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Phase Transfer Catalysis with Quaternary Ammonium Type Gemini Surfactants: O-Alkylation of Isovanillin

  • Original Article
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Journal of Surfactants and Detergents

Abstract

In this paper, O-alkylation of isovanillin with unusual phase transfer catalysts alkandiyl-α,ω-bis(dimethylalkylammonium bromide) dimeric surfactants (also known as gemini surfactants) is described. Some dimeric surfactants with simple hydrophobic alkyl chains and others with hydrophobic alkyl chains containing ester functionalities with different lengths were synthesized and characterized in our laboratory. The alkylation of isovanillin with alkyl halide was successively carried out in the presence of potassium carbonate and a phase transfer catalyst in tetrahydrofuran. The same reactions were also performed with both the traditional phase transfer catalyst tetrabutylammonium bromide and without any catalyst. The results were compared with those of dimeric surfactants. Consequently, it was expressed that alkandiyl-α,ω-bis(dimethylalkylammonium bromide) dimeric surfactants successively exhibit the character of phase transfer catalysts through environmentally friendly procedures under mild conditions. The most significant feature of this work is that dimeric surfactants have been determined to act as phase transfer agents.

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Acknowledgments

The authors would like to acknowledge financial support from the Scientific Research Project Unit of Trakya University (Project No: 2011/135).

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Trakya University, 22030, Edirne, Turkey

    Mesut Boz & Sedat Semih Baştürk

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  1. Mesut Boz
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  2. Sedat Semih Baştürk
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Correspondence to Mesut Boz.

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Boz, M., Baştürk, S.S. Phase Transfer Catalysis with Quaternary Ammonium Type Gemini Surfactants: O-Alkylation of Isovanillin. J Surfact Deterg 19, 663–671 (2016). https://doi.org/10.1007/s11743-016-1821-z

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  • DOI: https://doi.org/10.1007/s11743-016-1821-z

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