Aromatic-Hydroxyl Interaction of a Lignin Model Compound on SBA-15, Present at Pyrolysis Temperatures
Abstract
An aromatic alpha-aryl ether compound (a benzyl phenyl ether analogue) was covalently grafted to mesoporous silica SBA-15, to create BPEa-SBA-15. The BPEa-SBA-15 was subjected to successive heating cycles up to 600 °C, with in situ monitoring by DRIFTS. It was found that the toluene moiety coordinates to SBA-15 surface silanol hydroxyl groups via an aromatic–hydroxyl interaction. This interaction is evidenced by a red-shift of the aromatic C–H stretches, as well as a red-shift and broadening of the surface hydroxyl O–H stretches, which are features characteristic of a hydrogen bond. These features remain present during heating until ~400 °C whereupon the ether linkage of BPEa-SBA-15 is cleaved, accompanied by loss of the toluene moiety.
- Authors:
-
- Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)
- Publication Date:
- Research Org.:
- Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States). Center for Nanophase Materials Sciences (CNMS)
- Sponsoring Org.:
- USDOE Office of Science (SC)
- OSTI Identifier:
- 1162065
- Grant/Contract Number:
- AC05-00OR22725
- Resource Type:
- Accepted Manuscript
- Journal Name:
- Physical Chemistry Chemical Physics. PCCP
- Additional Journal Information:
- Journal Volume: 16; Journal Issue: 44; Journal ID: ISSN 1463-9076
- Publisher:
- Royal Society of Chemistry
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Citation Formats
Kandziolka, III, Michael V., Kidder, Michelle, Gill, Lance W., Wu, Zili, and Savara, Aditya Ashi. Aromatic-Hydroxyl Interaction of a Lignin Model Compound on SBA-15, Present at Pyrolysis Temperatures. United States: N. p., 2014.
Web. doi:10.1039/C4CP02633K.
Kandziolka, III, Michael V., Kidder, Michelle, Gill, Lance W., Wu, Zili, & Savara, Aditya Ashi. Aromatic-Hydroxyl Interaction of a Lignin Model Compound on SBA-15, Present at Pyrolysis Temperatures. United States. https://doi.org/10.1039/C4CP02633K
Kandziolka, III, Michael V., Kidder, Michelle, Gill, Lance W., Wu, Zili, and Savara, Aditya Ashi. Mon .
"Aromatic-Hydroxyl Interaction of a Lignin Model Compound on SBA-15, Present at Pyrolysis Temperatures". United States. https://doi.org/10.1039/C4CP02633K. https://www.osti.gov/servlets/purl/1162065.
@article{osti_1162065,
title = {Aromatic-Hydroxyl Interaction of a Lignin Model Compound on SBA-15, Present at Pyrolysis Temperatures},
author = {Kandziolka, III, Michael V. and Kidder, Michelle and Gill, Lance W. and Wu, Zili and Savara, Aditya Ashi},
abstractNote = {An aromatic alpha-aryl ether compound (a benzyl phenyl ether analogue) was covalently grafted to mesoporous silica SBA-15, to create BPEa-SBA-15. The BPEa-SBA-15 was subjected to successive heating cycles up to 600 °C, with in situ monitoring by DRIFTS. It was found that the toluene moiety coordinates to SBA-15 surface silanol hydroxyl groups via an aromatic–hydroxyl interaction. This interaction is evidenced by a red-shift of the aromatic C–H stretches, as well as a red-shift and broadening of the surface hydroxyl O–H stretches, which are features characteristic of a hydrogen bond. These features remain present during heating until ~400 °C whereupon the ether linkage of BPEa-SBA-15 is cleaved, accompanied by loss of the toluene moiety.},
doi = {10.1039/C4CP02633K},
journal = {Physical Chemistry Chemical Physics. PCCP},
number = 44,
volume = 16,
place = {United States},
year = {Mon Jul 14 00:00:00 EDT 2014},
month = {Mon Jul 14 00:00:00 EDT 2014}
}
Web of Science
Works referenced in this record:
Quantitative Diffuse Reflectance and Diffuse Transmittance Infrared Spectroscopy of Surface-Derivatized Silica Powders
journal, July 1994
- Boroumand, Farnaz.; van den Bergh, Hubert.; Moser, Jacques E.
