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Reaction Kinetics, Mechanisms and Catalysis

, Volume 127, Issue 2, pp 727–740 | Cite as

Acid catalyzed acetalization of aldehydes with diols resulting into the formation of fragrant cyclic acetals

  • Lada SekerováEmail author
  • Markéta Spáčilová
  • Eliška Vyskočilová
  • Jiří Krupka
  • Libor Červený
Article
  • 48 Downloads

Abstract

The influence of reaction conditions (amount and type of the catalyst, the reaction temperature, the type of the solvent) on the reaction course of the acetalization of aldehydes with diols was tested in this paper. The optimization of reaction conditions was performed on model reaction, acetalization of 2-methylpentanal by 2-methyl-2-propyl-1,3-propanediol leading to the formation of fragrant compound 2-(1-methylbutyl)-5-methyl-5-propyl-1,3-dioxane (Troenan). p-Toluenesulfonic acid was used as an active homogeneous catalyst. It appeared to be advantageous not to use any solvent in the reaction. Using 0.3 wt% of the catalyst the almost total conversion of 2-methylpentanal was achieved after 240 min of reaction at room temperature while the selectivity to the desired product was about 98%. The optimized reaction conditions were applied to the preparation of four cyclic fragrant acetals (namely 2-hexyl-1,3-dioxolane, 2-hexyl-4-methyl-1,3-dioxolane, 2-benzyl-5-hydroxy-1,3-dioxane and 2-(1-methylbutyl)-5-methyl-5-propyl-1,3-dioxane) in larger scale; and these were sensory evaluated after purification step. Prepared heterogeneous catalysts, acid modified montmorillonite (MMT) K-10 (treated by H2SO4, HNO3, and HCl) were successful in the model reaction. The conversion of 2-methylpentanal over 90% was achieved using acid modified MMT after 300 min of reaction at room temperature, the selectivity to the desired product was about 98%. MMT/H2SO4 can be used in the model reaction four times without any change in the reaction course, what makes it promising for the further application.

Keywords

Dioxane Dioxolane Troenan Acetalization Cyclic acetals 

Notes

Acknowledgements

This work was realized within the Operational Programme Prague – Competitiveness (CZ.2.16/3.1.00/24501) and “National Program of Sustainability” ((NPU I LO1613) MSMT-43760/2015). We also acknowledge Specific University Research (MSMT NO 21-SVV/2019).

Supplementary material

11144_2019_1595_MOESM1_ESM.docx (65 kb)
Supplementary material 1 (DOCX 64 kb)

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Copyright information

© Akadémiai Kiadó, Budapest, Hungary 2019

Authors and Affiliations

  • Lada Sekerová
    • 1
    Email author
  • Markéta Spáčilová
    • 1
  • Eliška Vyskočilová
    • 1
  • Jiří Krupka
    • 1
  • Libor Červený
    • 1
  1. 1.Department of Organic TechnologyUniversity of Chemistry and Technology PraguePrague 6Czech Republic

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