Improved preparative electrochemical oxidation of d-glucose to d-glucaric acid

• Published in: Electrochimica acta Vol. 55; no. 10; pp. 3589 - 3594
• Main Authors: Ibert, Mathias, Fuertès, Patrick, Merbouh, Nabyl, Fiol-Petit, Catherine, Feasson, Christian, Marsais, Francis
• Format: Journal Article
• Language: English
• Published: Kidlington Elsevier Ltd 01.04.2010; Elsevier
• Subjects: Anodes; Cathodes; Chemistry; d-Glucaric acid; d-Glucose; Electrochemical oxidation; Electrochemistry; Exact sciences and technology; Free radicals; General and physical chemistry; Graphite; Kinetics and mechanism of reactions; Scale (corrosion); Stainless steels; TEMPO; Triacid; d-Glucose; Triacid; TEMPO; Electrochemical oxidation; d-Glucaric acid; D-Glucose; Aldose; Sodium Carbonates; Transition metal; D-Glucaric acid; Glucose; Carbon; Aldaric acid; Electrodes; Cyclic voltammetry; Preparative scale; Platinum; Organic free radical; Oxidation; Electrochemical reaction; Organic compounds; Glassy state
• ISSN: 0013-4686; 1873-3859
• DOI: 10.1016/j.electacta.2009.11.041

The 2,2,6,6-tetramethyl-1-piperidinyloxy free radical (TEMPO) mediated electrochemical oxidation of d-glucose to d-glucaric acid on a synthetically useful scale is reported. Using TEMPO and a graphite felt anode combined with a stainless steel cathode, d-glucose was oxidized under different conditions (pH, temperature, co-oxidant), and the reaction outcomes were analyzed. Optimized conditions for such oxidation are provided along with few new interesting results unique to this reaction, such as the appearance of a novel triacid.