Abstract
The Biofine process is the currently used method for the industrial production of levulinic acid (LA) from biomass. In this process sulfuric acid is used to catalyze the reaction, the former is a corrosive and toxic catalyst. In this work, an environmental friendly catalyst: 1-butyl-2,3-dimethylimidazolium tetrafluoroborate ([BMMim][BF4]) was used to optimize the LA production from depithed sugarcane bagasse (DSB). The Box–Behnken design (response surface methodology) was used to design the set of experiments with three variables, namely, time, temperature and catalyst loading. The optimum condition for water as a solvent was 100 °C, 7 h and 4 g of a catalyst which yielded a maximum amount of 44.8% of LA from DSB. When different solvents were investigated at the optimum condition for LA production, methyl isobutyl ketone (MIBK) was the best solvent (54.2%). This study also showed that [BMMim][BF4] is capable of theoretically producing 62.1% of LA. The reusability study showed that [BMMim][BF4] can be used for up to four times without losing it activity.
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Kirchhoff, M.M.: Promoting sustainability through green chemistry. Resour. Conserv. Recycl. 44, 237–243 (2005)
Anastas, P., Warner, J.: The 12 Principles of Green Chemistry: Theory and Practice. Oxford University Press, New York (1998)
Doble, M., Kruthiventi, A.K.: Introduction. In: Doble, M., Kruthiventi, A.K. (eds.) Green Chemistry and Engineering, pp. 1–26. Academic Press, Cambridge (2007)
Hanrahan, G.: Green chemistry and sustainable chemical processes. In: Hanrahan, G. (ed.) Key Concepts in Environmental Chemistry, pp. 297–319. Academic Press, Cambridge (2012)
Isac-García, J., Dobado, J.A., Calvo-Flores, F.G., Martínez-García, H.: Green chemistry. In: Isac-García, J., Dobado, J.A., Calvo-Flores, F.G., Martínez-García, H. (eds.) Experimental Organic Chemistry: Laboratory Manual, pp. 409–415. Academic Press, Cambridge (2016)
Song, J., Han, B.: Green chemistry: a tool for the sustainable development of the chemical industry. Natl. Sci. Rev. 2, 255–258 (2015)
Smith, A.D., Landoll, M., Falls, M., Holtzapple, M.T.: Chemical production from lignocellulosic biomass: thermochemical, sugar and carboxylate platforms. In: Waldron, K. (ed.) Bioalcohol Production: Biochemical Conversion of Lignocellulosic Biomass, pp. 391–414. Woodhead Publishing, Cambridge (2010)
Wilson, K., Lee, A.F.: Bio-based chemicals from biorefining: carbohydrate conversion and utilisation. In: Waldron, K. (ed.) Advances in Biorefineries: Biomass and Waste Supply Chain Exploitation, pp. 624–658. Woodhead Publishing, Cambridge (2014)
Yan, K., Jarvis, C., Gu, J., Yan, Y.: Production and catalytic transformation of levulinic acid: a platform for speciality chemicals and fuels. Renew. Sustain Energy Rev. 51, 986–997 (2015)
Mthembu, L.D.: Production of levulinic acid from sugarcane bagasse, Master’s Thesis, Durban University of Technology (2016)
Chandel, A.K., Antunes, F.A.F., Terán-Hilares, R., Cota, J., Ellilä, S., Silveira, M.H.L., da Silva, S.S.: Bioconversion of hemicellulose into ethanol and value-added products: commercialization, trends, and future opportunities. In: Chandel, A.K., Silveira, M.H.L. (eds.) Advances in Sugarcane Biorefinery: Technologies, Commercialization, Policy Issues and Paradigm Shift for Bioethanol and By-Products, pp. 97–134. Elsevier, Amsterdam (2018)
Rackemann, D.W., Doherty, W.O.S.: The conversion of lignocellulosics to levulinic acid. Biofuels. Bioprod. Bioref. 5, 198–214 (2011)
Galletti, A.M.R., Antonetti, C., Luies, V., Licursi, D., Nasso, N.N.: Levulinic acid from waste biomass. BioResources 7, 1824–1835 (2012)
Luo, W.H., Deka, U., Beale, A.M., van Eche, E.R.H., Bruijnincx, P.C.A., Wechkhuysen, B.M.: Ruthenium-catalyzed hydrogenation of levulinic acid: influence of the support and solvent on catalyst selectivity and stability. J. Catal. 301, 175–186 (2013)
Climent, M.J., Corma, A., Iborra, S.: Heterogeneous catalysts for the one-pot synthesis of chemicals and fine chemicals. Chem. Rev. 111, 1072–1133 (2011)
Vitz, J., Erdmenger, T., Haensch, C., Schubert, U.S.: Extended dissolution studies of cellulose in imidazolium based ionic liquids. Green Chem. 11, 417 (2009)
