引用本文:
焦岩, 方志杰, 姜宇华, 郑保辉. 制备2,2',4,4'-联苯四甲酸的新方法[J]. 应用化学,
2007, 24(7): 844-846.
Citation: JIAO Yan, FANG Zhi-Jie, JIANG Yu-Hua, ZHENG Bao-Hui. A Novel Synthetic Method for 2,2',4,4'-Tetra Carboxylic Acid Biphenyl[J]. Chinese Journal of Applied Chemistry, 2007, 24(7): 844-846.
Citation: JIAO Yan, FANG Zhi-Jie, JIANG Yu-Hua, ZHENG Bao-Hui. A Novel Synthetic Method for 2,2',4,4'-Tetra Carboxylic Acid Biphenyl[J]. Chinese Journal of Applied Chemistry, 2007, 24(7): 844-846.
制备2,2',4,4'-联苯四甲酸的新方法
摘要:
以对甲苯胺为原料研究了2,2',4,4'-联苯四甲酸的新合成路线。首先由对甲苯胺经三步反应制备了2-氨基-5-甲基苯甲酸,对工艺条件进行了优化,明显地减少了试剂的用量,三步收率达61.5%;2-氨基-5-甲基苯甲酸经重氮化反应、重氮盐偶联反应得到4,4'-二甲基-2,2'-联苯二甲酸,NaOH和NH2OH.HCl的摩尔投料比为1:1时偶联反应收率最高可达到88%;在弱碱性条件下以KMnO4氧化二甲基联苯二甲酸得到最终产物,以对甲苯胺计算总收率为43.3%。产物结构经1H NMR和IR测试技术确证。以羧酸芳烃重氮盐为反应物制备联苯四甲酸的工艺路线,反应条件温和,收率较高。
English
A Novel Synthetic Method for 2,2',4,4'-Tetra Carboxylic Acid Biphenyl
Abstract:
A novel method for the synthesis of 2,2',4,4'-tetra carboxylic acid biphenyl with p-methyl aniline as raw material is described in this article.Firstly,2-amino-5-methylbenzoic acid was prepared from p-methyl aniline in three steps with a yield of 61.5%.The process was optimized and the quantities of the reactants were reduced remarkably.Then,4,4'-dimethyl-2,2'-diphenylic acid was obtained by the coupling of diazonium which was made by the diazotization of 2-amino-5-methylbenzoic acid.The effect of molar ratio of NaOH to NH2OH·HCl on the yield was researched.It was found that the maximum yield of 4,4'-dimethyl-2,2'-diphenylic acid was 88% when the molar ratio was 1:1.Finally,the target product 2,2',4,4'-tetra carboxylic acid biphenyl was prepared from the oxidation of 4,4'-dimethyl-2,2'-diphenylic acid by KMnO4 in an alkaline solution.Total yield based on p-methyl aniline was 43.3%.The structure of the product was characterized by 1H NMR and IR (KBr).By using benzoic diazonium as a reactant,this synthetic route for tetra carboxylic biphenyl uses mild reaction condition,with high yields and good industrial application potential.
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Key words:
- aminomethyl benzoic acid
- / tetra carboxylic acid biphenyl
- / synthesis
- / coupling
- / diazonium
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