Skip to main content
SpringerLink
Log in

Tunable synthesis of Pd/COF-LZU1 for efficient catalysis in nitrophenol reduction

  • Research paper
  • Published:
Journal of Nanoparticle Research Aims and scope Submit manuscript

Abstract

Covalent organic frameworks (COFs) are emerging novel catalyst carrier. In this work, Pd/COF-LZU1 was one-pot prepared by p-phenylenediamine (PDA), triformylbenzene (TFB), and palladium acetate (Pd(OAc)2) under the catalysis of acetic acid (HAc). The effects of HAc concentration on the Pd/COF-LZU1 particle size, Pd loading, and catalytic activity in the reduction of 4-nitrophenol (4-NP) were investigated. It was found that, with the increased HAc concentration, the Pd/COF-LZU1 particle size reduced, and Pd loading and catalytic activity displayed maximum for 3 mol L−1 HAc. The catalytic reduction of 4-NP can be described by the pseudo-first-order kinetic model, and the rate constant is 20 times higher than that of palladium acetate. Pd/COF-LZU1 also showed excellent stability and reusability, demonstrating great potential in catalytic reduction reactions.

HAc displayed effects on particle size, Pd loading, and catalytic activity. Pd/COF-LZU1 prepared by one-pot method showed excellent catalytic performance.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Scheme 2
Fig. 4
Fig. 5

Similar content being viewed by others

Abbreviations

COFs:

Covalent organic frameworks

PDA:

p-Phenylenediamine

TFB:

Triformylbenzene

Pd(OAc)2 :

Palladium acetate

4-NP:

4-Nitrophenol

HAc:

Acetic acid

References

  • Bo L, Quan X, Wang X, Chen S (2008) Preparation and characteristics of carbon-supported platinum catalyst and its application in the removal of phenolic pollutants in aqueous solution by microwave-assisted catalytic oxidation. J Hazard Mater 157:179–186

    Article  CAS  Google Scholar 

  • Bódalo A, Gómez JL, Gómez M, León G, Hidalgo AM, Ruíz MA (2008) Phenol removal from water by hybrid processes: study of the membrane process step. Desalination 223:323–329

    Article  Google Scholar 

  • Bunck DN, Dichtel WR (2012) Internal functionalization of three-dimensional covalent organic frameworks. Angew Chem Int Ed 51:1885–1889

    Article  CAS  Google Scholar 

  • Dinesh et al (2018) Highly stable COF-supported Co/Co(OH)2 nanoparticles heterogeneous catalyst for reduction of nitrile/nitro compounds under mild conditions. Small. 14:e1801233

    Article  Google Scholar 

  • Ding SY, Wang W (2012) Covalent organic frameworks (COFs): from design to applications. Chem Soc Rev 42:548–568

    Article  Google Scholar 

  • Ding SY, Gao J, Wang Q, Zhang Y, Song WG, Su CY, Wang W (2011) Construction of covalent organic framework for catalysis: Pd/COF-LZU1 in Suzuki–Miyaura coupling reaction. J Am Chem Soc 133:19816–19822

    Article  CAS  Google Scholar 

  • Ding S, Yang Y, Huang H, Liu H, Hou LA (2015) Effects of feed solution chemistry on low pressure reverse osmosis filtration of cesium and strontium. J Hazard Mater 294:27–34

    Article  CAS  Google Scholar 

  • Du X, Zhao C, Li X, Huang H, Wen Y, Zhang X, Li J (2017) Novel yolk-shell polymer/carbon@ Au nanocomposites by using dendrimer-like mesoporous silica nanoparticles as hard template. J Alloy Compd 700:83–91

    Article  CAS  Google Scholar 

  • Ebert S, Rieger P, Knackmuss H-J (1999) Function of coenzyme F420 in aerobic catabolism of 2,4, 6-trinitrophenol and 2,4-dinitrophenol by Nocardioides simplex FJ2-1A. J Bacteriol 181:2669–2674

    Article  CAS  Google Scholar 

  • Gao JK, Hou LA, Zhang GH, Gu P (2015) Facile functionalized of SBA-15 via a biomimetic coating and its application in efficient removal of uranium ions from aqueous solution. J Hazard Mater 286:325–333

