Se/ZrO2-Catalyzed Oxidative Polymerization of Aniline

doi:10.6023/cjoc202404022

Abstract

Polyanilines (PANIs) are widely employed materials that are synthesized via the oxidative polymerization of anilines. However, the present synthetic methods always require the use of chemical oxidants and employ HCl/NaOH as the acid-base regulator, resulting in a large amount of waste salt and residual impurities in the material that affect its performance. These drawbacks are unfavorable for industrial applications. A novel method for the preparation of PANIs, i.e. the Se/ZrO₂- catalyzed oxidative polymerization of aniline with O₂ free of the acid-base regulator is developed. The relatively safe and green features of the method make it more practical for large-scale applications. Researches showed that PANIs prepared by this method could be used as the support to anchor palladium catalyst, and its activity was as good as that of the materials synthesized via traditional methods.

Key words: selenium, zirconia, catalyzed oxidation, aniline, polyaniline

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Daming Yong, Tingting Zuo, Qichao Wu, Xu Zhang. Se/ZrO₂-Catalyzed Oxidative Polymerization of Aniline[J]. Chinese Journal of Organic Chemistry, 2024, 44(11): 3392-3398.

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Fig. & Tab. 6

Scheme 1. Methods for the synthesis of PANI

Figure 1. (a) Photographs of the samples after 3, 5, 8 or 10 h reaction respectively (from left to right), (b) UV-Vis spectra of the samples at different reaction times, and (c) FT-IR spectrum of the prepared PANI

Figure 2. Catalyst recycling and reusing (reaction for 10 h)

Entry	Method^b	X	R	Product	Yield^c/%	TON^d
1	V	I	H	A	99	8.8×10³
2	I	I	H	A	82	6.2×10³
3	II	I	H	A	86	5.7×10³
4	III	I	H	A	99	0.2×10³
5	IV	I	H	A	94	8.0×10³
6	V	Br	H	A	72	6.4×10³
7	I	Br	H	A	55	4.2 ×10³
8	II	Br	H	A	55	3.6×10³
9	III	Br	H	A	68	0.1×10³
10	IV	Br	H	A	66	5.6×10³
11	V	Br	NO₂	B	75	6.7×10³
12	V	Cl	H	A	8	0.7×10³
13	V	Cl	NO₂	B	17	1.5×10³

Table 1. Catalytic activity evaluation of the Pd@PANI prepared via different methods

