Gold-catalyzed aerobic epoxidation of trans-stilbene in methylcyclohexane. Part II: Identification and quantification of a key reaction intermediate

Kevin Guillois; Stéphane Mangematin; Alain Tuel; Valerie Caps

doi:10.1016/j.cattod.2012.03.031

Gold-catalyzed aerobic epoxidation of trans-stilbene in methylcyclohexane. Part II: Identification and quantification of a key reaction intermediate

Kevin Guillois, Stéphane Mangematin, Alain Tuel, Valerie Caps

Physical Sciences and Engineering

Research output: Chapter in Book/Report/Conference proceeding › Conference contribution

18 Scopus citations

Abstract

The gold-catalyzed aerobic oxidations of alkenes are thought to rely on the in situ synthesis of hydroperoxide species, which have however never been clearly identified. Here, we show direct experimental evidence for the presence of 1-methylcyclohexyl hydroperoxide in the aerobic co-oxidation of stilbene and methylcyclohexane catalyzed by the Au/SiO2-R972 optimized catalyst prepared in Part I. Determination of its response in gas chromatography, by triphenylphosphine titration followed by 31P NMR, allows to easily follow its concentration throughout the co-oxidation process and to clearly highlight the simultaneous existence of the methylcyclohexane autoxidation pathway and the stilbene epoxidation pathway. © 2012 Elsevier B.V. All rights reserved.

Original language	English (US)
Title of host publication	Catalysis Today
Publisher	Elsevier BV
Pages	111-115
Number of pages	5
DOIs	https://doi.org/10.1016/j.cattod.2012.03.031
State	Published - Mar 2013

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledgements: Funding of K.G. PhD fellowship by the French National Research Agency (ANR-08-JCJC-0090-01-ACTOGREEN project) is gratefully acknowledged. The authors thank Dr V. Mendez (IRCELYON) for fruitful discussions. This publication is based on work partly supported by Collaborative Travel Funds, made by King Abdullah University of Science and Technology (KAUST).

ASJC Scopus subject areas

General Chemistry
Catalysis

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10.1016/j.cattod.2012.03.031

Cite this

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title = "Gold-catalyzed aerobic epoxidation of trans-stilbene in methylcyclohexane. Part II: Identification and quantification of a key reaction intermediate",

abstract = "The gold-catalyzed aerobic oxidations of alkenes are thought to rely on the in situ synthesis of hydroperoxide species, which have however never been clearly identified. Here, we show direct experimental evidence for the presence of 1-methylcyclohexyl hydroperoxide in the aerobic co-oxidation of stilbene and methylcyclohexane catalyzed by the Au/SiO2-R972 optimized catalyst prepared in Part I. Determination of its response in gas chromatography, by triphenylphosphine titration followed by 31P NMR, allows to easily follow its concentration throughout the co-oxidation process and to clearly highlight the simultaneous existence of the methylcyclohexane autoxidation pathway and the stilbene epoxidation pathway. {\textcopyright} 2012 Elsevier B.V. All rights reserved.",

author = "Kevin Guillois and St{\'e}phane Mangematin and Alain Tuel and Valerie Caps",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: Funding of K.G. PhD fellowship by the French National Research Agency (ANR-08-JCJC-0090-01-ACTOGREEN project) is gratefully acknowledged. The authors thank Dr V. Mendez (IRCELYON) for fruitful discussions. This publication is based on work partly supported by Collaborative Travel Funds, made by King Abdullah University of Science and Technology (KAUST).",

year = "2013",

month = mar,

doi = "10.1016/j.cattod.2012.03.031",

language = "English (US)",

pages = "111--115",

booktitle = "Catalysis Today",

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T1 - Gold-catalyzed aerobic epoxidation of trans-stilbene in methylcyclohexane. Part II: Identification and quantification of a key reaction intermediate

AU - Guillois, Kevin

AU - Mangematin, Stéphane

AU - Tuel, Alain

AU - Caps, Valerie

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: Funding of K.G. PhD fellowship by the French National Research Agency (ANR-08-JCJC-0090-01-ACTOGREEN project) is gratefully acknowledged. The authors thank Dr V. Mendez (IRCELYON) for fruitful discussions. This publication is based on work partly supported by Collaborative Travel Funds, made by King Abdullah University of Science and Technology (KAUST).

PY - 2013/3

Y1 - 2013/3

N2 - The gold-catalyzed aerobic oxidations of alkenes are thought to rely on the in situ synthesis of hydroperoxide species, which have however never been clearly identified. Here, we show direct experimental evidence for the presence of 1-methylcyclohexyl hydroperoxide in the aerobic co-oxidation of stilbene and methylcyclohexane catalyzed by the Au/SiO2-R972 optimized catalyst prepared in Part I. Determination of its response in gas chromatography, by triphenylphosphine titration followed by 31P NMR, allows to easily follow its concentration throughout the co-oxidation process and to clearly highlight the simultaneous existence of the methylcyclohexane autoxidation pathway and the stilbene epoxidation pathway. © 2012 Elsevier B.V. All rights reserved.

AB - The gold-catalyzed aerobic oxidations of alkenes are thought to rely on the in situ synthesis of hydroperoxide species, which have however never been clearly identified. Here, we show direct experimental evidence for the presence of 1-methylcyclohexyl hydroperoxide in the aerobic co-oxidation of stilbene and methylcyclohexane catalyzed by the Au/SiO2-R972 optimized catalyst prepared in Part I. Determination of its response in gas chromatography, by triphenylphosphine titration followed by 31P NMR, allows to easily follow its concentration throughout the co-oxidation process and to clearly highlight the simultaneous existence of the methylcyclohexane autoxidation pathway and the stilbene epoxidation pathway. © 2012 Elsevier B.V. All rights reserved.

UR - http://hdl.handle.net/10754/565866

UR - https://linkinghub.elsevier.com/retrieve/pii/S0920586112001897

UR - http://www.scopus.com/inward/record.url?scp=84873718554&partnerID=8YFLogxK

U2 - 10.1016/j.cattod.2012.03.031

DO - 10.1016/j.cattod.2012.03.031

M3 - Conference contribution

SP - 111

EP - 115

BT - Catalysis Today

PB - Elsevier BV

ER -

Gold-catalyzed aerobic epoxidation of trans-stilbene in methylcyclohexane. Part II: Identification and quantification of a key reaction intermediate

Abstract

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ASJC Scopus subject areas

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