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CC BY 4.0 · Pharmaceutical Fronts
DOI: 10.1055/a-2550-9141
Review Article

Progress in Continuous-flow Oxidation of Aromatic Hydrocarbons

Kaikai Zhang
1   Key Laboratory for Green Pharmaceutical Technologies and Related Equipment of Ministry of Education and Key Laboratory of Pharmaceutical Engineering of Zhejiang Province, Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, Zhejiang University of Technology, Hangzhou, People's Republic of China
,
Weike Su
1   Key Laboratory for Green Pharmaceutical Technologies and Related Equipment of Ministry of Education and Key Laboratory of Pharmaceutical Engineering of Zhejiang Province, Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, Zhejiang University of Technology, Hangzhou, People's Republic of China
2   Zhejiang Governor Triangle Biomedical Industrial Technology Research Park, Huzhou, People's Republic of China
› Institutsangaben Funding None.
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Abstract

Aromatic alcohols, aromatic aldehydes, and aromatic acids are usually synthesized by oxidation of the corresponding aromatic compounds and can be used as intermediates for the synthesis of pharmaceuticals, dyes, plasticizers, and fragrances. However, implementing these oxidations in conventional batch reactors, especially on larger scales, is often associated with severe safety risks and process challenges. The potential of explosion propagation within the reactor can be reduced using continuous-flow technology, which can eliminate or alleviate these safety hazards by reducing the size of the reactor and the size of the channel. In this paper, the research progress on aromatic hydrocarbon catalytic oxidation reactions using continuous-flow technology, as well as various catalytic systems and the corresponding selectivity, is reviewed. The translation of aerobic oxidation from batch oxidation to continuous-flow processes, including process intensification and equipment study, has also been discussed.

Keywords

aromatic hydrocarbon - oxidization - continuous-flow


Publikationsverlauf

Eingereicht: 10. Oktober 2024

Angenommen: 04. März 2025

Artikel online veröffentlicht:
22. April 2025

© 2025. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution License, permitting unrestricted use, distribution, and reproduction so long as the original work is properly cited. (https://creativecommons.org/licenses/by/4.0/)

Georg Thieme Verlag KG
Oswald-Hesse-Straße 50, 70469 Stuttgart, Germany

 

