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Selective Aerobic Benzylic Alcohol Oxidation of Lignin Model Compounds: Route to Aryl Ketones
Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC.
Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC.
Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC.
2015 (Engelska)Ingår i: ChemCatChem, ISSN 1867-3880, E-ISSN 1867-3899, Vol. 7, nr 3, s. 401-404Artikel i tidskrift (Refereegranskat) Published
Abstract [en]

A mild and chemoselective oxidation of the -alcohol in -O-4-ethanoaryl and -O-4-glycerolaryl ethers has been developed. The benzylic alcohols were selectively dehydrogenated to the corresponding ketones in 60-93% yield. A one-pot selective route to aryl ethyl ketones was performed. The catalytic system comprises recyclable heterogeneous palladium, mild reaction conditions, green solvents, and oxygen in air as oxidant. Catalytic amounts of a coordinating polyol were found pivotal for an efficient aerobic oxidation.

Ort, förlag, år, upplaga, sidor
2015. Vol. 7, nr 3, s. 401-404
Nyckelord [en]
biomass valorization, heterogeneous catalysis, lignin, oxidation, palladium
Nationell ämneskategori
Kemi
Identifikatorer
URN: urn:nbn:se:uu:diva-246820DOI: 10.1002/cctc.201402825ISI: 000349147100005OAI: oai:DiVA.org:uu-246820DiVA, id: diva2:794379
Tillgänglig från: 2015-03-11 Skapad: 2015-03-10 Senast uppdaterad: 2017-12-04Bibliografiskt granskad
Ingår i avhandling
1. Palladium-catalyzed lignin valorization: Towards a lignin-based biorefinery
Öppna denna publikation i ny flik eller fönster >>Palladium-catalyzed lignin valorization: Towards a lignin-based biorefinery
2015 (Engelska)Doktorsavhandling, sammanläggning (Övrigt vetenskapligt)
Abstract [en]

The work described in this thesis focuses on the cleavage of the β-O-4′ bond, which is the most abundant interunit linkage in the lignin polymer.

In the first part, three methods based on palladium catalysis have been developed and their applicability has been verified using lignin model compounds. A transfer hydrogenolysis of the β-O-4′ bond using formic acid as a mild hydrogen donor together with a base. An aerobic oxidation of the benzylic alcohol motif in the β-O-4′ linkage to generate a key intermediate in the cleavage reaction was performed. A redox neutral cleavage of the β-O-4′ bond was accomplished in which no stoichiometric reducing or oxidizing agents were added.

In the second part of the thesis, a mechanistic study is presented. The corresponding ketone from a dehydrogenation reaction of the benzylic alcohol motif was identified to be the key intermediate. This ketone and its enol tautomer was found to be responsible for the β-O-4′ bond cleavage reaction under the employed reaction conditions.

In the final part of this thesis, the methodologies have been applied to native lignin. The depolymerization reaction was combined with organosolv pulping. This approach was successful, and together with cellulose and hemicellulose, propenyl aryls were generated in excellent yields directly from wood. In this transformation, the lignin derived molecules have been reduced by an endogenous hydrogen donor from the wood.

Ort, förlag, år, upplaga, sidor
Uppsala: Acta Universitatis Upsaliensis, 2015. s. 56
Serie
Digital Comprehensive Summaries of Uppsala Dissertations from the Faculty of Science and Technology, ISSN 1651-6214 ; 1310
Nyckelord
Lignin, Heterogeneous Catalysis, Palladium, Biomass, Depolymerization, Reduction, Oxidation, Biorefinery, Transfer Hydrogenolysis
Nationell ämneskategori
Organisk kemi Polymerkemi Trävetenskap
Forskningsämne
Organisk kemi
Identifikatorer
urn:nbn:se:uu:diva-265315 (URN)978-91-554-9393-6 (ISBN)
Disputation
2015-12-14, B:22, Uppsala Biomedical Centre (BMC), Husargatan 3, Uppsala, 09:30 (Engelska)
Opponent
Handledare
Tillgänglig från: 2015-11-23 Skapad: 2015-10-27 Senast uppdaterad: 2016-01-13

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Galkin, Maxim V.Samec, Joseph S. M.

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