Citation: Yu ZHANG, Ying HE, Qing HE, Hui LIU, Jun-Feng MIAO, Ling-Lan LI. Preparation of Ni-Co@C-N catalysts for application to nitroaromatic-azoxybenzene reduction coupling reaction[J]. Chinese Journal of Inorganic Chemistry, ;2023, 39(9): 1738-1750. doi: 10.11862/CJIC.2023.129 shu

Preparation of Ni-Co@C-N catalysts for application to nitroaromatic-azoxybenzene reduction coupling reaction

Yu ZHANG ¹ ,
Ying HE ¹ ,
Qing HE ¹ ,
Hui LIU ^1,, ,
Jun-Feng MIAO ² ,
Ling-Lan LI ^2,,

1.
School of Materials Science and Engineering, Wuhan Institute of Technology, Wuhan 430205, China
2.
College of Chemistry and Chemical Engineering, Hubei University, Wuhan 430062, China

Corresponding author: Hui LIU, iamliuhui@live.cn Ling-Lan LI, lilinglan@126.com
Received Date: 31 January 2023
Revised Date: 18 June 2023

Figures(10)

The low-cost supported nickel nanoparticle catalysts Ni-Co@C-N were prepared with ZIF-67 as a precursor by pyrolysis and then ethylene glycol reduction. The characterization results of X-ray diffraction (XRD), scanning electron microscope (SEM), transmission electron microscope (TEM), and X-ray photoelectron spectroscopy (XPS) indicated the successful preparation of supported nickel nanoparticle catalysts Ni-Co@C-N, Ni and Co nanoparticles uniformly dispersed. Weak bases such as Na₂CO₃ and low molecular weight PVPk18 dispersants contribute to the loading of Ni nanoparticles. The results of N₂ adsorption-desorption indicated that the specific surface areas of the Ni-Co@C-N materials were between 107 and 211 m²·g^-1, and the average pore widths were between 7.4 and 11.2 nm. The catalytic performance of the Ni-Co@C-N catalysts for the synthesis of nitroaromatic compounds into the corresponding oxide azobenzene compounds was studied, and the effects of the types of alkali and dispersant on the structure and properties of catalysts were also discussed. The results demonstrated that the alkaline enhancement accelerated the nucleation rate of nanoparticles while increasing the molecular weight of dispersants limited the size growth of nanoparticles. Among them, Ni-Co@C-N-4 prepared by the weak base and low molecular weight dispersant possessed the best catalytic performance, the conversion rate and yield of raw materials reached 92.8% and 89.3% respectively after 30 min of reaction, and the cycle test showed that Ni-Co@C-N-4 had good stability.
- azoxybenzene,
- metal-organic framework,
- reduction coupling,
- bimetallic catalyst
1. [1]
  HUANG Z A, LIU H, LI L L. Progress in the synthesis of azoxybenzene compound[J]. Chemical Reagents, 2020,422(11):1318-1326. doi: 10.13822/j.cnki.hxsj.2020007689
2. [2]
  Zeynizadeh B, Gilanizadeh M. Green and highly efficient approach for the reductive coupling of nitroarenes to azoxyarenes using the new mesoporous Fe₃O₄@SiO₂@Co-Zr-Sb catalyst[J]. Res. Chem. Intermed., 2020,46(6):2969-2984. doi: 10.1007/s11164-020-04126-7
3. [3]
  Han S, Cheng Y, Liu S S, Tao C F, Wang A P, Wei W G, Yu H, Wei Y G. Selective oxidation of anilines to azobenzenes and azoxybenzenes by a molecular Mo oxide catalyst[J]. Angew. Chem. Int. Ed., 2021,60(12):6382-6385. doi: 10.1002/anie.202013940
4. [4]
  Combita D, Concepción P, Corma A. Gold catalysts for the synthesis of aromatic azocompounds from nitroaromatics in one step[J]. J. Catal., 2014,311:339-349. doi: 10.1016/j.jcat.2013.12.014
5. [5]
  Zhao J X, Chen C Q, Xing C H, Jiao Z F, Yu M T, Mei B B, Yang J, Zhang B Y, Jiang Z, Qin Y. Selectivity regulation in Au-catalyzed nitroaromatic hydrogenation by anchoring single-site metal oxide promoters[J]. ACS Catal., 2020,10(4):2837-2844. doi: 10.1021/acscatal.9b04855