- Analytical Chemistry, Vol. 66, Issue 14
Useful Products from Complex Starting Materials: Common Chemicals from Biomass Feedstocks
journal, April 2010
- Marshall, Amanda-Lynn; Alaimo, Peter J.
- Chemistry - A European Journal, Vol. 16, Issue 17
Hydrogen bonding ligand functionality and catalytic selectivity in homogeneous hydrosilylation of enones with rhodium complexes
journal, November 2004
- Rivera, Guillermina; Crabtree, Robert H.
- Journal of Molecular Catalysis A: Chemical, Vol. 222, Issue 1-2
Predicting Hydrogen-Bond Strengths from Acid−Base Molecular Properties. The p K a Slide Rule: Toward the Solution of a Long-Lasting Problem
journal, January 2009
- Gilli, Paola; Pretto, Loretta; Bertolasi, Valerio
- Accounts of Chemical Research, Vol. 42, Issue 1
Cation−π Interaction: Its Role and Relevance in Chemistry, Biology, and Material Science
journal, November 2012
- Mahadevi, A. Subha; Sastry, G. Narahari
- Chemical Reviews, Vol. 113, Issue 3
In situ catalytic upgrading of biomass derived fast pyrolysis vapours in a fixed bed reactor using mesoporous materials
journal, November 2006
- Adam, Judit; Antonakou, Eleni; Lappas, Angelos
- Microporous and Mesoporous Materials, Vol. 96, Issue 1-3
Asymmetric Catalysis by Chiral Hydrogen-Bond Donors
journal, February 2006
- Taylor, Mark S.; Jacobsen, Eric N.
- Angewandte Chemie International Edition, Vol. 45, Issue 10
Bio-oil hydrodeoxygenation: Adsorption of phenolic compounds on sulfided (Co)Mo catalysts
journal, January 2013
- Popov, Andrey; Kondratieva, Elena; Mariey, Laurence
- Journal of Catalysis, Vol. 297
Molecular Recognition in the Selective Oxygenation of Saturated C-H Bonds by a Dimanganese Catalyst
journal, June 2006
- Das, S.
- Science, Vol. 312, Issue 5782
Catalytic Hydrocracking of Pyrolytic Lignin to Liquid Fuel in Supercritical Ethanol
journal, March 2010
- Tang, Zhe; Zhang, Ying; Guo, Qingxiang
- Industrial & Engineering Chemistry Research, Vol. 49, Issue 5
Synthesis of Transportation Fuels from Biomass: Chemistry, Catalysts, and Engineering
journal, September 2006
- Huber, George W.; Iborra, Sara; Corma, Avelino
- Chemical Reviews, Vol. 106, Issue 9, p. 4044-4098
The influence of hydroxyl groups on the ultraviolet spectra of substituted aromatic molecules adsorbed on silica surfaces
journal, March 1975
- Anderson, J. H.; Lombardi, John; Hair, M. L.
- Journal of Colloid and Interface Science, Vol. 50, Issue 3
Activation of Carbonyl Compounds by Double Hydrogen Bonding: An Emerging Tool in Asymmetric Catalysis
journal, April 2004
- Pihko, Petri M.
- Angewandte Chemie International Edition, Vol. 43, Issue 16
Infrared study of the adsorption of aromatic molecules onto silica and chlorinated silica. Application of the charge-transfer theory to the data
journal, January 1982
- Pohle, Walter
- Journal of the Chemical Society, Faraday Transactions 1: Physical Chemistry in Condensed Phases, Vol. 78, Issue 7
Catalytic Fast Pyrolysis of Lignin Over Mesoporous Y Zeolite Using Py-GC/MS
journal, April 2013
- Lee, Hyung Won; Kim, Tae Hwan; Park, Sung Hoon
- Journal of Nanoscience and Nanotechnology, Vol. 13, Issue 4
Fourier transform infrared spectroscopic studies of the adsorption of benzene on alumina and alumina supported platinum
journal, January 1981
- Haaland, David M.
- Surface Science, Vol. 102, Issue 2-3
Pyrolysis of Benzyl Phenyl Ether Confined in Mesoporous Silica
journal, January 2006
- Kidder, Michelle K.; Britt, Phillip F.; Buchanan, A. C.
