Get 20M+ Full-Text Papers For Less Than $1.50/day. Start a 14-Day Trial for You or Your Team.

Learn More →

Hydrogenation of nitroarenes in continuous flow with TPP/Raney Ni

Hydrogenation of nitroarenes in continuous flow with TPP/Raney Ni In this work, the method of combining the various ligands with Raney Ni in continuous flow is proposed, in which triphenylphosphine (TPP) can effectively improve the chemical selectivity of anilines prepared by nitroarenes hydrogenation and maintain high activity. Meanwhile, through the analysis of ICP, FT-IR, XRD, and EDS, we have concluded that the low degree of complexation and the uniform distribution of TPP are presumed be the keys to high selectivity and activity. TPP/Raney Ni exhibits excellent tolerance to halogens and unsaturated functional groups in the continuous flow system of nitroarenes hydrogenation. Furthermore, the practicability of the continuous flow system was tested. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Journal of Flow Chemistry Springer Journals

Hydrogenation of nitroarenes in continuous flow with TPP/Raney Ni

Download PDF
8 pages

Loading next page...
 
/lp/springer-journals/hydrogenation-of-nitroarenes-in-continuous-flow-with-tpp-raney-ni-Hu2et2rWGQ
Publisher
Springer Journals
Copyright
Copyright © Akadémiai Kiadó 2021
ISSN
2062-249X
eISSN
2063-0212
DOI
10.1007/s41981-021-00156-3
Publisher site
See Article on Publisher Site

Abstract

In this work, the method of combining the various ligands with Raney Ni in continuous flow is proposed, in which triphenylphosphine (TPP) can effectively improve the chemical selectivity of anilines prepared by nitroarenes hydrogenation and maintain high activity. Meanwhile, through the analysis of ICP, FT-IR, XRD, and EDS, we have concluded that the low degree of complexation and the uniform distribution of TPP are presumed be the keys to high selectivity and activity. TPP/Raney Ni exhibits excellent tolerance to halogens and unsaturated functional groups in the continuous flow system of nitroarenes hydrogenation. Furthermore, the practicability of the continuous flow system was tested.

