Abstract
A series of inexpensive electroplating sludge-derived magnetic copper-containing catalysts were developed for the selective hydrogenation of biomass-based furfural (FFR) into furfuryl alcohol (FA) and 2-methylfuran (MF). The specific structural characteristics of as-prepared magnetic copper-containing samples were clearly identified through various techniques, including XRD, XPS, N2 adsorption–desorption, NH3-TPD, SEM and so on. The characterizations revealed that the hydrogen pre-activated magnetic catalysts supplied metallic Cu species, medium acidity and porosity for the catalytic upgrading of FFR in hydrogen atmosphere. As for FFR-to-FA as well as FFR-to-MF transformations, the magnetic copper-containing catalyst with calcination temperature of 800 °C exhibited excellent performance towards the formation of FA and MF, wherein desirable FA yield of 98.5 mol% and MF yield of 71.3 mol% were achieved at reaction temperatures of 160 °C and 240 °C, respectively. The reuse experiments indicated that the recycled catalysts still maintained excellent activity and stability even after four-time recycling. The present study thus highlights a new approach for the resource utilization of electroplating sludge, which also supplies low-cost and efficient catalytic materials for the selective upgrading of various biomass-derived platform molecules.
Similar content being viewed by others
Data availability
Data sharing is not applicable to this article.
References
Sangeeta Moka S, Pande M, Rani M, Gakhar R, Sharma M, Rani J, Bhaskarwar AN (2014) Alternative fuels: An overview of current trends and scope for future. Renew Sust Energ Rev 32:697–712. https://doi.org/10.1016/j.rser.2014.01.023
Hu L, Jiang YT, Wang XY, He AY, Xu JX, Wu Z (2020) Recent advances and mechanistic insights on the production of biomass-derived 2,5-bis(alkoxymethyl)furans. Biomass Conv Bioref. https://doi.org/10.1007/s13399-020-01062-9
Zhang ZH, Huber GW (2018) Catalytic oxidation of carbohydrates into organic acids and furan chemicals. Chem Soc Rev 47:1351–1390. https://doi.org/10.1039/c7cs00213k
Ouyang WY, Yepez A, Romero AA, Luque R (2018) Towards industrial furfural conversion: Selectivity and stability of palladium and platinum catalysts under continuous flow regime. Catal Today 308:32–37. https://doi.org/10.1016/j.cattod.2017.07.011
Casoni AI, Hoch PM, Volpe MA, Gutierrez VS (2018) Catalytic conversion of furfural from pyrolysis of sunflower seed hulls for producing bio-based furfuryl alcohol. J Clean Prod 178:237–246. https://doi.org/10.1016/j.jclepro.2018.01.031
Singh G, Singh L, Gahtori J, Gupta RK, Samanta C, Bal R, Bordoloi A (2021) Catalytic hydrogenation of furfural to furfuryl alcohol over chromium-free catalyst: enhanced selectivity in the presence of solvent. Mol Catal 500:111339. https://doi.org/10.1016/j.mcat.2020.111339
Sudiyarmanto S, Aulia F, Adzim F, Setiyanto H, Dwiatmoko AA (2018) Catalytic conversion of furfural to furfuryl alcohol over ruthenium based catalysts. In: 4th International Symposium on Applied Chemistry (ISAC), 2024: 020027 (Bumi Serpong Damai, Indonesia). https://doi.org/10.1063/1.5064313
Li XD, Jia P, Wang TF (2016) Furfural: a promising platform compound for sustainable production of C-4 and C-5 chemicals. ACS Catal 6:7621–7640. https://doi.org/10.1021/acscatal.6b01838
Shen G, Andrioletti B, Queneau Y (2020) Furfural and 5-(hydroxymethyl)furfural: Two pivotal intermediates for bio-based chemistry. Curr Opin Green Sustain Chem. 26:100384. https://doi.org/10.1016/j.cogsc.2020.100384
