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Production of long alkyl ethers in homogeneous systems: A study of glyceryl monododecyl ethers

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Abstract

In this study, the etherification of glycerol was executed with dodecanol through use of homogeneous catalysts. First, a univariate study of direct condensation was executed to determine the effects of the variables reaction time, catalyst type and glycerol:dodecanol molar ratio on the dodecyl ether (DOE) and glyceryl monododecyl ether (GMDE) production. A full 23 factorial design was used to evaluate the effect of glycerol:dodecanol molar ratio, catalyst loading and temperature on the production of dodecyl ether (DOE), glyceryl monododecyl ether (GMDE) substituted on carbon 1 (C1) or carbon 2 (C2). The GMDE yield was 35% in 3 h. The experimental results indicated that rising temperature positively affected GMDE content and higher catalyst loading increased DOE production. In the case of traditional routes, Williamson synthesis produced just 5% GMDE while when applying solketal synthesis, high yield and purity of this compound were obtained, demonstrating the viability of GMDE production.

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All data generated or analyzed during this study are included in this published article and its supplementary information files.

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Acknowledgements

We are grateful to CNPq and CAPES (Brazil) for the financial support in the form of scholarships for our graduate students, and also Federal University of Paraná (UFPR) for supporting the development of this study.

Funding

We are grateful to CNPq and CAPES (Brazil) for the financial support in the form of scholarships for our graduate students, and also Federal University of Paraná (UFPR) for supporting the development of this study.

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Authors and Affiliations

  1. Research Center in Applied Chemistry, CEPESQ - Department of Chemistry, Federal University of Paraná, UFPR, Caixa Postal 19032, Curitiba, Paraná, 81531-980, Brazil

    Débora M. Kochepka, Laís P. Dill, Angelo R. S. Oliveira, Maria Aparecida F. César-Oliveira & Claudiney S. Cordeiro

  2. Laboratory of Polymer Chemistry and Organic Synthesis, LEQUIPE – Departament of Chemistry, Federal University of Paraná, UFPR, Caixa Postal 19032, Curitiba, Paraná, 81531-980, Brazil

    Angelo R. S. Oliveira & Maria Aparecida F. César-Oliveira

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  1. Débora M. Kochepka
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  2. Laís P. Dill
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  3. Angelo R. S. Oliveira
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  4. Maria Aparecida F. César-Oliveira
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  5. Claudiney S. Cordeiro
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All authors contributed to the study’s conception and design. All authors commented on previous versions of the manuscript. All authors read and approved the final manuscript.

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Correspondence to Claudiney S. Cordeiro.

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Kochepka, D.M., Dill, L.P., Oliveira, A.R.S. et al. Production of long alkyl ethers in homogeneous systems: A study of glyceryl monododecyl ethers. Reac Kinet Mech Cat 131, 829–844 (2020). https://doi.org/10.1007/s11144-020-01879-5

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  • DOI: https://doi.org/10.1007/s11144-020-01879-5

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