6. [6]
  Qadir M I, Scholten J D, Dupont J. Ionic liquid effect: Selective aniline oxidative coupling to azoxybenzene by TiO₂[J]. Catal. Sci. Technol., 2015,5(3):1459-1462. doi: 10.1039/C4CY01257G
7. [7]
  Li J, Song S Y, Long Y, Wu L L, Wang X, Xing Y, Jin R C, Liu X G, Zhang H J. Investigating the hybrid-structure-effect of CeO₂-encapsulated Au nanostructures on the transfer coupling of nitrobenzene[J]. Adv. Mater., 2018,30(7)1704416. doi: 10.1002/adma.201704416
8. [8]
  Chen Y F, Chen J, Lin L J, Chuang G J. Synthesis of azoxybenzenes by reductive dimerization of nitrosobenzene[J]. J. Org. Chem., 2017,82(21):11626-11630. doi: 10.1021/acs.joc.7b01887
9. [9]
  Liu X, Ye S, Li H Q, Liu Y M, Cao Y, Fan K N. Mild, selective and switchable transfer reduction of nitroarenes catalyzed by supported gold nanoparticles[J]. Catal. Sci. Technol., 2013,3(12):3200-3206. doi: 10.1039/c3cy00533j
10. [10]
  Zhou B W, Song J L, Wu T B, Liu H Z, Xie C, Yang G Y, Han B X. Simultaneous and selective transformation of glucose to arabinose and nitrosobenzene to azoxybenzene driven by visible-light[J]. Green Chem., 2016,18(13):3852-3857. doi: 10.1039/C6GC00943C
11. [11]
  Dai Y, Li C, Shen Y B, Lim T B, Xu J, Li Y W, Niemantsverdriet H, Besenbacher F, Lock N, Su R. Light-tuned selective photosynthesis of azo- and azoxy-aromatics using graphitic C₃N₄[J]. Nat. Commun., 2018,9(1)60. doi: 10.1038/s41467-017-02527-8
12. [12]
  Qiao B T, Wang A Q, Yang X F, Allard L F, Jiang Z, Cui Y T, Liu J Y, Li J, Zhang T. Single-atom catalysis of Co oxidation using Pt₁/ FeO_x[J]. Nat. Chem., 2011,3(8):634-641. doi: 10.1038/nchem.1095
13. [13]
  Yang F F, Liu D, Zhao Y T, Wang H, Han J Y, Ge Q F, Zhu X L. Size dependence of vapor phase hydrodeoxygenation of m-cresol on Ni/SiO₂ catalysts[J]. ACS Catal., 2018,8(3):1672-1682. doi: 10.1021/acscatal.7b04097
14. [14]
  Xie Z Y, Zhang T, Zhao Z K. Ni nanoparticles grown on SiO₂ supports using a carbon interlayer sacrificial strategy for chemoselective hydrogenation of nitrobenzene and m-cresol[J]. ACS Appl. Nano Mater., 2021,4(9):9353-9360. doi: 10.1021/acsanm.1c01819
15. [15]
  Manna K, Zhang T, Lin W B. Postsynthetic metalation of bipyridyl-containing metal-organic frameworks for highly efficient catalytic organic transformations[J]. J. Am. Chem. Soc., 2014,136(18):6566-6569. doi: 10.1021/ja5018267
16. [16]
  Thacker N C, Lin Z K, Zhang T, Gilhula J C, Abney C W, Lin W B. Robust and porous β-diketiminate-functionalized metal-organic frameworks for earth-abundant-metal-catalyzed C-H amination and hydrogenation[J]. J. Am. Chem. Soc., 2016,138(10):3501-3509. doi: 10.1021/jacs.5b13394
17. [17]
  Xu G L, Zhang Y M, Wang K H, Fu Y, Du Z Y. Microwave-assisted stille cross-coupling reaction catalysed by in situ formed palladium nanoparticles[J]. J. Chem. Res., 2015,39(7):399-402. doi: 10.3184/174751915X14357494708710
18. [18]
  Chen Y J, Ji S F, Wang Y G, Dong J C, Chen W X, Li Z, Shen R G, Zheng L R, Zhuang Z B, Wang D S, Li Y D. Isolated single iron atoms anchored on N-doped porous carbon as an efficient electrocatalyst for the oxygen reduction reaction[J]. Angew. Chem. Int. Ed., 2017,56(24):6937-6941. doi: 10.1002/anie.201702473
19. [19]
  Cai Q L, Xu Q H, Zhang Y Y, Fu Y H, Chen D L, Zhang J W, Zhu W D, Zhang F M. Boosted catalytic hydrogenation performance using isolated Co sites anchored on nitrogen-incorporated hollow porous carbon[J]. J. Phys. Chem. C, 2021,125(9):5088-5098. doi: 10.1021/acs.jpcc.0c11487
20. [20]
  Zhong Y C, Liao P S, Kang J W, Liu Q L, Wang S H, Li S S, Liu X L, Li G Q. Locking effect in metal@MOF with superior stability for highly chemoselective Catalysis[J]. J. Am. Chem. Soc., 2023,145(8):4659-4666. doi: 10.1021/jacs.2c12590
