Home

Citation: ZHAO Xin, YU Hui-Li, GE Ji-Yun. Regioselective Nitration of Toluene in Ionic Liquid Caprolactam-trifluoromethanesulfonic Acid[J]. Chinese Journal of Applied Chemistry, ;2009, 26(8): 905-908. shu

Regioselective Nitration of Toluene in Ionic Liquid Caprolactam-trifluoromethanesulfonic Acid

1.
School of Chemistry and Bioengineering, Suzhou University of Science and Technology, Suzhou 215011

Corresponding author: ZHAO Xin,
Received Date: 16 July 2008
Available Online: 29 September 2008
Fund Project: 建设部科研基金资助项目(2008-K7-29) (2008-K7-29)

A novel ionic liquid(IL) caprolactam-trifluoromethanesulfonic acid([CP]OTf) was prepared with trifluoromethanesulfonic acid and caprolactam as raw materials.The structure of the IL was characterized by ¹H NMR and FTIR,and was used as the catalyst and solvent in the nitration of toluene.The effects of the amount of catalyst,reaction temperature,reaction time,concentration of nitric acid and catalyst recycling on the yield and para-selectivity for the nitration of toluene were investigated with the aid of gas chromatography.The results show that when the nitration temperature was 55 ℃,the reaction time was 6 h,the molar ratio of toluene to 95% nitric acid was 1:1,the amount of catalyst was 15% of the molar amount of toluene,the ortho-para isomer ratio reached 1.12,far below 1.67 by using sulfuric acid,and gave a product yield of 78.41%.IL([CP]OTf) showed high regioselectivity and catalytic activity.The catalyst could be reutilized up to five times with little decrease in activity and regioselectivity.
- toluene,
- ionic liquid,
- nitration,
- caprolactam-trifluoromethanesulfonic acid
1. [1]
  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
2. [2]
  Qiang Zhang , Yuanbiao Huang , Rong Cao . Imidazolium-Based Materials for CO₂ Electroreduction. Acta Physico-Chimica Sinica, 2024, 40(4): 2306040-0. doi: 10.3866/PKU.WHXB202306040
3. [3]
  Fei ZHOU , Xiaolin JIA . Co₃O₄/TiO₂ composite photocatalyst: Preparation and synergistic degradation performance of toluene. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2232-2240. doi: 10.11862/CJIC.20240236
4. [4]
  Qiaorong RU . Synthesis and characterization of tripyridine functionalized polyionic liquid luminescent materials. Chinese Journal of Inorganic Chemistry, 2026, 42(1): 111-119. doi: 10.11862/CJIC.20250121
5. [5]
  Yufang GAO , Nan HOU , Yaning LIANG , Ning LI , Yanting ZHANG , Zelong LI , Xiaofeng LI . Nano-thin layer MCM-22 zeolite: Synthesis and catalytic properties of trimethylbenzene isomerization reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1079-1087. doi: 10.11862/CJIC.20240036
6. [6]
  Wenjun Zheng . Application in Inorganic Synthesis of Ionic Liquids. University Chemistry, 2024, 39(8): 163-168. doi: 10.3866/PKU.DXHX202401020
7. [7]
  Hong Zheng , Xin Peng , Chunwang Yi . The Tale of Caprolactam Cyclic Oligomers: The Ever-changing Life of “Princess Cyclo”. University Chemistry, 2024, 39(9): 40-47. doi: 10.12461/PKU.DXHX202403058
8. [8]
  Yuena Yu , Fang Fang . Microwave-Assisted Synthesis of Safinamide Methanesulfonate. University Chemistry, 2024, 39(11): 210-216. doi: 10.3866/PKU.DXHX202401076
9. [9]
  Zhen Li , Sujuan Zhang , Zhongliao Wang , Jinfeng Zhang , Gaoli Chen , Shifu Chen . Rational design of S-scheme CdS/MnO₂ heterojunctions for high-value photothermal synergistic catalytic oxidation of toluene. Acta Physico-Chimica Sinica, 2026, 42(4): 100179-0. doi: 10.1016/j.actphy.2025.100179
10. [10]
