To address the difficulties associated with separating HMF from DMSO, we use piperylene sulfone, a solvent with very similar solvatochromic properties to DMSO. These similarities make piperylene sulfone a viable replacement as reaction medium. Piperylene sulfone is formed through a reverse cheletropic reaction between sulfur dioxide and 1,3-trans-piperylene. Superiorly to DMSO, piperylene sulfone can be decomposed to sulfur dioxide and piperylene at temperatures of ~110C which allows for facile separation of reaction products. The off-gassed sulfur dioxide and trans-piperylene can be re-reacted elsewhere to reform the piperylene sulfone, enabling recyclability.
We demonstrate a combined reaction separation system composed of fructose in piperylene sulfone with Amberlyst-15 as catalyst. We will present the results of a statistical design of experiments conducted to optimize conversion of HMF as well as the separation of HMF from piperylene sulfone. We shall also present opportunities for future research using this solvent system.
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