The Knoevenagel reaction of benzaldehyde with ethyl cyanoacetate on nano-ZIF-90 catalyst synthesized from zinc acetate dihydrate

Tạ Ngọc Thiện Huy; Lê Huyền Trâm; Ninh Thị Phương; Lê Văn Dương; Lê Đình Khiêm; Lê Ngọc Dương; Phạm Thị Hoa; Nguyễn Khánh Diệu Hồng; Hoàng Như Bình Le Van Duong; Đào Quốc Tùy Dao; Don Ta

doi:10.62239/jca.2026.051

Authors

Ta Ngoc Thien Huy Kien Giang University
Le Huyen Tram School of Chemistry and Life Sciences, Hanoi University of Science and Technology
Ninh Thi Phuong School of Chemistry and Life Sciences, Hanoi University of Science and Technology
Le Van Duong School of Chemistry and Life Sciences, Hanoi University of Science and Technology
Le Dinh Khiem Air Defense-Air Force Academy
Le Ngoc Duong Hanoi Bach Nghe College
Pham Thi Hoa Vietnam Maritime University
Nguyen Khanh Dieu Hong Vietnam Union of Science and Technology Associations
Hoang Nhu Binh School of Chemistry and Life Sciences, Hanoi University of Science and Technology
Đào Quốc Tùy School of Chemistry and Life Sciences, Hanoi University of Science and Technology
Ta Ngoc Don School of Chemistry and Life Sciences, Hanoi University of Science and Technology

DOI:

https://doi.org/10.62239/jca.2026.051

Keywords:

Catalyst, Knoevenagel, ZIF-90, zinc acetate dihydrate, ethyl (E) α-cyanocinnamate

Abstract

ZIF-90 is a next-generation porous material composed of zinc tetrahedra linked by 2-imidazolecarboxaldehyde (IcaH), exhibiting a Zn–Ica–Zn bond angle (145°) that closely mimics the Si–O–Si linkage in conventional zeolites. Owing to the presence of zinc centers and nitrogen-containing ligands, ZIF-90 possesses both Lewis acidic and basic active sites, making it a promising heterogeneous catalyst. In this study, the catalytic performance of nano-sized ZIF-90, synthesized from zinc acetate dihydrate, was evaluated in the Knoevenagel condensation of benzaldehyde (BA) with ethyl cyanoacetate (ECA) in an aqueous medium. The suitable reaction conditions were established at a 1:1.5 BA:ECA molar ratio, a catalyst loading of 1.5 wt.% (based on BA), a reaction temperature of 70 °C, and a reaction time of 6 h. Under these suitable conditions, a BA conversion of 87.21% and an ethyl (E)-α-cyanocinnamate selectivity of 99.15% were achieved.

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References

William Morris, Christian J. Doonan, Hiroyasu Furukawa, Rahul Banerjee, Omar M. Yaghi, J. Am. Chem. Soc., 130 (2008) 12626–12627. https://doi.org/10.1021/ja805222x

Ta Ngoc Don, Vu Dao Thang, Pham Thanh Huyen, Pham Minh Hao, Nguyen Khanh Dieu Hong, Stud. Surf. Sci. Catal., 159 (2006) 197–200. https://doi.org/10.1016/S0167-2991(06)81567-3

Hong K.D. Nguyen, Ngo T. Dinh, Nga L.T. Nguyen, Don Ta Ngoc, J. Porous Mater., 24(2) (2017) 559–566. https://doi.org/10.1007/s10934-016-0291-z

Hong K.D. Nguyen, Ta Ngoc Don, Gopinathan Sankar, Richard A. Catlow, Catal. Commun., 25 (2012) 125–129. https://doi.org/10.1016/j.catcom.2011.11.016

Ta Ngoc Don, Le Van Duong, Nguyen Thi Hong Phuong, Nguyen Thi Thu Huyen, Ta Ngoc Thien Huy, Danh Mo, Bui Thi Thanh Ha, Vy Anh Tran, Can. J. Chem. Eng., 103(1) (2025) 311–322. https://doi.org/10.1002/cjce.25382