An ZD, Li J (2022) Recent advances in the catalytic transfer hydrogenation of furfural to furfuryl alcohol over heterogeneous catalysts. Green Chem 24:1780–1808. https://doi.org/10.1039/d1gc04440k
Jaswal A, Singh PP, Mondal T (2022) Furfural - a versatile, biomass-derived platform chemical for the production of renewable chemicals. Green Chem 24:510–551. https://doi.org/10.1039/d1gc03278j
Liu XF, Yu DY, Yang WJ, Zhang QY, Wu HG, Li C (2021) Development of sustainable catalytic pathways for furan derivatives. Front Chem 9:707908. https://doi.org/10.3389/fchem.2021.707908
Fang WT, Riisager A (2021) Recent advances in heterogeneous catalytic transfer hydrogenation/hydrogenolysis for valorization of biomass-derived furanic compounds. Green Chem 23:670–688. https://doi.org/10.1039/d0gc03931d
Bozell JJ, Petersen GR (2010) Technology development for the production of biobased products from biorefinery carbohydrates-the US department of energy’s “Top 10” revisited. Green Chem 12:539–554. https://doi.org/10.1039/b922014c
Garcia-Sancho C, Agirrezabal-Telleria I, Guemez MB, Maireles-Torres P (2014) Dehydration of D-xylose to furfural using different supported niobia catalysts. Appl Catal B-Environ 152:1–10. https://doi.org/10.1016/j.apcatb.2014.01.013
Li XL, Deng J, Shi J, Pan T, Yu CG, Xu HJ, Fu Y (2015) Selective conversion of furfural to cyclopentanone or cyclopentanol using different preparation methods of Cu-Co catalysts. Green Chem 17:1038–1046. https://doi.org/10.1039/c4gc01601g
Mariscal R, Maireles-Torres P, Ojeda M, Sádaba I, López Granados M (2016) Furfural: a renewable and versatile platform molecule for the synthesis of chemicals and fuels. Energy Environ Sci 9:1144–1189. https://doi.org/10.1039/c5ee02666k
Nagaiah P, Pramod CV, Rao MV, Raju BD, Rao KSR (2018) Liquid phase hydrogenation of furfural using 2-propanol over ZrO2. J Chem Sci 130:66. https://doi.org/10.1007/s12039-018-1469-5
Yan K, Wu GS, Lafleur T, Jarvis C (2014) Production, properties and catalytic hydrogenation of furfural to fuel additives and value-added chemicals. Renew Sust Energ Rev 38:663–676. https://doi.org/10.1016/j.rser.2014.07.003
Chen H, Ruan HH, Lu XL, Fu J, Langrish T, Lu XY (2018) Efficient catalytic transfer hydrogenation of furfural to furfuryl alcohol in near-critical isopropanol over Cu/MgO-Al2O3 catalyst. Mol Catal 445:94–101. https://doi.org/10.1016/j.mcat.2017.11.011
Kajaste R (2014) Chemicals from biomass - managing greenhouse gas emissions in biorefinery production chains-a review. J Clean Prod 75:1–10. https://doi.org/10.1016/j.jclepro.2014.03.070
Tuan Hoang A, Viet Pham V (2021) 2-Methylfuran (MF) as a potential biofuel: a thorough review on the production pathway from biomass, combustion progress, and application in engines. Renew Sust Energ Rev 148:111265. https://doi.org/10.1016/j.rser.2021.111265
Zhou P, Chen Y, Luan P, Zhang XL, Yuan ZL, Guo SX, Gu QF, Johannessen B, Mollah M, Chaffee AL et al (2021) Selective electrochemical hydrogenation of furfural to 2-methylfuran over a single atom Cu catalyst under mild pH conditions. Green Chem 23:3028–3038. https://doi.org/10.1039/d0gc03999c
Zhang J, Chen JZ, Guo YY, Chen LM (2015) Effective Upgrade of levulinic acid into gamma-valerolactone over an inexpensive and magnetic catalyst derived from hydrotalcite precursor. ACS Sustain Chem Eng 3:1708–1714. https://doi.org/10.1021/acssuschemeng.5b00535
Nagaraja BM, Kumar VS, Shasikala V, Padmasri AH, Sreedhar B, Raju BD, Rao KSR (2003) A highly efficient Cu/MgO catalyst for vapour phase hydrogenation of furfural to furfuryl alcohol. Catal Commun 4:287–293. https://doi.org/10.1016/s1566-7367(03)00060-8
