Three-step cascade over a single catalyst: synthesis of 5-(ethoxymethyl)furfural from glucose over a hierarchical lamellar multi-functional zeolite catalyst

Yuanyuan Bai; Lu Wei; Mengfei Yang; Huiyong Chen; Scott Holdren; Guanghui Zhu; Dat T. Tran; Chunli Yao; Runcang Sun; Yanbo Pan; Dongxia Liu

doi:10.1039/C8TA01242C

Three-step cascade over a single catalyst: synthesis of 5-(ethoxymethyl)furfural from glucose over a hierarchical lamellar multi-functional zeolite catalyst†

Yuanyuan Bai,^abc Lu Wei,^ad Mengfei Yang,^e Huiyong Chen,

^e Scott Holdren,^f Guanghui Zhu,^g Dat T. Tran,^h Chunli Yao,^c Runcang Sun,

^c Yanbo Panⁱ and Dongxia Liu

*^a

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* Corresponding authors

^a Department of Chemical and Biomolecular Engineering, University of Maryland, College Park, MD, USA
E-mail: liud@umd.edu
Fax: +1-301-405-0523
Tel: +1-301-405-3522

^b National Engineering Lab for Pulp and Paper, China National Pulp and Paper Research Institute Co. Ltd., Beijing, China

^c Beijing Key Laboratory of Lignocellulosic Chemistry, Beijing Forestry University, Beijing, China

^d College of Materials Science and Engineering, Beijing University of Technology, Beijing 100124, PR China

^e School of Chemical Engineering, Northwest University, Xi'an, Shaanxi, China

^f Department of Chemistry and Biochemistry, University of Maryland, College Park, MD, USA

^g School of Chemical and Biomolecular Engineering, Georgia Institute of Technology, Atlanta, Georgia, USA

^h U. S. Army Research Laboratory, RDRL-SED-E, 2800 Powder Mill Road, Adelphi, MD, USA

ⁱ Department of Chemical and Biomolecular Engineering, University of Akron, Akron 44325, USA

Abstract

The synthesis of hierarchical lamellar zeolites with a controlled meso-/microporous morphology and acidity is an expanding area of research interest for a wide range of applications. Here, we report a one-step synthesis of a hierarchical meso-/microporous lamellar MFI–Sn/Al zeolite (i.e., containing both Lewis acidic Sn- and Al-sites and a Brønsted acidic Al–O(H)–Si site) and its catalytic application for the conversion of glucose into 5-(ethoxymethyl)furfural (EMF). The MFI–Sn/Al zeolite was prepared with the assistance of a diquaternary ammonium ([C₂₂H₄₅–N⁺(CH₃)₂–C₆H₁₂–N⁺(CH₃)₂–C₆H₁₃]Br²⁻, C_22-6-6) template in a composition of 100SiO₂/5C_22-6-6/18.5Na₂O/xAl₂O₃/ySnO₂/2957H₂O (x = 0.5, 1, and 2; y = 1 and 2, respectively). The MFI–Sn/Al zeolites innovatively feature dual meso-/microporosity and dual Lewis and Brønsted acidity, which enabled a three-step reaction cascade for EMF synthesis from glucose in ethanol solvent. The reaction proceeded via the isomerization of glucose to fructose over Lewis acidic Sn sites and the dehydration of fructose to 5-hydroxymethylfurfural (HMF) and then the etherification of HMF and ethanol to EMF over the Brønsted acidic Al–O(H)–Si sites. The co-existence of multiple acidities in a single zeolite catalyst enabled one-pot cascade reactions for carbohydrate upgrading. The dual meso-/microporosity in the MFI–Sn/Al zeolites facilitated mass transport in processing of bulky biomass molecules. The balance of both types of acidity and meso-/microporosity realized an EMF yield as high as 44% from the glucose reactant.

This article is part of the themed collection: Materials and Nano Research in Atlanta

Journal of Materials Chemistry A

Three-step cascade over a single catalyst: synthesis of 5-(ethoxymethyl)furfural from glucose over a hierarchical lamellar multi-functional zeolite catalyst†

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Three-step cascade over a single catalyst: synthesis of 5-(ethoxymethyl)furfural from glucose over a hierarchical lamellar multi-functional zeolite catalyst

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