Hydrogenation of cinnamaldehyde to cinnamyl alcohol with metal phosphides: Catalytic consequences of product and pyridine doping

Bonita, Yolanda; Jain, Varsha; Geng, Feiyang; O’Connell, Timothy P.; Ramos, Norbert X.; Rai, Neeraj; Hicks, Jason C.

doi:10.1016/j.apcatb.2020.119272

Cited by 40 publications

(37 citation statements)

References 46 publications

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“…[5][6][7] The efficient utilization of CAL is the most critical issue for COL production because large quantities of CAL can only be obtained in an economically viable manner via extraction processes from the bark of cinnamon and other CALcontaining trees with limited nature reserves. Presently, SH of CAL to COL is challenged by the unfavored thermodynamics that leads to low selectivity toward COL. [1,[8][9][10] Also, the use of organic solvent in COL production pollutes the environment and requires post-production separation. For these reasons, the relevant industries have constantly demanded to replace organic solvents with water, however, the development of new catalysts capable of SH of CAL in pure aqueous medium is required.…”

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confidence: 99%

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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confidence: 99%

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

et al. 2020

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“…Cinnamaldehyde (CALD) belongs to the family of α,β-unsaturated aldehydes. Hydrogenation of CALD is an industrially important reaction, involving selective catalytic reduction of C=C and C=O bonds in the presence of molecular hydrogen 1,2 . The reaction produces three main compounds, which are, hydrocinnamaldehyde (HCALD), hydrocinnamyl alcohol (3-phenyl propanol, 3PP) and cinnamyl alcohol (CAL) (Scheme 1) 3 .…”

Section: Introductionmentioning

confidence: 99%

“…However, these catalysts also suffer from poor selectivity. Numerous approaches to enhance the catalyst activity/selectivity have been reported and they, include among others, the use of bimetallic catalysts 13 , variation of support properties and optimization of catalyst particle size and shape 2 .…”

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Vapour phase hydrogenation of cinnamaldehyde using cobalt supported inside and outside hollow carbon spheres

et al. 2022

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The hydrogenation of cinnamaldehyde is usually performed in the liquid phase in batch mode. In this study, a vapour phase flow system has been used to evaluate the use of cobalt catalysts supported inside and outside hollow carbon spheres (HCSs). The influence of temperature, hydrogen flow rate and catalyst mass on the hydrogenation reaction was investigated. The catalysts generally showed modest conversion to the required products, hydrocinnamaldehyde, 3-phenyl propanol, cinnamyl alcohol together with formation of various decomposition products. The data revealed that the Co@HCS showed better conversion and product selectivity compared to the Co/HCS. The catalysts with smaller particle sizes (ca. 6 nm) were more efficient than big particles (30 – 40 nm). An increase in reaction temperature (200 – 300°C) resulted in a lower cinnamaldehyde conversion and a poor product selectivity. TPR studies revealed that the Co@HCSs had a stronger metal-support interaction than the Co/HCSs catalysts. Catalyst recycling studies revealed that only the Co/HCSs could be regenerated (4 cycles) and post reaction analysis of the catalysts revealed that this was due to HCS pore blockage and not Co sintering.

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“…Controlling the bond formation in the catalysis reaction is essential for producing desired chemicals and minimizing by‐products. The selective hydrogenation of α,β‐unsaturated aldehydes to unsaturated alcohols by hydrogenation over C=O bond plays a critical role in synthesizing a large number of fine chemicals used in the production of foods, pharmaceuticals and cosmetics [1,2] . Cinnamaldehyde (CMA) hydrogenation is a typical and important reaction in this family of reactions because one of the selective products from this reaction cinnamyl alcohol (CMO) is highly desired, which is usually used as a significant component in the food and pharmaceutical industries [1–3] .…”

Section: Introductionmentioning

confidence: 99%

“…Besides, CMA can also be transformed into phenyl propanol (HCMO) by complete hydrogenation of C=C bond and C=O bond. As a consequence, these side reactions undoubtedly prohibit the selective generation of CMO [1–4] . Previous reports suggest that the catalysts used in the reaction play a decisive role in the conversion of CMA and selectivity of CMO and other products [2,3] .…”

Section: Introductionmentioning

confidence: 99%

In‐Situ Incorporation of Pt Nanoparticles on Layered Double Hydroxides for Selective Conversion of Cinnamaldehyde to Cinnamyl Alcohol

et al. 2021

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Designing efficient and low‐cost catalysts for generation of cinnamyl alcohol (CMO) from cinnamaldehyde (CMA) hydrogenation is of practical value. Herein, layered double hydroxide supported Pt nanoparticles (Pt‐s/LDH) were prepared by in‐situ reduction of PtCl62− in PtCl62−‐LDH with ethylene glycol, and the PtCl62− was intercalated in LDH by ion‐exchange method. The characterization results verify that small Pt nanoparticles are uniformly distributed on LDH with average diameter of 1.9 nm and narrow size distribution. The prepared Pt‐s/LDH catalyst exhibits excellent catalytic performance for selective hydrogenation of CMA under relatively mild reaction conditions (80 °C, 2 MPa H2) with high turnover frequency (TOF) (0.574 s−1) and CMA conversion (92.6 %). Furthermore, the CMA conversion rate and CMO selectivity remain almost unchanged after the fourth run compared with the results of the first run. This study provides an effective route for synthesis of efficient and stable LDH‐supported metal catalysts.

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Hydrogenation of cinnamaldehyde to cinnamyl alcohol with metal phosphides: Catalytic consequences of product and pyridine doping

Cited by 40 publications

References 46 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

Vapour phase hydrogenation of cinnamaldehyde using cobalt supported inside and outside hollow carbon spheres

In‐Situ Incorporation of Pt Nanoparticles on Layered Double Hydroxides for Selective Conversion of Cinnamaldehyde to Cinnamyl Alcohol

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