21. [21]
  Zhao J B, Yang W C, Yuan H F, Li X M, Bing W Z, Han L F, Wu K L. ZIF-8@ZIF-67 derived Co/NPHC catalysts for efficient and selective hydrogenation of nitroarenes[J]. Catal. Lett., 2023,153(3):824-835. doi: 10.1007/s10562-022-04016-0
22. [22]
  Chou K S, Lai Y S. Effect of polyvinyl pyrrolidone molecular weights on the formation of nanosized silver colloids[J]. Mater. Chem. Phys., 2004,83(1):82-88. doi: 10.1016/j.matchemphys.2003.09.026
23. [23]
  Wang X B, Zhang S H, Zhang Z C. Synthesis of hexagonal nanosized silver sulfide at room temperature[J]. Mater. Chem. Phys., 2008,107(1):9-12. doi: 10.1016/j.matchemphys.2007.07.015
24. [24]
  Chen D D, Sun Q H, Han C, Guo Y Y, Huang Q, Goddard W A. Enhanced oxygen evolution catalyzed by in-situ formed Fe-doped Ni oxyhydroxides in carbon nanotubes[J]. J. Mater. Chem. A, 2022,10(30):16007-16015. doi: 10.1039/D2TA04042E
25. [25]
  Qian H F, Zhu M Z, Wu Z K, Jin R C. Quantum sized gold nanoclusters with atomic precision[J]. Acc. Chem. Res., 2012,45(9):1470-1479. doi: 10.1021/ar200331z
26. [26]
  FANG H Y, ZHAO J C, KANG X Y, LI Y C. Ni/biomass-derived nitrogen-doped porous carbon nanocomposites: Preparation and electrocatalysis for methanol oxidation reaction[J]. Chinese J. Inorg. Chem., 2022,38(10):1959-1969. doi: 10.11862/CJIC.2022.188
27. [27]
  Li B Z, Sun K Q, Guo Y B, Tian J P, Xue Y B, Sun D K. Adsorption kinetics of phenol from water on Fe/Ac[J]. Fuel, 2013,110:99-106. doi: 10.1016/j.fuel.2012.10.043
28. [28]
  Wu N, Zhai M X, Chen F, Zhang X, Guo R H, Hu T P, Ma M M. Nickel nanocrystal/nitrogen-doped carbon composites as efficient and carbon monoxide-resistant electrocatalysts for methanol oxidation reactions[J]. Nanoscale, 2020,12(42):21687-21694. doi: 10.1039/D0NR04822D
29. [29]
  Chuang T J, Brundle C R, Rice D W. Interpretation of the X-ray photoemission spectra of cobalt oxides and cobalt oxide surfaces[J]. Surf. Sci., 1976,59:413-429. doi: 10.1016/0039-6028(76)90026-1
30. [30]
  Ledeuil J B, Uhart A, Soule S, Allouche J, Dupin J C, Martinez H. New insights into micro/nanoscale combined probes (nanoauger, muxps) to characterize Ag/Au@SiO₂ core-shell assemblies[J]. Nanoscale, 2014,6(19):11130-11140. doi: 10.1039/C4NR03211J
31. [31]
  Zhang Y Z, Song Y Y, Zhao J C, Li S X, Li Y C. Ultrahigh electrocatalytic aactivity and durability of bimetallic Au@Ni core-shell nanoparticles supported on RGO for methanol oxidation reaction in alkaline electrolyte[J]. J. Alloy. Compd., 2020,822(5)153322.
32. [32]
  Tan S F, Ouyang W M, Ji Y J, Hong Q W. Carbon wrapped bimetallic NiCo nanospheres toward excellent HER and OER performance[J]. J. Alloy. Compd., 2021,889(31)161528.
33. [33]
  Yang H Y, Chen Z L, Hao W J, Xu H B, Guo Y H, Wu R B. Catalyzing overall water splitting at an ultralow cell voltage of 1.42 V via coupled Co-doped NiO nanosheets with carbon[J]. Appl. Catal. B-Environ., 2019,252:214-221. doi: 10.1016/j.apcatb.2019.04.021
34. [34]
  Paul B, Vadivel S, Yadav N, Dhar S S. Room temperature catalytic reduction of nitrobenzene to azoxybenzene over one pot synthesised reduced graphene oxide decorated with Ag/ZnO nanocomposite[J]. Catal. Commun., 2019,124:71-75. doi: 10.1016/j.catcom.2019.02.026
35. [35]
  Bai C H, Li A Q, Yao X F, Liu H L, Li Y W. Efficient and selective aerobic oxidation of alcohols catalysed by MOF-derived Co catalysts[J]. Green. Chem., 2016,18(4):1061-1069. doi: 10.1039/C5GC02082D
36. [36]
