Synthesis of 4,4'-diamino-1,1'-dianthraquinone-3,3'-disulfonic acid in organic solvent systems

doi:10.11949/j.issn.0438-1157.20161009

CIESC Journal ›› 2017, Vol. 68 ›› Issue (1): 146-153.DOI: 10.11949/j.issn.0438-1157.20161009

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Synthesis of 4,4'-diamino-1,1'-dianthraquinone-3,3'-disulfonic acid in organic solvent systems

ZHANG Tianyong^1,2,3, ZHU Shaodi¹, LI Bin^1,2,3, LIU Qian¹, HAI Li¹, ZHANG Guanghui¹, ZHANG Xia¹, LÜ Dongjun⁴

1 Tianjin Key Laboratory of Applied Catalysis Science and Technology, School of Chemical Engineering and Technology, Tianjin University, Tianjin 300354, China;
2 Collaborative Innovation Center of Chemical Science and Engineering(Tianjin), Tianjin 300354, China;
3 Tianjin Engineering Research Center of Functional Fine Chemicals, Tianjin 300354, China;
4 Shandong Yuhong New Pigment Co. Ltd., Dezhou 253000, Shandong, China

Received:2016-07-18 Revised:2016-10-11 Online:2017-01-05 Published:2017-01-05
Contact: 10.11949/j.issn.0438-1157.20161009
Supported by:
supported by the National Natural Science Foundation of China (21276187), the Natural Science Foundation of Tianjin (16JCYBJC20800) and the Tianjin Science and Technology Innovation Platform Program (14TXGCCX00017).

有机溶剂中合成4,4'-二氨基-1,1'-联蒽醌-3,3'-二磺酸

张天永^1,2,3, 朱少迪¹, 李彬^1,2,3, 刘茜¹, 海莉¹, 张光辉¹, 张夏¹, 吕东军⁴

1 天津大学化工学院, 天津市应用催化科学与工程重点实验室, 天津 300354;
2 天津化学化工协同创新中心, 天津 300354;
3 天津市功能精细化学品技术工程中心, 天津 300354;
4 山东宇虹新颜料股份有限公司, 山东德州 253000

通讯作者: 李彬
基金资助:
国家自然科学基金项目（21276187）；天津市自然科学基金项目（16JCYBJC20800）；天津市科技创新平台计划项目（14TXGCCX00017）。

Abstract

Abstract:

Organic solvent systems for synthesizing 4,4'-diamino-1,1'-dianthraquinone-3,3'-disulfonic acid(DAS) by Ullmann coupled reaction were investigated.Organic solvent can be recycled to avoid significant emissions of acidic and salty wastewater produced in the industrial synthetic methods.The effects of different kinds of single solvents, mixed solvent with different composition and proportion were studied.The results showed that the mixed solvent system of DMF:methanol=1:2 was the best.The experiments to find out the optimal factors such as reaction time, temperature were conducted.The influence of additives and different particle sizes of copper powder was researched.The results indicated that the cation exchange resin can improve the content and yield of DAS and can be easily separated from the reaction system.The copper powder(23 μm) was optimal with the best catalytic performance.The highest content and yield of DAS was 91.56% and 88.43%, respectively.

Key words: bromamine acid, solvent, Ullmann coupled reaction, synthesis, catalysis, cation exchange resin, copper powder

摘要：

研究了在有机溶剂体系中催化溴氨酸进行Ullmann偶联反应合成4，4'-二氨基-1，1'-联蒽醌-3，3'-二磺酸（DAS）的工艺。有机溶剂可回收利用，大大减少了工业生产技术中含酸含盐废水的排放，并降低处理费用。考察了单一溶剂、不同组成和比例的混合溶剂对Ullmann偶联反应的影响，确定最优的溶剂体系为DMF：甲醇=1：2的混合溶剂；研究了最优溶剂体系下的反应时间、温度等因素的影响。对不同添加剂和铜粉粒径对反应的影响进行研究，阳离子交换树脂为最佳添加剂，23 μm铜粉催化效果最优。所得DAS的含量最高为91.56%，收率最高为88.43%。

关键词: 溴氨酸, 溶剂, Ullmann偶联反应, 合成, 催化, 阳离子交换树脂, 铜粉

CLC Number:

ZHANG Tianyong, ZHU Shaodi, LI Bin, LIU Qian, HAI Li, ZHANG Guanghui, ZHANG Xia, LÜ Dongjun. Synthesis of 4,4'-diamino-1,1'-dianthraquinone-3,3'-disulfonic acid in organic solvent systems[J]. CIESC Journal, 2017, 68(1): 146-153.

张天永, 朱少迪, 李彬, 刘茜, 海莉, 张光辉, 张夏, 吕东军. 有机溶剂中合成4,4'-二氨基-1,1'-联蒽醌-3,3'-二磺酸[J]. 化工学报, 2017, 68(1): 146-153.

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Synthesis of 4,4'-diamino-1,1'-dianthraquinone-3,3'-disulfonic acid in organic solvent systems

有机溶剂中合成4,4'-二氨基-1,1'-联蒽醌-3,3'-二磺酸

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