Efficient liquid-phase hydrogenolysis of a lignin model compound (benzyl phenyl ether) using a Ni/carbon catalyst

Matsagar, Babasaheb M.; Kang, Ting-Cih; Wang, Zheng-Yen; Yoshikawa, Takuya; Nakasaka, Yuta; Masuda, Toshio; Chuang, Li-Ching; Wu, Kevin C.‐W.

doi:10.1039/c8re00304a

Cited by 36 publications

(23 citation statements)

References 54 publications

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“…For example, acid or base is usually added for promoting hydrolysis reaction, metal oxide catalysts are employed to improve the oxidative reactions, and many transition metal‐based catalysts (Ni, Pd, Ru, Pt, etc.) are found to have higher reactivity for hydro‐deoxygenation (HDO), hydrogenolysis, and hydrogenation reactions . These reactions happen simultaneously in the same system which creates difficulty in controlling the lignin fractionation to selective production of target compounds.…”

Section: Introductionmentioning

confidence: 99%

Effect of Solvent, Role of Formic Acid and Rh/C Catalyst for the Efficient Liquefaction of Lignin

et al. 2019

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We demonstrate highly efficient liquefaction of alkali lignin with a very high yield of THF‐soluble bio‐oil (91.5 wt %) using formic acid (FA) and Rh/C catalyst under relatively mild reaction conditions (250 °C, 6 h) in EtOH−H2O co‐solvent system. The monomeric products are identified in which alkyl guaiacols accounts for the main proportion. The role of FA was not only used as a liquid‐phase in‐situ hydrogen source but also acts as organic acid which can catalyze the hydrolysis reaction of −C−O−C ether bonds of lignin. Moreover, in the present study, the role of Rh/C and FA is demonstrated for the liquefaction of lignin. The replacement of pure H2 gas by the liquid‐phase FA (hydrogen source) can effectively prevent the char formation. The utilization of Rh/C catalyst helps for the conversion of alkenyl guaiacols to alkyl guaiacols suggesting the hydrogenation of phenolic monomers and further cleavage by hydrogenation results in the formation of bio‐oil with lower molecular weight (Mn=466 g mol−1) as well as lower O/C ratio (0.26).

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Section: Introductionmentioning

confidence: 99%

Effect of Solvent, Role of Formic Acid and Rh/C Catalyst for the Efficient Liquefaction of Lignin

et al. 2019

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“…Reductive depolymerization of lignin involves the hydrogenolysis of C–O and C–C interunit linkages, which is usually occurred in the presence of a catalyst under hydrogen pressure [ 187 ]. The main product of the reaction is a bio-oil rich in substituted guaicyl and syringyl type compounds as well as alkylated phenols [ 182 ].…”

Section: Lignin Hydrogenolysis To Valuable Phenolic Compoundsmentioning

confidence: 99%

Carbon-Based Nanocatalysts (CnCs) for Biomass Valorization and Hazardous Organics Remediation

et al. 2022

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The continuous increase of the demand in merchandise and fuels augments the need of modern approaches for the mass-production of renewable chemicals derived from abundant feedstocks, like biomass, as well as for the water and soil remediation pollution resulting from the anthropogenic discharge of organic compounds. Towards these directions and within the concept of circular (bio)economy, the development of efficient and sustainable catalytic processes is of paramount importance. Within this context, the design of novel catalysts play a key role, with carbon-based nanocatalysts (CnCs) representing one of the most promising class of materials. In this review, a wide range of CnCs utilized for biomass valorization towards valuable chemicals production, and for environmental remediation applications are summarized and discussed. Emphasis is given in particular on the catalytic production of 5-hydroxymethylfurfural (5-HMF) from cellulose or starch-rich food waste, the hydrogenolysis of lignin towards high bio-oil yields enriched predominately in alkyl and oxygenated phenolic monomers, the photocatalytic, sonocatalytic or sonophotocatalytic selective partial oxidation of 5-HMF to 2,5-diformylfuran (DFF) and the decomposition of organic pollutants in aqueous matrixes. The carbonaceous materials were utilized as stand-alone catalysts or as supports of (nano)metals are various types of activated micro/mesoporous carbons, graphene/graphite and the chemically modified counterparts like graphite oxide and reduced graphite oxide, carbon nanotubes, carbon quantum dots, graphitic carbon nitride, and fullerenes.

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“…Additionally, metal-catalyzed oxidative lignin depolymerization has offered great advantages because of its high selectivity and relatively milder reaction condition; therefore, metal supported catalysts have been extensively used for lignin valorization [13,28,29]. It has been reported that Au/TiO 2 , however, favored ring-opening reactions of lignin while Pt/TiO 2 effectively promoted lignin condensation and gave minimal effect on ringopening reaction [30].…”

Section: Introductionmentioning

confidence: 99%

Lignin-Derived Syringol and Acetosyringone from Palm Bunch Using Heterogeneous Oxidative Depolymerization over Mixed Metal Oxide Catalysts under Microwave Heating

et al. 2021

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Biomass valorization to building block chemicals in food and pharmaceutical industries has tremendously gained attention. To produce monophenolic compounds from palm empty fruit bunch (EFB), EFB was subjected to alkaline hydrothermal extraction using NaOH or K2CO3 as a promotor. Subsequently, EFB-derived lignin was subjected to an oxidative depolymerization using Cu(II) and Fe(III) mixed metal oxides catalyst supported on γ-Al2O3 or SiO2 as the catalyst in the presence of hydrogen peroxide. The highest percentage of total phenolic compounds of 63.87 wt% was obtained from microwave-induced oxidative degradation of K2CO3 extracted lignin catalyzed by Cu-Fe/SiO2 catalyst. Main products from the aforementioned condition included 27.29 wt% of 2,4-di-tert-butylphenol, 19.21 wt% of syringol, 9.36 wt% of acetosyringone, 3.69 wt% of acetovanillone, 2.16 wt% of syringaldehyde, and 2.16 wt% of vanillin. Although the total phenolic compound from Cu-Fe/Al2O3 catalyst was lower (49.52 wt%) compared with that from Cu-Fe/SiO2 catalyst (63.87 wt%), Cu-Fe/Al2O3 catalyst provided the greater selectivity of main two value-added products, syringol and acetosyrigone, at 54.64% and 23.65%, respectively (78.29% total selectivity of two products) from the NaOH extracted lignin. The findings suggested a promising method for syringol and acetosyringone production from the oxidative heterogeneous lignin depolymerization under low power intensity microwave heating within a short reaction time of 30 min.

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Efficient liquid-phase hydrogenolysis of a lignin model compound (benzyl phenyl ether) using a Ni/carbon catalyst

Abstract: Efficient liquid-phase hydrogenolysis of benzyl phenyl ether using Ni/CB in an EtOH/H2O co-solvent system.

Cited by 36 publications

References 54 publications

Effect of Solvent, Role of Formic Acid and Rh/C Catalyst for the Efficient Liquefaction of Lignin

Effect of Solvent, Role of Formic Acid and Rh/C Catalyst for the Efficient Liquefaction of Lignin

Carbon-Based Nanocatalysts (CnCs) for Biomass Valorization and Hazardous Organics Remediation

Lignin-Derived Syringol and Acetosyringone from Palm Bunch Using Heterogeneous Oxidative Depolymerization over Mixed Metal Oxide Catalysts under Microwave Heating

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