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Journal Article

Synthesis of Butyl Levulinate Based on α-Angelica Lactone in the Presence of Easily Separable Heteropoly Acid Catalysts

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Al Shaal, Mohammad Ghith
Research Department Schüth, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Palkovits, Regina
Chair of Heterogeneous Catalysis and Chemical Technology, RWTH Aachen University, Aachen, Germany;
Research Group Palkovits, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Yi, X., Al Shaal, M. G., Ciptonugroho, W., Delidovich, I., Wang, X., & Palkovits, R. (2017). Synthesis of Butyl Levulinate Based on α-Angelica Lactone in the Presence of Easily Separable Heteropoly Acid Catalysts. ChemSusChem. doi:10.1002/cssc.201601882.

Abstract

A series of choline (Ch)-exchanged heteropoly acids (HOCH₂CH₂N(CH₃)₃)_xH_(6−x)P₂W₁₈O₆₂ [abbreviated as Ch_xH_(6−x)P₂W₁₈O₆₂, x=1–6] was synthesized and used as catalysts for the reaction of α-angelica lactone (alpha-AL) with n-butanol to form butyl levulinate (BL). The solubility of Ch_xH_(6−x)P₂W₁₈O₆₂, in the reaction mixture was temperature dependent: The catalysts were soluble under the reaction conditions and precipitated upon cooling of the reaction mixture. This facilitated recovery of the catalysts from the liquid phase. Importantly, an increase of the Ch content caused a decrease of the catalyst solubility. Catalytic activity of Ch_xH_(6−x)P₂W₁₈O₆₂, for the reaction with n-butanol appeared to be in good agreement with the concentration of Brønsted-acidic sites. The results suggest that the reaction proceeded through formation of pseudo-butyl levulinate as intermediate. Ch_xH_(6−x)P₂W₁₈O₆₂, exhibited the best balance between catalytic activity and temperature-dependent solubility. The yield of BL reached 79.4 % at full conversion of alpha-AL at a moderate temperature of 75 °C in an open system. Ch_xH_(6−x)P₂W₁₈O₆₂, could be successfully reused five times without significant loss of activity.