Putro WS, Hara T, Ichikuni N, Shimazu S (2017) Efficiently recyclable and easily separable Ni-Fe alloy catalysts for chemoselective hydrogenation of biomass-derived furfural. Chem Lett 46:149–151. https://doi.org/10.1246/cl.160905
Yang X, Xiang X, Chen H, Zheng H, Li Y-W, Zhu Y (2017) Efficient synthesis of furfuryl alcohol and 2-methylfuran from furfural over mineral-derived Cu/ZnO Catalysts. ChemCatChem. https://doi.org/10.1002/cctc.201700279
Xu N, Gong J, Huang ZH (2016) Review on the production methods and fundamental combustion characteristics of furan derivatives. Renew Sust Energ Rev 54:1189–1211. https://doi.org/10.1016/j.rser.2015.10.118
Audemar M, Ciotonea C, De Oliveira VK, Royer S, Ungureanu A, Dragoi B, Dumitriu E, Jerome F (2015) Selective hydrogenation of furfural to furfuryl alcohol in the presence of a recyclable cobalt/SBA-15 catalyst. Chemsuschem 8:1885–1891. https://doi.org/10.1002/cssc.201403398
An K, Musselwhite N, Kennedy G, Pushkarev VV, Robert Baker L, Somorjai GA (2013) Preparation of mesoporous oxides and their support effects on Pt nanoparticle catalysts in catalytic hydrogenation of furfural. J Colloid Interface Sci 392:122–128. https://doi.org/10.1016/j.jcis.2012.10.029
Date NS, Kondawar SE, Chikate RC, Rode CV (2018) Single-pot reductive rearrangement of furfural to cyclopentanone over silica-orted Pd catalysts. ACS Omega 3:9860–9871. https://doi.org/10.1021/acsomega.8b00980
Musci JJ, Merlo AB, Casella ML (2017) Aqueous phase hydrogenation of furfural using carbon-supported Ru and RuSn catalysts. Catal Today 296:43–50. https://doi.org/10.1016/j.cattod.2017.04.063
Sitthisa S, Pham T, Prasomsri T, Sooknoi T, Mallinson RG, Resasco DE (2011) Conversion of furfural and 2-methylpentanal on Pd/SiO2 and Pd-Cu/SiO2 catalysts. J Catal 280:17–27. https://doi.org/10.1016/j.jcat.2011.02.006
Zhang B, Zhu YL, Ding GQ, Zheng HY, Li YW (2012) Selective conversion of furfuryl alcohol to 1,2-pentanediol over a Ru/MnOx catalyst in aqueous phase. Green Chem 14:3402–3409. https://doi.org/10.1039/c2gc36270h
Peng G, Tian G (2010) Using electrode electrolytes to enhance electrokinetic removal of heavy metals from electroplating sludge. Chem Eng J 165:388–394. https://doi.org/10.1016/j.cej.2010.10.006
Babu BR, Bhanu SU, Meera KS (2009) Waste minimization in electroplating industries: a review. J Environ Sci Health Pt C-Environ Carcinog Ecotoxicol Rev 27:155–177. https://doi.org/10.1080/10590500903124158
Sun JX, Zhou WB, Zhang LJ, Cheng HN, Wang YG, Tang RC, Zhou HB (2021) Bioleaching of copper-containing electroplating sludge. J Environ Manage 285:112133. https://doi.org/10.1016/j.jenvman.2021.112133
Yang GCC, Kao KL (1996) Electroplating and calcium carbonate sludges as binding material for sludge solidification. Water Environ Res 68:215–221. https://doi.org/10.2175/106143096x127640
Li M, Li F, Liu Q (2018) Review on the comprehensive utilization of typical industrial sludges. Appl Chem Ind. 47:1786. https://doi.org/10.16581/j.cnki.issn1671-3206.2018.08.033
Chen H, Yuan H, Mao L, Hashmi MZ, Xu F, Tang X (2020) Stabilization/solidification of chromium-bearing electroplating sludge with alkali-activated slag binders. Chemosphere 240:124885. https://doi.org/10.1016/j.chemosphere.2019.124885
Peng G, Deng S, Liu F, Qi C, Tao L, Li T, Yu G (2020) Calcined electroplating sludge as a novel bifunctional material for removing Ni(II)-citrate in electroplating wastewater. J Clean Prod 262:121416. https://doi.org/10.1016/j.jclepro.2020.121416
