Recent advances and mechanistic insights on the production of biomass-derived 2,5-bis(alkoxymethyl)furans

Hu, Lei; Jiang, Yetao; Wang, Xiaoyu; He, Aiyong; Xu, Jiaxing; Wu, Zhen

doi:10.1007/s13399-020-01062-9

Cited by 20 publications

(22 citation statements)

References 103 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…That is to say, Zr-HTC contained few Brønsted acidic sites, which could prominently reduce the Brønsted acidic site-mediated secondary reactions, such as etherification and ring-opening (Figure 8), and then facilitate the selective synthesis of BHMF. 72 To analyze the strengths of Lewis acidic sites and Lewis basic sites, the elemental compositions and their local environments of ZrO 2 and Zr-HTC were detected by XPS. In Figure 7d, the survey scan spectra further confirmed the existence of Zr, O, and C elements in Zr-HTC.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…In particular, the ratios of Lewis/Brønsted acidic sites in Zr-HTC were determined to be 47.6 and 52.6 at 110 and 250 °C, respectively, demonstrating that Lewis acidic sites were the main acidic sites of Zr-HTC. That is to say, Zr-HTC contained few Brønsted acidic sites, which could prominently reduce the Brønsted acidic site-mediated secondary reactions, such as etherification and ring-opening (Figure ), and then facilitate the selective synthesis of BHMF …”

Section: Results and Discussionmentioning

confidence: 99%

See 1 more Smart Citation

High-Efficiency Catalytic Transfer Hydrogenation of Biomass-Based 5-Hydroxymethylfurfural to 2,5-Bis(hydroxymethyl)furan over a Zirconium–Carbon Coordination Catalyst

Zhang

et al. 2021

ACS Sustainable Chem. Eng.

Self Cite

View full text Add to dashboard Cite

Constructing a cheap and high-performance catalyst is very important for the selective synthesis of biomass-based 2,5-bis(hydroxymethyl)furan (BHMF) from 5-hydroxymethylfurfural via the strategy of catalytic transfer hydrogenation (CTH). Herein, we synthesized a neoteric zirconium–carbon coordination catalyst (Zr-HTC) via a simple self-assembly method, in which glucose-derived hydrothermal carbon (HTC) containing abundant carboxyl and phenolic hydroxyl groups was directly used as a low-cost organic ligand. Satisfyingly, Zr-HTC showed an outstanding catalytic activity for the selective synthesis of BHMF in isopropanol (iPrOH). After 4 h at a mild temperature of 120 °C, 99.2% BHMF yield with 5.61 h–1 turnover frequency (TOF) could be obtained. Detailed experimental results demonstrated that this outstanding catalytic activity of Zr-HTC was mainly contributed by the synergetic effects of Lewis acid–base sites (Zr4+–O2–) with high contents, proper ratios, and strengths under the aid of good hydrophilicity. In addition, Zr-HTC displayed superior catalytic stability, and when it was repeatedly used for five reaction cycles, no noticeable decrease in BHMF yield was found. More significantly, Zr-HTC could also effectively convert a wide range of carbonyl compounds, such as 1-butanal, 1-hexanal, furfural, cyclohexanal, benzaldehyde, phenylacetaldehyde, cyclopentanone, cyclohexanone, levulinic acid, and ethyl levulinate, to the relevant products in iPrOH. Overall, this work offers a new viewpoint to develop more practical zirconium-containing coordination catalysts for the selective synthesis of valuable chemicals via CTH.

show abstract

Section: ■ Results and Discussionmentioning

confidence: 99%

Section: Results and Discussionmentioning

confidence: 99%

High-Efficiency Catalytic Transfer Hydrogenation of Biomass-Based 5-Hydroxymethylfurfural to 2,5-Bis(hydroxymethyl)furan over a Zirconium–Carbon Coordination Catalyst

Zhang

et al. 2021

ACS Sustainable Chem. Eng.

Self Cite

View full text Add to dashboard Cite

show abstract

“… [113–118] Among them, DHMF and DMF have a kind of special symmetrical structure. DHMF can be widely used to produce ethers, [119–122] ketones [123–124] and polymers [125–129] . DMF is promising liquid biofuel that can be transported conveniently [130–131] .…”

Section: Introductionmentioning

confidence: 99%

Progress in Selective Conversion of 5‐Hydroxymethylfurfural to DHMF and DMF

Zhang

et al. 2022

ChemistrySelect

View full text Add to dashboard Cite

Biomass is viewed as an important renewable carbon source, in which 5‐hydroxymethylfurfural (HMF) plays an important role as platform compound. 2, 5‐dihydroxymethylfuran (DHMF) and 2, 5‐dimethylfuran (DMF) could be obtained by the hydrogenation of HMF under certain conditions. The DHMF and DMF are chemicals of high added value with wide application.The catalysts played a key role in the conversion of HMF to DHMF and DMF. This review paid attentions on the hydrogenation of HMF to DHMF and the hydrogenolysis of HMF to DMF via kinds of catalytic systems. The recent progress were summarized according to catalytic system, including noble metal catalysts and non‐noble metal catalysts and a perspective on the transformation was given based on the recent progress.

