The formation of 2,5-dianilino-p-benzoquinone in aniline polymerization

Abstract

The byproducts formed in chem. or electrochem. oxidative polymerisation of aniline in acid medium were separated and characterized by IR, 1H-NMR, and elemental anal. The main byproducts were 2,5-dianilino-p-benzoquinone and its derivatives and the amount of byproducts increased with increasing concentration of oxidants in the polymerisation A possible forming process of the byproducts was proposed.

Key words: INFRARED SPECTROPHOTOMETRY, ELEMENTAL ANALYSIS, NMR SPECTROMETRY, C13 NMR SPECTROMETRY, BENZOQUINONE P, PURIFICATIONS, ANILINE, REDOX POLYMERIZATION, BY-PRODUCT, POLYANILINE

CLC Number:

O631.3

Cite this article

TANG JINSONG;WANG LIXIANG;JING XIABIN;WANG BAOCHEN;WANG FUSONG. The formation of 2,5-dianilino-p-benzoquinone in aniline polymerization[J]. Chin. J. Org. Chem., 1989, 9(5): 457-459.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

[1]	Yasir Mumtaz, Jie Liu, Xin Huang. Copper-Promoted Trifluoromethylthiolation of Anilines with CF₃SO₂Na [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 679-685.
[2]	Keli Wang, Jing Huang, Wei Liu, Zhilin Wu, Xianyong Yu, Jun Jiang, Weimin He. Direct Synthesis of 3-Sulfonylquinolines from N-Propargylanilines with Sulfonyl Chlorides [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2527-2534.
[3]	Xiaolong Fang, Bin Li, Jie Jin, Ning Duan. Homogeneous Catalytic Hydrogenation of Dimethyl Malonate into 1,3-Propanediol [J]. Chinese Journal of Organic Chemistry, 2022, 42(5): 1407-1413.
[4]	Hehua Xu, Xiangtai Meng, Yu Zheng, Jinyue Luo, Shenlin Huang. Electrochemical Annulations of o-Alkynylanilines for Synthesis of 3-Iodoindoles [J]. Chinese Journal of Organic Chemistry, 2021, 41(12): 4696-4703.
[5]	Wenyi Li, Yinheng Tang, Wentao Ouyang, Yuhan Lu, Jinyang Chen, Weimin He. Electrochemical Selenylation of N-Unprotected Anilines for Consturcing 4-(Organylselanyl)anilines [J]. Chinese Journal of Organic Chemistry, 2021, 41(12): 4766-4772.
[6]	Chen Ying, Jing Xiaobi, Yu Lei. Polyaniline-Supported Copper-Catalyzed Buchwald-Hartwig Couplings of Pyrimidin-2-amines [J]. Chinese Journal of Organic Chemistry, 2020, 40(8): 2570-2574.
[7]	Du Xingpeng, Zhang Xi, Hou Fei, Liu Xiaojun, Wang Xicun, Quan Zhengjun. Iodine-Mediated Synthesis of 2-Acylquinoline from Acetophenone and 2-(Arylvinyl)aniline [J]. Chinese Journal of Organic Chemistry, 2020, 40(5): 1337-1344.
[8]	Zhang Xiaopeng, Zhu Yanjie, Zhu Yisong, Li Zhengwei, Zhang Guisheng. Advances in Synthesis of 2,3-Dihydroquinazolin-4(1H)-ones [J]. Chin. J. Org. Chem., 2019, 39(9): 2392-2402.
[9]	Wang Zhen, Zhang Ling, Zhang Fugeng, Wang Bin. Synthesis of β-Carbolines through Tetra-n-butylammonium Bromide-Mediated Cycloaromatization Reaction of N-Methylaniline with Tryptophan Derivatives [J]. Chin. J. Org. Chem., 2019, 39(8): 2323-2327.
[10]	Fang Xiaolong, Duan Ning, Zhang Min, Zhang Chunyan, Liu Rui, Zhu Hongping. Homogeneous Catalytic Hydrogenation of Dimethyl Malonate into Methyl 3-Hydroxypropanoate [J]. Chin. J. Org. Chem., 2019, 39(5): 1450-1455.
[11]	Song Yuwan, Feng Shaojing, Han Wei, Xiao Yaping. Synthesis of Azoxybenzenes by Selective Oxidation of Anilines on Titanium Silicate Molecular Sieves [J]. Chin. J. Org. Chem., 2019, 39(4): 1181-1186.
[12]	Wang Wanqiang, Cheng Lan, Peng Hongying, Yao Weizhong, Zhang Rui, Chen Cheng, Cheng Hua. Synthesis and Biological Activities of New 4-PhenylanilinesContaining the Diphenyl Ether Moiety [J]. Chinese Journal of Organic Chemistry, 2019, 39(10): 2851-2859.
[13]	Xu Linlin, Xu Hui, Lin Haixia, Dai Huixiong. Progress in the Synthesis of Primary Anilines via C-H Bond Functionalization [J]. Chin. J. Org. Chem., 2018, 38(8): 1940-1948.
[14]	Yuan Shuo, Wang Sixi, Chen Jinjie, Zhao Longfei, Yu Bin, Liu Hongmin. Aniline-Promoted Synthesis of Isobenzofuranone Derivatives [J]. Chin. J. Org. Chem., 2018, 38(11): 3009-3015.
[15]	Cai Mao, Han Yanfang, Zhang Qi, Luo Sanzhong. Aniline Catalysis in Bioconjugations and Material Synthesis [J]. Chin. J. Org. Chem., 2018, 38(1): 1-10.

苯胺聚合过程中2,5-二苯胺基对苯醌的生成