Citation: Ruqi Wang, Peixin Wang, Zhaoyu Wang, Ruijian Fang, Weiguang Zhao, Ying Guan. Example of Outcome-based Investigational Experiment and the Development of Innovation Capabilities: Primary Study on the Ultrasound-Assisted Fischer Esterification Reaction Conditions[J]. University Chemistry, ;2023, 38(10): 199-208. doi: 10.3866/PKU.DXHX202301027 shu

Example of Outcome-based Investigational Experiment and the Development of Innovation Capabilities: Primary Study on the Ultrasound-Assisted Fischer Esterification Reaction Conditions

College of Chemistry, Nankai University, Tianjin 300071, China

Corresponding author: Weiguang Zhao, Ying Guan,
Received Date: 26 January 2023
Revised Date: 19 April 2023

In the outcome-based teaching activities of investigational experiments and innovative capacity development, a three-stage teaching process is designed to enable students to experience the whole process of scientific research and develop research skills in the experimental learning process. The three stages are design, implementation, and conclusion of the program. This paper demonstrates the results of teaching activity based on an example of a student’s lab report written in the form of a published paper. To investigate the Fischer esterification reaction under ultrasonic assisted conditions, the report compares the catalytic efficiency of different catalysts for the reaction using the esterification synthesis reaction of ethyl benzoate as an example. The results indicate that acid-loaded montmorillonite K-10 catalysis is significantly better than sulfuric acid catalysis. The report also compares the powder X-ray diffraction spectra of montmorillonite before and after modification, and provides a preliminary discussion of the mechanism. The reaction conditions are mild, and have implications for the synthesis of small molecule esters.
- Undergraduate teaching,
- Research experiments,
- Fischer esterification,
- Ultrasonic assist
1. [1]
2. [2]
3. [3]
4. [4]
5. [5]
6. [6]
7. [7]
  Mwangi, M. T.; Schulz, M. D.; Bowden, N. B. Org. Lett. 2009, 11 (1), 33.
8. [8]
  Gessner, R. K.; Chibale, K. Synlett 2009, 17, 2839.
9. [9]
  Parks, D. J.; Piers, W. E. J. Am. Chem. Soc. 1996, 118 (39), 9440.
10. [10]
11. [11]
  Marcoux, L.; Florek, J.; Kleitz, F. Appl. Cat. A- Gen. 2015, 504, 493.
12. [12]
  Sibi, M. P.; Despande, P. K.; Laloggia, A. J. Method for Preparation of Optically Active Diarylalanines. US5623087, 1997-04-22.
13. [13]
  Siddiqui, M. A.; Nan, Y.; Patel, M. F.; Reddy, P. A. P.; Mansoor, U. F.; Meng, Z.; Vitharana, L. D.; Zhao, L.; Mandal, A. K.; Liu, D.; et al. Preparation of Pyrazolo[1,5-a]pyrimidine Compounds as mTOR Inhibitors. WO2011090935, 2011-07-28.
14. [14]
  Yu, X.; Chen, K.; Yang, F.; Zha, S.; Zhu, J. Org. Lett. 2016, 18 (20), 5412.
15. [15]
  Ince, S.; Arslan-Acaroz, D.; Demirel, H. H.; Varol, N.; Ozyurek, H. A.; Zemheri, F.; Kucukkurt, I. Biomed. & Pharmacother. 2017, 96, 263.
