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Article Navigation >  Green Energy&Environment  > 2019  >  4(3): 293-299
Gang Wang, Zengxi Li, Chunshan Li, Suojiang Zhang. In-situ generated ionic liquid catalyzed aldol condensation of trioxane with ester in mild homogeneous system. Green Energy&Environment, 2019, 4(3): 293-299. doi: 10.1016/j.gee.2018.11.004
Citation: Gang Wang, Zengxi Li, Chunshan Li, Suojiang Zhang. In-situ generated ionic liquid catalyzed aldol condensation of trioxane with ester in mild homogeneous system. Green Energy&Environment, 2019, 4(3): 293-299. doi: 10.1016/j.gee.2018.11.004
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In-situ generated ionic liquid catalyzed aldol condensation of trioxane with ester in mild homogeneous system

doi: 10.1016/j.gee.2018.11.004
  • a.

    School of Chemical Sciences, University of Chinese Academy of Sciences, 100049, China

  • b.

    Beijing Key Laboratory of Ionic Liquids Clean Process, State Key Laboratory of Multiphase Complex Systems, The National Key Laboratory of Clean and Efficient Coking Technology, Institute of Process Engineering, Chinese Academy of Sciences, Beijing 100190, China

More Information
  • Corresponding author: E-mail address: zxli@ipe.ac.cn (Zengxi Li); E-mail address: csli@ipe.ac.cn (Chunshan Li)
  • Received date 24 September 2018, Accepted date 28 November 2018, RevRecd date 25 October 2018, Available online 06 December 2018, Publish date 31 July 2019,
    Abstract
  • α, β-unsaturated esters were often synthesized from aldehydes and esters in the presence of strong organic base that was very sensitive to air and moisture via aldol reaction. Trioxane was very useful C1 resource, however, the decomposition of it was always the challenging problem that facing researchers. Herein, a novel synthetic methodology for α, β-unsaturated ester preparation from trioxane and ester with mild catalysis of generated ammonium trifluoromethanesulfonate ionic liquid. The enolization of ester as well as the decomposition of trioxane could proceed easily in the presence of boryl trifluoromethanesulfonate and amine at 20–25 °C. Then the enolate and decomposed formaldehyde occurs aldol reaction to form α, β-unsaturated ester. With this strategy, the yield and selectivity of product from various substrates including aliphatic esters, lactones and thioester could reach up to 85.2% and 90.1%.

     

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