Fluorination

Living Edition
| Editors: Jinbo Hu, Teruo Umemoto

Electrochemical Fluorination for Preparation of Alkyl Fluorides

  • Toshio FuchigamiEmail author
  • Shinsuke Inagi
Living reference work entry
DOI: https://doi.org/10.1007/978-981-10-1855-8_7-1

Introduction

Electrochemical fluorinations of organic compounds are classified into three processes: Simons’ process, Philips’ process, and partial (selective) fluorination process.

The Simons’ process is the oldest technique, which is a highly useful route to many perfluorinated organic compounds [1, 2]. A solution or dispersion of organic substrate is electrolyzed at a Ni anode in anhydrous hydrogen fluoride (AHF). The products are mostly perfluorinated, and they are commercially significant materials like perfluoroalkanes, perfluoroacyl fluorides, perfluoroalkanesulfonyl fluorides, perfluorotrialkylamines, and perfluoroalkyl esters. The mechanism of the Simons’ process seems to involve the generation of cationic intermediates and high-valence nickel fluorides.

The Phillips’ process utilizes a porous carbon anode in a molten KF-2HF electrolyte [2].

The substrate, typically a gas or volatile liquid particularly insoluble in the electrolyte, is introduced through the porous anode and...

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© Springer Nature Singapore Pte Ltd. 2018

Authors and Affiliations

  1. 1.Department of ElectrochemistryTokyo Institute of TechnologyMidori-kuJapan