2-Methoxyhydroquinone from Vanillin for Aqueous Redox-Flow Batteries

Werner Schlemmer; Philipp Nothdurft; Alina Petzold; Gisbert Riess; Philipp Frühwirt; Max Schmallegger; Georg Gescheidt-Demner; Roland Fischer; Stefan A Freunberger; Wolfgang Kern; Stefan Spirk

doi:10.1002/anie.202008253

2-Methoxyhydroquinone from Vanillin for Aqueous Redox-Flow Batteries

Angew Chem Int Ed Engl. 2020 Dec 14;59(51):22943-22946. doi: 10.1002/anie.202008253. Epub 2020 Oct 8.

Affiliations

¹ Institute of Bioproducts and Paper Technology, Graz University of Technology, Inffeldgasse 23, 8010, Graz, Austria.
² Chair in Chemistry of Polymeric Materials, Montanuniversitaet Leoben, Otto-Glöckel-Strasse 2, 8700, Leoben, Austria.
³ Institute of Physical and Theoretical Chemistry, Graz University of Technology, Stremayrgasse 9, 8010, Graz, Austria.
⁴ Institute of Inorganic Chemistry, Graz University of Technology, Stremayrgasse 9, 8010, Graz, Austria.
⁵ Institute for Chemistry and Technology of Materials, Graz University of Technology, Stremayrgasse 9, 8010, Graz, Austria.
⁶ IST Austria (Institute of Science and Technolog Austria), Am Campus 1, 3400, Klosterneuburg, Austria.

Abstract

We show the synthesis of a redox-active quinone, 2-methoxy-1,4-hydroquinone (MHQ), from a bio-based feedstock and its suitability as electrolyte in aqueous redox flow batteries. We identified semiquinone intermediates at insufficiently low pH and quinoid radicals as responsible for decomposition of MHQ under electrochemical conditions. Both can be avoided and/or stabilized, respectively, using H₃ PO₄ electrolyte, allowing for reversible cycling in a redox flow battery for hundreds of cycles.

Keywords: lignin; quinone; redox-flow batteries; vanillin.

Publication types

Research Support, Non-U.S. Gov't