Electrocarboxylation of halobenzonitriles: An environmentally friendly synthesis of phthalate derivatives

Irene Reche, Silvia Mena, Iluminada Gallardo, Gonzalo Guirado

Research output: Contribution to journalArticleResearch

1 Citation (Scopus)

Abstract

© 2019 Elsevier Ltd This manuscript presents an efficient approach for producing high valuable compounds using CO2 as building block. The methodology employed is based on electrochemical techniques, which allow performing eco-friendly chemistry solutions and maintaining the aim of offering a potential long-term strategy for reducing the CO2 emissions in the atmosphere, while obtaining useful compounds, such as aromatic acids and phthalate derivatives. This work describes the electrochemical reduction behavior of 4-halobenzonitrile compounds using Glassy Carbon and Silver as cathodes under inert and carbon dioxide atmosphere. Controlled potential electrolysis of 4-halobenzonitriles under CO2 allows obtaining, in very good yields, the corresponding mono- and di-carboxylated organic compounds in CO2-saturated solutions of dimethylformamide containing 0.1 M of tetrabutylammonium tetrafluoroborate. Electro-catalytic effects are seen when Ag is used a cathode, which give very high yields, especially as regards di-carboxylated products. The methodology offers a new “green” route for the synthesis of different phthalate derivatives, which can be potentially used for making plastic polymers in a more environmentally friendly way.
Original languageEnglish
Article number134576
JournalElectrochimica Acta
Volume320
DOIs
Publication statusPublished - 10 Oct 2019

Keywords

  • 4-Halobenzonitrile
  • Carboxylation
  • Cyclic voltammetry
  • Electrochemistry
  • Electrolysis

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