Home

Citation: YI Wen-Bin, CAI Chun. Friedel-Crafts Acylation in Fluorous Biphasic Systems Catalyzed by Rare Earth(Ⅲ) Perfluorooctanesulfonates[J]. Chinese Journal of Applied Chemistry, ;2005, 22(11): 1187-1191. shu

Friedel-Crafts Acylation in Fluorous Biphasic Systems Catalyzed by Rare Earth(Ⅲ) Perfluorooctanesulfonates

YI Wen-Bin ,
CAI Chun ^,

1.
Chemical Engineering College, Nanjing University of Science & Technology, Nanjing 210094

Corresponding author: CAI Chun,
Received Date: 29 December 2004
Available Online: 16 March 2005
Fund Project: 国防科工委"十五"预研基金资助项目(40406020103) (40406020103)

The catalysts of rare earth(Ⅲ) perfluorooctanesulfonates(RE(OSO₂C₈F₁₇)₃,RE=Sc,Y,La~Lu) had been prepared and Friedel-Crafts acylation anisole with Ac₂O on RE(OSO₂C₈F₁₇)₃ catalysts in fluorous biphasic systems were investigated.Perfluorohexane(C₆F₁₄),perfluoromethylcyclohexane(C₇F₁₄),perfluorotoluene(C₇F₈),perfluoro-octane(C₈F₁₈),perfluorooctyl bromide(C₈F₁₇Br) and perfluorodecalin(C₁₀F₁₈,cis and trans-mixture) can be used as fluorous solvents for this reaction.Effects of the ratio of fluorous phase/organic phase and different acylation agents on the reaction were studied.The results show that the reaction exhibits a high para-selectivity of the acylation;Y(OSO₂C₈F₁₇)₃ and C₁₀F₁₈ are the best catalyst and fluorous solvent respectively.The yield of Friedel-Crafts acylation of anisole with Ac₂O was 56% by using Y(OSO₂C₈F₁₇)₃ as the catalyst and C₁₀F₁₈ as the fluorous solvent,and para-selectivity exceeded 99%.By simple phase-separation,the catalytic activity showed a small drop after the fluorous phase containing only the catalyst was re-utilized for five times.
- fluorous biphasic catalysis,
- rare earth(Ⅲ) perfluorooctanesulfonate,
- perfluorocarbons,
- Friedel-Crafts acylation
1. [1]
  Shiyan Cheng , Yonghong Ruan , Lei Gong , Yumei Lin . Research Advances in Friedel-Crafts Alkylation Reaction. University Chemistry, 2024, 39(10): 408-415. doi: 10.12461/PKU.DXHX202403024
2. [2]
  Lixing ZHANG , Yaowen WANG , Xu HAN , Junhong ZHOU , Jinghui WANG , Liping LI , Guangshe LI . Research progress in the synthesis of fluorine-containing perovskites and their derivatives. Chinese Journal of Inorganic Chemistry, 2025, 41(9): 1689-1701. doi: 10.11862/CJIC.20250007
3. [3]
  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
4. [4]
  Shahua Huang , Xiaoming Guo , Lin Lin , Guangping Chang , Sheng Han , Zuxin Zhou . Application of “Integration of Industry and Education” in Engineering Chemistry: Improvement of the Pesticide Fipronil Production. University Chemistry, 2024, 39(3): 199-204. doi: 10.3866/PKU.DXHX202309064
5. [5]
  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
6. [6]
  Tingting Yu , Si Chen , Lianglong Sun , Tongtong Shi , Kai Sun , Xin Wang . Comprehensive Experimental Design for the Photochemical Synthesis, Analysis, and Characterization of Difluoropyrroles. University Chemistry, 2024, 39(11): 196-203. doi: 10.3866/PKU.DXHX202401022
7. [7]
  Yang Chen , Peng Chen , Yuyang Song , Yuxue Jin , Song Wu . Application of Chemical Transformation Driven Impurity Separation in Experiments Teaching: A Novel Method for Purification of α-Fluorinated Mandelic Acid. University Chemistry, 2024, 39(6): 253-263. doi: 10.3866/PKU.DXHX202310077
8. [8]
  Benhua Wang , Chaoyi Yao , Yiming Li , Qing Liu , Minhuan Lan , Guipeng Yu , Yiming Luo , Xiangzhi Song . 一种基于香豆素氟离子荧光探针的合成、表征及性能测试——“科研反哺教学”在有机化学综合实验教学中的探索与实践. University Chemistry, 2025, 40(6): 201-209. doi: 10.12461/PKU.DXHX202408070
