高等学校化学学报

高等学校化学学报 ›› 2011, Vol. 32 ›› Issue (11): 2558.

• 研究论文 • 上一篇    下一篇

NaBH4-I2还原法制备N,N'-二甲基间苯二胺

茅佩卿1, 刘立芬1,2,  徐德志1, 李以名1,  高从堦2,3   

  1. 1. 浙江工业大学绿色化学合成技术国家重点实验室培育基地, 杭州 310014;
    2. 浙江大学化学工程与生物工程学系, 杭州 310027;
    3.  杭州水处理技术研究开发中心有限公司, 杭州 310012
  • 收稿日期:2010-12-02 修回日期:2011-03-16 出版日期:2011-11-10 发布日期:2011-10-14
  • 通讯作者: 刘立芬 E-mail:lifenliu@zjut.edu.cn
  • 基金资助:

    国家“九七三”计划项目(批准号:  2009CB623402)和国家自然科学基金(批准号: 21006096)资助.

Synthesis of N,N'-Dimethyl-1,3-benzenediamine by Reduction Method with NaBH4 and I2

MAO Pei-Qing1, LIU Li-Fen1,2*, XU De-Zhi1, LI Yi-Ming1, GAO Cong-Jie2,3   

  1. 1. State Key Laboratory Breeding Base of Green Chemistry-|Synthesis Technology, Zhejiang University of Technology, Hangzhou 310014, China;
    2. Department of Chemical and Biological Engineering, Zhejiang University,  Hangzhou 310027, China;
    3. Hangzhou Development Center of Water Treatment Technology, Hangzhou 310012, China
  • Received:2010-12-02 Revised:2011-03-16 Online:2011-11-10 Published:2011-10-14
  • Contact: LIU Li-Fen E-mail:lifenliu@zjut.edu.cn
  • Supported by:

    国家“九七三”计划项目(批准号:  2009CB623402)和国家自然科学基金(批准号: 21006096)资助.

PDF (PC)

被引次数

9

摘要： 以间苯二胺为原料, 与酰化剂甲酸反应制得中间体N,N'-二甲酰基间苯二胺, 再以NABH4-I2为还原剂合成得到产品N,N'-二甲基间苯二胺, 对合成工艺进行了优化, 并分析了还原机理, 化合物的结构经IR, 1H NMR和MS分析确定. 该法原料易得, 反应条件要求低, 收率高且成本更低.

关键词: N,N'-二甲基间苯二胺, 甲酸, N,N'-二甲酰基间苯二胺, NaBH4-I2

Abstract: The common aromatic polyamide composite reverse osmosis(RO) membrane is easy to be oxidated. N,N'-Dimethyl-1,3-benzenediamine(DMMPD)as a key functional monomer can be used to prepare the chlorine resistance RO membrane by interfacial polymerization technology.  In this work, the DMMPD was synthesized by reduction method with composite reductant NaBH4-I2. The m-phenylenediamine as substrate was first reacted with the acylating agent of formic acid to get the intermediate N,N'-diformyl-m-phenylenediamine, then the resulting intermediate was reduced by NaBH4-I2 to obtain the final product DMMPD, the synthetic technology was further optimized through orthogonal test, and the proposed mechanism of reduction was discussed. The chemical structures of all products were identified via infrared spectra(IR), hydrogen nuclear magnetic resonance(1H  NMR) and mass spectragraph(MS). This current method for preparing the DMMPD has several advantages, including accessible substrate, mild reaction condition, relatively low cost and high yield.

Key words: N,N'-Dimethyl-m-phenylenediamine, Formic acid, N,N'-Diformyl-m-phenylenediamine, NaBH4-I2

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