化工进展 ›› 2019, Vol. 38 ›› Issue (01): 304-314.DOI: 10.16085/j.issn.1000-6613.2018-0840
收稿日期:
2018-04-23
修回日期:
2018-10-11
出版日期:
2019-01-05
发布日期:
2019-01-05
通讯作者:
尹双凤
作者简介:
谢军(1988—),男,博士,研究方向为纳米催化材料。E-mail:<email>415689220@qq.com</email>。|尹双凤,教授,博士生导师,研究方向为工业催化。E-mail:<email>sf_yin@hnu.edu.cn</email>。
基金资助:
Jun XIE(),Teng ZHANG,Lang CHEN,Shuangfeng YIN()
Received:
2018-04-23
Revised:
2018-10-11
Online:
2019-01-05
Published:
2019-01-05
Contact:
Shuangfeng YIN
摘要:
对氯苯甲醛是一种广泛用于医药、农药和染料的精细化工中间体,发展其绿色合成工艺极具挑战性和重大意义。本文较为系统地综述了催化氧化对氯甲苯为对氯苯甲醛的制备方法,重点阐述了H2O2氧化法、空气/氧气氧化法、电解氧化法和仿生催化氧化法的工艺条件,比较了间接电氧化合成方法中的各种金属媒质,讨论了各种制备方法的优缺点,分析了其相应的合成方法在工业开发上的可行性及存在的问题。此外,简要介绍了利用光催化法选择性氧化对氯甲苯合成对氯苯甲醛的方法。通过对几种合成方法的比较,指出以H2O2和分子氧为氧化剂液相催化氧化对氯甲苯来合成对氯苯甲醛是较为经济、环保的合成方法,电解氧化法和仿生催化氧化法将为对氯苯甲醛制备提供另一条新型技术途径。
中图分类号:
谢军, 张腾, 陈浪, 尹双凤. 对氯甲苯催化氧化制备对氯苯甲醛的研究进展[J]. 化工进展, 2019, 38(01): 304-314.
Jun XIE, Teng ZHANG, Lang CHEN, Shuangfeng YIN. Research progress on the preparation of p-chlorobenzaldehyde by catalytic oxidation of p-chlorotoluene[J]. Chemical Industry and Engineering Progress, 2019, 38(01): 304-314.
序号 | 催化剂 | 溶剂 | 氧化剂 | 对氯甲苯转化率/% | 对氯苯甲醛选择性/% | 文献 |
---|---|---|---|---|---|---|
1 | VS-1 | 乙腈 | H2O2 | 13.4 | > 64.0 | [3] |
2 | PS-[VO(fsal-D,L-Ala)(H2O)] | 乙腈 | H2O2 | 13.8 | 62.8 | [4] |
3 | Co/MTiO2 | 乙酸 | H2O2 | 48.9 | 99.1 | [5] |
4 | Co/MCM-41 | 乙酸 | H2O2 | 3.0 | 100 | [6] |
5 | Mn/MCM-41 | 乙酸 | H2O2 | 41.0 | 32.2 | [6] |
6 | Co-Mn/MCM-41 | 乙酸 | H2O2 | 16.4 | 96.0 | [6] |
7 | Bi/MCM-41 | 乙腈 | H2O2 | 18.6 | 95.3 | [7] |
8 | Co-TiO2-SiO2 | 乙酸 | H2O2 | 64.5 | 100 | [8] |
9 | ZIF-67(Co) | 乙酸 | H2O2 | 75.3 | 92.9 | [8] |
表1 不同催化剂对对氯甲苯H2O2氧化的影响[3,4,5,6,7,8]
序号 | 催化剂 | 溶剂 | 氧化剂 | 对氯甲苯转化率/% | 对氯苯甲醛选择性/% | 文献 |
---|---|---|---|---|---|---|
1 | VS-1 | 乙腈 | H2O2 | 13.4 | > 64.0 | [3] |
2 | PS-[VO(fsal-D,L-Ala)(H2O)] | 乙腈 | H2O2 | 13.8 | 62.8 | [4] |
3 | Co/MTiO2 | 乙酸 | H2O2 | 48.9 | 99.1 | [5] |
4 | Co/MCM-41 | 乙酸 | H2O2 | 3.0 | 100 | [6] |
5 | Mn/MCM-41 | 乙酸 | H2O2 | 41.0 | 32.2 | [6] |
