Citation: GUO Hui, YIN Yuanyuan, ZHANG Xueying, ZHUANG Yuwei, JIAN Cao, ZHANG Guobao. Synthesis of N-Cyanoethyl-N-hydroxyethylaniline Catalyzed by Acdic Ionic Liquid[J]. Chinese Journal of Applied Chemistry, ;2020, 37(5): 512-517. doi: 10.11944/j.issn.1000-0518.2020.05.190287 shu

Synthesis of N-Cyanoethyl-N-hydroxyethylaniline Catalyzed by Acdic Ionic Liquid

High & New Technology Research Center of Henan Academy of Sciences, Zhengzhou 450002, China

Corresponding author: GUO Hui, gh3324@163.com ZHANG Guobao, xiehuwangzi@163.com
Received Date: 25 October 2019
Revised Date: 26 December 2019
Accepted Date: 20 February 2020

Figures(4)

N-Cyanoethyl-N-hydroxyethylaniline is an important dye intermediate with a wide range of applications. A green and efficient protocol for the synthesis of N-cyanoethyl-N-hydroxyethylaniline by reaction of acrylonitrile and N-hydroxyethyl aniline with 1-butyl-3-methylimidazolium hydrosulphates ionic liquid ([Bmim]HSO₄) as the catalyst has been developed, eliminating the inert-gas welding and complex operation of traditional methods. The effect of ionic liquid, the amount of ionic liquid, the ratio of substrates, temperature and time were investigated. The optimum reaction conditions were obtained as follow:[BMIM]HSO₄ 0.8 mmol, n(N-hydroxyethyl aniline):n(acrylonitrile)=1:1.2, reaction time of 12 h, reaction temperature of 90 ℃. The acdic ionic liquid could be easily separated and reused for at least 5 times without significantly decrease in catalytic activity.
- acdic ionic liquid,
- N-cyanoethyl-N-hydroxyethylaniline,
- acrylonitrile,
- N-hydroxyethyl aniline
1. [1]
  Josephy P D, Muhammad Z, Joban D. Potent Mutagenicity in the Ames Test of 2-Cyano-4-Nitroaniline and 2, 6-Dicyano-4-Nitroaniline, Components of Disperse Dyes[J]. Environ Mol Mutagen, 2016,57:10-16.
2. [2]
  Chobanian H R, Fors B P, Lin L S. A Facile Microwave-Assisted Palladium-Catalyzed Cyanntion of Arylchiorides[J]. Tetrahedron Lett, 2006,47:3303-3305.
3. [3]
  HUANG Xun. The Blue Cyano Azo Disperse Dye and Its Cyanidation Protocol[J]. Dyes Ind, 1979,6:8-15.
4. [4]
  LIU Yanying, LI Kunlan. Synthesis of Cyano Diazo Disperse Dyes with Non-cyanide Route[J]. J Dalian Politech, 2011,30(5):372-374.
5. [5]
  LIN Funqin, JIAN Dunlong. A New Method for Synthesis of Cyano Diazo Disperse Dye[J]. Chinese J Appl Chem, 1987,4(5):62-64.
6. [6]
  CHEN Zhiji. The Research on Cyanidation Protocol of Cyano Diazo Disperse Dye[J]. Dyes Ind, 1983,5:19-25.
7. [7]
  Peters A T, Gbadamosi A. Disperse Dyes:4-Hetarylazo Derivatives from N-P-Cyanoethyl-N-P-Hydroxyethylaniline[J]. J Chem Tech Biotechnol, 1992,53(3):301-308.
8. [8]
  Peters A T, Soboyejo N O. Iodo-Substituted 4-Aminoazobenzenes and 4-Phenylazonaphthylamines-Dyes for Synthetic-Polymer Fibres[J]. J Soc Dyers Colour, 1988,104(12):486-491.
9. [9]
  Mehta H P, Peters A T. Substituent Effects on the Colour, Dyeing and Fastness Properties of 4-N-β-Cyanoethyl-N-β-Hydroxyethylaminoazobenzenes Part I-Monosubstituted Derivatives[J]. Dyes Pigm, 1981,2(4):259-261.
10. [10]
  Peters A T. Substituent Effects on the Colour, Dyeing and Fastness Properties of Trisubstituted 4-N-β-Cyanoethyl-N-β-Hydroxyethylaminoazobenzenes[J]. J Soc Dyers Colour, 1985,101(11):361-367.
