Baeyer-Villiger Oxidation of Cyclic Ketones Catalyzed by Amino Acid Ionic Liquids

doi:10.1007/s40242-019-9186-z

高等学校化学研究 ›› 2020, Vol. 36 ›› Issue (5): 865-869.doi: 10.1007/s40242-019-9186-z

Baeyer-Villiger Oxidation of Cyclic Ketones Catalyzed by Amino Acid Ionic Liquids

YU Fengli¹, CHI Yujie¹, GAO Chong¹, CHEN Ruirui², XIE Congxia¹, YU Shitao²

1. State Key Laboratory Base of Eco-chemical Engineering, College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao 266042, P. R. China;
2. College of Chemical Engineering, Qingdao University of Science and Technology, Qingdao 266042, P. R. China

收稿日期:2019-07-05 修回日期:2019-08-19 出版日期:2020-10-01 发布日期:2020-10-01
通讯作者: YU Fengli, YU Shitao E-mail:yufliqust@163.com;yushitaoqust@126.com
基金资助:
Supported by the National Natural Science Foundation of China(No.21878166), the Taishan Scholar Project of Shandong Province, China(No.ts201511033), the Emphasis Development Plan of Shandong Province, China(Nos.2017GGX70102, 2017GGX40107) and the Open Project of the Chemistry Department in Qingdao University of Science and Technology of China (No.QUSTHX201811).

Baeyer-Villiger Oxidation of Cyclic Ketones Catalyzed by Amino Acid Ionic Liquids

YU Fengli¹, CHI Yujie¹, GAO Chong¹, CHEN Ruirui², XIE Congxia¹, YU Shitao²

1. State Key Laboratory Base of Eco-chemical Engineering, College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao 266042, P. R. China;
2. College of Chemical Engineering, Qingdao University of Science and Technology, Qingdao 266042, P. R. China

Received:2019-07-05 Revised:2019-08-19 Online:2020-10-01 Published:2020-10-01
Contact: YU Fengli, YU Shitao E-mail:yufliqust@163.com;yushitaoqust@126.com
Supported by:
Supported by the National Natural Science Foundation of China(No.21878166), the Taishan Scholar Project of Shandong Province, China(No.ts201511033), the Emphasis Development Plan of Shandong Province, China(Nos.2017GGX70102, 2017GGX40107) and the Open Project of the Chemistry Department in Qingdao University of Science and Technology of China (No.QUSTHX201811).

摘要/Abstract

摘要： A series of amino-acid-based ionic liquids was synthesized via one-step protonation of the corresponding L-amino acid by utilizing an array of proton sources. The catalytic activity of the amino-acid-based ionic liquids for the Baeyer-Villiger oxidation of cyclic ketones was investigated using cyclopentanone as a model cycloketone. The proline-based ionic liquid [ProH]CF₃SO₃ was shown to exhibit the best catalytic activity. The reaction condition was optimized to give the following reagent ratio of n(cyclopentanone):n(catalyst):n(H₂O₂)=1:0.06:4, 60℃ and 6 h. Under the optimum conditions, the conversion of cyclopentanone was 96.57% and the selectivity for δ-valerolactone was 73.01%. The catalytic activity was shown to be constant after 4 cycles. A simple treatment was allowed for the recover and the reuse of [ProH]CF₃SO₃. The successful utilization of [ProH]CF₃SO₃ to catalyze a host of cyclic ketones via Baeyer-Villiger oxidation clearly demonstrated the capacity of [ProH]CF₃SO₃ to tolerate variation in the substrate.

关键词: Amino acid ionic liquid, Baeyer-Villiger oxidation, Cyclic ketone, Lactone

Abstract: A series of amino-acid-based ionic liquids was synthesized via one-step protonation of the corresponding L-amino acid by utilizing an array of proton sources. The catalytic activity of the amino-acid-based ionic liquids for the Baeyer-Villiger oxidation of cyclic ketones was investigated using cyclopentanone as a model cycloketone. The proline-based ionic liquid [ProH]CF₃SO₃ was shown to exhibit the best catalytic activity. The reaction condition was optimized to give the following reagent ratio of n(cyclopentanone):n(catalyst):n(H₂O₂)=1:0.06:4, 60℃ and 6 h. Under the optimum conditions, the conversion of cyclopentanone was 96.57% and the selectivity for δ-valerolactone was 73.01%. The catalytic activity was shown to be constant after 4 cycles. A simple treatment was allowed for the recover and the reuse of [ProH]CF₃SO₃. The successful utilization of [ProH]CF₃SO₃ to catalyze a host of cyclic ketones via Baeyer-Villiger oxidation clearly demonstrated the capacity of [ProH]CF₃SO₃ to tolerate variation in the substrate.

Key words: Amino acid ionic liquid, Baeyer-Villiger oxidation, Cyclic ketone, Lactone

YU Fengli, CHI Yujie, GAO Chong, CHEN Ruirui, XIE Congxia, YU Shitao. Baeyer-Villiger Oxidation of Cyclic Ketones Catalyzed by Amino Acid Ionic Liquids[J]. 高等学校化学研究, 2020, 36(5): 865-869.

YU Fengli, CHI Yujie, GAO Chong, CHEN Ruirui, XIE Congxia, YU Shitao. Baeyer-Villiger Oxidation of Cyclic Ketones Catalyzed by Amino Acid Ionic Liquids[J]. Chemical Research in Chinese Universities, 2020, 36(5): 865-869.

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Baeyer-Villiger Oxidation of Cyclic Ketones Catalyzed by Amino Acid Ionic Liquids

Baeyer-Villiger Oxidation of Cyclic Ketones Catalyzed by Amino Acid Ionic Liquids

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