Highly dispersed Pd nanoparticles in situ reduced and stabilized by nitrogen-alkali lignin-doped phenolic nanospheres and their application in vanillin hydrodeoxygenation

Xue Gu, Yu Qin, Jiahui Wei, Bing Yuan, Fengli Yu, Liantao Xin, Congxia Xie, Shitao Yu

PDF(1384 KB)
PDF(1384 KB)
Front. Chem. Sci. Eng. ›› 2024, Vol. 18 ›› Issue (11) : 127. DOI: 10.1007/s11705-024-2478-1
RESEARCH ARTICLE

Highly dispersed Pd nanoparticles in situ reduced and stabilized by nitrogen-alkali lignin-doped phenolic nanospheres and their application in vanillin hydrodeoxygenation

Author information +
History +

Abstract

Herein, we introduced a nitrogen-alkali lignin-doped phenolic resin (N@ALnPR) to produce palladium nanoparticles through an in situ reduction of palladium in an aqueous phase, without the need for additional reagents or a reducing atmosphere. The phenolic resin nanospheres and the resulting palladium nanoparticles were extensively characterized. Alkali lignin created a highly conducive environment for nitrogen incorporation, dispersion, reduction, and stabilization of palladium, leading to a distinct catalytic performance of palladium nanoparticles in vanillin hydrodeoxygenation. Under specific conditions of 1 mmol of vanillin, 40 mg of catalyst, 1 MPa H2, 90 °C, and 3 h, the optimized Pd/N@AL30PR catalyst exhibited a nearly complete conversion of vanillin, 98.9% selectivity toward p-creosol, and good stability for multiple reuses. Consequently, an environmentally friendly lignin-based catalyst was developed and used for the efficient hydrodeoxygenation conversion of lignin-based platform compounds.

Graphical abstract

Keywords

alkali lignin / phenolic nanosphere / palladium nanoparticles / hydrodeoxygenation / vanillin

Cite this article

Download citation ▾
Xue Gu, Yu Qin, Jiahui Wei, Bing Yuan, Fengli Yu, Liantao Xin, Congxia Xie, Shitao Yu. Highly dispersed Pd nanoparticles in situ reduced and stabilized by nitrogen-alkali lignin-doped phenolic nanospheres and their application in vanillin hydrodeoxygenation. Front. Chem. Sci. Eng., 2024, 18(11): 127 https://doi.org/10.1007/s11705-024-2478-1

