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Micellar Catalysis Strategy of Cross-Condensation Reaction: The Effect of Polar Heads on the Catalytic Properties of Aminoalcohol-Based Surfactants

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Abstract

The effect of the polar head and the concentration of quaternary ammonium surfactants (C14EtOH, C14iPrOH, C14PrOH, where, 14 = carbon number iPrOH = iso-propanol, EtOH = ethanol, PrOH = propanol) in micellar catalysis for the cross-condensation reaction (Claisen–Schmidt) was investigated. The reaction in the Micellar-NaOH system with different concentrations of surfactants above the critical micelle concentration from 15 to 30 mmol between benzaldehyde and acetophenone was used as a model of reaction for this study. The examination of the effectiveness of the catalytic activity reveals that the compound C14EtOH has the best yield (80% of the desired product), followed by C14iPrOH and C14PrOH. The results were interpreted according to the solubilization capacity, droplet size analysis of reagents (benzaldehyde and acetophenone) in the micellar medium and stability of reaction intermediate (enolate) by the electrostatic interactions generated by positive charge of N+ quaternary ammonium atom. Therefore, the quantum calculations carried out by DFT method for surfactants in the aqueous medium, show that electrophilicity degree and the reaction yield% for three cationic surfactants varies in the same following order: C14PrOH < C14iPrOH < C14EtOH.

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Authors and Affiliations

  1. Laboratoire de physico-chimie des matériaux inorganiques et organiques, Centre des Sciences des Matériaux, Ecole Normale supérieure-Rabat, Mohammed V University in Rabat, Rabat, Morocco

    Zakaria Hafidi & Mohammed El Achouri

  2. Equipe de Matériaux, Catalyse & Valorisation des Ressources Naturelles, Université Ibn Zohr, BP 8106, 80000, Agadir, Morocco

    Mohamed Ait Taleb

  3. Equipe de Chimie Bio-Organique Appliquée, Université Ibn Zohr, BP 8106, 80000, Agadir, Morocco

    Mohamed Ait Taleb

  4. Laboratoire de Matériaux, Catalyse et Valorisation des Ressources Naturelles, URAC 24, FST Mohammadia, Université Hassan II-Casablanca, Casablanca, Morocco

    Abdallah Amedlous

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  1. Zakaria Hafidi
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  2. Mohamed Ait Taleb
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Hafidi, Z., Ait Taleb, M., Amedlous, A. et al. Micellar Catalysis Strategy of Cross-Condensation Reaction: The Effect of Polar Heads on the Catalytic Properties of Aminoalcohol-Based Surfactants. Catal Lett 150, 1309–1324 (2020). https://doi.org/10.1007/s10562-019-03045-6

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