Abstract
Green/sustainable catalyst system is highly desirable, and to this end, biopolymer based functional hydrogel has received much attention due to its various unique properties. Herein, a palladium nanoparticle catalyst supported by natural polymer-based hydrogel, consisting of cationic nanocellulose and alginate (Pd NPs@CNCC–AHB) was prepared and its efficient catalytic applications were demonstrated for dye removal and Suzuki coupling reaction. Cationic nanocellulose was prepared based on (1) periodate oxidation, (2) Schiff base reaction, then the hydrogels were synthesized based on the ionic interaction (Ca2+) and electrostatic interactions of cationic nanocellulose and anionic alginate. Subsequently, Pd NPs formed in situ within the hydrogel based on green synthesis, consisting of PdCl2 adsorption into the CNCC–AHB hydrogel, and carbonyl-induced reduction of Pd2+ to Pd0 at 80 °C (carbonyl groups of nanocellulose as a result of periodate oxidation). CNCC here acted as the support/stabilizer and reducing agent for the preparation of Pd NPs. The TEM image shows the average diameter of Pd NPs is ~ 9 nm inside the CNCC–AHB hydrogel matrices. The as-prepared Pd NPs@CNCC–AHB hydrogel bead catalyst showed excellent performance for methylene blue in both batch and continuous systems. Also, a high catalytic performance (as high as 99% yield after 2 h) for the Suzuki reaction was obtained. The recyclability of the hydrogel catalyst was investigated. The palladium nanoparticle loaded cationic nanocellulose–alginate hydrogel (Pd NPs@CNCC–AHB) catalyst system has great potential for catalytic applications.
Graphic abstract
Similar content being viewed by others
References
Abouzeid RE, Khiari R, Beneventi D, Dufresne A (2018) Biomimetic mineralization of three-dimensional printed alginate/TEMPO-oxidized cellulose nanofibril scaffolds for bone tissue engineering. Biomacromolecules 19:4442–4452
Albani D, Shahrokhi M, Chen Z, Mitchell S, Hauert R, López N, Pérez-Ramírez J (2018) Selective ensembles in supported palladium sulfide nanoparticles for alkyne semi-hydrogenation. Nat Commun 9:2634
An X, Long Y, Ni Y (2017) Cellulose nanocrystal/hexadecyltrimethylammonium bromide/silver nanoparticle composite as a catalyst for reduction of 4-nitrophenol. Carbohydr Polym 156:253–258
Ao C et al (2018) Reusable, salt-tolerant and superhydrophilic cellulose hydrogel-coated mesh for efficient gravity-driven oil/water separation. Chem Eng J 338:271–277
Chen C, Hu L (2018) Nanocellulose toward advanced energy storage devices: structure and electrochemistry. Acc Chem Res 51:3154–3165
Chen P, Zhang X, Miao Z, Han B, An G, Liu Z (2009) In situ synthesis of noble metal nanoparticles in alginate solution and their application in catalysis. J Nanosci Nanotechnol 9:2628–2633
Chen F et al (2017) Mesoporous, three-dimensional wood membrane decorated with nanoparticles for highly efficient water treatment. ACS Nano 11:4275–4282
Cincotto FH, Golinelli DL, Machado SA, Moraes FC (2017) Electrochemical sensor based on reduced graphene oxide modified with palladium nanoparticles for determination of desipramine in urine samples. Sens Actuators B Chem 239:488–493
Dai L, Liu R, Hu L-Q, Zou Z-F, Si C-L (2017a) Lignin nanoparticle as a novel green carrier for the efficient delivery of resveratrol. ACS Sustain Chem Eng 5:8241–8249. https://doi.org/10.1021/acssuschemeng.7b01903
Dai L, Zhang L, Wang B, Yang B, Khan I, Khan A, Ni Y (2017b) Multifunctional self-assembling hydrogel from guar gum. Chem Eng J 330:1044–1051
Dai H, Huang Y, Huang H (2018) Eco-friendly polyvinyl alcohol/carboxymethyl cellulose hydrogels reinforced with graphene oxide and bentonite for enhanced adsorption of methylene blue. Carbohydr Polym 185:1–11
Dai L, Cao Q, Wang K, Han S, Si C, Liu D, Liu Y (2020a) High efficient recovery of l-lactide with lignin-based filler by thermal degradation. Ind Crops Prod 143:111954. https://doi.org/10.1016/j.indcrop.2019.111954
Dai L, Wang Y, Zou X, Chen Z, Liu H, Ni Y (2020b) Ultrasensitive physical, bio, and chemical sensors derived from 1-, 2-, and 3-D nanocellulosic materials. Small. https://doi.org/10.1002/smll.201906567
