Synthesis, spectroscopic characterization and DFT calculations of β-O-4 type lignin model compounds

Mostaghni, Fatemeh; Teimouri, Abbas; Mirshokraei, S A

doi:10.1016/j.saa.2013.03.075

Cited by 11 publications

(5 citation statements)

References 22 publications

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“…Various quantum chemical methods and MD simulations have been explored in understanding structure, [199,200] lignin biosynthesis, [201] lignin pyrolysis, [202] and force-field based modeling of lignin macromolecular assembly [203,204]. Quantum chemical calculations provide insight into molecular information that is inaccessible to conventional experimental techniques.…”

Section: Computational Aspects Of Lignin Linkagesmentioning

confidence: 99%

Recent innovations in analytical methods for the qualitative and quantitative assessment of lignin

Lupoi

Singh

Parthasarathi

et al. 2015

Renewable and Sustainable Energy Reviews

307

188

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a b s t r a c tAs the attraction of creating biofuels and bio-based chemicals from lignocellulosic biomass has increased, researchers have been challenged with developing a better understanding of lignin structure, quantity and potential uses. Lignin has frequently been considered a waste-product from the deconstruction of plant cell walls, in attempts to isolate polysaccharides that can be hydrolyzed and fermented into fuel or other valuable commodities. In order to develop useful applications for lignin, accurate analytical instrumentation and methodologies are required to qualitatively and quantitatively assess, for example, what the structure of lignin looks like or how much lignin comprises a specific feedstock's cellular composition. During the past decade, various diverse strategies have been employed to elucidate the structure and composition of lignin. These techniques include using two-dimensional nuclear magnetic resonance to resolve overlapping spectral data, measuring biomass with vibrational spectroscopy to enable modeling of lignin content or monomeric ratios, methods to probe and quantify the linkages between lignin and polysaccharides, or refinements of established methods to provide higher throughput analyses, less use of consumables, etc. This review seeks to provide a comprehensive overview of many of the advancements achieved in evaluating key lignin attributes. Emphasis is placed on research endeavored in the last decade.

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Section: Computational Aspects Of Lignin Linkagesmentioning

confidence: 99%

Recent innovations in analytical methods for the qualitative and quantitative assessment of lignin

Lupoi

Singh

Parthasarathi

et al. 2015

Renewable and Sustainable Energy Reviews

307

188

View full text Add to dashboard Cite

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“…The application of computational tools to investigate lignin model chemistry has become more common in recent years. Bond breaking during degradation, − coupling of monolignols, − mechanical properties, NMR shifts, , binding energies in ionic liquids, , and reactions involving transition metals , have been studied for various lignin models. Our group focused on the pyrolysis of phenethyl phenyl ethers, which are models for the β-O-4 linkage.…”

Section: Introductionmentioning

confidence: 99%

ReaxFF Study of the Oxidation of Lignin Model Compounds for the Most Common Linkages in Softwood in View of Carbon Fiber Production

Beste

2014

J. Phys. Chem. A

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Lignin is an underused but major component of biomass. One possible area of utilization is the production of carbon fiber. A necessary processing step is the stabilization of lignin fiber (typically in an oxygen environment) before high temperature treatment. We investigate oxidative, thermal conversion of lignin using computational methods. Dilignol model compounds for the most common (seven) linkages in softwood are chosen to represent the diverse structure of lignin. We perform molecular dynamics simulation where the potential energy surface is described by a reactive force field (ReaxFF). We calculate overall activation energies for model conversion and reveal initial mechanisms of formaldehyde formation. We record fragmentation patterns and average carbon oxidation numbers at various temperatures. Most importantly, we identify mechanisms for stabilizing reactions that result in cyclic and rigid connections in softwood lignin fibers that are necessary for further processing into carbon fibers.

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“…Therefore, the DFT calculation was focused upon several model compounds containing different bonds (β-O-4, α-O-4, β-β, β-1, 5-5′, etc.) [ 60 , 61 , 62 , 63 ].…”

Section: Resultsmentioning

confidence: 99%

Sulfation of Wheat Straw Soda Lignin with Sulfamic Acid over Solid Catalysts

et al. 2022

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Soda lignin is a by-product of the soda process for producing cellulose from grassy raw materials. Since a method for the industrial processing of lignin of this type is still lacking, several research teams have been working on solving this problem. We first propose a modification of soda lignin with sulfamic acid over solid catalysts. As solid catalysts for lignin sulfation, modified carbon catalysts (with acid sites) and titanium and aluminum oxides have been used. In the elemental analysis, it is shown that the maximum sulfur content (16.5 wt%) was obtained with the Sibunit-4® catalyst oxidized at 400 °C. The incorporation of a sulfate group has been proven by the elemental analysis and Fourier-transform infrared spectroscopy. The molecular weight distribution has been examined by gel permeation chromatography. It has been demonstrated that the solid catalysts used in the sulfation process causes hydrolysis reactions and reduces the molecular weight and polydispersity index. It has been established by the thermal analysis that sulfated lignin is thermally stabile at temperatures of up to 200 °C. According to the atomic force microscopy data, the surface of the investigated film consists of particles with an average size of 50 nm. The characteristics of the initial and sulfated β-O-4 lignin model compounds have been calculated and recorded using the density functional theory.

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Synthesis, spectroscopic characterization and DFT calculations of β-O-4 type lignin model compounds

Cited by 11 publications

References 22 publications

Recent innovations in analytical methods for the qualitative and quantitative assessment of lignin

Recent innovations in analytical methods for the qualitative and quantitative assessment of lignin

ReaxFF Study of the Oxidation of Lignin Model Compounds for the Most Common Linkages in Softwood in View of Carbon Fiber Production

Sulfation of Wheat Straw Soda Lignin with Sulfamic Acid over Solid Catalysts

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