癸二酸-<i>N</i>-羟基琥珀酰亚胺酯的合成及应用——应用化学综合实验教学改革探究

引用本文: 沈里瑞, 刘坤, 杨颖, 李冬婉, 常文贵. 癸二酸-N-羟基琥珀酰亚胺酯的合成及应用——应用化学综合实验教学改革探究[J]. 大学化学, 2024, 39(8): 212-220. doi: 10.3866/PKU.DXHX202312035 shu

Citation: Lirui Shen, Kun Liu, Ying Yang, Dongwan Li, Wengui Chang. Synthesis and Application of Decanedioic Acid-N-Hydroxysuccinimide Ester: Exploration of Teaching Reform in Comprehensive Applied Chemistry Experiment[J]. University Chemistry, 2024, 39(8): 212-220. doi: 10.3866/PKU.DXHX202312035 shu

癸二酸-N-羟基琥珀酰亚胺酯的合成及应用——应用化学综合实验教学改革探究

沈里瑞 ^1, ,
刘坤 ^1, ,
杨颖 ^1, ,
李冬婉 ^2, ,
常文贵 ^1,

1.
皖西学院材料与化工学院, 安徽六安 237012;
2.
中共安徽省委党校, 合肥 230022
基金项目:
安徽省高校自然科学重点项目(2023AH052644)；皖西学院线上课程建设项目(wxxy2022045)；皖西学院高层次人才启动资金项目(WGKQ2021040)；安徽省高等学校省级质量工程项目(2021zygzts067,2022zygzts123)

摘要: 介绍了一个关于活性酯基交联剂的合成及应用的应用化学综合实验。内容包括：癸二酸-N-羟基琥珀酰亚胺酯(NHS-DA)的制备，产物的结构的鉴定，以及在胶原热稳定性改善方面的应用。首先，以癸二酸、N-羟基琥珀酰亚胺作为原料，碳化二亚胺作为脱水剂，制得癸二酸-N-羟基琥珀酰亚胺酯，产率约为85%。通过核磁共振波谱和红外光谱分析对合成产物的结构进行了鉴定，结果表明为目标产物——NHS-DA。其次，将NHS-DA应用于胶原海绵的改性，差式扫描量热分析表明NHS-DA可以改善胶原的热稳定性，促进实验产物的应用。整体实验反应条件温和、速率快、产率高，废弃物丙酮可回收利用，涉及多种先进实验仪器的使用，能够紧密结合理论所学知识、科学前沿和应用需求，有助于培养学生理论结合实际应用的能力，激发学生的创新性思维且拓展学生的科学视野。

关键词:

English

Synthesis and Application of Decanedioic Acid-N-Hydroxysuccinimide Ester: Exploration of Teaching Reform in Comprehensive Applied Chemistry Experiment

1.
Materials and Chemical Engineering College, West Anhui University, Lu' An 237012, Anhui Province, China;
2.
Party School of Anhui Provincial Committee of C. P. C, Hefei 230022, China
Received Date: 10 December 2023
Revised Date: 07 February 2024
Available Online: 29 February 2024

Abstract: This paper introduces a comprehensive applied chemistry experiment on the synthesis and application of an active ester cross-linking agent. The experiment involves the preparation of decanedioic acid-N-hydroxysuccinimide ester (NHS-DA), identification of its structure, and its application in improving collagen thermal stability. Initially, NHS-DA is synthesized from decanedioic acid, and N-hydroxysuccinimide using 1-(3-dimethylaminopropyl)-3-ethylcarbondiimide hydrochloride as a condensing agent, achieving a yield of approximately 85%. The product’s structure is confirmed through nuclear magnetic resonance and Fourier-transform infrared spectroscopy, indicating the successful synthesis of high-purity NHS-DA. Subsequently, NHS-DA is applied to cross-link collagen sponge, with differential scanning calorimetry demonstrating enhanced thermal stability, thus promoting its application potential. The experiment is characterized by mild conditions, rapid reaction rates, high yields, and the recyclability of waste acetone, incorporating the use of various advanced instruments. It effectively integrates theoretical knowledge with practical application, fostering students' innovative thinking and expanding their scientific perspectives.

Key words:

Decanedioic acid
/ N-hydroxysuccinimide
/ Collagen modification
/ Comprehensive applied chemistry experiment

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沈阳化工大学材料科学与工程学院沈阳 110142

癸二酸-N-羟基琥珀酰亚胺酯的合成及应用——应用化学综合实验教学改革探究

English

Synthesis and Application of Decanedioic Acid-N-Hydroxysuccinimide Ester: Exploration of Teaching Reform in Comprehensive Applied Chemistry Experiment

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通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

癸二酸-N-羟基琥珀酰亚胺酯的合成及应用——应用化学综合实验教学改革探究

English

Synthesis and Application of Decanedioic Acid-N-Hydroxysuccinimide Ester: Exploration of Teaching Reform in Comprehensive Applied Chemistry Experiment

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

CCS Chemistry：颜徐州、鲍哲南： 你的皮肤可能是一片SPMs

CCS Chemistry：工作高效不疲劳，只须让催化剂动起来

CCS Chemistry：静电组装导向聚合- 聚电解质纳米凝胶量化制备新策略

CCS Chemistry：金黄色葡萄球菌醛基脱氢酶是如何识别特异性底物的？

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