scholarly journals Bond Structures between Wood Components and Citric Acid in Wood-Based Molding

Polymers ◽  
2020 ◽  
Vol 13 (1) ◽  
pp. 58
Author(s):  
Daisuke Ando ◽  
Kenji Umemura
Keyword(s):  
Citric Acid ◽  
Chemical Bonding ◽  
Quantum Coherence ◽  
Japanese Cedar ◽  
Wood Adhesive ◽  
Hydroxyl Groups ◽  
Nmr Analysis ◽  
Correlation Peak ◽  
Primary Hydroxyl ◽  
Molding Condition

Citric acid-based wood adhesive is considered a chemical-bonding wood adhesive. However, the detailed structures of the bonds between wood components and citric acid remain unknown. Here, we examine the chemical bonding structures between citric acid and wood by heteronuclear single quantum coherence-nuclear magnetic resonance (HSQC-NMR) analysis of wood-based molding using Japanese cedar (Cryptomeria japonica) and citric acid. In the HSQC-NMR spectrum of the wood molding, some esterified C/H correlation peaks appeared. The primary hydroxyl groups of polysaccharides, such as cellulose and galactoglucomannan, and the primary hydroxyl groups of the β-O-4 and β-5 substructures in lignin were found to be esterified with citric acid. In contrast, the secondary hydroxyl groups, except for xylan, barely reacted because of the steric hindrance. Additionally, the C/H correlation peak volumes of the reducing ends of mannan and xylan in the anomeric region increased after molding. It was clarified that the glycosidic bonds in the hemicelluloses were cleaved under the acidic molding condition with citric acid. The HSQC-NMR analysis revealed that the esterification of hemicellulose and lignin, and degradation of hemicellulose, proceeded under the molding condition. These results will promote understanding of the adhesive mechanism of citric acid-based wood adhesive and of the properties of the molding.

scholarly journals Chemical Structures of Adhesive and Interphase Parts in Sucrose/Citric Acid Type Adhesive Wood-Based Molding Derived from Japanese Cedar (Cryptomeria japonica)

Polymers ◽  
2021 ◽  
Vol 13 (23) ◽  
pp. 4224
Author(s):  
Daisuke Ando ◽  
Kenji Umemura
Keyword(s):  
Citric Acid ◽  
Quantum Coherence ◽  
Japanese Cedar ◽  
Wood Adhesive ◽  
Hydroxyl Groups ◽  
Molding Process ◽  
Chemical Structures ◽  
Glycosidic Bonds ◽  
Acid Type ◽  
Adhesive Effect

In sucrose/citric acid based wood adhesive, the detailed bonding mechanism has still been unknown. Here, we investigated the detailed chemical structures of this adhesive wood (Japanese cedar)-based molding by using heteronuclear single quantum coherence–nuclear magnetic resonance (HSQC-NMR). NMR peaks associated with the furan-type structure appeared, suggesting that the furan compound was formed from sucrose and converted to a furan polymer during the adhesive process and that some of the furan structures in the polymers were ester-bonded with citric acid. The secondary forces between the furan polymers and wood components were thought to contribute to the adhesive effect. In our analysis of the interphase structure, primary hydroxyl groups of both polysaccharides and of lignin substructures were found to be esterified with citric acid. Additionally, some of the glycosidic bonds in polysaccharides were cleaved during the acidic condition produced by citric acid. The above results provided evidence of the polymerization of sucrose-derived 5-HMF, the esterification of wood components, and the degradation of polysaccharides during the molding process. Citric acid functioned as a clamp between the obtained furan polymer and the wood components. The sucrose/citric acid based wood adhesive can be defined as a hybrid-type wood adhesive, involving both secondary forces and chemical bonding interactions.

scholarly journals Structural Characterization of a Polysaccharide from Gastrodia elata and Its Bioactivity on Gut Microbiota

Molecules ◽  
2021 ◽  
Vol 26 (15) ◽  
pp. 4443
Author(s):  
Jiangyan Huo ◽  
Min Lei ◽  
Feifei Li ◽  
Jinjun Hou ◽  
Zijia Zhang ◽  
...  
Keyword(s):  
Molecular Weight ◽  
Citric Acid ◽  
Gut Microbiota ◽  
Structural Characterization ◽  
Hot Water ◽  
Nmr Analysis ◽  
Gastrodia Elata ◽  
Hot Water Extraction ◽  
Hydroxybenzyl Alcohol