9. [9]
  Hui-Ying Chen , Hao-Lin Zhu , Pei-Qin Liao , Xiao-Ming Chen . Integration of Ru(Ⅱ)-Bipyridyl and Zinc(Ⅱ)-Porphyrin Moieties in a Metal-Organic Framework for Efficient Overall CO₂ Photoreduction. Acta Physico-Chimica Sinica, 2024, 40(4): 2306046-0. doi: 10.3866/PKU.WHXB202306046
10. [10]
  Binbin Liu , Yang Chen , Tianci Jia , Chen Chen , Zhanghao Wu , Yuhui Liu , Yuhang Zhai , Tianshu Ma , Changlei Wang . Hydroxyl-functionalized molecular engineering mitigates 2D phase barriers for efficient wide-bandgap and all-perovskite tandem solar cells. Acta Physico-Chimica Sinica, 2026, 42(1): 100128-0. doi: 10.1016/j.actphy.2025.100128
11. [11]
  Tianyun Chen , Ruilin Xiao , Xinsheng Gu , Yunyi Shao , Qiujun Lu . Synthesis, Crystal Structure, and Mechanoluminescence Properties of Lanthanide-Based Organometallic Complexes. University Chemistry, 2024, 39(5): 363-370. doi: 10.3866/PKU.DXHX202312017
12. [12]
  Min WANG , Dehua XIN , Yaning SHI , Wenyao ZHU , Yuanqun ZHANG , Wei ZHANG . Construction and full-spectrum catalytic performance of multilevel Ag/Bi/nitrogen vacancy g-C₃N₄/Ti₃C₂T_x Schottky junction. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1123-1134. doi: 10.11862/CJIC.20230477
13. [13]
  Jiahui YU , Jixian DONG , Yutong ZHAO , Fuping ZHAO , Bo GE , Xipeng PU , Dafeng ZHANG . The morphology control and full-spectrum photodegradation tetracycline performance of microwave-hydrothermal synthesized BiVO₄:Yb³⁺,Er³⁺ photocatalyst. Journal of Fuel Chemistry and Technology, 2025, 53(3): 348-359. doi: 10.1016/S1872-5813(24)60514-1
14. [14]
  Min WANG , Dehua XIN , Wei ZHANG , Haiying YANG , Yuchun WANG , Zhaorong LIU , Meng SHI , Le SHI . Preparation and full-spectrum catalytic degradation performance of nitrogen vacancy g-C₃N₄/Bi/BiOBr/BiOI heterojunction material. Chinese Journal of Inorganic Chemistry, 2025, 41(11): 2283-2298. doi: 10.11862/CJIC.20250109
15. [15]
  Jinhui Jiang , Jiaqi Sun , Yongyi Chen , Lei Zhang , Pengyu Dong . W₁₈O₄₉/Al-doped SrTiO₃ S-scheme heterojunction aided by the LSPR effect for full-spectrum solar light-driven photocatalytic hydrogen evolution. Acta Physico-Chimica Sinica, 2025, 41(11): 100145-0. doi: 10.1016/j.actphy.2025.100145
16. [16]
  Zhuomin Zhang , Lanrui Yang , Baorong Zhang , Gongke Li . 化学分析全英课程思政建设初探. University Chemistry, 2025, 40(8): 58-65. doi: 10.12461/PKU.DXHX202410010
17. [17]
  Haiyang Guo , Longfeng Zhu , Wei Zhong , Lianwen Zhu , Lei Li . Practice and Exploration of English-Teaching for Inorganic Chemistry in Regional Universities. University Chemistry, 2025, 40(10): 54-62. doi: 10.12461/PKU.DXHX202411016
18. [18]
  Zhonghong Yan , Chunxia Li , Ruolin Yang . Analysis of the Use and Effectiveness of Concept Mapping Assignments in English Medium Instruction of General Chemistry. University Chemistry, 2025, 40(4): 224-231. doi: 10.12461/PKU.DXHX202405138
19. [19]
  Weizhi Wang , Jieling Qin , Jie Cao . 仪器分析全英语课程设置的必要性与思政教育实践融合. University Chemistry, 2025, 40(8): 117-123. doi: 10.12461/PKU.DXHX202410067
20. [20]
  Hui Wang , Yiwen Zhang , Dong Liu . “三全育人”理念下培养应用型创新人才——以“赛教结合”模式为例的探索与实践. University Chemistry, 2025, 40(6): 37-42. doi: 10.12461/PKU.DXHX202407091

Get Citation

PDF

XML

Metrics

PDF Downloads(1)
Abstract views(393)
HTML views(24)

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