  Feiya Cao , Qixin Wang , Pu Li , Zhirong Xing , Ziyu Song , Heng Zhang , Zhibin Zhou , Wenfang Feng . Magnesium-Ion Conducting Electrolyte Based on Grignard Reaction: Synthesis and Properties. University Chemistry, 2024, 39(3): 359-368. doi: 10.3866/PKU.DXHX202308094
11. [11]
  Yingran Liang , Fei Wang , Jiabao Sun , Hongtao Zheng , Zhenli Zhu . Construction and Application of a New Experimental Device for Determination of Alkaline Metal Elements by Plasma Atomic Emission Spectrometry Based on Solution Cathode Glow Discharge: An Alternative Approach for Fundamental Teaching Experiments in Emission Spectroscopy. University Chemistry, 2024, 39(5): 380-387. doi: 10.3866/PKU.DXHX202312024
12. [12]
  Wenjuan Tan , Yong Ye , Xiujuan Sun , Bei Liu , Jiajia Zhou , Hailong Liao , Xiulin Wu , Rui Ding , Enhui Liu , Ping Gao . Building P-Poor Ni₂P and P-Rich CoP₃ Heterojunction Structure with Cation Vacancy for Enhanced Electrocatalytic Hydrazine and Urea Oxidation. Acta Physico-Chimica Sinica, 2024, 40(6): 2306054-0. doi: 10.3866/PKU.WHXB202306054
13. [13]
  Chaolin Mi , Yuying Qin , Xinli Huang , Yijie Luo , Zhiwei Zhang , Chengxiang Wang , Yuanchang Shi , Longwei Yin , Rutao Wang . Galvanic Replacement Synthesis of Graphene Coupled Amorphous Antimony Nanoparticles for High-Performance Sodium-Ion Capacitor. Acta Physico-Chimica Sinica, 2024, 40(5): 2306011-0. doi: 10.3866/PKU.WHXB202306011
14. [14]
  Zhipeng Bao , Yilin Wang , Yu Chen , Beirui Jia , Congcong Wang , Zean Xie , Xuehua Yu , Zhen Zhao . Digital and Intelligent Integration under the “Dual Carbon” Strategy: Plasma Reaction-Separation Coupling for CO₂ Hydrogenation to Methanol. University Chemistry, 2026, 41(1): 29-40. doi: 10.12461/PKU.DXHX202506009
15. [15]
  Xiaoning TANG , Shu XIA , Jie LEI , Xingfu YANG , Qiuyang LUO , Junnan LIU , An XUE . Fluorine-doped MnO₂ with oxygen vacancy for stabilizing Zn-ion batteries. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1671-1678. doi: 10.11862/CJIC.20240149
16. [16]
  Yingchun ZHANG , Yiwei SHI , Ruijie YANG , Xin WANG , Zhiguo SONG , Min WANG . Dual ligands manganese complexes based on benzene sulfonic acid and 2, 2′-bipyridine: Structure and catalytic properties and mechanism in Mannich reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1501-1510. doi: 10.11862/CJIC.20240078
17. [17]
  Mei Yan , Rida Feng , Yerdos·Tohtarkhan , Biao Long , Li Zhou , Chongshen Guo . Expansion and Extension of Liquid Saturated Vapor Measurement Experiment. University Chemistry, 2024, 39(3): 294-301. doi: 10.3866/PKU.DXHX202308103
18. [18]
  Lina Guo , Ruizhe Li , Chuang Sun , Xiaoli Luo , Yiqiu Shi , Hong Yuan , Shuxin Ouyang , Tierui Zhang . Effect of Interlayer Anions in Layered Double Hydroxides on the Photothermocatalytic CO₂ Methanation of Derived Ni-Al₂O₃ Catalysts. Acta Physico-Chimica Sinica, 2025, 41(1): 100002-0. doi: 10.3866/PKU.WHXB202309002
19. [19]
  Vanita Vanita , Roland Schoch , Pascal Puphal , Hasan Yilmaz , Matthias Bauer , Oliver Clemens . Structural and electrochemical behaviour of bilayer manganite LaSr₂Mn₂O_6.96 cathode for all-solid-state fluoride ion batteries. Acta Physico-Chimica Sinica, 2026, 42(3): 100181-0. doi: 10.1016/j.actphy.2025.100181
20. [20]
  Peiran ZHAO , Yuqian LIU , Cheng HE , Chunying DUAN . A functionalized Eu³⁺ metal-organic framework for selective fluorescent detection of pyrene. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 713-724. doi: 10.11862/CJIC.20230355

Get Citation

PDF

XML

Metrics

PDF Downloads(1)
Abstract views(879)
HTML views(134)

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

Address：Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888

DownLoad: Full-Size Img PowerPoint

Return