Deep eutectic solvents used as catalysts for synthesis of 1,10-phenanthroline by improved Skraup reaction

被引:4
|
作者
Wu, Mingliang [1 ,2 ]
Bai, Yuansheng [1 ]
Chen, Xuejun [1 ]
Wang, Qingyin [1 ]
Wang, Gongying [1 ,2 ]
机构
[1] Chinese Acad Sci, Chengdu Inst Organ Chem, Chengdu 610041, Sichuan, Peoples R China
[2] Univ Chinese Acad Sci, Natl Engn Lab VOCs Pollut Control Mat & Technol, 19A Yuquan Rd, Beijing 100049, Peoples R China
关键词
Skraup reaction; 1,10-phenanthroline; Deep eutectic solvent; Choline chloride; Acrolein; 8-aminoquinoline;
D O I
10.1007/s11164-021-04482-y
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
In this study, three different choline chloride-based deep eutectic solvents were synthesized. And it is the first time to synthesize 1,10-phenanthroline through an improved Skraup reaction using deep eutectic solvent as the new catalyst from acrolein and 8-aminoquinoline. The deep eutectic solvents were characterized by Fourier transform infrared (FT-IR), H-1 nuclear magnetic resonance (H-1 NMR), pH/mV meter, and thermogravimetric analysis (TGA). The research results show that the deep eutectic solvent formed by sulfanilic acid and choline chloride has the strongest acidity and highest catalytic active among the three deep eutectic solvents. Besides, the impacts of reaction parameters and molar ratio of raw materials on the reaction were also investigated. Under the optimized reaction conditions, the maximum selectivity and yield of 1,10-phenanthroline were achieved as 84.6 and 75.6%, respectively. The synthesis method, meanwhile, also has simple preparation process and low cheaper catalyst raw. [GRAPHICS] .
引用
收藏
页码:3551 / 3567
页数:17
相关论文
共 50 条
  • [1] Deep eutectic solvents used as catalysts for synthesis of 1,10-phenanthroline by improved Skraup reaction
    Mingliang Wu
    Yuansheng Bai
    Xuejun Chen
    Qingyin Wang
    Gongying Wang
    Research on Chemical Intermediates, 2021, 47 : 3551 - 3567
  • [2] New family of Type V eutectic solvents based on 1,10-phenanthroline and their application in metal extraction
    Crema, Anna P. S.
    Schaeffer, Nicolas
    Bastos, Henrique
    Silva, Liliana P.
    Abranches, Dinis O.
    Passos, Helena
    Hespanhol, Maria C.
    Coutinho, Joao A. P.
    HYDROMETALLURGY, 2023, 215
  • [3] SYNTHESIS OF SOME 1,10-PHENANTHROLINE DERIVATIVES
    MOHAMED, EA
    TAWFIK, AM
    MORSY, JM
    JOURNAL OF THE INDIAN CHEMICAL SOCIETY, 1995, 72 (02) : 93 - 97
  • [4] Mechanochemical reaction of 1,10-phenanthroline with metallic iron
    Drozdova, M.K.
    Myakishev, K.G.
    Ikorskij, V.N.
    Aksenov, V.K.
    Vokov, V.V.
    2003, Maik Nauka (29):
  • [5] REACTION OF 1,10-PHENANTHROLINE WITH HYDROGEN-ION
    KULBA, FY
    MAKASHEV, YA
    FEDYAEV, NI
    ZHURNAL NEORGANICHESKOI KHIMII, 1976, 21 (08): : 2142 - 2148
  • [6] Mechanochemical reaction of 1,10-phenanthroline with metallic iron
    Drozdova, MK
    Myakishev, KG
    Ikorskii, VN
    Aksenov, VK
    Volkov, VV
    RUSSIAN JOURNAL OF COORDINATION CHEMISTRY, 2003, 29 (04) : 234 - 236
  • [7] Mechanochemical Reaction of 1,10-Phenanthroline with Metallic Iron
    M. K. Drozdova
    K. G. Myakishev
    V. N. Ikorskii
    V. K. Aksenov
    V. V. Volkov
    Russian Journal of Coordination Chemistry, 2003, 29 : 234 - 236
  • [8] Improved Synthesis of 2,9-Dichloro-1,10-phenanthroline
    Guo, H. C.
    Zheng, R. H.
    Jiang, H. J.
    ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2012, 44 (04) : 392 - 396
  • [9] Silica-gel-supported deep eutectic solvent (DES) as an efficient novel catalytic system for synthesis of 1,10-phenanthroline
    Mingliang Wu
    Yuansheng Bai
    Qingyin Wang
    Gongying Wang
    Research on Chemical Intermediates, 2022, 48 : 2575 - 2591
  • [10] Silica-gel-supported deep eutectic solvent (DES) as an efficient novel catalytic system for synthesis of 1,10-phenanthroline
    Wu, Mingliang
    Bai, Yuansheng
    Wang, Qingyin
    Wang, Gongying
    RESEARCH ON CHEMICAL INTERMEDIATES, 2022, 48 (06) : 2575 - 2591