4.7 Article

Degradation of Organic Cations under Alkaline Conditions

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 1, Pages 254-263

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.0c02051

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Funding

  1. Center for Alkaline-based Energy Solutions (CABES), an Energy Frontier Research Center - U.S. Department of Energy, Office of Science, Basic Energy Sciences [DE-SC0019445]
  2. National Science Foundation (NSF) [CHE-1809658, CHE-1531632]

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Understanding the degradation mechanisms of organic cations under basic conditions is crucial for the development of durable alkaline energy conversion devices. An evaluation of 26 model compounds is being conducted to identify cations with improved alkaline stabilities and advance the field.
Understanding the degradation mechanisms of organic cations under basic conditions is extremely important for the development of durable alkaline energy conversion devices. Cations are key functional groups in alkaline anion exchange membranes (AAEMs), and AAEMs are critical components to conduct hydroxide anions in alkaline fuel cells. Previously, we have established a standard protocol to evaluate cation alkaline stability within KOH/CD3OH solution at 80 degrees C. Herein, we are using the protocol to compare 26 model compounds, including benzylammonium, tetraalkylammonium, spirocyclicammonium, imidazolium, benzimidazolium, triazolium, pyridinium, guanidinium, and phosphonium cations. The goal is not only to evaluate their degradation rate, but also to identify their degradation pathways and lead to the advancement of cations with improved alkaline stabilities.

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