Role of the In Situ Generated Acidic Protons and Cl Species for 2,5-Hexanedione Production from the New Platform Molecule 5-(Chloromethyl)furfural

Review Energy & Fuels

Recent advances in the production and value addition of selected hydrophobic analogs of biomass-derived 5-(hydroxymethyl)furfural

Harshitha N. Anchan et al.

Summary: This review discusses the production and derivative chemistry of various hydrophobic analogs of 5-(Hydroxymethyl)furfural (HMF), highlighting their advantages and challenges.

BIOMASS CONVERSION AND BIOREFINERY (2023)

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Article Chemistry, Multidisciplinary

2,5-Hexanedione: The Bridge for p-Xylene Production from Lignocellulosic Biomass via a Brand New Two-Step Route

Haodong Chu et al.

Summary: The efficient and green conversion of cellulose into p-xylene (PX) is important for utilizing biomass wastes and promoting the recycling economy. A new two-step PX production route via 2,5-hexanedione (HDO) has been proposed, simplifying the process and reducing costs. The highest yields of 64% and 85% were achieved for HDO/2,5-dimethylfuran (DMF) and PX during the first and second steps, respectively.

ACS SUSTAINABLE CHEMISTRY & ENGINEERING (2023)

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Article Chemistry, Applied

One-pot synthesis of 2,5-bis(hydroxymethyl)furan from biomass derived 5-(chloromethyl)furfural in high yield

Binglin Chen et al.

Summary: This study demonstrates, for the first time, the one-pot conversion of 5-(chloromethyl)furfural (CMF) to 2,5-bis(hydroxymethyl)furan (BHMF) in the water phase. A BHMF yield of 91% was achieved using a Ru/CuOx catalyst, with BHMF mainly produced through consecutive hydrolysis and hydrogenation of CMF with 5-hydroxymethylfurfural (HMF) as an intermediate.

JOURNAL OF ENERGY CHEMISTRY (2023)

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Article Chemistry, Physical

Identifying Metal-Halogen Bonding for Hydrogen-Induced Acid Generation in Bifunctional Catalysis

Yong Zhou et al.

Summary: In conventional bifunctional catalysts, active metal sites are associated with metal components, while acid sites are usually localized over oxide supports. The modification of metal sites by halogens provides an opportunity to generate acidity via the heterolytic dissociation of hydrogen directly over metal sites. High-throughput screening of different metal-halogen combinations reveals that only Pd and Pt catalysts demonstrate the formation of acid sites by interaction with Br, Cl, and I. Characterization and density functional theory (DFT) modeling suggest that hydrogen heterolytic dissociation occurs over halogens localized at the edges and corners of Pd and Pt nanoparticles, with the strength of the acid sites increasing with the electronegativity of the halogen.

ACS CATALYSIS (2023)

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Article Chemistry, Physical

Deep eutectic solvents promote the formation of ultradispersed ZrO2 in cellulose-based carbon aerogel for the transfer hydrogenation of biomass aldehydes

Sishi Long et al.

Summary: Zr-carbon aerogel (Zr-DCCA) was prepared using renewable deep eutectic solvents (DESs) and cellulose nanofiber as templates. Zr-DCCA exhibited high conversion, selectivity, and stability for transfer hydrogenation of various biomass aldehydes. Comparative studies with Zr-based carbon aerogels (Zr-CCA) prepared without DESs showed lower catalytic performance. Characterizations revealed that Zr-DCCA had higher dispersion and smaller size of ZrO2 nanoparticles, resulting in stronger acid/base properties. Furthermore, the absence of traditional stirring and centrifugation in the reaction simplified equipment and operations, making the process more practical.

MOLECULAR CATALYSIS (2023)

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Article Chemistry, Multidisciplinary

Halogen-Incorporated Sn Catalysts for Selective Electrochemical CO2 Reduction to Formate

Tian Wang et al.

Summary: In this work, halogen (F, Cl, Br or I) was introduced into Sn catalyst to enhance its catalytic performance in electrochemical CO2 reduction reaction (CO2RR) to produce formate. The presence of halogen was confirmed by characterizations, which resulted in a more positive valence state of Sn and tuned the adsorption strength of the key intermediate towards formate formation.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2023)

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Article Chemistry, Physical

Selectively reductive amination of levulinic acid with aryl amines to N-substituted aryl pyrroles

Cailing Wu et al.

