Electrochemical synthesis of biobased polymers and polymer building blocks from vanillin

Kunkel, Robin; Schmidt, Volkmar M.; Cremers, Carsten; Müller, Dominik; Schmiedl, Detlef; Tübke, Jens

doi:10.1039/d1ra00649e

Cited by 10 publications

(3 citation statements)

References 54 publications

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“…The electrocarboxylation of aldehydes using CO 2 was first studied using the test reaction of benzaldehyde to mandelic acid. The electrochemical reaction must be carried out in an aprotic solvent to avoid the reduction to benzyl alcohol and the formation of pinacol-type species (Scheme ), which are the main products in aqueous media . Voltammetric studies and electrochemical process optimization (current density, electrolyte composition, supporting electrolyte, and cathode material) were first carried out with benzaldehyde as a benchmark substrate.…”

Section: Resultsmentioning

confidence: 99%

“…The electrochemical reaction must be carried out in an aprotic solvent to avoid the reduction to benzyl alcohol and the formation of pinacol-type species (Scheme 1), which are the main products in aqueous media. 41 Voltammetric studies and electrochemical process optimization (current density, electrolyte composition, supporting electrolyte, and cathode material) were first carried out with benzaldehyde as a benchmark substrate. Thereafter, bulk electrolysis with different aldehydes and ketones were performed with the optimized electrochemical conditions.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

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Electrochemical CO₂ Utilization for the Synthesis of α-Hydroxy Acids

Seidler

Roth

Vieira

et al. 2022

ACS Sustainable Chem. Eng.

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The electrocarboxylation of organic compounds provides a green alternative to the conventional use of cyanides or organometallics. Via a simple electrochemical approach, CO 2 can be directly incorporated into aldehydes or ketones to form αhydroxy acids using electrical energy as a driving force. In this study, propylene carbonate was used as a "green" solvent. Importantly, the use of sacrificial anodes was avoided; instead, cost-efficient and stable graphite anodes were applied. Voltammetric studies on benzaldehyde carboxylation revealed that the presence of CO 2 significantly changes the reduction behavior of benzaldehyde at potentials more negative than the potential of the ketyl radical formation. Bulk electrolysis was performed in various solvents and supporting electrolyte systems, leading to more than 55% mandelic acid yield in propylene carbonate. Among the tested solvents (acetonitrile, N,N-dimethylformamide, dimethyl sulfoxide, and propylene carbonate), propylene carbonate resulted in the highest carboxylate yield. Numerous cathode materials were tested. High carboxylate yields were achieved using graphite, glassy carbon, and lead cathodes. The reaction was successfully carried out for various aromatic aldehydes and ketones as substrates, providing yields of up to 63%.

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Section: Resultsmentioning

confidence: 99%

Section: ■ Results and Discussionmentioning

confidence: 99%

Electrochemical CO₂ Utilization for the Synthesis of α-Hydroxy Acids

Seidler

Roth

Vieira

et al. 2022

ACS Sustainable Chem. Eng.

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show abstract

“…Das Fraunhofer-Institut für Chemische Technologie ICT arbeitet an der kathodischen Umsetzung von Vanillin und Vanillin-Derivaten für dimere Polymerbausteine und biobasierte Polymere. 13) Dabei entstand durch direkte kathodische Umsetzung von Vanillin das Pinakol-Produkt Hydrovanilloin in alkalisch wässriger Lösung im diskontinuierlichen Betrieb (Abbildung S. 37). Die Reaktion lässt sich nun auch in einem Durchflussreaktor durchführen.…”

Section: Grüne Wertschöpfungsketten Durch Elektrochemieunclassified

Prozesstechnik: Ein potenzieller Polymerbaustein

Schmiedl¹,

Kunkel²,

Schmidt³

2021

Nachr Chem

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Electrochemical Hydrodimerization of Lignocellulose‐Derived Carbonyls in Aqueous Electrolytes for Biobased Polymer and Long‐chained Synfuel Production: A Review

Kunkel,

Schmidt

2024

ChemSusChem

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The transformation from fossil resources, crude oil and natural gas to biomass‐derived feedstocks is an urgent and major challenge for the chemical industry. The valorization of lignocellulose as renewable resource is a promising pathway offering access to a wide range of platform chemicals, such as vanillin, furfural and 5‐HMF. The subsequent conversion of such platform chemicals is one crucial step in the value‐added chain. The electrochemical hydrodimerization (EHD) is a sustainable tool for C−C coupling of these chemicals to their corresponding hydrodimers hydrovanilloin, hydrofuroin and 5,5′‐bis(hydroxymethyl)hydrofuroin (BHH). This review covers the current state of art concerning the mechanism of the electrochemical reduction of biobased aldehydes and studies targeting the electrochemical production of these hydrodimers in aqueous media. Moreover, the subsequent conversion of these hydrodimers to valuable additives, polymers and long carbon chain synfuels will be summarized offering a broad scope for their application in the chemical industry.

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Electrochemical synthesis of biobased polymers and polymer building blocks from vanillin

Abstract: Hydrovanilloin and polyvanillin were synthesized electrochemically investigating the impact of process parameters such as electrode material, charge and current density.

Cited by 10 publications

References 54 publications

Electrochemical CO₂ Utilization for the Synthesis of α-Hydroxy Acids

Electrochemical CO₂ Utilization for the Synthesis of α-Hydroxy Acids

Prozesstechnik: Ein potenzieller Polymerbaustein

Electrochemical Hydrodimerization of Lignocellulose‐Derived Carbonyls in Aqueous Electrolytes for Biobased Polymer and Long‐chained Synfuel Production: A Review

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Electrochemical synthesis of biobased polymers and polymer building blocks from vanillin

Abstract: Hydrovanilloin and polyvanillin were synthesized electrochemically investigating the impact of process parameters such as electrode material, charge and current density.

Cited by 10 publications

References 54 publications

Electrochemical CO2 Utilization for the Synthesis of α-Hydroxy Acids

Electrochemical CO2 Utilization for the Synthesis of α-Hydroxy Acids

Prozesstechnik: Ein potenzieller Polymerbaustein

Electrochemical Hydrodimerization of Lignocellulose‐Derived Carbonyls in Aqueous Electrolytes for Biobased Polymer and Long‐chained Synfuel Production: A Review

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Electrochemical CO₂ Utilization for the Synthesis of α-Hydroxy Acids

Electrochemical CO₂ Utilization for the Synthesis of α-Hydroxy Acids