Direct conversion of chitin into a N-containing furan derivative
Direct conversion of chitin into a N-containing furan derivative
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DOI：
10.1039/c3gc42436g
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发表时间：
2014-01-01
期刊：
影响因子：
9.8
通讯作者：
Yan, Ning
中科院分区：
文献类型：
--
作者：
Chen, Xi;Chew, Shu Ling;Yan, Ning
本文首次报道了甲壳素直接转化为含氮呋喃衍生物（3A 5AF）。在优化条件下，3A 5AF的产率可达7.5%，收率约为9.5%。以硼酸和碱性氯化物为添加剂，NMP为溶剂，甲壳素转化率可达50%。各种各样的其他化合物，包括左旋葡萄糖酮，4-（乙酰氨基）-1，3-苯丙氨酸，乙酸和几丁质-胡敏素，已被确定为副产物，基于此提出了一个合理的反应网络参与的过程。通过核磁共振研究和毒物测试的机理研究证实了在反应过程中形成硼络合物中间体，从而阐明了硼酸的促进作用。动力学研究表明，甲壳素结晶区的解聚是速率决定性的，因此在反应之前或反应期间，甲壳素结晶区中氢键的破坏是进一步提高反应产率的关键。
This paper describes the direct conversion of chitin into a nitrogen-containing (N-containing) furan derivative (3A5AF) for the first time. Under optimized conditions, the yield of 3A5AF reaches 7.5% with ca. 50% chitin conversion by using boric acid and alkaline chlorides as additives, and NMP as a solvent. A variety of other compounds, including levoglucosenone, 4-(acetylamino)-1,3-benzenediol, acetic acid and chitin-humins, have been identified as side products, based on which a plausible reaction network involved in the process is proposed. Mechanistic investigation by NMR studies and poison tests confirms the formation of a boron complex intermediate during the reaction, shedding light on the promotional effects of boric acid. Kinetic studies show that the depolymerization of the chitin crystalline region is rate-determining, and therefore disruption of the hydrogen bonding in the crystalline region of chitin, either before or during the reaction, is the key to further improving the reaction yields.