Electrocatalytic hydrogenation of acetophenone using a Polymer Electrolyte Membrane Electrochemical Reactor

Abstract

Please cite this article as: A. Sáez, V. García-García, J. Solla-Gullón, A. Aldaz, V. Montiel, Electrocatalytic hydrogenation of acetophenone using a Polymer Electrolyte Membrane Electrochemical Reactor, Electrochimica Acta (2010Acta ( ), doi:10.1016Acta ( /j.electacta.2012 This is a PDF file of an unedited manuscript that has been accepted for publication. As a service to our customers we are providing this early version of the manuscript. The manuscript will undergo copyediting, typesetting, and review of the resulting proof before it is published in its final form. Please note that during the production process errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain.Page 1 of 20 A c c e p t e d M a n u s c r i p t 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 61 62 63 AbstractThe use of a solid polymeric electrolyte, spe, is not commonly found in organic electrosynthesis despite its inherent advantages such as the possible elimination of the electrolyte entailing simpler purification processes, a smaller sized reactor and lower energetic costs. In order to test if it were possible to use a spe in industrial organic electrosynthesis, we studied the synthesis of 1-phenylethanol through the electrochemical hydrogenation of acetophenone using Pd/C 30% wt with different loadings as cathode and a hydrogen gas diffusion anode. A Polymer ElectrolyteMembrane Electrochemical Reactor, PEMER, with a fuel cell structure was chosen to carry out electrochemical reduction with a view to simplifying an industrial scale-up of the electrochemical process. We studied the influence of current density and cathode catalyst loading on this electroorganic synthesis. Selectivity for 1-phenylethanol was around 90% with only ethylbenzene and hydrogen detected as by-products.

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

“…Preparative electrooxidation of PGA was performed using PEMER configuration with a commercial flow distributor based on two graphite plates [7]. The graphite plates For the electrolysis experiments, PGA conversion and the formation of the final products were followed by HPLC, according to the experimental procedure described elsewhere [24].…”

“…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.…”

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

“…The catalytic ink was made by dispersing a homemade Pd/C 30 wt% catalyst in isopropanol and Nafion solution 5 wt% as previously described [1]. The Pd catalytic loading and Pd/C/Nafion ratio were 0.…”

“…Acetophenone is used for the synthesis of 1-phenylethanol, an attractive product for fine chemical, pharmaceutical and cosmetic industries. In a previous paper [1], we studied the electrochemical hydrogenation of acetophenone yielding 1-phenylethanol as main product and ethylbenzene and hydrogen as by-products.…”

High Performance of Alkaline Anion-Exchange Membranes Based on Chitosan/Poly (vinyl) Alcohol Doped with Graphene Oxide for the Electrooxidation of Primary Alcohols

“…Nowadays, membranes are a key component in energy conversion and storage [1], and more recently, in the less well-known field of organic electrosynthesis [2][3][4][5]. In this regard, Polymer Electrolyte Membrane Electrochemical Reactor (PEMER) configuration based on ion-exchange Polymer Electrolyte Membrane (PEM) and Direct Alcohol Fuel Cells (DAFCs) has been employed for the electrooxidation of an unsaturated alcohol to its corresponding carboxylic acids in alkaline medium [6].…”