Diverse Applications of Biomass‐Derived 5‐Hydroxymethylfurfural and Derivatives as Renewable Starting Materials

Chacón-Huete, Franklin; Messina, Cynthia; Cigana, Brandon; Forgione, Pat

doi:10.1002/cssc.202200328

Cited by 32 publications

(20 citation statements)

References 111 publications

(305 reference statements)

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“…Among them, monosaccharides such as glucose, fructose, and xylose can be dehydrated to furnish a key platform chemical 5-hydroxymethylfurfural (5-HMF) . The catalytic transformation of biomass to 5-HMF plays a significant role in the biochemical industry, since this furan-containing substance is the feedstock of multiple downstream products . For instance, 2,5-furandicarboxylic acid (FDCA) and 2,5-dihydroxymethylfuran (DHMF), C6 compounds readily produced from 5-HMF, hold promising future in the polymer industry owing to their huge potential as bifunctional monomers.…”

Section: Introductionmentioning

confidence: 99%

“…7 The catalytic transformation of biomass to 5-HMF plays a significant role in the biochemical industry, since this furancontaining substance is the feedstock of multiple downstream products. 8 For instance, 2,5-furandicarboxylic acid (FDCA) 9 and 2,5-dihydroxymethylfuran (DHMF), 10 C6 compounds readily produced from 5-HMF, hold promising future in the polymer industry owing to their huge potential as bifunctional monomers. Moreover, furan-based polymers derived from FDCA and/or DHMF have attracted tremendous attention worldwide due to their widespread application in the foreseeable future.…”

Section: ■ Introductionmentioning

confidence: 99%

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Recyclable Biomass-Derived Polyethylene-Like Materials as Functional Coatings for Commercial Fabrics: Toward Upcycling of Waste Textiles

Qin

Gan

et al. 2022

ACS Sustainable Chem. Eng.

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Bio-based polymers are recognized as promising alternatives to fossil-based counterparts. However, the inferior material performance of bio-based polymers is a serious restriction to their application fields. Herein, renewable polyethylene-like materials (PLMs) are used as surface coatings for commercial fabrics. First, α,ω-diene monomers were synthesized by the downstream products of sugar and castor oil derivatives. Subsequently, biomass-derived polymers were generated via acyclic diene metathesis (ADMET) (co)polymerization of these monomers followed by exhaustive hydrogenation. The obtained long-chain aliphatic polyesters are considered remarkable polyethylene mimics in that these hydrophobic and semicrystalline materials show unique features such as hydrolysis resistance and recyclability. On the other hand, PLM nanoparticles were prepared by the nanoprecipitation method and then drop-cast on commercial fabric surfaces. Hydrophobically modified fabrics show repellency to various water droplets and the capability of oil/water separation as well as anti-icing and anticorrosive characteristics. Moreover, photoinduced contaminant removal and wettability change are realized by fabrics with a hybrid coating layer composed of PLM and titanium dioxide (TiO 2 ) nanoparticles. These polyethylene-mimetic materials not only meet the requirements of sustainability in terms of renewability and recyclability but also show great prospects in surface functionalization of commercial fabrics and upcycling of waste textiles.

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Section: Introductionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

Recyclable Biomass-Derived Polyethylene-Like Materials as Functional Coatings for Commercial Fabrics: Toward Upcycling of Waste Textiles

Qin

Gan

et al. 2022

ACS Sustainable Chem. Eng.

