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

Handle URI:
http://hdl.handle.net/10754/565866
Title:
Gold-catalyzed aerobic epoxidation of trans-stilbene in methylcyclohexane. Part II: Identification and quantification of a key reaction intermediate
Authors:
Guillois, Kevin; Mangematin, Stéphane; Tuel, Alain; Caps, Valerie
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.
KAUST Department:
KAUST Catalysis Center (KCC)
Publisher:
Elsevier BV
Journal:
Catalysis Today
Conference/Event name:
10th European Workshop Meeting on Selective Oxidation, The Silver Jubilee Meeting" Selectivity: the Key to Sustainability "
Issue Date:
Mar-2013
DOI:
10.1016/j.cattod.2012.03.031
Type:
Conference Paper
ISSN:
09205861
Sponsors:
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).
Appears in Collections:
Conference Papers; KAUST Catalysis Center (KCC)

Full metadata record

DC FieldValue Language
dc.contributor.authorGuillois, Kevinen
dc.contributor.authorMangematin, Stéphaneen
dc.contributor.authorTuel, Alainen
dc.contributor.authorCaps, Valerieen
dc.date.accessioned2015-08-11T13:44:07Zen
dc.date.available2015-08-11T13:44:07Zen
dc.date.issued2013-03en
dc.identifier.issn09205861en
dc.identifier.doi10.1016/j.cattod.2012.03.031en
dc.identifier.urihttp://hdl.handle.net/10754/565866en
dc.description.abstractThe 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.en
dc.description.sponsorshipFunding 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).en
dc.publisherElsevier BVen
dc.subjectAerobicen
dc.subjectCatalysisen
dc.subjectCo-oxidationen
dc.subjectGolden
dc.subjectHydroperoxideen
dc.titleGold-catalyzed aerobic epoxidation of trans-stilbene in methylcyclohexane. Part II: Identification and quantification of a key reaction intermediateen
dc.typeConference Paperen
dc.contributor.departmentKAUST Catalysis Center (KCC)en
dc.identifier.journalCatalysis Todayen
dc.conference.date28 August–2 September 2011en
dc.conference.name10th European Workshop Meeting on Selective Oxidation, The Silver Jubilee Meeting" Selectivity: the Key to Sustainability "en
dc.conference.locationGlasgow, U.Ken
kaust.authorCaps, Valerieen
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