Gautam P, Dhiman M, Polshettiwar V, Bhanage BM (2016) KCC-1 supported palladium nanoparticles as an efficient and sustainable nanocatalyst for carbonylative Suzuki–Miyaura cross-coupling. Green Chem 18:5890–5899
Gu J, Hu C, Zhang W, Dichiara AB (2018) Reagentless preparation of shape memory cellulose nanofibril aerogels decorated with Pd nanoparticles and their application in dye discoloration. Appl Catal B Environ 237:482–490. https://doi.org/10.1016/j.apcatb.2018.06.002
Heijnen D, Tosi F, Vila C, Stuart MC, Elsinga PH, Szymanski W, Feringa BL (2017) Oxygen activated, palladium nanoparticle catalyzed, ultrafast cross-coupling of organolithium reagents. Angew Chem Int Ed 56:3354–3359
Hou L, Udangawa WRN, Pochiraju A, Dong W, Zheng Y, Linhardt RJ, Simmons TJ (2016) Synthesis of heparin-immobilized, magnetically addressable cellulose nanofibers for biomedical applications. ACS Biomater Sci Eng 2:1905–1913
Hu Z-H, Omer AM, Ouyang XK, Yu D (2018) Fabrication of carboxylated cellulose nanocrystal/sodium alginate hydrogel beads for adsorption of Pb(II) from aqueous solution. Int J Biol Macromol 108:149–157
Kaushik M, Moores A (2016) nanocelluloses as versatile supports for metal nanoparticles and their applications in catalysis. Green Chem 18:622–637
Kim U-J, Kuga S, Wada M, Okano T, Kondo T (2000) Periodate oxidation of crystalline cellulose. Biomacromolecules 1:488–492
Kontturi E, Laaksonen P, Linder MB, Gröschel AH, Rojas OJ, Ikkala O (2018) Advanced materials through assembly of nanocelluloses. Adv Mater 30:1703779
Kuang Y et al (2018) Conductive cellulose nanofiber enabled thick electrode for compact and flexible energy storage devices. Adv Energy Mater 8:1802398
Kumbhar A, Jadhav S, Kamble S, Rashinkar G, Salunkhe R (2013) Palladium supported hybrid cellulose–aluminum oxide composite for Suzuki–Miyaura cross coupling reaction. Tetrahedron Lett 54:1331–1337
Lawrie G, Keen I, Drew B, Chandler-Temple A, Rintoul L, Fredericks P, Grøndahl L (2007) Interactions between alginate and chitosan biopolymers characterized using FTIR and XPS. Biomacromolecules 8:2533–2541
Leguy J, Diallo A, Putaux J-L, Nishiyama Y, Heux L, Jean B (2018) Periodate oxidation followed by NaBH4 reduction converts microfibrillated cellulose into sterically stabilized neutral cellulose nanocrystal suspensions. Langmuir ACS J Surf Colloids 34:11066–11075
Li Y et al (2017) Cellulose sponge supported palladium nanoparticles as recyclable cross-coupling catalysts. ACS Appl Mater Interfaces 9:17155–17162
Liu JC, Martin DJ, Moon RJ, Youngblood JP (2015) Enhanced thermal stability of biomedical thermoplastic polyurethane with the addition of cellulose nanocrystals. J Appl Polym Sci. https://doi.org/10.1002/app.41970
Lu H et al (2019) Cellulose-supported magnetic Fe3O4–MOF composites for enhanced dye removal application. Cellulose 26:4909–4920
Mao H, Shen Y, Zhang Q, Ulaganathan M, Zhao S, Yang Y, Hng HH (2016) Highly active and stable heterogeneous catalysts based on the entrapment of noble metal nanoparticles in 3D ordered porous carbon. Carbon 96:75–82
Martins M, Mourato C, Sanches S, Noronha JP, Crespo MB, Pereira IA (2017) Biogenic platinum and palladium nanoparticles as new catalysts for the removal of pharmaceutical compounds. Water Res 108:160–168
Missoum K, Belgacem MN, Bras J (2013) Nanofibrillated cellulose surface modification: a review. Materials 6:1745–1766
Moon RJ, Martini A, Nairn J, Simonsen J, Youngblood J (2011) Cellulose nanomaterials review: structure, properties and nanocomposites. Chem Soc Rev 40:3941–3994
Nascimento DM et al (2018) Nanocellulose nanocomposite hydrogels: technological and environmental issues. Green Chem 20:2428–2448
Niu Y, Yeung LK, Crooks RM (2001) Size-selective hydrogenation of olefins by dendrimer-encapsulated palladium nanoparticles. J Am Chem Soc 123:6840–6846
Ren H, Gao Z, Wu D, Jiang J, Sun Y, Luo C (2016) Efficient Pb(II) removal using sodium alginate–carboxymethyl cellulose gel beads: preparation, characterization, and adsorption mechanism. Carbohydr Polym 137:402–409
