Catalytic Hydrogenation of Benzaldehyde for Selective Synthesis of Benzyl Alcohol: A Review

Bhanushali, Jayesh T.; Kainthla, Itika; Keri, Rangappa S.; Nagaraja, Bhari Mallanna

doi:10.1002/slct.201600712

Cited by 38 publications

(17 citation statements)

References 168 publications

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“…For all experiments, the middle and outer electrochemical compartments were filled with 35 and 45 mL of 1 M H 2 SO 4 , respectively. Benzaldehyde (0H) was selected as a model compound here because its analogues are used in the production of aromatic alcohol and upgrading processes of bioderived oil. − The hydrogenation compartment was filled with 0.1 M 0H in 30 mL of ethanol and stirred at a constant rate of 600 rpm. A galvanostatic current (200 mA) applied between the Pt and Pd electrodes was used to drive water oxidation at the Pt anode and simultaneous proton reduction at the Pd cathode.…”

Section: Resultsmentioning

confidence: 99%

Electrolysis Can Be Used to Resolve Hydrogenation Pathways at Palladium Surfaces in a Membrane Reactor

Huang

Cao

Delima

et al. 2021

JACS Au

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For common hydrogenation chemistries that occur at high temperatures (where H 2 is adsorbed and activated at the same surface which the substrate must also adsorb for reaction), there is often little consensus on how the reactions (e.g., hydro(deoxy)genation) actually occur. We demonstrate here that an electrocatalytic palladium membrane reactor (ePMR) can be used to study hydrogenation reaction mechanisms at ambient temperatures, where the catalyst does not necessarily undergo structural reorganization. The ePMR uses electrolysis and a hydrogen-selective palladium membrane to deliver reactive hydrogen to a catalyst surface in an adjacent compartment for reaction with an organic substrate. This process forms the requisite metal-hydride surface for hydrogenation chemistry, but at ambient temperature and pressure, and without a H 2 source. We demonstrate the utility of this analytical tool by studying the hydrogenation of benzaldehyde at palladium nanocubes with dimensions of 13–24 nm. This experimental design enabled us to resolve that the alcohol product forms at the facial sites, whereas the hydrodeoxygenation step occurs at edge sites. These observations enabled us to develop the first site-specific definition of how a carbonyl species undergoes hydro(deoxy)genation.

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Section: Resultsmentioning

confidence: 99%

Electrolysis Can Be Used to Resolve Hydrogenation Pathways at Palladium Surfaces in a Membrane Reactor

Huang

Cao

Delima

et al. 2021

JACS Au

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“…Benzyl alcohol (BnOH) is an important intermediate in the production of paints, varnishes [1], and vitamins [2]. It is also widely used in the chemical industry as a precursor for the synthesis of various esters and fragrances [3].…”

Section: Introductionmentioning

confidence: 99%

Liquid-Phase Hydrogenation of Benzaldehyde on Low-Percentage Pt-Containing Catalysts under Mild Conditions

Виканова

Редина

Капустин

2022

Russ. J. Phys. Chem.

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The reaction of the liquid-phase hydrogenation of benzaldehyde is studied in two modes: at room temperature and atmospheric pressure, and at a temperature of 70°С and a pressure of 0.5 MPa on Pt/CeO2–ZrО2 catalysts with metal contents of 1 to 0.025 wt %. A 96% conversion of benzaldehyde is obtained on 1% Pt/CeO2–ZrО2 catalysts at room temperature, while a 97% conversion is obtained on 0.1% Pt/CeO2–ZrО2 catalysts at elevated temperatures. The selectivity of the formation of benzyl alcohol is in all cases 100%.

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“…ECH in aqueous media have been reported mostly for unsaturated organic molecules, including the hydrogenation of aromatic compounds, − edible oils, − quinonemethides, , and other olefins. − The electroreduction of other oxygenated functional groups (i.e., ethers, ketones, and alcohols) has been studied extensibly, ,− while the ECH of nitrile groups has received less attention despite its important implications in chemical manufacturing. The conversion of adiponitrile (ADN) to hexamethylenediamine (HMDA) − is an example of a carbon–nitrogen bond hydrogenation that can be done electrochemically using Raney Nickel or palladium electrodes.…”

Section: Introductionmentioning

confidence: 99%

Controlling Selectivity in the Electrocatalytic Hydrogenation of Adiponitrile through Electrolyte Design

Blanco

Dookhith

Modestino

2020

ACS Sustainable Chem. Eng.

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Organic hydrogenations are key steps in the production of numerous valuable chemicals. Their requirement for high temperature, pressure, and compressed hydrogen has motivated the interest to develop safer electrocatalytic hydrogenation (ECH) routes in benign aqueous electrolytes. However, faradaic efficiencies in organic ECH tend to be greatly limited by competition with the hydrogen evolution reaction and low reactant solubility, which hinders the implementation of these more sustainable hydrogenation routes. Using the hydrogenation of adiponitrile to hexamethylenediamine (HMDA), a monomer used in the production of nylon-6,6, as a case study, we investigate the effect of reactant concentration, temperature, pH, and organic cosolvents on the ECH of nitrile groups with Raney nickel electrodes. Higher reactant concentrations, alkaline electrolytes, and mild temperature (40 °C) are key conditions that enhance the hydrogenation of organic substrates against hydrogen evolution. A maximum faradaic efficiency of 92% toward HMDA was obtained in aqueous electrolytes at −60 mA cm–2. The addition of an organic cosolvent is subsequently studied to evaluate the effect of enhanced reactant solubility, achieving a 95% faradaic efficiency at the same current density with 30% methanol by volume in water. The insights gained from this study are relevant for the design of energy efficient organic ECH and can help accelerate the implementation of sustainable chemical manufacturing.

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Catalytic Hydrogenation of Benzaldehyde for Selective Synthesis of Benzyl Alcohol: A Review

Cited by 38 publications

References 168 publications

Electrolysis Can Be Used to Resolve Hydrogenation Pathways at Palladium Surfaces in a Membrane Reactor

Electrolysis Can Be Used to Resolve Hydrogenation Pathways at Palladium Surfaces in a Membrane Reactor

Liquid-Phase Hydrogenation of Benzaldehyde on Low-Percentage Pt-Containing Catalysts under Mild Conditions

Controlling Selectivity in the Electrocatalytic Hydrogenation of Adiponitrile through Electrolyte Design

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