Highly efficient hydrogenation of levulinic acid into 2-methyltetrahydrofuran over Ni–Cu/Al2O3–ZrO2bifunctional catalysts

Xie, Ziyi; Chen, Bingfeng; Wu, Haoran; Li, Mingyang; Liu, Huizhen; Zhang, Jianling; Yang, Guanying

doi:10.1039/c8gc02914h

Cited by 70 publications

(44 citation statements)

References 38 publications

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“…In addition, the role of i ‐PrOH as both solvent and hydrogen transfer agent was demonstrated for this system [142] . In 2019, Han, Chen and co‐workers reported a Cu−Ni/Al 2 O 3 ‐ZrO 2 catalytic system affording the highest yields of 2‐MeTHF (>99 %) obtained up to date through the LA reductive etherification with H 2 (Scheme 29K) [143] . In this work, it is demonstrated the bimetallic synergy, as Cu favors 2‐MeTHF selectivity, while Ni is key for GVL hydrogenolysis to take place.…”

Section: Reductive Etherification Of Alcohols With Carboxylic Acid Derivativesmentioning

confidence: 96%

Catalytic Reductive Alcohol Etherifications with Carbonyl‐Based Compounds or CO₂ and Related Transformations for the Synthesis of Ether Derivatives

et al. 2021

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Ether derivatives have myriad applications in several areas of chemical industry and academia. Hence, the development of more effective and sustainable protocols for their production is highly desired. Among the different methodologies reported for ether synthesis, catalytic reductive alcohol etherifications with carbonyl‐based moieties (aldehydes/ketones and carboxylic acid derivatives) have emerged in the last years as a potential tool. These processes constitute appealing routes for the selective production of both symmetrical and asymmetrical ethers (including O‐heterocycles) with an increased molecular complexity. Likewise, ester‐to‐ether catalytic reductions and hydrogenative alcohol etherifications with CO2 to dialkoxymethanes and other acetals, albeit in less extent, have undergone important advances, too. In this Review, an update of the recent progresses in the area of catalytic reductive alcohol etherifications using carbonyl‐based compounds and CO2 have been described with a special focus on organic synthetic applications and catalyst design. Complementarily, recent progress made in catalytic acetal/ketal‐to‐ether or ester‐to‐ether reductions and other related transformations have been also summarized.

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Section: Reductive Etherification Of Alcohols With Carboxylic Acid Derivativesmentioning

confidence: 96%

Catalytic Reductive Alcohol Etherifications with Carbonyl‐Based Compounds or CO₂ and Related Transformations for the Synthesis of Ether Derivatives

et al. 2021

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“…The excellent activity of the catalyst was attributed to the mesoporous structure, the supporting material containing acidic sites, and the synergistic effect between Cu and Ni. The catalyst was successfully reused five times without a considerable loss of catalytic activity and selectivity [192] . Co/silica catalyst was used for the preparation of MTHF from LA in a fixed bed microreactor under flowing hydrogen.…”

Section: Chemical Modification Of Both Ketone and Carboxylic Acid Functionality In Lamentioning

confidence: 99%

Recent Advances in the Value Addition of Biomass‐Derived Levulinic Acid: A Review Focusing on its Chemical Reactivity Patterns

Dutta

Bhat

2021

ChemCatChem

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Levulinic acid (LA) is one of the most prominent biomass‐derived chemical building blocks that can be transformed into specialty chemicals like fuels, solvents, monomers for polymers, plasticizers, surfactants, agrochemicals, and pharmaceuticals. Over the past three decades, an enormous amount of research data have been acquired on the preparation and downstream value addition of LA, and these works have been reviewed. However, considering the astonishing number of publications appearing every year on LA derivatives, the periodical review of recent works focusing on unique aspects of chemistry must be undertaken to critically evaluate the achievements to date, reassess the challenges, and recognize new opportunities. This review discusses the chemical‐catalytic synthesis of various derivatives of LA by focusing on its functionalities and reactivity patterns. Recent literature on some crucial derivatives such as γ‐valerolactone, 4,4’‐diphenolic acid, and ethyl levulinate have been tabulated and discussed. The synthetic interconversion between various derivatives, mechanistic insights, critical analysis of the reaction parameters toward selective preparation of various derivatives, and their potential commercial applications have been elaborated using predominantly heterogeneous catalysts. A critical assessment of the relative advantages and shortcomings of the existing synthetic strategies for various derivatives of LA has been presented to enkindle fresh ideas.

