Acetonitrile → Dimethyl sebacate

Participants

Reaction Steps

In operation of the cell, anolyte was pumped by means of a syringe pump to the anolyte channel and through the porous anode and catholyte was pumped by means of another syringe pump to the cathode cavity of the cell and through the porous cathode. The anolyte consisted of a 0.1 M solution of tetramethyl ammonium monomethyl adipate ##STR5## in a solution composed of 90% by volume of acetonitrile and 10% by volume of water. The catholyte consisted of a 0.1 M solution of the same amine as above in a solution of 90% by volume of acetonitrile and 10% by volume of water to which solution was added 10% by volume of ethyl acrylate. Both anolyte and catholyte were caused to flow through their respective electrodes at the rate of 6 milliliters (mls) per minute. In carrying out the electrolytic reaction 1 Ampere of current was supplied to the anode--providing 0.2 A/geometric cm2. At the start of and during the course of the electrolytic reaction a solvent-electrolyte consisting of the above amine in 9cetonitrile and water solution was pumped upward through the channel between the anode and cathode at the rate of 20 mls/min., thus effectively preventing the anolyte from contacting the cathode and the catholyte from contacting the anode. The liquid exiting from the cell was collected and analyzed, and it was found that an 87% yield of dimethyl sebacate (from the monomethyl adipate) was obtained at 35% current efficiency. Also, an 84% yield of diethyl adipate (from the ethyl acrylate) was obtained at 61% current efficiency. No radical adducts were noted in the effluent from the cell.

Provenance & Evidence