Summary: In this study, N-substituted aryl pyrroles were synthesized by reductive amination/cyclization of levulinic acid with primary aromatic amines and hydrosilanes over CsF. The reaction proceeded in two steps, resulting in the formation of intermediate 5-methyl-N-alkyl-1,3-dihydro-2H-pyrrolones and their isomeride (B), followed by chemo- and region-selective reduction to produce the final products. This synthesis approach offers promising applications due to its mild and environmentally friendly conditions.

GREEN ENERGY & ENVIRONMENT (2023)

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Review Chemistry, Physical

Catalytic conversion of lignocellulosic biomass into chemicals and fuels

Weiping Deng et al.

Summary: This review article focuses on the state-of-the-art catalytic transformation of lignocellulosic biomass into value-added chemicals and fuels, including the conversion of cellulose, hemicellulose, and lignin, as well as the gasification and pyrolysis of whole biomass. The opportunities, challenges, and prospects of woody biomass valorization are highlighted.

GREEN ENERGY & ENVIRONMENT (2023)

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Article Chemistry, Multidisciplinary

Efficient Synthesis of 5-(Hydroxymethyl)furfural Esters from Polymeric Carbohydrates Using 5-(Chloromethyl)furfural as a Reactive Intermediate

Navya Subray Bhat et al.

Summary: This study presents an efficient method to synthesize HMF esters from biomass-derived CMF, with potential applications as chemical intermediates, fuel additives, and bioactive compounds. By converting microcrystalline cellulose into CMF under optimized conditions and further transforming it into HMF esters, high yields were achieved.

ACS SUSTAINABLE CHEMISTRY & ENGINEERING (2022)

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Article Multidisciplinary Sciences

Cobalt-catalyzed branched selective hydroallylation of terminal alkynes

Jieping Chen et al.

Summary: In this study, a cobalt-catalyzed selective hydroallylation reaction was developed to synthesize branched 1,4-dienes. The reaction exhibited excellent functional group tolerance and substrate scope, allowing for gram-scale reactions. The proposed mechanism was based on deuterium labeling experiment and kinetic studies.

NATURE COMMUNICATIONS (2022)

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Article Multidisciplinary Sciences

A unique Co@CoO catalyst for hydrogenolysis of biomass-derived 5-hydroxymethylfurfural to 2,5-dimethylfuran

Shuang Xiang et al.

Summary: The authors report a unique core-shell structured Co@CoO catalyst which shows excellent performance in the hydrogenolysis and deoxygenation reactions of biomass-derived compounds. This study reveals the great potential of simple metal-oxide-based catalysts for the conversion of renewable biomass into chemical feedstocks.

NATURE COMMUNICATIONS (2022)

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Article Chemistry, Multidisciplinary

Insights into the Hydrogenolysis Mechanism of Diphenyl Ether over Cl-Modified Pt/?-Al2O3 Catalysts by Experimental and Theoretical Studies

Chen Zhu et al.

Summary: This study demonstrates that a Cl-modified Pt/??-Al2O3 catalyst exhibits higher selectivity in C???O bond cleavage reactions. Cl species preferentially localize at terrace sites of Pt nanoparticles, leading to a decrease in active sites and suppression of hydrogenation reactions on aromatic products.

ACS SUSTAINABLE CHEMISTRY & ENGINEERING (2022)

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Article Chemistry, Multidisciplinary

H+-H- Pairs in Partially Oxidized MAX Phases for Bifunctional Catalytic Conversion of Furfurals into Linear Ketones

Qiang Deng et al.

Summary: A series of partially oxidized MAX phase supported Pd catalysts showed excellent catalytic performance in the conversion of biomass-derived furfurals to ketones. Detailed studies revealed that in situ hydrogen spillover generates Frustrated Lewis H+-H- pairs, which play a crucial role in promoting selective C=O hydrogenation and ring opening reactions.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

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Article Chemistry, Physical

Efficient synthesis of the liquid fuel 2,5-dimethylfuran from biomass derived 5-(chloromethyl)furfural at room temperature

Binglin Chen et al.

