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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. https://www.osti.gov/servlets/purl/1566769.
@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}
}

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  • Renewable and Sustainable Energy Reviews, Vol. 33
  • DOI: 10.1016/j.rser.2014.01.058

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

Gaussian smearing of spin weight functions in models of phase transitions
journal, December 1983


Oxidized Lignin Depolymerization using Formate Ionic Liquid as Catalyst and Solvent
journal, July 2017


Two-dimensional zeolites: dream or reality?
journal, January 2011

  • Roth, Wieslaw J.; Čejka, Jiří
  • Catalysis Science & Technology, Vol. 1, Issue 1
  • DOI: 10.1039/c0cy00027b

Adsorption of Lignin β-O-4 Dimers on Metal Surfaces in Vacuum and Solvated Environments
journal, December 2018

  • Phongpreecha, Thanaphong; Liu, Jialin; Hodge, David B.
  • ACS Sustainable Chemistry & Engineering, Vol. 7, Issue 2
  • DOI: 10.1021/acssuschemeng.8b05736

Ab initio molecular-dynamics simulation of the liquid-metal–amorphous-semiconductor transition in germanium
journal, May 1994


Heterogeneous catalytic oxidation for lignin valorization into valuable chemicals: what results? What limitations? What trends?
journal, January 2016

  • Behling, R.; Valange, S.; Chatel, G.
  • Green Chemistry, Vol. 18, Issue 7
  • DOI: 10.1039/c5gc03061g

Two-Dimensional Zeolites: Current Status and Perspectives
journal, February 2014

  • Roth, Wieslaw J.; Nachtigall, Petr; Morris, Russell E.
  • Chemical Reviews, Vol. 114, Issue 9
  • DOI: 10.1021/cr400600f

Hydrodeoxygenation of Lignin-Derived Phenols: From Fundamental Studies towards Industrial Applications
journal, September 2017


Review: Oxidation of Lignin Using Ionic Liquids—An Innovative Strategy To Produce Renewable Chemicals
journal, November 2013

  • Chatel, Gregory; Rogers, Robin D.
  • ACS Sustainable Chemistry & Engineering, Vol. 2, Issue 3
  • DOI: 10.1021/sc4004086

Bond cleavage of lignin model compounds into aromatic monomers using supported metal catalysts in supercritical water
journal, April 2017

  • Yamaguchi, Aritomo; Mimura, Naoki; Shirai, Masayuki
  • Scientific Reports, Vol. 7, Issue 1
  • DOI: 10.1038/srep46172

Van der Waals density functionals applied to solids
journal, May 2011


Chemical Pretreatment Methods for the Production of Cellulosic Ethanol: Technologies and Innovations
journal, January 2013

  • Bensah, Edem Cudjoe; Mensah, Moses
  • International Journal of Chemical Engineering, Vol. 2013
  • DOI: 10.1155/2013/719607