One-Pot Transformation of Levulinic Acid to 2-Methyltetrahydrofuran Catalyzed by Pt–Mo/H-β in Water

Mizugaki, Tomoo; Togo, Keito; Maeno, Zen; Mitsudome, Takato; Jitsukawa, Koichiro; Kaneda, Kiyotomi

doi:10.1021/acssuschemeng.6b00181

Cited by 74 publications

(57 citation statements)

References 32 publications

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“…However, 10 % MTHF yield was obtained in 1‐butanol (1‐BuOH), and nearly complete GVL conversion and 46 % MTHF yield were obtained in 2‐propanol (2‐PrOH) . Conversely, high PDO and MTHF yields were reported in aqueous reactions using noble metal based catalysts, emphasizing that further studies are required to fully understand this complex reaction. The production of MTHF utilizing FA as hydrogen source has also been reported.…”

Section: Figurementioning

confidence: 99%

The Role of the Hydrogen Source on the Selective Production of γ‐Valerolactone and 2‐Methyltetrahydrofuran from Levulinic Acid

et al. 2016

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A mechanistic study of the hydrogenation reaction of levulinic acid (LA) to 2-methyltetrahydrofuyran (MTHF) was performed using three different solvents under reactive H2 and inert N2 atmospheres. Under the applied reaction conditions, catalytic transfer hydrogenation and hydrogenation with molecular H2 were effective at producing high yields of γ-valerolactone. However, the conversion of this stable intermediate to MTHF required the combination of both hydrogen sources (the solvent and the H2 atmosphere) to achieve good yields. The reaction system with 2-propanol as solvent and Ni-Cu/Al2 O3 as catalyst allowed full conversion of LA and a MTHF yield of 80 % after 20 h reaction time at 250 °C and 40 bar of H2 (at room temperature). The system showed the same catalytic activity at LA feed concentrations of 5 and up to 30 wt%, and also when high acetone concentration at the beginning of the reaction were added, which confirmed the potential industrial applications of this solvent/catalyst system.

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Section: Figurementioning

confidence: 99%

The Role of the Hydrogen Source on the Selective Production of γ‐Valerolactone and 2‐Methyltetrahydrofuran from Levulinic Acid

et al. 2016

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“…Levulinic acid (LA) is a platform chemical, the production of which has been paid increasing attention due to its extensive applications as a raw material/additive in cosmetic, medical, and fuel industries . Furthermore, LA can be upgraded to other valuable chemicals such as γ‐valerolactone, levulinic esters, 1,4‐pentanediol, and other value‐added chemicals that can be used in agricultural and cosmetic sectors . LA can be produced from hydrolysis of C6 or C5 sugars, the intermediate products from the hydrolysis of cellulose or hemicellulose in biomass .…”

Section: Introductionmentioning

confidence: 99%

Sulfated Zirconia with Different Crystal Phases for the Production of Ethyl Levulinate and 5‐Hydroxymethylfurfural

Shao

Sun

et al. 2019

Energy Tech

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Distinct crystal phases of an oxide affect the configuration of surface atoms, which might further affect coordination with sulfate during sulfonation for the preparation of SO42−/MxOy type of acid catalyst. Herein, such an effect is investigated with zirconia of the tetragonal or monoclinic phase as the model catalysts. The results show that sulfonation inhibits the transformation of zirconia from the tetragonal phase to the monoclinic phase, whereas the varied phase of zirconia also affects the bonding patterns of sulfate species with zirconia in sulfonation. The sulfated zirconia of monoclinic phase contains more abundant acidic sites and more Brønsted acid sites than that of sulfated zirconia of tetragonal phase. Consequently, the sulfated zirconia of monoclinic phase is more active than the sulfated zirconia of tetragonal phase for the conversion of furfuryl alcohol in ethanol and conversion of fructose in dimethyl sulfoxide, achieving the yield of ethyl levulinate of 96.4% and a high yield of 5‐hydroxymethylfurfural. The sulfated zirconia is not stable in protic solvent due to the leaching of sulfur species and the change in configurations of the sulfate species and the zirconium species, but in the aprotic solvent, they show good stability and recyclability.

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“…Concerning the other possible route, the presence of 2-MeTHF was reported for the first time as a by-product of the LA hydrogenation with CuCr 2 O 3 [35]. Afterward, many works have been published on this topic, which have partially clarified the reaction mechanism, and significantly improved the catalytic performances for the synthesis of 2-MeTHF [36][37][38][39][40][41][42][43][44][45]. Two reaction mechanisms have been proposed for 2-MeTHF synthesis from LA, the first one occurring by LA dehydration via angelicalactone (AGL) (path A, Scheme 1), whereas the second one by LA hydrogenation to 4-hydroxypentanoic acid (HPA) (path B, Scheme 1), both reported in Scheme 1.…”

Section: Introductionmentioning

confidence: 99%

Cascade Strategy for the Tunable Catalytic Valorization of Levulinic Acid and γ-Valerolactone to 2-Methyltetrahydrofuran and Alcohols

et al. 2018

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A cascade strategy for the catalytic valorization of aqueous solutions of levulinic acid as well as of γ-valerolactone to 2-methyltetrahydrofuran or to monoalcohols, 2-butanol and 2-pentanol, has been studied and optimized. Only commercial catalytic systems have been employed, adopting sustainable reaction conditions. For the first time, the combined use of ruthenium and rhenium catalysts supported on carbon, with niobium phosphate as acid co-catalyst, has been claimed for the hydrogenation of γ-valerolactone and levulinic acid, addressing the selectivity to 2-methyltetrahydrofuran. On the other hand, the use of zeolite HY with commercial Ru/C catalyst favors the selective production of 2-butanol, starting again from γ-valerolactone and levulinic acid, with selectivities up to 80 and 70 mol %, respectively. Both levulinic acid and γ-valerolactone hydrogenation reactions have been optimized, investigating the effect of the main reaction parameters, to properly tune the catalytic performances towards the desired products. The proper choice of both the catalytic system and the reaction conditions can smartly switch the process towards the selective production of 2-methyltetrahydrofuran or monoalcohols. The catalytic system [Ru/C + zeolite HY] at 200 • C and 3 MPa H 2 is able to completely convert both γ-valerolactone and levulinic acid, with overall yields to monoalcohols of 100 mol % and 88.8 mol %, respectively.

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One-Pot Transformation of Levulinic Acid to 2-Methyltetrahydrofuran Catalyzed by Pt–Mo/H-β in Water

Cited by 74 publications

References 32 publications

The Role of the Hydrogen Source on the Selective Production of γ‐Valerolactone and 2‐Methyltetrahydrofuran from Levulinic Acid

The Role of the Hydrogen Source on the Selective Production of γ‐Valerolactone and 2‐Methyltetrahydrofuran from Levulinic Acid

Sulfated Zirconia with Different Crystal Phases for the Production of Ethyl Levulinate and 5‐Hydroxymethylfurfural

Cascade Strategy for the Tunable Catalytic Valorization of Levulinic Acid and γ-Valerolactone to 2-Methyltetrahydrofuran and Alcohols

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