A cascade aerobic epoxidation of alkenes over Au/CeO2 and Ti-mesoporous material by "in situ" formed peroxides

Carmela Aprile, Avelino Corma, Marcelo E. Domine, Hermenegildo Garcia, Chris Mitchell

Research output: Contribution to journalArticle

Abstract

The one-pot epoxidation of alkenes with O2 is performed with nano-particulated Au/CeO2 and Ti-MCM-41 silylated materials in the presence of a hydrocarbon and azobis-iso-butyronitrile (AIBN) as a promoter. This initiator is able to form organo-gold species that promote the formation of hydrocarbon (3-methyl-pentane, ethylbenzene, or cumene) hydroperoxides which in the presence of Ti-mesoporous material epoxidize the alkene in good yields. The epoxidation reaction of 1-octene with molecular oxygen (PO2 = 12 bars) at 90 °C over AIBN-Au/CeO2 + Ti-MCM-41-silylated catalytic system results in alkene conversions close to 9% (≈40% of the maximum conversion attainable) with epoxide selectivity around 90% when working with cumene as a sacrificial hydrocarbon.

Original languageEnglish
Pages (from-to)44-53
Number of pages10
JournalJournal of Catalysis
Volume264
Issue number1
DOIs
Publication statusPublished - 15 May 2009

Fingerprint

Mesoporous materials
epoxidation
Epoxidation
Peroxides
Alkenes
peroxides
Hydrocarbons
alkenes
Olefins
cascades
hydrocarbons
Multicarrier modulation
Ethylbenzene
epoxy compounds
Molecular oxygen
pentanes
Epoxy Compounds
initiators
Gold
selectivity

Keywords

  • Aerobic oxidation
  • Alkene epoxidation
  • Gold catalyst
  • Peroxide generation
  • Ti-mesoporous material

Cite this

Aprile, Carmela ; Corma, Avelino ; Domine, Marcelo E. ; Garcia, Hermenegildo ; Mitchell, Chris. / A cascade aerobic epoxidation of alkenes over Au/CeO2 and Ti-mesoporous material by "in situ" formed peroxides. In: Journal of Catalysis. 2009 ; Vol. 264, No. 1. pp. 44-53.
@article{921b547a101e432b8d2b15f8b485eca9,
title = "A cascade aerobic epoxidation of alkenes over Au/CeO2 and Ti-mesoporous material by {"}in situ{"} formed peroxides",
abstract = "The one-pot epoxidation of alkenes with O2 is performed with nano-particulated Au/CeO2 and Ti-MCM-41 silylated materials in the presence of a hydrocarbon and azobis-iso-butyronitrile (AIBN) as a promoter. This initiator is able to form organo-gold species that promote the formation of hydrocarbon (3-methyl-pentane, ethylbenzene, or cumene) hydroperoxides which in the presence of Ti-mesoporous material epoxidize the alkene in good yields. The epoxidation reaction of 1-octene with molecular oxygen (PO2 = 12 bars) at 90 °C over AIBN-Au/CeO2 + Ti-MCM-41-silylated catalytic system results in alkene conversions close to 9{\%} (≈40{\%} of the maximum conversion attainable) with epoxide selectivity around 90{\%} when working with cumene as a sacrificial hydrocarbon.",
keywords = "Aerobic oxidation, Alkene epoxidation, Gold catalyst, Peroxide generation, Ti-mesoporous material",
author = "Carmela Aprile and Avelino Corma and Domine, {Marcelo E.} and Hermenegildo Garcia and Chris Mitchell",
year = "2009",
month = "5",
day = "15",
doi = "10.1016/j.jcat.2009.03.010",
language = "English",
volume = "264",
pages = "44--53",
journal = "Journal of Catalysis",
issn = "0021-9517",
publisher = "Academic Press Inc.",
number = "1",

}

A cascade aerobic epoxidation of alkenes over Au/CeO2 and Ti-mesoporous material by "in situ" formed peroxides. / Aprile, Carmela; Corma, Avelino; Domine, Marcelo E.; Garcia, Hermenegildo; Mitchell, Chris.

In: Journal of Catalysis, Vol. 264, No. 1, 15.05.2009, p. 44-53.

Research output: Contribution to journalArticle

TY - JOUR

T1 - A cascade aerobic epoxidation of alkenes over Au/CeO2 and Ti-mesoporous material by "in situ" formed peroxides

AU - Aprile, Carmela

AU - Corma, Avelino

AU - Domine, Marcelo E.

AU - Garcia, Hermenegildo

AU - Mitchell, Chris

PY - 2009/5/15

Y1 - 2009/5/15

N2 - The one-pot epoxidation of alkenes with O2 is performed with nano-particulated Au/CeO2 and Ti-MCM-41 silylated materials in the presence of a hydrocarbon and azobis-iso-butyronitrile (AIBN) as a promoter. This initiator is able to form organo-gold species that promote the formation of hydrocarbon (3-methyl-pentane, ethylbenzene, or cumene) hydroperoxides which in the presence of Ti-mesoporous material epoxidize the alkene in good yields. The epoxidation reaction of 1-octene with molecular oxygen (PO2 = 12 bars) at 90 °C over AIBN-Au/CeO2 + Ti-MCM-41-silylated catalytic system results in alkene conversions close to 9% (≈40% of the maximum conversion attainable) with epoxide selectivity around 90% when working with cumene as a sacrificial hydrocarbon.

AB - The one-pot epoxidation of alkenes with O2 is performed with nano-particulated Au/CeO2 and Ti-MCM-41 silylated materials in the presence of a hydrocarbon and azobis-iso-butyronitrile (AIBN) as a promoter. This initiator is able to form organo-gold species that promote the formation of hydrocarbon (3-methyl-pentane, ethylbenzene, or cumene) hydroperoxides which in the presence of Ti-mesoporous material epoxidize the alkene in good yields. The epoxidation reaction of 1-octene with molecular oxygen (PO2 = 12 bars) at 90 °C over AIBN-Au/CeO2 + Ti-MCM-41-silylated catalytic system results in alkene conversions close to 9% (≈40% of the maximum conversion attainable) with epoxide selectivity around 90% when working with cumene as a sacrificial hydrocarbon.

KW - Aerobic oxidation

KW - Alkene epoxidation

KW - Gold catalyst

KW - Peroxide generation

KW - Ti-mesoporous material

UR - http://www.scopus.com/inward/record.url?scp=65649125324&partnerID=8YFLogxK

U2 - 10.1016/j.jcat.2009.03.010

DO - 10.1016/j.jcat.2009.03.010

M3 - Article

VL - 264

SP - 44

EP - 53

JO - Journal of Catalysis

JF - Journal of Catalysis

SN - 0021-9517

IS - 1

ER -