Isomerization of alpha-pinene oxide in the presence of methyltrioxorhenium(VII)

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abstract

The catalytic performance of methyltrioxorhenium(VII) (MTO) has been investigated for the first time in the isomerization of a-pinene oxide (PinOx) into campholenic aldehyde (CPA). The high isomerization activity of MTO is coupled with high selectivity to CPA: CPA yield of up to 87% (100% conversion) was obtained by using alpha,alpha,alpha-trifluorotoluene as solvent at 15 degrees C. Catalyst recycling is possible in a relatively simple fashion by using MTO coupled to an appropriate ionic liquid. The catalytic application of MTO in the isomerization of PinOx versus the integrated epoxidation-isomerization process of the conversion of alpha-pinene into CPA is discussed. (C) 2013 Elsevier B.V. All rights reserved.

keywords

LEWIS ACIDITY; CAMPHOLENIC ALDEHYDE; VERSATILE CATALYST; MTO; REARRANGEMENT; SILICA; EPOXIDATION; CHEMISTRY; CHEMICALS; EPOXIDES

subject category

Chemistry

authors

Bruno, SM; Pillinger, M; Kuhn, FE; Goncalves, IS; Valente, AA

our authors

foto Anabela Tavares Aguiar Valente

Anabela Tavares Aguiar Valente

Principal Researcher
foto Isabel Maria de Sousa Gonçalves

Isabel Maria de Sousa Gonçalves

Associate Professor
foto Martyn Pillinger

Martyn Pillinger

Junior Researcher
foto Sofia M. Bruno

Sofia M. Bruno

Assistant Researcher

Groups

1 - inorganic functional nanomaterials and organic-inorganic hybrids
4 - biorefineries, biobased materials and recycling

Projects

Centre for Research in Ceramics and Composite Materials - CICECO (LA0011: 2011-2012) (PEst-C/CTM/LA0011/2011)

acknowledgements

We are grateful to the Fundacao para a Ciencia e a Tecnologia (FCT), the Programa Operacional Ciencia e Inovacao (POCI) 2010, Orcamento do Estado (OE), Fundo Europeu de Desenvolvimento Regional (FEDER) and CICECO (PEst-C/CTM/LA0011/2011), for the general funding. The FCT and the European Social Fund are acknowledged for a post-doctoral grant to S.M.B. (SFRH/BPD/46473/2008). F.E.K. is grateful to the German Research Foundation (DFG) for the financial support (Project No. KU 1265/8-1).

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Publication Details

type
Journal Article
year
2013
journal
CATALYSIS COMMUNICATIONS
volume
35
publisher
ELSEVIER SCIENCE BV
issn
1566-7367
digital object identifier
10.1016/j.catcom.2013.02.001
web of science article identifier
WOS:000317883100009

Journal Metrics (JCR 2019)

Journal Impact Factor
3.612
Journal Impact Factor (5 yrs)
3.458
category normalized journal percentile
60.692

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