Dependence of chiral recognition on the degree of substitution of cellulose benzoate

Toga, Yuzo; Hioki, Kenji; Namikoshi, Hajime; Shibata, Tsugumichi

doi:10.1023/b:cell.0000014764.78168.88

Cited by 10 publications

(3 citation statements)

References 9 publications

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“…Spinning was subsequently performed using the nonsolvent-induced phase separation method. 31,32 The ester solution in the syringe was injected in water through the needle at a constant rate. The fibrous cellulose ester solution (diameter 0.5 mm) gradually phase separated, leading to the regeneration of a solid filament.…”

Section: Methodsmentioning

confidence: 99%

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Mechanism of sodium-hypochlorite-induced degradation of cellulose acetate and the enhancement of its degradation resistance by chemical modification

Hashizume

Okamoto

Nagai

et al. 2022

Textile Research Journal

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Cellulose acetate, when used in the form of hollow fibers in the ultrafiltration stage of water treatment, is occasionally treated with sodium hypochlorite to remove organic particles such as humic acids. However, prolonged use of sodium hypochlorite reduces the strength of the membrane and facilitates its breakage. The present study was designed to reveal the degradation mechanism of cellulose acetate caused by aqueous sodium hypochlorite and to improve its resistance to this chemical. Filaments of cellulose acetate, prepared using a nonsolvent-induced phase separation method, were exposed to 2000 ppm aqueous sodium hypochlorite at 25°C for 13 days to allow for evaluation of the changes in their tensile strength, elongation at break, molecular weight, degree of substitution, and chemical structure. The tensile strength, elongation at break, and molecular weight decreased as the duration of exposure to sodium hypochlorite increased. No significant changes in the degree of substitution were observed by one-dimensional hydrogen 1 nuclear magnetic resonance, and cleavages of both glycoside bonds and carbon–carbon bonds were detected by two-dimensional nuclear magnetic resonance, revealing that base-catalyzed hydrolysis of ester groups did not play an important role in degradation. The chemical modifications of the cellulose esters, such as the introduction of pentanoyl, stearoyl, and benzoyl groups, were studied in accordance with the degradation mechanism, and cellulose esters with bulky substituents such as benzoyl groups were found to exhibit improved chlorine resistance. Perbenzoylated cellulose, which exhibited high resistance to sodium hypochlorite, is considered to be a potential membrane material for the filtration of foulant-rich raw water.

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Section: Methodsmentioning

confidence: 99%

“…Benzoylation of cellulose was performed according to previously reported methods. 30 The typical synthesis method is described henceforth. The cellulose used in this study (rayon), which contained 60 wt.% water and 40 wt.% cellulose, was used without drying.…”

Section: Preparation Of Cellulose Estersmentioning

confidence: 99%

Mechanism of sodium-hypochlorite-induced degradation of cellulose acetate and the enhancement of its degradation resistance by chemical modification

Hashizume

Okamoto

Nagai

et al. 2022

Textile Research Journal

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“…Actually, the type, quantity and distribution of substituents on cellulose derivatives have a significant impact on the helical structure and local polarity, and accordingly on the recognition abilities. Toga et al studied the chiral recognition ability of partially substituted cellulose benzoates with a degree of substitution (DS) from 2.1 to 2.8, which were prepared by aminolysis of cellulose tribenzoate with hydrazine in 1‐methyl‐2‐pyrrolidone, and indicated that some enantiomeric pairs were resolved only by partially substituted cellulose benzoates . Yuan and co‐workers also found that partially substituted cellulose derivatives, compared with fully substituted ones, showed good separation factors for some racemates, namely the chiral discrimination ability was not proportional to DS .…”

Section: Introductionmentioning

confidence: 99%

Homogeneous synthesis of partially substituted cellulose phenylcarbamates aiming at chiral recognition

Chen

Zhang

Feng

et al. 2015

Polymer International

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Homogeneous carbanilation of cellulose with nine kinds of substituted phenyl isocyanates, in which the substituents were varied from electron-donating to electron-withdrawing groups, was carried out in 1-allyl-3-methylimidazolium chloride (AmimCl) without any catalyst. The degree of substitution (DS) of cellulose phenylcarbamates in a range from 0 to 3 was readily controlled by altering reaction temperature, reaction time and molar ratio of phenyl isocyanate/anhydroglucose unit. Furthermore, the electronic effect of the substituents on the aromatic ring had a prominent impact on the reactivity of phenyl isocyanates. The phenyl isocyanates with stronger electron-withdrawing substituents exhibited a higher reactivity. A plot of DS and Hammett substituent constants exhibited linearity with a positive slope. Subsequently, four kinds of partially substituted cellulose phenylcarbamates with DS of 2.0 were synthesized successfully in AmimCl, and then employed as coated-type chiral stationary phases (CSPs) for high-performance liquid chromatography. The enantioseparation results demonstrated that these CSPs exhibited high chiral recognition abilities for some racemates. The substituents on the phenyl moieties had a considerable effect on the chiral recognition ability of cellulose phenylcarbamate-based CSPs.

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Ionic Liquids as Solvents for Homogeneous Derivatization of Cellulose: Challenges and Opportunities

Heinze

Gericke

2013

Production of Biofuels and Chemicals With Ionic Liquids

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Dependence of chiral recognition on the degree of substitution of cellulose benzoate

Cited by 10 publications

References 9 publications

Mechanism of sodium-hypochlorite-induced degradation of cellulose acetate and the enhancement of its degradation resistance by chemical modification

Mechanism of sodium-hypochlorite-induced degradation of cellulose acetate and the enhancement of its degradation resistance by chemical modification

Homogeneous synthesis of partially substituted cellulose phenylcarbamates aiming at chiral recognition

Ionic Liquids as Solvents for Homogeneous Derivatization of Cellulose: Challenges and Opportunities

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