Abstract
Four types of high-acidity carbon-based solid acid catalysts (CBSCs) were successfully synthesized from wood sawdust, sugarcane bagasse, coconut shell, and wood sawdust-derived lignin using fuming sulfuric acid (FSA) as the sulfonating agent. The synthesized CBSCs were successfully applied to the conversion of wood sawdust-derived glucose and fructose into levulinic acid. The findings show that FSA can provide the CBSCs with higher acidity (8.0–13.0 mmol/g) than conventional concentrated sulfuric acid. Under the suitable conditions established in this work, levulinic acid was formed with a yield of more than 50 wt% over glucose when using the synthesized CBSCs at a dosage of 30 wt% over the amount of sugar.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Availability of data and material
Not applicable.
References
Adeleye AT, Louis H, Akakuru OU, Joseph I, Enudi OC, Michael DP (2019) A review on the conversion of levulinic acid and its esters to various useful chemicals. AIMS Energy 7:165–185. https://doi.org/10.3934/ENERGY.2019.2.165
Alonso DM, Gallo JMR, Mellmer MA, Wettstein SG, Dumesic JA (2013) Direct conversion of cellulose to levulinic acid and gamma-valerolactone using solid acid catalysts. Catal Sci Technol 3:927–931. https://doi.org/10.1039/C2CY20689G
Bozell JJ, Moens L, Elliott D, Wang Y, Neuenscwander G, Fitzpatrick S, Bilski R, Jarnefeld J (2000) Production of levulinic acid and use as a platform chemical for derived products. Resour Conserv Recycl 28:227–239. https://doi.org/10.1016/S0921-3449(99)00047-6
Chung NH, Dien LQ, Que NT, Thanh NT, Ly GTP (2021) Comparative study on the conversion of Acacia mangium wood sawdust-derived xylose-containing acid hydrolysate to furfural by sulfonated solid catalysts prepared from different lignocellulosic biomass residues. Wood Sci Technol. https://doi.org/10.1007/s00226-021-01284-8
Cong H, Yuan H, Tao Z, Bao H, Zhang Z, Jiang Y, Huang D, Liu H, Wang T (2021) Recent advances in catalytic conversion of biomass to 2,5-furandicarboxylic acid. Catalysts. https://doi.org/10.3390/catal11091113
Covinich LG, Clauser NM, Felissia FE, Vallejos ME, Area MC (2020) The challenge of converting biomass polysaccharides into levulinic acid through heterogeneous catalytic processes. Biofuels Bioprod Biorefin 14:417–445. https://doi.org/10.1002/bbb.2062
Dashtban M, Gilbert A, Fatehi P (2014) Recent advancements in the production of hydroxymethylfurfural. RSC Adv 4:2037–2050. https://doi.org/10.1039/c3ra45396k
de Carvalho EGL, Rodrigues F de A, Monteiro RS, Ribas RM, da Silva MJ (2018) Experimental design and economic analysis of 5-hydroxymethylfurfural synthesis from fructose in acetone-water system using niobium phosphate as catalyst. Biomass Convers Biorefinery 8:635–646. https://doi.org/10.1007/s13399-018-0319-5
Dehkhoda AM, West AH, Ellis N (2010) Biochar based solid acid catalyst for biodiesel production. Appl Catal A Gen 382:197–204. https://doi.org/10.1016/j.apcata.2010.04.051
Fu Z, Wan H, Hu X, Cui Q, Guan G (2012) Preparation and catalytic performance of a carbon-based solid acid catalyst with high specific surface area. React Kinet Mech Catal 107:203–213. https://doi.org/10.1007/s11144-012-0466-9
Ghorpade V, Hanna M (1997) Industrial applications for levulinic acid. Cereals. Springer, Boston, pp 49–55
Girisuta B, Heeres HJ (2017) Levulinic acid from biomass: synthesis and applications. In: production of platform chemicals from sustainable resources. pp 143–169
Hayes GC, Becer CR (2020) Levulinic acid: a sustainable platform chemical for novel polymer architectures. Polym Chem 11:4068–4077. https://doi.org/10.1039/D0PY00705F