  • References

  • 1 Zhou M, Li X, Bao L. et al. A new method for immobilization of NDHPI on SBA-15 carrier used as catalyst for selective oxidation of toluene. Catal Lett 2016; 146 (02) 383-390
    Suche in Google Scholar
  • 2 Huang G, Wang PA, Liu YS. et al. An efficient oxidation of toluene over Co(II)TPP supported on chitosan using air. Catal Lett 2007; 114 (3–4): 174-177
    Suche in Google Scholar
  • 3 Pieber B, Kappe CO. Aerobic oxidations in continuous flow. Top Organomet Chem 2015; 57: 1-40
    Suche in Google Scholar
  • 4 Mahmoudi B, Rostami A, Kazemnejadi M, Hamah-Ameen BA. Catalytic oxidation of alcohols and alkyl benzenes to carbonyls using Fe3O4@SiO2@(TEMPO)-co-(Chlorophyll-Co-III) as a bi-functional, self-co-oxidant nanocatalyst. Green Chem 2020; 22 (19) 6600-6613
    Suche in Google Scholar
  • 5 Yang F, Sun J, Zheng R, Qiu W, Tang J, He M. Oxidation of toluenes to benzoic acids by oxygen in non-acidic solvents. Tetrahedron 2003; 60 (05) 1225-1228
    Suche in Google Scholar
  • 6 Plutschack MB, Pieber B, Gilmore K, Seeberger PH. The hitchhiker's guide to flow chemistry. Chem Rev 2017; 117 (18) 11796-11893
    CrossrefPubMedSuche in Google Scholar
  • 7 Yoshida J, Kim H, Nagaki A. Green and sustainable chemical synthesis using flow microreactors. ChemSusChem 2011; 4 (03) 331-340
    PubMedSuche in Google Scholar
  • 8 Hu M, Wu W, Jiang H. Palladium-catalyzed oxidation reactions of alkenes with green oxidants. ChemSusChem 2019; 12 (13) 2911-2935
    CrossrefPubMedSuche in Google Scholar
  • 9 Lu B, Cai N, Sun J. et al. Solvent-free oxidation of toluene in an ionic liquid with H2O2 as oxidant. Chem Eng J 2013; 225 (01) 266-270
    Suche in Google Scholar
  • 10 Yang WY, Tang XJ, Li WJ. et al. Fast and continuous synthesis of 2,5-furandicarboxylic acid in a micropacked-bed reactor. Chem Eng J 2022; 442: 136110
    Suche in Google Scholar
  • 11 Zhang RZ, Wang LZ, Yin RH, Luo YH. Alteration in formation behaviors of chloroaromatic precursors of PCDD/Fs: an experimental study on the effect of extrinsic and intrinsic oxygen on chlorination. Chemosphere 2020; 243: 125319
    PubMedSuche in Google Scholar
  • 12 Horvat M, Kodrič G, Jereb M, Iskra J. One pot synthesis of trifluoromethyl aryl sulfoxides by trifluoromethylthiolation of arenes and subsequent oxidation with hydrogen peroxide. RSC Adv 2020; 10 (57) 34534-34540
    PubMedSuche in Google Scholar
  • 13 Ahmad S, Yasin K, Shah AT. Catalytic oxidation of toluene using Co-MCM-48 and CoMn-MCM-48 mesoporous material. J Chem Soc Pak 2018; 40 (01) 95-100
    Suche in Google Scholar
  • 14 Liu S, Pasha M, Shang MJ. et al. Kinetic study on the reaction routes in the oxidation of K/A oil by nitric acid with microreactors. Chem Eng Sci 2023; 266: 118273
    Suche in Google Scholar
  • 15 Liu DJ, Xu HC. Electrochemical rearrangement of indoles to spirooxindoles in continuous flow. Eur J Org Chem 2022; 26 (01) e202200987
    Suche in Google Scholar
  • 16 Solís RR, Rivas FJ, Martínez-Piernas A, Agüera A. Ozonation, photocatalysis and photocatalytic ozonation of diuron. Intermediates identification. Chem Eng J 2016; 292: 72-81
    Suche in Google Scholar
  • 17 Fujishima A, Honda K. Electrochemical photolysis of water at a semiconductor electrode. Nature 1972; 238 (5358) 37-38
    CrossrefPubMedSuche in Google Scholar
  • 18 Tang DY, Lu GL, Shen ZW. et al. A review on photo-, electro- and photoelectro- catalytic strategies for selective oxidation of alcohols. J Energy Chem 2023; 77: 80-118
    Suche in Google Scholar
  • 19 Yang ZS, Zhang QQ, Song H. et al. Partial oxidation of methane by photocatalysis. Chin Chem Lett 2024; 35 (01) 108418
    Suche in Google Scholar
  • 20 Long H, Chen TS, Song J, Zhu S, Xu HC. Electrochemical aromatic C-H hydroxylation in continuous flow. Nat Commun 2022; 13 (01) 3945
    PubMedSuche in Google Scholar
  • 21 Chen TS, Long H, Gao Y, Xu HC. Continuous flow electrochemistry enables practical and site-selective C-H oxidation. Angew Chem Int Ed Engl 2023; 62 (40) e202310138
    PubMedSuche in Google Scholar
  • 22 Zhu HF, Zhao JN, Li JN, Ma CF, Yu ZY, Meng QW. Visible-light-driven g-C3N4-doped Co catalyzed oxidation of benzylic hydroxylation of alkyl aromatic hydrocarbons. Chem Eng Sci 2023; 267: 118365
    Suche in Google Scholar
  • 23 Lesieur M, Genicot C, Pasau P. Development of a flow photochemical aerobic oxidation of benzylic C-H bonds. Org Lett 2018; 20 (07) 1987-1990
