Synthesis of 2,3,3',4'-Biphenyltetracarboxylic Dianhydride

doi:10.11944/j.issn.1000-0518.2016.08.150401

Chinese Journal of Applied Chemistry ›› 2016, Vol. 33 ›› Issue (8): 900-904.DOI: 10.11944/j.issn.1000-0518.2016.08.150401

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Synthesis of 2,3,3',4'-Biphenyltetracarboxylic Dianhydride

LI Yuhan^a,WU Qiang^b,KANG Chuanqing^b,GUO Haiquan^b,JIN Rizhe^b^*(),GAO Lianxun^b

^a Branch of Food Engineering,Jilin Business and Technology College,Changchun 130507,China
^b Changchun Institute of Applied Chemistry,Chinese Academy of Sciences,Changchun 130022,China

Received:2015-11-16 Accepted:2016-03-02 Published:2016-07-21 Online:2016-07-21
Contact: JIN Rizhe
Supported by:
Supported by the National Program on Key Basic Research Project(973 Program)(No.2014CB643603), the Jilin Technology R&D Program(No.20140203003GX), Science Foundation of Jilin Province(No.20130101005JC)

Abstract

Abstract:

A facile synthesis of 2,3,3',4'-biphenyltetracarboxylic dianhydride through cross-coupling of halo-substituted orthoxylene and liquid-phase oxidation of the resulted tetramethylbiphenyl. 2,3,3',4'-Tetramethylbiphenyl(3,4'-TMDP) was synthesized by cross-coupling of 4-bromo-1,2-dimethylbenzene and 3,4-dimethylphenylmagnesium bromide with NiF₂-PPh₃(PPh₃:triphenylphosphine) as the catalyst and which was then converted to 2,3,3',4'-biphenyltetracarboxylic dianhydride(3,4'-BPDA) by the oxidation and dehydration procedures. The overall yield reached to 74%. In comparison with the preparations of 3,4'-BPDA from dimethyl phthalate or chlorinated dimethyl phthalate mixture, the method exhibits advantages in the separation and environmental benign because of the avoidance of the tedious hydrolysis step and the separation of isomers.

Key words: biphenyltetracarboxylic dianhydride, synthesis, cross-coupling, polyimide

LI Yuhan, WU Qiang, KANG Chuanqing, GUO Haiquan, JIN Rizhe, GAO Lianxun. Synthesis of 2,3,3',4'-Biphenyltetracarboxylic Dianhydride[J]. Chinese Journal of Applied Chemistry, 2016, 33(8): 900-904.

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Synthesis of 2,3,3',4'-Biphenyltetracarboxylic Dianhydride

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