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
Anabela Tavares Aguiar Valente
Principal Researcher
Isabel Maria de Sousa Gonçalves
Associate Professor
Martyn Pillinger
Principal Researcher
Sofia M. Bruno
Assistant Researcheracknowledgements
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).