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

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: 7 February 2024

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.
- Decanedioic acid,
- N-hydroxysuccinimide,
- Collagen modification,
- Comprehensive applied chemistry experiment
1. [1]
2. [2]
3. [3]
4. [4]
5. [5]
6. [6]
  Zhang, M.; Wu, K., Li, G. Int. J. Biol. Macromol. 2011, 49, 847.
7. [7]
  Li, B.; Wang, J.; Ji, L.; Bai, T.; Zhang, Y.; Liu, D. Roy. Soc. Open Sci. 2021, 8, 201892.
8. [8]
9. [9]
  Rung, S.; Zhao, X.; Chu, C.; Yang, R.; Qu, Y.; Man, Y. Materials 2021, 14, 4660.
10. [10]
  Grabska-Zielinska, S.; Sionkowska, A.; Cravalho, A.; Monteiro, F. Materials 2021, 14, 1105.
11. [11]
  Kajiyama, T.; Kobayashi, H.; Taguchi, T.; Saito, H.; Tanaka, J. Mat. Sci. Eng. C-Mater. 2004, 24, 815.
12. [12]
  Taguchi, T.; Saito, H.; Aoki, H.; Uchida, Y.; Sakane, M.; Kobayashi, H.; Tanaka, J. Mat. Sci. Eng. C-Mater. 2006, 26, 9.
13. [13]
  Zhang, M.; Li, G. J. Aquat. Food Prod. Technol. 2014, 23, 44.
14. [14]
  Duan, L.; Liu, W.; Tian, Z.; Li, C.; Li, G. Int. J. Biol. Macromol. 2014, 69, 482.
15. [15]
  Shen, L.; Tian, Z.; Liu, W.; Li, G. Connect. Tissue Res. 2015, 56, 244.
16. [16]
  Zhuang, C.; Tao, F.; Cui, Y. Chem. Pap. 2016, 70 (4), 505.
17. [17]
  Warner, W. S.; Tenge, B. J.; Hungerford, J. M.; Honigs, D. E. Anal. Biochem. 1989, 176, 137.
18. [18]
1. [1]
  Sijiang Hu , Hongqiang Wang , Jiming Peng , Fenghua Zheng , Qichang Pan , Kui Liu , Qingyu Li . Ideological and Political Education Practice of the Comprehensive Applied Chemistry Laboratory for Emerging Engineering Education. University Chemistry, 2024, 39(2): 214-220. doi: 10.3866/PKU.DXHX202307019
2. [2]
  Yanglin Jiang , Mingqing Chen , Min Liang , Yige Yao , Yan Zhang , Peng Wang , Jianping Zhang . Experimental and Theoretical Investigations of Solvent Polarity Effect on ESIPT Mechanism in 4′-N,N-diethylamino-3-hydroxybenzoflavone. Acta Physico-Chimica Sinica, 2025, 41(2): 100012-. doi: 10.3866/PKU.WHXB202309027
3. [3]
  Jianfeng Yan , Yating Xiao , Xin Zuo , Caixia Lin , Yaofeng Yuan . Comprehensive Chemistry Experimental Design of Ferrocenylphenyl Derivatives. University Chemistry, 2024, 39(4): 329-337. doi: 10.3866/PKU.DXHX202310005
4. [4]
  Nuo Zhang , Xiaojun Sun , Hongmin Ma , Yan Li , Xiang Ren , Dan Wu , Chuannan Luo , Qin Wei . Construction and Practice of National Experimental Teaching Demonstration Center of Applied Chemistry. University Chemistry, 2024, 39(7): 116-120. doi: 10.12461/PKU.DXHX202405031
5. [5]
  Xiaofeng Xia , Jielian Zhu . Innovative Comprehensive Experimental Design: Synthesis of 6-Fluoro-N-benzoyl Tetrahydroquinoline. University Chemistry, 2024, 39(10): 344-352. doi: 10.12461/PKU.DXHX202405063
6. [6]
  Tingting Yu , Si Chen , Lianglong Sun , Tongtong Shi , Kai Sun , Xin Wang . Comprehensive Experimental Design for the Photochemical Synthesis, Analysis, and Characterization of Difluoropyrroles. University Chemistry, 2024, 39(11): 196-203. doi: 10.3866/PKU.DXHX202401022
7. [7]
  Yikai Wang , Xiaolin Jiang , Haoming Song , Nan Wei , Yifan Wang , Xinjun Xu , Cuihong Li , Hao Lu , Yahui Liu , Zhishan Bo . 氰基修饰的苝二酰亚胺衍生物作为膜厚不敏感型阴极界面材料用于高效有机太阳能电池. Acta Physico-Chimica Sinica, 2025, 41(3): 2406007-. doi: 10.3866/PKU.WHXB202406007
8. [8]
  Yang Chen , Peng Chen , Yuyang Song , Yuxue Jin , Song Wu . Application of Chemical Transformation Driven Impurity Separation in Experiments Teaching: A Novel Method for Purification of α-Fluorinated Mandelic Acid. University Chemistry, 2024, 39(6): 253-263. doi: 10.3866/PKU.DXHX202310077
