Highly Porous Nitrogen- and Phosphorus-Codoped Graphene: An Outstanding Support for Pd Catalysts to Oxidize 5-Hydroxymethylfurfural into 2,5-Furandicarboxylic Acid

Chen, Chunlin; Li, Xingtao; Wang, Lingchen; Liang, Ting; Wang, Lei; Zhang, Yajie; Zhang, Jian

doi:10.1021/acssuschemeng.7b02049

Cited by 63 publications

(40 citation statements)

References 36 publications

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“…In addition, heterogeneous metal catalysts have been applied in HMF oxidation. Especially supported noble metals like Pt [22][23][24] or Pd [25][26][27] are catalytically active in this reaction. Among others, supported gold-based catalysts show high activity in the oxidation of HMF with oxygen to FDCA [28][29][30][31][32][33][34][35].…”

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confidence: 99%

The Influence of the Gold Particle Size on the Catalytic Oxidation of 5-(Hydroxymethyl)furfural

et al. 2020

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For the production of chemicals from biomass, new selective processes are required. The selective oxidation of 5-(Hydroxymethyl)furfural (HMF), a promising platform molecule in fine chemistry, to 2,5-furandicarboxylic acid (FDCA) is considered a promising approach and requires the oxidation of two functional groups. In this study, Au/ZrO 2 catalysts with different mean particle sizes were prepared by a chemical reduction method using tetrakis(hydroxymethyl)phosphonium chloride (THPC) and tested in HMF oxidation. The catalyst with the smallest mean particle size (2.1 nm) and the narrowest particle size distribution was highly active in the oxidation of the aldehyde moiety of HMF, but less active in alcohol oxidation. On the other hand, increased activity in FDCA synthesis up to 92% yield was observed over catalysts with a larger mean particle size (2.7 nm), which had a large fraction of small and some larger particles. A decreasing FDCA yield over the catalyst with the largest mean particle size (2.9 nm) indicates that the oxidation of both functional groups require different particle sizes and hint at the presence of an optimal particle size for both oxidation steps. The activity of Au particles seems to be influenced by surface steps and H bonding strength, the latter particularly in aldehyde oxidation. Therefore, the presence of both small and some larger Au particles seem to give catalysts with the highest catalytic activity.Catalysts 2020, 10, 342 2 of 13 oxidation of HMF has gained great interest in recent years. Selective oxidation of HMF can for example give 5-hydroxymethyl-2-furancarboxylic acid (HFCA) or 2,5-diformylfuran. One of the most important oxidation products is 2,5-furandicarboxylic acid (FDCA), [11,12] which is produced via the oxidation of both functional groups of HMF (Scheme 1). The structural similarity of FDCA to terephthalic acid led to its consideration as one of the twelve important molecules that can be produced from sugar-containing biomass feedstock [11,12]. Therefore, FDCA may be used in future bio-based polymers thus overcoming the need of petrochemical-based terephthalic acid [13,14]. Synthetic approaches for FDCA synthesis include stoichiometric oxidation reactions [15] as well as catalytic routes with mostly molecular oxygen. The latter range from bio-[16,17] to electro-[18-20] and metal catalysis. Current FDCA production is based on the homogeneously catalyzed AMOCO process, which is carried out in acetic acid solvent at 125 • C and 70 bar air in the presence of a Cu/Mn/Br catalyst [21]. In addition, heterogeneous metal catalysts have been applied in HMF oxidation. Especially supported noble metals like Pt [22][23][24] or Pd [25][26][27] are catalytically active in this reaction. Among others, supported gold-based catalysts show high activity in the oxidation of HMF with oxygen to FDCA [28][29][30][31][32][33][34][35]. For example, Au supported on CeO 2 nanoparticles allowed the production of FDCA in 96% yield after 5 h at 130 • C [28].Catalysts 2020, 10, x FOR PEER REVIEW 2 of...

