Journal of Guangdong University of Technology ›› 2023, Vol. 40 ›› Issue (06): 124-130.doi: 10.12052/gdutxb.230124

• Catalytic and Energy Materials • Previous Articles     Next Articles

Preparation of Mesoporous Mn0.5Fe0.5Ox Particles and Their Application in the Oxidative Coupling Reaction of Alcohols with Amines

Cheng Gao, Ling Wei-zhao, Chen Shi-hong, Luo Jia-jin, Wang Dan-lin, Huang Jun-shi, Liu Wen-xiu, Wang Zhao-ying, Yu Lin, Sun Ming   

  1. School of Chemical Engineering and Light Industry, Guangdong University of Technology, Guangzhou 510006, China
  • Received:2023-08-31 Online:2023-11-25 Published:2023-11-08

HTML

PDF (PC)

558

Abstract: It is of great significance to develop an inexpensive and efficient catalyst to enhance the catalytic activity of oxidation coupling of alcohols with amines to imine. In this research, a series of manganese-iron bimetallic oxide catalysts have been prepared by a simple co-precipitation method, which were applied to the catalytic reaction of oxidation coupling of benzyl methanol with aniline to N-benzylideneaniline. The effects of different Fe/Mn feed ratios on the catalytic activity of the products have been explored. The Mn0.5Fe0.5Ox sample with a Fe/Mn feed ratio of 1:1 demonstrated the best catalytic activity, giving an aniline conversion rate of 74.7%, 99.9% selectivity and 74.6% yield of N-benzylidene, respectively. Through a variety of characterizations, Mn0.5Fe0.5Ox exhibited rich mesoporous structure and surface adsorbed oxygen species, as well as excellent oxidation ability. The high-efficiency catalyst synthesized in this work has great application potential in the preparation of imines by oxidation coupling of alcohols with amines.

Key words: mesoporous structure, manganese-iron bimetallic oxide, alcohol-amine coupling method, N-benzylideneaniline

CLC Number: 

