On the role of water in selective hydrogenation of cinnamaldehyde to cinnamyl alcohol on PtFe catalysts

Dai, Yihu; Gao, Xing; Chu, Xiaofang; Jiang, Chunyang; Yao, Yao; Guo, Zhen; Zhou, Chunmei; Wang, Chuan; Wang, Hongming; Yang, Yanhui

doi:10.1016/j.jcat.2018.05.008

Cited by 98 publications

(64 citation statements)

References 63 publications

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“…CAL on catalyst surface site via C=O a preference hydrogenation reaction step, leading to an accelerated reaction kinetics and improved COL selectivity. [6] The achieved performance of Fe 0.5 Co@NC under these conditions is the best among the reported high performance catalysts for SH of CAL in water (Supporting Information, Tables S2, S3). Impressively, when a high CAL concentration of 5 mmol in water was used, a high CAL conversion of 97.9 % with a high COL selectivity of 90.5 % can still be attained (Supporting Information, Table S4).…”

Section: Communicationsmentioning

confidence: 84%

Fe‐Co Alloyed Nanoparticles Catalyzing Efficient Hydrogenation of Cinnamaldehyde to Cinnamyl Alcohol in Water

et al. 2020

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Selective hydrogenation of C=O against the conjugated C=C in cinnamaldehyde (CAL) is indispensable to produce cinnamyl alcohol (COL). Nonetheless, it is challenged by the low selectivity and the need to use organic solvents. Herein, for the first time, we report the use of Fe‐Co alloy nanoparticles (NPs) on N‐doped carbon support as a selective hydrogenation catalyst to efficiently convert CAL to COL. The resultant catalyst with the optimized Fe/Co ratio of 0.5 can achieve an exceptional COL selectivity of 91.7 % at a CAL conversion of 95.1 % in pure water medium under mild reaction conditions, ranking it the best performed catalyst reported to date. The experimental results confirm that the COL selectivity and CAL conversion efficiency are, respectively promoted by the presence of Fe and Co, while the synergism of the alloyed Fe‐Co is the key to concurrently achieve high COL selectivity and CAL conversion efficiency.

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Section: Communicationsmentioning

confidence: 84%

Fe‐Co Alloyed Nanoparticles Catalyzing Efficient Hydrogenation of Cinnamaldehyde to Cinnamyl Alcohol in Water

et al. 2020

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“…This is likely due to the strong interactions/ possible hydrogen-bond formations of H 2 O with C=O and catalyst surface site that makes the selective adsorption of CAL on catalyst surface site via C=O a preference hydrogenation reaction step, leading to an accelerated reaction kinetics and improved COL selectivity. [6] The achieved performance of Fe 0.5 Co@NC under these conditions is the best among the reported high performance catalysts for SH of CAL in water (Supporting Information, Tables S2, S3). Impressively, when a high CAL concentration of 5 mmol in water was used, a high CAL conversion of 97.9 % with a high COL selectivity of 90.5 % can still be attained (Supporting Information, Table S4).…”

mentioning

confidence: 84%

Fe‐Co Alloyed Nanoparticles Catalyzing Efficient Hydrogenation of Cinnamaldehyde to Cinnamyl Alcohol in Water

Han

Gong

et al. 2020

Angewandte Chemie

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“…The hydrogenation of methyl benzoate, monomethyl terephthalate and dioctyl phthalate resulted in the formation of the aromatic hydrogenated products using Pt/TiO 2 as catalyst ( Table 3, entry [11][12][13]. It should be mentioned that Pt/TiO 2 could also catalyze the hydrogenation of terephthalic acid, phthalic acid, iso-phthalic acid and even the challenging trimesic acid and trimethyl trimesate to corresponding aromatic ring saturated product under mild conditions, further demonstrating the high e ciency of Pt/TiO 2 for the hydrogenation of aromatic acids (Table 3, entry [14][15][16][17][18]. The hydrogenation of dioctyl phthalate/phthalate acid and trimesic acid/trimethyl trimesate respectively produced the trans and cis isomers, and the hydrogenation of the other substrates investigated in this paper resulted in the formation of cis isomer as the main product on the basis of NMR analysis (see SI), which may be caused by the steric hindrance effect [56].…”

Section: The Role Of the Carboxyl Groupmentioning

confidence: 99%

“…The typical solvation effect is possibly related with the preferential adsorption of aromatic ring on metal surface induced by the interaction of carboxyl group with H 2 O molecules [13,14] and the participation of H* from the dissociated H 2 O molecules in the reaction [2,15]. Though water could modify the adsorption mode of substrates, it may also block the surface active sites [16,17].…”

Section: Introductionmentioning

confidence: 99%

Pt/TiO2 Catalyzed Hydrogenation of Benzoic Acid with Unprecedented High Activity

Guo

Kong

et al. 2020

Preprint

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The hydrogenation of benzoic acid (BA) to corresponding cyclohexanecarboxylic acid has important industry and academia significance, however, the electron deficient aromatic ring and the catalyst “poison” by carboxyl group make BA hydrogenation as one of the most challenging transformations. Herein, we found that Pt NPs deposited on TiO2 were very effective for BA hydrogenation with a record TOF of 4490 h− 1 under 80 oC and 50 bar H2 in hexane, one order higher than the reported results. DFT calculation showed that Pt NPs had a weaker interaction with BA than Ru and Pd NPs commonly used for BA hydrogenation, which improved the toxicity resistance of catalyst to BA. Pt/TiO2 catalysts with electron deficient and electron enriched Pt sites were successfully synthesized by modifying the electron transfer direction between Pt and TiO2. Isotopic experiments suggested the participation of dissociated H from carboxyl group in BA hydrogenation. Consequently, the electron deficient Pt sites with stronger adsorption of BA were more active than electron rich Pt sites in BA hydrogenation. In addition to BA, terephthalic acid, iso-phthalic acid, trimesic acid and other BA derivatives could also be efficiently converted to corresponding aromatic saturated products, demonstrating the wide substrate scope of Pt/TiO2.

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On the role of water in selective hydrogenation of cinnamaldehyde to cinnamyl alcohol on PtFe catalysts

Cited by 98 publications

References 63 publications

Fe‐Co Alloyed Nanoparticles Catalyzing Efficient Hydrogenation of Cinnamaldehyde to Cinnamyl Alcohol in Water

Fe‐Co Alloyed Nanoparticles Catalyzing Efficient Hydrogenation of Cinnamaldehyde to Cinnamyl Alcohol in Water

Fe‐Co Alloyed Nanoparticles Catalyzing Efficient Hydrogenation of Cinnamaldehyde to Cinnamyl Alcohol in Water

Pt/TiO2 Catalyzed Hydrogenation of Benzoic Acid with Unprecedented High Activity

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