化工进展 ›› 2022, Vol. 41 ›› Issue (9): 5011-5021.DOI: 10.16085/j.issn.1000-6613.2021-2310
程鹏1(), 赵山山1, 杨文龙1, 齐跃2(), 丁晓墅1, 杨秋生1,3, 张东升1,3(), 王延吉1,3
收稿日期:
2021-11-11
修回日期:
2022-04-07
出版日期:
2022-09-25
发布日期:
2022-09-27
通讯作者:
齐跃,张东升
作者简介:
程鹏(1996—),男,硕士研究生,研究方向为绿色催化过程与工艺。E-mail: champion0806@163.com。
基金资助:
CHENG Peng1(), ZHAO Shanshan1, YANG Wenlong1, QI Yue2(), DING Xiaoshu1, YANG Qiusheng1,3, ZHANG Dongsheng1,3(), WANG Yanji1,3
Received:
2021-11-11
Revised:
2022-04-07
Online:
2022-09-25
Published:
2022-09-27
Contact:
QI Yue, ZHANG Dongsheng
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。
中图分类号:
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.
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.
序号 | 催化剂 | 时间/h | 转化率/% | 收率/% | 异构比 |
---|---|---|---|---|---|
1 | HZSM-5 | 48 | 26 | 41 | 3.51 |
2 | HZSM-5 | 48 | 88 | 37 | 0.59 |
3 | CuZSM-5 | 48 | 85 | 40 | 1.79 |
4 | MgZSM-5 | 48 | 67 | 31 | 0.79 |
5 | CoZSM-5 | 48 | 56 | 41 | 0.82 |
6 | LaZSM-5 | 48 | 50 | 38 | 1.27 |
7 | CdZSM-5 | 48 | 43 | 24 | 0.60 |
8 | CuZSM-5 | 8 | 45 | 37 | 0.69 |
9 | HBEA-25 | 48 | 91 | 65 | 2.57 |
10 | HBEA-280 | 48 | 72 | 49 | 1.39 |
11 | HBEA-500 | 48 | 59 | 53 | 1.27 |
12 | CuBEA-25 | 48 | 37 | 28 | 1.23 |
13 | MgBEA-25 | 48 | 44 | 34 | 0.49 |
14 | CoBEA-25 | 48 | 29 | 52 | 0.64 |
15 | LaBEA-25 | 48 | 38 | 22 | 0.90 |
16 | CdBEA-25 | 48 | 39 | 56 | 0.52 |
表1 不同沸石催化剂下二氧化氮与1-硝基萘的硝化反应[15]
序号 | 催化剂 | 时间/h | 转化率/% | 收率/% | 异构比 |
---|---|---|---|---|---|
1 | HZSM-5 | 48 | 26 | 41 | 3.51 |
2 | HZSM-5 | 48 | 88 | 37 | 0.59 |
3 | CuZSM-5 | 48 | 85 | 40 | 1.79 |
4 | MgZSM-5 | 48 | 67 | 31 | 0.79 |
5 | CoZSM-5 | 48 | 56 | 41 | 0.82 |
6 | LaZSM-5 | 48 | 50 | 38 | 1.27 |
7 | CdZSM-5 | 48 | 43 | 24 | 0.60 |
8 | CuZSM-5 | 8 | 45 | 37 | 0.69 |
9 | HBEA-25 | 48 | 91 | 65 | 2.57 |
10 | HBEA-280 | 48 | 72 | 49 | 1.39 |
11 | HBEA-500 | 48 | 59 | 53 | 1.27 |
12 | CuBEA-25 | 48 | 37 | 28 | 1.23 |
13 | MgBEA-25 | 48 | 44 | 34 | 0.49 |
14 | CoBEA-25 | 48 | 29 | 52 | 0.64 |
15 | LaBEA-25 | 48 | 38 | 22 | 0.90 |
16 | CdBEA-25 | 48 | 39 | 56 | 0.52 |
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 | [ |
2 | 10%Ni/C | THF, 320℃, 360min, 5.2MPa | 1,5-二氨基萘 | 96.6/2.4 | [ |
3 | 10%Ni-Zn/AC-350 | DMF, 110℃, 300min, 0.6MPa | 1,5-二氨基萘 | 100/95.6 | [ |
4 | 20%Ni/N-AC-800 | DMF, 100℃, 300min, 0.6MPa | 1,5-二氨基萘 | 100/94.8 | [ |
5 | 20%Ni/N,P-AC-900 | DMF, 100℃, 150min, 0.6MPa | 1,5-二氨基萘 | 100/95.8 | [ |
表2 碳材料负载镍基催化剂催化1,5-二硝基萘加氢反应性能[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 | [ |
2 | 10%Ni/C | THF, 320℃, 360min, 5.2MPa | 1,5-二氨基萘 | 96.6/2.4 | [ |
3 | 10%Ni-Zn/AC-350 | DMF, 110℃, 300min, 0.6MPa | 1,5-二氨基萘 | 100/95.6 | [ |
4 | 20%Ni/N-AC-800 | DMF, 100℃, 300min, 0.6MPa | 1,5-二氨基萘 | 100/94.8 | [ |
5 | 20%Ni/N,P-AC-900 | DMF, 100℃, 150min, 0.6MPa | 1,5-二氨基萘 | 100/95.8 | [ |
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