  • O625.6
[1] WANG Y, ZHANG Q, LI F, et al. Donor/acceptor maleimide and itaconimide dyes: synthesis, fluorescence and electrochemical properties [J]. Dyes and Pigments, 2020, 172: 107823.
[2] HAN Y, XING K, ZHANG J, et al. Application of sulfoximines in medicinal chemistry from 2013 to 2020 [J]. European Journal of Medicinal Chemistry, 2021, 209: 112885.
[3] SU S, CHEN L, HAO L, et al. Preparation of p-amino salicylic acid-modified polysuccinimide as water-based nanocarriers for enhancing pesticide stability and insecticidal activity [J]. Colloids and Surfaces B:Biointerfaces, 2021, 207: 111990.
[4] GUO X, LI M, ZHAO P, et al. Vanadium doped OMS-2 catalysts for one-pot synthesis of imine from benzyl alcohol and aniline: effects of vanadium content and precursor [J]. Catalysis Communications, 2022, 172: 106540.
[5] MA J, YU X, LIU X, et al. The preparation and photocatalytic activity of Ag-Pd/g-C3N4 for the coupling reaction between benzyl alcohol and aniline [J]. Molecular Catalysis, 2019, 476: 110533.
[6] OLIVEIRA R L, LEDWA K A, CHERNYAYEVA O, et al. Cerium oxide nanoparticles confined in doped mesoporous carbons: a strategy to produce catalysts for imine synthesis [J]. Inorganic Chemistry, 2023, 62(33): 13554-13565.
[7] ALCAMAND H A, OLIVEIRA H D S, BALENA J G, et al. Synthesis, characterization, and use of nanocast LaMnO3 perovskites in the catalytic production of imine by the gas-phase oxidative coupling of benzyl alcohol to aniline [J]. Catalysis Communications, 2023, 175: 106606.
[8] CHEN F, YANG T, ZHAO S, et al. Highly selective oxidation of amines to imines by Mn2O3 catalyst under eco-friendly conditions [J]. Chinese Chemical Letters, 2019, 30(12): 2282-2286.
[9] WU S, ZHANG H, CAO Q, et al. Efficient imine synthesis via oxidative coupling of alcohols with amines in an air atmosphere using a mesoporous manganese-zirconium solid solution catalyst [J]. Catalysis Science & Technology, 2021, 11(3): 810-822.
[10] QIN L, HUANG X, ZHAO B, et al. Iron oxide as a promoter for toluene catalytic oxidation over Fe-Mn/γ-Al2O3 catalysts [J]. Catalysis Letters, 2020, 150(3): 802-814.
[11] SAID S, RIAD M. Oxidation of benzyl alcohol through eco-friendly processes using Fe-doped cryptomelane catalysts [J]. Solid State Sciences, 2019, 94: 145-154.
[12] CHEN C, LI Y, YANG Y, et al. Unique mesoporous amorphous manganese iron oxide with excellent catalytic performance for benzene abatement under UV-vis-IR and IR irradiation [J]. Environmental Science:Nano, 2019, 6: 1233-1245.
[13] YANG S, QI Z, WEN Y, et al. Generation of abundant oxygen vacancies in Fe doped δ-MnO2 by a facile interfacial synthesis strategy for highly efficient catalysis of VOCs oxidation [J]. Chemical Engineering Journal, 2023, 452(4): 139657.
[14] WEN Z, LU J, ZHANG Y, et al. Simultaneous oxidation and immobilization of arsenite from water by nanosized magnetic mesoporous iron manganese bimetal oxides (Nanosized-MMIM): synergistic effect and interface catalysis [J]. Chemical Engineering Journal, 2020, 391: 123578.
[15] MASTALIR M, GLATZ M, GORGAS N, et al. Divergent coupling of alcohols and amines catalyzed by isoelectronic hydride Mn-I and Fe-II PNP pincer complexes [J]. Chemistry-a European Journal, 2016, 22(35): 12316-12320.
[16] HUANG N, QU Z, DONG C, et al. Superior performance of α@β-MnO2 for the toluene oxidation: active interface and oxygen vacancy [J]. Applied Catalysis A:General, 2018, 560: 195-205.
[17] LI P, ZHAN S, YAO L, et al. Highly porous alpha-MnO2 nanorods with enhanced defect accessibility for efficient catalytic ozonation of refractory pollutants [J]. Journal of Hazardous Materials, 2022, 437: 129235.
[18] ZHANG C, CAO Y, WANG Z, et al. Insights into the sintering resistance of sphere-like Mn2O3 in catalytic toluene oxidation: effect of manganese salt precursor and crucial role of residual trace sulfur [J]. Industrial & Engineering Chemistry Research, 2022, 61(19): 6414-6426.
[19] TAHIR A A, WIJAYANTHA K U, SAREMI-YARAHMADI S, et al. Nanostructured α-Fe2O3 thin films for photoelectrochemical hydrogen generation [J]. Chemistry of Materials, 2009, 21(16): 3763-3772.
[20] QIU J, WANG W, WANG J, et al. Efficient monolithic MnOx catalyst prepared by heat treatment for ozone decomposition [J]. Environmental Science and Pollution Research, 2022, 29: 44324-44334.
[21] LIU Y, ZHANG P. Catalytic decomposition of gaseous ozone over todorokite-type manganese dioxides at room temperature: effects of cerium modification [J]. Applied Catalysis A:General, 2017, 530: 102-110.
[22] SHI J, QI T, SUN B-C, et al. Catalytic oxidation of benzyl alcohol over MnO2: structure-activity description and reaction mechanism [J]. Chemical Engineering Journal, 2022, 440: 135802.
[23] WANG H, CHEN H, WANG Y, et al. Performance and mechanism comparison of manganese oxides at different valence states for catalytic oxidation of NO [J]. Chemical Engineering Journal, 2019, 361: 1161-1172.
[24] ALBRECHT M, RODEMERCK U, SCHNEIDER M, et al. Unexpectedly efficient CO2 hydrogenation to higher hydrocarbons over non-doped Fe2O3 [J]. Applied Catalysis B:Environmental, 2017, 204: 119-126.
[25] QIN J, LONG Y, GOU G, et al. Tuning effect of amorphous Fe2O3 on Mn3O4 for efficient atom-economic synthesis of imines at low temperature: improvingtransfer cycle of Mn3+/Mn2+ in Mn3O4 [J]. Catalysis Science & Technology, 2020, 10: 5628-5640.
No related articles found!
Viewed
Full text


Abstract

Cited
  Shared   
  Discussed   
No Suggested Reading articles found!
Copyright © 2017 Journal of Guangdong University of Technology
Add：729 East Dongfeng RD., Guangzhou PRC. Postcode: 510090
Tel：020-37626653,020-37626139,020-37626396
Email：xbzrb@gdut.edu.cn
Supported:Beijing Magtech