Electrochemical hydrogenation reactions gained significant attention as a sustainable and efficient alternative to conventional thermocatalytic hydrogenations. This tutorial review provides a comprehensive overview of the basic principles, the practical application, and recent advances of electrochemical hydrogenation reactions, with a particular emphasis on the translation of these reactions from lab-scale to industrial applications. Giving an overview on the vast amount of conceivable organic substrates and tested catalysts, we highlight the challenges associated with upscaling electrochemical hydrogenations, such as mass transfer limitations and reactor design. Strategies and techniques for addressing these challenges are discussed, including the development of novel catalysts and the implementation of scalable and innovative cell concepts. We furthermore present an outlook on current challenges, future prospects, and research directions for achieving widespread industrial implementation of electrochemical hydrogenation reactions. This work aims to provide beginners as well as experienced electrochemists with a starting point into the potential future transformation of electrochemical hydrogenations from a laboratory curiosity to a viable technology for sustainable chemical synthesis on an industrial scale.

Developing electrochemical hydrogenation towards industrial application.

Platform molecules from lignocellulosic biomass, such as levulinic acid (LA), furfural (FF), and 5-hydroxymethylfurfural (HMF), hold great potentials as precursors to various fuels and high-value compounds through catalytic hydrogenation. However, the existing thermochemical conversions of these carbonyl-containing short-chain organics such as thermal catalytic hydrogenation involve energy-intensive and expensive processes. Electrocatalytic hydrogenation (ECH) emerges as an environmentally friendly, cost-effective, and safe process. The ECH of these organics can contribute to mitigating fossil-energy dependencies, fostering sustainable energy production, and yielding socio-economic benefits. ECH of these organics are thus intriguing, but there is a need to objectively evaluate this field. This review summarizes the product outcomes and critical reaction parameters (e.g., electrode materials, temperatures, electrolyte compositions) associated with ECH of LA, FF, and HMF. Emphasis is placed on the mechanisms related to the varying substrates. Special attention was paid to the correlations of catalytic performance with catalyst structures. After a thorough literature survey, strategies for catalyst design are discussed to enhance selectivity by promoting desired product formation and suppressing competing reactions. Moreover, current challenges, unresolved issues, and future perspectives on ECH of LA, FF, and HMF are proposed. It is expected that this work will afford useful information on the synthesis of electrocatalysts for electrochemical conversions of biomass. 

Electrochemical hydrogenation of levulinic acid, furfural and 5-hydroxymethylfurfural

Renewable biomass, with its abundant resources, provides a viable solution to address the energy crisis and mitigate environmental pollution. Furan compounds, including 5-hydroxymethylfurfural (HMF) and furfural (FF), serve as versatile... 

Electrocatalytic Conversion of Biomass-Derived Furan Compounds: Mechanisms, Catalysts and Perspectives

This study explores the potential of using spent dry batteries (SDBs) as catalysts to reduce environmental damage. The SDBs were separated into black mass (BM) and zinc rod (ZR), and the ZR material was treated with sulfuric acid to produce zinc oxide (ZO). Manganese (Mn)/ZO catalysts were synthesized with different Mn loadings and tested in the removal of o-xylene, toluene, and benzene. The results show that increasing Mn loading on ZO from 5.0 wt% to 30.0 wt% increased the catalytic decomposition of pollutants. The Mn species were well-dispersed on the ZO surface and existed in the oxidation states of Mn2+, Mn3+ and Mn4+, as confirmed by STEM/EDS and XPS, respectively. As Mn loading amount increased, the number of strong acid sites and the ratio of lattice oxygen to adsorbed oxygen (O 1sla/O 1sad) on the surface of the Mn/ZO catalyst increased, and the reduction temperature by H2 decreased. These surface properties had a significant impact on the catalytic activity. This study proposes a promising method that can contribute to both waste management and air quality improvement by recovering catalytic materials from SDBs and using them as catalysts for hydrocarbon removal. 

Performance of manganese-based catalyst comprising zinc oxide obtained from spent dry batteries for hydrocarbon oxidation

Hydrogenation is a crucial chemical process employed in a myriad of industries, often facilitated by metals such as Pd, Pt, and Ni as catalysts. Traditional thermocatalytic hydrogenation usually necessitates high temperature and elevated pressure, making the process energy intensive. Electrocatalytic hydrogenation offers an alternative but suffers from issues such as competing H2 evolution, electrolyte separation, and limited solvent selection. This Perspective introduces the evolution and advantages of the electrocatalytic Pd membrane reactor (ePMR) as a solution to these challenges. ePMR utilizes a Pd membrane to physically separate the electrochemical chamber from the hydrogenation chamber, permitting the use of water as the hydrogen source and eliminating the need for H2 gas. This setup allows for greater control over reaction conditions, such as solvent and electrolyte selection, while mitigating issues such as low Faradaic efficiency and complex product separation. Several representative hydrogenation reactions (e.g., hydrogenation of C═C, C≡C, C═O, C≡N, and O═O bonds) achieved via ePMR over the past 30 years were concisely discussed to highlight the unique advantages of ePMR. Promising research directions along with the advancement of ePMR for more challenging hydrogenation reactions are also proposed. Finally, we provide a prospect for future development of this distinctive hydrogenation strategy using hydrogen-permeable membrane electrodes. 

