Predominant formation of aromatic aldehyde and acid from a dimeric β-O-4-type lignin model compound under hydrogen peroxide bleaching conditions with high pH levels

Posoknistakul, Pattaraporn; Akiyama, Takuya; Yokoyama, Tomoya; Matsumoto, Yuji

doi:10.1007/s10086-017-1609-4

Cited by 5 publications

(17 citation statements)

References 31 publications

(58 reference statements)

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“…The synthesis of compounds 1E and 1T and their separation were described in our previous reports [11][12][13]. The structures and purities were confirmed by nuclear magnetic resonance spectroscopy ( 1 H-NMR and 13 C-NMR, JNM-A500, JEOL Ltd., Tokyo, Japan).…”

Section: Methodsmentioning

confidence: 99%

“…A portion of the reaction solution was withdrawn at prescribed reaction times to quantify the surviving compound 1E or 1T and to measure the pH. The detailed workup procedures for quantification were the same as those described in our previous reports [11][12][13] except for neutralizing the acidic reaction solution with sodium hydrogen carbonate.…”

Section: Oxidation In Hypochlorite Systemsmentioning

confidence: 99%

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Stereo-preference in the degradation of the erythro and threo isomers of β-O-4-type lignin model compounds in oxidation processes III: in the reaction with chlorine- and manganese-based oxidants

et al. 2018

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We examined which isomer, the erythro or threo, of a non-phenolic β-O-4-type lignin model compound is stereo-preferentially oxidized in hypochlorite, chlorite, manganese dioxide, or permanganate systems. No clear stereo-preference was observed in the hypochlorite or chlorite systems at alkaline, neutral, or acidic pH except for a slight threo stereo-preference that appeared after the step-wise addition of the oxidizing reagent had been terminated in the neutral or acidic chlorite systems. A clear threo stereo-preference was observed in the manganese dioxide or permanganate systems.

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Section: Methodsmentioning

confidence: 99%

Section: Oxidation In Hypochlorite Systemsmentioning

confidence: 99%

Stereo-preference in the degradation of the erythro and threo isomers of β-O-4-type lignin model compounds in oxidation processes III: in the reaction with chlorine- and manganese-based oxidants

et al. 2018

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“…1). Vald and Vacid were quantified in our subsequent report 29) . The maximum total yield of these compounds in alkaline H2O2 bleaching processes at high pH levels…”

Section: Introductionmentioning

confidence: 99%

“…In this paper, we optimized the reaction conditions of the alkaline H2O2 bleaching treatments to degrade VG more completely (higher PD) and afford Vald and Vacid in larger amounts (higher TY), maintaining or further improving CR (CR=TY/PD×100%) when compared with previous results 29) . The optimization parameters were the concentration of sodium hydroxide (NaOH), addition amounts of iron (as FeCl3), magnesium (as MgCl2), or copper (as CuCl2), manner of H2O2 addition, and addition amount of D-mannitol.…”

Section: Introductionmentioning

confidence: 99%

Optimization of Alkaline Hydrogen Peroxide Treatment of Lignin Model Compound at High pH Levels for Producing Aromatic Aldehyde and Acid as Fine Chemicals

Sakai,

Katsumata,

Yokoyama

2022

Lignin

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A non-phenolic β-O-4-type lignin model compound, veratrylglycerol-β-guaiacyl ether (VG), was treated with H 2 O 2 at high pH levels in our previous study. Veratraldehyde (Vald) and veratric acid (Vacid), which are non-phenolic analogues of the most common lignin-based fine chemicals, vanillin and vanillic acid, respectively, were obtained with a high total yield of 77% based on the amount of degraded VG, although only 22% of VG was degraded and hence the total yield of Vald and Vacid was only 17% based on the initial amount of VG. This study optimized the alkaline H 2 O 2 treatment to enhance the degradation of VG and yields of Vald and Vacid. The degradation of VG and total yield of Vald and Vacid were enhanced from 22% to 54% and from 17% to 39%, respectively, by optimizing the conditions as follows: 1.96 mmol of H 2 O 2 were added stepwise 400 times with an interval of 15 s in a reaction solution containing 1.0 mmol/L VG, 3.0 mol/L NaOH, 1.08 mmol/L FeCl3, and 3.24 mmol/L mannitol at 90℃. Doubling the reaction period and employing twice the amount of H 2 O 2 (3.92 mmol) in the absence of mannitol further enhanced the degradation of VG to 61% and the total yield to 44%.

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“…Lignin model compounds have been used in the study of pulp bleaching. Posoknistakul [19] synthesized veratrylglycerol-β-guaiacyl ether (VG), a non-phenolic lignin model compound with a β-O-4 bond. The reactions of VG during hydrogen peroxide bleaching and alkaline oxygen bleaching systems have been studied.…”

mentioning

confidence: 99%

Difference in adsorbable organic halogen formation between phenolic and non-phenolic lignin model compounds in chlorine dioxide bleaching

Shi

Zhang

et al. 2019

R. Soc. open sci.

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Adsorbable organic halogen (AOX) is generally formed by the reaction of residual lignin in pulps with chlorine dioxide during bleaching. Lignin has a complex structure. Different functional groups and bonds are present in lignin structures. Phenolic hydroxyl is one of the important functional groups in lignin, and it significantly influences the chemical properties and reactivity. To study the effect of phenolic hydroxyl on AOX formation, vanillyl alcohol (VA) was selected as the phenolic lignin model compound, and veratryl alcohol (VE) was selected as the non-phenolic lignin model compound in this study. The kinetics of AOX formation by the reaction of VA or VE with chlorine dioxide was studied. The effects of pH, chlorine dioxide, lignin model compound concentration and reaction temperature on AOX formation are discussed. The activation energies of the reaction of VA and VE with chlorine dioxide are 16 242.47 J mol−1 and 281.34 J mol−1, respectively. Thus, we found that the non-phenolic lignin can react with chlorine dioxide to form AOX more easily than phenolic lignin.

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Predominant formation of aromatic aldehyde and acid from a dimeric β-O-4-type lignin model compound under hydrogen peroxide bleaching conditions with high pH levels

Cited by 5 publications

References 31 publications

Stereo-preference in the degradation of the erythro and threo isomers of β-O-4-type lignin model compounds in oxidation processes III: in the reaction with chlorine- and manganese-based oxidants

Stereo-preference in the degradation of the erythro and threo isomers of β-O-4-type lignin model compounds in oxidation processes III: in the reaction with chlorine- and manganese-based oxidants

Optimization of Alkaline Hydrogen Peroxide Treatment of Lignin Model Compound at High pH Levels for Producing Aromatic Aldehyde and Acid as Fine Chemicals

Difference in adsorbable organic halogen formation between phenolic and non-phenolic lignin model compounds in chlorine dioxide bleaching

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