Summary: The synthesis of renewable transportation fuel 2,5-dimethylfuran (DMF) from biomass was studied. It was found that the in-situ generation of acidic species and Pd-Cl active sites showed high selectivity and activity towards hydrogenolysis of biomass-derived 5-(chloromethyl)furfural (CMF) to DMF. The method achieved a 92% DMF yield from CMF in 15 minutes, with a space-time-yield at least one order of magnitude higher than previous literature using 5-hydroxymethylfurfural (HMF) as substrate.

APPLIED CATALYSIS B-ENVIRONMENTAL (2022)

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Article Chemistry, Physical

Vitamin B9 derived nitrogen-doped graphene for metal-free aerobic oxidation of biomass-derived chemicals

Duan-Jian Tao et al.

Summary: A superior carbocatalyst, ultrahigh N-doped graphene, was prepared using a self-sacrificial templating method. The catalyst exhibited high activity for the oxidation of bio-based alcohols and terpenes without any additives. The high content of graphitic N and pyridinic N species in the catalyst promoted the generation of active reactants and improved the catalytic performance.

GREEN ENERGY & ENVIRONMENT (2022)

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Article Chemistry, Physical

Synthesis of ordered hierarchically mesoporous/microporous carbon materials via compressed CO2 for fructose-to-HMF transformation

Sen Luan et al.

Summary: This study successfully fabricated well-ordered hierarchically mesoporous/microporous carbon materials using a dual soft-templating approach with compressed CO2. The influence of different types of surfactants on the morphology and nanostructure of the carbon samples was investigated. The prepared carbon samples were used as catalyst carriers for the conversion of fructose to HMF, and the optimal reaction conditions were determined. The catalytic performance and stability of the samples were evaluated, and a possible catalytic mechanism was proposed.

GREEN ENERGY & ENVIRONMENT (2022)

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Article Chemistry, Physical

Vitamin B-9 derived nitrogen-doped graphene for metal-free aerobic oxidation of biomass-derived chemicals

Duan-Jian Tao et al.

Summary: A superior carbocatalyst ultrahigh N-doped graphene was prepared by a novel self-sacrificial templating method, showing excellent catalytic performance for the oxidation of bio-based alcohols and terpenes without any additives.

GREEN ENERGY & ENVIRONMENT (2022)

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Article Multidisciplinary Sciences

Synthesis of bio-based methylcyclopentadiene via direct hydrodeoxygenation of 3-methylcyclopent-2-enone derived from cellulose

Yanting Liu et al.

Summary: Efficient conversion of renewable biomass into fuels and chemicals is a key focus due to energy and environmental concerns. The authors present an innovative method for producing methylcyclopentadiene (MCPD) from cellulose, demonstrating high selectivity with a yield of 70% using a zinc-molybdenum oxide catalyst.

NATURE COMMUNICATIONS (2021)

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Article Multidisciplinary Sciences

Selective hydrogenation of 5-(hydroxymethyl)furfural to 5-methylfurfural over single atomic metals anchored on Nb2O5

Shaopeng Li et al.

Summary: This study demonstrates that isolated single atomic catalysts can efficiently catalyze the selective hydrogenation of HMF to MF using H2 as the reductant, with a selectivity of >99% at complete conversion of HMF.

NATURE COMMUNICATIONS (2021)

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Article Chemistry, Physical

Dual Metal-Acid Pd-Br Catalyst for Selective Hydrodeoxygenation of 5-Hydroxymethylfurfural (HMF) to 2,5-Dimethylfuran at Ambient Temperature

Dan Wu et al.

Summary: This novel supported metal bifunctional catalyst combines the advantages of promotion and bifunctionality, achieved by pretreating supported palladium catalysts with bromobenzene to create Bronsted acid sites. The catalyst shows unique catalytic properties in hydrodeoxygenation reactions with stable performance, yielding up to 96% at ambient temperature under 5 bar of H-2.

ACS CATALYSIS (2021)

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Article Chemistry, Multidisciplinary

Selective Cellulose Hydrogenolysis to 2,5-Hexanedione and 1-Hydroxy-2-hexanone Using Ni@NC Combined with H3PO4

Yuan Liang et al.

