High Yield Conversion of Residual Pentoses into Furfural via Zeolite Catalysis and Catalytic Hydrogenation of Furfural to 2-Methylfuran

Lessard, Jean; Morin, Jean‐François; Wehrung, Jean-François; Magnin, Delphine; Chornet, E.

doi:10.1007/s11244-010-9568-7

Cited by 129 publications

(82 citation statements)

References 7 publications

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“…Other homogeneous catalysts containing Lewis acid such as CrCl 2 and LiBr [38] gave a furfural yield about 60%, but there were disadvantages of homogeneous catalysts, such as the difficulty of separation and recycle, and these limitations provoked the focus on heterogeneous catalysts because they are recyclable and environmentally friendly. Lessard et al [39] got a 98% furfural yield, but the required temperature was really high (260 • C). Agirrezabal et al [40] and Bhaumik et al [41] also achieved a high furfural yield (more than 80%) but it required a long reaction time.…”

Section: Effect Of Reaction Temperature and Timementioning

confidence: 99%

SO42−/Sn-MMT Solid Acid Catalyst for Xylose and Xylan Conversion into Furfural in the Biphasic System

Lin

Wang

et al. 2017

Catalysts

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Abstract:A sulphated tin ion-exchanged montmorillonite (SO 4 2− /Sn-MMT) was successfully prepared by the ion exchange method of montmorillonite (MMT) with SnCl 4 , followed by the sulphation. This catalysis was applied as a solid acid catalyst for the heterogeneous catalytic transformations of xylose and xylan into furfural in the bio-based 2-methyltetrahydrofuran/H 2 O biphasic system. These prepared catalysts were characterized by X-ray powder diffraction (XRD), Fourier transform infrared spectroscopy (FTIR), temperature programmed desorption of ammonia (NH 3 -TPD), pyridine adsorbed Fourier transform infrared spectroscopy (Py-FTIR), element analysis (EA) and Brunauer-Emmett-Teller (BET) method. Their catalytic performance for xylose and xylan into furfural was also investigated. The reaction parameters such as the initial xylose and xylan concentration, the amounts of catalyst, the organic-to-aqueous phase volume ratio, the reaction temperature and time were studied to optimize the reaction conditions. Results displayed that SO 4 2− /Sn-MMT contained both Brønsted acid and Lewis acid sites, and SO 4 2− ions were contributive to the formation of stronger Brønsted acid sites, which could improve the reaction efficiency. Reaction parameters had significant influence on the furfural production. The substitution of water by the saturated NaCl solution in the aqueous phase also had an important effect on the xylose and xylan conversion. The highest furfural yields were achieved up to 79.64% from xylose and 77.35% from xylan under the optimized reaction conditions (160 • C, 120 min; 160 • C, 90 min). Moreover, the prepared catalyst was stable and was reused five times with a slight decrease (10.0%) of the furfural yield.

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Section: Effect Of Reaction Temperature and Timementioning

confidence: 99%

SO42−/Sn-MMT Solid Acid Catalyst for Xylose and Xylan Conversion into Furfural in the Biphasic System

Lin

Wang

et al. 2017

Catalysts

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“…The system could be operated continuously for 20 h without loss of catalyst activity (Scheme 3 c). [74] A related continuous-flow procedure was adopted for the enantioselective synthesis of bicycle- [75] and the microtubule inhibitor (+)-chamaecypanone C. [76] A continuous process was established for the production of 2,2,6,6-tetramethylpiperidin-4-ol over Cu-Cr/g-Al 2 O 3 in a fixedbed reactor (Scheme 4 a). While the selectivity decreased from 98 % at 98 8C to 77 % at 152 8C, it increased from 75 % to 92 % with the increase of hydrogen pressure from 10 bar to 40 bar.…”

Section: Carbonyl Group Hydrogenationmentioning

confidence: 99%

Heterogeneous Catalytic Hydrogenation Reactions in Continuous‐Flow Reactors

2011

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Microreactor technology and continuous flow processing in general are key features in making organic synthesis both more economical and environmentally friendly. Heterogeneous catalytic hydrogenation reactions under continuous flow conditions offer significant benefits compared to batch processes which are related to the unique gas-liquid-solid triphasic reaction conditions present in these transformations. In this review article recent developments in continuous flow heterogeneous catalytic hydrogenation reactions using molecular hydrogen are summarized. Available flow hydrogenation techniques, reactors, commonly used catalysts and examples of synthetic applications with an emphasis on laboratory-scale flow hydrogenation reactions are presented.

