Catalytic Conversion of Levulinic Acid and Its Esters to γ-Valerolactone over Silica-Supported Zirconia Catalysts

Kuwahara, Yasutaka; Kaburagi, Wako; Fujitani, Tadahiro

doi:10.1246/bcsj.20140205

Cited by 23 publications

(19 citation statements)

References 34 publications

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“…Secondary alcohols, including 2-propanol and 2-butanol, however, worked as effective hydrogen donors, affording similar γ-valerolactone yield (85.6–88.3%) with high selectivity (higher than 90%) under identical conditions. The reason could be ascribed to the ease of β-hydride elimination from the intermediate alkoxide species during the transfer hydrogenation process. , However, an obvious decreased γ-valerolactone yield was observed when using 2-pentanol as the hydrogen donor, which may be due to the difficulty in intramolecular dealcoholization, thus leading to reduced transfer hydrogenation activity. Therefore, 2-propanol was determined to be the optimum hydrogen donor in the present study.…”

Section: Results and Discussionmentioning

confidence: 99%

Hierarchical FAU-Type Hafnosilicate Zeolite as a Robust Lewis Acid Catalyst for Catalytic Transfer Hydrogenation

Tang

Song

et al. 2019

ACS Sustainable Chem. Eng.

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FAU-type hafnosilicate zeolite with a hierarchical structure (Hf-USY) was constructed through a post-synthesis strategy containing the controlled dealumination of the commercial H-USY zeolite and the subsequent dry impregnation of the Cp 2 HfCl 2 precursor. The incorporation of Hf ions into the zeolite framework involved the interaction between the silanol groups from framework dealumination and Cp 2 HfCl 2 molecules. Characterization results from UV−vis and X-ray photoelectron spectroscopy verified that the incorporated Hf ions mainly existed in the tetrahedrally coordinated form in the zeolite framework. The creation of Lewis acid sites associated with Hf incorporation was confirmed by Fourier transform infrared spectroscopy with pyridine and deuterated acetonitrile adsorption. The as-synthesized Hf-USY zeolite served as a highly efficient catalyst in the transfer hydrogenation of ethyl levulinate to γvalerolactone, outperforming the Sn-and Zr-silicate analogues. The Hf-USY catalyst also exhibited good performance in the transfer hydrogenation of more challenging substrates such as furanic, aromatic, as well as alkene-substituted carbonyl compounds into the corresponding alcohols. The influence of Lewis acid sites, preparation parameters, as well as the hydrogen donor on the catalytic activity of the Hf-USY zeolite was investigated in detail.

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Section: Results and Discussionmentioning

confidence: 99%

Hierarchical FAU-Type Hafnosilicate Zeolite as a Robust Lewis Acid Catalyst for Catalytic Transfer Hydrogenation

Tang

Song

et al. 2019

ACS Sustainable Chem. Eng.

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“…157,158 From Scheme 1 it can be verified that these products are formed further down the cascade reactions of Fur, with GVL as an important end-product. According to the literature, GVL may be formed from LA 155,159,160 or LEs 87,155,156,161 in alcohol media via CTH reaction, in the presence of zirconium-containing catalysts. The catalytic potential of ZrAl-Beta/TUD-1 for GVL production was further investigated using LA and 1-butyl levulinate (1BL) as model substrates (CatLoad=25.7 g cat dm -3 , T=150 C, Figures 10 and 11).…”

Section: Catalytic Studiesmentioning

confidence: 99%

Bulk and composite catalysts combining BEA topology and mesoporosity for the valorisation of furfural

Antunes

Neves

Fernandes

et al. 2016

Catal. Sci. Technol.

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“…Using LA as a reaction substrate, ZrO 2 was supported on typical hexagonal mesoporous Si, such as Mobil Composition of Matter-41 (MCM-41) and Santa Barbara Amorphous-15 (SBA-15) (entry 1, 2, 4 in Table 2) prepared by Kuwahara et al (2014). The silicon carrier itself is inactive, and the reaction kinetics demonstrated that the pore size of mesoporous Si had little effect on the catalytic activity.…”

Section: La and Its Esters As Substratesmentioning

confidence: 99%

Recyclable Zr/Hf-Containing Acid-Base Bifunctional Catalysts for Hydrogen Transfer Upgrading of Biofuranics: A Review

Liu

et al. 2021

Front. Chem.

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The massive burning of a large amount of fossil energy has caused a lot of serious environmental issues (e.g., air pollution and climate change), urging people to efficiently explore and valorize sustainable alternatives. Biomass is being deemed as the only organic carbon-containing renewable resource for the production of net-zero carbon emission fuels and fine chemicals. Regarding this, the selective transformation of high-oxygen biomass feedstocks by catalytic transfer hydrogenation (CTH) is a very promising strategy to realize the carbon cycle. Among them, the important Meerwein-Ponndorf-Verley (MPV) reaction is believed to be capable of replacing the traditional hydrogenation strategy which generally requires high-pressure H2 and precious metals, aiming to upgrade biomass into downstream biochemical products and fuels. Employing bifunctional heterogeneous catalysts with both acidic and basic sites is needed to catalyze the MPV reaction, which is the key point for domino/cascade reaction in one pot that can eliminate the relevant complicated separation/purification step. Zirconium (Zr) and hafnium (Hf), belonging to transition metals, rich in reserves, can demonstrate similar catalytic efficiency for MPV reaction as that of precious metals. This review introduced the application of recyclable heterogeneous non-noble Zr/Hf-containing catalysts with acid-base bifunctionality for CTH reaction using the safe liquid hydrogen donor. The corresponding catalysts were classified into different types including Zr/Hf-containing metal oxides, supported materials, zeolites, metal-organic frameworks, metal-organic hybrids, and their respective pros and cons were compared and discussed comprehensively. Emphasis was placed on evaluating the bifunctionality of catalytic material and the key role of the active site corresponding to the structure of the catalyst in the MPV reaction. Finally, a concise summary and prospect were also provided centering on the development and suggestion of Zr/Hf-containing acid-base bifunctional catalysts for CTH.

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Catalytic Conversion of Levulinic Acid and Its Esters to γ-Valerolactone over Silica-Supported Zirconia Catalysts

Cited by 23 publications

References 34 publications

Hierarchical FAU-Type Hafnosilicate Zeolite as a Robust Lewis Acid Catalyst for Catalytic Transfer Hydrogenation

Hierarchical FAU-Type Hafnosilicate Zeolite as a Robust Lewis Acid Catalyst for Catalytic Transfer Hydrogenation

Bulk and composite catalysts combining BEA topology and mesoporosity for the valorisation of furfural

Recyclable Zr/Hf-Containing Acid-Base Bifunctional Catalysts for Hydrogen Transfer Upgrading of Biofuranics: A Review

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