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Pd/C-Catalyzed Hydrogenolysis of Dibenzodioxocin Lignin Model Compounds Using Silanes and Water as Hydrogen Source
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Number of Authors: 3
2017 (English)In: ACS Sustainable Chemistry & Engineering, ISSN 2168-0485, Vol. 5, no 5, 3726-3731 p.Article in journal (Refereed) Published
Abstract [en]

A mild Pd/C-catalyzed hydrogenolysis of the C-O bond of model Compounds representing the dibenzodioxocin motif in lignin using polymethylhydrosiloxane (PMHS) and water as hydrogen sources was developed. The efficiency of the reaction is highly dependent on both water Concentration and the addition of a base. The results from mechanistic studies showed that the benzylic C-O bond is cleaved faster than the terminal C-O bond, which only cleaves upon the presence of the neighboring phenol. We propose a hydrogen bond formation between an oxygen atom of an ether group and a proton of a neighboring phenol under the employed mild reaction Conditions, which facilitates cleavage of the C-O bond.

Place, publisher, year, edition, pages
2017. Vol. 5, no 5, 3726-3731 p.
Keyword [en]
Biomass, Lignin, Dibenzodioxocin, PMHS, Hydrogenolysis, Palladium
National Category
Chemical Sciences Chemical Engineering
Identifiers
URN: urn:nbn:se:su:diva-143457DOI: 10.1021/acssuschemeng.7b00428ISI: 000400634900017OAI: oai:DiVA.org:su-143457DiVA: diva2:1106286
Available from: 2017-06-07 Created: 2017-06-07 Last updated: 2017-06-07Bibliographically approved

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Subbotina, ElenaGalkin, Maxim V.Samec, Joseph S. M.
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