Journal

Journal of Flow Chemistry – Springer Journals

Published: Dec 1, 2021

Keywords: Continuous‐flow; TPP/Raney Ni; Preparation in flow; Hydrogenation

References

  • Pd-catalyzed silicon hydride reductions of aromatic and aliphatic nitro groups
    Rahaim, RJ; Maleczka, RE
  • Mechanistic studies of the reduction of nitroarenes by NaBH4 or hydrosilanes catalyzed by supported gold nanoparticles
    Fountoulaki, S; Daikopoulou, V; Gkizis, PL; Tamiolakis, I; Armatas, GS; Lykakis, IN
  • Metal-free reduction of aromatic nitro compounds to aromatic amines with B2pin2 in isopropanol
    Lu, H; Geng, Z; Li, J; Zou, D; Wu, Y; Wu, Y
  • Chemoselective nitro reduction and hydroamination using a single iron catalyst
    Zhu, K; Shaver, MP; Thomas, SP
  • Highly chemoselective reduction of nitroarenes over non-noble metal nickel-molybdenum oxide catalysts
    Huang, H; Wang, X; Li, X; Chen, C; Zou, X; Ding, W; Lu, X
  • Ru(II) phenanthroline complex as catalyst for chemoselective hydrogenation of nitro-aryls in a green process
    Deshmukh, AA; Prashar, AK; Kinage, AK; Kumar, R; Meijboom, R
  • Co,N-codoped porous carbon-supported CoyZnS with superior activity for nitroarene hydrogenation
    Zhang, G; Tang, F; Wang, X; An, P; Wang, L; Liu, YN
  • Deciding whether to go with the flow: Evaluating the merits of flow reactors for synthesis
    Hartman, RL; McMullen, JP; Jensen, KF
  • Continuous-flow technology - A tool for the safe manufacturing of active pharmaceutical ingredients
    Gutmann, B; Cantillo, D; Kappe, CO
  • Flow approaches towards sustainability
    Vaccaro, L; Lanari, D; Marrocchi, A; Strappaveccia, G
  • The role of flow in green chemistry and engineering
    Newman, SG; Jensen, KF
  • Continuous-flow double diazotization for the synthesis of m-difluorobenzene via Balz-Schiemann reaction
    Liu, J; Wang, D; Xu, Q; Yu, H; Zhou, J; Yu, Z; Su, W
  • Dinitration of o-toluic acid in continuous-flow: process optimization and kinetic study
    Yu, Z; Xu, Q; Liu, L; Wu, Z; Huang, J; Lin, J; Su, W
  • Toward a continuous-flow synthesis of Boscalid®
    Glasnov, TN; Kappe, CO
  • Heterogeneous catalytic hydrogenation reactions in continuous-flow reactors
    Irfan, M; Glasnov, TN; Kappe, CO
  • Gas-liquid flow hydrogenation of nitroarenes: Efficient access to a pharmaceutically relevant pyrrolobenzo[1,4]diazepine scaffold
    Dimitriou, E; Jones, RH; Pritchard, RG; Miller, GJ; O’Brien, M
  • Recent progress in continuous-flow hydrogenation
    Yu, T; Jiao, J; Song, P; Nie, W; Yi, C; Zhang, Q
  • The expanding utility of continuous flow hydrogenation
    Cossar, PJ; Hizartzidis, L; Simone, MI; McCluskey, A; Gordon, CP
  • Metal fluoride promoted catalytic hydrogenation of aromatic nitro compounds over RANEY® Ni
    Liu, X; Ma, X; Liu, S; Liu, Y; Xia, C
  • Selective hydrogenation of halogenated nitroaromatics to haloanilines in batch and flow
    Loos, P; Alex, H; Hassfeld, J; Lovis, K; Platzek, J; Steinfeldt, N; Hübner, S
  • Improved continuous flow processing: Benzimidazole ring formation via catalytic hydrogenation of an aromatic nitro compound
    Chen, J; Przyuski, K; Roemmele, R; Bakale, RP
  • Continuous selective hydrogenation of Refametinib Iodo-nitroaniline Key intermediate DIM-NA over Raney cobalt catalyst at kg/day scale with online UV-visible conversion control
    Said, M; Ben, Baramov, T; Herrmann, T; Gottfried, M; Hassfeld, J; Roggan, S
  • Convenient and selective hydrogenation of nitro aromatics with a platinum nanocatalyst under ambient pressure
    Xu, K; Zhang, Y; Chen, X; Huang, L; Zhang, R; Huang, J
  • Selective synthesis of N-aryl hydroxylamines by the hydrogenation of nitroaromatics using supported platinum catalysts
    Takenaka, Y; Kiyosu, T; Choi, JC; Sakakura, T; Yasuda, H
  • Recent developments in heterogeneous selective hydrogenation of halogenated nitroaromatic compounds to halogenated anilines
    Pietrowski, M
  • A study on the selective hydrogenation of nitroaromatics to N-arylhydroxylamines using a supported Pt nanoparticle catalyst
    Boymans, EH; Witte, PT; Vogt, D
  • A safe and selective method for reduction of 2-nitrophenylacetic acid systems to N-aryl hydroxamic acids using continuous flow hydrogenation
    Ichire, O; Jans, P; Parfenov, G; Dounay, AB
  • Immobilized transition metals as catalysts for cross-couplings in continuous flow - A critical assessment of the reaction mechanism and metal leaching
    Cantillo, D; Kappe, CO
  • Reduction of nitro compounds using 3d-non-noble metal catalysts
    Formenti, D; Ferretti, F; Scharnagl, FK; Beller, M
  • Hydrogenation of Para-chloronitrobenzene over nickel borides
    Chen, YZ; Chen, YC