show abstract

“…Somewhat in parallel to the conversion of Fur to FA, the hydrogenation of Hmf gives 2,5-bis(hydroxymethyl)furan (BHMF), which is a versatile compound for the production of resins [ 7 , 25 , 26 ], polymers [ 7 , 9 , 26 , 27 , 28 , 29 ], foams, fibres [ 9 , 10 , 26 ], and drugs [ 7 , 26 , 28 , 29 ] and for useful bioproducts such as ethers [ 7 , 19 , 26 , 27 , 28 , 30 ]. In particular, 2,5-bis(alkoxymethyl)furans (BAMFs) may have improved properties as diesel additives (such as higher cetane number, higher boiling point, higher stability and energy density) in relation to 5-(alkoxymethyl)furfural or ethanol [ 27 , 31 , 32 , 33 ]. BAMFs can be blended with commercial diesel in up to 40 vol%, contributing to reduced emissions of fumes, oxynitrides, and oxysulfides [ 31 ].…”

Section: Introductionmentioning

confidence: 99%

“…In particular, 2,5-bis(alkoxymethyl)furans (BAMFs) may have improved properties as diesel additives (such as higher cetane number, higher boiling point, higher stability and energy density) in relation to 5-(alkoxymethyl)furfural or ethanol [ 27 , 31 , 32 , 33 ]. BAMFs can be blended with commercial diesel in up to 40 vol%, contributing to reduced emissions of fumes, oxynitrides, and oxysulfides [ 31 ]. BAMFs may have more value than the respective monoethers due to the superior miscibility with diesel and higher stability of the former [ 32 , 34 ].…”

Section: Introductionmentioning

confidence: 99%

Catalytic Transfer Hydrogenation and Acid Reactions of Furfural and 5-(Hydroxymethyl)furfural over Hf-TUD-1 Type Catalysts

et al. 2021

View full text Add to dashboard Cite

Heterogeneous catalysis, which has served well the petrochemical industry, may valuably contribute towards a bio-based economy by sustainably enabling selective reactions to renewable chemicals. Carbohydrate-containing matter may be obtained from various widespread sources and selectively converted to furanic platform chemicals: furfural (Fur) and 5-(hydroxymethyl)furfural (Hmf). Valuable bioproducts may be obtained from these aldehydes via catalytic transfer hydrogenation (CTH) using alcohols as H-donors under relatively moderate reaction conditions. Hafnium-containing TUD-1 type catalysts were the first of ordered mesoporous silicates explored for the conversion of Fur and Hmf via CTH/alcohol strategies. The materials promoted CTH and acid reactions leading to the furanic ethers. The bioproducts spectrum was broader for the reaction of Fur than of Hmf. A Fur reaction mechanism based on literature data was discussed and supported by kinetic modelling. The influence of the Hf loading and reaction conditions (catalyst load, type of alcohol H-donor, temperature, initial substrate concentration) on the reaction kinetics was studied. The reaction conditions were optimized to maximize the yields of 2-(alkoxymethyl)furan ethers formed from Fur; up to 63% yield was reached at 88% Fur conversion, 4 h/150 °C, using Hf-TUD-1(75), which was a stable catalyst. The Hf-TUD-1(x) catalysts promoted the selective conversion of Hmf to bis(2-alkoxymethyl)furan; e.g., 96% selectivity at 98% Hmf conversion, 3 h/170 °C for Hf-TUD-1(50).

show abstract

Recent advances and mechanistic insights on the production of biomass-derived 2,5-bis(alkoxymethyl)furans

Cited by 20 publications

References 103 publications

High-Efficiency Catalytic Transfer Hydrogenation of Biomass-Based 5-Hydroxymethylfurfural to 2,5-Bis(hydroxymethyl)furan over a Zirconium–Carbon Coordination Catalyst

High-Efficiency Catalytic Transfer Hydrogenation of Biomass-Based 5-Hydroxymethylfurfural to 2,5-Bis(hydroxymethyl)furan over a Zirconium–Carbon Coordination Catalyst

Progress in Selective Conversion of 5‐Hydroxymethylfurfural to DHMF and DMF

Catalytic Transfer Hydrogenation and Acid Reactions of Furfural and 5-(Hydroxymethyl)furfural over Hf-TUD-1 Type Catalysts

Contact Info

Product

Resources

About