11. [11]
  WU Lingshuang, FU Danna, HOU Aiqin. Preparation of Cyano-Disperse Dye Inks and Their Ink-Jek Printing Properties[J]. Dye Finish, 2016,5:1-7.
12. [12]
  JIANG Xiaoguang. The Structural Analysis Results of Foron Yellow Bronwn S-2R L(300%)[J]. Shanxi Chem Ind, 1986,4:29-31.
13. [13]
  ZHENG Jing, WEI Xianhong, LIANG Wei. Synthesis of the Dyestuff Intermediate N-Cyanoethyl-N-Acetoxyethylaniline[J]. J Gansu Sci, 2006,18(4):40-42.
14. [14]
  ZHANG Wengang, TAO Binbin, DING Xingcheng. Study on Synthesis of N-Cyanoethyl-N-Cyanoethoxyethylaniline[J]. Dyes Color, 2018,55(5):29-30.
15. [15]
  YU Qingjie, SHAN Dong, ZHENG Xiaodu, et al. A Protocol for the Synthesis of 3-[[2-(Benzoyloxy)ethyl]phenylamino] Propiononitrile: China, 201611008345.7[P]. 2016-11-16(in Chinese).
16. [16]
  Kluger E W, Rolen J L. Process for Hydroxyalkylation of Cyanoethylanilines: US, 4374068[P]. 1983.
17. [17]
  ZHANG Yuan, LI Ying. The Synthetic Research on N-Cyanoethyl-N-Hydroxyethylaniline[J]. Technol Taihua, 1996,1:26-28.
18. [18]
  WANG Liangjie, XIONG Ying. Study of Synthesizing N-Cyanoethyl-N-Acetoxyethylaniline[J]. Dyes Ind, 1996,33(3):39-44.
19. [19]
  Zhang Q H, Zhang S G, Deng Y Q. Recent Advances in Ionic Liquid Catalysis[J]. Green Chem, 2011,13(10):2619-2637.
20. [20]
  Kang X C, Zhu Q G, Sun X F. Highly Eficient Electrochemical Reduction of CO₂ to CH₄ in an Ionic Liquid Using a Metal-Organic Framework Cathode[J]. Chem Sci, 2016,7(1):266-273.
21. [21]
  Zhang J L, Chen S M, Zhang H T. Electrodeposition of Crystalline Silicon Directly from Silicon Tetrachloride in Ionic Liquid at Low Temperature[J]. RSC Adv, 2016,6(4):12061-12067.
22. [22]
  Zhu A L, Wang M Y, Li L J. Tetramethylguanidium-Based Ionic Liquids as Efficient and Reusable Catalysts for the Synthesis of Biscoumarin at Room Temperature[J]. RSC Adv, 2015,47(5):73974-73979.
23. [23]
  Ding F, He X, Luo X Y. Highly Efficient CO₂ Capture by Carbonyl-Containing Ionic Liquids Through Lewis Acid Base and Cooperative C—H—O Hydrogen Bonding Interaction Strengthened by the Anion[J]. Chem Commun, 2014,50(95):15041-15044.
24. [24]
  Ahmed E H, Qi Y L, Lai B B. A Sulfone-Containing Imidazolium-Based Brønsted Acid Ionic Liquid Catalyst Enables Replacing Dipolar Aprotic Solvents with Butyl Acetate[J]. Adv Synth Catal, 2019,361(14):3342-3350.
25. [25]
  Ahmed E H, Qi Y L, Yue M E. Novel Non-toxic and Non-hazardous Solvent Systems for the Chemistry of Indoles:Use of a Sulfone-Containing Brønsted Acid Ionic Liquid Catalyst in Butyl Acetate[J]. ChemCatChem, 2019,11(17):4403-4410.
26. [26]
  ZHANG Baohua, SHI Lanxiang. Regioselective Synthesis of Dibenzo[d, f][1, 3]dioxepine[J]. Chinese J Appl Chem, 2018,35(11):1331-1334.
27. [27]
  QU Haonan, BAO Chong, MA Wenjing. Hydrolysis of Cellulose by Solid Carbon Sulfonic Acid Supported 1-Butyl-3-Methylimidazolium Chloride[J]. Chinese J Appl Chem, 2019,36(1):58-64.
28. [28]
  MA Hao, LIAO Chunyan, FAN Meilin. Solubility of Cellulose Anion-functionalized Ionic Liquids on Cellulose[J]. Chinese J Appl Chem, 2018,35(4):449-456.
29. [29]
  Li M H, Wu F T, Gu Y L. Brønsted Acidic Ionic Liquid Catalyzed Synthesis of Benzo[a]carbazole from Renewable Acetol and 2-Phenylindoles in a Biphasic System[J]. Chinese J Catal, 2019,40(8):1135-1140.