16. [16]
  Song, R.; Liu, F.; Yang, J.; Yao, L.; He, L.; Qin, B. J. Macromol. Sci. B 2011, 50 (7), 1260.
17. [17]
  Satou, A.; Sagawa, J.; Sun, H. M.; Sibamoto, Y.; Yonomoto, T. Nucl. Eng. Des. 2021, 379, 111234.
18. [18]
19. [19]
20. [20]
  Schierle, S.; Neumann, S.; Heitel, P.; Willems, S.; Kaiser, A.; Pollinger, J.; Merk, D. J. Med. Chem. 2020, 63 (15), 8369.
21. [21]
  Brown, D. S. Preparation of 3-(3-Amidophenyl)-3,4-dihydroquinazolin-4-ones for Treating Diseases Mediated by Cytokines:WO2000055153,2000-09-21.
22. [22]
  Agbaje, O. C.; Fadeyi, O. O.; Fadeyi, S. A.; Myles, L. E.; Okoro, C. O. Bioorg. Med. Chem. Lett. 2011, 21 (3), 989.
23. [23]
  Badger, G. M.; Harris, R. L. N.; Jones, R. A.; Sasse, J. M. J. Chem. Soc. 1962, 4329.
24. [24]
  Davidek, J. J. Chromatogr. 1962, 9, 363.
25. [25]
26. [26]
  Rathi, J. O.; Shankarling, G. S. ChemistrySelect 2020, 5 (9), 2787.
27. [27]
  Busto, E.; Gotor-Fernandez, V.; Montejo-Bernardo, J.; Garcia-Granda, S.; Gotor, V. Org. Lett. 2007, 5 (9), 2787.
28. [28]
29. [29]
  Hennessy, M. C.; O'Sullivan, T. P. RSC Adv. 2021, 11, 22859.
30. [30]
  Du, R.; Yuan, H.; Zhao, C.; Wang, Y.; Yao, J.; Li, H. Mol. Catal. 2020, 490, 110947.
31. [31]
  Gopinath, R.; Barkakaty, B.; Talukdar, B.; Patel, B. K. J. Org. Chem. 2003, 68 (7), 2944.
32. [32]
  Gaifutdinova, E. K.; Beresnev, V. V. Russ. J. Appl. Chem. 2002, 75 (3), 441.
33. [33]
34. [34]
  Cravotto, G.; Cintas, P. Chem. Eur. J. 2010, 13 (7), 1902.
35. [35]
  Khurana, J. M.; Sahoo, P. K.; Maikap, G. C. Synthetic Commun. 1990, 20 (15), 2267.
36. [36]
  Prousis, K. C.; Avlonitis, N.; Heropoulos, G. A.; Calogeropoulou, T. Ultrason. Sonochem. 2014, 21 (3), 937.
37. [37]
  Funabiki, T.; Sugio, D.; Inui, N.; Maeda, M.; Hitomi, Y. Chem. Commun. 2002, 5, 412.
38. [38]
  Pontes, L. F. B. L.; Souza, J. E. G.; Galembeck, A.; Melo, C. P. Sens. Actuators B Chem. 2013, 177, 1115.
39. [39]
  Mitsudome, T.; Matsuno, T.; Sueoka, S.; Mizugaki, T.; Jitsukawa, K.; Kaneda, K. Green Chem. 2012, 14 (3), 610.
40. [40]
  Bantu, B.; Singh, G.; Kaur, S.; Kumar, N.; Kapur, G. S.; Kant, S.; Malhotra, R. K. Ziegler-Natta Catalyst Systems Comprising a 1,2-Phenylenedioate as Internal Donor, Process for Preparing the Same, and Use the Catalyst for Olefin Polymerization. WO2014013401, 2014-01-23.
41. [41]
  Nagy, N. M.; Jakab, M. A.; Konya, J.; Antus, S. Appl. Clay Sci. 2002, 21 (3/4), 213.
42. [42]
  Ramesh, S.; Prakash, B. S. J.; Bhat, Y. S. Appl. Clay Sci. 2010, 48 (1/2), 159.
43. [43]
  Kanda, L. R. S.; Corazza, M. L.; Zatta, L.; Wypych, F. Fuel 2017, 193, 265.
44. [44]
  Cravotto, G.; Cintas, P. Chem. Soc. Rev. 2006, 35 (2), 180.
45. [45]
  Clark, J.; Kybett, A.; Macquarrie, D.; Barlow, S.; Landon, P. J. Chem. Soc. Chem. Commun. 1989, 1353.
46. [46]
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