skip to main content
OSTI.GOV title logo U.S. Department of Energy
Office of Scientific and Technical Information

Title: Strategy for Extending the Stability of Bio‐oil‐Derived Phenolic Oligomers by Mild Hydrotreatment with Ionic‐Liquid‐Stabilized Nanoparticles

Abstract

Abstract The development of catalytic transformations and processes is essential to utilize bio‐oil and lignin derivatives. Metal nanoparticles (M‐NPs) stabilized in ionic liquids (ILs) are promising for the catalytic hydrotreatment of bio‐oil because the properties of the catalyst system can be customized by combining the appropriate IL and metal nanoparticles. Herein, we demonstrate an experimental approach to stabilize lignin‐derived phenolics isolated from bio‐oil with ruthenium NPs stabilized by an ionic copolymer in 1‐ethyl‐3‐methylimidazolium acetate ([C 2 C 1 Im][OAc]). The mild hydrotreatment of phenolic oligomers (POs) was performed with the synthesized M‐NP catalyst at 100 °C for 6 h. Hydrotreatment of the POs resulted in enhanced thermal stability of the POs by as much as a factor of three, as determined by the aging index and by reducing reactive functionalities, which was also confirmed by NMR spectroscopy and GC analysis. The results support our hypothesis that M‐NPs stabilized in ILs can effectively stabilize POs under mild conditions, which could be applicable to any lignin‐derived phenolic.

Authors:
 [1];  [2];  [2];  [3];  [4];  [5];  [1]
  1. Deconstruction Division Joint BioEnergy Institute Emeryville CA USA, Biological and Engineering Sciences Center Sandia National Laboratories Livermore CA USA
  2. Bioeconomy Institute Iowa State University Ames IA USA
  3. Molecular Biophysics and Integrated Bioimaging Division Lawrence Berkeley National Laboratory Berkeley CA USA
  4. Deconstruction Division Joint BioEnergy Institute Emeryville CA USA, Molecular Biophysics and Integrated Bioimaging Division Lawrence Berkeley National Laboratory Berkeley CA USA
  5. Deconstruction Division Joint BioEnergy Institute Emeryville CA USA, Biological Systems and Engineering Division Lawrence Berkeley National Laboratory Berkeley CA USA
Publication Date:
Sponsoring Org.:
USDOE
OSTI Identifier:
1401035
Resource Type:
Journal Article: Publisher's Accepted Manuscript
Journal Name:
ChemSusChem
Additional Journal Information:
Journal Name: ChemSusChem Journal Volume: 10 Journal Issue: 5; Journal ID: ISSN 1864-5631
Publisher:
Wiley Blackwell (John Wiley & Sons)
Country of Publication:
Germany
Language:
English

Citation Formats

Kim, Kwang Ho, Brown, Robert C., Daugaard, Tannon, Tivol, William F., Auer, Manfred, Simmons, Blake, and Singh, Seema. Strategy for Extending the Stability of Bio‐oil‐Derived Phenolic Oligomers by Mild Hydrotreatment with Ionic‐Liquid‐Stabilized Nanoparticles. Germany: N. p., 2017. Web. doi:10.1002/cssc.201601515.
Kim, Kwang Ho, Brown, Robert C., Daugaard, Tannon, Tivol, William F., Auer, Manfred, Simmons, Blake, & Singh, Seema. Strategy for Extending the Stability of Bio‐oil‐Derived Phenolic Oligomers by Mild Hydrotreatment with Ionic‐Liquid‐Stabilized Nanoparticles. Germany. https://doi.org/10.1002/cssc.201601515
Kim, Kwang Ho, Brown, Robert C., Daugaard, Tannon, Tivol, William F., Auer, Manfred, Simmons, Blake, and Singh, Seema. 2017. "Strategy for Extending the Stability of Bio‐oil‐Derived Phenolic Oligomers by Mild Hydrotreatment with Ionic‐Liquid‐Stabilized Nanoparticles". Germany. https://doi.org/10.1002/cssc.201601515.
@article{osti_1401035,
title = {Strategy for Extending the Stability of Bio‐oil‐Derived Phenolic Oligomers by Mild Hydrotreatment with Ionic‐Liquid‐Stabilized Nanoparticles},
author = {Kim, Kwang Ho and Brown, Robert C. and Daugaard, Tannon and Tivol, William F. and Auer, Manfred and Simmons, Blake and Singh, Seema},
abstractNote = {Abstract The development of catalytic transformations and processes is essential to utilize bio‐oil and lignin derivatives. Metal nanoparticles (M‐NPs) stabilized in ionic liquids (ILs) are promising for the catalytic hydrotreatment of bio‐oil because the properties of the catalyst system can be customized by combining the appropriate IL and metal nanoparticles. Herein, we demonstrate an experimental approach to stabilize lignin‐derived phenolics isolated from bio‐oil with ruthenium NPs stabilized by an ionic copolymer in 1‐ethyl‐3‐methylimidazolium acetate ([C 2 C 1 Im][OAc]). The mild hydrotreatment of phenolic oligomers (POs) was performed with the synthesized M‐NP catalyst at 100 °C for 6 h. Hydrotreatment of the POs resulted in enhanced thermal stability of the POs by as much as a factor of three, as determined by the aging index and by reducing reactive functionalities, which was also confirmed by NMR spectroscopy and GC analysis. The results support our hypothesis that M‐NPs stabilized in ILs can effectively stabilize POs under mild conditions, which could be applicable to any lignin‐derived phenolic.},
doi = {10.1002/cssc.201601515},
url = {https://www.osti.gov/biblio/1401035}, journal = {ChemSusChem},
issn = {1864-5631},
number = 5,
volume = 10,
place = {Germany},
year = {Fri Feb 17 00:00:00 EST 2017},
month = {Fri Feb 17 00:00:00 EST 2017}
}

Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record at https://doi.org/10.1002/cssc.201601515

Citation Metrics:
Cited by: 1 work
Citation information provided by
Web of Science

Save / Share:

Works referenced in this record:

Characterization of bio-oil recovered as stage fractions with unique chemical and physical properties
journal, January 2012


The effect of pyrolysis temperature on recovery of bio-oil as distinctive stage fractions
journal, January 2014


Formation of phenolic oligomers during fast pyrolysis of lignin
journal, July 2014


Pyrolysis of Wood and Bark in an Auger Reactor: Physical Properties and Chemical Analysis of the Produced Bio-oils
journal, January 2008


Toward Understanding of Bio-Oil Aging: Accelerated Aging of Bio-Oil Fractions
journal, July 2014


Pyrolysis of Wood/Biomass for Bio-oil: A Critical Review
journal, May 2006


Dissolution of cellulose with ionic liquids and its application: a mini-review
journal, January 2006


Characterization of Hydrotreated Fast Pyrolysis Liquids
journal, September 2010


Thermally Reduced Ruthenium Nanoparticles as a Highly Active Heterogeneous Catalyst for Hydrogenation of Monoaromatics
journal, November 2007


Rhodium Nanoparticles Stabilized by Ionic Copolymers in Ionic Liquids:  Long Lifetime Nanocluster Catalysts for Benzene Hydrogenation
journal, July 2005


Graphical Method for Analysis of Ultrahigh-Resolution Broadband Mass Spectra of Natural Organic Matter, the Van Krevelen Diagram
journal, October 2003


Production of Clean Pyrolytic Sugars for Fermentation
journal, April 2014


Dissolution of Wood in Ionic Liquids
journal, October 2007


Fast pyrolysis processes for biomass
journal, March 2000


Ionic Liquid as a Green Solvent for Lignin
journal, April 2007


Kinetics of Aqueous-Phase Hydrogenation of Levoglucosan over Ru/C Catalyst
journal, December 2013


Homogeneous Catalytic Hydrogenation of Bio-Oil and Related Model Aldehydes with RuCl2(PPh3)3
journal, October 2010


Metal Chlorides in Ionic Liquid Solvents Convert Sugars to 5-Hydroxymethylfurfural
journal, June 2007


Selective hydrogenation of biomass derived substrates using ionic liquid-stabilized ruthenium nanoparticles
journal, January 2010


Stabilization of bio-oils using low temperature, low pressure hydrogenation
journal, August 2015


Low temperature hydrogenation of pyrolytic lignin over Ru/TiO 2 : 2D HSQC and 13 C NMR study of reactants and products
journal, January 2016


Secondary reactions of lignin-derived primary tar components
journal, September 2008


Catalytic hydrotreatment of pyrolytic lignins to give alkylphenolics and aromatics using a supported Ru catalyst
journal, January 2014


Hydrocarbon Liquid Production via Catalytic Hydroprocessing of Phenolic Oils Fractionated from Fast Pyrolysis of Red Oak and Corn Stover
journal, April 2015


Hydrodeoxygenation of Lignin-Derived Phenols into Alkanes by Using Nanoparticle Catalysts Combined with Brønsted Acidic Ionic Liquids
journal, June 2010


On the structural and surface properties of transition-metal nanoparticles in ionic liquids
journal, January 2010


Overview of Applications of Biomass Fast Pyrolysis Oil
journal, March 2004


Identification of free radicals in pyrolysis oil and their impact on bio-oil stability
journal, January 2014


The Use of Imidazolium Ionic Liquids for the Formation and Stabilization of Ir0 and Rh0 Nanoparticles: Efficient Catalysts for the Hydrogenation of Arenes
journal, July 2003


Catalyst studies on the hydrotreatment of fast pyrolysis oil
journal, August 2010


Ionic liquid-stabilized nanoparticles as catalysts for the conversion of biomass
journal, January 2015