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Synthesis and Characterization of a Low-Molecular-Weight Novolac Epoxy Derived from Lignin-Inspired Phenolics.

ABSTRACT: The need for renewable polymers capable of replacing their petrochemical counterparts continues to grow as sustainability concerns rise. Bisguaiacol (BG), a bioinspired alternative to bisphenol-A (BPA), has been synthesized using vanillyl alcohol and guaiacol via an electrophilic aromatic condensation. Purification provides both BG and an oligomeric coproduct with a consistent number average molecular weight and dispersity of ∼650 Da and ∼1.00, respectively. This coproduct has been well characterized as a low-molecular-weight novolac averaging five hydroxyls per molecule and was transformed into an epoxy resin suitable for use in thermosetting resins. The bioinspired thermoset produced in this work, consisting of the epoxidized coproduct and an amine curing agent (Epikure W), exhibited a glass transition temperature over 100 °C and glassy storage modulus value of ∼3 GPa at 25 °C. When compared to a commercial cresol novolac epoxy, the cured epoxidized coproduct resin shows comparable thermal and thermomechanical properties. When compared to a commercial BPA-based resin, the cured epoxidized coproduct resin shows improved mode 1 fracture values of 1.34 J m^1/2 (K _1C) and 448.16 J/m² (G _1C). By utilizing the coproduct strategically, the overall production of BG has the potential to become more economically feasible.

SUBMITTER: Hambleton KM

PROVIDER: S-EPMC8459366 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Project description:Increasing the resistance of plant-fermenting bacteria to lignocellulosic inhibitors is useful to understand microbial adaptation and to develop candidate strains for consolidated bioprocessing. Here, we study and improve inhibitor resistance in Clostridium phytofermentans (also called Lachnoclostridium phytofermentans), a model anaerobe that ferments lignocellulosic biomass. We survey the resistance of this bacterium to a panel of biomass inhibitors and then evolve strains that grow in increasing concentrations of the lignin phenolic, ferulic acid, by automated, long-term growth selection in an anaerobic GM3 automat. Ultimately, strains resist multiple inhibitors and grow robustly at the solubility limit of ferulate while retaining the ability to ferment cellulose. We analyze genome-wide transcription patterns during ferulate stress and genomic variants that arose along the ferulate growth selection, revealing how cells adapt to inhibitors through changes in gene dosage and regulation, membrane fatty acid structure, and the surface layer. Collectively, this study demonstrates an automated framework for in vivo directed evolution of anaerobes and gives insight into the genetic mechanisms by which bacteria survive exposure to chemical inhibitors.IMPORTANCE Fermentation of plant biomass is a key part of carbon cycling in diverse ecosystems. Further, industrial biomass fermentation may provide a renewable alternative to fossil fuels. Plants are primarily composed of lignocellulose, a matrix of polysaccharides and polyphenolic lignin. Thus, when microorganisms degrade lignocellulose to access sugars, they also release phenolic and acidic inhibitors. Here, we study how the plant-fermenting bacterium Clostridium phytofermentans resists plant inhibitors using the lignin phenolic, ferulic acid. We examine how the cell responds to abrupt ferulate stress by measuring changes in gene expression. We evolve increasingly resistant strains by automated, long-term cultivation at progressively higher ferulate concentrations and sequence their genomes to identify mutations associated with acquired ferulate resistance. Our study develops an inhibitor-resistant bacterium that ferments cellulose and provides insights into genomic evolution to resist chemical inhibitors.

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Synthesis and Characterization of a Low-Molecular-Weight Novolac Epoxy Derived from Lignin-Inspired Phenolics.

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