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“…[139] studied the solvent-free conversion of LA to 2-MTHF over Co/silica catalysts by applying a flow-through fixed-2 total pressure in the steady state, GVL was on activity was high enough to cleave the GVL ring and obtain 2-MTHF with 70% yield. On the other hand, Xie et al [140] showed that a bimetallic Cu-Ni/Al2O3-ZrO2 catalysts can selectively hydrogenate LA to 2-MTHF using 30 bar H2…”

Section: Because Of the Low Melting Point And Low Viscosity (185 Cp mentioning

confidence: 99%

Contribution to the production and use of biomass-derived solvents – a review

et al. 2020

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In this review key processes for the synthesis of greener or more sustainable solvents derived from renewable sources (saccharides, lignocellulose and triglycerides) are discussed. It is shown that a series of platform chemicals such as glycerol, levulinic acid and furans can be converted into a variety of solvents through catalytic transformations that include hydrolysis, esterification, reduction and etherification reactions. It was also considered several aspects of each class of solvent regarding performance within the context of the reactions or extractions for which it is employed.

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Highly efficient hydrogenation of levulinic acid into 2-methyltetrahydrofuran over Ni–Cu/Al₂O₃–ZrO₂bifunctional catalysts

Abstract: High-performance bifunctional catalysts (Ni–Cu/Al2O3–ZrO2) have been investigated in the selective hydrogenolysis of levulinic acid into 2-methyltetrahydrofuran.

Cited by 70 publications

References 38 publications

Catalytic Reductive Alcohol Etherifications with Carbonyl‐Based Compounds or CO₂ and Related Transformations for the Synthesis of Ether Derivatives

Catalytic Reductive Alcohol Etherifications with Carbonyl‐Based Compounds or CO₂ and Related Transformations for the Synthesis of Ether Derivatives

Recent Advances in the Value Addition of Biomass‐Derived Levulinic Acid: A Review Focusing on its Chemical Reactivity Patterns

Contribution to the production and use of biomass-derived solvents – a review

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Highly efficient hydrogenation of levulinic acid into 2-methyltetrahydrofuran over Ni–Cu/Al2O3–ZrO2bifunctional catalysts

Abstract: High-performance bifunctional catalysts (Ni–Cu/Al2O3–ZrO2) have been investigated in the selective hydrogenolysis of levulinic acid into 2-methyltetrahydrofuran.

Cited by 70 publications

References 38 publications

Catalytic Reductive Alcohol Etherifications with Carbonyl‐Based Compounds or CO2 and Related Transformations for the Synthesis of Ether Derivatives

Catalytic Reductive Alcohol Etherifications with Carbonyl‐Based Compounds or CO2 and Related Transformations for the Synthesis of Ether Derivatives

Recent Advances in the Value Addition of Biomass‐Derived Levulinic Acid: A Review Focusing on its Chemical Reactivity Patterns

Contribution to the production and use of biomass-derived solvents – a review

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Highly efficient hydrogenation of levulinic acid into 2-methyltetrahydrofuran over Ni–Cu/Al₂O₃–ZrO₂bifunctional catalysts

Catalytic Reductive Alcohol Etherifications with Carbonyl‐Based Compounds or CO₂ and Related Transformations for the Synthesis of Ether Derivatives

Catalytic Reductive Alcohol Etherifications with Carbonyl‐Based Compounds or CO₂ and Related Transformations for the Synthesis of Ether Derivatives