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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

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.

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 Creators:
Geboers, Jan1, Author              
Wang, Xingyu2, Author              
De Carvalho, Alex Bruno1, Author
Rinaldi, Roberto2, Author              
Affiliations:
1Research Department Schüth, Max-Planck-Institut für Kohlenforschung, Max Planck Society, Kaiser-Wilhelm-Platz 1, 45470 Mülheim an der Ruhr, DE, ou_1445589              
2Research Group Rinaldi, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445617              

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Free keywords: γ-Valerolactone; Alkyl γ-hydroxypentanoates; Raney Ni; Transfer hydrogenation; One-pot synthesis
 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.

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 Dates: 2013-12-072014-07
 Publication Status: Published in print
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 Table of Contents: -
 Rev. Type: -
 Identifiers: DOI: 10.1016/j.molcata.2013.11.031
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Title: Journal of Molecular Catalysis A
Source Genre: Journal
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Publ. Info: Amsterdam : Elsevier
Pages: - Volume / Issue: (388-389) Sequence Number: - Start / End Page: 106 - 115 Identifier: ISSN: 1381-1169
CoNE: https://pure.mpg.de/cone/journals/resource/954925621184