Aqueous-phase hydrodeoxygenation of bio-derived phenols to cycloalkanes

Chen Zhao; Jiayue He; Angeliki A. Lemonidou; Xuebing Li; Johannes A. Lercher

doi:10.1016/j.jcat.2011.02.001

Aqueous-phase hydrodeoxygenation of bio-derived phenols to cycloalkanes

Chen Zhao, Jiayue He, Angeliki A. Lemonidou, Xuebing Li, Johannes A. Lercher

Chair of Chemical Technology II

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

477 Scopus citations

Abstract

The kinetics of the catalytic hydrodeoxygenation of phenol and substituted phenols has systematically been investigated on the dual-functional catalyst system Pd/C and H₃PO₄ in order to better understand the elementary steps of the overall reaction. The reaction proceeds via stepwise hydrogenation of the aromatic ring, transformation of the cyclic enol to the corresponding ketone, hydrogenation of the cycloalkanone to the cycloalkanol and its subsequent dehydration as well as the hydrogenation of the formed cycloalkene. The presence of dual catalytic functions is indispensible for the overall hydrodeoxygenation. The dehydration reaction is significantly slower than the hydrogenation reaction and the keto/enol transformation, requiring a significantly larger concentration of Brønsted acid sites compared to the available metal sites for hydrogenation.

Original language	English
Pages (from-to)	8-16
Number of pages	9
Journal	Journal of Catalysis
Volume	280
Issue number	1
DOIs	https://doi.org/10.1016/j.jcat.2011.02.001
State	Published - 16 May 2011

Keywords

Aqueous-phase catalysis
Bio-oil
Dual-functional catalysis
Hydrodeoxygenation
Palladium
Phenol derivatives

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10.1016/j.jcat.2011.02.001

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title = "Aqueous-phase hydrodeoxygenation of bio-derived phenols to cycloalkanes",

abstract = "The kinetics of the catalytic hydrodeoxygenation of phenol and substituted phenols has systematically been investigated on the dual-functional catalyst system Pd/C and H3PO4 in order to better understand the elementary steps of the overall reaction. The reaction proceeds via stepwise hydrogenation of the aromatic ring, transformation of the cyclic enol to the corresponding ketone, hydrogenation of the cycloalkanone to the cycloalkanol and its subsequent dehydration as well as the hydrogenation of the formed cycloalkene. The presence of dual catalytic functions is indispensible for the overall hydrodeoxygenation. The dehydration reaction is significantly slower than the hydrogenation reaction and the keto/enol transformation, requiring a significantly larger concentration of Br{\o}nsted acid sites compared to the available metal sites for hydrogenation.",

keywords = "Aqueous-phase catalysis, Bio-oil, Dual-functional catalysis, Hydrodeoxygenation, Palladium, Phenol derivatives",

author = "Chen Zhao and Jiayue He and Lemonidou, {Angeliki A.} and Xuebing Li and Lercher, {Johannes A.}",

note = "Funding Information: This work was supported by the Technische Universit{\"a}t M{\"u}nchen in the framework of the European Graduate School for Sustainable Energy. Valuable discussions in the framework of the network of excellence IDECAT are also gratefully acknowledged. ",

year = "2011",

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doi = "10.1016/j.jcat.2011.02.001",

language = "English",

volume = "280",

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journal = "Journal of Catalysis",

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T1 - Aqueous-phase hydrodeoxygenation of bio-derived phenols to cycloalkanes

AU - Zhao, Chen

AU - He, Jiayue

AU - Lemonidou, Angeliki A.

AU - Li, Xuebing

AU - Lercher, Johannes A.

N1 - Funding Information: This work was supported by the Technische Universität München in the framework of the European Graduate School for Sustainable Energy. Valuable discussions in the framework of the network of excellence IDECAT are also gratefully acknowledged.

PY - 2011/5/16

Y1 - 2011/5/16

N2 - The kinetics of the catalytic hydrodeoxygenation of phenol and substituted phenols has systematically been investigated on the dual-functional catalyst system Pd/C and H3PO4 in order to better understand the elementary steps of the overall reaction. The reaction proceeds via stepwise hydrogenation of the aromatic ring, transformation of the cyclic enol to the corresponding ketone, hydrogenation of the cycloalkanone to the cycloalkanol and its subsequent dehydration as well as the hydrogenation of the formed cycloalkene. The presence of dual catalytic functions is indispensible for the overall hydrodeoxygenation. The dehydration reaction is significantly slower than the hydrogenation reaction and the keto/enol transformation, requiring a significantly larger concentration of Brønsted acid sites compared to the available metal sites for hydrogenation.

AB - The kinetics of the catalytic hydrodeoxygenation of phenol and substituted phenols has systematically been investigated on the dual-functional catalyst system Pd/C and H3PO4 in order to better understand the elementary steps of the overall reaction. The reaction proceeds via stepwise hydrogenation of the aromatic ring, transformation of the cyclic enol to the corresponding ketone, hydrogenation of the cycloalkanone to the cycloalkanol and its subsequent dehydration as well as the hydrogenation of the formed cycloalkene. The presence of dual catalytic functions is indispensible for the overall hydrodeoxygenation. The dehydration reaction is significantly slower than the hydrogenation reaction and the keto/enol transformation, requiring a significantly larger concentration of Brønsted acid sites compared to the available metal sites for hydrogenation.

KW - Aqueous-phase catalysis

KW - Bio-oil

KW - Dual-functional catalysis

KW - Hydrodeoxygenation

KW - Palladium

KW - Phenol derivatives

UR - http://www.scopus.com/inward/record.url?scp=79955439344&partnerID=8YFLogxK

U2 - 10.1016/j.jcat.2011.02.001

DO - 10.1016/j.jcat.2011.02.001

M3 - Article

AN - SCOPUS:79955439344

SN - 0021-9517

VL - 280

SP - 8

EP - 16

JO - Journal of Catalysis

JF - Journal of Catalysis

IS - 1

ER -

Aqueous-phase hydrodeoxygenation of bio-derived phenols to cycloalkanes

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Keywords

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