Kim C, Lee CR, Song YE, Heo J, Choi SM, Lim DH, Cho J, Park C, Jang M, Kim JR (2017) Hexavalent chromium as a cathodic electron acceptor in a bipolar membrane microbial fuel cell with the simultaneous treatment of electroplating wastewater. Chem Eng J 328:703–707. https://doi.org/10.1016/j.cej.2017.07.077
Lin Z, Liu X, Xiong X, Wei S, Liu W, Lin Z (2020) Convenient fabrication of a core-shell Sn@TiO2 anode for lithium storage from tinplate electroplating sludge. Chem Commun 56:10187–10190. https://doi.org/10.1039/d0cc04403b
Granhen Tavares CR, Franco JdM (2012) Production of concrete paving blocks (CPB) utilising electroplating residues - evaluation of mechanical and micro-structural properties. Can J Chem Eng 90:1092–1101. https://doi.org/10.1002/cjce.21677
Zhang Y, Shi P, Chen L, Tang Q (2018) Utilization of electroplating sludge as subgrade backfill materials: mechanical and environmental risk evaluation. Adv Civ Eng 2018:9. https://doi.org/10.1155/2018/4891418
Dong F, Zhu YL, Zheng HY, Zhu YF, Li XQ, Li YW (2015) Cr-free Cu-catalysts for the selective hydrogenation of biomass-derived furfural to 2-methylfuran: The synergistic effect of metal and acid sites. J Mol Catal A-Chem 398:140–148. https://doi.org/10.1016/j.molcata.2014.12.001
Zhang J, Chen J (2017) Selective transfer hydrogenation of biomass-based furfural and 5-hydroxymethylfurfural over hydrotalcite-derived copper catalysts using methanol as a hydrogen donor. ACS Sustain Chem Eng 5:5982–5993. https://doi.org/10.1021/acssuschemeng.7b00778
Du H, Ma XY, Yan PF, Jiang M, Zhao Z, Zhang ZC (2019) Catalytic furfural hydrogenation to furfuryl alcohol over Cu/SiO2 catalysts: a comparative study of the preparation methods. Fuel Process Technol 193:221–231. https://doi.org/10.1016/j.fuproc.2019.05.003
Koley P, Shit SC, Joseph B, Pollastri S, Sabri YM, Mayes ELH, Nakka L, Tardio J, Mondal J (2020) Leveraging Cu/CuFe2O4-catalyzed biomass-derived furfural hydrodeoxygenation: a nanoscale metal-organic-framework template is the prime key. ACS Appl Mater Interfaces 12:21682–21700. https://doi.org/10.1021/acsami.0c03683
Funding
This work was supported by the National Natural Science Foundation of China (51976222), Key Special Project for Introduced Talents Team of Southern Marine Science and Engineering Guangdong Laboratory (Guangzhou) (GML2019ZD0101), and State Key Laboratory of Clean Energy Utilization (Open Fund Project No. ZJU-CEU2020023). The authors would like to express their appreciation to Miss Pei-Li Chen for her help in measuring the porous characteristics of as-prepared catalysts.
Author information
Authors and Affiliations
Contributions
Yaoxin Xiao contributed to investigation, resources, data curation; Jun Zhang contributed to writing—original draft preparation, writing—review and editing; Lingjun Zhu contributed to project administration; Rui Shan contributed to project administration; Haoran Yuan contributed to supervision; Yong Chen contributed to funding acquisition.
Corresponding author
Ethics declarations
Competing Interest
The authors declare no conflict of interest.
Additional information
Publisher’s note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Supplementary Information
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Xiao, Y., Zhang, J., Zhu, L. et al. Electroplating sludge-derived magnetic copper-containing catalysts for selective hydrogenation of bio-based furfural. Biomass Conv. Bioref. 14, 10225–10236 (2024). https://doi.org/10.1007/s13399-022-02970-8
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s13399-022-02970-8