Thermal stability of lignin in ground pulp (GP) and the effect of lignin modification on GP’s thermal stability: TGA experiments with dimeric lignin model compounds and milled wood lignins

Holzforschung ◽  
2019 ◽  
Vol 73 (5) ◽  
pp. 493-499 ◽  
Author(s):  
Daisuke Ando ◽  
Fumiaki Nakatsubo ◽  
Hiroyuki Yano
Keyword(s):  
Thermal Stability ◽  
Model Compound ◽  
Pinus Densiflora ◽  
Wood Fiber ◽  
Model Compounds ◽  
Lignin Model Compounds ◽  
Oh Groups ◽  
Lignin Model Compound ◽  
Lignin Model ◽  
Thermal Stability Of

Abstract For ground pulp (GP) utilization in wood fiber composites as reinforced material, its thermal behavior is relevant. The contribution of lignin to thermal performance of GP from Pinus densiflora was the focus of the present study. Dimeric lignin model compounds and isolated milled wood lignins (MWLs) from three sources were submitted for thermogravimetric analysis (TGA). The temperatures leading to 1% weight loss (T per 1% WL) for the material were determined. The thermal stability of β-O-4 models was the lowest. Among the MWLs, the abaca MWL with its high β-O-4 content was the least thermostable. An acetylated nonphenolic β-O-4 lignin model compound showed that acetylation improves the thermal stability of this type of dimeric models. The acetylation of benzylic OH groups in β-O-4 linkages is especially relevant for the thermal resistance, which was also shown based on pre-acetylated benzylic OH groups in the GP before the total acetylation.

scholarly journals Effect of lignin structure on adsorbable organic halogens formation in chlorine dioxide bleaching

2019 ◽  
Vol 6 (2) ◽  
pp. 182024 ◽  
Author(s):  
Lisheng Shi ◽  
Jiayan Ge ◽  
Shuangxi Nie ◽  
Chengrong Qin ◽  
Shuangquan Yao
Keyword(s):  
Chlorine Dioxide ◽  
Model Compound ◽  
Pulp Bleaching ◽  
Model Compounds ◽  
Lignin Model Compounds ◽  
Lignin Model Compound ◽  
Lignin Model ◽  
Organic Halogens ◽  
Adsorbable Organic Halogens ◽  
Lignin Structure

Adsorbable organic halogens (AOX) are formed in pulp bleaching as a result of the reaction of residual lignin with chlorine dioxide. The natural structure of lignin is very complex and it tends to be damaged by various extraction methods. All the factors can affect the study about the mechanism of AOX formation in the reaction of lignin with chlorine dioxide. Lignin model compounds, with certain structures, can be used to study the role of different lignin structures on AOX formation. The effect of lignin structure on AOX formation was determined by reacting phenolic and non-phenolic lignin model compound with a chlorine dioxide solution. Vanillyl alcohol (VA) and veratryl alcohol (VE) were selected for the phenolic and non-phenolic lignin model compound, respectively. The pattern consumption of lignin model compounds suggests that both VA and VE began reacting with chlorine dioxide within 10 min and then gradually steadied. The volume of AOX produced by VE was significantly higher than that produced by VA for a given initial lignin model compound concentration. In a solution containing a combination of VA and VE in chlorine dioxide, VE was the dominant producer of AOX. This result indicates that the non-phenolic lignin structure was more easily chlorinated, while the phenolic lignin structure was mainly oxidized. In addition, AOX content produced in the combined experiments exceeded the total content of the two separate experiments. It suggested that the combination of phenolic and non-phenolic lignin structure can promote AOX formation.

Free radical reaction promoted by ionic liquid: a route for metal-free oxidation depolymerization of lignin model compound and lignin

2015 ◽  
Vol 51 (19) ◽  
pp. 4028-4031 ◽  
Author(s):  
Yingying Yang ◽  
Honglei Fan ◽  
Jinliang Song ◽  
Qinglei Meng ◽  
Huacong Zhou ◽  
...  
Keyword(s):  
Ionic Liquid ◽  
Model Compound ◽  
Radical Reaction ◽  
Free Radical Reaction ◽  
Model Compounds ◽  
Lignin Model Compounds ◽  
Lignin Model Compound ◽  
Organosolv Lignin ◽  
Lignin Model ◽  
Free Oxidation

Ionic liquid can efficiently promote the transformation of lignin model compounds and organosolv lignin.