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“…The use of BPA poses major health concerns as it is suspected of affecting the human endocrine system; thus, less toxic alternative compounds are highly desirable. [ 58 ]…”

Section: Resultsmentioning

confidence: 99%

“…The use of BPA poses major health concerns as it is suspected of affecting the human endocrine system; thus, less toxic alternative compounds are highly desirable. [58] Dimethyl 5,5′-oxybis(methylene)bis(furan-5,2-diyl)bis(methylene) dicarbonate (OBMF-DC), the methoxycarbonyl derivative of OBMF-H, was then synthesized by reaction of the OBMF-derived diol with DMC, used as solvent and reagent, in the presence of potassium carbonate. A Dean-Stark apparatus was utilized to push the thermodynamically driven reaction (B Ac 2 mechanism) toward the desired product that was isolated in quantitative yield as a pure crystalline white solid after filtering off the base and evaporating the exceeding DMC.…”

Section: Obmf Upgrading and Thermal Degradation Studiesmentioning

confidence: 99%

A Green Synthesis of 5,5′‐[Oxybis(methylene)]bis‐2‐Furfural: from By‐Product to Attractive Bio‐Based Platform Chemical

Annatelli

Trapasso

Torre

et al. 2022

Advanced Sustainable Systems

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lignin-derived monomers, fatty acids, aliphatic alkanes/alkenes or aromatics/ phenolic, vegetable oils, terpenes, C5-C6 sugars, and their furan-based derivatives.Among these biomolecules, 5-(hydroxymethyl)furfural (HMF) -first reported in 1895 -has quickly become the archetype of bio-based platform chemicals. [4][5][6][7][8] HMF is a versatile molecule with a wide range of potential applications in pharmaceuticals, [9,10] biofuels, [11][12][13] biopolymers, [14][15][16] and surfactants. [17] On the other hand, HMF also encompasses some issues such as i) the absence of a cost-efficient scale-up synthesis (currently cost being 960 € kg −1 ), [18] ii) a hydrophilic and polar behavior that prevents its recovery from aqueous media, and iii) a fast degradation due to the formation of dimers, oligomers, and humin during storage. The latter drawback has been partially solved with the addition of a small amount of stabilizer. [19] In fact, it is known that the typical dehydration conditions employed for the HMF synthesis, promote numerous secondary reactions such as (self-) etherification, esterification, aldol condensation, acetalization, and, of course, humin formation. [20] Among these by-products, 5,5′-[oxybis(methylene)]bis-2-furfural (OBMF), detected both during HMF synthesis and as a result of its spontaneous degenerative process, is indeed an interesting compound. [21] To date, OBMF has been only scarcely reported in the literature despite the fact that the first synthetic procedures to this molecule dated back to the end of the XX century. [21][22][23][24] Only in recent years, the interest in OBMF has considerably risen due to its exploitation in the synthesis of macrocycles (16-crown-6), [25] and, most importantly, as a precursor of polyurethanes, polyamides, and polyamines. [26] Table 1 and Figure 1 report an overview of the main synthetic procedures for OBMF available in the literature. Several homogeneous and heterogeneous catalysts were employed.One of the first methodologies reported was the HMF selfetherification reaction (#1, 2, 7; Table 1) generally promoted by acids such as p-toluenesulfonic acid (PTSA), in non-polar organic solvents, that is, benzene, toluene or xylene. This approach was conducted also on a gram-scale, leading OBMF with a yield of up to 76%. [22,27,28] In another less efficient approach, OBMF achieved in 55% yield by thermal dehydration of HMF in dimethyl sulfoxide (DMSO), (#3; Table 1). [23] In this work, a green synthetic approach to 5,5′-[oxybis(methylene)]bis-2-furfural (OBMF) from 5-hydroxymethyl-2-furfural (HMF) is reported for the first time. In the optimized reaction conditions, dimethyl carbonate (DMC) is used as the preferred green solvent and iron(III) sulfate as the best catalyst, recyclable up to three times. The HMF self-etherification reaction is conducted both in milligram-and gram-scale with isolated yields up to 99% and 81% respectively. OBMF is further derivatized via reduction to achieve 5,5′-oxybis(methylene)bis(furan-5,2-diyl)dimethanol (OBMF-H), a potential bis...

