Catalytic cascade conversion of furfural to 1,4-pentanediol in a single reactor

Liu, Fei; Liu, Qiaoyun; Xu, Jinming; Li, Lei; Cui, Yi‐Tao; Lang, Rui; Lin, Lijin; Su, Yang; Miao, Shu; Sun, Hui; Qiao, Botao; Wang, Aiqin; Jérôme, François; Zhang, Tao

doi:10.1039/c8gc00039e

Cited by 83 publications

(50 citation statements)

References 39 publications

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“…The kinetic profiles of catalyitic reaction of 2-MeTF over supported Ni-Sn(3.0)/AlOH alloy catalyst are shown in Figure 7. It can be observed that 2-MeTF conversion increased gradually as a function of reaction time and achieved after a reaction time of 12 h. At earlier time, the products were dominated by 2H2MeTHF with maximum 21% in yield (after 2 h) then decreased gradually as the reaction time prolonged to reach almost constant after reaction time was extended up to 16 h. Meanwhile the amount of 2-MeTHF and 1,4-PeD was almost equal indicating the hydrogenation and hydrolysis of double bond of furang ring occurred in parallel as indicated in the previous reports [10,14,[39][40][41][42]. As the reaction times were prolonged, yield 1,4-PeD also increased smoothly to reach maximum 64% in yield after 12 h and then gradually decreased after a reaction time of 14 h. On the other hand, yield of 2-MeTHF increased gradually after the reaction time was extended up to 16 h.…”

Section: Kineticssupporting

confidence: 60%

“…NH3-TPD measurements show the differences in the surface acidity (e.g., part of strong acid, >923 K) between AlOH or -Al2O3 and AC supports ( Figure 4 and Table 1). The strong acid site may able to interact with C=C bond of furan ring, protonated, and then hydrolysed in presence of ethanol/H2O [40][41][42][43]. Note to be important that over AlOH or -Al2O3 supported Ni-Sn(3.0) catalysts, no side polymerization product was observed within the reactions.…”

Section: Catalyst Screeningmentioning

confidence: 99%

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Selective Conversion of 2-Methylfuran to 1,4-Pentanediol Catalyzed by Bimetallic Ni-Sn Alloy

Rodiansono

Astuti

Husain

et al. 2019

Bull. Chem. React. Eng. Catal.

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The selective conversion of 2-methylfuran (2-MeF) to 1,4-pentanediol (1,4-PeD) over bimetallic nickeltin alloy catalysts in the ethanol/H2O solvent mixture was studied. By using bulk Ni-Sn(x); x = 3.0 and 1.5 catalysts, a maximum yield of 1,4-PeD (49%) was obtained at 94% conversion of 2-MeF. The dispersion of Ni-Sn(x) on the aluminium hydroxide (AlOH) or -Al2O3 supports allowed to an outstanding yield of 1,4-PeD (up to 64%) at 433 K, 3.0 MPa of H2 within 12 h. Ni-Sn(3.0)/AlOH catalyst was found to be reusable and the treatment of the recovered Ni-Sn(3.0)/AlOH catalyst with H2 at 673 K for 1 h restored the catalyst's original activity and selectivity.

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Section: Kineticssupporting

confidence: 60%

Section: Catalyst Screeningmentioning

confidence: 99%

Selective Conversion of 2-Methylfuran to 1,4-Pentanediol Catalyzed by Bimetallic Ni-Sn Alloy

Rodiansono

Astuti

Husain

et al. 2019

Bull. Chem. React. Eng. Catal.

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“…Depending on the process conditions [11], the nature of the catalyst [12], and the type of the solvent [13], furfural hydrogenation proceeds through various pathways and with the formation of a significant number of products. A variety of heterogeneous catalysts mainly based on Pd [14,15], Pt [16], Ni [17], Cu [18], and Ru [19]. supported on carbon [20], titanium oxide [21], alumina [22], silica.…”

Section: Introductionmentioning

confidence: 99%

Capping Agent Effect on Pd-Supported Nanoparticles in the Hydrogenation of Furfural

et al. 2019

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The catalytic performance of a series of 1 wt % Pd/C catalysts prepared by the sol-immobilization method has been studied in the liquid-phase hydrogenation of furfural. The temperature range studied was 25–75 °C, keeping the H2 pressure constant at 5 bar. The effect of the catalyst preparation using different capping agents containing oxygen or nitrogen groups was assessed. Polyvinyl alcohol (PVA), polyvinylpyrrolidone (PVP), and poly (diallyldimethylammonium chloride) (PDDA) were chosen. The catalysts were characterized by ultraviolet-visible spectroscopy (UV-Vis), Fourier transform infrared spectroscopy (FTIR), transmission electron microscopy (TEM), and X-ray photoelectron spectroscopy (XPS). The characterization data suggest that the different capping agents affected the initial activity of the catalysts by adjusting the available Pd surface sites, without producing a significant change in the Pd particle size. The different activity of the three catalysts followed the trend: PdPVA/C > PdPDDA/C > PdPVP/C. In terms of selectivity to furfuryl alcohol, the opposite trend has been observed: PdPVP/C > PdPDDA/C > PdPVA/C. The different reactivity has been ascribed to the different shielding effect of the three ligands used; they influence the adsorption of the reactant on Pd active sites.

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“…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. Numerous studies on furfural hydrogenation have been published due to the attractive and broad range of applications of the aforementioned furfural-based compounds.…”

mentioning

confidence: 99%

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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Catalytic cascade conversion of furfural to 1,4-pentanediol in a single reactor

Abstract: The selective transformation of furfural to 1,4-pentanediol has been achieved with up to 90% yield in a CO2/H2/H2O system over Ru catalytic species supported on a mesoporous carbon.

Cited by 83 publications

References 39 publications

Selective Conversion of 2-Methylfuran to 1,4-Pentanediol Catalyzed by Bimetallic Ni-Sn Alloy

Selective Conversion of 2-Methylfuran to 1,4-Pentanediol Catalyzed by Bimetallic Ni-Sn Alloy

Capping Agent Effect on Pd-Supported Nanoparticles in the Hydrogenation of Furfural

Recent Advances in Catalytic Hydrogenation of Furfural

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