Selective conversion of 5-hydroxymethylfurfural to diketone derivatives over Beta zeolite-supported Pd catalysts in water

Ramos, Rubén; Grigoropoulos, Alexios; Griffiths, Ben L.; Katsoulidis, Alexandros P.; Zanella, Marco; Manning, Troy D.; Blanc, Frédéric; Claridge, John B.; Rosseinsky, Matthew J.

doi:10.1016/j.jcat.2019.04.038

Cited by 31 publications

(37 citation statements)

References 61 publications

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“…The reaction time was varied from 0.5 to 3.0 h. A 33% conversion of HMF was obtained with 73% selectivity to HHD after being reacted for 0.5 h. The conversion of HMF increased with the increase in reaction time and the selectivity to HHD was maintained around 70%. The highest yield of HHD could reach 66% (93% conversion of HMF and 71% selectivity to HHD) when the reaction time was 3.0 h. The mole ratio for HMF/Pd of 420 was among the common amount found in the literature for the conversion of HMF to HHD when using supported Pd as catalysts [32,40,49,52,55,57]. To study the influence of the catalyst amount on conversion and selectivity, we performed the experiments using a different amount of catalysts.…”

Section: Yield Of Hhd From Highly Concentrated Hmfmentioning

confidence: 99%

“…G. Descotes et al gave the first report on this transformation with a yield of 60% of HHD using Pt/C and oxalic acid, in 1991 [48]. After that, there were several reports on the hydrogenation of HMF to HHD catalyzed by heterogeneous or homogeneous precious metal catalysts [48][49][50][51][52][53][54][55][56]. Ir or Ru is favored as a homogeneous catalyst and Pd or Au are effective as heterogeneous catalysts.…”

Section: Introductionmentioning

confidence: 99%

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Preparation of 1-Hydroxy-2,5-hexanedione from HMF by the Combination of Commercial Pd/C and Acetic Acid

Yang

Zhang

et al. 2020

Molecules

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The development of a simple and durable catalytic system for the production of chemicals from a high concentration of a substrate is important for biomass conversion. In this manuscript, 5-hydroxymethylfurfural (HMF) was converted to 1-hydroxy-2,5-hexanedione (HHD) using the combination of commercial Pd/C and acetic acid (AcOH) in water. The influence of temperature, H2 pressure, reaction time, catalyst amount and the concentration of AcOH and HMF on this transformation was investigated. A 68% yield of HHD was able to be obtained from HMF at a 13.6 wt% aqueous solution with a 98% conversion of HMF. The resinification of intermediates on the catalyst was characterized to be the main reason for the deactivation of Pd/C. The reusability of the used Pd/C was studied to find that most of the activity could be recovered by being washed in hot tetrahydrofuran.

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Section: Yield Of Hhd From Highly Concentrated Hmfmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Preparation of 1-Hydroxy-2,5-hexanedione from HMF by the Combination of Commercial Pd/C and Acetic Acid

Yang

Zhang

et al. 2020

Molecules

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“…To avoid acid additives, the introduction of acid sites in the catalyst was a good choice. For example, the reaction could conduct without the addition of acid additives when acid support MIL-101 (Yang et al, 2019b), zeolite (Ramos et al, 2019) or Nb 2 O 5 (Duan et al, 2017b) was used for the preparation of Pd catalyst. The supported Pd was found to be an effective heterogeneous catalyst for this transformation while the Ir complexes were a good homogeneous catalyst candidate (Xu et al, 2017).…”

