Journal of Liaoning Petrochemical University

Journal of Liaoning Petrochemical University ›› 2017, Vol. 37 ›› Issue (2): 5-9.DOI: 10.3969/j.issn.1672-6952.2017.02.002

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Acylation Reaction on the 2-Methoxynaphthalene Catalyzed by Pyridine-Toluene-p-Sulfonic Acid Functionalized  Ionic  Liquid

  

  1. College of Chemistry & Material Science Engineering,Liaoning Shihua University,Fushun Liaoning 113001,China
  • Received:2016-09-07 Published:2017-04-20 Online:2017-05-04

吡啶-对甲苯磺酸功能化离子液体催化2-萘甲醚的酰化

陈少奇,陈 平,兰 鲲   

  1. 辽宁石油化工大学 化学与材料科学学院,辽宁 抚顺 113001
  • 通讯作者: 陈平(1963-),女,博士,教授,从事有机催化研究;E-mail:chenping-fs@sohu.com。
  • 作者简介:陈少奇(1996-),男,本科生,化学工程与工艺专业,从事有机催化研究;E-mail:2210704148@qq.com。
  • 基金资助:
    辽宁省自然科学基金项目(2015020196); 辽宁省大学生创新创业项目(201510148047)。

Abstract:

    Pyridine-sulfonic acid functionalized ionic liquid([PY-BS] [TsO]) is prepared by the reaction of p-toluenesulfonic acid with sulfonic groups amphoteric salt(PY-BS) that is prepared by the reaction of Pyridine with 1,4butyl sultone. Then, [PY-BS][TsO] ionic liquid can be characterized by IR, NMR. And it is chosen as the catalyst and solvent in the Friedel-Craft acylation of 2-methoxynaphthalene optimizing the reaction conditions by orthogonal experiment of L9(34). The orthogonal experiment result shows that the conversion of 2-methoxynaphthalene (2-MN) reaches 90.7% and the selectivity of 2-methoxy-1-acetyl naphthalene as the main products is 99.4% in the follwing conditions that the 2methoxynaphthalene is 5 mmol, the mol ratio of 2-methoxynaphthalene/acetic anhydride is 15, ionic liquid is 0.3 g and reaction time is 6.0 h at 120 . The main factors affecting the reaction rate and product selectivity are the reaction time and temperature.

Key words: Ionic liquid,   2-Methoxynaphthalene,    , Friedel-craft  , acylation,     , Catalyst,    , Orthogonal  , experiment

摘要:         吡啶与1,4-丁基磺内酯反应首先制备具有磺酸基团的两性盐,然后再与对甲苯磺酸反应合成吡啶-磺酸功能化离子液体,通过核磁共振(NMR)和红外光谱(IR)表征其结构。该离子液体作为催化剂及溶剂,催化2-萘甲醚的乙酰基化反应,设计正交试验L9(34)优化其反应件。结果表明,2-萘甲醚的物质的量为5mmol、2-萘甲醚/乙酸酐的物质的量比为1∶5,离子液体质量0.3g,120℃下反应6.0h,2-萘甲醚的转化率达90.7%。主产物2-甲氧基-1-萘乙酮的选择性为99.4%;其中,影响反应物转化率和产物选择性的主要因素为反应时间和温度。

关键词: 离子液体, 2-萘甲醚,    , F-C酰基化,    , 催化,    ,  正交试验

Cite this article

Chen Shaoqi,Chen Ping,Lan Kun. Acylation Reaction on the 2-Methoxynaphthalene Catalyzed by Pyridine-Toluene-p-Sulfonic Acid Functionalized  Ionic  Liquid[J]. Journal of Liaoning Petrochemical University, 2017, 37(2): 5-9.

陈少奇,陈 平,兰 鲲. 吡啶-对甲苯磺酸功能化离子液体催化2-萘甲醚的酰化[J]. 辽宁石油化工大学学报, 2017, 37(2): 5-9.