From vanillin to biobased aromatic polymers

Qiang, Hongru; Wang, Jiewen; Liu, Hengxu; Zhu, Yunqing

doi:10.1039/d3py00767g

Cited by 23 publications

(4 citation statements)

References 126 publications

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“…Among these products, the 2-methoxy-4-methylphenol (MMP) product could be potentially employed as an intermediate in spices, pharmaceuticals and other organic synthesis. 6–9 Therefore, in the past few decades tremendous efforts have been devoted to the design and preparation of efficient hydrodeoxygenation catalysts for a high selectivity conversion of VAN to obtain MMP. For example, Ashish Kumar Kar et al designed a series of defect-induced UIO-66 MOF and MoO 3 decorated Co-BTC MOF catalysts for employment in VAN hydrodeoxygenation.…”

Section: Introductionmentioning

confidence: 99%

Environmentally-friendly preparation of natural hollow carbon spheres derived from a biomass puffball for in situ upgrading of lignin-derived vanillin

Chen,

Ji,

Xiong

et al. 2024

Green Chem.

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Section: Introductionmentioning

confidence: 99%

Environmentally-friendly preparation of natural hollow carbon spheres derived from a biomass puffball for in situ upgrading of lignin-derived vanillin

Chen,

Ji,

Xiong

et al. 2024

Green Chem.

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“…Also, due to the fast kinetics of the exchange reactions taking place in the network, self-healing behavior and fast stress relaxation has been observed in this class of CANs . In addition, the biobased pool of aldehydes is rather extensive, and includes vanillin, − syringaldehyde, , furfural, − and functionalized lignin. − Imine formation is a well-known reaction in which a primary amine reacts with an aldehyde, yielding a CN moiety, with water as the sole byproduct . Taken together, imine-based CANs represent a promising platform as a substituent for nonrenewable materials since dynamic covalent chemistries allow closed-loop recyclability .…”

Section: Introductionmentioning

confidence: 99%

Covalent Adaptable Networks with Tailorable Material Properties Based on Divanillin Polyimines

Fanjul-Mosteirín,

Odelius

2024

Biomacromolecules

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Covalent adaptable networks (CANs) are being developed as future replacements for thermosets as they can retain the high mechanical and chemical robustness inherent to thermosets but also integrate the possibility of reprocessing after material use. Here, covalent adaptable polyimine-based networks were designed with methoxy and allyloxy-substituted divanillin as a core component together with long flexible aliphatic fatty acid-based amines and a short rigid chain triamine, yielding CANs with a high renewable content. The designed series of CANs with reversible imine functionality allowed for fast stress relaxation and tailorability of the thermomechanical properties, as a result of the ratio between long flexible and short rigid amines, with tensile strength (σ b ) ranging 1.07−18.7 MPa and glass transition temperatures ranging 16−61 °C. The CANs were subsequently successfully reprocessed up to three times without determinantal structure alterations and retained mechanical performance. The CANs were also successfully chemically recycled under acidic conditions, where the starting divanillin monomer was recovered and utilized for the synthesis of a recycled CAN with similar thermal and mechanical properties. This promising class of thermosets bearing sustainable dynamic functionalities opens a window of opportunity for the progressive replacement of fossil-based thermosets.

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“…From a chemical point of view, vanillin can be classified as a bifunctional aromatic compound since it bears two reactive groups, namely the aldehyde and the phenol groups, that can be used for the synthesis of several second-generation vanillin-derived chemicals. Additionally, these compounds can be exploited as building-block monomers for preparing polymeric materials with tuned properties for tailored applications, including coatings, adhesives, elastomers, and optoelectronic materials [14]. For these reasons, vanillin has the potential to be a renewable building block in the cutting-edge chemical industry.…”

Section: Introductionmentioning

confidence: 99%

Integrated Approach of Life Cycle Assessment and Experimental Design in the Study of a Model Organic Reaction: New Perspectives in Renewable Vanillin-Derived Chemicals

Ruini,

Ferrari,

Durante

et al. 2024

Molecules

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This work is focused on performing a quantitative assessment of the environmental impacts associated with an organic synthesis reaction, optimized using an experimental design approach. A nucleophilic substitution reaction was selected, employing vanillin as the substrate, a phenolic compound widely used in the food industry and of pharmaceutical interest, considering its antioxidant and antitumoral potential. To carry out the reaction, three different solvents have been chosen, namely acetonitrile (ACN), acetone (Ace), and dimethylformamide (DMF). The syntheses were planned with the aid of a multivariate experimental design to estimate the best reaction conditions, which simultaneously allow a high product yield and a reduced environmental impact as computed by Life Cycle Assessment (LCA) methodology. The experimental results highlighted that the reactions carried out in DMF resulted in higher yields with respect to ACN and Ace; these reactions were also the ones with lower environmental impacts. The multilinear regression models allowed us to identify the optimal experimental conditions able to guarantee the highest reaction yields and lowest environmental impacts for the studied reaction. The identified optimal experimental conditions were also validated by experimentally conducting the reaction in those conditions, which indeed led to the highest yield (i.e., 93%) and the lowest environmental impacts among the performed experiments. This work proposes, for the first time, an integrated approach of DoE and LCA applied to an organic reaction with the aim of considering both conventional metrics, such as reaction yield, and unconventional ones, such as environmental impacts, during its lab-scale optimization.

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From vanillin to biobased aromatic polymers

Abstract: Aromatic compounds are platform chemicals used in the manufacture of commodity polymers. The development of bio-based aromatic compounds is expected to reduce the dependence on non-renewable resources. Lignin is the...

Cited by 23 publications

References 126 publications

Environmentally-friendly preparation of natural hollow carbon spheres derived from a biomass puffball for in situ upgrading of lignin-derived vanillin

Environmentally-friendly preparation of natural hollow carbon spheres derived from a biomass puffball for in situ upgrading of lignin-derived vanillin

Covalent Adaptable Networks with Tailorable Material Properties Based on Divanillin Polyimines

Integrated Approach of Life Cycle Assessment and Experimental Design in the Study of a Model Organic Reaction: New Perspectives in Renewable Vanillin-Derived Chemicals

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