Isikgor FH, Becer CR (2015) Lignocellulosic biomass: a sustainable platform for the production of bio-based chemicals and polymers. Polym Chem 6:4497–4559. https://doi.org/10.1039/C5PY00263J
Kang S, Ye J, Chang J, Kang S, Ye J, Chang J (2013) Recent advances in carbon-based sulfonated catalyst: preparation and application. Int Rev Chem Eng 5:133–144. https://doi.org/10.15866/IRECHE.V5I2.6912
Kastner JR, Miller J, Geller DP, Locklin J, Keith LH, Johnson T (2012) Catalytic esterification of fatty acids using solid acid catalysts generated from biochar and activated carbon. Catal Today 190:122–132. https://doi.org/10.1016/j.cattod.2012.02.006
Kitano M, Arai K, Kodama A, Kousaka T, Nakajima K, Hayashi S, Hara M (2009) Preparation of a sulfonated porous carbon catalyst with high specific surface area. Catal Letters 131:242–249. https://doi.org/10.1007/s10562-009-0062-4
Kong QS, Li XL, Xu HJ, Fu Y (2020) Conversion of 5-hydroxymethylfurfural to chemicals: a review of catalytic routes and product applications. Fuel Process Technol 209:106528. https://doi.org/10.1016/j.fuproc.2020.106528
Kumar A, Shende DZ, Wasewar KL (2020) Production of levulinic acid: a promising building block material for pharmaceutical and food industry. Mater Today Proc 29:790–793. https://doi.org/10.1016/j.matpr.2020.04.749
Kuster BFM (1990) 5-Hydroxymethylfurfural (HMF). A review focussing on its manufacture. Starch - Stärke 42:314–321. https://doi.org/10.1002/star.19900420808
Li H, Xia Z, Yan P, Zhang ZC (2022) Production of crude 5-hydroxymethylfurfural from glucose by dual catalysts with functional promoters in low-boiling hybrid solvent. Catal Today 402:10–16. https://doi.org/10.1016/j.cattod.2022.01.017
Liu X-Y, Huang M, Ma H-L, Zhang Z-Q, Gao J-M, Zhu Y-L, Han X-J, Guo X-Y (2010) Preparation of a carbon-based solid acid catalyst by sulfonating activated carbon in a chemical reduction process. Molecules 15:7188–7196. https://doi.org/10.3390/molecules15107188
Liu S, Zhu Y, Liao Y, Wang H, Liu Q, Ma L, Wang C (2022) Advances in understanding the humins: formation, prevention and application. Appl Energy Combust Sci. https://doi.org/10.1016/j.jaecs.2022.100062
Malu TJ, Manikandan K, Cheralathan KK (2020) Levulinic acid—a potential keto acid for producing biofuels and chemicals. In: Biomass, Biofuels, Biochemicals. Elsevier, pp 171–197
Miller GL (1959) Use of dinitrosalicylic acid reagent for determination of reducing sugar. Anal Chem 31:426–428. https://doi.org/10.1021/ac60147a030
Mukherjee A, Dumont MJ, Raghavan V (2015) Review: Sustainable production of hydroxymethylfurfural and levulinic acid: challenges and opportunities. Biomass Bioenerg 72:143–183. https://doi.org/10.1016/j.biombioe.2014.11.007
Mushrif SH, Caratzoulas S, Vlachos DG (2012) Understanding solvent effects in the selective conversion of fructose to 5-hydroxymethyl-furfural: a molecular dynamics investigation. Phys Chem Chem Phys 14:2637–2644. https://doi.org/10.1039/c2cp22694d
Rackemann DW, Doherty WO (2011) The conversion of lignocellulosics to levulinic acid. Biofuels Bioprod Biorefin 5:198–214. https://doi.org/10.1002/bbb.267
Román-Leshkov Y, Moliner M, Labinger JA, Davis ME (2010) Mechanism of glucose isomerization using a solid lewis acid catalyst in water. Angew Chemie Int Ed 49:8954–8957. https://doi.org/10.1002/anie.201004689
Rosatella AA, Simeonov SP, Frade RFMM, Afonso CAMM (2011) 5-Hydroxymethylfurfural (HMF) as a building block platform: biological properties, synthesis and synthetic applications. Green Chem 13:754–793. https://doi.org/10.1039/c0gc00401d
