Highly efficient, NiAu-catalyzed hydrogenolysis of lignin into phenolic chemicals

Zhang, Jiaguang; Asakura, Hiroyuki; Rijn, Jeaphianne van; Yang, Jun; Duchesne, Paul N.; Zhang, Bin; Chen, Xi; Zhang, Peng; Saeys, Mark; Yan, Ning

doi:10.1039/c3gc42589d

Cited by 247 publications

(144 citation statements)

References 48 publications

(70 reference statements)

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“…It was proposed that the improved yield from combining Raney Ni with a zeolite arose from the latter hindering the reaction between the parent lignin and other more reactive lignin fragments that could together to produce high molecular weight oligomers. Bimetallic NiM (M = Ru, Rh, Pd, Au, Mo) catalysts have also been studied for lignin hydrogenolysis [33,34], [35] [36], wherein NaOH addition proved beneficial, promoting the formation of aromatic compounds and supressing arene hydrogenation. Konnerth et al [37] also observed increased Organosolv lignin depolymerization via NaOH addition to the aqueous reaction mixture containing an Ni 7 Au 3 Fig.…”

Section: Hydrogenolysismentioning

confidence: 99%

Heterogeneously catalyzed lignin depolymerization

Pineda

Lee

2016

Appl Petrochem Res

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Biomass offers a unique resource for the sustainable production of bio-derived chemical and fuels as drop-in replacements for the current fossil fuel products. Lignin represents a major component of lignocellulosic biomass, but is particularly recalcitrant for valorization by existing chemical technologies due to its complex crosslinking polymeric network. Here, we highlight a range of catalytic approaches to lignin depolymerisation for the production of aromatic bio-oil and monomeric oxygenates.

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Section: Hydrogenolysismentioning

confidence: 99%

Heterogeneously catalyzed lignin depolymerization

Pineda

Lee

2016

Appl Petrochem Res

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“…Monometallic Ni catalyst showed a conversion of 35.8% with 25.5% monomer yield, whereas monometallic Ag catalyst was almost inert for this reaction. [55] Interestingly, NiAg prepared from different precursors exhibited distinctively different activities. Over Ni 0.5 Ag 0.5 -A, which was derived from acetate precursors, similar monomer and dimer yields were achieved as compared to monometallic Ni catalyst.…”

Section: Resultsmentioning

confidence: 99%

“…[56] Notably, gold, which itself was almost inert in the hydrogenolysis of β-O-4 linkage, unpredictably exhibited similar promotional effect compared with Ru, Pt, and Pd. [55] Silver is in the same group with gold, and is cheaper and more abundant. This prompted us to develop a bimetallic NiAg catalyst for lignin hydrogenolysis.…”

Section: Introductionmentioning

confidence: 98%

“…Our group reported the hydrogenolysis of β-O-4 linkage in model compounds and in real lignin over a series of nickel based bimetallic catalysts (NiAu, NiPt, NiRu, and NiRh). [54][55][56] The incorporation of a second metal facilitated the reduction of nickel in the co-reduction process, forming a noble metal-nickel core-shell structure with smaller particle size, leading to the increase of surface sites. The second metal donates electrons to Ni making it more electron enriched.…”

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confidence: 99%

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NiAg Catalysts for Selective Hydrogenolysis of the Lignin C-O Bond

Zhang

Yan

2016

Part. Part. Syst. Charact.

