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Conversion of D-fructose to 5-acetoxymethyl-2-furfural Using Immobilized Lipase and Cation Exchange Resin

1
Green Chemistry & Materials Group, Korea Institute of Industrial Technology (KITECH), 89 Yangdaegiro-gil, Ipjang-myeon, Seobuk-gu, Cheonan, Chungnam 31056, Korea
2
Department of Green Process and System Engineering, Korea University of Science and Technology (UST), 217 Gajeong-ro, Yuseong-gu, Daejeon 34113, Korea
3
Department of Biotechnology, Yonsei University, 50 Yonsei-ro, Seodaemun-gu, Seoul 03722, Korea
*
Author to whom correspondence should be addressed.
Molecules 2019, 24(24), 4623; https://doi.org/10.3390/molecules24244623
Received: 18 November 2019 / Revised: 11 December 2019 / Accepted: 15 December 2019 / Published: 17 December 2019
(This article belongs to the Section Natural Products Chemistry)
5-Acetoxymethyl-2-furfural (AMF) was prepared from D-fructose via 1,6-diacetylfructose (DAF) through a simple two-step reaction pathway. Immobilized enzyme (Novozym 435) was found to be the best enzymatic catalyst for the trans-esterification step (yielding 94.6% DAF). In the dehydration step, while soluble H2SO4 was found to be the best acidic catalyst (yielding 86.6% AMF), we opted to utilize heterogeneous cation exchange resin (Amberlyst 15) together with recyclable industrial solvents (1,4-dioxane) for a more sustainable AMF synthesis procedure. Although the total yield of AMF was a little lower, both the enzyme and the solid acid catalyst could be recycled for five cycles without a significant loss of activity, which has a major contribution to the cost-efficient aspect of the entire process. View Full-Text
Keywords: D-Fructose; 5-Acetoxymethyl-2-furfural (AMF); 5-Hydroxymethyl-2-furfural (HMF); trans-esterification; dehydration. D-Fructose; 5-Acetoxymethyl-2-furfural (AMF); 5-Hydroxymethyl-2-furfural (HMF); trans-esterification; dehydration.
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Huynh, N.T.T.; Lee, K.W.; Cho, J.K.; Kim, Y.J.; Bae, S.W.; Shin, J.S.; Shin, S. Conversion of D-fructose to 5-acetoxymethyl-2-furfural Using Immobilized Lipase and Cation Exchange Resin. Molecules 2019, 24, 4623.

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