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Acid Catalyzed Competitive Esterification and Ketalization of Levulinic Acid with 1,2 and 1,3-Diols: The Effect of Heterogeneous and Homogeneous Catalysts

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Abstract

Condensation reactions of levulinic acid (LA) with 1,2-ethanediol (1,2-ED), 1,2-propanediol (1,2-PD), and 1,3-propanediol (1,3-PD) were studied using Amberlyst-15 as well as p-toluenesulfonic acid catalysts in benzene under Dean–Stark conditions. In Amberlyst-15 catalyzed reactions the products are ketals and ketal-esters, whereas p-toluenesulfonic acid catalyzed reactions produce esters and ketal-esters as products. In p-toluenesulfonic acid catalyzed reactions with 1,2-ED and 1,3-PD, LA monoester product is formed as the major product after 180 min in 75 and 97 % yields respectively. Unlike the previously reported acid catalyzed ketalization of ethyl levulinate with diols, combined ketalization–esterification of LA with diols is a complex process.

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Acknowledgments

The authors would like to thank the National Science Foundation (NSF) (through Grant Nos. CBET-0929970, CBET-1336469, HRD-1036593), and the U.S. Department of Agriculture (USDA) (through Grant No. CBG-2010-38821-21569) for financial support.

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Authors and Affiliations

  1. Department of Chemistry, Prairie View A&M University, Prairie View, TX, 77446, USA

    Ananda S. Amarasekara & Moriam A. Animashaun

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  1. Ananda S. Amarasekara
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  2. Moriam A. Animashaun
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Correspondence to Ananda S. Amarasekara.

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Amarasekara, A.S., Animashaun, M.A. Acid Catalyzed Competitive Esterification and Ketalization of Levulinic Acid with 1,2 and 1,3-Diols: The Effect of Heterogeneous and Homogeneous Catalysts. Catal Lett 146, 1819–1824 (2016). https://doi.org/10.1007/s10562-016-1812-8

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  • DOI: https://doi.org/10.1007/s10562-016-1812-8

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