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

This content will become publicly available on September 20, 2020

Title: Solvation effect on binding modes of model lignin dimer compounds on MWW 2D-zeolite

Abstract

Lignin as a potential renewable source of biofuels, chemicals, and other value-added products has gained much attention. However, the complexity of lignin structure poses a significant challenge for developing efficient valorization techniques. As most processes involve solvothermal conditions to minimize energy cost, lignin depolymerization is governed by reaction conditions (temperature and pressure), and solvents. In this work, binding of β-O-4 linkage consisting lignin dimers on MWW 2-dimensional (2D) zeolite is investigated using periodic density functional theory (DFT). Furthermore, the effect of different terminated surfaces (H:OH % = 100:0; 50:50; 0:100 %), different temperatures (323, 353, 373 K), and different solvents (water and methanol) on the binding modes is quantified. Here, our work shows that in the gas phase the binding strength increases 10 to 15 kcal/mol upon increasing the number of hydroxyl groups on the surface. Also, the phenolic dimer binds more strongly than the non-phenolic dimer, and the binding strength of model compounds increases in the presence of solvent. Analysis of structural changes in the presence of the solvent reveals that aromatic rings are parallel to the zeolite surface and primary interaction with zeolite is through the hydroxyl groups near the β-O-4 linkage. Furthermore, while the solvation energy decreasesmore » with increasing temperature the opposite trend is observed for the binding energy with the surface.« less

Authors:
 [1];  [1]; ORCiD logo [1]
  1. Mississippi State Univ., Mississippi State, MS (United States)
Publication Date:
Research Org.:
Mississippi State Univ., Mississippi State, MS (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22). Chemical Sciences, Geosciences & Biosciences Division
OSTI Identifier:
1566769
Alternate Identifier(s):
OSTI ID: 1563009
Grant/Contract Number:  
SC0018211; AC02-05CH11231
Resource Type:
Accepted Manuscript
Journal Name:
Journal of Chemical Physics
Additional Journal Information:
Journal Volume: 151; Journal Issue: 11; Journal ID: ISSN 0021-9606
Publisher:
American Institute of Physics (AIP)
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats

Jain, Varsha, Wilson, Woodrow N., and Rai, Neeraj. Solvation effect on binding modes of model lignin dimer compounds on MWW 2D-zeolite. United States: N. p., 2019. Web. doi:10.1063/1.5112101.
Jain, Varsha, Wilson, Woodrow N., & Rai, Neeraj. Solvation effect on binding modes of model lignin dimer compounds on MWW 2D-zeolite. United States. doi:10.1063/1.5112101.
Jain, Varsha, Wilson, Woodrow N., and Rai, Neeraj. Fri . "Solvation effect on binding modes of model lignin dimer compounds on MWW 2D-zeolite". United States. doi:10.1063/1.5112101.
@article{osti_1566769,
title = {Solvation effect on binding modes of model lignin dimer compounds on MWW 2D-zeolite},
author = {Jain, Varsha and Wilson, Woodrow N. and Rai, Neeraj},
abstractNote = {Lignin as a potential renewable source of biofuels, chemicals, and other value-added products has gained much attention. However, the complexity of lignin structure poses a significant challenge for developing efficient valorization techniques. As most processes involve solvothermal conditions to minimize energy cost, lignin depolymerization is governed by reaction conditions (temperature and pressure), and solvents. In this work, binding of β-O-4 linkage consisting lignin dimers on MWW 2-dimensional (2D) zeolite is investigated using periodic density functional theory (DFT). Furthermore, the effect of different terminated surfaces (H:OH % = 100:0; 50:50; 0:100 %), different temperatures (323, 353, 373 K), and different solvents (water and methanol) on the binding modes is quantified. Here, our work shows that in the gas phase the binding strength increases 10 to 15 kcal/mol upon increasing the number of hydroxyl groups on the surface. Also, the phenolic dimer binds more strongly than the non-phenolic dimer, and the binding strength of model compounds increases in the presence of solvent. Analysis of structural changes in the presence of the solvent reveals that aromatic rings are parallel to the zeolite surface and primary interaction with zeolite is through the hydroxyl groups near the β-O-4 linkage. Furthermore, while the solvation energy decreases with increasing temperature the opposite trend is observed for the binding energy with the surface.},
doi = {10.1063/1.5112101},
journal = {Journal of Chemical Physics},
number = 11,
volume = 151,
place = {United States},
year = {2019},
month = {9}
}

