SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2022 , Vol. 42 >Issue 4: 1179 - 1187

DOI: https://doi.org/10.6023/cjoc202109031

Original article

Tetraethylenepentamine Functionalized Phenolic Resin as Highly Active Acid-Base Bifunctional Catalyst for Knoevenagel Condensation Reaction

  • JIan Xiao ,
  • Zhiying Wu ,
  • Ziyi Chen ,
  • Pengfei Zhao
Expand
  • College of Pharmacy, North China University of Science and Technology, Tangshan, Hebei 063210
* E-mail:

Received date: 2021-09-21

  Revised date: 2021-11-06

  Online published: 2021-12-08

Supported by

Natural Science Foundation of Hebei Province(H2020209288)

Fold

Abstract

The tetraethylenepentamine functionalized phenolic resin (TEPA-PR) for Knoevenagel condensation reaction has been prepared by aminating a commercially available phenolic resin (PR) and tetraethylenepentamine. The TEPA-PR was characterized by Fourier-transfer infrared spectroscopy (FTIR), X-ray diffraction spectra (XRD) and elemental analysis (EA). The TEPA-PR can efficiently catalyze Knoevenagel condensation reaction of aromatic aldehydes with high yields of a wide range of products. Furthermore, the reaction can be easily carried out in different solvents of different polarity. The novel developed resin catalyst shows good reusability (5 times) without significant decrease of catalytic activity.

Key words： phenolic resin; acid-base catalysis; heterogeneous catalysis; Knoevenagel condensation reaction; water phase catalysis

Cite this article

JIan Xiao , Zhiying Wu , Ziyi Chen , Pengfei Zhao . Tetraethylenepentamine Functionalized Phenolic Resin as Highly Active Acid-Base Bifunctional Catalyst for Knoevenagel Condensation Reaction[J]. Chinese Journal of Organic Chemistry, 2022 , 42(4) : 1179 -1187 . DOI: 10.6023/cjoc202109031

