Research progress of 1,5- diaminonaphthalene synthesis

doi:10.16085/j.issn.1000-6613.2021-2310

Abstract

Abstract:

1,‍5-Diaminonaphthalene is an important chemical raw material. This paper first briefly introduced the synthesis of 1,‍5-diaminonaphthalene by halogenated amination, naphthol ammonolysis, cyclization, and other processes. The emphasis was put on the traditional industrial nitration reduction method. Then, the research progress of nitration reaction stage was described from "strong acid mixed acid" system to "non-acid" system, and that of the reduction reaction stage from precious metal catalysts to non-precious metal catalysts, from the perspectives of green chemistry and intrinsic safety. Moreover, it was pointed out that the reduction reaction stage of the nitrification reduction method is relatively green and environmental-friendly, while the nitrification reaction stage is still not. The overall processes is complicated. Based on the above-mentioned problems including environmental pollution, and low efficiency, the latest research progress on one-step synthesis of 1,5-diaminonaphthalene from naphthalene and with ammonia or hydroxylamine salt as aminating agents, was further discussed. In summary, the clean and efficient one-step synthesis of naphthylamine under mild conditions would become a research direction in the future.

Key words: 1,5-diaminonaphthalene, nitration, reduction, hydrogenation, catalyst, amination

摘要：

1,5-二氨基萘是一种重要的化工原料。本文首先简要介绍了合成1,5-二氨基萘的卤代氨化、二萘酚氨解、环合等生产方法；并以工业上经典的硝化还原法制备1,5-二氨基萘反应为重点，从绿色化学和本质安全角度出发，对硝化反应阶段从“强酸混酸”至“非酸”体系，以及还原反应阶段从贵金属催化剂至非贵金属催化剂的研究进展分别进行了阐述。同时指出硝化还原法的还原反应阶段相对比较绿色、环保，但硝化反应阶段仍然存在环境不友好的问题，且整体工艺流程烦琐复杂。针对上述合成工艺中普遍存在的环境污染、效率低等不足之处，进一步讨论了以氨水、羟胺盐等为胺化剂，由萘一步合成1,5-二氨基萘的最新研究进展，并指出温和条件下、清洁高效的一步合成萘胺将成为今后的研究方向。

关键词: 1,5-二氨基萘, 硝化, 还原, 加氢, 催化剂, 胺化

CLC Number:

TQ246.3

CHENG Peng, ZHAO Shanshan, YANG Wenlong, QI Yue, DING Xiaoshu, YANG Qiusheng, ZHANG Dongsheng, WANG Yanji. Research progress of 1,5- diaminonaphthalene synthesis[J]. Chemical Industry and Engineering Progress, 2022, 41(9): 5011-5021.

程鹏, 赵山山, 杨文龙, 齐跃, 丁晓墅, 杨秋生, 张东升, 王延吉. 1,5-二氨基萘合成技术研究进展[J]. 化工进展, 2022, 41(9): 5011-5021.

Figures/Tables 14

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序号	催化剂	反应条件	产物	（转化率/选择性）/%	参考文献
1	20%Ni/CNTs-1	DMF， 120℃， 330min， 0.6MPa	1,5-二氨基萘	100/92.0	［38］
2	10%Ni/C	THF， 320℃， 360min， 5.2MPa	1,5-二氨基萘	96.6/2.4	［39］
3	10%Ni-Zn/AC-350	DMF， 110℃， 300min， 0.6MPa	1,5-二氨基萘	100/95.6	［42］
4	20%Ni/N-AC-800	DMF， 100℃， 300min， 0.6MPa	1,5-二氨基萘	100/94.8	［40］
5	20%Ni/N，P-AC-900	DMF， 100℃， 150min， 0.6MPa	1,5-二氨基萘	100/95.8	［41］

序号	催化剂	反应条件	产物	（转化率/选择性）/%	参考文献
1	20%Ni/CNTs-1	DMF， 120℃， 330min， 0.6MPa	1,5-二氨基萘	100/92.0	［38］
2	10%Ni/C	THF， 320℃， 360min， 5.2MPa	1,5-二氨基萘	96.6/2.4	［39］
3	10%Ni-Zn/AC-350	DMF， 110℃， 300min， 0.6MPa	1,5-二氨基萘	100/95.6	［42］
4	20%Ni/N-AC-800	DMF， 100℃， 300min， 0.6MPa	1,5-二氨基萘	100/94.8	［40］
5	20%Ni/N，P-AC-900	DMF， 100℃， 150min， 0.6MPa	1,5-二氨基萘	100/95.8	［41］

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