Journal Article:
Free Publicly Available Full Text
This content will become publicly available on September 20, 2020
Publisher's Version of Record

Save / Share:

Works referenced in this record:

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
  • DOI: 10.1021/cr068360d

Lignin Depolymerization and Conversion A Review of Thermochemical Methods
journal, November 2010

  • Pandey, M. P.; Kim, C. S.
  • Chemical Engineering & Technology, Vol. 34, Issue 1, p. 29-41
  • DOI: 10.1002/ceat.201000270

Catalytic Transformation of Lignin for the Production of Chemicals and Fuels
journal, October 2015


Catalytic conversion of biomass to biofuels
journal, January 2010

  • Alonso, David Martin; Bond, Jesse Q.; Dumesic, James A.
  • Green Chemistry, Vol. 12, Issue 9, p. 1493-1513
  • DOI: 10.1039/c004654j

A Mechanistic Investigation of Acid-Catalyzed Cleavage of Aryl-Ether Linkages: Implications for Lignin Depolymerization in Acidic Environments
journal, November 2013

  • Sturgeon, Matthew R.; Kim, Seonah; Lawrence, Kelsey
  • ACS Sustainable Chemistry & Engineering, Vol. 2, Issue 3, p. 472-485
  • DOI: 10.1021/sc400384w

Efficiency of ab-initio total energy calculations for metals and semiconductors using a plane-wave basis set
journal, July 1996


Hydrogenolysis Goes Bio: From Carbohydrates and Sugar Alcohols to Platform Chemicals
journal, February 2012

  • Ruppert, Agnieszka M.; Weinberg, Kamil; Palkovits, Regina
  • Angewandte Chemie International Edition, Vol. 51, Issue 11, p. 2564-2601
  • DOI: 10.1002/anie.201105125

Ni-Catalyzed Cleavage of Aryl Ethers in the Aqueous Phase
journal, December 2012

  • He, Jiayue; Zhao, Chen; Lercher, Johannes A.
  • Journal of the American Chemical Society, Vol. 134, Issue 51, p. 20768-20775
  • DOI: 10.1021/ja309915e

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
  • DOI: 10.1002/chem.201002438

Recent Development in Chemical Depolymerization of Lignin: A Review
journal, January 2013

  • Wang, Hai; Tucker, Melvin; Ji, Yun
  • Journal of Applied Chemistry, Vol. 2013, p. 1-9
  • DOI: 10.1155/2013/838645

Hydroxycinnamates in lignification
journal, August 2009


Ab Initio Calculation of Vibrational Absorption and Circular Dichroism Spectra Using Density Functional Force Fields
journal, November 1994

  • Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.
  • The Journal of Physical Chemistry, Vol. 98, Issue 45, p. 11623-11627
  • DOI: 10.1021/j100096a001

Lignin Biosynthesis
journal, June 2003


Hydrogen Transfer from Supercritical Methanol over a Solid Base Catalyst A Model for Lignin Depolymerization
journal, March 2009

  • Macala, Gerald S.; Matson, Theodore D.; Johnson, Charles L.
  • ChemSusChem, Vol. 2, Issue 3, p. 215-217
  • DOI: 10.1002/cssc.200900033

The Catalytic Valorization of Lignin for the Production of Renewable Chemicals
journal, June 2010

  • Zakzeski, Joseph; Bruijnincx, Pieter C. A.; Jongerius, Anna L.
  • Chemical Reviews, Vol. 110, Issue 6, p. 3552-3599
  • DOI: 10.1021/cr900354u