Applied Chemistry for Engineering (공업화학)

The Korean Society of Industrial and Engineering Chemistry (한국공업화학회)
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Electrochemical Synthesis of 𝛽-Hydroxynitrile by addition of Acetonitrile into Benzyl Alcohol

벤질알코올과 아세토나이트릴의 반응을 통한 𝛽-hydroxynitrile의 전기화학적 합성

  • Choi, Hyebin (Department of Chemistry, Gyeongsang National University) ;
  • An, Jaun (Department of Chemistry, Gyeongsang National University) ;
  • Kwon, Ki-Young (Department of Chemistry, Gyeongsang National University)
  • 최혜빈 (경상국립대학교 화학과) ;
  • 안자운 (경상국립대학교 화학과) ;
  • 권기영 (경상국립대학교 화학과)
  • Received : 2022.06.15
  • Accepted : 2022.07.07
  • Published : 2022.08.10
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Abstract

𝛽-Hydroxynitrile and 𝛽-ketonitrile were synthesized by the electrochemical oxidation of benzyl alcohol in an acetonitrile solvent. 𝛽-Hydroxynitrile was prepared by the reaction between benzaldehyde from the oxidation of benzyl alcohol and acetonitrile anion which was produced from the electrochemical reduction of acetonitrile. 𝛽-Hydroxynitrile was finally electrochemically converted into 𝛽-ketonitrile by applying 20 mA of current for 3 h. We demonstrated that 𝛽-hydroxynitrile or 𝛽-ketonitrile syntheses were prepared by electrochemical oxidation of benzyl alcohol with a commonly used Pt electrode at room temperature.

벤질알코올의 전기화학적 산화를 통해 𝛽-hydroxynitrile과 𝛽-ketonitrile을 합성하였다. 이 생성물은 용매인 아세토나이트릴이 전기화학적으로 환원되어 생성된 아세토나이트릴 음이온과 벤질알코올이 산화된 벤즈알데하이드의 첨가반응을 통해 생성되었을 것이라고 예상된다. 그리고 20 mA의 전류를 3 h 인가하였을 때, cyanomethylation를 통해 생성된 𝛽-hydroxynitrile이 전기화학적으로 산화되어 최종적으로 𝛽-ketonitrile이 합성됨을 확인하였다. 본 연구에서는 상온에서 가장 범용적으로 사용되는 백금 전극을 이용하여 벤질알코올을 전기화학적으로 𝛽-hydroxynitrile 또는 𝛽-ketonitrile로 합성하는 것이 가능한 것을 입증하였다.

Keywords

Acknowledgement

이 연구는 2020년도 경상국립대학교 연구년제 연구교수 연구지원비와 2020년도 교육부의 재원으로 한국기초과학지원연구원 국가연구시설장비진흥센터의 지원을 받아 수행된 연구임(2019R1A6C1010042).

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