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Cellulose

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One-pot synthesis of alkyl levulinates from biomass derivative carbohydrates in tin(II) exchanged silicotungstates-catalyzed reactions

  • Patrícia Fontes Pinheiro
  • Diêgo Morais Chaves
  • Márcio José da SilvaEmail author
Original Research
  • 9 Downloads

Abstract

Biomass is an attractive source of carbohydrates that can be converted to fuels and fine chemicals. Acid-catalyzed alcoholysis of biomass derivatives provides alkyl levulinates, which are fuel bioadditives, intermediates in the synthesis of drugs and agrochemicals. In this work, we developed a one-pot route to obtain alkyl levulinates using Sn(II) exchanged Keggin heteropolyacids (i.e., H3PW12O40, H3PMo12O40, and H4SiW12O40) as catalysts, in alcoholysis reactions of various carbohydrates. All the catalysts were characterized by FT-IR, XRD, EDS/SEM, TG/DSC, and BET analysis. The tin(II) silicotungstate was the most active and selective catalyst. After 2 h of reaction carried out at 423 K, an almost complete conversion was achieved on the ethanolysis of the fructose, sucrose and inulin, which gave high yields of ethyl levulinate (ca. 78, 71 and 61 mol%, respectively). In all reactions, 5-ethoxymethylfurfural was always the secondary product. Maltose, galactose, and glucose were almost unreactive. The effects of main parameters of reaction, such as temperature, catalyst load, and type of alcohols were assessed. The Sn2SiW12O40 catalyst was easily recovered and successfully reused for 7 cycles, without loss activity.

Graphic abstract

Keywords

Biomass Alkyl levulinates Sn(II)-exchanged Keggin heteropolyacid salts Carbohydrates 

Notes

Acknowledgments

The authors are grateful for the financial support from CAPES, CNPq, and FAPEMIG (Brazil). This study was financed in part by the Coordenação de Aperfeiçoamento de Pessoal de Nível Superior-Brasil (CAPES)—Finance Code 001.

Supplementary material

10570_2019_2665_MOESM1_ESM.docx (2.3 mb)
Supplementary material 1 (DOCX 2400 kb)

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Copyright information

© Springer Nature B.V. 2019

Authors and Affiliations

  1. 1.Department of Physics and ChemistryFederal University of Espírito SantoAlegreBrazil
  2. 2.Chemistry DepartmentFederal University of ViçosaViçosaBrazil
  3. 3.Chemistry DepartmentFederal University of Viçosa, Campus UniversitárioViçosaBrazil

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