Synthesis of lignin model compound containing a β-O-4 linkage

2017 ◽  
Vol 72 (2) ◽  
pp. 119-124 ◽  
Author(s):  
Asma Mukhtar ◽  
Muhammad Zaheer ◽  
Muhammad Saeed ◽  
Wolfgang Voelter
Keyword(s):  
Structural Feature ◽  
Model Compound ◽  
Raw Materials ◽  
Value Added ◽  
Model Compounds ◽  
Lignin Model Compounds ◽  
Lignin Model Compound ◽  
Efficient Conversion ◽  
Lignin Model

AbstractDevelopment of catalysts for efficient conversion of lignin polymer to value-added materials requires appropriately-functionalized lignin model compounds. The predominant structural feature of lignin biopolymer is an extensive network of β-O-4 linkages. Access to large amounts of a model compound containing the β-O-4 linkage is crucial for the valorisation of lignin biopolymer to aromatic raw materials. Starting from commercially available vanillin, synthesis of dilignol model compound, containing a β-O-4 linkage, is accomplished in good overall yield.

Polyoxometalate (POM) oxidation of lignin model compounds

Holzforschung ◽  
2008 ◽  
Vol 62 (1) ◽  
pp. 38-49 ◽  
Author(s):  
Yong Sik Kim ◽  
Hou-min Chang ◽  
John F. Kadla
Keyword(s):  
Reaction Rate ◽  
Model Compound ◽  
Reaction Rates ◽  
Hydroxyl Group ◽  
Model Compounds ◽  
Lignin Model Compounds ◽  
Lignin Model Compound ◽  
First Order ◽  
Resonance Stabilization ◽  
Lignin Model

Abstract Various lignin model compounds were oxidized with polyoxometalate (POM), K5[SiVW11O40]·12 H2O, in sodium acetate buffer (I=0.2 M, pH 5.0) and the reaction kinetics were investigated. The reactions were found to have second order reaction rates, first order with regards to both lignin model compound and POM. A dramatic increase in reactivity was observed upon addition of methoxyl groups in ortho-positions to the phenolic hydroxyl group. Syringyl units reacted faster than guaiacyl units. Reaction rates of para-substituted guaiacyl and syringyl model compounds showed a strong dependency on the nature of the substituents. The reaction rate of a 5-5′ dimer lignin model compound was extremely fast. The addition of the ortho-phenol substituent not only increased the electron density of the aromatic ring, but also helped stabilize the intermediate phenoxy radical through resonance stabilization and delocalization.

Recyclable ionic liquid tagged Co(salen) catalysts for the oxidation of lignin model compounds

2013 ◽  
Vol 91 (12) ◽  
pp. 1258-1261 ◽  
Author(s):  
Kenson Ambrose ◽  
Bitu B. Hurisso ◽  
Robert D. Singer
Keyword(s):  
Ionic Liquid ◽  
Liquid Phase ◽  
Model Compound ◽  
Veratryl Alcohol ◽  
Pure Oxygen ◽  
Model Compounds ◽  
Imidazolium Ionic Liquid ◽  
Lignin Model Compounds ◽  
Lignin Model Compound ◽  
Lignin Model

Ionic liquid tagged salen ligands containing two proximal 1,3-disubstituted imidazolium ionic liquid cores form cobalt(III) complexes capable of selectively oxidizing veratryl alcohol, a lignin model compound, to veratraldehyde using air or pure oxygen as the source of oxygen. Entrainment of these catalysts in either 1-butyl-3-methylimidazolium hexafluorophosphate, [bmim][PF6], or 1-butyl-3-methylimidazolium bistriflimide, [bmim][NTf2], hydrophobic ionic liquid solvents, results in biphasic reactions when water is used as the second solvent allowing the catalyst/ionic liquid phase to be recycled.

Oxidative conversion of lignin and lignin model compounds catalyzed by CeO2-supported Pd nanoparticles

2015 ◽  
Vol 17 (11) ◽  
pp. 5009-5018 ◽  
Author(s):  
Weiping Deng ◽  
Hongxi Zhang ◽  
Xuejiao Wu ◽  
Rongsheng Li ◽  
Qinghong Zhang ◽  
...  
Keyword(s):  
Model Compound ◽  
Pd Nanoparticles ◽  
Oxidative Conversion ◽  
Model Compounds ◽  
Lignin Model Compounds ◽  
Lignin Model Compound ◽  
Lignin Model ◽  
Supported Pd

Pd/CeO2 efficiently catalyzes the oxidative conversion of 2-phenoxy-1-phenylethanol, a lignin model compound with a β-O-4 linkage, in methanol, producing monomeric aromatics.