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confidence: 99%

The Influence of the Gold Particle Size on the Catalytic Oxidation of 5-(Hydroxymethyl)furfural

et al. 2020

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“…The introduction of a small amount (~0.2%) of phosphorous in P-PS-CNF and P-LHT-CNF slightly increased the activity of Au-Pt catalysts compared with undoped Au/PS-CNF and Au-Pt/LHT-CNF ( Table 3). The higher P content in P-HHT-CNF (1.19%) has a higher impact on the activity of Au-Pt (368 h −1 and 185 h −1 , for Au-Pt/P-HHT-CNF and Au-Pt/HHT-CNF, respectively) with almost full conversion and 96% of selectivity to FDCA after only 1 h. The beneficial effect of P cannot be attributed to possible changes in Au-Pt aggregation state, as the nanoparticle size is similar to Au-Pt/HHT-CNF (4.5 and 3.9 nm for Au-Pt/HHT-CNF and Au-Pt/P-HHT-CNF, respectively), but rather to the capability of P to modify the electronic properties of the metal active sites, as already envisaged in previous studies for Pd [26][27][28].…”

Section: Resultsmentioning

confidence: 66%

“…This evidence could be related to the interaction between Au-Pt NPs and P functionalities of the support. Chen et al [28] reported that Pd 2+ species are stabilized by P functionalities in Pd NPs deposited on highly porous phosphorus-doped graphene sheet. The Pd 2+ species are involved in accelerating the oxidation of hydroxyl group of HFCA into aldehyde group of 5-formyl-2-furancarboxylic acid (FFCA), which is the rate-determining step in FDCA production from HMF.…”

Section: Discussionmentioning

confidence: 99%

“…Several studies have shown that the introduction of oxygen and nitrogen groups can modify the acid/base properties of carbon materials, but also improve the metal dispersion, increase the stability, and modify the electronic properties of the metal nanoparticles [11][12][13][14][15][16][17]. Beside O and N-doped carbon, recently, the effect of the introduction of P-groups on carbon surface has been an object of study in electrocatalysis [18][19][20][21][22][23][24], acetylene hydrochlorination [25], and liquid phase hydrogenation and oxidation [26][27][28]. The beneficial effect of the functionalization of activated carbon with P groups on the activity and stability of Pd nanoparticles in the hydrogenation of nitroarenes has been reported [26].…”

Section: Introductionmentioning

confidence: 99%

“…They demonstrated that embedded P atoms influence the 3 d electron density of Pd and may weaken the binding of alcohol intermediates, thus promoting the catalytic performance of Pd-P/PCF. Pd deposited on nitrogen and phosphorus-codoped graphene sheets showed better activity than Pd on unfunctionalized carbon in the oxidation of 5-hydroxymethylfurfural (HMF) to furandicarboxylic acid (FDCA) [28]. The authors showed that the functionalization of graphene with N-and P-groups increases the fraction of surface Pd 2+ species, which plays a determining role in reducing the activation energies of both HMF conversion and FDCA formation.…”

Section: Introductionmentioning

confidence: 99%

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Catalytic Performances of Au–Pt Nanoparticles on Phosphorous Functionalized Carbon Nanofibers towards HMF Oxidation

Campisi

Capelli

Motta

et al. 2018

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Herein, we reported the utilization of pre-formed Au–Pt nanoparticles deposited on phosphorus functionalized carbons as effective catalysts for the oxidation of 5-hydroxymethylfurfural (HMF) to furandicarboxylic acid (FDCA). Au–Pt nanoparticles have been prepared by a two-step methodology using polyvinyl alcohol (PVA) as protective agent and a combination of NaBH4 and H2 as reducing agents. Three carbon nanofibers (CNFs) with different graphitization degrees have been functionalized through treatment with an H3PO4–HNO3 mixture at 150 °C, in order to incorporate P groups on carbon surface. Surface and structural properties of the synthesized functionalized materials have been investigated by transmission electron microscopy (TEM), X-ray photoelectron spectroscopy (XPS), and Raman spectroscopy. The structural and surface properties of carbon nanofibers determine the amount of P-functionalities, which is a key parameter affecting the catalytic performances of Au–Pt. Indeed, the highest activity and stability has been achieved for Au–Pt deposited on the sample, which showed the largest amount of P-groups on the surface.

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Downstream Conversion of Biomass‐Derived Oxygenates to Fine Chemicals

Бессон

Loridant

Perret

et al. 2019

Chemical Catalysts for Biomass Upgrading

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Highly Porous Nitrogen- and Phosphorus-Codoped Graphene: An Outstanding Support for Pd Catalysts to Oxidize 5-Hydroxymethylfurfural into 2,5-Furandicarboxylic Acid

Cited by 63 publications

References 36 publications

The Influence of the Gold Particle Size on the Catalytic Oxidation of 5-(Hydroxymethyl)furfural

The Influence of the Gold Particle Size on the Catalytic Oxidation of 5-(Hydroxymethyl)furfural

Catalytic Performances of Au–Pt Nanoparticles on Phosphorous Functionalized Carbon Nanofibers towards HMF Oxidation

Downstream Conversion of Biomass‐Derived Oxygenates to Fine Chemicals

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