  Mercado R, Wahl C, Lu J E, Zhang T J, Lu B Z, Zhang P, Lu J Q, Allen A L, Zhang J Z, Chen S W. Nitrogen-doped porous carbon cages for electrocatalytic reduction of oxygen: Enhanced performance with iron and cobalt dual metal centers[J]. ChemCatChem, 2020,12(12):3230-3239. doi: 10.1002/cctc.201902324
37. [37]
  Xue H R, Tang J, Gong H, Guo H, Fan X L, Wang T, He J P, Yamauchi Y. Fabrication of PdCo bimetallic nanoparticles anchored on three-dimensional ordered N-doped porous carbon as an efficient catalyst for oxygen reduction reaction[J]. ACS Appl. Mater. Interfaces, 2016,8(32):20766-20771. doi: 10.1021/acsami.6b05856
38. [38]
  Ferlin F, Cappelletti M, Vivani R, Vivani R, Pica M, Piermatti O, Vaccaro L. Au@zirconium-phosphonate nanoparticles as an effective catalytic system for the chemoselective and switchable reduction of nitroarenes[J]. Green Chem., 2019,21(3):614-626. doi: 10.1039/C8GC03513J
39. [39]
  Chen Z C, Qiu Y T, Wu X X, Ni Y, Shen L, Wu J, Jiang S. Highly selective reduction of nitrobenzenes to azoxybenzenes with a copper catalyst[J]. Tetrahedron Lett., 2018,59(14):1382-1384. doi: 10.1016/j.tetlet.2018.02.064
40. [40]
  Hou T T, Wang Y H, Zhang J, Li M R, Lu J M, Heggen M, Sievers C, Wang F. Peculiar hydrogenation reactivity of Ni-Ni^δ⁺ clusters stabilized by ceria in reducing nitrobenzene to azoxybenzene[J]. J. Catal., 2017,353:107-115. doi: 10.1016/j.jcat.2017.07.004
1. [1]
  Peiran ZHAO , Yuqian LIU , Cheng HE , Chunying DUAN . A functionalized Eu³⁺ metal-organic framework for selective fluorescent detection of pyrene. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 713-724. doi: 10.11862/CJIC.20230355
2. [2]
  Tiantian MA , Sumei LI , Chengyu ZHANG , Lu XU , Yiyan BAI , Yunlong FU , Wenjuan JI , Haiying YANG . Methyl-functionalized Cd-based metal-organic framework for highly sensitive electrochemical sensing of dopamine. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 725-735. doi: 10.11862/CJIC.20230351
3. [3]
  Lu XU , Chengyu ZHANG , Wenjuan JI , Haiying YANG , Yunlong FU . Zinc metal-organic framework with high-density free carboxyl oxygen functionalized pore walls for targeted electrochemical sensing of paracetamol. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 907-918. doi: 10.11862/CJIC.20230431
4. [4]
  Xiaoling LUO , Pintian ZOU , Xiaoyan WANG , Zheng LIU , Xiangfei KONG , Qun TANG , Sheng WANG . Synthesis, crystal structures, and properties of lanthanide metal-organic frameworks based on 2, 5-dibromoterephthalic acid ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1143-1150. doi: 10.11862/CJIC.20230271
5. [5]
  Youlin SI , Shuquan SUN , Junsong YANG , Zijun BIE , Yan CHEN , Li LUO . Synthesis and adsorption properties of Zn(Ⅱ) metal-organic framework based on 3, 3', 5, 5'-tetraimidazolyl biphenyl ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1755-1762. doi: 10.11862/CJIC.20240061
6. [6]
  Ruolin CHENG , Haoran WANG , Jing REN , Yingying MA , Huagen LIANG . Efficient photocatalytic CO₂ cycloaddition over W₁₈O₄₉/NH₂-UiO-66 composite catalyst. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 523-532. doi: 10.11862/CJIC.20230349
7. [7]
  Wenxiu Yang , Jinfeng Zhang , Quanlong Xu , Yun Yang , Lijie Zhang . Bimetallic AuCu Alloy Decorated Covalent Organic Frameworks for Efficient Photocatalytic Hydrogen Production. Acta Physico-Chimica Sinica, 2024, 40(10): 2312014-. doi: 10.3866/PKU.WHXB202312014
8. [8]
  Jing SU , Bingrong LI , Yiyan BAI , Wenjuan JI , Haiying YANG , Zhefeng Fan . Highly sensitive electrochemical dopamine sensor based on a highly stable In-based metal-organic framework with amino-enriched pores. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1337-1346. doi: 10.11862/CJIC.20230414
9. [9]
