Mechanocatalytic hydrogenolysis of benzyl phenyl ether over supported nickel catalysts

Tricker, Andrew W.; Najmi, Sean; Phillips, Erin V.; Hebisch, Karoline L.; Kang, Jason X.; Sievers, Carsten

doi:10.1039/d2su00089j

Cited by 4 publications

(6 citation statements)

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“…The final alkane products form through the combination of produced alkyl radicals and atomic hydrogens over metallic surfaces which usually accounts for H 2 dissociation in thermal catalytic hydrogenation reactions 42 , 43 . H 2 dissociation by mechanocatalysis should be feasible, on account of the reported work of ammonia synthesis 21 – 23 and hydrogenolysis of benzyl phenyl ether 44 under ambient hydrogen pressure, where H 2 dissociation is indispensable. Moreover, hydrogen dissociation also occurs on the metals used even without mechanical forces.…”

Section: Resultsmentioning

confidence: 99%

Hydrogenation of different carbon substrates into light hydrocarbons by ball milling

Li,

Vozniuk,

Cao

et al. 2023

Nat Commun

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The conversion of carbon-based solids, like non-recyclable plastics, biomass, and coal, into small molecules appears attractive from different points of view. However, the strong carbon–carbon bonds in these substances pose a severe obstacle, and thus—if such reactions are possible at all—high temperatures are required1–5. The Bergius process for coal conversion to hydrocarbons requires temperatures above 450 °C6, pyrolysis of different polymers to pyrolysis oil is also typically carried out at similar temperatures7,8. We have now discovered that efficient hydrogenation of different solid substrates with the carbon-based backbone to light hydrocarbons can be achieved at room temperature by ball milling. This mechanocatalytic method is surprisingly effective for a broad range of different carbon substrates, including even diamond. The reaction is found to proceed via a radical mechanism, as demonstrated by reactions in the presence of radical scavengers. This finding also adds to the currently limited knowledge in understanding mechanisms of reactions induced by ball milling. The results, guided by the insight into the mechanism, could induce more extended exploration to broaden the application scope and help to address the problem of plastic waste by a mechanocatalytic approach.

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Section: Resultsmentioning

confidence: 99%

Hydrogenation of different carbon substrates into light hydrocarbons by ball milling

Li,

Vozniuk,

Cao

et al. 2023

Nat Commun

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“…[1] About one-third of global CO 2 emissions come from industrial processes (≈26%) and heavy-duty transportation (≈8%), [1][2][3] which are particularly difficult to decarbonize. Green hydrogen can play a unique role in achieving net zero for these sectors, [4] either as storage/carrier of renewable energy (e.g., fuel for freight transportation or industrial process heat), [5][6][7][8] as a replacement to fossil hydrogen (e.g., in petro/bio-refining or ammonia production), [9][10][11][12][13] or as an alternative chemical reagent (e.g., metal refining). [14] For this reason, the International Energy Agency has projected that the global usage of hydrogen will increase from 90 to 500 Mtpa (million tonnes per annum) to reach net zero by 2050.…”

Section: Introductionmentioning

confidence: 99%

Pathways Toward Efficient and Durable Anion Exchange Membrane Water Electrolyzers Enabled By Electro‐Active Porous Transport Layers

Tricker,

Ertugrul,

Lee

et al. 2023

Advanced Energy Materials

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Green hydrogen, produced via water electrolysis using renewable electricity, will play a crucial role in decarbonizing industrial and heavy‐duty transportation sectors. Anion exchange membrane water electrolyzers (AEMWEs) can overcome many of the performance and cost limitations of incumbent technologies, however, still suffer from durability challenges due to oxidative instability of anion‐exchange ionomers. Herein, the use of an electro‐active porous transport layer as anode (PTL‐electrode) is demonstrated to enable efficient and durable AEMWEs. The stainless‐steel PTL‐electrodes are shown to have superior performance and durability compared to traditional catalyst layers containing ionomer and nanoparticle catalysts. An AEMWE cell operating at 2 A cm−2 for over 600 h exhibited a degradation rate of just 5 µV h−1. During operation, the surface composition of the stainless steel transforms into a mixture of iron and nickel oxyhydroxides, contributing to enhanced oxygen‐evolution reaction activity. The combination of experimental work and modeling elucidates how the bulk structure of the PTL‐electrode offers an additional design dimension to further improve electrolyzer performance. Lastly, a surface modification strategy is applied to a PTL‐electrode to achieve an even higher performing AEMWE (2.3 vs 2.0 A cm−2 at 1.8 V). Overall, this work lays out pathways toward more efficient, durable, and affordable AEMWEs.

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“…Several studies of mechanocatalysis as an approach to depolymerizing lignocellulosic biomass and lignin model compounds have been conducted. ,,− Rinaldi et al demonstrated the depolymerization of both cellulose and biomass to water-soluble sugars and furfurals with complete conversion and yields of water-soluble oligosaccharides and lignin oligomers exceeding 90%. − Bolm’s works have examined the conversion of lignin model compounds representing β-O-4 linkages in base-catalyzed and oxidative reactions . The base-catalyzed reactions produced monomer yields of up to 94%, while the oxidative transformation resulted in aryl-c α cleavage of the β-O-4 model, resulting in quinone (91% yield) and guaiacol (82% yield) as the two main products.…”

mentioning

confidence: 99%

“…The base-catalyzed reactions produced monomer yields of up to 94%, while the oxidative transformation resulted in aryl-c α cleavage of the β-O-4 model, resulting in quinone (91% yield) and guaiacol (82% yield) as the two main products. Sievers et al recently demonstrated hydrogenolysis of the α-O-4 bond in the lignin model compound, benzyl phenyl ether (BPE), over supported Ni catalysts . Due to the similar bond strengths, this ether bond can be considered representative of the β-O-4 linkages found in lignin.…”

mentioning

confidence: 99%

Mechanocatalytic Hydrogenolysis of the Lignin Model Dimer Benzyl Phenyl Ether over Supported Palladium Catalysts

Phillips,

Tricker,

Stavitski

et al. 2024

ACS Sustainable Chem. Eng.

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This work demonstrates the mechanocatalytic hydrogenolysis of the ether bond in the lignin model compound benzyl phenyl ether (BPE) and hardwood lignin isolated by hydrolysis with supercritical water. Pd catalysts with 4 wt % loading on Al 2 O 3 and SiO 2 supports achieve 100% conversion of BPE with a toluene production rate of (2.6−2.9) × 10 −5 mol•min −1 . The formation of palladium hydrides under H 2 gas flow contributes to an increase in the turnover frequency by a factor of up to 300 compared to Ni on silica−alumina. While a near-quantitative toluene yield is obtained, some of the phenolic products remain adsorbed on the catalyst.

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Mechanocatalytic hydrogenolysis of benzyl phenyl ether over supported nickel catalysts

Abstract: Mechanocatalysis is a promising approach for green, solvent-free biomass deconstruction and valorization. Here, the hydrogenolysis of benzyl phenyl ether (BPE), a model lignin ether, via ball milling is demonstrated over...

Cited by 4 publications

References 77 publications

Hydrogenation of different carbon substrates into light hydrocarbons by ball milling

Hydrogenation of different carbon substrates into light hydrocarbons by ball milling

Pathways Toward Efficient and Durable Anion Exchange Membrane Water Electrolyzers Enabled By Electro‐Active Porous Transport Layers

Mechanocatalytic Hydrogenolysis of the Lignin Model Dimer Benzyl Phenyl Ether over Supported Palladium Catalysts

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