One‐Pot, Clean Synthesis of Vanillic Acid from Ferulic Acid

Delisi, Riccardo; Ciriminna, Rosaria; Parrino, Francesco; Palmisano, Leonardo; Xu, Yi–Jun; Pagliaro, Mario

doi:10.1002/slct.201600111

Cited by 18 publications

(15 citation statements)

References 15 publications

(13 reference statements)

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“…443 Similarly, oxidation of trans-ferulic acid embodies a complementary route to vanillin. [635][636][637] Vanillin possesses the potential to serve as a versatile platform chemical, provided that cheap vanillin will become available from future biorefineries in large quantities, either via upgrading of (iso)eugenol or through oxidative depolymerisation of lignin. Numerous polymer building blocks can be derived from vanillin, as demonstrated by Caillol et al 592,638,639 Possible vanillin transformations include the selective oxidation to vanillic acid, the partial reduction to vanillylalcohol, 640 and the reductive amination towards vanillylamine.…”

Section: Chemocatalytic Upgrading Of Phenolic Compoundsmentioning

confidence: 99%

Chemicals from lignin: an interplay of lignocellulose fractionation, depolymerisation, and upgrading

et al. 2018

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In pursuit of more sustainable and competitive biorefineries, the effective valorisation of lignin is key. An alluring opportunity is the exploitation of lignin as a resource for chemicals. Three technological biorefinery aspects will determine the realisation of a successful lignin-to-chemicals valorisation chain, namely (i) lignocellulose fractionation, (ii) lignin depolymerisation, and (iii) upgrading towards targeted chemicals. This review provides a summary and perspective of the extensive research that has been devoted to each of these three interconnected biorefinery aspects, ranging from industrially well-established techniques to the latest cutting edge innovations. To navigate the reader through the overwhelming collection of literature on each topic, distinct strategies/topics were delineated and summarised in comprehensive overview figures. Upon closer inspection, conceptual principles arise that rationalise the success of certain methodologies, and more importantly, can guide future research to further expand the portfolio of promising technologies. When targeting chemicals, a key objective during the fractionation and depolymerisation stage is to minimise lignin condensation (i.e. formation of resistive carbon-carbon linkages). During fractionation, this can be achieved by either (i) preserving the (native) lignin structure or (ii) by tolerating depolymerisation of the lignin polymer but preventing condensation through chemical quenching or physical removal of reactive intermediates. The latter strategy is also commonly applied in the lignin depolymerisation stage, while an alternative approach is to augment the relative rate of depolymerisation vs. condensation by enhancing the reactivity of the lignin structure towards depolymerisation. Finally, because depolymerised lignins often consist of a complex mixture of various compounds, upgrading of the raw product mixture through convergent transformations embodies a promising approach to decrease the complexity. This particular upgrading approach is termed funneling, and includes both chemocatalytic and biological strategies.

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Section: Chemocatalytic Upgrading Of Phenolic Compoundsmentioning

confidence: 99%

Chemicals from lignin: an interplay of lignocellulose fractionation, depolymerisation, and upgrading

et al. 2018

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“…Recently, trans-ferulic acid biotransformation employing Escherichia coli [13] bacteria [14], microbial [1,15], fungal strain [16], enzymes [5,8], etc., has also been studied. Likewise, the use of metal oxide catalysts such as inorganic materials Bi 2 WO 6 [17] or metalorganic frameworks [7,9,10] has been explored, even via photocatalytic conversion using TiO 2 [18,19], as well as WO 3 -loaded TiO 2 [20]. Biological transformations provide good vanillin yields but there are some problems related to the purification steps and the presence of remnant bacteria [13,15,20].…”

Section: Introductionmentioning

confidence: 99%

One-Pot Cu/TiO2 Nanoparticles Synthesis for Trans-Ferulic Acid Conversion into Vanillin

et al. 2019

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In this study, the co-synthesis of TiO2 and Cu metallic nanoparticles obtained via one-pot cost-efficient hydrothermal process has been addressed. Different nanocatalysts with Cu contents were characterized by X-ray diffraction, nitrogen porosimetry, scanning electron microscopy, and transmission electron microscopy. The TiO2 and Cu metallic nanoparticles were synthesized with copper loading up to one (Cu/Ti atomic ratio). Synthesized catalysts exhibited pore sizes in the mesoporous range and high surface areas above 150 m2/g. The particle size for TiO2 presented a homogeneous distribution of approximately 8 nm, moreover, Cu nanoparticles varied from 12 to >100 nm depending on the metal loading. The nanostructured materials were successfully tested in the conversion of trans-ferulic acid into vanillin under sustainable conditions, achieving the best performance for 0.3 Cu/Ti atomic ratio (70% vanillin yield).

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“…Complexity of bioconversion processes limits their use in industrial scale production . Recently Paola et al reported a photo‐catalytic route for aerobic oxidation of trans‐ferulic acid to vanillin over TiO 2 under UV irradiation, whereas Delisi et al described a similar process with higher products selectivity over Bi 2 WO 6 under dark conditions . A three‐step process for vanillin synthesis from p ‐cresol has been reported .…”

Section: Introductionmentioning

confidence: 99%

Aerobic Oxidation of Isoeugenol to Vanillin with Copper Oxide Doped Reduced Graphene Oxide

et al. 2017

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Vanillin is a high value flavor and fragrance ingredient which is mostly sourced from synthetic route with a small fraction obtained from natural vanilla. The catalytic upgrading of biomass lignin to vanillin is of interest for sustainability and economic viability of the cellulosic biorefineries. Herein, we report reduced graphene oxide supported copper oxide (CuOx/rGO) catalyzed aerobic oxidation of lignin and clove oil derived isoeugenol to vanillin. We characterized CuOx/rGO by spectroscopic (powder XRD, FTIR, XPS, Raman) technique to elucidate active sites of the catalysts. XPS and PXRD characterizations confirm the presence of nanoparticulate crystalline CuOx in the form of mixed valence CuO and Cu2O on the rGO surface. CuOx/rGO with 20% CuOx exhibits superior activity, enabling a maximum of 53% vanillin yield at mild reaction conditions. The catalyst retained comparable activity in the 4th cycle. The reasons for high activity of CuOx/rGO and a plausible mechanism involving a free‐radical pathway are elucidated.

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One‐Pot, Clean Synthesis of Vanillic Acid from Ferulic Acid

Cited by 18 publications

References 15 publications

Chemicals from lignin: an interplay of lignocellulose fractionation, depolymerisation, and upgrading

Chemicals from lignin: an interplay of lignocellulose fractionation, depolymerisation, and upgrading

One-Pot Cu/TiO2 Nanoparticles Synthesis for Trans-Ferulic Acid Conversion into Vanillin

Aerobic Oxidation of Isoeugenol to Vanillin with Copper Oxide Doped Reduced Graphene Oxide

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