Electrochemical synthesis at pre-pilot scale of 1-phenylethanol by cathodic reduction of acetophenone using a solid polymer electrolyte

Abstract

The pre-pilot scale synthesis of 1-phenylethanol was carried out by the cathodic hydrogenation of acetophenone in a 100 cm 2 (geometric area) Polymer Electrolyte Membrane Electrochemical Reactor. The cathode was a Pd/C electrode. Hydrogen oxidation on a gas diffusion electrode was chosen as anodic reaction in order to take advantage of the hydrogen evolved during the reduction. This hydrogen oxidation provides the protons needed for the synthesis. The synthesis performed with only a solid polymer electrolyte, spe, has lower fractional conversion although a higher selectivity than that carried out using a support-electrolyte-solvent together with a spe. However, the difference between these two cases is rather small and since the work-up and purification of the final product are much easier when only a spe is used, this last process was chosen for the pre-pilot electrochemical synthesis of 1-phenylethanol.

Performance Assessment of a Polymer Electrolyte Membrane Electrochemical Reactor Under Alkaline Conditions − a Case Study With the Electrooxidation of Alcohols

“…In this regard, the concept of Polymer Electrolyte Membrane Electrochemical Reactor (PEMER) has been recently introduced in organic electrosynthesis, e.g. for the N-acetyl-L-cysteine production from the electroreduction of N,N-diacetyl-L-cysteine [5] and the synthesis of 1-phenylethanol from the electroreduction of acetophenone [6,7] under acidic conditions. Moreover, pioneering work performed by Ogumi and co-workers on the electrochemical hydrogenation of olefinic double bonds [8] and the reduction of nitrobenzene [9] was performed using a Nafion membrane-based SPE, within a similar configuration to PEMER, in which the product purification operations were then reduced.…”

Developing electrochemical hydrogenation towards industrial application

“…The vast majority of hydrogenation catalysts consists of metals that are either known to catalyse thermal hydrogenations such as palladium, 32,33,37,42,81,82,84,112,195,196 ruthenium, 32,88,118,191,[197][198][199][200][201] and nickel 33,108,178,199,[202][203][204][205][206][207][208][209] or known to easily form active hydrogen species on their surface under reductive conditions like platinum. 21,22,24,48,122,134,136,152,165,182,[210][211][212][213][214][215] The other frequently reported catalyst is copper, which is mainly applied for the hydrogenation of furfural derivatives…”

Electrosynthesis of 2,3-butanediol and methyl ethyl ketone from acetoin in flow cells

“…Electrolyte Membrane Electrochemical Reactor based on the design of direct organic fuel cells, as shown by Sáez et al for the electroreduction of acetophenone to 1-phenylethanol. 3…”