The Reactions of Lignin Model Compounds with Hydrogen Peroxide at Low pH

Holzforschung ◽  
2003 ◽  
Vol 57 (1) ◽  
pp. 52-88 ◽  
Author(s):  
T. Kishimoto ◽  
J. F. Kadla ◽  
H.-m. Chang ◽  
H. Jameel
Keyword(s):  
Hydrogen Peroxide ◽  
Reaction System ◽  
Model Compounds ◽  
Reaction Conditions ◽  
Lignin Model Compounds ◽  
Lignin Model Compound ◽  
Lignin Model ◽  
Decreasing Ph ◽  
Hydroxyl Compounds ◽  
Acidic Hydrogen

Summary In peroxymonosulfuric acid bleaching, the presence of hydrogen peroxide is dependent on the reaction conditions and the conversion ratios used to generate the peroxy acid. Substantial amounts of hydrogen peroxide may be present in the reaction system under certain conditions. An understanding of the reactions of hydrogen peroxide under these conditions would be beneficial. Therefore, several simple lignin model compounds were reacted with acidic hydrogen peroxide, pH 1-3, at 70°C. In all cases the phenolic lignin model compounds reacted much faster than their non-phenolic counterparts. In fact, the extent of reaction was very much dependent on the structure of the lignin model compound. The α-hydroxyl compounds, 4-(1-Hydroxy-ethyl)-2-methoxy-phenol and 1-(3,4-Dimethoxy-phenyl)-ethanol, reacted faster than the corresponding α-carbonyl compounds with both reacting much faster than the aromatic compounds, with simple alkyl substituents. A new reaction mechanism for α-hydroxyl compounds is proposed, in which benzyl carbocation formation is followed by nucleophilic addition of hydrogen peroxide. Unlike the mechanisms proposed in the past, no evidence of aromatic hydroxylation via perhydronium ion was observed. The reactivities were very pH dependent, in that higher reactivity was associated with lower pH. Decreasing pH further increased the amount of condensation products identified, such that condensation was competitive with degradation. These condensation reactions were also present under the Caro's acid bleaching conditions at pH below 2. However, under all conditions the reactivity of acidic peroxide was found to be much less than that of peroxymonosulfuric acid.

Fragmentation mechanism of the phenylcoumaran-type lignin model compound by ToF-SIMS

Holzforschung ◽  
2013 ◽  
Vol 67 (4) ◽  
pp. 365-370 ◽  
Author(s):  
Yasuyuki Matsushita ◽  
Kousuke Ioka ◽  
Kaori Saito ◽  
Ruka Takama ◽  
Dan Aoki ◽  
...  
Keyword(s):  
Model Compound ◽  
Furan Ring ◽  
Secondary Ion Mass Spectrometry ◽  
Model Compounds ◽  
Lignin Model Compound ◽  
Tof Sims ◽  
Secondary Ions ◽  
Lignin Model ◽  
The Common ◽  
Secondary Ion

Abstract The experiments with model compounds revealed that time-of-flight secondary ion mass spectrometry (ToF-SIMS) is able to split the common interunit linkages of lignin, except the 5-5 linkage. In a previous study, ToF-SIMS produced characteristic secondary ions with m/z 137 and 151 (C6-C1 fragments) from the phenylcoumaran-type lignin model compound, the benzofuran ring of which has a β-5 linkage and an α-O-4 linkage. However, it is still unclear whether the fragments are from ring A with the free phenolic OH as a result of the sole cleavage of the α-O-4 link by opening the furan ring or from ring B as a result of the β-5 cleavage. In this study, the phenylcoumaran-type lignin model compound and its deuterium- and/or 13C-labeled analogues were synthesized and analyzed by ToF-SIMS. It could be clarified that the β-5 linkage is not cleaved by ToF-SIMS.

Three-dimensional composite of Co3O4 nanoparticles and nitrogen-doped reduced graphene oxide for lignin model compound oxidation

2018 ◽  
Vol 42 (13) ◽  
pp. 11117-11123 ◽  
Author(s):  
Jiali Zhang ◽  
Fangwei Zhang ◽  
Shouwu Guo ◽  
Jingyan Zhang
Keyword(s):  
Graphene Oxide ◽  
Reduced Graphene Oxide ◽  
Model Compound ◽  
Three Dimensional ◽  
Co3o4 Nanoparticles ◽  
Model Compounds ◽  
Lignin Model Compound ◽  
Reduced Graphene ◽  
Lignin Model ◽  
3D Composite

3D composite of Co3O4 nanoparticles and N-doped reduced graphene oxide can effectively catalyze the oxidation of lignin model compounds.

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