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Electrocatalytic Synthesis of Pyridine Oximes using <i>in Situ</i> Generated NH<sub>2</sub>OH from NO species on Nanofiber Membranes Derived from NH<sub>2</sub>‐MIL‐53(Al)

Runan Xiang, Shihan Wang, Peisen Liao, Fangyan Xie, Jiawei Kang, Suisheng Li, Jiahui Xian, Linna Guo, Guangqin Li

2023Angewandte Chemie International Edition99 citationsDOIOpen Access PDF

Abstract

Abstract Pyridine oximes produced from aldehyde or ketone with hydroxylamine (NH 2 OH) have been widely applied in pharmaceutics, enzymatic and sterilization. However, the important raw material NH 2 OH exhibits corrosive and unstable properties, leading to substantial energy consumption during storage and transportation. Herein, this work presents a novel method for directly synthesizing highly valuable pyridine oximes using in situ generated NH 2 OH from electrocatalytic NO reduction with well‐design nanofiber membranes (Al‐NFM) derived from NH 2 ‐MIL‐53(Al). Particularly, 2‐pyridinealdoxime, the precursor of antidote pralidoxime (2‐PAM) for nerve agents suffering from scarcity and high cost, was achieved with a Faraday efficiency up to 49.8 % and a yield of 92.1 %, attributing to the high selectivity of NH 2 OH production on Al‐NFM, further easily reacted with iodomethane to produce 2‐PAM. This study proposes a creative approach, having wide universality for synthesizing pyridine and other oximes with a range of functional groups, which not only facilitates the conversion of exhaust gas (NO) and waste water (NO 2 − ) into valuable chemicals especially NH 2 OH production and in situ utilization through electrochemistry, but also holds significant potential for synthesis of neuro detoxifying drugs to humanity security.

Topics & Concepts

MembranePyridineNanofiberChemistryOxidizing agentGreen chemistryMaterials scienceOrganic chemistryNanotechnologySupramolecular chemistryCrystal structureBiochemistryAmmonia Synthesis and Nitrogen ReductionNanomaterials for catalytic reactionsMetal-Organic Frameworks: Synthesis and Applications