Catalytic Scissoring of Lignin into Aryl Monomers

Wang, Min; Wang, Rui

doi:10.1002/adma.201901866

Cited by 140 publications

(92 citation statements)

References 171 publications

(206 reference statements)

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“…[5b, 7] Despite these efforts,t he electrochemical oxidation of lignin-derived products via oxidative C(OH) À Cb onds cleavage is underexplored possibly due to its high binding dissociation energy (260-300 kJ mol À1 ). [8] Herein we report an electrochemical oxidation strategy for selective upgrading of lignin-derived secondary alcohols or ketones into carboxylates over aM nCoOOH catalyst integrated with water splitting (Scheme 1c). TheMnCoOOH catalyst shows good generality to various secondary alcohols and ketones to corresponding carboxylates in satisfactory yield (64-99 %) and excellent operational stability (200 h) at room temperature without external oxidant.…”

Section: Introductionmentioning

confidence: 99%

Selectively Upgrading Lignin Derivatives to Carboxylates through Electrochemical Oxidative C(OH)−C Bond Cleavage by a Mn‐Doped Cobalt Oxyhydroxide Catalyst

Zhou

et al. 2021

Angewandte Chemie

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Oxidative cleavage of C(OH)ÀCb onds to afford carboxylates is of significant importance for the petrochemical industry and biomass valorization. Here we report an efficient electrochemical strategy for the selective upgrading of lignin derivatives to carboxylates by am anganese-doped cobalt oxyhydroxide (MnCoOOH) catalyst. Awide range of ligninderived substrates with C(OH)-C or C(O)-C units undergo efficient cleavage to corresponding carboxylates in excellent yields (80-99 %) and operational stability (200 h). Detailed investigations reveal atandem oxidation mechanism that base from the electrolyte converts secondary alcohols and their derived ketones to reactive nucleophiles,which are oxidized by electrophilic oxygen species on MnCoOOH from water.A s proof of concept, this approachwas applied to upgrade lignin derivatives with C(OH)-C or C(O)-C motifs,a chieving convergent transformation of lignin-derived mixtures to benzoate and KA oil to adipate with 91.5 %a nd 64.2 %y ields, respectively.

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Section: Introductionmentioning

confidence: 99%

Selectively Upgrading Lignin Derivatives to Carboxylates through Electrochemical Oxidative C(OH)−C Bond Cleavage by a Mn‐Doped Cobalt Oxyhydroxide Catalyst

Zhou

et al. 2021

Angewandte Chemie

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“…[154] Various methods have been introduced to depolymerize lignin through chemical, electrolysis and bio-logical means. [27,87,151,[155][156][157][158][159] Energy conversion from lignocellulosic biomass into electricity using bioelectrochemical methods, such as microbial fuel cells (MFCs), [160] microbial electrolysis cells (MECs), [154,161] and electro-microbial system (EMS) [156] have also been developed. In these studies, the feasibility of using lignin as a substrate to the MFC for electricity generation with the simultaneous accomplishment of lignin conversion has been demonstrated.…”

Section: Microbial Electrolysismentioning

confidence: 99%

Electrochemical Lignin Conversion

et al. 2020

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Lignin is the largest source of renewable aromatic compounds, making the recovery of aromatic compounds from this material a significant scientific goal. Recently, many studies have reported on lignin depolymerization and upgrading strategies. Electrochemical approaches are considered to be low cost, reagent free, and environmentally friendly, and can be carried out under mild reaction conditions. In this Review, different electrochemical lignin conversion strategies, including electrooxidation, electroreduction, hybrid electro‐oxidation and reduction, and combinations of electrochemical and other processes (e. g., biological, solar) for lignin depolymerization and upgrading are discussed in detail. In addition to lignin conversion, electrochemical lignin fractionation from biomass and black liquor is also briefly discussed. Finally, the outlook and challenges for electrochemical lignin conversion are presented.

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“…described a one‐pot, dual photocatalyst, dual wavelength protocol to sequentially oxidize and hydrogenolyze lignin model compounds to produce mono‐aromatic products (Figure a) . Through DFT calculations, they estimated that the C−O bond at the β‐O‐4 linkage would drop dramatically by over 80 kJ mol −1 if the benzylic alcohol was first oxidized to a ketone . Thus, they developed a Pd/ZnIn 2 S 4 photocatalyst that could effect the aerobic oxidation of benzylic alcohols with 455 nm irradiation (left part in Figure a) .…”

Section: Pecs For Biomass Valorizationmentioning

confidence: 99%

Photoelectrochemical Cells for Artificial Photosynthesis: Alternatives to Water Oxidation

Boruah

Chin

et al. 2020

ChemNanoMat

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Photoelectrochemical cells have been used as one of the most common artificial photosynthetic approaches to mimic natural photosynthetic water splitting reactions. However, despite the tremendous advances made to improve the affordability and efficiency of photoelectrochemical water splitting, it is still not an economically feasible method to produce solar fuels currently since only the H 2 evolving reduction half-reaction generates valuable fuels. Therefore, in this review, we intend to highlight other underexplored substrates and reactions for producing solar fuels in photo-electrochemical cells, as well as alternative architectures including temporally independent and biohybrid systems. We show that besides water oxidation, electrocatalytic or photoredox reactions for pollutant degradation, biomass valorization, and organic chemical synthesis can be or have been successfully adapted for photoelectrochemical cells, thus offering a virtually infinite number of possibilities for artificial photosynthetic applications which generate valuable products in both the reduction and oxidation half reactions.

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Catalytic Scissoring of Lignin into Aryl Monomers

Cited by 140 publications

References 171 publications

Selectively Upgrading Lignin Derivatives to Carboxylates through Electrochemical Oxidative C(OH)−C Bond Cleavage by a Mn‐Doped Cobalt Oxyhydroxide Catalyst

Selectively Upgrading Lignin Derivatives to Carboxylates through Electrochemical Oxidative C(OH)−C Bond Cleavage by a Mn‐Doped Cobalt Oxyhydroxide Catalyst

Electrochemical Lignin Conversion

Photoelectrochemical Cells for Artificial Photosynthesis: Alternatives to Water Oxidation

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