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Citation: LIU Lin, WEI Yun-Yang, YUE Cai-Bo, JI Liu-Yan. Oxidation of Alcohols to Corresponding Aldehydes and Ketones with Molecular Oxygen Catalyzed by Task-Specific Ionic Liquid[J]. Chinese Journal of Applied Chemistry, ;2007, 24(11): 1327-1331. shu

Oxidation of Alcohols to Corresponding Aldehydes and Ketones with Molecular Oxygen Catalyzed by Task-Specific Ionic Liquid

1.
Institute of Chemical Engineering, Nanjing University of Science and Technology, Nanjing 210094

Corresponding author: WEI Yun-Yang,
Received Date: 3 December 2006
Available Online: 30 April 2007

Reaction of 2,2,6,6-tetramethylpiperidin-4-ol-N-oxyl(TEMPO) with 2-chloroacetyl chloride gave 4-chloroacetoxy-2,2,6,6-tetramethylpiperidine-N-oxyl. An ionic-liquid immobilized TEMPO(TEMPO-IL) was then obtained via the quaternization of 1-methyl-1H-imidazole with 4-chloroacetoxy-2,2,6,6-tetramethyl-piperidine-N-oxyl followed by ion exchange with KPF₆. A selective and mild ionic-liquid immobilized TEMPO/CuCl catalyzed oxidation procedure of alcohols to the corresponding aldehydes and ketones with molecular oxygen in ionic liquid [bmim]PF₆ was developed. Oxidation reactions of benzylic and allylic alcohols were completed in about 10 hours at 65℃ with a conversion of 99% and 80%~90% product yields. Oxidation reactions of aliphatic and heterocyclic alcohols were more difficult with low conversion and yield. The reaction was highly product-selective and in any case only aldehyde or ketone was formed. No carboxylic acid was detected. The solvent and catalyst were easily recovered and reused in the reaction. In the case of the oxidation of benzyl alcohol, the solvent and catalyst were recovered and reused for 6 times with no decreases of benzyl alcohol conversion and product yield.
- task-specific ionic liquids,
- molecular oxygen,
- oxidation,
- alcohol
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