    Article  CAS  Google Scholar 

  • Gatard S, Salmon L, Deraedt C, Ruiz J, Astruc D, Bouquillon S (2014) Palladium nanoparticles stabilized by glycodendrimers and their application in catalysis. Eur J Inorg Chem 26:4369–4375

    Article  Google Scholar 

  • Giannis A, Sandhoff K (2010) LiBH4(NaBH4)/Me3SiCl, an unusually strong and versatile reducing agent. Angew Chem. Int. Ed. 28:218–220

    Article  Google Scholar 

  • Haruta M, Yamada N, Kobayashi T, Iijima S (1989) Gold catalysts prepared by coprecipitation for low-temperature oxidation of hydrogen and of carbon monoxide. J Catal 115:301–309

    Article  CAS  Google Scholar 

  • Jin Z, Xiao M, Bao Z, Wang P, Wang J (2012) A general approach to mesoporous metal oxide microspheres loaded with noble metal nanoparticles. Angew Chem Int Ed 124:6512–6516

    Article  Google Scholar 

  • Kalidindi SB, Oh H, Hirscher M, Esken D, Wiktor C, Turner S, van Tendeloo G, Fischer RA (2012) Metal@COFs: covalent organic frameworks as templates for Pd nanoparticles and hydrogen storage properties of Pd@COF-102 hybrid material. Chemistry. 18:10848–10856

    Article  CAS  Google Scholar 

  • Koyuncu H, Yıldız N, Salgın U, Köroğlu F, Calımlı A (2011) Adsorption of o-, m- and p-nitrophenols onto organically modified bentonites. J Hazard Mater 185:1332–1339

    Article  CAS  Google Scholar 

  • Kuppler RJ et al (2009) Potential applications of metal-organic frameworks. Coordination Chem Rev 253:3042–3066

    Article  CAS  Google Scholar 

  • Lemaire-Audoire S, Savignac M, Pourcelot G, Genêt JP, Bernard JM (1997) Chemoselective removal of allylic protecting groups using water-soluble Pd(OAc) 2/TPPTS catalyst. J Mol Catal A Chem 116:247–258

    Article  CAS  Google Scholar 

  • Li P, Zeng HC (2016) Immobilization of metal-organic framework nanocrystals for advanced design of supported nanocatalysts. ACS Appl Mater Interfaces 8:29551–29564

    Article  CAS  Google Scholar 

  • Lin JR, Gubaidullin AT, Mamedov VA, Tsuboi S (2002) Nucleophilic addition reaction of aromatic compounds with α-chloroglycidates in the presence of Lewis acid. Cheminform 2002:1781–1790

    Google Scholar 

  • Liu Y, Liu D, Yang Q, Zhong C, Mi J (2010) Comparative study of separation performance of COFs and MOFs for CH 4/CO2/H2 mixtures. Ind Eng Chem Res 49:2902–2906

    Article  CAS  Google Scholar 

  • Liu L, Tai X, Zhou X (2017) Au(3+)/Au0 supported on chromium(III) terephthalate metal organic framework (MIL-101) as an efficient heterogeneous Catalystfor three-component coupling synthesis of propargylamines. Materials 10:99

    Article  Google Scholar 

  • Lv H, Zhao H, Cao T, Lin Q, Wang LY, Zhao G (2015) Efficient degradation of high concentration azo-dye wastewater by heterogeneous Fenton process with iron-based metal-organic framework. J Mol Catal A Chem 400:81–89

    Article  CAS  Google Scholar 

  • Meyer CD, Joiner CS, Stoddart JF (2007) Template-directed synthesis employing reversible imine bond formation. Chem Soc Rev 36:1705–1723

    Article  CAS  Google Scholar 

  • Moro ME, Novillo-Fertrell J, Velazquez MM, Rodriguez LJ (2010) Kinetics of the acid hydrolysis of diazepam, bromazepam, and flunitrazepam in aqueous and micellar systems. J Pharm Sci 80:459–468