9. [9]
  Xuejiao Wang , Suiying Dong , Kezhen Qi , Vadim Popkov , Xianglin Xiang . Photocatalytic CO₂ Reduction by Modified g-C₃N₄. Acta Physico-Chimica Sinica, 2024, 40(12): 2408005-. doi: 10.3866/PKU.WHXB202408005
10. [10]
  Junke LIU , Kungui ZHENG , Wenjing SUN , Gaoyang BAI , Guodong BAI , Zuwei YIN , Yao ZHOU , Juntao LI . Preparation of modified high-nickel layered cathode with LiAlO₂/cyclopolyacrylonitrile dual-functional coating. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1461-1473. doi: 10.11862/CJIC.20240189
11. [11]
  Feng Zheng , Ruxun Yuan , Xiaogang Wang . “Research-Oriented” Comprehensive Experimental Design in Polymer Chemistry: the Case of Polyimide Aerogels. University Chemistry, 2024, 39(10): 210-218. doi: 10.12461/PKU.DXHX202404027
12. [12]
  Qi Wang , Yicong Gao , Feng Lu , Quli Fan . Preparation and Performance Characterization of the Second Near-Infrared Phototheranostic Probe: A New Design and Teaching Practice of Polymer Chemistry Comprehensive Experiment. University Chemistry, 2024, 39(11): 342-349. doi: 10.12461/PKU.DXHX202404141
13. [13]
  Shengbiao Zheng , Liang Li , Nini Zhang , Ruimin Bao , Ruizhang Hu , Jing Tang . Metal-Organic Framework-Derived Materials Modified Electrode for Electrochemical Sensing of Tert-Butylhydroquinone: A Recommended Comprehensive Chemistry Experiment for Translating Research Results. University Chemistry, 2024, 39(7): 345-353. doi: 10.3866/PKU.DXHX202310096
14. [14]
  Bao Jia , Yunzhe Ke , Shiyue Sun , Dongxue Yu , Ying Liu , Shuaishuai Ding . Innovative Experimental Teaching for the Preparation and Modification of Conductive Organic Polymer Thin Films in Undergraduate Courses. University Chemistry, 2024, 39(10): 271-282. doi: 10.12461/PKU.DXHX202404121
15. [15]
  Haiyuan Wang , Shanshan Cheng , Hui Yang . Development and Exploration of the Ideological and Political Education Framework in Applied Chemistry Postgraduate Curriculum. University Chemistry, 2024, 39(6): 72-82. doi: 10.3866/PKU.DXHX202311020
16. [16]
  Peiqi Gao , Jiao Zheng , LiMiao Chen , Yi Zhang . Exploration of the Deep Integration Strategy between Innovation and Entrepreneurship Education and Applied Chemistry Major Courses. University Chemistry, 2024, 39(6): 214-219. doi: 10.3866/PKU.DXHX202310086
17. [17]
  Yinuo Wang , Siran Wang , Yilong Zhao , Dazhen Xu . Selective Synthesis of Diarylmethyl Anilines and Triarylmethanes via Multicomponent Reactions: Introduce a Comprehensive Experiment of Organic Chemistry. University Chemistry, 2024, 39(8): 324-330. doi: 10.3866/PKU.DXHX202401063
18. [18]
  Yihao Zhao , Jitian Rao , Jie Han . Synthesis and Photochromic Properties of 3,3-Diphenyl-3H-Naphthopyran: Design and Teaching Practice of a Comprehensive Organic Experiment. University Chemistry, 2024, 39(10): 149-155. doi: 10.3866/PKU.DXHX202402050
19. [19]
  Meijin Li , Xirong Fu , Xue Zheng , Yuhan Liu , Bao Li . The Marvel of NAD⁺: Nicotinamide Adenine Dinucleotide. University Chemistry, 2024, 39(9): 35-39. doi: 10.12461/PKU.DXHX202401027
20. [20]
  Tao Jiang , Yuting Wang , Lüjin Gao , Yi Zou , Bowen Zhu , Li Chen , Xianzeng Li . Experimental Design for the Preparation of Composite Solid Electrolytes for Application in All-Solid-State Batteries: Exploration of Comprehensive Chemistry Laboratory Teaching. University Chemistry, 2024, 39(2): 371-378. doi: 10.3866/PKU.DXHX202308057

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(93)
HTML views(16)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142