Ta Ngoc Don, Le Van Duong, Nguyen Thi Hong Phuong, Nguyen Thi Minh Thu, Nguyen Thi Thu Huyen, Trinh Xuan Bai, Ta Ngoc Thien Huy, Danh Mo, Ngo Trong Nghia, Ha Thi Lan Anh, Nguyen Thi Linh, Bui Thi Thanh Ha, Le Thi Nhu Quynh, Trinh Thi Hai, Vietnam J. Catal. Adsorpt., 12(3) (2023) 1–16. https://doi.org/10.51316/jca.2023.041

Hung-Ying Chen, Chih-Wei Chang, J. Phys. Chem. C, 124(16) (2020) 8854–8860. https://doi.org/10.1021/acs.jpcc.0c01472

Yuting Lei, Guihua Zhang, Qinglan Zhang, Ling Yu, Hua Li, Haili Yu, Yi He, Nat. Commun., 12(1) (2021) 1–8. https://doi.org/10.1038/s41467-021-24830-1

Ander Chapartegui-Arias, Anna Raysyan, Ana M. Belenguer, Carsten Jaeger, Teodor Tchipilov, Carsten Prinz, Carlos Abad, Sebastian Beyer, Rudolf J. Schneider, Franziska Emmerling, Chem. Eur. J., 27 (2021) 9414–9421. https://doi.org/10.1002/chem.202100803

Yong Pan, Xi Yu, Sep. Purif. Technol., 237 (2020) 116330. https://doi.org/10.1016/j.seppur.2019.116330

Justyna Rogacka, Agnieszka Seremak, Azahara Luna-Triguero, Filip Formalik, Ismael Matito-Martos, Lucyna Firlej, Sofia Calero, Bogdan Kuchta, Chem. Eng. J., 403 (2021) 126392. https://doi.org/10.1016/j.cej.2020.126392

Yong Pan, Rui Xie, BaoMing Xu, Chi Chen, Microporous Mesoporous Mater., 320 (2021) 111086. https://doi.org/10.1016/j.micromeso.2021.111086

Chaochao Chen, Margarita Vázquez-González, Michael P. O'Hagan, Yu Ouyang, Zhanhui Wang, Itamar Willner, Small, 18(11) (2022) 2104420. https://doi.org/10.1002/smll.202104420

Kaixun Zhu, Yuncong Li, Zhengyi Li, Yixuan Liu, Hongguo Wu, Hu Li, Chem. Commun., (2022) Advance Article. https://doi.org/10.1039/D2CC04643A

Ta Ngoc Thien Huy, Le Huyen Tram, Nguyen Van Thanh, Tran Thi Thao Vy, Le Ngoc Duong, Nhu Thi Thao, Bui Thi Thanh Ha, Ninh Thi Phuong, Le Van Duong, Ta Ngoc Don, Vietnam J. Catal. Adsorpt., 14(2) (2025) 71–76. https://doi.org/10.62239/jca.2025.018

Meizhen Gao, Jing Wang, Zhenghao Rong, Qi Shi, Jinxiang Dong, RSC Adv., 8 (2018) 39627–39634. https://doi.org/10.1039/C8RA08460B

Qi Shi, Jing Wang, Hua Shang, Honghao Bai, Yu Zhao, Jiangfeng Yang, Jinxiang Dong, Jinping Li, Sep. Purif. Technol., 230 (2020) 115850. https://doi.org/10.1016/j.seppur.2019.115850

Zemin Ji, Zijin Zhang, Weifeng Lv, Yanyao Shi, Kai Wang, Shumin Ni, Hongchao Ma, Meiwen Cao, Colloids Surf. A Physicochem. Eng. Asp., 677 (2023) 132338. https://doi.org/10.1016/j.colsurfa.2023.132338

