One-pot conversion of furfural to alkyl levulinate over bifunctional Au-H4SiW12O40/ZrO2 without external H2

Zhu, Shengyun; Cen, Youliang; Guo, Jing; Chai, Jiachun; Wang, Jianguo; Fan, Weibin

doi:10.1039/c6gc01736c

Cited by 66 publications

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References 51 publications

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“…Catalysts 2019, 9, 796 3 of 33 Catalysts 2018, 8, x FOR PEER REVIEW 3 of 36 Scheme 1. Illustrative representation of reaction pathways in furfural hydrogenation.Other downstream products of furfural hydrogenation, such as (tetrahydro)furan [32], tetrahydrofurfural [33], lactones [34][35][36][37], levulinates [38,39], cyclopentanone(l) [40][41][42][43][44][45][46][47][48][49][50][51]. or diols [52][53][54][55], could also be employed as fuel additives, solvents, and platform molecules.…”

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Recent Advances in Catalytic Hydrogenation of Furfural

et al. 2019

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Furfural has been considered as one of the most promising platform molecules directly derived from biomass. The hydrogenation of furfural is one of the most versatile reactions to upgrade furanic components to biofuels. For instance, it can lead to plenty of downstream products, such as (tetrahydro)furfuryl alcohol, 2-methyl(tetrahydro)furan, lactones, levulinates, cyclopentanone(l), or diols, etc. The aim of this review is to discuss recent advances in the catalytic hydrogenation of furfural towards (tetrahydro)furfuryl alcohol and 2-methyl(tetrahydro)furan in terms of different non-noble metal and noble metal catalytic systems. Reaction mechanisms that are related to the different catalytic materials and reaction conditions are properly discussed. Selective hydrogenation of furfural could be modified not only by varying the types of catalyst (nature of metal, support, and preparation method) and reaction conditions, but also by altering the reaction regime, namely from batch to continuous flow. In any case, furfural catalytic hydrogenation is an open research line, which represents an attractive option for biomass valorization towards valuable chemicals and fuels.FA is a very important monomer for the synthesis of furan resins, which are widely used in thermoset polymer matrix composites, cements, adhesives, coatings, and casting/foundry resins. This molecule is also used as a non-reactive diluent for epoxy resin, a modifier for phenolic and urea resins, an oil well, and a carbon binder. Furthermore, the salt of FA is used in the synthesis of lysine, vitamin C, lubricants, and plasticizers [22,23]. Moreover, it should be highlighted that FA is also an important intermediate for the production of further hydrogenation products (as shown in Scheme 1), such as 2-methylfuran (MF), a potential alternative fuel with better combustion performance and higher Research Octane Number (RON = 103) than that of gasoline (RON = 96.8) [24]. In other applications, MF is used in perfume intermediates, chloroquine lateral chains in medical intermediates, and as a raw material for the production of chrysanthemate pesticides [25].Moreover, tetrahydrofurfuryl alcohol (THFA) can be used as a green solvent in the pharmaceutical industry and, in addition, it constitutes an outstanding intermediate to produce dihydropyran [26], pyridine [27], tetrahydrofuran, and pentan-1,5-diol [28][29][30]. Particularly, the latest molecule is an important monomer in the plastics industry. Furthermore, 2-methyltetrahydrofuran (MTHF) is quite engaging for its possible applications in organometallic chemistry, as well as in organic reactions that are related to organocatalysis, biotransformations, and biomass processing [31]. Catalysts 2019, 9, 796 3 of 33 Catalysts 2018, 8, x FOR PEER REVIEW 3 of 36 Scheme 1. Illustrative representation of reaction pathways in furfural hydrogenation.Other downstream products of furfural hydrogenation, such as (tetrahydro)furan [32], tetrahydrofurfural [33], lactones [34][35][36][37], levulinates [38,39], cyclopentanone...

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Recent Advances in Catalytic Hydrogenation of Furfural

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“…Furfural is the most common industrial chemical formed by the decomposition of hemicellulose, and more than 200 000 tons are annually produced . Considering that FAL is routinely synthesized by furfural hydrogenation, the integrated transformation of furfural into AL presents prominent advantages in terms of sustainability and energy efficiency.…”

Section: Integrated Alcoholysis Of Furfural and Cellulosementioning

confidence: 99%

“…With a view to avoiding the use of external hydrogen, we investigated one‐pot synthesis of AL from furfural by a transfer hydrogenation reaction with 2‐propanol (Scheme ) . 2‐Propanol can act as an outstanding reductant and H donor.…”

Section: Integrated Alcoholysis Of Furfural and Cellulosementioning

confidence: 99%

“…Furfural is them ost common industrial chemical formed by the decomposition of hemicellulose, and more than 200 000 tons are annually produced. [53] Considering that FALi s routinelys ynthesized by furfural hydrogenation, the integrated transformationo ff urfural into AL presents prominenta dvantages in terms of sustainability and energy efficiency.Y uana nd co-workersd emonstrated the effective production of AL from furfuralw ith ethanol in the presence of H 2 . [54] The yield of AL reached7 5.6 %a t1 70 8Ca nd 5MPa H 2 over Pt/ZrNbPO 4 ( Table 2, entry 17).…”

Section: Alcoholysis Of Furfuryla Lcohol To Alkyl Levulinatementioning

confidence: 99%

“…With av iew to avoiding the use of externalhydrogen, we investigated one-pot synthesis of AL from furfural by at ransfer hydrogenation reaction with 2-propanol (Scheme 10). [53] 2-Propanol can act as an outstanding reductant and Hdonor. Furfural initially undergoes at ransfer hydrogenation reaction with 2-propanol over metal catalysts, and the formed FALt hen immediately undergoes alcoholysis to AL in the presence of acid sites.…”

Section: Alcoholysis Of Furfuryla Lcohol To Alkyl Levulinatementioning

confidence: 99%

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Alcoholysis: A Promising Technology for Conversion of Lignocellulose and Platform Chemicals

et al. 2017

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In the catalytic conversion of lignocellulose to valuable products, the first entry point is to break down these biopolymers to sugar units or aromatic monomers, which is conventionally achieved by hydrolysis in water medium. Recent years have seen tremendous progress in the alcoholysis process, which has remarkable advantages, such as the avoidance of treating waste water, suppression of humins or chars, and enhancement of reaction rate and product yield. Advances have been focused on the alcoholysis of cellulose, hemicellulose, and lignin to alkyl glucosides, xylosides, and aromatic monomers, respectively. Alcoholysis of the platform molecule furfuryl alcohol (FAL) to alkyl levulinate (AL) and integrated alcoholysis of cellulose and furfural into AL are also summarized. This Minireview highlights the comparisons between alcoholysis and hydrolysis, the reaction mechanism of alcoholysis, and future challenges for industrial applications.

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Levulinate Derivatives – Main Production Routes and Uses of Organic and Inorganic Levulinates Derivatives

2022

Levulinic Acid

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One-pot conversion of furfural to alkyl levulinate over bifunctional Au-H₄SiW₁₂O₄₀/ZrO₂ without external H₂

Abstract: An unprecedented 80.2% yield of alkyl levulinate was obtained via one-pot conversion of furfural with 2-propanol over Au-H4SiW12O40/ZrO2.

Cited by 66 publications

References 51 publications

Recent Advances in Catalytic Hydrogenation of Furfural

Recent Advances in Catalytic Hydrogenation of Furfural

Alcoholysis: A Promising Technology for Conversion of Lignocellulose and Platform Chemicals

Levulinate Derivatives – Main Production Routes and Uses of Organic and Inorganic Levulinates Derivatives

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