References

[1]
Erythropel H C , Zimmerman J B , de Winter T M , Petitjean L , Melnikov F , Lam C H , Lounsbury A W , Mellor K E , Janković N Z , Tu Q . . The Green ChemisTREE: 20 years after taking root with the 12 principles. Green Chemistry, 2018, 20(9): 1929–1961
CrossRef Google scholar
[2]
Liu Z H , Li B Z , Yuan J S , Yuan Y J . Creative biological lignin conversion routes toward lignin valorization. Trends in Biotechnology, 2022, 40(12): 1550–1566
CrossRef Google scholar
[3]
Sivagurunathan P , Raj T , Mohanta C S , Semwal S , Satlewal A , Gupta R P , Puri S K , Ramakumar S S V , Kumar R . 2G waste lignin to fuel and high value-added chemicals: approaches, challenges and future outlook for sustainable development. Chemosphere, 2021, 268: 129326
CrossRef Google scholar
[4]
Gan M J , Niu Y Q , Qu X J , Zhou C H . Lignin to value-added chemicals and advanced materials: extraction, degradation, and functionalization. Green Chemistry, 2022, 24(20): 7705–7750
CrossRef Google scholar
[5]
Zhang L , Shang N , Gao S , Wang J , Meng T , Du C , Shen T , Huang J , Wu Q , Wang H . . Atomically dispersed Co catalyst for efficient hydrodeoxygenation of lignin-derived species and hydrogenation of nitroaromatics. ACS Catalysis, 2020, 10(15): 8672–8682
CrossRef Google scholar
[6]
Xu L , Liaqat F , Sun J , Khazi M I , Xie R , Zhu D . Advances in the vanillin synthesis and biotransformation: a review. Renewable & Sustainable Energy Reviews, 2024, 189: 113905
CrossRef Google scholar
[7]
Zhai Y , Chu M , Shang N , Wang C , Wang H , Gao Y . Bimetal Co8Ni2 catalyst supported on chitin-derived N-containing carbon for upgrade of biofuels. Applied Surface Science, 2020, 506: 144681
CrossRef Google scholar
[8]
RanJYangChengRCuiYWangJ. YangCheng R, Cui Y, Wang J. Significant promotion of carboxyl groups in palladium nanoparticles-supported biomass carbon catalysts for efficient low-temperature hydrodeoxygenation of lignin derivatives in water. ACS Sustainable Chemistry & Engineering, 2022, 10(22): 7277–7287
[9]
Phan D P , Lee E Y . Phosphoric acid enhancement in a Pt-encapsulated metal-organic framework (MOF) bifunctional catalyst for efficient hydro-deoxygenation of oleic acid from biomass. Journal of Catalysis, 2020, 386: 19–29
CrossRef Google scholar
[10]
Fan H , Qin F , Yuan Q , Sun Z , Gu H , Xu W , Tang H , Liu S , Wang Y , Chen W . . Improving the selectivity of hydrogenation and hydrodeoxygenation for vanillin by using vacancy-coupled Ru-N3 single atoms immobilized on defective boron nitride. Journal of Materials Chemistry. A, Materials for Energy and Sustainability, 2023, 11(33): 17560–17569
CrossRef Google scholar
[11]
Yue X , Shang N , Gao W , Cheng X , Gao S , Wang C , Wang Z . PdAg nanoparticles supported on bipyridine-based porous organic polymers: an effective bimetallic catalyst for the hydrodeoxygenation of vanillin. Energy Technology, 2021, 9(9): 2100306
CrossRef Google scholar
[12]
Santos J L , Mäki-Arvela P , Wärnå J , Monzón A , Centeno M A , Murzin D Y U . Hydrodeoxygenation of vanillin over noble metal catalyst supported on biochars. Part II: catalytic behaviour. Applied Catalysis B: Environmental, 2020, 268: 118425
CrossRef Google scholar
[13]
Zong R , Li H , Ding W , Huang H . Highly dispersed Pd on zeolite/carbon nanocomposites for selective hydrodeoxygenation of biomass-derived molecules under mild conditions. ACS Sustainable Chemistry & Engineering, 2021, 9(29): 9891–9902
CrossRef Google scholar
[14]
Strapasson G B , Sousa L S , Báfero G B , Leite D S , Moreno B D , Rodella C B , Zanchet D . Acidity modulation of Pt-supported catalyst enhances C–O bond cleavage over acetone hydrodeoxygenation. Applied Catalysis B: Environmental, 2023, 335: 122863
CrossRef Google scholar
[15]
Aadil K R , Barapatre A , Meena A S , Jha H . Hydrogen peroxide sensing and cytotoxicity activity of acacia lignin stabilized silver nanoparticles. International Journal of Biological Macromolecules, 2016, 82: 39–47
CrossRef Google scholar
[16]
Chen X , Yuan B , Yu F , Liu Y , Xie C , Yu S . Hydrogenation of α-pinene over platinum nanoparticles reduced and stabilized by sodium lignosulfonate. ACS Omega, 2020, 5(15): 8902–8911
CrossRef Google scholar
[17]
Zhang Z , Wei J , Yuan B , Yu F , Xie C , Yu S . Hydrodeoxygenation of vanillin over Pd nanoparticles reduced and stabilized by sodium lignosulfonate in aqueous phase. Industrial Crops and Products, 2023, 192: 116055
CrossRef Google scholar
[18]
Pletzer D , Asnis J , Slavin Y N , Hancock R E W , Bach H , Saatchi K , Häfeli U O . Rapid microwave-based method for the preparation of antimicrobial lignin-capped silver nanoparticles active against multidrug-resistant bacteria. International Journal of Pharmaceutics, 2021, 596: 120299
CrossRef Google scholar
[19]
Kalami S , Arefmanesh M , Master E , Nejad M . Replacing 100% of phenol in phenolic adhesive formulations with lignin. Journal of Applied Polymer Science, 2017, 134(30): 45124
CrossRef Google scholar
[20]
Li J , Zhang J , Zhang S , Gao Q , Li J , Zhang W . Alkali lignin depolymerization under eco-friendly and cost-effective NaOH/urea aqueous solution for fast curing bio-based phenolic resin. Industrial Crops and Products, 2018, 120: 25–33
CrossRef Google scholar
[21]
Kalami S , Chen N , Borazjani H , Nejad M . Comparative analysis of different lignins as phenol replacement in phenolic adhesive formulations. Industrial Crops and Products, 2018, 125: 520–528
