Towards Sustainable High‐Performance Thermoplastics: Synthesis, Characterization, and Enzymatic Hydrolysis of Bisguaiacol‐Based Polyesters

Curia, Silvio; Biundo, Antonino; Fischer, Isabel; Braunschmid, Verena; Gübitz, Georg; Stanzione, Joseph F.

doi:10.1002/cssc.201801059

Cited by 67 publications

(47 citation statements)

References 64 publications

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“…28 Moreover, 5Gp could serve as a novel sustainable bisphenol for the synthesis of biobased polymers. 29 Furthermore, 5Gq , 5Gr , and 5Gs were isolated in good to moderate yields (81%, 53%, and 55% respectively). When secondary amines 4t , 4u , and 4v were used as coupling partner, the corresponding tertiary amines 5Gt , 5Gu , and 5Gv were obtained in good yield.…”

Section: Resultsmentioning

confidence: 93%

From Wood to Tetrahydro-2-benzazepines in Three Waste-Free Steps: Modular Synthesis of Biologically Active Lignin-Derived Scaffolds

et al. 2019

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Inherently complex, lignin-derived aromatic monomers comprising valuable structural moieties present in many pharmaceuticals would serve as ideal substrates for the construction of biologically active molecules. Here, we describe a strategy that incorporates all intrinsic functional groups present in platform chemicals obtained by lignin depolymerization into value-added amines, using sustainable catalytic methods and benign solvents. Our strikingly efficient protocol provides access to libraries of aminoalkyl-phenol derivatives and seven-membered N-heterocycles directly from wood in two, respectively three, waste-free steps. Several molecules in these libraries have shown promising antibacterial or anticancer activities, emphasizing the advantage of this modular synthetic strategy and the potential for drug discovery. The sustainable catalytic pathways presented here can lead to significant benefits for the pharmaceutical industry where reduction of hazardous waste is a prime concern, and the described strategies that lead to high-value products from non-edible biomass waste streams also markedly increase the economic feasibility of lignocellulosic biorefineries.

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Section: Resultsmentioning

confidence: 93%

From Wood to Tetrahydro-2-benzazepines in Three Waste-Free Steps: Modular Synthesis of Biologically Active Lignin-Derived Scaffolds

et al. 2019

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“…34 Previous studies report that guaiacol was successfully reacted with formaldehyde 38,39 and involved in other polymers. 34,40 Yet, to the best of our knowledge, no study has reported the reaction with aromatic dialdehydes. Moreover, phenolic structures can be also provided from tannins 41 which are polyphenolic molecules found in all kinds of plant.…”

Section: Introductionmentioning

confidence: 99%

Toward Sustainable Phenolic Thermosets with High Thermal Performances

Granado

Tavernier

Henry

et al. 2019

ACS Sustainable Chem. Eng.

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This paper proposes more sustainable alternatives for the synthesis of high thermal performances phenolic networks. Terephthalaldehyde (TPA), a non-toxic aromatic dialdehyde, was selected to replace formaldehyde. Phenol was in turns replaced with bio-based and non-toxic phenolic building blocks: resorcinol as model for tannins, guaiacol which is easily accessible from lignin and tyrosol from olive oil mill wastewaters. The prepolymerization was performed under mild conditions (ethanol, T ≤ 100 °C). The liquid prepolymers were characterized by NMR, IR, MALDI-ToF and rheology. The curing behavior of these formulations was assessed by DSC and IR spectroscopy. An advanced isoconversional analysis of the DSC data allowed the determination of crosslinking activation energies. Furthermore, a multiple-step mechanism of TPA crosslinking was proposed with strong evidences. The thermo-mechanical properties of cured networks were characterized using DMA, showing high crosslink densities and fairly elevated glass transition temperatures. Finally, it has been proven that these new thermosets display very high thermal performances under pyrolysis conditions (TGA). TOCNew sustainable high-performance phenolic thermosets are synthesized from non-toxic and potentially biobased chemicals. We report understanding of curing mechanism and outstanding performances of networks.

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“…sugar, lignin, cinnamic acid, etc.). [22][23][24][25][26][27][28][29][30][31] Among these building blocks, furan-based ones have attracted the most attention. [32][33][34][35][36][37][38][39] Particularly, 2,5-furan-dicarboxylic acid (FDCA) has been conveniently produced from sugar resources and used to synthesize various polyesters.…”

Section: Introductionmentioning

confidence: 99%