Catalytic Cleavage of Ether Bond in a Lignin Model Compound over Carbon-Supported Noble Metal Catalysts in Supercritical Ethanol

Decomposition of lignin-related model compound (benzyl phenyl ether, BPE) to phenol and toluene was performed over carbon-supported noble metal (Ru, Pd, and Pt) catalysts in supercritical ethanol without supply of hydrogen. Phenol and toluene as target products were produced by the hydrogenolysis of...

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Main Authors: Seungdo Yang, Soyeon Jeong, Chunghyeon Ban, Hyungjoo Kim, Do Heui Kim
Format: Article
Language:English
Published: MDPI AG 2019-02-01
Series:Catalysts
Subjects:
Online Access:https://www.mdpi.com/2073-4344/9/2/158
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spelling doaj-ddf7235bc6cf40fba7bc6bb2a76b62652020-11-25T01:01:02ZengMDPI AGCatalysts2073-43442019-02-019215810.3390/catal9020158catal9020158Catalytic Cleavage of Ether Bond in a Lignin Model Compound over Carbon-Supported Noble Metal Catalysts in Supercritical EthanolSeungdo Yang0Soyeon Jeong1Chunghyeon Ban2Hyungjoo Kim3Do Heui Kim4Laboratory for Energy and Environmental Catalysis at School of Chem. & Bio. Eng., Seoul National University, 1, Gwanak-ro, Gwanak-gu, Seoul 08826, KoreaLaboratory for Energy and Environmental Catalysis at School of Chem. & Bio. Eng., Seoul National University, 1, Gwanak-ro, Gwanak-gu, Seoul 08826, KoreaLaboratory for Energy and Environmental Catalysis at School of Chem. & Bio. Eng., Seoul National University, 1, Gwanak-ro, Gwanak-gu, Seoul 08826, KoreaLaboratory for Energy and Environmental Catalysis at School of Chem. & Bio. Eng., Seoul National University, 1, Gwanak-ro, Gwanak-gu, Seoul 08826, KoreaLaboratory for Energy and Environmental Catalysis at School of Chem. & Bio. Eng., Seoul National University, 1, Gwanak-ro, Gwanak-gu, Seoul 08826, KoreaDecomposition of lignin-related model compound (benzyl phenyl ether, BPE) to phenol and toluene was performed over carbon-supported noble metal (Ru, Pd, and Pt) catalysts in supercritical ethanol without supply of hydrogen. Phenol and toluene as target products were produced by the hydrogenolysis of BPE. The conversion of BPE was higher than 95% over all carbon-supported noble metal catalysts at 270 °C for 4 h. The 5 wt% Pd/C demonstrated the highest yield (ca. 59.3%) of the target products and enhanced conversion rates and reactivity more significantly than other catalysts. In the case of Ru/C, BPE was significantly transformed to other unidentified byproducts, more so than other catalysts. The Pt/C catalyst produced the highest number of byproducts such as alkylated phenols and gas-phase products, indicating that the catalyst promotes secondary reactions during the decomposition of BPE. In addition, a model reaction using phenol as a reactant was conducted to check the secondary reactions of phenol such as alkylation or hydrogenation in supercritical ethanol. The product distribution when phenol was used as a reactant was mostly consistent with BPE as a reactant. Based on the results, plausible reaction pathways were proposed.https://www.mdpi.com/2073-4344/9/2/158benzyl phenyl ethersolvolysissupercritical ethanolcarbon-supported noble metal catalysts
collection DOAJ
language English
format Article
sources DOAJ
author Seungdo Yang
Soyeon Jeong
Chunghyeon Ban
Hyungjoo Kim
Do Heui Kim
spellingShingle Seungdo Yang
Soyeon Jeong
Chunghyeon Ban
Hyungjoo Kim
Do Heui Kim
Catalytic Cleavage of Ether Bond in a Lignin Model Compound over Carbon-Supported Noble Metal Catalysts in Supercritical Ethanol
Catalysts
benzyl phenyl ether
solvolysis
supercritical ethanol
carbon-supported noble metal catalysts
author_facet Seungdo Yang
Soyeon Jeong
Chunghyeon Ban
Hyungjoo Kim
Do Heui Kim
author_sort Seungdo Yang
title Catalytic Cleavage of Ether Bond in a Lignin Model Compound over Carbon-Supported Noble Metal Catalysts in Supercritical Ethanol
title_short Catalytic Cleavage of Ether Bond in a Lignin Model Compound over Carbon-Supported Noble Metal Catalysts in Supercritical Ethanol
title_full Catalytic Cleavage of Ether Bond in a Lignin Model Compound over Carbon-Supported Noble Metal Catalysts in Supercritical Ethanol
title_fullStr Catalytic Cleavage of Ether Bond in a Lignin Model Compound over Carbon-Supported Noble Metal Catalysts in Supercritical Ethanol
title_full_unstemmed Catalytic Cleavage of Ether Bond in a Lignin Model Compound over Carbon-Supported Noble Metal Catalysts in Supercritical Ethanol
title_sort catalytic cleavage of ether bond in a lignin model compound over carbon-supported noble metal catalysts in supercritical ethanol
publisher MDPI AG
series Catalysts
issn 2073-4344
publishDate 2019-02-01
description Decomposition of lignin-related model compound (benzyl phenyl ether, BPE) to phenol and toluene was performed over carbon-supported noble metal (Ru, Pd, and Pt) catalysts in supercritical ethanol without supply of hydrogen. Phenol and toluene as target products were produced by the hydrogenolysis of BPE. The conversion of BPE was higher than 95% over all carbon-supported noble metal catalysts at 270 °C for 4 h. The 5 wt% Pd/C demonstrated the highest yield (ca. 59.3%) of the target products and enhanced conversion rates and reactivity more significantly than other catalysts. In the case of Ru/C, BPE was significantly transformed to other unidentified byproducts, more so than other catalysts. The Pt/C catalyst produced the highest number of byproducts such as alkylated phenols and gas-phase products, indicating that the catalyst promotes secondary reactions during the decomposition of BPE. In addition, a model reaction using phenol as a reactant was conducted to check the secondary reactions of phenol such as alkylation or hydrogenation in supercritical ethanol. The product distribution when phenol was used as a reactant was mostly consistent with BPE as a reactant. Based on the results, plausible reaction pathways were proposed.
topic benzyl phenyl ether
solvolysis
supercritical ethanol
carbon-supported noble metal catalysts
url https://www.mdpi.com/2073-4344/9/2/158
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AT soyeonjeong catalyticcleavageofetherbondinaligninmodelcompoundovercarbonsupportednoblemetalcatalystsinsupercriticalethanol
AT chunghyeonban catalyticcleavageofetherbondinaligninmodelcompoundovercarbonsupportednoblemetalcatalystsinsupercriticalethanol
AT hyungjookim catalyticcleavageofetherbondinaligninmodelcompoundovercarbonsupportednoblemetalcatalystsinsupercriticalethanol
AT doheuikim catalyticcleavageofetherbondinaligninmodelcompoundovercarbonsupportednoblemetalcatalystsinsupercriticalethanol
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