Summary: In this study, Ni@ NC catalysts were successfully used for the direct hydrogenolysis of cellulose to produce ketone compounds with high yields. The key intermediates for the formation of target products were hydrolyzed glucose and selective hydrodeoxygenation of hexoses. The synergy between N species of Ni@NC catalysts and metallic Ni played a crucial role in promoting glucose isomerization and selective preservation of C.O bonds in the production of ketones.

ACS SUSTAINABLE CHEMISTRY & ENGINEERING (2021)

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Article Chemistry, Physical

Direct Synthesis of Methylcyclopentadiene with 2,5-Hexanedione over Zinc Molybdates

Ran Wang et al.

Summary: The study presents an efficient method for the direct synthesis of renewable MCPD from biomass and demonstrates the excellent catalytic performance of Zn3Mo2O9 catalyst in this process. This method shows advantages in terms of high yield, cost savings, and stability.

ACS CATALYSIS (2021)

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Article Chemistry, Physical

Is hydrolysis a bad news for p-xylene production from 2,5-dimethylfuran and ethylene? Mechanism investigation into the role of acid strength during 2,5-hexanedione conversion

Xinqiang Feng et al.

Summary: In this study, a series of metal phosphate catalysts with varied acid strength were prepared to investigate their role in the reaction between DMF and HDO. Strong acid sites were found to play a vital role in the further condensation of HDO, leading to a decrease in PX selectivity. The study provides insights into the importance of acid strength for rational design of new catalysts and mechanistic understanding.

JOURNAL OF CATALYSIS (2021)

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Article Chemistry, Applied

Reveal the nature of particle size effect for CO2 reduction over Pd and Au

Piaoping Yang et al.

Summary: This study investigates the crucial role of model and coverage effect on understanding the nature of active sites for CO2 reduction over Au and Pd NPs using DFT calculations. Different CO selectivity results on terrace and edge sites on Au and Pd NPs reveal the computational model effect on clarifying active site properties. The coverage effect is more significant for Pd catalysts, indicating the necessity of reasonable models in DFT calculations.

CHINESE JOURNAL OF CATALYSIS (2021)

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Review Chemistry, Multidisciplinary

Earth-abundant 3d-transition-metal catalysts for lignocellulosic biomass conversion

Yunchao Feng et al.

Summary: The transformation of biomass into chemicals and fuels is a long-term goal in both science and industry, but high cost is a major obstacle to industrialization. Therefore, the development of catalysts with high activity and low cost is crucial. The use of earth-abundant 3d-transition-metals in catalysis has seen increasing achievement in the past two decades due to their low cost, high efficiency, and excellent stability.

CHEMICAL SOCIETY REVIEWS (2021)

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Article Chemistry, Multidisciplinary

Ultrasmall Pd-Cu-Pt Trimetallic Twin Icosahedrons Boost the Electrocatalytic Performance of Glycerol Oxidation at the Operating Temperature of Fuel Cells

Fang Yang et al.

ADVANCED FUNCTIONAL MATERIALS (2020)

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Article Multidisciplinary Sciences

Entropy-stabilized single-atom Pd catalysts via high-entropy fluorite oxide supports

Haidi Xu et al.

NATURE COMMUNICATIONS (2020)

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Article Chemistry, Physical

Particle Size Effects in Stoichiometric Methane Combustion: Structure-Activity Relationship of Pd Catalyst Supported on Gamma-Alumina

Jianjun Chen et al.

ACS CATALYSIS (2020)

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Article Chemistry, Multidisciplinary

Selectivity Control in Photocatalytic Valorization of Biomass-Derived Platform Compounds by Surface Engineering of Titanium Oxide

Xuejiao Wu et al.

CHEM (2020)

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Article Chemistry, Multidisciplinary

Producing methylcyclopentadiene dimer and trimer based high-performance jet fuels using 5-methyl furfural

Genkuo Nie et al.

GREEN CHEMISTRY (2020)

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Article Chemistry, Multidisciplinary

Heterogeneous (de)chlorination-enabled control of reactivity in the liquid-phase synthesis of furanic biofuel from cellulosic feedstock

Hu Li et al.

