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Ductile Pd-Catalysed Hydrodearomatization of Phenol-Containing Bio-Oils Into Either Ketones or Alcohols using PMHS and H2O 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.
Stockholm University, Faculty of Science, Department of Organic Chemistry.ORCID iD: 0000-0001-8735-5397
Number of Authors: 42018 (English)In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 360, no 20, p. 3924-3929Article in journal (Refereed) Published
Abstract [en]

A series of phenolic bio-oil components were selectively hydrodearomatized by palladium on carbon into the corresponding ketones or alcohols in excellent yields using polymethylhydrosiloxane and water as reducing agent. The selectivity of the reaction was governed by the water concentration where selectivity to alcohol was favoured at higher water concentrations. As phenolic bio-oil examples cardanol and beech wood tar creosote were studied as substrate to the developed reaction conditions. Cardanol was hydrodearomatized into 3-pentadecylcyclohexanone in excellent yield. From beech wood tar creosote, a mixture of cyclohexanols was produced. No hydrodeoxygenation occurred, suggesting the applicability of the reported method for the production of ketone-alcohol oil from biomass.

Place, publisher, year, edition, pages
2018. Vol. 360, no 20, p. 3924-3929
Keywords [en]
Beech wood tar creosote, Bio-oil, Cardanol, Heterogeneous catalysis, Hydrodearomatization, Palladium
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:su:diva-161930DOI: 10.1002/adsc.201800614ISI: 000447633800011OAI: oai:DiVA.org:su-161930DiVA, id: diva2:1262701
Available from: 2018-11-12 Created: 2018-11-12 Last updated: 2022-02-26Bibliographically approved
In thesis
1. Catalytic valorization of lignocellulose: Direct and sidestream upgrading approaches
Open this publication in new window or tab >>Catalytic valorization of lignocellulose: Direct and sidestream upgrading approaches
2021 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

This work aims to explore different approaches for the valorization of lignocellulosic biomass. In this regard, two different strategies are presented: the catalytic upgrading of lignocellulose derivatives from industrial streams, such as pyrolytic oil and kraft lignin, and the direct catalytic fractionation of woody biomass. The first approach is explored in Paper I and II, while the second in Paper III and IV.

Different phenolic compounds were hydro-dearomatized using a heterogeneous catalytic system based on Pd/C and polymethylhydrosiloxane/H2O as a liquid hydrogen source. High yields of either cyclohexanones or cyclohexanols were achieved in high selectivity by varying the concentration of water. To prove the broad applicability of the method, commercially available bio-oils such as beechwood tar creosote and cardanol oil underwent hydrodearomatization using the developed catalytic systems (Paper I).

Kraft lignin, a byproduct of the paper manufacturing industry, has been valorized by steering its solubility properties through the production of a lipophilic lignin oil suitable for hydrotreatment. The enhanced solubility allowed its blending in common refinery carriers and full hydrodeoxygenation yielding hydrocarbons in the gasoline-diesel range. A particular focus was set on the mechanistic study of the esterification where a 13C labeling analysis was performed (Paper II).

Untreated birch wood was fractionated into its components while lignin was consequently depolymerized into monophenolic compounds. Cobalt was scrutinized to replace noble metals in reductive catalytic fractionation by synthetizing a heterogeneous catalyst supported on nitrogen-doped carbon. We found that adjusting the pH of the reaction medium affected the yields of the reaction. Under optimized conditions, monophenolic compounds could be obtained in up to 34 wt% yield relative to initial lignin. The role of the catalyst and reductants was investigated (Paper III).

The last chapter describes a pulping system able to parallelly perform the glucan purification and the catalytic upgrade of the lignin by-products while avoiding the contamination of the pulp with the heterogeneous catalyst. The system is based on a high-pressure Soxhlet combined with the ethanol-water organosolv, where Pd/C was selected as the heterogeneous catalyst. Using only CO2 as the acid source, lyocell grade dissolving pulp was produced in addition to lignin oil (Paper IV).

Place, publisher, year, edition, pages
Stockholm: Department of Organic Chemistry, Stockholm University, 2021. p. 65
Keywords
Lignin, biomass, catalytic fractionation, dearomatization, heterogeneous catalysis
National Category
Organic Chemistry
Research subject
Organic Chemistry
Identifiers
urn:nbn:se:su:diva-194071 (URN)978-91-7911-538-8 (ISBN)978-91-7911-539-5 (ISBN)
Public defence
2021-09-10, Magnélisalen, Kemiska övningslaboratoriet, Svante Arrhenius väg 16 B, Stockholm, 15:00 (English)
Opponent
Supervisors
Available from: 2021-08-18 Created: 2021-06-11 Last updated: 2022-02-25Bibliographically approved

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Di Francesco, DavideSubbotina, ElenaRautiainen, SariSamec, Joseph S. M.

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