Section: Introductionmentioning

confidence: 99%

Tungsten Promoted Ni/Al2O3 as a Noble-Metal-Free Catalyst for the Conversion of 5-Hydroxymethylfurfural to 1-Hydroxy-2,5-Hexanedione

et al. 2022

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The conversion of 5-hydroxymethylfurfural (HMF) to 1-hydroxy-2,5-hexanedione (HHD) represented a typical route for high-value utilization of biomass. However, this reaction was often catalyzed by the noble metal catalyst. In this manuscript, W promoted Ni/Al2O3 was prepared as a noble-metal-free catalyst for this transformation. The catalysts were characterized by XRD, XPS, NH3-TPD, TEM, and EDS-mapping to study the influence of the introduction of W. There was an interaction between Ni and W, and strong acid sites were introduced by the addition of W. The W promoted Ni/Al2O3 showed good selectivity to HHD when used as a catalyst for the hydrogenation of HMF in water. The influences of the content of W, temperature, H2 pressure, reaction time, and acetic acid (AcOH) were studied. NiWOx/Al2O3-0.5 (mole ratio of W:Ni = 0.5) was found to be the most suitable catalyst. The high selectivity to HHD was ascribed to the acid sites introduced by W. This was proved by the fact that the selectivity to HHD was increased a lot when AcOH was added just using Ni/Al2O3 as catalysts. 59% yield of HHD was achieved on NiWOx/Al2O3-0.5 at 393 K, 4 MPa H2 reacting for 6 h, which was comparable to the noble metal catalyst, showing the potential application in the production of HHD from HMF.

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“…As a result, the design of an effective catalytic system for the conversion of furan derivatives was one of the key problems for biomass conversion. It was reported that the furfural and HMF could be converted to a various of chemicals such as tetrahydrofurfuryl alcohol, [21–23] furfuryl alcohol, [24] furan‐2,5‐dicarbaldehyde, [25] furan‐2,5‐dicarboxylic acid, [26–30] 2,5‐dimethylfuran, [31–34] 1‐hydroxyhexane‐2,5‐dione (HHD), [35–48] cyclopentanone [49–54] and diols derivatives [55–59] . The products covered the areas of aldehydes, ketones, acids, esters, ethers, and diols.…”

Section: Introductionmentioning

confidence: 99%

Catalytic Hydrogenation of 5‐Hydroxymethylfurfural to Hexanetriol

Zhang

et al. 2022

ChemistrySelect

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The catalytic conversion of furan derivatives, furfural and 5‐hydroxymethylfurfural (HMF), to valuable chemicals is of great importance due to the increase in carbon emissions and decrease in fossil fuels. In this manuscript, 1,2,5‐hexanetriol was transformed to HMF through a two steps procedure. The HMF was first hydrogenated to 1‐hydroxyhexane‐2,5‐dione (HHD). The reaction scale could be enlarged from 1 mmol to 50 mmol of the reactant with a similar yield of HHD, and the purity of HHD was over 95 % after a simple extraction. Then the HHD was hydrogenated to 1,2,5‐hexanetriol on Ru/C at very mild reaction conditions. The parameters of pressure, solvent, the concentration of HHD, reaction time and temperature on the hydrogenation of HHD were investigated to find the optimal reaction conditions. The 1,2,5‐hexanetriol could be obtained from HMF in a one‐pot reaction by removing the Pd/C and adding Ru/C after the HMF hydrogenation step. The fresh and used Pd/C and Ru/C were characterized by XRD, TEM, XPS, and the Ru/C was further characterized by EDS mappings. The characterization showed partial agglomeration of Pd occurred after the Pd/C was used. The Ru/C had a narrow Ru distribution and was stable under the reaction conditions. The Ru/C could be used at least 5 times. This manuscript showed an easy route for the production of valuable chemicals from renewable biomass furan derives.

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Selective conversion of 5-hydroxymethylfurfural to diketone derivatives over Beta zeolite-supported Pd catalysts in water

Cited by 31 publications

References 61 publications

Preparation of 1-Hydroxy-2,5-hexanedione from HMF by the Combination of Commercial Pd/C and Acetic Acid

Preparation of 1-Hydroxy-2,5-hexanedione from HMF by the Combination of Commercial Pd/C and Acetic Acid

Tungsten Promoted Ni/Al2O3 as a Noble-Metal-Free Catalyst for the Conversion of 5-Hydroxymethylfurfural to 1-Hydroxy-2,5-Hexanedione

Catalytic Hydrogenation of 5‐Hydroxymethylfurfural to Hexanetriol

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