GREEN CHEMISTRY (2020)

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Article Chemistry, Multidisciplinary

5-(Chloromethyl)furfural (CMF): A Platform for Transforming Cellulose into Commercial Products

Mark Mascal

ACS SUSTAINABLE CHEMISTRY & ENGINEERING (2019)

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Article Chemistry, Physical

Selective conversion of 5-hydroxymethylfurfural to diketone derivatives over Beta zeolite-supported Pd catalysts in water

Ruben Ramos et al.

JOURNAL OF CATALYSIS (2019)

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Article Chemistry, Physical

Integrated Conversion of Cellulose to High-Density Aviation Fuel

Yanting Liu et al.

JOULE (2019)

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Article Multidisciplinary Sciences

Dendritic defect-rich palladium-copper-cobalt nanoalloys as robust multifunctional non-platinum electrocatalysts for fuel cells

Chaozhong Li et al.

NATURE COMMUNICATIONS (2018)

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Article Chemistry, Multidisciplinary

Control of selectivity in hydrosilane-promoted heterogeneous palladium-catalysed reduction of furfural and aromatic carboxides

Hu Li et al.

COMMUNICATIONS CHEMISTRY (2018)

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Article Chemistry, Physical

New bio-based monomers: tuneable polyester properties using branched diols from biomass

Sacha Perocheau Arnaud et al.

FARADAY DISCUSSIONS (2017)

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Article Chemistry, Multidisciplinary

Electronic Effect of Ruthenium Nanoparticles on Efficient Reductive Amination of Carbonyl Compounds

Tasuku Komanoya et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2017)

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Article Chemistry, Physical

New bio-based monomers: tuneable polyester properties using branched diols from biomass

Sacha Perocheau Arnaud et al.

FARADAY DISCUSSIONS (2017)

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Article Chemistry, Physical

Poisoning of Ru/C by homogeneous Bronsted acids in hydrodeoxygenation of 2,5-dimethylfuran via catalytic transfer hydrogenation

Matthew J. Gilkey et al.

APPLIED CATALYSIS A-GENERAL (2017)

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Article Chemistry, Physical

Comparative study on hydrogenation of propanal on Ni(111) and Cu(111) from density functional theory

Wei An et al.

APPLIED SURFACE SCIENCE (2017)

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Article Chemistry, Multidisciplinary

Production of 2,5-hexanedione and 3-methyl-2-cyclopenten-1-one from 5-hydroxymethylfurfural

Dezhang Ren et al.

GREEN CHEMISTRY (2016)

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Article Chemistry, Multidisciplinary

Size-Dependent Electrocatalytic Reduction of CO2 over Pd Nanoparticles

Dunfeng Gao et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2015)

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Article Chemistry, Physical

Hydrogenation/Hydrolytic Ring Opening of 5-HMF by Cp*-Iridium(III) Half-Sandwich Complexes for Bioketones Synthesis

Zhanwei Xu et al.

ACS CATALYSIS (2015)

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Article Chemistry, Multidisciplinary

Copper-Catalyzed Intermolecular Regioselective Hydroamination of Styrenes with Polymethylhydrosiloxane and Hydroxylamines

Yuya Miki et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2013)

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Article Chemistry, Multidisciplinary

On the Bronsted Acid-Catalyzed Homogeneous Hydrolysis of Furans

Nima Nikbin et al.

CHEMSUSCHEM (2013)

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Article Chemistry, Multidisciplinary

Microwave-assisted oxidation of alcohols by hydrogen peroxide catalysed by tetrabutylammonium decatungstate

Mateusz Galica et al.

CHEMICAL PAPERS (2013)

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Article Chemistry, Physical

A consistent and accurate ab initio parametrization of density functional dispersion correction (DFT-D) for the 94 elements H-Pu

Stefan Grimme et al.

JOURNAL OF CHEMICAL PHYSICS (2010)

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Article Engineering, Environmental

Prediction of impact sensitivity of nitro energetic compounds by neural network based on electrotopological-state indices

Rui Wang et al.

JOURNAL OF HAZARDOUS MATERIALS (2009)

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Article Chemistry, Physical

A climbing image nudged elastic band method for finding saddle points and minimum energy paths

G Henkelman et al.

JOURNAL OF CHEMICAL PHYSICS (2000)

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Role of the In Situ Generated Acidic Protons and Cl Species for 2,5-Hexanedione Production from the New Platform Molecule 5-(Chloromethyl)furfural

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