CrossRef Google scholar
[22]
Van Nieuwenhove I , Renders T , Lauwaert J , De Roo T , De Clercq J , Verberckmoes A . Biobased resins using lignin and glyoxal. ACS Sustainable Chemistry & Engineering, 2020, 8(51): 18789–18809
CrossRef Google scholar
[23]
Li W , Sun H , Wang G , Sui W , Dai L , Si C . Lignin as a green and multifunctional alternative to phenol for resin synthesis. Green Chemistry, 2023, 25(6): 2241–2261
CrossRef Google scholar
[24]
Mennani M , Kasbaji M , Ait Benhamou A , Boussetta A , Mekkaoui A A , Grimi N , Moubarik A . Current approaches, emerging developments and functional prospects for lignin-based catalysts—a review. Green Chemistry, 2023, 25(8): 2896–2929
CrossRef Google scholar
[25]
Yang J , Xiong F , Wang H , Ma B , Guo F , Qing Y , Chu F , Wu Y . Facile and scalable construction of nitrogen-doped lignin-based carbon nanospheres for high-performance supercapacitors. Fuel, 2023, 343: 128007
CrossRef Google scholar
[26]
Chen S , Wang G , Sui W , Parvez A M , Si C . Synthesis of lignin-functionalized phenolic nanosphere supported Ag nanoparticles with excellent dispersion stability and catalytic performance. Green Chemistry, 2020, 22(9): 2879–2888
CrossRef Google scholar
[27]
Chen S , Wang G , Sui W , Parvez A M , Dai L , Si C . Novel lignin-based phenolic nanosphere supported palladium nanoparticles with highly efficient catalytic performance and good reusability. Industrial Crops and Products, 2020, 145: 112164
CrossRef Google scholar
[28]
Chen S , Wang G , Pang T , Sui W , Chen Z , Si C . Green assembly of high-density and small-sized silver nanoparticles on lignosulfonate-phenolic resin spheres: focusing on multifunction of lignosulfonate. International Journal of Biological Macromolecules, 2021, 166: 893–901
CrossRef Google scholar
[29]
Meng Y , Li C , Liu X , Lu J , Cheng Y , Xiao L P , Wang H . Preparation of magnetic hydrogel microspheres of lignin derivate for application in water. Science of the Total Environment, 2019, 685: 847–855
CrossRef Google scholar
[30]
Liu J , Qiao S Z , Liu H , Chen J , Orpe A , Zhao D , Lu G Q M . Extension of the Stöber method to the preparation of monodisperse resorcinol-formaldehyde resin polymer and carbon spheres. Angewandte Chemie, 2011, 123(26): 6069–6073
CrossRef Google scholar
[31]
Zhao J , Niu W , Zhang L , Cai H , Han M , Yuan Y , Majeed S , Anjum S , Xu G . A template-free and surfactant-free method for high-yield synthesis of highly monodisperse 3-aminophenol–formaldehyde resin and carbon nano/microspheres. Macromolecules, 2013, 46(1): 140–145
CrossRef Google scholar
[32]
Gao S , Zhang Z , Liu K , Dong B . Direct evidence of plasmonic enhancement on catalytic reduction of 4-nitrophenol over silver nanoparticles supported on flexible fibrous networks. Applied Catalysis B: Environmental, 2016, 188: 245–252
CrossRef Google scholar
[33]
Pan H , Sun G , Zhao T . Synthesis and characterization of aminated lignin. International Journal of Biological Macromolecules, 2013, 59: 221–226
CrossRef Google scholar
[34]
Horikawa Y , Hirano S , Mihashi A , Kobayashi Y , Zhai S , Sugiyama J . Prediction of lignin contents from infrared spectroscopy: chemical digestion and lignin/biomass ratios of cryptomeria japonica. Applied Biochemistry and Biotechnology, 2019, 188(4): 1066–1076
CrossRef Google scholar
[35]
Chen Y , Gong X , Yang G , Li Q , Zhou N . Preparation and characterization of a nanolignin phenol formaldehyde resin by replacing phenol partially with lignin nanoparticles. RSC Advances, 2019, 9(50): 29255–29262
CrossRef Google scholar
[36]
Carter C F , Lange H , Ley S V , Baxendale I R , Wittkamp B , Goode J G , Gaunt N L , React I R . Flow Cell: a new analytical tool for continuous flow chemical processing. Organic Process Research & Development, 2010, 14(2): 393–404
CrossRef Google scholar
[37]
Baran T , Sargin I . Green synthesis of a palladium nanocatalyst anchored on magnetic lignin-chitosan beads for synthesis of biaryls and aryl halide cyanation. International Journal of Biological Macromolecules, 2020, 155: 814–822
CrossRef Google scholar
[38]
Kar A K , Sarkar R , Manal A K , Kumar R , Chakraborty S , Ahuja R , Srivastava R . Unveiling and understanding the remarkable enhancement in the catalytic activity by the defect creation in UIO-66 during the catalytic transfer hydrodeoxygenation of vanillin with isopropanol. Applied Catalysis B: Environmental, 2023, 325: 122385
CrossRef Google scholar
[39]
Li T , Li H , Li C . Hydrodeoxygenation of vanillin to creosol under mild conditions over carbon nanospheres supported palladium catalysts: influence of the carbon defects on surface of catalysts. Fuel, 2022, 310: 122432
CrossRef Google scholar
[40]
Kim H , Yang S , Lim Y H , Ha J M , Kim D H . Upgrading bio-oil model compound over bifunctional Ru/HZSM-5 catalysts in biphasic system: complete hydrodeoxygenation of vanillin. Journal of Hazardous Materials, 2022, 423: 126525
CrossRef Google scholar

Competing interests

The authors declare that they have no competing interests.

Acknowledgements

This work was supported by the National Natural Science Foundation of China (Grant Nos. 31870554 and 32071710).

RIGHTS & PERMISSIONS

2024 Higher Education Press
AI Summary AI Mindmap
PDF(1384 KB)

Accesses

Citations

Detail

Sections
Recommended

/