Abstract
It is demonstrated that the addition of a non-ionic surfactant (Triton X-100 or Brij L23) to the electrolyte medium leads to a significant improvement to the current efficiency for the methoxylation of N-formylpyrrolidine in a flow electrolysis cell with a horizontal, extended channel length and narrow interelectrode gap (the Ammonite 8). In the presence of Brij L23, the fractional current efficiency is much improved and approaches 1.0 while maintaining a fractional selectivity of 0.99 at a very high conversion in a single pass. The improvement in current efficiency is ascribed to a decrease in the bubble size of the H2 gas evolved at the counter electrode leading to an enhancement in the mass transport regime in the flow stream through the extended channel with millimetre dimensions.
Highlights
There is great interest in using flow electrolysis cells in continuous organic synthesis [1,2]
It is demonstrated that the addition of a non-ionic surfactant (Triton X-100 or Brij L23) to the electrolyte medium leads to a significant improvement to the current efficiency for the methoxylation of N-formylpyrrolidine in a flow electrolysis cell with a horizontal, extended channel length and narrow interelectrode gap
There is no evidence that the presence of a non-ionic surfactant changes the mechanism of the anodic methoxylation of N-formylpyrrolidine
Summary
There is great interest in using flow electrolysis cells in continuous organic synthesis [1,2]. A attractive approach employs a flow cell with a reaction channel with an extended channel length and narrow interelectrode gap so that a very high conversion of reactant to desired product can be achieved in a single pass of the reactant through the cell; cells with productivities of multigrams/h have been described [3,4,5,6,7,8,9]. These cells are presently undivided and it is necessary to consider both anode and cathode reactions. This paper reports a study of the influence of two non-ionic surfactants on the methoxylation of N-formylpyrrolidine in the Ammonite 8 cell [6,7,8]
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