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]
  Ruihu Wang , Aidang Lu . 新型铬(VI)检测试纸的制备及应用——介绍一个应用化学综合实验. University Chemistry, 2025, 40(8): 284-290. doi: 10.12461/PKU.DXHX202410102
3. [3]
  Caixia Lin , Ting Liu , Zhaojiang Shi , Hong Yan , Keyin Ye , Yaofeng Yuan . Innovative Experiment of Electrochemical Dearomative Spirocyclization of N-Acyl Sulfonamides. University Chemistry, 2025, 40(4): 359-366. doi: 10.12461/PKU.DXHX202406107
4. [4]
  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): 2309027-0. doi: 10.3866/PKU.WHXB202309027
5. [5]
  Xiaoyang Li , Xiaowei Huang , Yimeng Zhang , Huan Liu , Shao Jin , Junpeng Zhuang . Comprehensive Chemical Experiments on the Synthesis of 1,3-Dibromo-5,5-Dimethylhydantoin and Its Application as a Brominating Reagent. University Chemistry, 2025, 40(7): 286-293. doi: 10.12461/PKU.DXHX202408035
6. [6]
  Xiaogang Liu , Mengyu Chen , Yanyan Li , Xiantao Ma . Experimental Reform in Applied Chemistry for Cultivating Innovative Competence: A Case Study of Catalytic Hydrogen Production from Liquid Formaldehyde Reforming at Room Temperature. University Chemistry, 2025, 40(7): 300-307. doi: 10.12461/PKU.DXHX202408007
7. [7]
  Jinrong Bao , Jinglin Zhang , Wenxian Li , Xiaowei Zhu . 苯甲酸稀土配合物的制备及性能表征——基于应用化学专业人才培养的综合化学实验案例分析. University Chemistry, 2025, 40(8): 218-224. doi: 10.12461/PKU.DXHX202409142
8. [8]
  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
9. [9]
  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
10. [10]
  Shuyong Zhang , Zhong Wei , Gang Ni , Chunyan Sun , Jianping Li , Hualong Xu , Xijiang Han , Qiue Cao , Yanguang Wang , Yi Yang , Yuqiang Ding , Wenqing Zhang . Suggestions on Theoretical and Experimental Teaching Contents of Applied Chemistry Majors in Universities. University Chemistry, 2025, 40(5): 1-8. doi: 10.12461/PKU.DXHX202404002
11. [11]
  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
12. [12]
  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
13. [13]
  Wenyuan Hu , Jichuan Huo , Guoqing Zhong , Binyao Liu , Qiying Jiang , Qiulin Deng , Dingming Yang , Tinghong Zhang , Hongbo Li , Pingping Zhu . Construction and Exploration of an Innovative Talent Training Practical Curriculum System for Applied Chemistry at Local Universities. University Chemistry, 2025, 40(7): 55-61. doi: 10.12461/PKU.DXHX202409075
14. [14]
  Yikai Wang , Xiaolin Jiang , Haoming Song , Nan Wei , Yifan Wang , Xinjun Xu , Cuihong Li , Hao Lu , Yahui Liu , Zhishan Bo . Thickness-Insensitive, Cyano-Modified Perylene Diimide Derivative as a Cathode Interlayer Material for High-Efficiency Organic Solar Cells. Acta Physico-Chimica Sinica, 2025, 41(3): 2406007-0. doi: 10.3866/PKU.WHXB202406007
15. [15]
  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
16. [16]
  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
17. [17]
  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
18. [18]
  Yang Li , Jiachen Li , Daidi Fan . 二硫化钼纳米片的制备及其纳米酶性能探究——介绍一个大学化学综合实验. University Chemistry, 2025, 40(8): 233-240. doi: 10.12461/PKU.DXHX202410016
19. [19]
  Shuhui Li , Rongxiuyuan Huang , Yingming Pan . Electrochemical Synthesis of 2,5-Diphenyl-1,3,4-Oxadiazole: A Recommended Comprehensive Organic Chemistry Experiment. University Chemistry, 2025, 40(5): 357-365. doi: 10.12461/PKU.DXHX202407028
20. [20]
  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

Get Citation

PDF

XML

Metrics

PDF Downloads(1)
Abstract views(269)
HTML views(27)

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