Issue 10, 2013
From the journal:

Catalysis Science & Technology

Synthesis of natural fragrancejasminaldehyde using silica-immobilized piperazine as organocatalyst

María Pérez-Sáncheza  and  Pablo Domínguez de María*a  

* Corresponding authors

a Institut für Technische und Makromolekulare Chemie (ITMC), RWTH Aachen University, Worringerweg 1, 52074 Aachen, Germany
E-mail: dominguez@itmc.rwth-aachen.de
Fax: +49 241 8022177
Tel: +49 241 8020468

Abstract

Jasminaldehyde (α-pentyl cinnamaldehyde) is a natural fragrance that can be produced via aldol-type C–C bond formation between heptanal and benzaldehyde. The use of bases like NaOH to form jasminaldehyde typically leads to significant waste and by-product formation. To provide sustainable options with diminished waste formation and high conversions and selectivities, herein a silica-immobilized piperazine is used as organocatalyst for the jasminaldehyde synthesis either in bio-based solvents (e.g. 2-methyltetrahydrofuran, 2-MeTHF) or in solvent-free conditions (using neat substrates as reaction media). Under reported conditions, a production of ∼7 g jasminaldehyde L−1 h−1 is observed, delivering on-spec conversions and selectivities (>90% each). Selectivity remains unaltered during catalyst recycling, whereas a loss of conversion is significantly observed after reusing the catalyst for several cycles.

Graphical abstract: Synthesis of natural fragrance jasminaldehyde using silica-immobilized piperazine as organocatalyst

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Article information

DOI
https://doi.org/10.1039/C3CY00313B
Article type
Paper
Submitted
06 May 2013
Accepted
09 Jul 2013
First published
09 Jul 2013

Catal. Sci. Technol., 2013,3, 2732-2736

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Synthesis of natural fragrance jasminaldehyde using silica-immobilized piperazine as organocatalyst

M. Pérez-Sánchez and P. D. de María, Catal. Sci. Technol., 2013, 3, 2732 DOI: 10.1039/C3CY00313B

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