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Title: A Combined Experimental and Theoretical Study on the Activity and Selectivity of the Electrocatalytic Hydrogenation of Aldehydes

Abstract

A detailed mechanistic study of the electrochemical hydrogenation of aldehydes is presented toward the goal of identifying how organic molecules in solution behave at the interface with charged surfaces and what is the best manner to convert them. Specifically, this study focuses on designing an electrocatalytic route for ambient temperature post-pyrolysis treatment of bio-oil. Aldehyde reductions are needed to convert biomass into fuels or chemicals. A combined experimental and computational approach is taken toward catalyst design to provide testable hypotheses regarding catalyst composition, activity, and selectivity. Electrochemical hydrogenation mechanisms for benzaldehyde and pentanal reduction are found to proceed by a coupled proton-electron transfer process. Initial results show that Au, Ag, Cu, and C catalysts exhibit the highest conversion to alcohol products. These catalysts are suitable because they show high cathodic onset potentials for H2 formation and low cathodic onset potentials for organic reduction. Conversion of aromatic aldehydes is found to be appreciably higher than aliphatic ones. Classical molecular dynamics simulations of solvent and substrate mixtures in an electrolytic cell were performed to assess how species concentrations vary at the solid/liquid interface and in the bulk as a function of applied voltage. Results show that an increase in voltage in themore » electrolytic cell decreases organic and increases water mole fractions at the solid/liquid interface. In this current study, charged cathodic surfaces result in carbonyl orientations at the surface that do not favor electron transfer. Repulsion of organic substrates to the bulk must be compensated by strong adhesion to the electrode surface. In conclusion, implications on catalyst choice and process design are discussed.« less

Authors:
 [1];  [2];  [1];  [1];  [1];  [1];  [1];  [1];  [1];  [2]
  1. Pacific Northwest National Lab. (PNNL), Richland, WA (United States). Inst. for Integrated Catalysis
  2. Pacific Northwest National Lab. (PNNL), Richland, WA (United States). Energy and Environment Directorate,
Publication Date:
Research Org.:
Pacific Northwest National Lab. (PNNL), Richland, WA (United States)
Sponsoring Org.:
USDOE
OSTI Identifier:
1460961
Report Number(s):
PNNL-SA-132938
Journal ID: ISSN 2155-5435
Grant/Contract Number:  
AC05-76RL01830
Resource Type:
Accepted Manuscript
Journal Name:
ACS Catalysis
Additional Journal Information:
Journal Volume: 8; Journal Issue: 8; Journal ID: ISSN 2155-5435
Publisher:
American Chemical Society (ACS)
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; Pyrolysis Oil upgrading; Atomistic Simulations; Electrocatalysis; Aldehydes; Electrochemical reduction; benzaldehyde; pentanal

Citation Formats

Cantu, David C., Padmaperuma, Asanga B., Nguyen, Manh-Thuong, Akhade, Sneha A., Yoon, Yeohoon, Wang, Yang-Gang, Lee, Mal-Soon, Glezakou, Vassiliki-Alexandra, Rousseau, Roger, and Lilga, Michael A. A Combined Experimental and Theoretical Study on the Activity and Selectivity of the Electrocatalytic Hydrogenation of Aldehydes. United States: N. p., 2018. Web. doi:10.1021/ACSCATAL.8B00858.
Cantu, David C., Padmaperuma, Asanga B., Nguyen, Manh-Thuong, Akhade, Sneha A., Yoon, Yeohoon, Wang, Yang-Gang, Lee, Mal-Soon, Glezakou, Vassiliki-Alexandra, Rousseau, Roger, & Lilga, Michael A. A Combined Experimental and Theoretical Study on the Activity and Selectivity of the Electrocatalytic Hydrogenation of Aldehydes. United States. https://doi.org/10.1021/ACSCATAL.8B00858
Cantu, David C., Padmaperuma, Asanga B., Nguyen, Manh-Thuong, Akhade, Sneha A., Yoon, Yeohoon, Wang, Yang-Gang, Lee, Mal-Soon, Glezakou, Vassiliki-Alexandra, Rousseau, Roger, and Lilga, Michael A. Fri . "A Combined Experimental and Theoretical Study on the Activity and Selectivity of the Electrocatalytic Hydrogenation of Aldehydes". United States. https://doi.org/10.1021/ACSCATAL.8B00858. https://www.osti.gov/servlets/purl/1460961.
@article{osti_1460961,
title = {A Combined Experimental and Theoretical Study on the Activity and Selectivity of the Electrocatalytic Hydrogenation of Aldehydes},
author = {Cantu, David C. and Padmaperuma, Asanga B. and Nguyen, Manh-Thuong and Akhade, Sneha A. and Yoon, Yeohoon and Wang, Yang-Gang and Lee, Mal-Soon and Glezakou, Vassiliki-Alexandra and Rousseau, Roger and Lilga, Michael A.},
abstractNote = {A detailed mechanistic study of the electrochemical hydrogenation of aldehydes is presented toward the goal of identifying how organic molecules in solution behave at the interface with charged surfaces and what is the best manner to convert them. Specifically, this study focuses on designing an electrocatalytic route for ambient temperature post-pyrolysis treatment of bio-oil. Aldehyde reductions are needed to convert biomass into fuels or chemicals. A combined experimental and computational approach is taken toward catalyst design to provide testable hypotheses regarding catalyst composition, activity, and selectivity. Electrochemical hydrogenation mechanisms for benzaldehyde and pentanal reduction are found to proceed by a coupled proton-electron transfer process. Initial results show that Au, Ag, Cu, and C catalysts exhibit the highest conversion to alcohol products. These catalysts are suitable because they show high cathodic onset potentials for H2 formation and low cathodic onset potentials for organic reduction. Conversion of aromatic aldehydes is found to be appreciably higher than aliphatic ones. Classical molecular dynamics simulations of solvent and substrate mixtures in an electrolytic cell were performed to assess how species concentrations vary at the solid/liquid interface and in the bulk as a function of applied voltage. Results show that an increase in voltage in the electrolytic cell decreases organic and increases water mole fractions at the solid/liquid interface. In this current study, charged cathodic surfaces result in carbonyl orientations at the surface that do not favor electron transfer. Repulsion of organic substrates to the bulk must be compensated by strong adhesion to the electrode surface. In conclusion, implications on catalyst choice and process design are discussed.},
doi = {10.1021/ACSCATAL.8B00858},
journal = {ACS Catalysis},
number = 8,
volume = 8,
place = {United States},
year = {2018},
month = {6}
}

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