Advances in polymer precursors and bio‐based polymers synthesized from 5‐hydroxymethylfurfural

Zhang, Daihui; Dumont, Marie‐Josée

doi:10.1002/pola.28527

Cited by 110 publications

(86 citation statements)

References 209 publications

(359 reference statements)

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“…It is easily obtained from C 6 sugars such as fructose, glucose, and cellulose by dehydration . In addition, its rich chemistry makes it valuable for synthesizing a range of compounds, including polymer platforms . Representative HMF‐derived polymer platforms are 2,5‐furandicarboxylic acid (FDCA) and 2,5‐bis(hydroxymethyl)furan (BHMF).…”

Section: Introductionmentioning

confidence: 99%

“…2 In addition, its rich chemistry makes it valuable for synthesizing a range of compounds, including polymer platforms. [3][4][5] Representative HMF-derived polymer platforms are 2,5-furandicarboxylic acid (FDCA) and 2,5-bis (hydroxymethyl)furan (BHMF). FDCA has been used as a substitute for petrochemical-derived terephthalic acid and for fabricating sustainable polyesters, 6,7 whereas BHMF has been used for fabricating eco-friendly polyesters.…”

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confidence: 99%

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Biomass‐derived furanic polycarbonates: Mild synthesis and control of the glass transition temperature

Choi

Lee

Son

et al. 2019

J. Polym. Sci. Part A: Polym. Chem.

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Bis(hydroxymethyl)furan (BHMF) is a promising biomass‐derived polymer platform, but it is incompatible with traditional methods used for synthesizing polycarbonates (PCs) owing to its thermal instability. In this study, BHMF‐based furanic (FR) PCs were prepared successfully at a relatively low temperature through the mediation of carbonyldiimidazole. The low Tg of aliphatic FR‐PCs was controlled elaborately, exploiting the reactivity of furan in the Diels–Alder reactions and the molecular rigidity of the resulting oxabicycles. © 2019 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2019, 57, 1796–1800

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Section: Introductionmentioning

confidence: 99%

mentioning

confidence: 99%

Biomass‐derived furanic polycarbonates: Mild synthesis and control of the glass transition temperature

Choi

Lee

Son

et al. 2019

J. Polym. Sci. Part A: Polym. Chem.

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“…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.…”

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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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“…Monomer and polymer production from renewable feedstocks has become a relevant research target with the aim of providing more environmental friendly solutions to the actual fossil-based market [1][2][3][4][5][6]. In this framework, 5-(hydroxymethyl)furfural (HMF) is recognized as an ideal platform molecule to develop different green products, since it can be obtained via acid-catalyzed dehydration of biomass-derived sugars [7][8][9], and, in turn, it can be converted into a wide range of different high added value chemicals [10][11][12][13]. Among the HMF products, 2,5-furandicarboxylic acid (FDCA, Scheme 1) has been identified as one of the most interesting [14], since it can be considered as the bioderived counterpart of terephthalic acid for the production of polyesters [15], such as polyethylene 2,5-furandicarboxylate First attempts to industrially convert HMF to FDCA relied on the technologies developed for terephthalic acid production [18].…”

Section: Introductionmentioning

confidence: 99%

Pd/Au Based Catalyst Immobilization in Polymeric Nanofibrous Membranes via Electrospinning for the Selective Oxidation of 5-Hydroxymethylfurfural

et al. 2020

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Innovative nanofibrous membranes based on Pd/Au catalysts immobilized via electrospinning onto different polymers were engineered and tested in the selective oxidation of 5-(hydroxymethyl)furfural in an aqueous phase. The type of polymer and the method used to insert the active phases in the membrane were demonstrated to have a significant effect on catalytic performance. The hydrophilicity and the glass transition temperature of the polymeric component are key factors for producing active and selective materials. Nylon-based membranes loaded with unsupported metal nanoparticles were demonstrated to be more efficient than polyacrylonitrile-based membranes, displaying good stability and leading to high yield in 2,5-furandicarboxylic acid. These results underline the promising potential of large-scale applications of electrospinning for the preparation of catalytic nanofibrous membranes to be used in processes for the conversion of renewable molecules.

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Advances in polymer precursors and bio‐based polymers synthesized from 5‐hydroxymethylfurfural

Cited by 110 publications

References 209 publications

Biomass‐derived furanic polycarbonates: Mild synthesis and control of the glass transition temperature

Biomass‐derived furanic polycarbonates: Mild synthesis and control of the glass transition temperature

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

Pd/Au Based Catalyst Immobilization in Polymeric Nanofibrous Membranes via Electrospinning for the Selective Oxidation of 5-Hydroxymethylfurfural

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