A novel homogeneous polysaccharide named GEP-1 was isolated and purified from Gastrodia elata (G. elata) by hot-water extraction, ethanol precipitation, and membrane separator. GEP-1, which has a molecular weight of 20.1 kDa, contains a polysaccharide framework comprised of only glucose. Methylation and NMR analysis showed that GEP-1 contained 1,3,6-linked-α-Glcp, 1,4-linked-α-Glcp, 1,4-linked-β-Glcp and 1,4,6-linked-α-Glcp. Interestingly, GEP-1 contained citric acid and repeating p-hydroxybenzyl alcohol as one branch. Furthermore, a bioactivity test showed that GEP-1 could significantly promote the growth of Akkermansia muciniphila (A. muciniphila) and Lacticaseibacillus paracasei (L.paracasei) strains. These results implied that GEP-1 might be useful for human by modulating gut microbiota.

scholarly journals Study of the Reactivity of Lignin Model Compounds to Fluorobenzylation Using 13C and 19F NMR: Application to Lignin Phenolic Hydroxyl Group Quantification by 19F NMR

Molecules ◽  
2020 ◽  
Vol 25 (14) ◽  
pp. 3211
Author(s):  
Esakkiammal Sudha Esakkimuthu ◽  
Nathalie Marlin ◽  
Marie-Christine Brochier-Salon ◽  
Gérard Mortha
Keyword(s):  
Reaction Medium ◽  
19F Nmr ◽  
Hydroxyl Group ◽  
Hydroxyl Groups ◽  
Nmr Analysis ◽  
Model Compounds ◽  
Lignin Model Compounds ◽  
Wide Range ◽  
Lignin Model ◽  
13C And 19F Nmr

Lignin is an aromatic biopolymer derived from lignocellulosic biomass. Providing a comprehensive structural analysis of lignin is the primary motivation for the quantification of various functional groups, with a view to valorizing lignin in a wide range of applications. This study investigated the lignin fluorobenzylation reaction and performed a subsequent 19F-NMR analysis to quantify hydroxyl groups, based on a work developed two decades ago by Barrelle et al. The objectives were to check the assignments proposed in this previous study and to examine the reactivity of various types of lignin hydroxyls with the derivatization agent. Selected lignin model compounds containing phenolic and aliphatic hydroxyls were subjected to the fluorobenzylation reaction, and the obtained reaction medium was analyzed by 13C and 19F NMR spectroscopy. The model compound results showed that phenolic hydroxyls were totally derivatized, whereas aliphatic hydroxyls underwent minimal conversion. They also confirmed that 19F NMR chemical shifts from −115 ppm to −117.3 ppm corresponded to phenolic groups. Then, a 19F NMR analysis was successfully applied to Organosolv commercial lignin after fluorobenzylation in order to quantify its phenolic group content; the values were found to be in the range of the reported values using other analytical techniques after lignin acetylation.

Synthesis and characterization of α-butyl-ω-{3-[(2,2- dihydroxymethyl)-propionyloxy]}propyl polydimethyl siloxane

e-Polymers ◽  
2010 ◽  
Vol 10 (1) ◽  
Author(s):  
Meng Zhang ◽  
Yuanjuan Wu ◽  
Qingsi Zhang ◽  
Tianduo Li
Keyword(s):  
Ring Opening ◽  
Ring Opening Polymerization ◽  
Synthesis And Characterization ◽  
Hydroxyl Groups ◽  
Single Chain ◽  
Polydimethyl Siloxane ◽  
Primary Hydroxyl ◽  
Anionic Ring

AbstractA novel polydimethylsiloxane containing two primary hydroxyl groups at one single chain end was synthesized by five-step reactions which included esterification, hydroxyl protection, anionic ring-opening polymerization, hydrosilylation and deprotection. The prepared compounds in each step were characterized. The results showed that at each step synthesis was successfully carried out and objective products could be achieved.

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