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“…[8,11,12] Only a few catalysts have been reported to be selective for hydrogenation of FFR to FFA [9,13] or for hydrogenolysis of FFR or FFA to 2-MF. [12,14,15] Depending on the catalyst used, vapor phase hydrogenation of FFR yields not only the desired products but also a variety of byproducts, including furan, tetrahydrofuran, and even ring-opening products, such as pentanols and pentanediols (equation (1)): [16] While copper chromite catalysts are most often employed in industry, [1,6] disposal of deactivated copper chromite catalysts in landfill sites is restricted by new environmental regulations because of the high toxicity of Cr. Hence there is strong incentive for the development of new Cr-free catalysts that exhibit high selectivity for FFA and 2-MF formation.…”

Section: Introductionmentioning

confidence: 99%

Hydrogenation and hydrogenolysis of furfural and furfuryl alcohol catalyzed by ruthenium(II) bis(diimine) complexes

Gowda

Parkin

Ladipo

2012

Applied Organom Chemis

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The catalytic activity of ruthenium(II) bis(diimine) complexes cis-[Ru(6,6′-Cl 2 bpy) 2 (OH 2 ) 2 ](Z) 2 (1, Z = CF 3 SO 3 ; 2, Z = (3,5-(CF 3 ) 2 C 6 H 3 ) 4 B, i.e. BArF) and cis-[Ru(4,4′-Cl 2 bpy) 2 (OH 2 ) 2 ](Z) 2 (3, Z = CF 3 SO 3 ; 4, Z = BArF) for the hydrogenation and/or the hydrogenolysis of furfural (FFR) and furfuryl alcohol (FFA) was investigated. The molecular structures of cis-[Ru(4,4′-Cl 2 bpy) 2 (CH 3 CN) 2 ](CF 3 SO 3 ) 2 (3′) and dimeric cis-[(Ru(4,4′-Cl 2 bpy) 2 Cl) 2 ](BArF) 2 (5) were characterized by X-ray crystallography. The structures are consistent with the anticipated reduction in steric hindrance about the ruthenium centers in comparison with corresponding complexes containing 6,6′-Cl 2 bpy ligands. While compounds 1-4 are all active and highly selective catalysts for the hydrogenation of FFR to FFA under modest reaction conditions, 3 and 4 showed decreased activity. This is best explained in terms of reduced Lewis acidity of the Ru 2+ centers and reduced steric hindrance about the metal centers of catalysts 3 and 4. cis-[Ru(6,6′-Cl 2 bpy) 2 (OH 2 ) 2 ](BArF) 2 (2) also displayed high catalytic efficiency for the hydrogenation of FFA to tetrahydrofurfuryl alcohol. Presumably, this is because coordination of C=C bonds of FFA to the ruthenium center is poorly inhibited by non-coordinating BArF counterions. Interestingly, cis-[Ru(6,6′-Cl 2 bpy) 2 (OH 2 ) 2 ] (CF 3 SO 3 ) 2 (1) showed some catalytic activity in ethanol for the hydrogenolysis of FFA to 2-methylfuran, albeit with fairly modest selectivity. Nonetheless, these results indicate that ruthenium(II) bis(diimine) complexes need to be further explored as catalysts for the hydrogenolysis of C-O bonds of FFR, FFA, and related compounds.

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High Yield Conversion of Residual Pentoses into Furfural via Zeolite Catalysis and Catalytic Hydrogenation of Furfural to 2-Methylfuran

Cited by 129 publications

References 7 publications

SO42−/Sn-MMT Solid Acid Catalyst for Xylose and Xylan Conversion into Furfural in the Biphasic System

SO42−/Sn-MMT Solid Acid Catalyst for Xylose and Xylan Conversion into Furfural in the Biphasic System

Heterogeneous Catalytic Hydrogenation Reactions in Continuous‐Flow Reactors

Hydrogenation and hydrogenolysis of furfural and furfuryl alcohol catalyzed by ruthenium(II) bis(diimine) complexes

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