Comparative Study of Supported Monometallic Catalysts in the Liquid-Phase Hydrogenation of Furfural: Batch Versus Continuous Flow

Wang, Yantao; Prinsen, Pepijn; Triantafyllidis, Konstantinos S.; Karakoulia, Stamatia A.; Trikalitis, Pantelis N.; Yepez, Alfonso; Len, Christophe; Luque, Rafael

doi:10.1021/acssuschemeng.8b00984

Cited by 64 publications

(44 citation statements)

References 48 publications

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“…For comparison, our research group recently found that Ni/C was selective to MF at 200 • C with H 2 or 260 • C without H 2 in batch conditions; however, in continuous flow regime at 150 • C under 50 bar H 2 , the hydrogenation selectivity was quite poor due to side-reaction between furfural and isopropanol. When altering the solvent with non-protic cyclopentyl methyl ether (CPME), two major products, namely FA and THFA, were obtained [141]. These results gave a clear hint that selective hydrogenation could be achieved by changing the reaction regime and conditions.…”

Section: Co Ni Based Catalystmentioning

confidence: 94%

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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Section: Co Ni Based Catalystmentioning

confidence: 94%

Recent Advances in Catalytic Hydrogenation of Furfural

et al. 2019

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“…[40] We have designed and evaluated the reduction of acetophenone to 1-Phenyl ethanol as model substrate using sodium borohydride and water as a solvent. [41] - [42] 2. Experimental…”

Section: Introductionmentioning

confidence: 99%

Ketone Hydrogenation by Using ZnO−Cu(OH)Cl/MCM‐41 with a Splash of Water: An Environmentally Benign Approach

Choudhary

Ghosh

Mobin

2020

Chemistry An Asian Journal

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MCM-41-supported ZnOÀ Cu(OH)Cl nanoparticles were synthesized via an incipient wetness impregnation technique using zinc chloride and copper chloride salts as well as water at room temperature. The catalyst was characterized by powder X-ray diffraction (PXRD), infrared spectroscopy (IR), and TGA, whereas surface and morphological studies were performed by using scanning electron microscopy (SEM) and transmission electron microscopy (TEM). The above studies revealed the incorporation of metal species into the pores of MCM-41, leading to a decrease in surface area of the nanoparticles that was found to be 239.079 m 2 /g. The substituents attached to the ketone determine the rate of the reaction, and the utilization of the green solvent 'water' astonishingly completes the hydrogenation reaction in 45 minutes at 40°C with 100% conversion and 100% selectivity as analyzed by gas chromatography-mass spectrometry. Hence, ZnOÀ Cu(OH)Cl/MCM-41 nanoparticles with 2.46 wt% zinc and 6.39 wt% copper were demonstrated as an active catalyst for the reduction of ketones without using any gaseous hydrogen source making it highly efficient as well as environmentally and economically benign.

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“…However, after the fourth cycle, the conversion of furfural dropped from 100% to 69% and the selectivity to FOL also decreased (88%). This could be due to the poisoning of cobalt in the solution, as this is already mentioned in the literature, or to the leaching of cobalt, [24,26] leading to the formation of by-products such as THFA and other unidentified by-products. To confirm these hypotheses, TGA analysis of the spent catalyst were performed and compared to the TGA analysis of the fresh catalyst (Figure 4).…”

Section: Hydrogenation Of Furfural In Batch Reactormentioning

confidence: 87%

“…Several drawbacks are present using this system: deactivation due to the sintering of active species; poisoning of the catalyst surface by coke formation; low selectivity of FOL; and high temperature and pressure. Up to now, several studies of selective hydrogenation of furfural to FOL have been performed in the liquid phase in batch reactors using different solvents, but very little attention has been paid to the process in a flow system [22][23][24][25][26]. To this aim, hydrogenation of furfural to FOL was studied in the presence of Co/SiO 2 catalyst in batch and in continuous flow reactors.…”

Section: Methodsmentioning

confidence: 99%

Synthesis of Furfuryl Alcohol from Furfural: A Comparison between Batch and Continuous Flow Reactors

et al. 2020

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Furfural is a platform molecule obtained from hemicellulose. Among the products that can be produced from furfural, furfuryl alcohol is one of the most extensively studied. It is synthesized at an industrial scale in the presence of CuCr catalyst, but this process suffers from an environmental negative impact. Here, we demonstrate that a non-noble metal catalyst (Co/SiO2) was active (100% conversion of furfural) and selective (100% selectivity to furfuryl alcohol) in the hydrogenation of furfural to furfuryl alcohol at 150 °C under 20 bar of hydrogen. This catalyst was recyclable up to 3 cycles, and then the activity decreased. Thus, a comparison between batch and continuous flow reactors shows that changing the reactor type helps to increase the stability of the catalyst and the space-time yield. This study shows that using a continuous flow reactor can be a solution to the catalyst suffering from a lack of stability in the batch process.

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Comparative Study of Supported Monometallic Catalysts in the Liquid-Phase Hydrogenation of Furfural: Batch Versus Continuous Flow

Cited by 64 publications

References 48 publications

Recent Advances in Catalytic Hydrogenation of Furfural

Recent Advances in Catalytic Hydrogenation of Furfural

Ketone Hydrogenation by Using ZnO−Cu(OH)Cl/MCM‐41 with a Splash of Water: An Environmentally Benign Approach

Synthesis of Furfuryl Alcohol from Furfural: A Comparison between Batch and Continuous Flow Reactors

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