References

[1]
(a) Varga G.; Kukovecz Á.; Kónya Z.; Sipos P.; Pálinkó I. J. Catal. 2020, 381, 308.
[1]
(b) Moteki T.; Koga Y.; Ogura M. J. Catal. 2019, 378, 131.
[1]
(c) Zacuto M. J. J. Org. Chem. 2019, 84, 6465.
[1]
(d) Li J. P. H.; Kennedy E. M.; Adesina A. A.; Stockenhuber M. J. Catal. 2019, 369, 157.
[1]
(e) Jia Y.; Fang Y.; Zhang Y.; Miras H. N.; Song Y. Chem.-Eur. J. 2015, 21, 14862.
[1]
(f) Garrabou X.; Wicky B. I. M.; Hilvert D. J. Am. Chem. Soc. 2016, 138, 6972.
[1]
(g) Franconetti A.; Domínguez-Rodríguez P.; Lara-García D.; Prado-Gotor R.; Cabrera-Escribano F. Appl. Catal. A: Gen. 2016, 517, 176.
[1]
(h) Ezugwu C. I.; Mousavi B.; Asraf M. A.; Luo Z.; Verpoort F. J. Catal. 2016, 344, 445.
[2]
(a) Kumar N. S.; Reddy M. S.; S. Kumar T. S.; Bheeram V. R.; Mukkamala S. B.; Rao L. C. ChemistrySelect 2019, 4, 1188.
[2]
(b) Gu X.; Tang Y.; Zhang X.; Luo Z.; Lu H. New J. Chem. 2016, 40, 6580.
[2]
(c) Pandey R.; Singh D.; Thakur N.; Raj K. K. ACS Omega 2021, 6, 13240.
[2]
(d) Grass J.; Klühspies K.; Reiprich B.; Schwieger W.; Inayat A. Catalysts 2021, 11, 474.
[2]
(e) Das A.; Anbu N.; SK M. Dalton Trans. 2019, 4, 17371.
[2]
(f) Zhang X.; Zhang R.; Jin Y.; Li T. J. Solid State Chem. 2019, 278, 120927.
[2]
(g) Guo C. Y.; Zhang Y. H.; Zhang L.; Zhang Y.; Wang J. D. CrystEngComm 2018, 20, 5327.
[3]
(a) Das A.; Anbu N.; Dhakshinamoorthy A.; Biswas S. Microporous Mesoporous Mater. 2019, 284, 459.
[3]
(b) Gao M.; Qi M.; Liu L.; Han Z. Chem. Commun. 2019, 55, 6377.
[4]
(a) Zhang X. Y.; He X. Y.; Zhao S. H. Green Chem Lett. Rev. 2021, 14, 85.
[4]
(b) Jiang Y.; Jiang F.; Liao X.; Lai S.; Wang S.; Xiong X.; Zheng J.; Liu Y. J. Porous Mater. 2020, 27, 779.
[5]
(a) Appaturi J. N.; Pulingam T.; Rajabathar J. R.; Khoerunnisa F.; Ling T. C.; Tan S. H.; Ng E. Microporous Mesoporous Mater. 2021, 320, 111091.
[5]
(b) Li R. J.; Chen C.; Hu L. Y.; ChemistrySelect 2020, 5, 14578.
[6]
(a) Jaenicke S.; Chuah G. K.; Lin X. H.; Hu X. C. Micro¬porous Mesoporous Mater. 2000, 35-36, 143.
[7]
(a) Qian B.; Wang F.; Li D.; Li Y. Zhang B.; Zhu J. New J. Chem. 2020, 44, 5995.
[7]
(b) Zhu J.; Wang F.; Li D.; Zhai J.; Liu P.; Zhang W.; Li Y.; Catal. Lett. 2020, 150, 1909.
[7]
(c) Xue B.; Liu X.; Liu N.; Li Y. Res. Chem. Intermed. 2018, 44, 1523.
[8]
(a) Hajizadeh F.; Maleki B.; Zonoz F. M.; Amiri A. J. Iran. Chem. Soc. 2021, 18, 793.
[8]
(b) Hu Y.; Zhang J.; Wang Z.; Huo H.; Jiang Y.; Xu X.; Lin K. ACS Appl. Mater. Inter. 2020, 12, 36159.
[9]
(a) Zhang X.; He X.; Zhao S. Green Chem. Lett. Rev. 2021, 14, 85.
[9]
(b) Gilanizadeh M.; Zeynizadeh B. Can. J. Chem. 2021, 99, 531.
[10]
(a) Yao C.; Zhou S.; Kang X.; Zhao Y.; Yan R.; Zhang Y.; Wen L. Inorg. Chem. 2018, 57, 11157.
[10]
(b) Sarmah B.; Srivastava R. Mol. Catal. 2017, 427, 62.
[10]
(c) Zhang L.; Wang H.; Shen W.; Qin Z.; Wang J.; Fan W. J. Catal. 2016, 344, 293.
[11]
Xiao J.; Wang L.; Ran J.; Zhao J.; Ma N.; Tao M.; Zhang W. J. Cleaner Prod. 2020, 274, 122473.
[12]
Laha B.; Khullar S.; Gogia A.; Mandal S. K. Dalton Trans. 2020, 49, 12298.
[13]
Sadjadi S.; Akbari M.; Kahangi F. G.; Heravi M. M. Polyhedron 2020, 179, 114375.
[14]
Tian H.; Liu S.; Zhang Z.; Dang T.; Lu Y.; Liu S. ACS Sustainable Chem. Eng. 2021, 9, 4660.
[15]
Zabihzadeh M.; Omidi A.; Shirini F.; Tajik H.; Langarudi M. S. N. J. Mol. Struct. 2020, 1206, 127730.
[16]
Wen H.; Xie J.; Zhou Y.; Zhou Y.; Wang J. Catal. Sci. Technol. 2019, 9, 5725.
[17]
Xu Q.; Niu Y.; Wang G.; Li Y.; Zhao Y.; Singh V.; Niu J.; Wang J. Mol. Catal. 2018, 453, 93.
[18]
Taher A.; Lee D.; Lee B.; Lee I. Synlett. 2016, 27, 1433.
[19]
Modak A.; Mondal J.; Bhaumik A. Appl. Catal. A: Gen. 2013, 459, 41.
[20]
Rong N.; Qiu T.; Qian R.; Lu L.; Huang X.; Ma Z.; Cui C. Inorg. Chem. Commun. 2017, 86, 98.
[21]
Blanco-Ania D.; Valderas-Cortina C.; Hermkens P. H. H.; Sliedregt L. A. J. M.; Scheeren H. W.; Rutjes F. P. J. T. Molecules 2010, 15, 2269.
[22]
Balalaie S.; Bararjanian M.; Hekmat S.; Salehi P. Synth. Commun. 2006, 36, 3703.
[23]
Xu H.; Pan L.; Fang X.; Liu B.; Zhang W.; Lu M.; Chang H. Tetrahedron Lett. 2017, 58, 2360.
[24]
Li J.; Lear M. J.; Hayashi Y. Chem.-Eur. J. 2021, 27, 5901.
[25]
Shi D. Q.; Chen J.; Zhuang Q. Y.; Wang X. S.; Hu H. W. Chin. Chem. Lett. 2003, 14, 1242.
[26]
Tukhtaev H. B.; Ivanov K. L.; Bezzubov S. I.; Cheshkov D. A.; Melnikov M. Y.; Budynina E. M. Org. Lett. 2019, 21, 1087.
[27]
Ren Y. M.; Cai C. Catal. Lett. 2007, 118, 134.
[28]
Wiles C.; Watts P. Haswell S. J. Lab Chip 2007, 7, 322.
[29]
Yadav J. S.; Reddy B. V. S.; Basak A. K.; Visali B.; Narsaiah A. V.; Nagaiah K. Eur. J. Org. Chem. 2004, 2004, 546.
Options
Outlines

/

〈 〉