Scheme 2. Mechanism of the catalysis circle

Scheme 3. Mechanism for the polymer chain growing

References 32

[1]	(a) Bai L.; Shi Y.; Zhang X.; Cao X.; Jia J.; Shi H.; Lu W. Analyst 2023, 148, 3359.
	(b) Zhang Y.-Y.; Zhang J.; Wang G.-L.; Wang Z.-F.; Luo Z.-W.; Zhang M. Rare Metals 2023, 42, 2344.
	(c) Zheng Q.-Y.; Yang M.; Dong X.; Zhang X.-F.; Cheng X.-L.; Huo L.-H.; Major Z.; Xu Y.-M. Rare Metals 2023, 42, 536.
	(d) Miao Z.; Wang P.; Zhong A.; Yang M.; Xu Q.; Hao S.; Hu X. J. Electroanal. Chem. 2015, 756, 153.
[2]	(a) Zhu A.; Zhang J.; Situ B.; Ma Y.; Ji Z.; Peng Z.; Yan Z.; Tu Y. J. Polym. Res. 2023, 30, 417.
	(b) Zhang W.; Xia T.; Huo X.; Li X.; Park S.; Lin L.; Diao G.; Piao Y. J. Electroanal. Chem. 2022, 920, 116615.
	(c) Zhang W.; Kong Y.; Jin X.; Yan B.; Diao G.; Piao Y. Electrochim. Acta 2020, 331, 135345.
	(d) Lyu L.; Chai H.; Seong K.-D.; Lee C.; Kang J.; Zhang W.; Piao Y. Electrochim. Acta 2018, 291, 256.
[3]	(a) Sun P.; Shen X.; Xu P.; Huang W.; Xu Q. Appl. Surf. Sci. 2024, 655, 159649.
	(b) Chen Y.; Lei J.; Zhai Y.; Zhu Z.; Wu W.; Lu X. Chin. Chem. Lett. 2023, 34, 108305.
	(c) Zhang T.; Zhang P.; Liao Z.; Wang F.; Wang J.; Wang M.; Zschech E.; Zhuang X.; Schmidt O. G.; Feng X. Chin. Chem. Lett. 2022, 33, 3921.
	(d) Gautam J.; Liu Y.; Gu J.; Ma Z.; Dahal B.; Chishti A. N.; Ni L.; Diao G.; Wei Y. J. Colloid Interface Sci. 2022, 614, 642.
[4]	(a) Yuan G.; Xi Z.; Wang C.; Sun X.; Han J.; Guo R. Acta Phys.-Chim. Sin. 2023, 39, 2212061.
	(b) Li W.; Wang F.; Shi Y.; Yu L. Chin. Chem. Lett. 2023, 34, 107505.
	(c) Zeng Z.; Chen Y.; Zhu X.; Yu L. Chin. Chem. Lett. 2023, 34, 107728.
	(d) Zhang Y.; Sun H.; Chen Y.; Shi Y.; Yu L. Org. Lett. 2023, 25, 7928.
	(e) Chen Y.; Yu L.; Zhou H. J. Phys. Chem. C 2022, 126, 17084.
[5]	(a) Li X.; Liu H.; Meng S.; Liu X.; Liu X.; He R.; Wang F. Cream. Int. 2024, 50, 12361.
	(b) Yu S.; Liu Y.; Mo R.; Li Y.; Zhou Z.; Zhang L.; Fan B.; Cao Y. New J. Chem. 2024, 48, 4810.
	(c) Yu H.; Xu Z.; Fang T.; Zhang M.; Xu Y.; Liu J.; Tan X. Polym. Adv. Technol. 2024, 35, e6307.
	(d) Li C.; Li Y.; Chen Q.; Sun D.; Li H.; Chen W.; Yan J.; Wu G.; Yuan X.; Wang S.; He Y.; Yu H. Prog. Org. Coat. 2024, 187, 108173.
[6]	Oh W. K.; Kim S.; Kwon O.; Jang J. J. Nanosci. Nanotechnol. 2011, 11, 4254.
[7]	(a) Zhou Y.; Zhang Y.-H.; Ma J.-S.; Yu M.-P.; Qiu H. Int. J. Miner.,Metall. Mater. 2018, 25, 1329.
	(b) Li Y.; Cao S.; Fan L.; Han J.; Wang M.; Guo R. J. Colloid. Interface Sci. 2018, 527, 241.
[8]	(a) Zhang Y.; Li W.; Hu Z.; Jing X.; Yu L. Chin. Chem. Lett. 2024, 35, 108938.
	(b) Meng X.; Zhang Y.; Zhou H.; Yu L. ACS Sustainable Chem. Eng. 2022, 10, 7658.
[9]	(a) Han H. B.; Zhou S. S.; Zhang D. J.; Feng S.-W.; Li L.-F.; Liu K.; Feng W.-F.; Nie J.; Li H.; Huang X.-J.; Armand M.; Zhou Z.-B. J. Power Sources 2011, 196, 3623.
	(b) Ghosh S. K.; Waghoo G.; Kalita A.; Balgude D.; Kumar K. R. Prog. Org. Coat. 2012, 73, 70.
	(c) Liu J.; Cai Y.; Pang H.; Cao B.; Luo C.; Hu Z.; Xiao C.; Zhang H.; Lv F.; Cao Y.; Yu L. Chin. Chem. Lett. 2022, 33, 4061.
[10]	(a) Pei C.; Chen S.; Fu D.; Zhao Z.-J.; Gong J. Chem. Rev. 2024, 124, 2955.