Xianchun Chen, Wenjun Cai, Lu Wang, Bo Wang, J. Am. Chem. Soc., 146(33) (2024) 23138–23145. https://doi.org/10.1021/jacs.4c05044

Yujie Li, Huining Chai, Zhishuang Yuan, Ziyan Zhang, Yiming Zhao, Kun Yu, Yingjie Sun, Guangyao Zhang, Talanta, 276 (2024) 126253. https://doi.org/10.1016/j.talanta.2024.126253

Aljaž Škrjanc, Amalija Golobič, Matjaž Mazaj, Matej Huš, Blaž Likozar, Nataša Zabukovec Logar, Microporous Mesoporous Mater., (2025) 113453. https://doi.org/10.1016/j.micromeso.2024.113453

Ciara Byrne, Matjaž Mazaj, Nataša Zabukovec Logar, Mater. Chem. Phys., 332 (2025) 130143. https://doi.org/10.1016/j.matchemphys.2024.130143

Haiwei Li, Xiao Feng, Yuexin Guo, Didi Chen, Rui Li, Xiaoqian Ren, Xin Jiang, Yuping Dong, Bo Wang, Sci. Rep., 4 (2014) 4366. https://doi.org/10.1038/srep04366

Ta Ngoc Thien Huy, Le Van Duong, Tran Thi Thao Vy, Le Ngoc Duong, Bui Thi Thanh Ha, Trinh Xuan Bai, Nguyen Thi Linh, Nguyen Thi Hong Phuong, Ta Ngoc Don, Vietnam J. Catal. Adsorpt., 14(3) (2025) 139–144. https://doi.org/10.62239/jca.2025.052

D. Elhamifar, S. Kazempoor, B. Karimi, Catal. Sci. Technol., 6 (2016) 4318–4326. https://doi.org/10.1039/C5CY01666E

D.K. Dumbre, T. Mozammel, P.R. Selvakannan, S.B.A. Hamid, V.R. Choudhary, S.K. Bhargava, J. Colloid Interface Sci., 441 (2015) 52–58. https://doi.org/10.1016/j.jcis.2014.11.018

G.B.B. Varadwaj, S. Rana, K.M. Parida, Dalton Trans., 42 (2013) 5122–5129. https://doi.org/10.1039/C3DT32495H

A. Ying, L. Wang, F. Qiu, H. Hu, J. Yang, C. R. Chim., 18 (2015) 223–232. https://doi.org/10.1016/j.crci.2014.05.012

D. Wang, B. Wang, Y. Ding, H. Wu, P. Wu, Chem. Commun., 51 (2016) 12817–12820. https://doi.org/10.1039/C6CC06779D

P. Li, C.-Y. Cao, Z. Chen, H. Liu, Y. Yu, W.-G. Song, Chem. Commun., 48 (2012) 10541–10543. https://doi.org/10.1039/C2CC35718F

Y. Zhang, X. Zhang, R. Bai, X. Hou, J. Li, Catalysts, 8 (2018) 315. https://doi.org/10.3390/catal8080315

Sang-Wha Lee, Vy Anh Tran, Le Thi Nhu Quynh, Thu-Thao Thi Vo, Phuc An Nguyen, Ta Ngoc Don, Yasser Vasseghian, Hung Phan, Environ. Res., 204(D) (2022) 112364. https://doi.org/10.1016/j.envres.2021.112364

M.N. Timofeeva, I.A. Lukoyanov, V.N. Panchenko, S.H. Jhung, Russ. Chem. Bull., 71 (2022) 599–612. https://doi.org/10.1007/s11172-022-3458-6

P.D. Du, N.V.D. Thanh, N.T. Hieu, Adv. Mater. Sci. Eng., (2019) 1–8. https://doi.org/10.1155/2019/6707143

A. Phan, C.J. Doonan, F.J. Uribe-Romo, C.B. Knobler, M. O'Keeffe, O.M. Yaghi, Acc. Chem. Res., 43(1) (2010) 58–67. https://doi.org/10.1021/ar900116g