Applied Chemistry for Engineering (공업화학)

The Korean Society of Industrial and Engineering Chemistry (한국공업화학회)
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Development of Ruthenium/TEMPO/Nitrate Catalyst System for Efficient Oxidation of Isosorbide

아이소소바이드의 효과적 산화반응을 위한 루테늄/템포/나이트레이트 촉매 시스템 개발

  • Irshad, Mobina (Department of Chemical Engineering, Kangwon National University) ;
  • Yu, Jung-Ah (Department of Chemical Engineering, Kangwon National University) ;
  • Oh, Youngtak (Center for Environment, Health, and Welfare Research, Korea Institute of Science and Technology (KIST)) ;
  • Kim, Jung Won (Department of Chemical Engineering, Kangwon National University)
  • 이르샤드 모비나 (강원대학교 에너지공학부 에너지화학공학전공) ;
  • 유정아 (강원대학교 에너지공학부 에너지화학공학전공) ;
  • 오영탁 (한국과학기술원 기후환경연구소 환경복지연구단) ;
  • 김정원 (강원대학교 에너지공학부 에너지화학공학전공)
  • Received : 2022.01.06
  • Accepted : 2022.01.20
  • Published : 2022.02.10
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Abstract

This research work reports the development of a Ruthenium/2,2,6,6-tetramethylpiperidine-N-oxyl (TEMPO)/nitrate catalyst system for the highly selective transformation of isosorbide (1,4:3,6-dianhydro-D-glucitol) to isosorbide-diketone (2,6-dioxabicyclo (3,3,0)octan-4,8-one). Isosorbide is a critical platform molecule for future manufacturing processes. TEMPO has been utilized to convert alcohols to carbonyl compounds for a long time. The optimal chemical reaction condition was found to be when using isosorbide (0.5 mmol) with supported Ru (10 mol%), TEMPO (5 mol%), and sodium nitrate (0.03 mmol) in the presence of acetic acid (3 ml) as a solvent at 50 ℃ and 1 atm oxygen pressure. This catalyst system demonstrated good selectivity (> 97%) and yield (87%) with respect to the desired product, in addition to a putative catalytic double oxidation mechanism.

본 연구에서는 아이소소바이드(1,4:3,6-dianhydro-D-glucitol)로부터 그에 상응하는 아이소소바이드-디케톤[2,6-dioxabicyclo(3,3,0)octan-4,8-one]으로의 높은 선택적 전환을 통한 효율적인 루테늄/템포/나이트레이트 촉매 시스템 개발에 대해 보고한다. 미래의 제조 공정에서의 중요한 플랫폼 화합물 중 하나는 아이소소바이드이다. 오랜 시간 동안, TEMPO(2,2,6,6-tetramethylpiperidine-N-oxyl)는 알코올을 카보닐 화합물로 변환하는데 사용되어 왔다. 본 화학 반응에서는 산소 1atm 압력하에, Ru (10 mol%), TEMPO (5 mol%), 질산나트륨(0.03 mmol) 그리고 아이소소바이드(0.5 mmol)를 용매 아세트산(3 ml)을 사용하여 최적화되었다. 이러한 촉매 시스템은 이중 산화 촉매 반응 메커니즘에 대한 가능성뿐만 아니라, 생성물에 대한 원하는 반응물의 높은 선택성(> 97%)과 수율(87%)을 보여주었다.

Keywords

Acknowledgement

This study was supported by 2018 Research Grant (PoINT) from Kangwon National University.

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