Liquid phase catalytic transfer hydrogenation of ethyl levulinate to γ-valerolactone over ZrO<sub>2</sub>/SBA-15

Osatiashtiani, Amin; Orr, Samantha A.; Durndell, Lee J.; García, Irene Collado; Merenda, Andrea; Lee, Adam F.; Wilson, Karen

doi:10.1039/d2cy00538g

Cited by 8 publications

(2 citation statements)

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“…[29] and high activity for carboxylic acid esterification, [30] including of LA formed in-situ from glucose. [31] Our recent work on ZrO 2 /SBA-15 identified this as efficient for the continuous flow CTH of ethyl levulinate CTH to GVL, [32] and hence this was chosen as the (predominantly) Lewis acid catalyst. The optimum catalyst selections delivered a high and stable GVL yield of 80 % at 150 °C in flow, significantly higher than either individual catalyst in flow or a physical mixture in batch.…”

Section: Chemcatchemmentioning

confidence: 99%

Continuous flow (Sulfated) Zirconia Catalysed Cascade Conversion of Levulinic Acid to γ‐Valerolactone

et al. 2023

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γ-Valerolactone (GVL) is a renewable and versatile platform chemical derived from sustainable carbon feedstocks. The cascade conversion of levulinic acid into GVL requires Brønsted and Lewis acid catalysed reactions. Here, a dual-catalyst bed configuration is demonstrated that promotes synergy between Brønsted acid sites in sulfated zirconia (SZ) and Lewis acid sites in ZrO 2 /SBA-15 for the liquid phase, continuous flow esterification and subsequent catalytic transfer hydrogenation (CTH) of levulinic acid to GVL. A saturated surface sulfate monolayer, possessing a high density of strong Brønsted acid sites, was optimal for levulinic acid esterification to isopropyl levulinate over SZ (> 80 % conversion). A conformal ZrO 2 bilayer, deposited over a SBA-15 mesoporous silica and possessing mixed Brønsted:Lewis acidity, catalysed CTH of the levulinate ester and subsequent dealcoholisation/cyclisation to GVL (> 60 % selectivity). Maximum stable productivity for the dual-bed was 2.2 mmol GVL .g cat .h À 1 at 150 °C, significantly outperforming either catalyst alone or a physical mixture of both. Flow chemistry is a versatile approach to achieve spatial control over cascade transformations involving distinct catalytically active sites.

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Section: Chemcatchemmentioning

confidence: 99%

Continuous flow (Sulfated) Zirconia Catalysed Cascade Conversion of Levulinic Acid to γ‐Valerolactone

et al. 2023

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“…Because of advantages in terms of cost and reagent safety, continuous reduction via catalytic hydrogen transfer has also been also reported. In-flow transfer hydrogenation (TH) reactions have already been reported for the reduction of ketones and imines, − olefins, − and levulinates − in order to obtain high-value products, while several studies reported the TH reactions of nitrobenzenes under continuous flow. Based on our knowledge, hydrides have been studied as hydrogen donors in large excess, Au/NaBH 4 and Pd/NaBH 4 have been reported in this field, and Pd/C has been also used with a large excess of ammonium formate and of cyclohexene .…”

Section: Introductionmentioning

confidence: 99%

Copper-Catalyzed Continuous-Flow Transfer Hydrogenation of Nitroarenes to Anilines: A Scalable and Reliable Protocol

Martina,

Moran,

Manzoli

et al. 2023

Org. Process Res. Dev.

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A robust supported catalyst that is made up of copper nanoparticles on Celite has been successfully prepared for the selective transfer hydrogenation of aromatic nitrobenzenes to anilines under continuous flow. The method is efficient and environmentally benign thanks to the absence of hydrogen gas and precious metals. Long-term stability studies show that the catalytic system is able to achieve very high nitrobenzene conversion (>99%) when working for up to 145 h. The versatility of the transfer hydrogenation system has been tested using representative examples of nitroarenes, with moderate-to-excellent yields being obtained. The packed bed reactor (PBR) permits the use of a setup that can provide products via simple isolation by SPE without the need for further purification. The recovery and reuse of either EG or the ion-exchange resin leads to consistent waste reduction; therefore, E-factor distribution analysis has highlighted the environmental efficiency of this synthetic protocol.

