Pd/C-catalyzed reactions of HMF: Decarbonylation, hydrogenation, and hydrogenolysis

Joyee Mitra; Xiaoyuan Zhou; Thomas Rauchfuss

doi:10.1039/c4gc01520g

Pd/C-catalyzed reactions of HMF: Decarbonylation, hydrogenation, and hydrogenolysis

Joyee Mitra, Xiaoyuan Zhou, Thomas Rauchfuss

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

Abstract

The diverse reactivity of 5-hydroxymethylfural (HMF) in Pd/C-catalyzed reactions is described with emphasis on the role of additives that affect selectivity. Three broad reactions are examined: decarbonylation, hydrogenation, and hydrogenolysis. Especially striking are the multiple roles of formic acid in hydrogenolysis/ hydrogenation and in suppressing decarbonylation, as illustrated by the conversion of HMF to DMF. Hydrogenation of the furan ring is suppressed by CO₂ and carboxylic acids. These results emphasize the utility of Pd/C as a convenient catalyst for upgradation of cellulosic biomass.

Original language	English (US)
Pages (from-to)	307-313
Number of pages	7
Journal	Green Chemistry
Volume	17
Issue number	1
DOIs	https://doi.org/10.1039/c4gc01520g
State	Published - Jan 1 2015

ASJC Scopus subject areas

Environmental Chemistry
Pollution

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10.1039/c4gc01520g

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abstract = "The diverse reactivity of 5-hydroxymethylfural (HMF) in Pd/C-catalyzed reactions is described with emphasis on the role of additives that affect selectivity. Three broad reactions are examined: decarbonylation, hydrogenation, and hydrogenolysis. Especially striking are the multiple roles of formic acid in hydrogenolysis/ hydrogenation and in suppressing decarbonylation, as illustrated by the conversion of HMF to DMF. Hydrogenation of the furan ring is suppressed by CO2 and carboxylic acids. These results emphasize the utility of Pd/C as a convenient catalyst for upgradation of cellulosic biomass.",

author = "Joyee Mitra and Xiaoyuan Zhou and Thomas Rauchfuss",

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AU - Mitra, Joyee

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AU - Rauchfuss, Thomas

N1 - Funding Information: This research was conducted under contract DEFG02-90ER14146 with the U.S. Department of Energy by its Division of Chemical Sciences, Office of Basic Energy Sciences. Support for JM and XY was provided in part by the Energy Biosciences Institute, funded by British Petroleum. Publisher Copyright: © 2015 The Royal Society of Chemistry. Copyright: Copyright 2020 Elsevier B.V., All rights reserved.

PY - 2015/1/1

Y1 - 2015/1/1

N2 - The diverse reactivity of 5-hydroxymethylfural (HMF) in Pd/C-catalyzed reactions is described with emphasis on the role of additives that affect selectivity. Three broad reactions are examined: decarbonylation, hydrogenation, and hydrogenolysis. Especially striking are the multiple roles of formic acid in hydrogenolysis/ hydrogenation and in suppressing decarbonylation, as illustrated by the conversion of HMF to DMF. Hydrogenation of the furan ring is suppressed by CO2 and carboxylic acids. These results emphasize the utility of Pd/C as a convenient catalyst for upgradation of cellulosic biomass.

AB - The diverse reactivity of 5-hydroxymethylfural (HMF) in Pd/C-catalyzed reactions is described with emphasis on the role of additives that affect selectivity. Three broad reactions are examined: decarbonylation, hydrogenation, and hydrogenolysis. Especially striking are the multiple roles of formic acid in hydrogenolysis/ hydrogenation and in suppressing decarbonylation, as illustrated by the conversion of HMF to DMF. Hydrogenation of the furan ring is suppressed by CO2 and carboxylic acids. These results emphasize the utility of Pd/C as a convenient catalyst for upgradation of cellulosic biomass.

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Pd/C-catalyzed reactions of HMF: Decarbonylation, hydrogenation, and hydrogenolysis

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