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Densification of biorefinery schemes by H-transfer with Raney Ni and 2-propanol: A case study of a potential avenue for valorization of alkyl levulinates to alkyl γ-hydroxypentanoates and γ-valerolactone

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Geboers,  Jan
Research Department Schüth, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Wang,  Xingyu
Research Group Rinaldi, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

De Carvalho,  Alex Bruno
Research Department Schüth, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Rinaldi,  Roberto
Research Group Rinaldi, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Geboers, J., Wang, X., De Carvalho, A. B., & Rinaldi, R. (2014). Densification of biorefinery schemes by H-transfer with Raney Ni and 2-propanol: A case study of a potential avenue for valorization of alkyl levulinates to alkyl γ-hydroxypentanoates and γ-valerolactone. Journal of Molecular Catalysis A, (388-389), 106-115. doi:10.1016/j.molcata.2013.11.031.


Cite as: http://hdl.handle.net/11858/00-001M-0000-0019-DA57-4
Abstract
Alkyl γ-hydroxypentanoates and γ-valerolactone are promising platform chemicals that can be produced from alkyl levulinates in the lignocellulosic biorefinery. Accordingly, this report aims to provide in-depth insight into the molecular aspects involved in the conversion of alkyl levulinates by H-transfer catalyzed by Raney Ni and using 2-propanol as an H-donor and solvent. We demonstrate this methodology as a highly flexible approach in regard to the high degree of control over the product selectivity. In fact, up to 90% yield of alkyl γ-hydroxypentanoates is obtained at temperatures as low as 298 K. In turn, 94% yield of γ-valerolactone is achieved at 393 K. In order to shed light on the fundamental aspects of this chemical route, we address: (1) the energetics of the transfer vs. conventional hydrogenation of methyl levulinate, (2) the thermal stability of methyl γ-hydroxypentanoate in the absence and in the presence of solid catalysts, and (3) the stability of Raney Ni in the conversion of several alkyl levulinates. Lastly, a process concept based on the current results is also proposed. This concept provides a comprehensive overview of the practical possibilities of this process as part of the lignocellulose-based biorefineries.