Preparation of 1,3-Dihydroxyphenazine
- Argonne National Laboratory (ANL), Argonne, IL (United States)
- North Central College, Naperville, IL (United States)
- Pacific Northwest National Laboratory (PNNL), Richland, WA (United States)
- Argonne National Laboratory (ANL), Argonne, IL (United States); North Central College, Naperville, IL (United States)
The ability to effectively store energy produced by intermittent renewable sources is a critical challenge for chemists and materials scientists. Redox flow batteries (RFB), which generate current by the flow of electrons between dissolved redox active compounds in separate solutions, are envisioned as a method to store renewable energy at the electrical grid scale. The best known examples of RFBs are driven by redox active metal or main group complexes. Within the past decade, redox active organic molecules have begun to be used in the construction of RFBs with high cell potential and cycle stability, at economical price points. Of particular interest are substituted dihydroxy phenazines, a class of heterocycles, that have recently been used as an anolyte for aqueous organic RFBs. Recent work indicates that different regioisomers of dihydroxyphenazine show dramatically different solubility and stability under electrochemical cycling conditions. Of particular interest was 1,3-dihydroxyphenazine (1,3-DHP), which showed greater than 1.5 M solubility in 2M KOH and excellent electrochemical stability. Current methods of producing 1,3-DHP, however, are low yielding and cumbersome. In the article proposal that follows, we offer an improved method of producing 1,3-DHP at high purity and moderate yield. The method detailed below was used by the Materials Engineering Research Facility (MERF) at Argonne National Lab to deliver more than 1.5 kg of this compound for use in the construction of aqueous organic RFBs.
- Research Organization:
- Pacific Northwest National Laboratory (PNNL), Richland, WA (United States)
- Sponsoring Organization:
- USDOE Office of Electricity (OE); USDOE Office of Energy Efficiency and Renewable Energy (EERE), Office of Sustainable Transportation. Vehicle Technologies Office (VTO)
- Grant/Contract Number:
- AC05-76RL01830; AC02-06CH11357
- OSTI ID:
- 2997109
- Report Number(s):
- PNNL-SA--177953
- Journal Information:
- Organic Syntheses (Online), Journal Name: Organic Syntheses (Online) Vol. 102; ISSN 2333-3553
- Publisher:
- Organic Syntheses, Inc.Copyright Statement
- Country of Publication:
- United States
- Language:
- English
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