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

Chem. J. Chinese Universities ›› 2011, Vol. 32 ›› Issue (11): 2558.

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

MAO Pei-Qing¹, LIU Li-Fen^1,2*, XU De-Zhi¹, LI Yi-Ming¹, GAO Cong-Jie^2,3

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.

Abstract

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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MAO Pei-Qing, LIU Li-Fen*, XU De-Zhi, LI Yi-Ming, GAO Cong-Jie. Synthesis of N,N'-Dimethyl-1,3-benzenediamine by Reduction Method with NaBH4 and I2[J]. Chem. J. Chinese Universities, 2011, 32(11): 2558.

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

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