30. [30]
  Guo H, Zhuang Y W, Cao J. Green and Efficient Protocol for the Synthesis of N-(2-Hydroxyethyl)anilines by the Alkylation Reaction in Ionic Liquid[J]. Synth Commun, 2014,44(23):3368-3374.
31. [31]
  Guo H, Zhuang Y W, Cao J. Highly Chemo- and Regioselective Reaction of Hydroxybenzenes in Acidic Ionic Liquid[J]. Bull Korean Chem Soc, 2013,34(9):2594-259.
1. [1]
  Caixia Lin , Ting Liu , Zhaojiang Shi , Hong Yan , Keyin Ye , Yaofeng Yuan . Innovative Experiment of Electrochemical Dearomative Spirocyclization of N-Acyl Sulfonamides. University Chemistry, 2025, 40(4): 359-366. doi: 10.12461/PKU.DXHX202406107
2. [2]
  Cong-Bin Ji , Ding-Xiong Xie , Mei Chen , Ye-Ying Lan , Bao-Hua Zhang , Ji-Ying Yang , Zheng-Hui Kang , Shu-Jie Chen , Yu-Wei Zhang , Yun-Lin Liu . Green synthesis of 2-trifluoromethylquinoline skeletons via organocatalytic N-[(α-trifluoromethyl)vinyl]isatins CN bond activation. Chinese Chemical Letters, 2025, 36(7): 110598-. doi: 10.1016/j.cclet.2024.110598
3. [3]
  Xiaofeng Xia , Jielian Zhu . Innovative Comprehensive Experimental Design: Synthesis of 6-Fluoro-N-benzoyl Tetrahydroquinoline. University Chemistry, 2024, 39(10): 344-352. doi: 10.12461/PKU.DXHX202405063
4. [4]
  Junke LIU , Kungui ZHENG , Wenjing SUN , Gaoyang BAI , Guodong BAI , Zuwei YIN , Yao ZHOU , Juntao LI . Preparation of modified high-nickel layered cathode with LiAlO₂/cyclopolyacrylonitrile dual-functional coating. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1461-1473. doi: 10.11862/CJIC.20240189
5. [5]
  Lirui Shen , Kun Liu , Ying Yang , Dongwan Li , Wengui Chang . Synthesis and Application of Decanedioic Acid-N-Hydroxysuccinimide Ester: Exploration of Teaching Reform in Comprehensive Applied Chemistry Experiment. University Chemistry, 2024, 39(8): 212-220. doi: 10.3866/PKU.DXHX202312035
6. [6]
  Junjun Huang , Ran Chen , Yajian Huang , Hang Zhang , Anran Zheng , Qing Xiao , Dan Wu , Ruxia Duan , Zhi Zhou , Fei He , Wei Yi . Discovery of an enantiopure N-[2-hydroxy-3-phenyl piperazine propyl]-aromatic carboxamide derivative as highly selective α_1D/1A-adrenoceptor antagonist and homology modelling. Chinese Chemical Letters, 2024, 35(11): 109594-. doi: 10.1016/j.cclet.2024.109594
7. [7]
  Huixian Weng , Lefei Hu , Lei Hu , Yihan Zhou , Aohua Wang , Ning Wang , Wenzhe Li , Chunliu Zhu , Shiyan Guo , Miaorong Yu , Yong Gan . Corrigendum to "The complexation of insulin with sodium N-[8-(2-hydroxybenzoyl)amino]-caprylate for enhanced oral delivery: Effects of concentration, ratio, and pH" [Chinese Chemical Letters 33 (2022) 1889-1894]. Chinese Chemical Letters, 2025, 36(8): 111316-. doi: 10.1016/j.cclet.2025.111316
8. [8]
  Yanglin Jiang , Mingqing Chen , Min Liang , Yige Yao , Yan Zhang , Peng Wang , Jianping Zhang . Experimental and Theoretical Investigations of Solvent Polarity Effect on ESIPT Mechanism in 4′-N,N-diethylamino-3-hydroxybenzoflavone. Acta Physico-Chimica Sinica, 2025, 41(2): 100012-0. doi: 10.3866/PKU.WHXB202309027
9. [9]
  Zhilian Liu , Wengui Wang , Hongxiao Yang , Yu Cui , Shoufeng Wang . Ideological and Political Education Design for the Synthesis of Irinotecan Drug Intermediate 7-Ethyl Camptothecin. University Chemistry, 2024, 39(2): 89-93. doi: 10.3866/PKU.DXHX202306012
