Homogeneous Reforming of Aqueous Ethylene Glycol to Glycolic Acid and Pure Hydrogen Catalyzed by Pincer-Ruthenium Complexes Capable of Metal–Ligand Cooperation

You Quan Zou; Niklas von Wolff; Michael Rauch; Moran Feller; Quan Quan Zhou; Aviel Anaby; Yael Diskin-Posner; Linda J.W. Shimon; Liat Avram; Yehoshoa Ben-David; David Milstein

doi:10.1002/chem.202005450

Homogeneous Reforming of Aqueous Ethylene Glycol to Glycolic Acid and Pure Hydrogen Catalyzed by Pincer-Ruthenium Complexes Capable of Metal–Ligand Cooperation

You Quan Zou, Niklas von Wolff, Michael Rauch, Moran Feller, Quan Quan Zhou, Aviel Anaby, Yael Diskin-Posner, Linda J.W. Shimon, Liat Avram, Yehoshoa Ben-David, David Milstein^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

31 Citations (Scopus)

Abstract

Glycolic acid is a useful and important α-hydroxy acid that has broad applications. Herein, the homogeneous ruthenium catalyzed reforming of aqueous ethylene glycol to generate glycolic acid as well as pure hydrogen gas, without concomitant CO₂ emission, is reported. This approach provides a clean and sustainable direction to glycolic acid and hydrogen, based on inexpensive, readily available, and renewable ethylene glycol using 0.5 mol % of catalyst. In-depth mechanistic experimental and computational studies highlight key aspects of the PNNH-ligand framework involved in this transformation.

Original language	English
Pages (from-to)	4715-4722
Number of pages	8
Journal	Chemistry - A European Journal
Volume	27
Issue number	14
Early online date	11 Feb 2021
DOIs	https://doi.org/10.1002/chem.202005450
Publication status	Published - 8 Mar 2021

Funding

D.M. holds the Israel Matz Professorial Chair of Organic Chemistry. Y.‐Q.Z. acknowledges the Sustainability and Energy Research Initiative (SAERI) of Weizmann Institute of Science for a research fellowship. N.v.W. is supported by the Foreign Postdoctoral Fellowship Program of the Israel Academy of Sciences and Humanities. M.R. acknowledges the Zuckerman STEM Leadership Program for a research fellowship. N.v.W and M.R. thank Dr. Mark Iron (department of chemical research support) for fruitful discussions regarding the DFT calculations. Computations were performed using HPC resources from GENCI‐CINES (Grant 2019AP010811227).

All Science Journal Classification (ASJC) codes

Catalysis
Organic Chemistry

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Zou, Y. Q., von Wolff, N., Rauch, M., Feller, M., Zhou, Q. Q., Anaby, A., Diskin-Posner, Y., Shimon, L. J. W., Avram, L., Ben-David, Y., & Milstein, D. (2021). Homogeneous Reforming of Aqueous Ethylene Glycol to Glycolic Acid and Pure Hydrogen Catalyzed by Pincer-Ruthenium Complexes Capable of Metal–Ligand Cooperation. Chemistry - A European Journal, 27(14), 4715-4722. https://doi.org/10.1002/chem.202005450

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abstract = "Glycolic acid is a useful and important α-hydroxy acid that has broad applications. Herein, the homogeneous ruthenium catalyzed reforming of aqueous ethylene glycol to generate glycolic acid as well as pure hydrogen gas, without concomitant CO2 emission, is reported. This approach provides a clean and sustainable direction to glycolic acid and hydrogen, based on inexpensive, readily available, and renewable ethylene glycol using 0.5 mol % of catalyst. In-depth mechanistic experimental and computational studies highlight key aspects of the PNNH-ligand framework involved in this transformation.",

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Zou, YQ, von Wolff, N, Rauch, M, Feller, M, Zhou, QQ, Anaby, A, Diskin-Posner, Y , Shimon, LJW , Avram, L, Ben-David, Y & Milstein, D 2021, 'Homogeneous Reforming of Aqueous Ethylene Glycol to Glycolic Acid and Pure Hydrogen Catalyzed by Pincer-Ruthenium Complexes Capable of Metal–Ligand Cooperation', Chemistry - A European Journal, vol. 27, no. 14, pp. 4715-4722. https://doi.org/10.1002/chem.202005450

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AU - Rauch, Michael

AU - Feller, Moran

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AU - Diskin-Posner, Yael

AU - Shimon, Linda J.W.

AU - Avram, Liat

AU - Ben-David, Yehoshoa

AU - Milstein, David

PY - 2021/3/8

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AB - Glycolic acid is a useful and important α-hydroxy acid that has broad applications. Herein, the homogeneous ruthenium catalyzed reforming of aqueous ethylene glycol to generate glycolic acid as well as pure hydrogen gas, without concomitant CO2 emission, is reported. This approach provides a clean and sustainable direction to glycolic acid and hydrogen, based on inexpensive, readily available, and renewable ethylene glycol using 0.5 mol % of catalyst. In-depth mechanistic experimental and computational studies highlight key aspects of the PNNH-ligand framework involved in this transformation.

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Homogeneous Reforming of Aqueous Ethylene Glycol to Glycolic Acid and Pure Hydrogen Catalyzed by Pincer-Ruthenium Complexes Capable of Metal–Ligand Cooperation

Abstract

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