    Article  Google Scholar 

  • Mu M, Wang Y, Qin Y, Yan X, Li Y, Chen LG (2017) Two-dimensional imine-linked covalent organic frameworks as a platform for selective oxidation of olefins. ACS Appl Mater Interfaces 9:22856–22863

    Article  CAS  Google Scholar 

  • Murugan E, Vimala G (2013) Synthesis, characterization, and catalytic activity for hybrids of multi-walled carbon nanotube and amphiphilic poly(propyleneimine) dendrimer immobilized with silver and palladium nanoparticle. J Colloid Interface Sci 396:101–111

    Article  CAS  Google Scholar 

  • Peng Y, Wong WK, Hu Z, Cheng Y, Yuan D, Khan SA, Zhao D (2016) Room temperature batch and continuous flow synthesis of water- stable covalent organic frameworks (COFs). Chem Mater 28:5095–5101

    Article  CAS  Google Scholar 

  • Schestakow M, Muench F, Reimuth C, Ratke L, Ensinger W (2016) Electroless synthesis of cellulose-metal aerogel composites. Appl Phys Lett 108:8896

    Article  Google Scholar 

  • Shah MT, Balouch A, Sirajuddin, Pathan AA, Umar AA (2017) SiO2 caped Fe3O4 nanostructures as an active heterogeneous catalyst for 4-nitrophenol reduction. Microsystem Technologies 23:1–14

    Article  Google Scholar 

  • Shen X, Zhu L, Liu G, Yu H, Tang H (2008) Enhanced photocatalytic degradation and selective removal of nitrophenols by using surface molecular imprinted titania. Environ Sci Technol 42:1687–1692

    Article  CAS  Google Scholar 

  • Wang Z, Zhai S, Zhai B, Xiao Z, An Q (2014) Preparation and catalytic properties of nano-Au catalytic materials based on the reduction of 4-nitrophenol. Progress in Chemistry 26:234–247

    CAS  Google Scholar 

  • Wang Z, Su R, Wang D, Shi J, Wang JX, Pu Y, Chen JF (2017) Sulfurized graphene as efficient metal-free catalysts for reduction of 4-nitrophenol to 4-aminophenol. Ind Eng Chem Res 56:13610–13617

    Article  CAS  Google Scholar 

  • Zhao H, Kai C, Zhang H, Hong Z, Han H (2017) Pd-Au heterostructured nanonecklaces with adjustable interval and size as superior catalyst in degradation of 4-nitrophenol. Crystengcomm 19:5686–5691

    Article  Google Scholar 

  • Zhaoke Z, Takashi T, Tetsuro M (2015) Plasmon-enhanced formic acid dehydrogenation using anisotropic Pd-Au nanorods studied at the single-particle level. J Am Chem Soc 137:948

    Article  Google Scholar 

  • Zhuang X, Mai Y, Wu D, Zhang F, Feng X (2015) Two-dimensional soft nanomaterials: a fascinating world of materials. Adv Mater 27:403–427

    Article  CAS  Google Scholar 

Download references

Funding

This work was supported by the National Natural Science Foundation of China and Qinghai Qaidam Saline Lake Chemical Science Research Joint Fund (No. U1607109).

Author information

Authors and Affiliations

  1. Lab for Membrane Science and Technology, College of Chemistry, Beijing Normal University, Beijing, 100875, People’s Republic of China

    Shuang Hao, Shuyun Li & Zhiqian Jia

Authors
  1. Shuang Hao
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Shuyun Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Zhiqian Jia
    View author publications

    You can also search for this author in PubMed Google Scholar

Contributions

The manuscript was written through contributions of all authors. All authors have given approval to the final version of the manuscript.

Corresponding author

Correspondence to Zhiqian Jia.

Ethics declarations

Conflict of interest

The authors declare that they have no conflict of interest.

Additional information

Publisher’s note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Electronic supplementary material

ESM 1

(DOC 2379 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Hao, S., Li, S. & Jia, Z. Tunable synthesis of Pd/COF-LZU1 for efficient catalysis in nitrophenol reduction. J Nanopart Res 22, 270 (2020). https://doi.org/10.1007/s11051-020-05002-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1007/s11051-020-05002-6

Keywords

Search

Navigation