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Metal Catecholates: Synthetic, Preparative, and Manufacturing Methods

IP.com Disclosure Number: IPCOM000250094D
Publication Date: 2017-May-31

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John C. Goeltz: AUTHOR

Abstract

Methods of preparation, synthesis, and manufacturing of flow battery active materials are described with a focus on metal ligand coordination complexes. In particular, methods pertaining to titanium complexes comprising catechol (1,2-dihydroxybenzene) are treated in depth. The methods described here enable a broad range of conditions whereby materials useful for energy storage may readily be prepared.

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Metal Catecholates: Synthetic, Preparative, and Manufacturing Methods

John C. Goeltz, PhD

Assistant Professor of Chemistry

California State University, Monterey Bay

School of Natural Sciences

100 Campus Center

Seaside, CA 93923

jgoeltz@csumb.edu

List of abbreviations:

Catechol - Cat; pyrogallol - Gal; lactate - Lac; ethylene glycolate - EG; 1,2,4-trihydroxybenzene - 1,2,4-THB; ascorbate - Asc; salicylate - Sal; tetrahydrofuran - THF; L-dopamine - L-DOPA; ethylenediamine tetraacetic acid - EDTA; nitrilotriacetic acid - NTA; diethylenetriaminepentaacetic acid - DTPA; OEt - ethoxide; OiPr - isopropoxide; OR - alkoxide; OAr - aryloxide; Tiron - disodium 4,5-dihydroxy-1,3-benzenedisulfonate

Keyword strings:

flow battery; energy storage; active material; electrolyte; negolyte; metal ligand complex; coordination complex; titanium; pyrocatechol; catechol; catecholate; pyrogallol; pyrogallate; gallate; hydroxybenzene; dihydroxybenzene; trihydroxybenzene; polyphenol; polyol; polyalkolxide; ligatable; amine; amino; sulfonated; bridged aromatic; aqueous phase; organic phase; base; alkali metal; titanium tetrachloride; titanium oxychloride; titanium oxysulfate; titanium dioxide; anatase; rutile; hydrous titanium dioxide; hydrothermal; solvothermal; Tiron.

Abstract: 

Methods of preparation, synthesis, and manufacturing of flow battery active materials are described with a focus on metal ligand coordination complexes.  In particular, methods pertaining to titanium complexes comprising catechol (1,2-dihydroxybenzene) are treated in depth.  The methods described here enable a broad range of conditions whereby materials useful for energy storage may readily be prepared.

Introduction

Metal catecholate complexes have been investigated as analogues for iron-binding proteins, as precursors to metal oxide materials, and more recently as a redox couple for energy storage.  Titanium catecholates in particular exhibit reversible electrochemical reduction and large formation constants and so have been of recent interest in energy storage.  This document serves to describe methods of forming metal catecholates at laboratory, pilot, and production scales.  While many of the methods described are for titanium and catechol itself (i.e., 1,2-dihydroxybenzene), some of those described include other metal centers, such as iron, and/or other ligands, such as pyrogallol (1,2,3-trihydroxybenzene), L-DOPA, or ascorbate.  Some include heteroleptic complexes such as TiCat2Gal2- or mixtures of related metal-ligand complexes such as TiCat32- and TiCat2Gal2-.  It is also to be appreciated that many methods extend beyond any specific embodiments put forward here and are instructive in relation to analogous compounds.

Figure 1. Molecular structures of TiCat32- and TiCat2Gal2-

For all methods, unless unfeasible in a way specific to that method, a titanium precursor may be chosen from TiO2, hydrous TiO2; TiCl4 or another titanium halide; a titanium alkoxide, aryl oxide, or mixture...