Inhibition of a gold-based catalyst in benzyl alcohol oxidation: Understanding and remediation

Emmanuel Skupien; Rob J. Berger; Vera P. Santos; Jorge Gascon; Michiel Makkee; Michiel T. Kreutzer; Patricia J. Kooyman; Jacob A. Moulijn; Freek Kapteijn

doi:10.3390/catal4020089

Inhibition of a gold-based catalyst in benzyl alcohol oxidation: Understanding and remediation

Emmanuel Skupien^*, Rob J. Berger, Vera P. Santos, Jorge Gascon, Michiel Makkee, Michiel T. Kreutzer, Patricia J. Kooyman, Jacob A. Moulijn, Freek Kapteijn

^*Corresponding author for this work

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

46 Scopus citations

Abstract

Benzyl alcohol oxidation was carried out in toluene as solvent, in the presence of the potentially inhibiting oxidation products benzaldehyde and benzoic acid. Benzoic acid, or a product of benzoic acid, is identified to be the inhibiting species. The presence of a basic potassium salt (K₂CO₃ or KF) suppresses this inhibition, but promotes the formation of benzyl benzoate from the alcohol and aldehyde. When a small amount of water is added together with the potassium salt, an even greater beneficial effect is observed, due to a synergistic effect with the base. A kinetic model, based on the three main reactions and four major reaction components, is presented to describe the concentration-time profiles and inhibition. The inhibition, as well as the effect of the base, was captured in the kinetic model, by combining strong benzoic acid adsorption and competitive adsorption with benzyl alcohol. The effect of the potassium salt is accounted for in terms of neutralization of benzoic acid.

Original language	English (US)
Pages (from-to)	89-115
Number of pages	27
Journal	Catalysts
Volume	4
Issue number	2
DOIs	https://doi.org/10.3390/catal4020089
State	Published - Apr 15 2014
Externally published	Yes

Keywords

Benzyl alcohol
Catalysis
Deactivation
Gold
Inhibition
Kinetics
Mechanism
Modeling
Oxidation

ASJC Scopus subject areas

Catalysis
General Environmental Science
Physical and Theoretical Chemistry

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10.3390/catal4020089

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title = "Inhibition of a gold-based catalyst in benzyl alcohol oxidation: Understanding and remediation",

abstract = "Benzyl alcohol oxidation was carried out in toluene as solvent, in the presence of the potentially inhibiting oxidation products benzaldehyde and benzoic acid. Benzoic acid, or a product of benzoic acid, is identified to be the inhibiting species. The presence of a basic potassium salt (K2CO3 or KF) suppresses this inhibition, but promotes the formation of benzyl benzoate from the alcohol and aldehyde. When a small amount of water is added together with the potassium salt, an even greater beneficial effect is observed, due to a synergistic effect with the base. A kinetic model, based on the three main reactions and four major reaction components, is presented to describe the concentration-time profiles and inhibition. The inhibition, as well as the effect of the base, was captured in the kinetic model, by combining strong benzoic acid adsorption and competitive adsorption with benzyl alcohol. The effect of the potassium salt is accounted for in terms of neutralization of benzoic acid.",

keywords = "Benzyl alcohol, Catalysis, Deactivation, Gold, Inhibition, Kinetics, Mechanism, Modeling, Oxidation",

author = "Emmanuel Skupien and Berger, {Rob J.} and Santos, {Vera P.} and Jorge Gascon and Michiel Makkee and Kreutzer, {Michiel T.} and Kooyman, {Patricia J.} and Moulijn, {Jacob A.} and Freek Kapteijn",

year = "2014",

month = apr,

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doi = "10.3390/catal4020089",

language = "English (US)",

volume = "4",

pages = "89--115",

journal = "Catalysts",

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T2 - Understanding and remediation

AU - Skupien, Emmanuel

AU - Berger, Rob J.

AU - Santos, Vera P.

AU - Gascon, Jorge

AU - Makkee, Michiel

AU - Kreutzer, Michiel T.

AU - Kooyman, Patricia J.

AU - Moulijn, Jacob A.

AU - Kapteijn, Freek

PY - 2014/4/15

Y1 - 2014/4/15

N2 - Benzyl alcohol oxidation was carried out in toluene as solvent, in the presence of the potentially inhibiting oxidation products benzaldehyde and benzoic acid. Benzoic acid, or a product of benzoic acid, is identified to be the inhibiting species. The presence of a basic potassium salt (K2CO3 or KF) suppresses this inhibition, but promotes the formation of benzyl benzoate from the alcohol and aldehyde. When a small amount of water is added together with the potassium salt, an even greater beneficial effect is observed, due to a synergistic effect with the base. A kinetic model, based on the three main reactions and four major reaction components, is presented to describe the concentration-time profiles and inhibition. The inhibition, as well as the effect of the base, was captured in the kinetic model, by combining strong benzoic acid adsorption and competitive adsorption with benzyl alcohol. The effect of the potassium salt is accounted for in terms of neutralization of benzoic acid.

AB - Benzyl alcohol oxidation was carried out in toluene as solvent, in the presence of the potentially inhibiting oxidation products benzaldehyde and benzoic acid. Benzoic acid, or a product of benzoic acid, is identified to be the inhibiting species. The presence of a basic potassium salt (K2CO3 or KF) suppresses this inhibition, but promotes the formation of benzyl benzoate from the alcohol and aldehyde. When a small amount of water is added together with the potassium salt, an even greater beneficial effect is observed, due to a synergistic effect with the base. A kinetic model, based on the three main reactions and four major reaction components, is presented to describe the concentration-time profiles and inhibition. The inhibition, as well as the effect of the base, was captured in the kinetic model, by combining strong benzoic acid adsorption and competitive adsorption with benzyl alcohol. The effect of the potassium salt is accounted for in terms of neutralization of benzoic acid.

KW - Benzyl alcohol

KW - Catalysis

KW - Deactivation

KW - Gold

KW - Inhibition

KW - Kinetics

KW - Mechanism

KW - Modeling

KW - Oxidation

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U2 - 10.3390/catal4020089

DO - 10.3390/catal4020089

M3 - Article

AN - SCOPUS:84906859122

SN - 2073-4344

VL - 4

SP - 89

EP - 115

JO - Catalysts

JF - Catalysts

IS - 2

ER -

Inhibition of a gold-based catalyst in benzyl alcohol oxidation: Understanding and remediation

Abstract

Keywords

ASJC Scopus subject areas

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