微反应器内基于氮氧自由基催化剂连续氧气/空气氧化反应的研究进展

doi:10.11949/0438-1157.20221021

摘要/Abstract

摘要：

连续液相氧气氧化技术代替传统氧化技术已经成为氧化反应发展的一大趋势。但是，分子氧通常需要被合适的催化剂进行活化后才能进行高选择性氧化。近年来，氮氧自由基催化剂因其能够在温和条件下高效地催化氧气氧化反应而取得了快速发展。此外，可持续的绿色氧化工艺不仅依赖于高效环保的催化体系，还需要依托能够强化传质和反应性能的反应器技术。本文介绍了连续微反应氧化技术中常用的微反应器，归纳总结了以氮氧自由基及其衍生物为催化剂的空气/氧气氧化反应在连续有机合成中的研究进展。最后，针对现阶段氮氧自由基催化的连续液相氧化技术的潜在挑战，对该技术在精细化工领域中的应用进行了展望。

关键词: 氮氧自由基, 多相流, 氧化, 液相需氧氧化, 微反应器

Abstract:

The replacement of traditional oxidation technology by continuous liquid-phase aerobic oxidation technology has become a major trend in the development of oxidation reactions. However, molecular oxygen usually needs to be activated by a suitable catalyst system for highly selective oxidation. In recent years, nitroxyl radical catalysts have achieved rapid development due to their ability to efficiently catalyze aerobic oxidation under mild conditions. In addition, sustainable green oxidation processes not only rely on efficient and environmentally friendly catalytic systems, but also on reactor technologies that can enhance mass transfer and reaction performance. This paper introduces the commonly used microreactors and summarizes the research progress of aerobic oxidation reaction in continuous organic synthesis using nitroxide radicals or their derivatives as catalysts. Finally, in view of the potential challenges of the continuous liquid-phase oxidation technology catalyzed by nitrogen oxide radicals at this stage, a prospect for the future application of this technology in the field of fine chemicals is put forward.

Key words: nitroxyl radical, multiphase flow, oxidation, liquid-phase aerobic oxidation, microreactor

中图分类号:

TQ 032.4

章承浩, 罗京, 张吉松. 微反应器内基于氮氧自由基催化剂连续氧气/空气氧化反应的研究进展[J]. 化工学报, 2023, 74(2): 511-524.

Chenghao ZHANG, Jing LUO, Jisong ZHANG. Advances in continuous aerobic oxidation based on nitroxyl radical catalyst in microreactors[J]. CIESC Journal, 2023, 74(2): 511-524.

图/表 15

图1 常用于合成的典型氮氧自由基催化剂

Fig.1 Typical nitroxyl radical catalysts commonly used in synthesis

图2 气液传质过程及模型[11]

Fig.2 Gas-liquid mass transfer process and model[11]

图3 常见的连续液相氧化微反应器

Fig.3 Typical flow micro-reactors for liquid phase aerobic oxidation

图4 TEMPO及其一些常见的衍生物[40]

Fig.4 TEMPO and some common derivatives[40]

图5 (bpy) CuⅠ /TEMPO/NMI催化体系的醇氧化机理[43]

Fig.5 Mechanism of alcohol oxidation in (bpy) CuⅠ/TEMPO/NMI catalytic system[43]

图6 微反应器内的连续液相氧气氧化过程（1 bar=0.1 MPa, 1 atm=101325 Pa）

Fig.6 Continuous liquid-phase oxygen oxidation process in micro-reactors

图7 连续流动三相反应器流程示意图[49]1—氧气罐;2—液体罐;3—减压阀;4—质量流量计;5—HPLC泵;6—气液混合器;7—柱塞流;8—固定床反应器;9—压力调节阀;10—气液分离器;11—液相流动通过红外检测

Fig.7 Schematic diagram of the continuous flow three-phase reactor[49]1—oxygen reservoir; 2—liquid reservoir; 3—pressure reducing valve; 4—mass flow controller; 5—HPLC pump; 6—gas-liquid mixer; 7—segmented flow; 8—fixed bed reactor; 9—back-pressure regular; 10—gas-liquid separator; 11—liquid-flow passing through transmission IR cell

图8 稳定的双环氮氧自由基催化剂[54]

Fig.8 Stable bicyclic nitroxide radical catalyst[54]

图9 Anelli条件下氮氧自由基催化剂的空间位阻效应对醇氧化的影响[57]

Fig.9 Effect of steric hindrance of nitroxide radical catalyst on alcohol oxidation using the Anelli conditions[57]

图10 NHPI和PINO的结构

Fig.10 Structure diagram of NHPI and PINO

图11 NHPI及其一些常见的衍生物

Fig.11 NHPI and some common derivatives

图12 NHPI催化苄基连续氧化反应装置流程

Fig.12 NHPI-catalyzed benzyl carbonylation in continuous oxidation reaction device

图13 可能的NHPI/TBN催化苄基氧化反应机理[74]

Fig.13 Possible mechanism of NHPI/TBN-catalyzed benzyl carbonylation[74]

图14 Minisci环氧化反应可能的反应机理[77]

Fig.14 Possible reaction mechanism of Minisci epoxidation reaction[77]

图15 多射流振荡盘反应器中Minisci连续环氧化系统

Fig.15 Minisci continuous epoxidation system in a multi-jet oscillating disk reactor

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