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breaking down this specific linkage in a selective manner under mild reaction conditions would depolymerize lignin, paving the way for lignin valorization. [29][30][31][32] The catalytic cleavage of β-O-4 linkage has been studied in oxidative, [33][34][35][36][37] reductive, [38,39] and redox-neutral [40][41][42] manners. C O bond hydrogenolysis, which transforms lignin into a library of phenolic platform chemicals in the presence of hydrogen, is attracting increasing interests. [43] Nickel based catalyst appears to be promising. A soluble nickel carbene complex was developed to catalyze the hydrogenolysis of 4-O-5 lignin model compounds in organic solvents. [44] Following that, Ni/SiO 2 [45] and Ni/C [46] catalysts were employed to treat lignin or lignin model compounds. Recently, lignin hydrogenolysis by Ni/LDH, [47] Ni/SBA-15, [48] and Ni/SiC [49] were developed. Remarkably, Ni-based catalysts were employed for the hydro-treatment of raw biomass. Ni nanoparticles (NPs) generated in situ from Ni-containing MIL-77 were evaluated in the upgrading of a biomass derived bio-oil, exhibiting more than ten times higher hydrogenolysis activity as compared with a commercial Ni/SiO 2 -Al 2 O 3 catalyst. [50] NiMo/Al 2 O 3 , a hydrogenolysis catalyst in petroleum industry, was employed for the simultaneous liquefaction and hydrogenolysis of several raw woody biomasses, yielding more than 50% liquid products. [51,52] A key challenge in lignin hydrogenolysis is the competitive hydrogenation of the aromatic rings over C O bond hydrogenolysis. The undesired hydrogenation reaction leads to extra consumption of H 2 , and generation of saturated products that are more resistant to hydrogenolysis. Calculation shows that the C aliphatic OC aryl bond dissociation energy of 2-phenylethyl phenyl ether is 289 kJ mol −1 , [45] whereas the hydrogenated counterpart possesses a C aliphatic OC aliphatic bond with considerably higher strength (351 kJ mol −1 ). [53] Therefore, it is necessary to develop catalysts that can effectively break the C aliphatic OC aryl bonds while inhibit hydrogenating the aromatic rings. Our group reported the hydrogenolysis of β-O-4 linkage in model compounds and in real lignin over a series of nickel based bimetallic catalysts (NiAu, NiPt, NiRu, and NiRh). [54][55][56] The incorporation of a second metal facilitated the reduction of nickel in the co-reduction process, forming a noble metal-nickel core-shell structure with smaller particle size, leading to the increase of surface sites. The second metal donates electrons to Ni making it more electron enriched. This facilitates the oxidative addition

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“…Hydrogenolysis, catalytic cracking, and solvothermal treatment were the main methods adopted [4,5], and a satisfied yield of monophenols was obtained [6,7]. A high yield of monophenols was achieved by Zhao et al via the catalytic hydrogenation process [8].…”

Section: Introductionmentioning

confidence: 99%

High Efficient Hydrogenation of Lignin-Derived Monophenols to Cyclohexanols over Pd/γ-Al2O3 under Mild Conditions

Luo

et al. 2016

Catalysts

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Abstract:The catalytic hydrogenation of lignin-derived monophenols with high efficiency and selectivity is important for the sustainable production of chemicals and fuels. Here, Pd/γ-Al 2 O 3 was prepared via impregnation and used as catalyst for the hydrogenation of phenols to cyclohexanols under mild conditions in aqueous solution. 3 wt. % Pd/γ-Al 2 O 3 exhibited good catalytic activity for the selective hydrogenation of 4-ethylphenol into 4-ethylcyclohexanol, and a conversion of 100% with selectivity of 98.9% was achieved at 60˝C for 12 h. Other lignin-derived monophenolic model compounds such as 4-methyl phenol and 4-propyl phenol could be hydrogenated into cyclohexanols selectively under optimal conditions. Moreover, the Pd/γ-Al 2 O 3 catalyst displayed good activity for the hydrogenation of the mixture of monophenols directly derived from raw biomass system to cyclohexanols as the main products, and was favorable for the depolymerization of lignin oligomers under milder conditions. Pd/γ-Al 2 O 3 catalyst showed good water resistance and stability after recycling four times. This result might provide a promising approach to selectively producing cyclohexanol directly from raw biomass material under mild conditions in aqueous solutions.

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Highly efficient, NiAu-catalyzed hydrogenolysis of lignin into phenolic chemicals

Abstract: A highly efficient, stable NiAu catalyst that exhibits unprecedented low temperature activity in lignin hydrogenolysis was for the first time developed, leading to the formation of 14 wt% aromatic monomers from organosolv lignin at 170 °C in pure water.

Cited by 247 publications

References 48 publications

Heterogeneously catalyzed lignin depolymerization

Heterogeneously catalyzed lignin depolymerization

NiAg Catalysts for Selective Hydrogenolysis of the Lignin C-O Bond

High Efficient Hydrogenation of Lignin-Derived Monophenols to Cyclohexanols over Pd/γ-Al2O3 under Mild Conditions

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