Water-enhanced selective hydrogenation of cinnamaldehyde to cinnamyl alcohol on RuSnB/CeO2 catalysts

Dai, Yihu; Chu, Xiaofang; Gu, Jingjing; Gao, Xing; Xu, Min; Lu, Da-Yong; Wan, Xiaoyue; Qi, Wei; Zhang, Bingsen; Yang, Yanhui

doi:10.1016/j.apcata.2019.05.032

Cited by 26 publications

(24 citation statements)

References 71 publications

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“…By analyzing the gases after the Pt 3 Fe/CeO 2 -catalyzed furfural hydrogenation in 20 bar of D 2 and i -PrOH, in situ generated HD product was detected with an approximately 3% yield (relative to D 2 ), indicating that a hydrogen exchange reaction between D 2 gas and i -PrOH as the solvent occurred during the catalytic reaction. It has been reported that the solvent molecule could serve as a bridge to achieve the exchange with dissociated hydrogen species through hydrogen bond network. ,− The high ability for H–D exchange between i -PrOD and FA suggested that their hydrogen bonding interaction might be a crucial factor for the solvation effect of i -PrOH in the Pt 3 Fe/CeO 2 -catalyzed furfural hydrogenation reactions. i -PrOH and water with various ratios were employed to study the effect of the mixture solvent on the catalytic hydrogenation performance.…”

Section: Results and Discussionmentioning

confidence: 99%

Bimetallic PtFe-Catalyzed Selective Hydrogenation of Furfural to Furfuryl Alcohol: Solvent Effect of Isopropanol and Hydrogen Activation

Gao

Tian

Jin

et al. 2020

ACS Sustainable Chem. Eng.

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Highly selective liquid-phase hydrogenation of furfural was efficiently catalyzed by PtFe alloy nanoparticles supported on CeO2. An initial reaction rate at ∼1500 h–1, a near 100% selectivity toward furfuryl alcohol (FA), and a satisfactory recycling stability were achieved on Pt3Fe/CeO2 catalyst. Based on the well-established knowledge of the modification effects of Fe additives on the geometric and electronic properties of Pt sites, this work further demonstrated that the bimetallic PtFe sites could promote H2-activated dissociation for accelerating the hydrogenation reaction in comparison with the monometallic Pt/CeO2 catalyst. The results of isotopic and kinetic experiments to study the solvent effects elucidated that the reaction pathway of catalytic transfer hydrogenation with isopropanol as the hydrogen donor could be ruled out. The results also suggested that isopropanol-involved hydrogen exchange processes with hydrogen and FA could easily occur during the reactions. Furthermore, the furfural hydrogenation could be significantly affected by the solvent intermolecular hydrogen bonding interactions.

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Section: Results and Discussionmentioning

confidence: 99%

Bimetallic PtFe-Catalyzed Selective Hydrogenation of Furfural to Furfuryl Alcohol: Solvent Effect of Isopropanol and Hydrogen Activation

Gao

Tian

Jin

et al. 2020

ACS Sustainable Chem. Eng.

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“…Additionally, hydrogenation of the CC group relative the CO group is thermodynamically preferred by a factor of 35 kJ mol –1 . Therefore, developing highly efficient catalysts for the chemoselective reduction of α,β-unsaturated carbonyl compounds to allylic alcohols is highly desirable. − …”

Section: Introductionmentioning

confidence: 99%

Direct Heterogenization of the Ru-Macho Catalyst for the Chemoselective Hydrogenation of α,β-Unsaturated Carbonyl Compounds

2021

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In this study, a commercially available homogeneous pincer-type complex, Ru-Macho, was directly heterogenized via the Lewis acid-catalyzed Friedel–Crafts reaction using dichloromethane as the cross-linker to obtain a heterogeneous, pincer-type Ru porous organometallic polymer (Ru-Macho-POMP) with a high surface area. Notably, Ru-Macho-POMP was demonstrated to be an efficient heterogeneous catalyst for the chemoselective hydrogenation of α,β-unsaturated carbonyl compounds to their corresponding allylic alcohols using cinnamaldehyde as a model compound. The Ru-Macho-POMP catalyst showed a high turnover frequency (TOF = 920 h–1) and a high turnover number (TON = 2750), with high chemoselectivity (99%) and recyclability during the selective hydrogenation of α,β-unsaturated carbonyl compounds.

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“…Secondly, CAL was extremely insoluble in H 2 O. In Figure a, with the increasing of H 2 O content in ethanol, the absorption peak of UV‐visible absorption curves of CAL redshifted, which could be attributed to the interaction between H 2 O and CAL molecules . Previous studies showed that the λ max of CAL redshifted with increasing solvent polarity .…”

Section: Methodsmentioning

confidence: 80%

Selective Transfer Hydrogenation of Cinnamaldehyde with Alcohol on Amorphous TiO₂ Catalysts: Competitive Adsorption between H₂O and Carbonyl

et al. 2020

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Reduced amorphous TiO2 (A‐TiO2), with high coverage of electrons and protons on its surface, supplies a steady‐state condition for selective hydrogenation reaction. Generally, there are some complex hydrogenation reaction products ascribed to the presence of multiple adsorption modes of cinnamaldehyde (CAL). In our work, the saturated aldehyde (∼48%) and unsaturated alcohol (52%) coexist in the products with a ratio of near 1 : 1, while the saturated alcohol is not produced in the reaction. Furthermore, the presence of H2O could suppress the adsorption of the C=O group while the C=C group could be strongly adsorbed on the surface of A‐TiO2, which results in the high selectivity of HCAL (∼84%). We explain these results by proposing a reaction mechanism with several adsorption modes of CAL affected by the solvents. This discovery also puts forward a new method for promoting the selectivity of COL by removing the H2O in the reaction system.

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Water-enhanced selective hydrogenation of cinnamaldehyde to cinnamyl alcohol on RuSnB/CeO2 catalysts

Cited by 26 publications

References 71 publications

Bimetallic PtFe-Catalyzed Selective Hydrogenation of Furfural to Furfuryl Alcohol: Solvent Effect of Isopropanol and Hydrogen Activation

Bimetallic PtFe-Catalyzed Selective Hydrogenation of Furfural to Furfuryl Alcohol: Solvent Effect of Isopropanol and Hydrogen Activation

Direct Heterogenization of the Ru-Macho Catalyst for the Chemoselective Hydrogenation of α,β-Unsaturated Carbonyl Compounds

Selective Transfer Hydrogenation of Cinnamaldehyde with Alcohol on Amorphous TiO₂ Catalysts: Competitive Adsorption between H₂O and Carbonyl

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Water-enhanced selective hydrogenation of cinnamaldehyde to cinnamyl alcohol on RuSnB/CeO2 catalysts

Cited by 26 publications

References 71 publications

Bimetallic PtFe-Catalyzed Selective Hydrogenation of Furfural to Furfuryl Alcohol: Solvent Effect of Isopropanol and Hydrogen Activation

Bimetallic PtFe-Catalyzed Selective Hydrogenation of Furfural to Furfuryl Alcohol: Solvent Effect of Isopropanol and Hydrogen Activation

Direct Heterogenization of the Ru-Macho Catalyst for the Chemoselective Hydrogenation of α,β-Unsaturated Carbonyl Compounds

Selective Transfer Hydrogenation of Cinnamaldehyde with Alcohol on Amorphous TiO2 Catalysts: Competitive Adsorption between H2O and Carbonyl

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Selective Transfer Hydrogenation of Cinnamaldehyde with Alcohol on Amorphous TiO₂ Catalysts: Competitive Adsorption between H₂O and Carbonyl