TY - JOUR

T1 - Synthesis of N-(1,2-dicarboxyethyl)chitosan

AU - Veretennikova, E.

AU - Koryakova, O.

AU - Mekhaev, A.

AU - Bratskaya, S.

AU - Pestov, A.

N1 - This work was financially supported by the Ministry of Education and Science of the Russian Federation in the framework of state assignments of the I. Ya. Postovsky Institute of Organic Synthesis (Ural Branch of the Russian Academy of Sciences) for 2023 (state registration No. AAAA-A19-119011790132-7) and Institute of Chemistry (Far East Branch of the Russian Academy of Sciences) for 2023 (FWFN (205)-2022-0002) in part of problem stating and discussion of the sorption properties of the derivatives. The synthesis and analysis of the compositions and structures of the derivatives were performed in the framework of the state assignment of I. Ya. Postovsky Institute of Organic Synthesis (Ural Branch of the Russian Academy of Sciences) using the equipment of the Center for Collective Use “Spectroscopy and Analysis of Organic Compounds.”

PY - 2023/12/1

Y1 - 2023/12/1

N2 - In order to prepare new ion-exchange materials, we proposed two methods for the synthesis of N-(1,2-dicarboxyethyl)chitosan from chitosan via polymer-analogous transformations: by nucleophilic addition—elimination with dimethyl ester of 2-oxosuccinic acid followed by reduction with sodium borohydride and by nucleophilic substitution with 2-bromosuccinic acid under the “synthesis in gel” conditions. When chitosan is treated with the 2-oxosuccinic acid derivatives, cross-linking of the polymer with the formation of amide functional groups occurs along with functionalization and leads to insoluble products. When sodium 2-bromosuccinate was used, water-soluble N-(1,2-dicarboxyethyl)-chitosan with the degree of functionalization up to 0.35 was synthesized. The ion-exchange properties were studied for the polymer additionally crosslinked with epichlorohydrin. The total static exchange capacity with respect to an equimolar mixture of CuII, NiII, CoII, and ZnII ions in an ammonium acetate buffer solution at pH 6.5 was 2 mmol g−1. The degree of extraction of the metal ions decreases in the series CuII (47%) > NiII (30%) > > ZnII (13%) > CoII (10%).

AB - In order to prepare new ion-exchange materials, we proposed two methods for the synthesis of N-(1,2-dicarboxyethyl)chitosan from chitosan via polymer-analogous transformations: by nucleophilic addition—elimination with dimethyl ester of 2-oxosuccinic acid followed by reduction with sodium borohydride and by nucleophilic substitution with 2-bromosuccinic acid under the “synthesis in gel” conditions. When chitosan is treated with the 2-oxosuccinic acid derivatives, cross-linking of the polymer with the formation of amide functional groups occurs along with functionalization and leads to insoluble products. When sodium 2-bromosuccinate was used, water-soluble N-(1,2-dicarboxyethyl)-chitosan with the degree of functionalization up to 0.35 was synthesized. The ion-exchange properties were studied for the polymer additionally crosslinked with epichlorohydrin. The total static exchange capacity with respect to an equimolar mixture of CuII, NiII, CoII, and ZnII ions in an ammonium acetate buffer solution at pH 6.5 was 2 mmol g−1. The degree of extraction of the metal ions decreases in the series CuII (47%) > NiII (30%) > > ZnII (13%) > CoII (10%).

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U2 - 10.1007/s11172-023-4110-9

DO - 10.1007/s11172-023-4110-9

M3 - Article

VL - 72

SP - 2987

EP - 2993

JO - Russian Chemical Bulletin

JF - Russian Chemical Bulletin

SN - 1066-5285

IS - 12

ER -