cathode
- oil phase
- aqueous phase
- emulsion
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Adiponitrile is produced by the electrolytic hydrodimerization of acrylonitrile by employing as catholyte an aqueous emulsion of acrylo. nitrile containing an electrolyte salt, both the aqueous and oil phases of the emulsion contacting the cathode and the aqueous phase containing at least 5% dissolved acrylonitrile while the oil phase contains sufficient acrylonitrile to replace in the aqueous phase the acrylonitrile consumed. Preferably the catholyte also includes an anion polymerization inhibitor, which is defined as a proton donor, a compound which stabilizes the oil phase so as to prevent the cathode being covered solely by the oil phase of the emulsion, or a substance which reduces the negativity of the activated double bond of acrylonitrile and is intended to exclude "free-radical polymerization" inhibitors. Examples of suitable supporting electrolyte salts are alkali and alkaline earth metal, beryllium, magnesium, ammonium and quaternary ammonium salts of inorganic and organic acids including sulphonic and alkylsulphuric acids. Suitable anion polymerization inhibitors are inorganic acids, ammonia, amines, ammonium and amine salts (but not quaternized amine salts), carboxylic or sulphonic acid compounds, alcohols, acetylenic compounds, oxygen, carbon monoxide or dioxide, carbon oxysulphide or disulphide, mercaptans, alkyl disulphides, or protective colloids such as alkyl- or carboxy celluloses, gum tragacanth or proteins. The emulsion may contain diluents such as adiponitrile or propionitrile and may contain organic solvents such as acetonitrile, dioxane, ethanol, ethylene glycol, dimethyl formamide or dimethyl acetamide. Emulsifying agents such as the above-mentioned protective colloids or surfactants such as soaps or synthetic detergents e.g. alkylbenzene sulphonates may be included in a concentration of 10 p.p.m., to 10% by weight. Preferably the weight ratio of the oil phase to the aqueous phase is from 5:1 to 1: 100, the supporting electrolyte is present in the aqueous phase in an amount of 1 to 60% by weight and the anion polymerization inhibitor is present in an amount by weight of 10 p.p.m. to 10% in the aqueous phase and of 0.01 to 10% in the oil phase. Suitably cathode materials are copper, cadmium, tin, lead, mercury or their alloys, the temperature used is in the range 0 to 80 C., the pH is from 1 to 10, and the cathode current density is from 3 to 30 amps./sq. dm. Preferably electrolysis is carried out in a cell divided by a diaphragm of sintered glass, porous sheet material or parchment paper but preferably by a cation exchange resin diaphragm which may be of either the homogeneous or the heterogeneous type and formed from sulphonated divinyl benzene-styrene-butadiene copolymer, the catholyte being circulated through the cathode compartment while a mineral acid, or less desirably an alkyl sulphuric or a sulphonic acid, is circulated through the anode compartment which contains as anode a non-oxidizing material such as platinum, nickel, nickel silicide, Duriron, lead or lead alloy. The diaphragm thickness may be 1 mm. and the diaphragm-electrode spacings may be maintained also at 1 mm. by spacers.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP3798966 | 1966-06-14 | ||
JP3799066 | 1966-06-14 | ||
JP3798866 | 1966-06-14 |
Publications (1)
Publication Number | Publication Date |
---|---|
ES341745A1 true ES341745A1 (en) | 1968-10-16 |
Family
ID=27289663
Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ES341748A Expired ES341748A1 (en) | 1966-06-14 | 1967-06-13 | Adiponitrile production by the electrolytic hydrodimerization of acrylonitrile |
ES341747A Expired ES341747A1 (en) | 1966-06-14 | 1967-06-13 | Adiponitrile production by the electrolytic hydrodimerization of acrylonitrile |
