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酸性功能化离子液体催化“一锅法”合成酰胺烷基萘酚
引用本文:佘婷婷,刘祖亮,巩凯. 酸性功能化离子液体催化“一锅法”合成酰胺烷基萘酚[J]. 应用化学, 2010, 27(7): 778-782. DOI: 10.3724/SP.J.1095.2010.90549
作者姓名:佘婷婷  刘祖亮  巩凯
作者单位:(南京理工大学化工学院 南京 210094)
摘    要:用磺酸型离子液体1-甲基-3-磺酸丙基咪唑硫酸氢盐([MIMPS][HSO4])催化β-萘酚、芳香醛和酰胺(或脲)3组分“一锅法” 类Ritter反应合成了酰胺烷基萘酚。 投料比为n(β-萘酚)∶n(芳香醛)∶n(酰胺或脲)∶n([MIMPS][HSO4])=1∶1∶1.3∶0.1,无需溶剂,恒温125 ℃反应5~40 min,通过简单水洗抽滤即可分离产物,酰胺烷基萘酚产率为85%~97%。 离子液体[MIMPS][HSO4]可回收重复使用4次,其催化活性无明显降低。 探讨了醛、酰胺或脲结构对反应的影响及可能的反应机理。

关 键 词:酸性功能化离子液体  类Ritter反应  芳香醛  酰胺  酰胺烷基萘酚  
收稿时间:2009-08-24
修稿时间:2009-11-12

Synthesis of Amidoalkyl Naphthols:"One-pot" Reaction Catalyzed by Sulfonic Acid Ionic Liquid
SHE Ting-Ting,LIU Zu-Liang,GONG Kai. Synthesis of Amidoalkyl Naphthols:"One-pot" Reaction Catalyzed by Sulfonic Acid Ionic Liquid[J]. Chinese Journal of Applied Chemistry, 2010, 27(7): 778-782. DOI: 10.3724/SP.J.1095.2010.90549
Authors:SHE Ting-Ting  LIU Zu-Liang  GONG Kai
Affiliation:(School of Chemical Engineering,Nanjing University of Science & Technology,Nanjing 210094)
Abstract:An efficient one pot synthesis of amidoalkyl naphthols is described. This involves the three-component Ritter-type reaction of β-naphthol, aromatic aldehyde and amide or urea catalyzed by sulfonic ionic liquid, 1-methyl-3-propanesulfonic acid immidazolium hydrogen sulfate [MIMPS][HSO4]. The results show that under solvent free condition at 125 ℃ and n(β-naphthol)∶n(aromatic aldehyde)∶n(amide or urea)∶n([MIMPS][HSO4])=1∶1∶1.3∶0.1 for 5~40 min, the yield of amidoalkyl naphthols was 85%~97%. The product could be separated simply by filtration after the reaction. The ionic liquid was recycled four times without apparent decrease in catalytic activity. The factors which influenced the multi-component reaction were discussed including the structure of aromatic aldehyde and amide or urea. A possible mechanism was postulated as well.
Keywords:acidic functionalized ionic liquid  Ritter-analog reaction  aromatic aldehydes  amide  amidoalkyl naphthols
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