- Energy & Fuels, Vol. 20, Issue 1
Renewable Chemical Commodity Feedstocks from Integrated Catalytic Processing of Pyrolysis Oils
journal, November 2010
- Vispute, T. P.; Zhang, H.; Sanna, A.
- Science, Vol. 330, Issue 6008
Interaction of benzene with hydroxyl groups in zeolites: A FTIR study of C6H6 and C6D6 adsorption on H-ZSM-5 and D-ZSM-5
journal, August 2011
- Chakarova, Kristina; Hadjiivanov, Konstantin
- Microporous and Mesoporous Materials, Vol. 143, Issue 1
An FT-IR study of the internal and external surfaces of HZSM5 zeolite
journal, February 2000
- Trombetta, Marcella; Armaroli, Tiziana; Gutièrrez Alejandre, Aı̀da
- Applied Catalysis A: General, Vol. 192, Issue 1
Patterns in Hydrogen Bonding: Functionality and Graph Set Analysis in Crystals
journal, August 1995
- Bernstein, Joel; Davis, Raymond E.; Shimoni, Liat
- Angewandte Chemie International Edition in English, Vol. 34, Issue 15
A mechanistic model of fast pyrolysis of glucose-based carbohydrates to predict bio-oil composition
journal, January 2012
- Vinu, R.; Broadbelt, Linda J.
- Energy & Environmental Science, Vol. 5, Issue 12
Hydrodeoxygenation of Guaiacol, A Surrogate of Lignin Pyrolysis Vapors, Over Iron Based Catalysts: Kinetics and Modeling of the Lignin to Aromatics Integrated Process
journal, January 2013
- Olcese, R. N.; Francois, J.; Bettahar, M. M.
- Energy & Fuels, Vol. 27, Issue 2
Unraveling the Reactions that Unravel Cellulose
journal, June 2012
- Mayes, Heather B.; Broadbelt, Linda J.
- The Journal of Physical Chemistry A, Vol. 116, Issue 26
Adsorption of toluene on Si(100)/SiO2 substrate and mesoporous SBA-15
journal, January 2006
- Mirji, S. A.; Halligudi, S. B.; Sawant, Dhanashri P.
- Colloids and Surfaces A: Physicochemical and Engineering Aspects, Vol. 272, Issue 3
Raman spectra of benzene adsorbed at the aqueous/silica and vapor/silica interfaces
journal, February 1983
- Sayed, Moein B.; Cooney, Ralph P.
- Journal of Colloid and Interface Science, Vol. 91, Issue 2
Quantitative Analysis of Adsorbate Concentrations by Diffuse Reflectance FT-IR
journal, May 2007
- Sirita, Jinda; Phanichphant, Sukon; Meunier, Frederic C.
- Analytical Chemistry, Vol. 79, Issue 10
FT-IR Investigation of Methoxy Substituted Benzenes Adsorbed on Solid Acid Catalysts
journal, October 2012
- Lucarelli, C.; Giugni, A.; Moroso, G.
- The Journal of Physical Chemistry C, Vol. 116, Issue 40
Towards Quantitative Catalytic Lignin Depolymerization
journal, April 2011
- Roberts, Virginia. M.; Stein, Valentin; Reiner, Thomas
- Chemistry - A European Journal, Vol. 17, Issue 21, p. 5939-5948
Bio-oils Hydrodeoxygenation: Adsorption of Phenolic Molecules on Oxidic Catalyst Supports
journal, August 2010
- Popov, Andrey; Kondratieva, Elena; Goupil, Jean Michel
- The Journal of Physical Chemistry C, Vol. 114, Issue 37
Surface Interactions of Glycerol with Acidic and Basic Metal Oxides
journal, October 2013
- Copeland, John R.; Santillan, Ivan A.; Schimming, Sarah McNew
- The Journal of Physical Chemistry C, Vol. 117, Issue 41
Pyrolysis of Mesoporous Silica-Immobilized 1,3-Diphenylpropane. Impact of Pore Confinement and Size
journal, May 2005
- Kidder, Michelle K.; Britt, Phillip F.; Zhang, Zongtao
- Journal of the American Chemical Society, Vol. 127, Issue 17
Aromatics Production via Catalytic Pyrolysis of Pyrolytic Lignins from Bio-Oil
journal, October 2010
- Zhao, Yan; Deng, Li; Liao, Bin
- Energy & Fuels, Vol. 24, Issue 10
Toward Low-Temperature Dehydrogenation Catalysis: Isophorone Adsorbed on Pd(111)
journal, February 2012
- Liu, Wei; Savara, Aditya; Ren, Xinguo
- The Journal of Physical Chemistry Letters, Vol. 3, Issue 5
Merging Organocatalysis and Gold Catalysis-A Critical Evaluation of the Underlying Concepts
journal, June 2012
- Loh, Charles C. J.; Enders, Dieter
- Chemistry - A European Journal, Vol. 18, Issue 33
Elucidation of Intermediates and Mechanisms in Heterogeneous Catalysis Using Infrared Spectroscopy
journal, April 2014
- Savara, Aditya; Weitz, Eric
- Annual Review of Physical Chemistry, Vol. 65, Issue 1
Adsorption Entropies and Enthalpies and Their Implications for Adsorbate Dynamics
journal, January 2009
- Savara, Aditya; Schmidt, Catherine M.; Geiger, Franz M.