Rout PK, Nannaware AD, Prakash O, Kalra A, Rajasekharan R (2016) Synthesis of hydroxymethylfurfural from cellulose using green processes: a promising biochemical and biofuel feedstock. Chem Eng Sci 142:318–346. https://doi.org/10.1016/j.ces.2015.12.002
Shrotri A, Kobayashi H, Fukuoka A (2017) Catalytic conversion of structural carbohydrates and lignin to chemicals, 1st edn. Elsevier Inc
Thanh NT, Long NH, Dien LQ, Phuong Ly GT, Hoang PH, Minh Phuong NT, Hue NT (2020) Preparation of carbonaceous solid acid catalyst from Acacia mangium wood sawdust for conversion of same source into 5-hydroxymethylfurfural. Energy Sources Part A Recover Util Environ Eff 42:730–739. https://doi.org/10.1080/15567036.2019.1602195
Wang T, Glasper JA, Shanks BH (2015) Kinetics of glucose dehydration catalyzed by homogeneous Lewis acidic metal salts in water. Appl Catal A Gen 498:214–221. https://doi.org/10.1016/j.apcata.2015.03.037
Wettstein SG, Martin Alonso D, Gürbüz EI, Dumesic JA (2012) A roadmap for conversion of lignocellulosic biomass to chemicals and fuels. Curr Opin Chem Eng 1:218–224. https://doi.org/10.1016/j.coche.2012.04.002
Xue Z, Yu D, Zhao X, Mu T (2019) Upgrading of levulinic acid into diverse N-containing functional chemicals. Green Chem 21:5449–5468. https://doi.org/10.1039/c9gc02415h
Yan L, Liu N, Wang Y, Machida H, Qi X (2014) Production of 5-hydroxymethylfurfural from corn stalk catalyzed by corn stalk-derived carbonaceous solid acid catalyst. Bioresour Technol 173:462–466. https://doi.org/10.1016/J.BIORTECH.2014.09.148
Yu IKM, Tsang DCW (2017) Conversion of biomass to hydroxymethylfurfural: a review of catalytic systems and underlying mechanisms. Bioresour Technol 238:716–732. https://doi.org/10.1016/j.biortech.2017.04.026
Yu IKM, Tsang DCW, Yip ACK, Chen SS, Ok YS, Poon CS (2016) Valorization of food waste into hydroxymethylfurfural: dual role of metal ions in successive conversion steps. Bioresour Technol 219:338–347. https://doi.org/10.1016/j.biortech.2016.08.002
Zhang M, Wang N, Liu J, Wang C, Xu Y, Ma L (2022) A review on biomass-derived levulinic acid for application in drug synthesis. Crit Rev Biotechnol 42:220–253. https://doi.org/10.1080/07388551.2021.193926
Acknowledgements
The authors would like to thank the Hanoi University of Science and Technology (HUST) for financially supporting this work under project number T2022-PC-071.
Funding
This research is funded by the Hanoi University of Science and Technology (HUST) under project number T2022-PC-071.
Author information
Authors and Affiliations
Contributions
Material preparation and data collection were performed by NTH and TTT. PHH was responsible for analyzing data and providing comments on the manuscript. The manuscript was written by NHC and LQD. All authors read and approved the final manuscript.
Corresponding author
Ethics declarations
Conflict of interest
All the authors declare that they have no conflicts of interest.
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Rights and permissions
Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.
About this article
Cite this article
Hue, N.T., Thanh, T.T., Chung, N.H. et al. Preparation of sulfonated carbonaceous solid acid catalysts by fuming sulfuric acid from different lignocellulosic sources and application for the conversion of Acacia mangium wood sawdust-derived glucose and fructose into levulinic acid. Eur. J. Wood Prod. 82, 529–539 (2024). https://doi.org/10.1007/s00107-023-02017-3
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00107-023-02017-3