    PubMedSuche in Google Scholar
  • 24 Tomaszewski B, Lloyd RC, Warr AJ, Buehler K. Regioselective biocatalytic aromatic hydroxylation in a gas-liquid multiphase tube-in-tube reactor. ChemCatChem 2014; 6 (09) 2567-2576
    Suche in Google Scholar
  • 25 Zhang C, Luo J, Xie B, Liu W, Zhang J. Green and continuous aerobic oxidation of ethylbenzene over homogeneous and heterogeneous NHPI in a micro-packed bed reactor. Chem Eng J 2023; 468: 143674
    Suche in Google Scholar
  • 26 Chapman MR, Cosgrove SC, Turner NJ, Kapur N, Blacker AJ. Highly productive oxidative biocatalysis in continuous flow by enhancing the aqueous equilibrium solubility of oxygen. Angew Chem Int Ed Engl 2018; 57 (33) 10535-10539
    PubMedSuche in Google Scholar
  • 27 Gutmann B, Elsner P, Roberge D, Kappe CO. Homogeneous liquid-phase oxidation of ethylbenzene to acetophenone in continuous flow mode. ACS Catal 2013; 3 (12) 2669-2676
    Suche in Google Scholar
  • 28 Yang L, Liu P, Zhang HY, Zhang Y, Zhao J. Catalytic oxidation of o-chlorotoluene with oxygen to o-chlorobenzaldehyde in a microchannel reactor. Org Process Res Dev 2020; 24 (10) 2034-2042
    Suche in Google Scholar
  • 29 Yun L, Zhao J, Tang X, Ma C, Yu Z, Meng QW. Selective oxidation of benzylic sp3 C-H bonds using molecular oxygen in a continuous-flow microreactor. Org Process Res Dev 2021; 25 (07) 1612-1618
    Suche in Google Scholar
  • 30 Bannon R, Morrison G, Smyth M. et al. Continuous flow approach for benzylic photo-oxidations using compressed air. Org Process Res Dev 2024; 28 (08) 3307-3312
    PubMedSuche in Google Scholar
  • 31 Gary M, Ruairí B, Scott W. et al. Continuous flow photooxidation of alkyl benzenes using fine bubbles for mass transfer enhancement. Tetrahedron Lett 2021; 90: 90153613
    Suche in Google Scholar
  • 32 Greene JF, Hoover JM, Mannel DS, Root TW, Stahl SS. Continuous-flow aerobic oxidation of primary alcohols with a Copper(I)/TEMPO catalyst. Org Process Res Dev 2013; 17 (10) 1247-1251
    Suche in Google Scholar
  • 33 Naik P, García-Lacuna J, O'Neill P, Baumann M. Continuous flow oxidation of alcohols using TEMPO/NaOCl for the selective and scalable synthesis of aldehydes. Org Process Res Dev 2023; 28 (05) 1587-1596
    PubMedSuche in Google Scholar
  • 34 Blanchard V, Asbai Z, Cottet K, Boissonnat G, Port M, Amara Z. Continuous flow photo-oxidations using supported photocatalysts on silica . Org Process Res Dev 2020; 24 (05) 822-826
    Suche in Google Scholar
  • 35 Liu JM, Xu QL, Ma FQ, Yang ZJ, Liu FF, Su WK. Metal-free catalyzed aerobic oxidation of 2-nitro-4-methylsulfone toluene to 2-nitro-4-methylsulfonylbenzoic acid using a continuous-flow reactor. J Flow Chem 2022; 12 (04) 409-417
    Suche in Google Scholar
  • 36 Liu JM, Liu LC, Zhang W. et al. Continuous catalytic aerobic oxidation of o-chlorotoluene to o-chlorobenzoic acid under slug flow conditions. J Flow Chem 2023; 13 (03) 325-335
    Suche in Google Scholar
  • 37 Prieschl M, Ötvös SB, Kappe CO. Sustainable aldehyde oxidations in continuous flow using in situ-generated performic acid. ACS Sustain Chem& Eng 2021; 9 (16) 5519-5525
    CrossrefSuche in Google Scholar
  • 38 Guo SZ, Yu ZQ, Yu CM. Kilogram-scale synthesis of 2,4-dichloro-5-fluorobenzoic acid by air oxidation under the continuous-flow process. Org Process Res Dev 2018; 22 (02) 252-256
    Suche in Google Scholar
  • 39 Vanoye L, Aloui A, Pablos M. et al. A safe and efficient flow oxidation of aldehydes with O2 . Org Lett 2013; 15 (23) 5978-5981
    PubMedSuche in Google Scholar
  • 40 Nagasawa Y, Tanba K, Tada N, Yamaguchi E, Itoh A. A study of aerobic photooxidation with a continuous-flow microreactor. Synlett 2015; 26 (03) 412-415
    Suche in Google Scholar
  • 41 Kabeshov M, Musio B, Ley S. Continuous direct anodic flow oxidation of aromatic hydrocarbons to benzyl amides. React Chem Eng 2017; 2 (06) 822-825
    Suche in Google Scholar
  • 42 Colella M, Degennaro L, Luisi R. Continuous flow synthesis of heterocycles: a recent update on the flow synthesis of indoles. Molecules 2020; 25 (14) 3242
    PubMedSuche in Google Scholar
  • 43 Dai ZY, Zhang SQ, Hong X, Wang PS, Gong LZ. A practical FeCl3/HCl photocatalyst for versatile aliphatic C-H functionalization. Chem Catal 2022; 2 (05) 1211-1222
    Suche in Google Scholar