	(b) Gu Y.; Wang L.; Xu B.-Q.; Shi H. Chin. J. Catal. 2023, 54, 1.
	(c) Yang F.; Tian X.; Luo W.; Feng L. Coord. Chem. Rev. 2023, 478, 214980.
[11]	(a) Liu Y.; Tang D.; Cao K.; Yu L.; Han J.; Xu Q. J. Catal. 2018, 360, 250.
	(b) Chen Y.; Li L.; Zhang L.; Han J. Colloid Polym. Sci. 2018, 296, 567.
	(c) Shi F.; Yan F.; Zhang X.; Liu R.; Jiang G.; Li J.; Malinick A.; Cheng Q.; Yang Z. Chem. Commun. 2023, 59, 8294.
[12]	Li H.-F.; Yu K.-W.; Jing X.-B.; Duan L.; Zhang Y.-Y. Rare Metals 2024, 43, 1337.
[13]	(a) Li H.; Cao H.; Chen T.; Zhang X.; Shi Y. Mol. Catal. 2020, 483, 110715.
	(b) Qiu C.; Sun Y.; Xu Y.; Zhang B.; Zhang X.; Yu L.; Su C. ChemSusChem 2021, 14, 3344.
	(c) Yan J.; Fang W.; Wei Z.; Chi J.; Chen M.; Jiang Z.; Jiang K.; Shen S.; Shangguan W. Appl. Catal., B 2023, 339, 123155.
	(d) Wang Y.; Ma J.-X.; Ren J.; Zhang D.; Xu F.-Y.; Zhang K.; Cao Z.-Q.; Sun Q.-J.; Li G.-D.; Wu S.-W.; Chen H.-H. Rare Metals 2024, 43, 2648.
[14]	(a) Gallo-Rodriguez C.; Rodríguez J. B. Synthesis 2024, 56, 2295.
	(b) Pacuła-Miszewska A. J.; Sancineto L. In Organochalcogen Compounds, Eds.: Lenardão, E. J.; Santi, C.; Perin, G.; Alves, D. Elsevier, 2022, Chapter 7, p 219.
	(c) Xiao X.; Guan C.; Xu J.; Fu W.; Yu L. Green Chem. 2021, 23, 4647.
	(d) H. Cao, R. Qian, L. Yu, Catal. Sci. Technol. 2020, 10, 3113.
	(e) Singh F. V.; Wirth T. Catal. Sci. Technol. 2019, 9, 1073.
	(f) Shao L.; Li Y.; Lu J.; Jiang X. Org. Chem. Front. 2019, 6, 2999.
	(g) Guo R.; Liao L.; Zhao X. Molecules 2017, 22, 835.
[15]	(a) Chen X.; Zhuang S.; Yan W.; Zeng Z.; Feng J.; Cao H.; Yu L. Chin. Chem. Lett. 2024, 35, 109635.
	(b) Zhou W.; Li P.; Liu J.; Yu L. Ind. Eng. Chem. Res. 2020, 59, 10763.
	(c) Yang Y.; Fan X.; Cao H.; Chu S.; Zhang X.; Xu Q.; Yu L. Catal. Sci. Technol. 2018, 8, 5017.
	(d) Li P.; Cao K.; Jing X.; Liu Y.; Yu L. New J. Chem. 2021, 45, 17241.
[16]	(a) Chen X.; Mao J.; Liu C.; Chen C.; Cao H.; Yu L. Chin. Chem. Lett. 2020, 31, 3205.
	(b) Zhu Z.; Wang W.; Zeng L.; Zhang F.; Liu J. Catal. Commun. 2020, 142, 106031.
	(c) Liu M.; Zhang X.; Chu S.; Ge Y.; Huang T.; Liu Y.; Yu L. Chin. Chem. Lett. 2022, 33, 205.
[17]	Yong D.; Tian J.; Yang R.; Wu Q.; Zhang X. Chin. J. Org. Chem. 2024, 44, 1343 (in Chinese).
	(雍达明, 田杰, 杨瑞洪, 吴启超, 张旭, 有机化学, 2024, 44, 1343.) doi: 10.6023/cjoc202310020
[18]	Zhang Y.; Sun H.; Yang Y.; Li H.; Shi Y.; Yu L. Catal. Sci. Technol. 2023, 13, 3791.
[19]	(a) Yuan Y.; Zhang S.; Sun Z.; Su Y.; Ma Q.; Yuan Y.; Jia X. Org. Lett. 2020, 22, 6294. doi: 10.1021/acs.orglett.0c02054 pmid: 32806190
	(b) Lv B.; Gao P.; Zhang S.; Jia X.; Wang M.; Yuan Y. Org. Chem. Front. 2021, 8, 5440. pmid: 32806190
	(c) Lu Q.; Shi G.; Zhou H.; Yuan E.; Chen C.; Ji L. Appl. Catal., A 2022, 630, 118441. pmid: 32806190
	(d) Chen Y.; Chen C.; Liu Y.; Yu L. Chin. Chem. Lett. 2023, 34, 108489. pmid: 32806190
	(e) Li X.; Hua H.; Liu Y.; Yu L. Org. Lett. 2023, 25, 6720. pmid: 32806190
[20]	(a) Liu F.; Feng G.; Lin M.; Wang C.; Hu B.; Qi C. J. Colloid Interface Sci. 2014, 435, 83.
	(b) Liu F.; Zuo S.; Xia X.; Sun J.; Zou Y.; Wang L.; Li C.; Qi C. J. Mater. Chem. A 2013, 1, 4089.