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Magnetic biochar‐supported ZrO₂ as an efficient catalyst for one‐pot synthesis of 1′,4′‐dihydro‐3H,3′H‐spiro[furo[3,4‐b]quinoline‐9,2′‐quinoxaline]‐1,3′(4H)‐diones

Zhang

Dong

et al. 2022

Applied Organom Chemis

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A novel ZrO2 supported on a magnetic biochar material (CoFe2O4/BC‐ZrO2) was synthesized using a relatively simple route. The prepared CoFe2O4/BC‐ZrO2 was characterized by X‐ray diffraction (XRD), Fourier transform infrared (FT‐IR) spectroscopy, scanning electron microscopy (SEM), transmission electron microscopy (TEM), energy‐dispersed X‐ray (EDX) elemental analysis, N2 adsorption–desorption isotherm, thermogravimetric analysis (TGA), and magnetic properties. The CoFe2O4/BC‐ZrO2 showed high catalytic activity for the synthesis of spiro[furo[3,4‐b]quinoline via a one‐pot three‐component reaction of benzene‐1,2‐diamine, indoline‐2,3‐dione, and tetronic acid. The catalyst can be recovered by an external magnetic field and recycled at least five times without significantly reducing its activity.

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Liquid phase catalytic transfer hydrogenation of ethyl levulinate to γ-valerolactone over ZrO₂/SBA-15

Abstract: γ-Valerolactone (GVL) is an important bio-derived platform molecule whose atom- and energy efficient, and scalable, catalytic synthesis is highly desirable. Catalytic transfer hydrogenation (CTH) of ethyl levulinate (EL) to γ-valerolactone...

Cited by 8 publications

References 43 publications

Continuous flow (Sulfated) Zirconia Catalysed Cascade Conversion of Levulinic Acid to γ‐Valerolactone

Continuous flow (Sulfated) Zirconia Catalysed Cascade Conversion of Levulinic Acid to γ‐Valerolactone

Copper-Catalyzed Continuous-Flow Transfer Hydrogenation of Nitroarenes to Anilines: A Scalable and Reliable Protocol

Magnetic biochar‐supported ZrO₂ as an efficient catalyst for one‐pot synthesis of 1′,4′‐dihydro‐3H,3′H‐spiro[furo[3,4‐b]quinoline‐9,2′‐quinoxaline]‐1,3′(4H)‐diones

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Liquid phase catalytic transfer hydrogenation of ethyl levulinate to γ-valerolactone over ZrO2/SBA-15

Abstract: γ-Valerolactone (GVL) is an important bio-derived platform molecule whose atom- and energy efficient, and scalable, catalytic synthesis is highly desirable. Catalytic transfer hydrogenation (CTH) of ethyl levulinate (EL) to γ-valerolactone...

Cited by 8 publications

References 43 publications

Continuous flow (Sulfated) Zirconia Catalysed Cascade Conversion of Levulinic Acid to γ‐Valerolactone

Continuous flow (Sulfated) Zirconia Catalysed Cascade Conversion of Levulinic Acid to γ‐Valerolactone

Copper-Catalyzed Continuous-Flow Transfer Hydrogenation of Nitroarenes to Anilines: A Scalable and Reliable Protocol

Magnetic biochar‐supported ZrO2 as an efficient catalyst for one‐pot synthesis of 1′,4′‐dihydro‐3H,3′H‐spiro[furo[3,4‐b]quinoline‐9,2′‐quinoxaline]‐1,3′(4H)‐diones

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Liquid phase catalytic transfer hydrogenation of ethyl levulinate to γ-valerolactone over ZrO₂/SBA-15

Magnetic biochar‐supported ZrO₂ as an efficient catalyst for one‐pot synthesis of 1′,4′‐dihydro‐3H,3′H‐spiro[furo[3,4‐b]quinoline‐9,2′‐quinoxaline]‐1,3′(4H)‐diones