6 | Co-Mn/MCM-41 | 乙酸 | H2O2 | 16.4 | 96.0 | [6] |
7 | Bi/MCM-41 | 乙腈 | H2O2 | 18.6 | 95.3 | [7] |
8 | Co-TiO2-SiO2 | 乙酸 | H2O2 | 64.5 | 100 | [8] |
9 | ZIF-67(Co) | 乙酸 | H2O2 | 75.3 | 92.9 | [8] |
序号 | 催化剂 | 溶剂 | 氧化剂 | 对氯甲苯转化率/% | 对氯苯甲醛选择性/% | 文献 |
---|---|---|---|---|---|---|
1 | Co(OAc)2/MnSO4/KBr | 乙酸 | 空气 | 33.3 | 60 | [19] |
2 | Co(OAc)2/MnSO4/KBr | 乙酸 | 氧气 | 46.8 | 60.2 | [19] |
3 | Co(OAc)2/Mn(OAc)2/KBr | 乙酸/水 | 氧气 | 35.3 | 61.3 | [20] |
4 | Co(OAc)2/MnSO4/KBr | 乙酸/水 | 氧气 | 33.7 | 66.6 | [20] |
5 | Co(OAc)2/MnCl2/KBr | 乙酸/水 | 氧气 | 9.9 | 61.9 | [20] |
6① | Co(OAc)2/Mn(acac)2/KBr | 乙酸/水 | 氧气 | 9.4 | 48.9 | [20] |
7② | Co(OAc)2/MnSalen/KBr | 乙酸/水 | 氧气 | 微量 | 微量 | [20] |
表2 不同锰盐和锰的复合物对对氯甲苯液相空气/氧气氧化的影响[19,20]
序号 | 催化剂 | 溶剂 | 氧化剂 | 对氯甲苯转化率/% | 对氯苯甲醛选择性/% | 文献 |
---|---|---|---|---|---|---|
1 | Co(OAc)2/MnSO4/KBr | 乙酸 | 空气 | 33.3 | 60 | [19] |
2 | Co(OAc)2/MnSO4/KBr | 乙酸 | 氧气 | 46.8 | 60.2 | [19] |
3 | Co(OAc)2/Mn(OAc)2/KBr | 乙酸/水 | 氧气 | 35.3 | 61.3 | [20] |
4 | Co(OAc)2/MnSO4/KBr | 乙酸/水 | 氧气 | 33.7 | 66.6 | [20] |
5 | Co(OAc)2/MnCl2/KBr | 乙酸/水 | 氧气 | 9.9 | 61.9 | [20] |
6① | Co(OAc)2/Mn(acac)2/KBr | 乙酸/水 | 氧气 | 9.4 | 48.9 | [20] |
7② | Co(OAc)2/MnSalen/KBr | 乙酸/水 | 氧气 | 微量 | 微量 | [20] |
序号 | 催化剂 | 溶剂 | 氧化剂 | 对氯甲苯 转化率/% | 对氯苯甲醛选择性/% | 文献 |
---|---|---|---|---|---|---|
1 | 纤维状OMS-2 | 乙酸 | 氧气 | 86.0 | 68.7 | [32] |
2 | 巢状OMS-2 | 乙酸 | 氧气 | 94.5 | 65.0 | [33] |
3 | 树枝状OMS-2 | 乙酸 | 氧气 | 11.9 | 68.7 | [33] |
4 | Zr-OMS-2 | 乙酸 | 氧气 | 92.5 | 86.0 | [34] |
5 | Ce-OMS-2 | 乙酸 | 氧气 | 93.5 | 76.1 | [35] |
6 | Mn-ZSM-5 | 乙酸 | 氧气 | 93.8 | 90.5 | [36] |
表3 不同分子筛催化剂对对氯甲苯液相空气/氧气氧化的影响[32,33,34,35,36]
序号 | 催化剂 | 溶剂 | 氧化剂 | 对氯甲苯 转化率/% | 对氯苯甲醛选择性/% | 文献 |
---|---|---|---|---|---|---|
1 | 纤维状OMS-2 | 乙酸 | 氧气 | 86.0 | 68.7 | [32] |
2 | 巢状OMS-2 | 乙酸 | 氧气 | 94.5 | 65.0 | [33] |
3 | 树枝状OMS-2 | 乙酸 | 氧气 | 11.9 | 68.7 | [33] |
4 | Zr-OMS-2 | 乙酸 | 氧气 | 92.5 | 86.0 | [34] |
5 | Ce-OMS-2 | 乙酸 | 氧气 | 93.5 | 76.1 | [35] |
6 | Mn-ZSM-5 | 乙酸 | 氧气 | 93.8 | 90.5 | [36] |
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