Sahiner N, Demirci S (2017) Natural microgranular cellulose as alternative catalyst to metal nanoparticles for H2 production from NaBH4 methanolysis. Appl Catal B Environ 202:199–206
Sun B, Hou Q, Liu Z, Ni Y (2015) Sodium periodate oxidation of cellulose nanocrystal and its application as a paper wet strength additive. Cellulose 22:1135–1146
Tong R et al (2019) Highly stretchable and compressible cellulose ionic hydrogels for flexible strain sensors. Biomacromolecules 20:2096–2104
Vilian AE, Puthiaraj P, Kwak CH, Hwang S-K, Huh YS, Ahn W-S, Han Y-K (2016) Fabrication of palladium nanoparticles on porous aromatic frameworks as a sensing platform to detect vanillin. ACS Appl Mater Interfaces 8:12740–12747
Wang B, Dai L, Yang G, Bendrich G, Ni Y, Fang G (2019) A highly efficient thermo responsive palladium nanoparticles incorporated guar gum hydrogel for effective catalytic reactions. Carbohydr Polym 226:115289
Wu X, Lu C, Zhou Z, Yuan G, Xiong R, Zhang X (2014) Green synthesis and formation mechanism of cellulose nanocrystal-supported gold nanoparticles with enhanced catalytic performance. Environ Sci Nano 1:71–79
Wu X, Shi Z, Fu S, Chen J, Berry RM, Tam KC (2016) Strategy for synthesizing porous cellulose nanocrystal supported metal nanocatalysts. ACS Sustain Chem Eng 4:5929–5935
Xiang Z, Chen Y, Liu Q, Lu F (2018) A highly recyclable dip-catalyst produced from palladium nanoparticle-embedded bacterial cellulose and plant fibers. Green Chem 20:1085–1094. https://doi.org/10.1039/C7GC02835K
Xie J, Li J (2017) Smart drug delivery system based on nanocelluloses. J Bioresour Bioprod 2:1–3
Yang H, van de Ven TGM (2016) Preparation of hairy cationic nanocrystalline cellulose. Cellulose 23:1791–1801. https://doi.org/10.1007/s10570-016-0902-5
Yang J, Chen D, Zhu Y, Zhang Y, Zhu Y (2017) 3D–3D porous Bi2WO6/graphene hydrogel composite with excellent synergistic effect of adsorption-enrichment and photocatalytic degradation. Appl Catal B Environ 205:228–237
Yang F et al (2018) Silica nanosphere supported palladium nanoparticles encapsulated with graphene: high-performance electrocatalysts for methanol oxidation reaction. Appl Surf Sci 452:11–18
Yu H et al (2019) Binding conductive ink initiatively and strongly: transparent and thermally stable cellulose nanopaper as a promising substrate for flexible electronics. ACS Appl Mater Interfaces 11:20281–20290
Yue Y, Wang X, Han J, Yu L, Chen J, Wu Q, Jiang J (2019) Effects of nanocellulose on sodium alginate/polyacrylamide hydrogel: mechanical properties and adsorption–desorption capacities. Carbohydr Polym 206:289–301
Zhang K, Shen M, Liu H, Shang S, Wang D, Liimatainen H (2018) Facile synthesis of palladium and gold nanoparticles by using dialdehyde nanocellulose as template and reducing agent. Carbohydr Polym 186:132–139. https://doi.org/10.1016/j.carbpol.2018.01.048
Zhang L et al (2019) Preparation of high-strength sustainable lignocellulose gels and their applications for antiultraviolet weathering and dye removal. ACS Sustain Chem Eng 7:2998–3009
Acknowledgments
The authors would like to acknowledge the financial support from the Key Lab of Biomass Energy and Material of Jiangsu Province “Preparation and Adsorption Properties of MCB Materials Based on Pulp Fiber” [JSBEM-S-201909]; China Scholarship Council (CSC) scholarships, NSERC and the Canada Research Chairs program of the Government of Canada.
Author information
Authors and Affiliations
Corresponding authors
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Electronic supplementary material
Below is the link to the electronic supplementary material.
Pd NPs@CNCC–AHB with different CNCC/AHB ratio (MP4 4312 kb)
AHB (left) and Pd NPs@CNCC-AHB (right) (MP4 2446 kb)
Continuous MB discoloration with cracked Pd NPs@CNCC–AHB hydrogel bead catalyst (AVI 133520 kb)
Micro-CT scanning of CNCC–AHB (MP4 20667 kb)
Rights and permissions
About this article
Cite this article
Wang, B., Ran, M., Fang, G. et al. Palladium nano-catalyst supported on cationic nanocellulose–alginate hydrogel for effective catalytic reactions. Cellulose 27, 6995–7008 (2020). https://doi.org/10.1007/s10570-020-03127-4
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10570-020-03127-4