Electrocatalytic Hydrogenation Using Palladium Membrane Reactors

Disposal of copper, manganese and iron is particularly problematic in wastewater of metallurgical and galvanization plants, the electronics industry and agriculture. On the other hand, volatile organic compounds (VOCs), emitted from industrial processes, transportation and consumer products are the main class of air pollutants. The study revealed the potential of waste metal-loaded zeolite, generated through wastewater treatment procedures, to be utilised as an effective VOC removal catalyst for air treatment. In the first step, we have evaluated the sorption performance of natural zeolite clinoptilolite (HEU type), and synthetic zeolite 4A (LTA type) for the simultaneous removal of Cu2+, Mn2+ and Fe3+ species from aqueous solution. By a detailed sorption study, we determined the optimum sorption conditions and maximum metal concentrations in wastewater that can be after treatment disposed of in rivers or municipal plants. The efficiency of both zeolites for metal immobilization was demonstrated for concentrations up to 5 mg metals/1 g zeolite. These waste Cu-, Mn- and Fe-loaded zeolites were thermally treated at 540 °C before the second step, where we evaluated their catalytic performance in removing VOC. The thermally treated waste Cu-, Mn- and Fe-loaded natural zeolite clinoptilolite showed good catalytic performance in total toluene oxidation as a model VOC (conversion rate up to 96% at 510°C) and cycling stability (less than 15% drop in conversion rate in 4 h). In contrast, this is not the case for thermally treated waste Cu-, Mn- and Fe-loaded synthetic zeolite 4A.

/pdf/utilisation-of-waste-cu-mn-and-fe-loaded-zeolites-generated-1mwuklk0.pdf

Utilisation of waste Cu-, Mn- and Fe-loaded zeolites generated after wastewater treatment as catalysts for air treatment

Industrial hydrogenation consumes ~11 Mt of fossil-derived H2 gas yearly. Our group invented a membrane reactor to bypass the need to use H2 gas for hydrogenation chemistry. The membrane reactor sources hydrogen from water and drives reactions using renewable electricity. In this reactor, a thin piece of Pd separates an electrochemical hydrogen production compartment from a chemical hydrogenation compartment. The Pd in the membrane reactor acts as (i) a hydrogen-selective membrane, (ii) a cathode, and (iii) a catalyst for hydrogenation. Herein, we report the use of atmospheric mass spectrometry (atm-MS) and gas chromatography mass spectrometry (GC-MS) to demonstrate that an applied electrochemical bias across a Pd membrane enables efficient hydrogenation without direct H2 input in a membrane reactor. With atm-MS, we measured a hydrogen permeation of 73%, which enabled the hydrogenation of propiophenone to propylbenzene with 100% selectivity, as measured by GC-MS. In contrast to conventional electrochemical hydrogenation, which is limited to low concentrations of starting material dissolved in a protic electrolyte, the physical separation of hydrogen production from utilization in the membrane reactor enables hydrogenation in any solvent or at any concentration. The use of high concentrations and a wide range of solvents is particularly important for reactor scalability and future commercialization.

Hydrogen Production and Utilization in a Membrane Reactor.

Recently, we synthesized silver(I) complex with the antifungal agent itraconazole, which showed improved anti-Candida potential and therapeutic safety in comparison to itraconazole and rescued zebrafish embryos affected by lethal C. albicans infection, when used in safe doses. Inspired by these results, in the present study, three new silver(I) complexes with clinically used azoles, econazole (ecz), clotrimazole (ctz) and voriconazole (vcz), [Ag(ecz)2]SbF6 (Ag1), [Ag(ctz)2]SbF6 (Ag2) and {[Ag(vcz)2]SbF6}n (Ag3) were synthesized and structurally characterized by elemental microanalysis, mass spectrometry, spectroscopy (1H NMR, IR and UV-Vis), cyclic voltammetry, molar conductivity measurements, and single crystal X-ray diffraction analysis. The spectroscopic and crystallographic results revealed that, in the synthesized silver(I) complexes, azole ligands are monodentately coordinated to the Ag(I) ion through the nitrogen atom forming [Ag(azole)2]+ complex cation. The antimicrobial effect of complexes and azole ligands was evaluated against different Candida species, as well as Gram-positive and Gram-negative bacteria. The synthesized complexes Ag1-3 exhibited good to moderate antimicrobial activity being, in most cases, more active than the corresponding azole ligands. Complexes Ag2 and Ag3 also showed strong inhibitory activity against C. albicans biofilm formation and strong inhibition of C. albicans filamentation at subinhibitory concentrations. 

/pdf/silver-i-complexes-with-clinically-used-azoles-synthesis-1twz213q.pdf

Silver(I) Complexes with Clinically Used Azoles: Synthesis, Structural Characterization and Antimicrobial Evaluation

Methyltetrahydrofuran (MTHF) can be derived from non-edible biomass and used to replace diesel fuel. This work highlights the selective MTHF production from electrochemically-driven furfural hydrogenation.

Electrochemical production of methyltetrahydrofuran, a biofuel for diesel engines

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Utilisation of waste Cu-, Mn- and Fe-loaded zeolites generated after wastewater treatment as catalysts for air treatment

Hydrogen Production and Utilization in a Membrane Reactor.

Silver(I) Complexes with Clinically Used Azoles: Synthesis, Structural Characterization and Antimicrobial Evaluation

Electrochemical production of methyltetrahydrofuran, a biofuel for diesel engines