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“…Nanomaterials have been of wide interest to scientific researchers due to their unique electrical, magnetic, optical, mechanical, and structural properties . Hence, they have versatile applications in electronics, medicine, aviation, chemical industry, and so forth. Nanomaterials have also been applied as sensors over the years for the adsorption of prominent poisonous gases and also for drug delivery .…”

Section: Introductionmentioning

confidence: 99%

Probing the Reactions of Thiourea (CH₄N₂S) with Metals (X = Au, Hf, Hg, Ir, Os, W, Pt, and Re) Anchored on Fullerene Surfaces (C₅₉X)

et al. 2022

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Upon various investigations conducted in search for a nanosensor material with the best sensing performance, the need to explore these materials cannot be overemphasized as materials associated with best sensing attributes are of vast interest to researchers. Hence, there is a need to investigate the adsorption performances of various metal-doped fullerene surfaces: C 59 Au, C 59 Hf, C 59 Hg, C 59 Ir, C 59 Os, C 59 Pt, C 59 Re, and C 59 W on thiourea [SC(NH 2 ) 2 ] molecule using first-principles density functional theory computation. Comparative adsorption study has been carried out on various adsorption models of four functionals, M06-2X, M062X-D3, PBE0-D3, and ωB97XD, and two double-hybrid (DH) functionals, DSDPBEP86 and PBE0DH, as reference at Gen/def2svp/LanL2DZ. The visual study of weak interactions such as quantum theory of atoms in molecule analysis and noncovalent interaction analysis has been invoked to ascertain these results, and hence we arrived at a conclusive scientific report. In all cases, the weak adsorption observed is best described as physisorption phenomena, and CH 4 N 2 S@C 59 Pt complex exhibits better sensing attributes than its studied counterparts in the interactions between thiourea molecule and transition metal-doped fullerene surfaces. Also, in the comparative adsorption study, DH density functionals show better performance in estimating the adsorption energies due to their reduced mean absolute deviation (MAD) and root-mean-square deviation (RMSD) values of (MAD = 1.0305, RMSD = 1.6277) and (MAD = 0.9965, RMSD = 1.6101) in DSDPBEP86 and PBE0DH, respectively.

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Diverse Applications of Biomass‐Derived 5‐Hydroxymethylfurfural and Derivatives as Renewable Starting Materials

Cited by 32 publications

References 111 publications

Recyclable Biomass-Derived Polyethylene-Like Materials as Functional Coatings for Commercial Fabrics: Toward Upcycling of Waste Textiles

Recyclable Biomass-Derived Polyethylene-Like Materials as Functional Coatings for Commercial Fabrics: Toward Upcycling of Waste Textiles

A Green Synthesis of 5,5′‐[Oxybis(methylene)]bis‐2‐Furfural: from By‐Product to Attractive Bio‐Based Platform Chemical

Probing the Reactions of Thiourea (CH₄N₂S) with Metals (X = Au, Hf, Hg, Ir, Os, W, Pt, and Re) Anchored on Fullerene Surfaces (C₅₉X)

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Diverse Applications of Biomass‐Derived 5‐Hydroxymethylfurfural and Derivatives as Renewable Starting Materials

Cited by 32 publications

References 111 publications

Recyclable Biomass-Derived Polyethylene-Like Materials as Functional Coatings for Commercial Fabrics: Toward Upcycling of Waste Textiles

Recyclable Biomass-Derived Polyethylene-Like Materials as Functional Coatings for Commercial Fabrics: Toward Upcycling of Waste Textiles

A Green Synthesis of 5,5′‐[Oxybis(methylene)]bis‐2‐Furfural: from By‐Product to Attractive Bio‐Based Platform Chemical

Probing the Reactions of Thiourea (CH4N2S) with Metals (X = Au, Hf, Hg, Ir, Os, W, Pt, and Re) Anchored on Fullerene Surfaces (C59X)

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Probing the Reactions of Thiourea (CH₄N₂S) with Metals (X = Au, Hf, Hg, Ir, Os, W, Pt, and Re) Anchored on Fullerene Surfaces (C₅₉X)