ES341745A Expired ES341745A1 (en) | 1966-06-14 | 1968-06-13 | Adiponitrile production by the electrolytic hydrodimerization of acrylonitrile |
Family Applications Before (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ES341748A Expired ES341748A1 (en) | 1966-06-14 | 1967-06-13 | Adiponitrile production by the electrolytic hydrodimerization of acrylonitrile |
ES341747A Expired ES341747A1 (en) | 1966-06-14 | 1967-06-13 | Adiponitrile production by the electrolytic hydrodimerization of acrylonitrile |
Country Status (10)
Country | Link |
---|---|
US (1) | US3595764A (en) |
BE (3) | BE699928A (en) |
BR (2) | BR6790192D0 (en) |
CH (3) | CH491871A (en) |
DE (2) | DE1618066C3 (en) |
ES (3) | ES341748A1 (en) |
GB (3) | GB1204913A (en) |
LU (3) | LU53854A1 (en) |
NL (3) | NL146795B (en) |
SU (2) | SU374819A3 (en) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NL7006700A (en) * | 1969-05-08 | 1970-11-10 | ||
US3830712A (en) * | 1972-08-28 | 1974-08-20 | Monsanto Co | Process for hydrodimerizing olefinic compounds |
US3898140A (en) * | 1973-08-06 | 1975-08-05 | Monsanto Co | Electrolytic hydrodimerization process improvement |
US3966566A (en) * | 1974-08-15 | 1976-06-29 | Monsanto Company | Electrolytic hydrodimerization process improvement |
-
1967
- 1967-05-31 US US642321A patent/US3595764A/en not_active Expired - Lifetime
- 1967-06-02 DE DE1618066A patent/DE1618066C3/en not_active Expired
- 1967-06-02 DE DE19671618067 patent/DE1618067A1/en active Pending
- 1967-06-06 CH CH796667A patent/CH491871A/en not_active IP Right Cessation
- 1967-06-06 CH CH796467A patent/CH491869A/en not_active IP Right Cessation
- 1967-06-07 BR BR190192/67A patent/BR6790192D0/en unknown
- 1967-06-07 BR BR190191/67A patent/BR6790191D0/en unknown
- 1967-06-08 SU SU1162829A patent/SU374819A3/ru active
- 1967-06-08 CH CH796567A patent/CH491870A/en not_active IP Right Cessation
- 1967-06-08 SU SU1162824A patent/SU379086A3/ru active
- 1967-06-12 LU LU53854D patent/LU53854A1/xx unknown
- 1967-06-12 LU LU53855D patent/LU53855A1/xx unknown
- 1967-06-12 LU LU53861D patent/LU53861A1/xx unknown
- 1967-06-13 ES ES341748A patent/ES341748A1/en not_active Expired
- 1967-06-13 ES ES341747A patent/ES341747A1/en not_active Expired
- 1967-06-14 NL NL676708256A patent/NL146795B/en not_active IP Right Cessation
- 1967-06-14 GB GB27448/67A patent/GB1204913A/en not_active Expired
- 1967-06-14 BE BE699928D patent/BE699928A/xx not_active IP Right Cessation
- 1967-06-14 GB GB27446/67A patent/GB1204911A/en not_active Expired
- 1967-06-14 NL NL6708254A patent/NL6708254A/xx unknown
- 1967-06-14 GB GB27447/67A patent/GB1204912A/en not_active Expired
- 1967-06-14 BE BE699926D patent/BE699926A/xx not_active IP Right Cessation
- 1967-06-14 NL NL676708255A patent/NL146794B/en not_active IP Right Cessation
- 1967-06-14 BE BE699927D patent/BE699927A/xx not_active IP Right Cessation
-
1968
- 1968-06-13 ES ES341745A patent/ES341745A1/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
SU379086A3 (en) | 1973-04-18 |
GB1204911A (en) | 1970-09-09 |
LU53855A1 (en) | 1967-08-14 |
GB1204913A (en) | 1970-09-09 |
DE1618066A1 (en) | 1971-04-01 |
NL6708254A (en) | 1967-12-15 |
BE699928A (en) | 1967-12-14 |
NL146795B (en) | 1975-08-15 |
BR6790191D0 (en) | 1973-05-17 |
BE699927A (en) | 1967-12-14 |
DE1618066C3 (en) | 1974-11-07 |
BR6790192D0 (en) | 1973-05-10 |
CH491871A (en) | 1970-06-15 |
NL146794B (en) | 1975-08-15 |
NL6708255A (en) | 1967-12-15 |
CH491869A (en) | 1970-06-15 |
GB1204912A (en) | 1970-09-09 |
DE1618068A1 (en) | 1970-10-22 |
DE1618068B2 (en) | 1975-09-18 |
DE1618067A1 (en) | 1970-09-24 |
LU53861A1 (en) | 1967-08-14 |
CH491870A (en) | 1970-06-15 |
ES341747A1 (en) | 1968-07-01 |
DE1618066B2 (en) | 1974-03-21 |
LU53854A1 (en) | 1967-08-14 |
ES341748A1 (en) | 1968-07-01 |
NL6708256A (en) | 1967-12-15 |
BE699926A (en) | 1967-12-14 |
SU374819A3 (en) | 1973-03-20 |
US3595764A (en) | 1971-07-27 |
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