  Qiuyang LUO , Xiaoning TANG , Shu XIA , Junnan LIU , Xingfu YANG , Jie LEI . Application of a densely hydrophobic copper metal layer in-situ prepared with organic solvents for protecting zinc anodes. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1243-1253. doi: 10.11862/CJIC.20240110
10. [10]
  Kun WANG , Wenrui LIU , Peng JIANG , Yuhang SONG , Lihua CHEN , Zhao DENG . Hierarchical hollow structured BiOBr-Pt catalysts for photocatalytic CO₂ reduction. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1270-1278. doi: 10.11862/CJIC.20240037
11. [11]
  Guimin ZHANG , Wenjuan MA , Wenqiang DING , Zhengyi FU . Synthesis and catalytic properties of hollow AgPd bimetallic nanospheres. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 963-971. doi: 10.11862/CJIC.20230293
12. [12]
  Zhanggui DUAN , Yi PEI , Shanshan ZHENG , Zhaoyang WANG , Yongguang WANG , Junjie WANG , Yang HU , Chunxin LÜ , Wei ZHONG . Preparation of UiO-66-NH₂ supported copper catalyst and its catalytic activity on alcohol oxidation. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 496-506. doi: 10.11862/CJIC.20230317
13. [13]
  Yi YANG , Shuang WANG , Wendan WANG , Limiao CHEN . Photocatalytic CO₂ reduction performance of Z-scheme Ag-Cu₂O/BiVO₄ photocatalyst. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 895-906. doi: 10.11862/CJIC.20230434
14. [14]
  Zhuo WANG , Junshan ZHANG , Shaoyan YANG , Lingyan ZHOU , Yedi LI , Yuanpei LAN . Preparation and photocatalytic performance of CeO₂-reduced graphene oxide by thermal decomposition. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1708-1718. doi: 10.11862/CJIC.20240067
15. [15]
  Wendian XIE , Yuehua LONG , Jianyang XIE , Liqun XING , Shixiong SHE , Yan YANG , Zhihao HUANG . Preparation and ion separation performance of oligoether chains enriched covalent organic framework membrane. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1528-1536. doi: 10.11862/CJIC.20240050
16. [16]
  Hailang JIA , Hongcheng LI , Pengcheng JI , Yang TENG , Mingyun GUAN . Preparation and performance of N-doped carbon nanotubes composite Co₃O₄ as oxygen reduction reaction electrocatalysts. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 693-700. doi: 10.11862/CJIC.20230402
17. [17]
  Zhengyu Zhou , Huiqin Yao , Youlin Wu , Teng Li , Noritatsu Tsubaki , Zhiliang Jin . Synergistic Effect of Cu-Graphdiyne/Transition Bimetallic Tungstate Formed S-Scheme Heterojunction for Enhanced Photocatalytic Hydrogen Evolution. Acta Physico-Chimica Sinica, 2024, 40(10): 2312010-. doi: 10.3866/PKU.WHXB202312010
18. [18]
  Endong YANG , Haoze TIAN , Ke ZHANG , Yongbing LOU . Efficient oxygen evolution reaction of CuCo₂O₄/NiFe-layered bimetallic hydroxide core-shell nanoflower sphere arrays. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 930-940. doi: 10.11862/CJIC.20230369
19. [19]
  Yan LIU , Jiaxin GUO , Song YANG , Shixian XU , Yanyan YANG , Zhongliang YU , Xiaogang HAO . Exclusionary recovery of phosphate anions with low concentration from wastewater using a CoNi-layered double hydroxide/graphene electronically controlled separation film. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1775-1783. doi: 10.11862/CJIC.20240043
20. [20]
  Huan ZHANG , Jijiang WANG , Guang FAN , Long TANG , Erlin YUE , Chao BAI , Xiao WANG , Yuqi ZHANG . A highly stable cadmium(Ⅱ) metal-organic framework for detecting tetracycline and p-nitrophenol. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 646-654. doi: 10.11862/CJIC.20230291

Get Citation

PDF

XML

Metrics

PDF Downloads(3)
Abstract views(537)
HTML views(77)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142