	(c) Wang H.; Kong W.; Zhu W.; Wang L.; Yang S.; Liu F. Catal. Commun. 2014, 50, 87.
	(d) Yu L.; Han Z.; Ding Y. Org. Process Res. Dev. 2016, 20, 2124.
[21]	Kantam M. L.; Roy M.; Roy S.; Sreedhar B.; Madhavendra S. S.; Choudary B. M.; De R. L. Tetrahedron 2007, 63, 8002.
[22]	Gao G.; Han J.; Yu L.; Xu Q. Synlett 2019, 30, 1703. doi: 10.1055/s-0037-1612088
[23]	(a) Xu T.-Y.; Zhang Q.-F.; Jiang D.-H.; Liang Q.-X.; Lu C.-S.; Cen J.; Li X.-N. RSC Adv. 2014, 4, 33347.
	(b) Ding X.; Li M.; Jin J.; Huang X.; Wu X.; Feng L. Chin. Chem. Lett. 2022, 33, 2687.
	(c) Qiao W.; Zha M.; Yang Y.; Hu G.; Feng L. Chem. Commun. 2022, 58, 10651.
	(d) Xue J.; Wu X.; Feng L. Chem. Commun. 2022, 58, 2371.
	(e) Feng Y.; Lu S.; Fu L.; Yang F.; Feng L. Chem. Sci. 2024, 15, 2123.
[24]	Yu L.; Huang Y.; Wei Z.; Ding Y.; Su C.; Xu Q. J. Org. Chem. 2015, 80, 8677.
[25]	(a) Schweitzer-Chaput B.; Sud A.; Pintér Á.; Dehn S.; Schulze P.; Klussmann M. Angew. Chem., Int. Ed. 2013, 52, 13228. pmid: 30102546
	(b) Lippincott D. J.; Trejo-Soto P. J.; Gallou F.; Lipshutz B. H. Org. Lett. 2018, 20, 5094. doi: 10.1021/acs.orglett.8b01883 pmid: 30102546
	(c) Cao H.; Li P.; Jing X.; Zhou H. Chin. J. Org. Chem. 2022, 42, 3890 (in Chinese). pmid: 30102546
	(曹洪恩, 李培梓, 景崤壁, 周宏伟, 有机化学, 2022, 42, 3890.) doi: 10.6023/cjoc202205005 pmid: 30102546
	(d) Wang F.; Qian R.; Yu L. React. Chem. Eng. 2023, 8, 849. pmid: 30102546
[26]	(a) Deng X.; Qian R.; Zhou H.; Yu L. Chin. Chem. Lett. 2021, 32, 1029.
	(b) Liu F.; Zhan J.; Sun Y.; Jing X. Chin. J. Org. Chem. 2021, 41, 2099 (in Chinese).
	(刘峰, 詹杰, 孙扬阳, 景崤壁, 有机化学, 2021, 41, 2099.) doi: 10.6023/cjoc202011012
	(c) Zhou W.; Xiao X.; Liu Y.; Zhang X. Chin. J. Org. Chem. 2022, 42, 1849 (in Chinese).
	(周文见, 肖芯蕊, 刘永红, 张旭, 有机化学, 2022, 42, 1849.) doi: 10.6023/cjoc202201023
	(d) Zhang X.; Zuo T.; Yu L. ChemistrySelect 2022, 7, e202203514.
[27]	(a) Das T. N. J. Phys. Chem. A 2005, 109, 3344.
	(b) Zhang X.; Wei Z.; Yu L. React. Chem. Eng. 2023, 8, 1700.
[28]	Mu S.; Chen C.; Wang J. Synth. Met. 1997, 88, 249.
[29]	(a) Xiao X.; Shao Z.; Yu L. Chin. Chem. Lett. 2021, 32, 2933.
	(b) Ding W.; Wang S.; Gu J.; Yu L. Chin. Chem. Lett. 2023, 34, 108043.
	(c) Xian L.; Li Q.; Li T.; Yu L. Chin. Chem. Lett. 2023, 34, 107878.
	(d) Yin Y.; Quan X.; Cheng Y.; Yang Z.; Zhu J.; Fang W. Food Chem. 2023, 426, 136603.
	(e) Li J.; Shi Q.; Xue Y.; Zheng M.; Liu L.; Geng T.; Gong D.; Zhao M. Chin. Chem. Lett. 2024, 35, 109239.
[30]	(a) Lu F.-D.; Chen J.; Jiang X.; Chen J.-R.; Lu L.-Q.; Xiao W.-J. Chem. Soc. Rev. 2021, 50, 12808.
	(b) Firsan S. J.; Sivakumar V.; Colacot T. J. Chem. Rev. 2022, 122, 16983.
	(c) Wang Y.; He Y.; Zhu S. Acc. Chem. Res. 2023, 56, 3475.
	(d) Zeng Z.; Liao C.; Yu L. Chin. Chem. Lett. 2024, 35, 109349.
[31]	Dilauro G.; García S. M.; Tagarelli D.; Vitale P.; Perna F. M.; Capriati V. ChemSusChem 2018, 11, 3495.
[32]	Barbero M.; Dughera S. Tetrahedron 2018, 74, 5758.

氧化锆负载硒催化苯胺氧化聚合反应

Se/ZrO₂-Catalyzed Oxidative Polymerization of Aniline

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