Hydrogenation of 5-hydroxymethylfurfural into 2,5-bis(hydroxymethyl)furan over mesoporous Cu–Al2O3 catalyst: From batch to continuous processing

Kim, Jin-Sung; Bathula, Hari Babu; Yun, Seokwon; Jo, Yeongin; Lee, Soo Hyun; Baik, Joon Hyun; Suh, Young Woong

doi:10.1016/j.jiec.2021.06.039

Cited by 29 publications

(19 citation statements)

References 40 publications

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“…The reaction conditions in a batch reactor with a supported Cu catalyst prepared by solvent-deficient precipitation (meso-CuA, with a Cu loading of 20 wt%) have been optimized in our recent report. [15] The hydrogenation performance of meso-CuA should be investigated by varying the content of EA in the ethanol (EtOH) reaction solvent, because a part of the EA solvent can be present in the HMF obtained from CMF and thus affect the hydrogenation activity of meso-CuA. After testing the full range of EA/EtOH weight ratios, HMF conversion and BHMF selectivity values above 99 % were measured under the following reaction conditions: 3.2 wt% HMF, catalyst/HMF weight ratio = 20, 100 °C, 50 bar H 2 , and 3.5 h. Therefore, EA did not suppress the hydrogenation activity.…”

Section: Continuous Hmf Hydrogenation To Bhmfmentioning

confidence: 99%

“…Nonetheless, the EA content should be adjusted to a tolerable value (e. g., 20 wt% EA), because EtOH is considered the effective solvent in the HMF hydrogenation. [15,23,24] In addition, we investigated the storage method of HMF after the hydrolysis of CMF. When HMF was stored in a refrigerator, in some cases the color of the hydrogenation solution turned brown (implying the formation of humins), even if a BHMF yield close to 99 % was achieved.…”

Section: Continuous Hmf Hydrogenation To Bhmfmentioning

confidence: 99%

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5‐(Chloromethyl)Furfural as a Potential Source for Continuous Hydrogenation of 5‐(Hydroxymethyl)Furfural to 2,5‐Bis(Hydroxymethyl)Furan

et al. 2022

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5-(Chloromethyl)furfural (CMF) is cheaper than sugars, because it can be obtained from biomass waste. Herein, the stepwise conversion of CMF to 2,5-bis(hydroxymethyl)furan (BHMF) via 5-(hydroxymethyl)furfural (HMF) was demonstrated for the first time. The purified CMF was hydrolyzed in continuous mode followed by extraction with ethyl acetate (EA), resulting in a HMF yield of 70 mol%. The following factors were assessed during continuous hydrogenation of the produced HMF: the presence of EA in the reaction solvent, HMF concentrations of up to 10 wt% in the feed, the mass production of mesoporous Cu-Al 2 O 3 (meso-CuA-kg), the shaping of meso-CuA-kg into cylindrical pellets, and the setup of the catalytic reactor. Through these efforts, the hydrogenation of HMF over meso-CuA-kg could be sustained for 100 h under the above optimized conditions, affording BHMF in 98 % yield. The approach described in this study can greatly contribute to the valueadded transformation of CMF into HMF and BHMF.

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Section: Continuous Hmf Hydrogenation To Bhmfmentioning

confidence: 99%

Section: Continuous Hmf Hydrogenation To Bhmfmentioning

confidence: 99%

5‐(Chloromethyl)Furfural as a Potential Source for Continuous Hydrogenation of 5‐(Hydroxymethyl)Furfural to 2,5‐Bis(Hydroxymethyl)Furan

et al. 2022

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“…Kim's work provides in-depth guidelines regarding the same for researchers. Kim developed structurally different copper-alumina catalysts, including meso-Cu/Al 2 O 3 , cp-Cu/Al 2 O 3 , and imp-Cu/Al 2 O 3 , via solventdeficient precipitation (SDP), coprecipitation (CP), and impregnation (IMP) methods, respectively, and used them to catalyze the hydrogenation of HMF (Kim et al, 2021). Under the same reaction conditions, as shown in Table 1, entries 4, 5, and 6, the meso-Cu/Al 2 O 3 catalyst outperformed both impregnated and coprecipitated Cu/Al 2 O 3 catalysts in terms of catalytic activity.…”

Section: Hydrogenation Of Carbonyl Inside Hmf To Bhmf With Hmentioning

confidence: 99%

Recent Advances in the Catalytic Hydroconversion of 5-Hydroxymethylfurfural to Valuable Diols

Huang

Wang

Lei³

et al. 2022

Front. Chem.

