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  On the Reactivity of Dihydro‐p‐coumaryl Alcohol towards Reductive Processes Catalyzed by Raney Nickel

Calvaruso, G., Burak, J. A., Clough, M. T., Kennema, M., Meemken, F., & Rinaldi, R. (2017). On the Reactivity of Dihydro‐p‐coumaryl Alcohol towards Reductive Processes Catalyzed by Raney Nickel. ChemCatChem, 9(14), 2627-2632. doi:10.1002/cctc.201601590.

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 Creators:
Calvaruso, Gaetano1, Author           
Burak, Jorge Augusto2, Author           
Clough, Matthew T.3, Author           
Kennema, Marco2, Author           
Meemken, Fabian4, Author
Rinaldi, Roberto5, Author
Affiliations:
1Service Department Theyssen (Technical Labs), Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445632              
2Research Group Rinaldi, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445617              
3Research Department Schüth, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445589              
4Department of Chemistry and Applied Biosciences, ETH Zürich, Zürich, Switzerland, ou_persistent22              
5Department of Chemical Engineering, Imperial College London, London, UK, ou_persistent22              

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Free keywords: biorefining; hydrodeoxygenation; hydrogen transer; lignins; nickel
 Abstract: There are several established approaches for the reductive fractionation of lignocellulose (e.g., “catalytic upstream biorefining” and “lignin‐first” approaches) that lead to a lignin oil product that is composed primarily of dihydro‐p‐monolignols [e.g., 4‐(3‐hydroxypropyl)‐2‐methoxyphenol and 4‐(3‐hydroxypropyl)‐2,6‐dimethoxyphenol]. Although effective catalytic methods have been developed to perform reductive or deoxygenative processes on the lignin oil, the influence of the 3‐hydroxypropyl substituent on catalyst activity has previously been overlooked. Herein, to better understand the reactivity of the depolymerized lignin oil obtained from catalytic upstream biorefining processes, dihydro‐p‐coumaryl alcohol was selected as a model compound. Hydrogenation of this species in the presence of Raney Ni with molecular hydrogen led to ring saturation (100 % selectivity) in the absence of hydrodeoxygenation, whereas under hydrogen‐transfer conditions with 2‐propanol, hydrogenation occurred (≈55 % selectivity) simultaneously with hydrodeoxygenation (≈40 % selectivity). In a broader context, this study sheds light not only on the reactivity of dihydro‐p‐monolignols but also on the intricacies of the catalytic upstream biorefining reaction network in which these species are revealed to be key intermediates in the formation of less‐functionalized p‐alkylphenols.

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Language(s): eng - English
 Dates: 2016-12-062017-02-022017-07-24
 Publication Status: Issued
 Pages: 6
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1002/cctc.201601590
 Degree: -

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Title: ChemCatChem
  Other : ChemCatChem
Source Genre: Journal
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Publ. Info: Weinheim : Wiley-VCH
Pages: - Volume / Issue: 9 (14) Sequence Number: - Start / End Page: 2627 - 2632 Identifier: ISSN: 1867-3880
CoNE: https://pure.mpg.de/cone/journals/resource/1867-3880