GB1111413A - Making adiponitrile and like compounds by reductive dimerisation - Google Patents

Making adiponitrile and like compounds by reductive dimerisation

Info

Publication number
GB1111413A
GB1111413A GB49714/64A GB4971464A GB1111413A GB 1111413 A GB1111413 A GB 1111413A GB 49714/64 A GB49714/64 A GB 49714/64A GB 4971464 A GB4971464 A GB 4971464A GB 1111413 A GB1111413 A GB 1111413A
Authority
GB
United Kingdom
Prior art keywords
phosphate
anolyte
mercury
acrylonitrile
cationic agent
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
Application number
GB49714/64A
Inventor
Dennis Pemberton
John Henry Edgar Marsden
Frank Stanley Holland
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to GB49714/64A priority Critical patent/GB1111413A/en
Priority to NL6515603A priority patent/NL6515603A/xx
Priority to US511210A priority patent/US3496216A/en
Priority to CH1662365A priority patent/CH456564A/en
Priority to CH1671865A priority patent/CH475948A/en
Priority to NL6515816A priority patent/NL6515816A/xx
Priority to BE673406A priority patent/BE673406A/xx
Priority to DE19651543098 priority patent/DE1543098A1/en
Priority to FR41204A priority patent/FR1456388A/en
Priority to BE673404A priority patent/BE673404A/xx
Priority to FR41288A priority patent/FR1456402A/en
Publication of GB1111413A publication Critical patent/GB1111413A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • 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
    • C—CHEMISTRY; METALLURGY
    • C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
    • C25C—PROCESSES FOR THE ELECTROLYTIC PRODUCTION, RECOVERY OR REFINING OF METALS; APPARATUS THEREFOR
    • C25C1/00—Electrolytic production, recovery or refining of metals by electrolysis of solutions

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Electrochemistry (AREA)
  • Materials Engineering (AREA)
  • Metallurgy (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)
  • Hydrogenated Pyridines (AREA)

Abstract

Unsaturated a , b -nitriles e.g. acrylonitrile is hydrodimerized to form adiponitrile in the presence mercury/alkali metal amalgam, electrolytically using an alkali solution containing acrylonitrile and an organic cationic agent, and preferably maintaining pH in the range 6 to 11 by adding alkali salts of poly-basic acids e.g. sodium borate, phosphate, or carbonate. The cationic agent may be a quaternary ammonium or phosphonium salt or base or a tertiary sulphonium compound e.g. tetraethyl-ammonium-p-toluene sulphonate, tetraethyl ammonium iodide or phosphate, or cetyl trimethyl ammonium bromide. In examples, an apparatus as described in Specification 1,076,783 is used in which a cylindrical vessel closed at the base by a glass fibre screw and containing a mercury layer is immersed in the alkaline electrolyte which contains acrylonitrile, or methacrylonitrile, and the cationic agent. A platinum wire cathode dips into the mercury, and a nickel strip in the alkaline anolyte as anode. A phosphate was added to bring pH to 7, and Co2 is bubbled through the anolyte. Temperature is maintained at 25 DEG to 35 DEG C. and a current of 10 amps is applied. After 30 mins., the adiponitrile extracted from the anolyte by distillation, solvent extraction &c. provided a 65% yield. Reference is made to reducing the product to hexamethylene diamine, forming the adipate and condensing to the polymer, all chemical processes.
GB49714/64A 1964-12-07 1964-12-07 Making adiponitrile and like compounds by reductive dimerisation Expired GB1111413A (en)

Priority Applications (11)

Application Number Priority Date Filing Date Title
GB49714/64A GB1111413A (en) 1964-12-07 1964-12-07 Making adiponitrile and like compounds by reductive dimerisation
NL6515603A NL6515603A (en) 1964-12-07 1965-12-01
US511210A US3496216A (en) 1964-12-07 1965-12-02 Reductive dimerization of alpha,beta-unsaturated nitriles by means of amalgam
CH1662365A CH456564A (en) 1964-12-07 1965-12-02 Process for the reductive dimerization of a, B-unsaturated nitriles
CH1671865A CH475948A (en) 1964-12-07 1965-12-03 Process for the reductive dimerization of amides which are olefinically unsaturated in the a, B-position
NL6515816A NL6515816A (en) 1964-12-07 1965-12-06
BE673406A BE673406A (en) 1964-12-07 1965-12-07
DE19651543098 DE1543098A1 (en) 1964-12-07 1965-12-07 Process for the reductive dimerization of alpha, beta-olefinic compounds
FR41204A FR1456388A (en) 1964-12-07 1965-12-07 Process for the reductive dimerization of alpha, beta-olefinic esters and amides
BE673404A BE673404A (en) 1964-12-07 1965-12-07
FR41288A FR1456402A (en) 1964-12-07 1965-12-07 Process for the reductive dimerization of alpha, beta unsaturated nitriles

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB49714/64A GB1111413A (en) 1964-12-07 1964-12-07 Making adiponitrile and like compounds by reductive dimerisation

Publications (1)

Publication Number Publication Date
GB1111413A true GB1111413A (en) 1968-04-24

Family

ID=10453289

Family Applications (1)

Application Number Title Priority Date Filing Date
GB49714/64A Expired GB1111413A (en) 1964-12-07 1964-12-07 Making adiponitrile and like compounds by reductive dimerisation

Country Status (6)

Country Link
US (1) US3496216A (en)
BE (1) BE673404A (en)
CH (1) CH456564A (en)
FR (1) FR1456402A (en)
GB (1) GB1111413A (en)
NL (1) NL6515603A (en)

Family Cites Families (2)

* Cited by examiner, † Cited by third party
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
GB1157441A (en) * 1964-06-02 1969-07-09 Ici Ltd Reductive Dimerisation of Unsaturated Nitriles

Also Published As

Publication number Publication date
FR1456402A (en) 1966-10-21
US3496216A (en) 1970-02-17
CH456564A (en) 1968-07-31
NL6515603A (en) 1966-06-08
BE673404A (en) 1966-06-07

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