4,5-二氨基-2-羟基苯甲酸的合成工艺

doi:10.16085/j.issn.1000-6613.2017.03.039

化工进展 ›› 2017, Vol. 36 ›› Issue (03): 1059-1066.DOI: 10.16085/j.issn.1000-6613.2017.03.039

4,5-二氨基-2-羟基苯甲酸的合成工艺

何威威¹, 金宁人¹, 陈汉庚², 毛婷婷¹

1 浙江工业大学化学工程学院, 浙江杭州 310032;
2 鼎龙化工集团公司, 浙江杭州 310005

收稿日期:2016-08-25 修回日期:2016-10-06 出版日期:2017-03-05 发布日期:2017-03-05
通讯作者: 金宁人,教授。
作者简介:何威威(1992-),男,硕士研究生。E-mail:hww@zjut.edu.cn。
基金资助:
江苏省科技支撑计划项目（BE2011129）。

Research on synthesis of 4,5-diamino-2-hydroxybenzoic acid

HE Weiwei¹, JIN Ningren¹, CHEN Hangeng², MAO Tingting¹

1 College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310032, Zhejiang, China;
2 Dragon Chemicals group Co., Ltd., Hangzhou 310005, Zhejiang, China

Received:2016-08-25 Revised:2016-10-06 Online:2017-03-05 Published:2017-03-05

摘要/Abstract

摘要：

以对氨基水杨酸（ASA）为原料先经酰化、硝化和水解制备关键中间体4-氨基-2-羟基-5-硝基苯甲酸（AHNA），然后硝基还原合成聚苯并咪唑新单体4，5-二氨基-2-羟基苯甲酸（DAHBA）。结果表明：ASA在乙酸中先后用乙酐进行酰化和用HNO₃硝化、20～30℃各反应3h，获得收率为70.9%、纯度为97.28%的4-乙酰胺基-2-羟基-5-硝基苯甲酸（AHNBA）；AHNBA在盐酸水溶液中，水解回流反应4h，制得关键中间体AHNA，其收率为79.5%、纯度99.21%；以水为溶剂，AHNA在Pd/C催化下水合肼回流还原30min合成出DAHBA，收率为55.3%、纯度98.84%。产物的分子结构经过FTIR、¹H NMR、¹³C NMR、ESI-MS等表征与确认，为提高聚对苯撑苯并二（口恶）唑（PBO）的复合粘结、轴向抗压和耐光性能提供关键共聚单体的技术与来源。

关键词: 4, 5-二氨基-2-羟基苯甲酸, 有机化合物, 4-氨基-2-羟基-5-硝基苯甲酸, 聚对苯撑苯并二（口恶）唑, 合成

Abstract:

In this paper,the key intermediate 4-amino-2-hydroxy-5-nitro benzoic acid(AHNA) was successfully synthesized by the acylation reaction of 4-aminosalicylic acid(ASA),then nitration and acid hydrolysis. A new polybenzimidazole monomer 4,5-diamino-2-hydroxybenzoic acid(DAHBA) was prepared by the reduction reaction of AHNA. The results showed that,using acetic acid as solvent,after ASA was first acylated with acetic anhydride and then nitrated with nitric acid for 3 hours,4-acetamido-2-hydroxy-5-nitro benzoic acid(AHNBA) was obtained with the total yield of 70.9% and the purity of 97.28%. The key intermediate AHNA was synthesized by the acid hydrolysis of AHNBA for 4 hours at reflux. AHNA was obtained with the yield of 79.5% and the purity of 99.21%. DAHBA of 98.84% purity was obtained by reduction of AHNA using hydrazine hydrate,Pd/C and reflux 30min in the water with the yield of 55.3%. The structure of DAHBA was identified by FTIR, ¹H NMR,¹³C NMR,and ESI-MS. Meanwhile,it could also provide the key monomer and technical source for the synthesis of the HI-PBO fiber with good performance of composite adhesiveness,axial compressive and light resistance.

Key words: 4,5-diamino-2-hydroxybenzoic acid, organic compound, 4-amino-2-hydroxy-5-nitrobenzoic acid, poly-p-phenylene benzobisoxazole, synthesis

中图分类号:

TQ316.342

何威威, 金宁人, 陈汉庚, 毛婷婷. 4,5-二氨基-2-羟基苯甲酸的合成工艺[J]. 化工进展, 2017, 36(03): 1059-1066.

HE Weiwei, JIN Ningren, CHEN Hangeng, MAO Tingting. Research on synthesis of 4,5-diamino-2-hydroxybenzoic acid[J]. Chemical Industry and Engineering Progress, 2017, 36(03): 1059-1066.

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4,5-二氨基-2-羟基苯甲酸的合成工艺

Research on synthesis of 4,5-diamino-2-hydroxybenzoic acid

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