10. [10]
  Xingyang LI , Tianju LIU , Yang GAO , Dandan ZHANG , Yong ZHOU , Meng PAN . A superior methanol-to-propylene catalyst: Construction via synergistic regulation of pore structure and acidic property of high-silica ZSM-5 zeolite. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1279-1289. doi: 10.11862/CJIC.20240026
11. [11]
  Wenjun Zheng . Application in Inorganic Synthesis of Ionic Liquids. University Chemistry, 2024, 39(8): 163-168. doi: 10.3866/PKU.DXHX202401020
12. [12]
  Ying Li , Yushen Zhao , Kai Chen , Xu Liu , Tingfeng Yi , Li-Feng Chen . Rational Design of Cross-Linked N-Doped C-Sn Nanofibers as Free-Standing Electrodes towards High-Performance Li-Ion Battery Anodes. Acta Physico-Chimica Sinica, 2024, 40(3): 2305007-0. doi: 10.3866/PKU.WHXB202305007
13. [13]
  Yameen Ahmed , Xiangxiang Feng , Yuanji Gao , Yang Ding , Caoyu Long , Mustafa Haider , Hengyue Li , Zhuan Li , Shicheng Huang , Makhsud I. Saidaminov , Junliang Yang . Interface Modification by Ionic Liquid for Efficient and Stable FAPbI₃ Perovskite Solar Cells. Acta Physico-Chimica Sinica, 2024, 40(6): 2303057-0. doi: 10.3866/PKU.WHXB202303057
14. [14]
  Zhanhui Yang , Jiaxi Xu . (m+n+…) or [m+n+…]cycloaddition?. University Chemistry, 2025, 40(3): 387-389. doi: 10.12461/PKU.DXHX202406032
15. [15]
  Li Jiang , Changzheng Chen , Yang Su , Hao Song , Yanmao Dong , Yan Yuan , Li Li . Electrochemical Synthesis of Polyaniline and Its Anticorrosive Application: Improvement and Innovative Design of the “Chemical Synthesis of Polyaniline” Experiment. University Chemistry, 2024, 39(3): 336-344. doi: 10.3866/PKU.DXHX202309002
16. [16]
  Kexin Dong , Chuqi Shen , Ruyu Yan , Yanping Liu , Chunqiang Zhuang , Shijie Li . Integration of Plasmonic Effect and S-Scheme Heterojunction into Ag/Ag₃PO₄/C₃N₅ Photocatalyst for Boosted Photocatalytic Levofloxacin Degradation. Acta Physico-Chimica Sinica, 2024, 40(10): 2310013-0. doi: 10.3866/PKU.WHXB202310013
17. [17]
  Le Ye , Wei-Xiong Zhang . Structural phase transition in a new organic-inorganic hybrid post-perovskite: (N,N-dimethylpyrrolidinium)[Mn(N(CN)2)3]. Chinese Journal of Structural Chemistry, 2024, 43(6): 100257-100257. doi: 10.1016/j.cjsc.2024.100257
18. [18]
  Xingfen Huang , Jiefeng Zhu , Chuan He . Catalytic enantioselective N-silylation of sulfoximine. Chinese Chemical Letters, 2024, 35(4): 108783-. doi: 10.1016/j.cclet.2023.108783
19. [19]
  Huahong ZHANG , Yang ZHAO , Rui NING , Shuixing WU , Xiaopeng ZHANG . Coordination equilibrium between cyclometalated Pt(Ⅱ) complexs [Pt(κ³-N^C^N′)(CNXyl)]Cl and [Pt(κ²-N^C^N′)(CNXyl)Cl]. Chinese Journal of Inorganic Chemistry, 2025, 41(9): 1840-1850. doi: 10.11862/CJIC.20250136
20. [20]
  Xia ZHANG , Yushi BAI , Xi CHANG , Han ZHANG , Haoyu ZHANG , Liman PENG , Shushu HUANG . Preparation and photocatalytic degradation performance of rhodamine B of BiOCl/polyaniline. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 913-922. doi: 10.11862/CJIC.20240255

Get Citation

PDF

XML

Metrics

PDF Downloads(4)
Abstract views(755)
HTML views(77)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142