N-Alkylations of chitosanpromoted with sodium hydrogen carbonate under aqueous conditions
N-Alkylations of chitosanpromoted with sodium hydrogen carbonate under aqueous conditions
复制标题
碳酸氢钠在水溶液条件下促进壳聚糖的 N-烷基化
DOI：
10.1016/j.ijbiomac.2011.12.004
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发表时间：
2012
影响因子：
8.2
通讯作者：
Isogai A
中科院分区：
文献类型：
--
作者：
Kurita Y;Isogai A
在NaHCO3存在下，壳聚糖与溴乙酸、溴苄、2-溴乙醇和一氯乙酸等4种卤代烃反应，得到了壳聚糖的最佳反应条件。通过FT-IR、NMR、SEC-MALLS和元素分析研究了反应产物的化学结构、取代度和聚合度。该方法将烷基选择性地引入到壳聚糖的C2-氨基上，N-烷基壳聚糖的产率大于90%。N-羧甲基壳聚糖（N-CMCh）和N-苄基壳聚糖（N-BnCh）的取代度分别高达200%和164%，N，N-二羧甲基壳聚糖和N，N-二苄基壳聚糖的收率较高。N-CMCh的聚合度（DP）在反应过程中降低。加入的一溴乙酸的量越大，N-CMCh的DP越低。
Chitosan was reacted with four alkyl halides, monobromoacetic acid, benzyl bromide, 2-bromoethanol, and monochloroacetic acid, in the presence of NaHCO3in water. Chemical structures, degrees of substitution, and degrees of polymerization of reaction products were studied by FT-IR, NMR, SEC-MALLS, and elementary analyses. All alkyl groups were introduced selectively into the C2-amine groups of chitosan, and the yields of the N-alkyl chitosans were >90% by this method. N-Carboxymethyl chitosan (N-CMCh) and N-benzyl chitosan (N-BnCh) with high degrees of substitution (DS) up to 200% and 164% of the C2-amine groups, respectively, were obtained; N,N-dicarboxymethyl and N,N-dibenzyl chitosans were obtained in high yields. Degrees of polymerization (DP) of N-CMCh decreased during the reaction. The greater the amount of monobromoacetic acid added, the lower the DP of N-CMCh.