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Biomass, a globally available resource, is a promising alternative feedstock for fossil fuels, especially considering the current energy crisis and pollution. Biomass-derived diols, such as 2,5-bis(hydroxymethyl)furan, 2,5-bis(hydroxymethyl)-tetrahydrofuran, and 1,6-hexanediol, are a significant class of monomers in the polyester industry. Therefore, the catalytic conversion of biomass to valuable diols has received extensive research attention in the field of biomass conversion and is a crucial factor in determining the development of the polyester industry. 5-Hydroxymethylfurfural (HMF) is an important biomass-derived compound with a C6-furanic framework. The hydroconversion of HMF into diols has the advantages of being simple to operate, inexpensive, environmentally friendly, safe, and reliable. Therefore, in the field of diol synthesis, this method is regarded as a promising approach with significant industrialization potential. This review summarizes recent advances in diol formation, discusses the roles of catalysts in the hydroconversion process, highlights the reaction mechanisms associated with the specificities of each active center, and provides an outlook on the challenges and opportunities associated with the research on biomass-derived diol synthesis.

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“…A mesoporous Cu-Al 2 O 3 catalyst exhibited excellent catalytic performance toward the synthesis of BHMF in a continuous fixed-bed reactor. Presence of water in the reaction medium decreased the catalytic performance due to adsorption on the catalyst's surface, which in turn decreased the surface coverage of HMF [133].…”

Section: Catalytic Reduction Of Hmf To Furanics 221 Hmf To Bhmfmentioning

confidence: 99%

Energy Densification of Biomass-Derived Furfurals to Furanic Biofuels by Catalytic Hydrogenation and Hydrodeoxygenation Reactions

Vinod¹,

Dutta²

2021

Sustainable Chemistry

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The concomitant hydrolysis and dehydration of biomass-derived cellulose and hemicellulose to furfural (FUR) and 5-(hydroxymethyl)furfural (HMF) under acid catalysis allows a dramatic reduction in the oxygen content of the parent sugar molecules with a 100% carbon economy. However, most applications of FUR or HMF necessitate synthetic modifications. Catalytic hydrogenation and hydrogenolysis have been recognized as efficient strategies for the selective deoxygenation and energy densification of biomass-derived furfurals generating water as the sole byproduct. Efficient and eco-friendly catalysts have been developed for the selective hydrogenation of furfurals affording renewable furanic compounds such as 2-methylfuran, 2,5-dimethylfuran and 2-methyltetrahydrofuran with potential applications as biofuel, solvent and chemical feedstock. Hydrogen gas or hydrogen donor molecules, required for the above processes, can also be renewably obtained from biomass using catalytic processes, enabling a circular economy. In this review, the recent developments in the energy densification of furfurals to furanic compounds of commercial significance are elaborated, emphasizing the role of catalyst and the reaction parameters employed. Critical discussion on sourcing hydrogen gas required for the processes, using hydrogen donor solvents, catalyst design and the potential markets of furanic intermediates have been made. Critical evaluations of the accomplishments and challenges in this field are also provided.

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Hydrogenation of 5-hydroxymethylfurfural into 2,5-bis(hydroxymethyl)furan over mesoporous Cu–Al2O3 catalyst: From batch to continuous processing

Cited by 29 publications

References 40 publications

5‐(Chloromethyl)Furfural as a Potential Source for Continuous Hydrogenation of 5‐(Hydroxymethyl)Furfural to 2,5‐Bis(Hydroxymethyl)Furan

5‐(Chloromethyl)Furfural as a Potential Source for Continuous Hydrogenation of 5‐(Hydroxymethyl)Furfural to 2,5‐Bis(Hydroxymethyl)Furan

Recent Advances in the Catalytic Hydroconversion of 5-Hydroxymethylfurfural to Valuable Diols

Energy Densification of Biomass-Derived Furfurals to Furanic Biofuels by Catalytic Hydrogenation and Hydrodeoxygenation Reactions

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