- The Journal of Physical Chemistry C, Vol. 113, Issue 7
Pyrolysis of Silica-Immobilized Benzyl Phenyl Ether: Competing Radical Rearrangement Pathways under Restricted Diffusion
journal, December 1998
- Buchanan, A. C.; Britt, Phillip F.; Skeen, J. Todd
- The Journal of Organic Chemistry, Vol. 63, Issue 26
Silica-Supported, Single-Site Titanium Catalysts for Olefin Epoxidation. A Molecular Precursor Strategy for Control of Catalyst Structure
journal, July 2002
- Jarupatrakorn, Jonggol; Tilley, T. Don
- Journal of the American Chemical Society, Vol. 124, Issue 28
A Bond by Any Other Name
journal, October 2010
- Desiraju, Gautam R.
- Angewandte Chemie International Edition, Vol. 50, Issue 1
Universal Features of the Electron Density Distribution in Hydrogen-Bonding Regions: A Comprehensive Study Involving H⋅⋅⋅X (X=H, C, N, O, F, S, Cl, π) Interactions
journal, February 2010
- Mata, Ignasi; Alkorta, Ibon; Molins, Elies
- Chemistry - A European Journal, Vol. 16, Issue 8
Definition of the hydrogen bond (IUPAC Recommendations 2011)
journal, July 2011
- Arunan, Elangannan; Desiraju, Gautam R.; Klein, Roger A.
- Pure and Applied Chemistry, Vol. 83, Issue 8
Activation of Carbonyl Compounds by Double Hydrogen Bonding: An Emerging Tool in Asymmetric Catalysis.
journal, June 2004
- Pihko, Petri M.
- ChemInform, Vol. 35, Issue 26
Synthesis of Transportation Fuels from Biomass: Chemistry, Catalysts, and Engineering
journal, December 2006
- Huber, George W.; Iborra, Sara; Corma, Avelino
- ChemInform, Vol. 37, Issue 52
Fourier transform infrared spectroscopic studies of the adsorption of benzene on alumina and alumina supported platinum
journal, January 1981
- Haaland, DavidM.
- Surface Science Letters, Vol. 102, Issue 2-3
Asymmetric Catalysis by Chiral Hydrogen-Bond Donors
journal, May 2006
- Taylor, Mark S.; Jacobsen, Eric N.
- ChemInform, Vol. 37, Issue 22
Works referencing / citing this record:
Selective Benzyl Alcohol Oxidation over Pd Catalysts
journal, September 2018
- Chan-Thaw, Carine; Savara, Aditya; Villa, Alberto
- Catalysts, Vol. 8, Issue 10
Solvation effect on binding modes of model lignin dimer compounds on MWW 2D-zeolite
journal, September 2019
- Jain, Varsha; Wilson, Woodrow N.; Rai, Neeraj
- The Journal of Chemical Physics, Vol. 151, Issue 11
Pyrolysis treatment of nonmetal fraction of waste printed circuit boards: Focusing on the fate of bromine
journal, January 2020
- Xiong, Jingjing; Yu, Shaoqi; Wu, Daidai
- Waste Management & Research: The Journal for a Sustainable Circular Economy, Vol. 38, Issue 11