Dissanayake, N., Thalangamaarachchige, V.D., Troxell, S., Quitevis, E.L., Abidi, N.: Substituent effects on cellulose dissolution in imidazolium-based ionic liquids. Cellulose 25, 6887 (2018)
Stepnowski, P.: Sorption, lipophilicity and partitioning phenomena of ionic liquids in environmental systems. In: Letcher, T.M. (ed.) Thermodynamics, Solubility and Environmental Issues, pp. 299–313. Elsevier, Amsterdam (2007)
Doble, M., Kruthiventi, A.K.: Alternate solvents. In: Doble, M., Kruthiventi, A.K. (eds.) Green Chemistry and Engineering, pp. 93–104. Academic Press, Cambridge (2007)
Ciocirlan, O., Iulian, O.: Properties of pure 1-Butyl-2,3-dimethylimidazolium tetrafluoroborate ionic liquid and its binary mixtures with dimethyl sulfoxide and acetonitrile. J. Chem. Eng. Data. 57, 3142–3148 (2012)
Olivier-Bourbigou, H., Magna, L., Morvan, D.: Ionic liquids and catalysis: recent progress from knowledge to applications. Appl. Catal. A 373, 1–56 (2010)
Song, C., Liu, S., Peng, X., Long, J., Lou, W., Li, X.: Catalytic conversion of carbohydrates to levulinate ester over heteropolyanion-based ionic liquids. Chemsuschem 9, 3307–3316 (2016)
Zhao, D., Wu, M., Kou, Y., Min, E.: Ionic liquids: applications in catalysis. Catal. Today. 74, 157–189 (2002)
Liu, C.Z., Wang, F., Stiles, A.R., Guo, C.: Ionic liquids for biofuel production: opportunities and challenges. Appl. Energy 92, 406–414 (2012)
da Costa Lopes, A.M., João, K.G., Morais, A.R.C., Bogel-Łukasik, E., Bogel-Łukasik, R.: Ionic liquids as a tool for lignocellulosic biomass fractionation. Sustain. Chem. Process. 1, 3 (2013)
Stark, A.: Ionic liquids in the biorefinery: a critical assessment of their potential. Energy Environ. Sci. 4, 19–32 (2011)
Badgujar, K.C., Wilson, L.D., Bhanage, B.M.: Recent advances for sustainable production of levulinic acid in ionic liquids from biomass: Current scenario, opportunities and challenges. Renew. Sustain. Energy Rev. 102, 266–284 (2019)
Ramli, N.A.S., Amin, N.A.S.: Optimization of biomass conversion to levulinic acid in acidic ionic liquid and upgrading of levulinic acid to ethyl levulinate. Bioenergy Res. 10, 50–63 (2017)
Morone, A., Apte, M., Pandey, R.A.: Levulinic acid production from renewable waste resources: Bottlenecks, potential remedies, advancements and applications. Renew. Sustain Energy Rev. 51, 548–565 (2015)
Balan, V.: Current Challenges in Commercially Producing Biofuels from Lignocellulosic Biomass. ISRN Biotechnol. 2014, 1–31 (2014)
Owusu, P.A., Asumadu-Sarkodie, S.: A review of renewable energy sources, sustainability issues and climate change mitigation. Cogent Eng. 3, 1167990 (2016)
He, M.Y., Sun, Y.H., Han, B.X.: Green carbon science: scientific basis for integrating carbon resource processing, utilization, and recycling. Angew. Chem. Int. Ed. 52, 9620–9633 (2013)
https://www.sasa.org.za/sugar_industry/CaneGrowinginSA.aspx. Accessed 05 March 2019
Schmidt, L.M., Mthembu, L.D., Reddy, P., Deenadayalu, N., Kaltschmitt, M., Smirnova, I.: Levulinic acid production integrated into sugarcane bagasse based biorefinery using thermal-enzymatic pretreatment. Ind. Crop. Prod. 99, 172–178 (2017)
Rackemann, D., Doherty, W.: A review on the production of levulinic acid and furanics from sugars. Int. Sugar. J. 115, 28–34 (2012)
Clark, J.H., Budarin, V., Deswarte, F.E.I., Hardy, J.J.E., Kerton, F.M., Hunt, A.J.L., Luque, R., Macquarrie, D.J., Milkowski, K., Rodriguez, A.S.O., Tavener, S.J., White, R.J., Wilson, A.J.: Green chemistry and the biorefinery: A partnership for a sustainable future. Green Chem. 8, 853–886 (2006)
Sluiter, A., Hames, B., Ruiz, R., Scarlata, C., Sluiter, J., Templeton, D., Crocker, D.: Determination of structural carbohydrates and lignin in Biomass, National Renewable Energy Labortaory, NREL/TP-510–4216 (2010)
https://www.chem.ucla.edu/~bacher/Specialtopics/extraction.html). Accessed 15 January 2020
Ortiz-Cervantes, C., García, J.J.: Hydrogenation of levulinic acid to γ-valerolactone using ruthenium nanoparticles. Inorg. Chim. Acta 397, 124–128 (2013)
Hayes, D.J., Ross, J., Hayes, M.H.B., Fitzpatrick, S.W.: The biofine process: production of levulinic acid, furfural and formic acid from lignocellulosic feedstocks. In: Kamm, B., Gruber, P.R., Kamm, M. (eds.) Biorefineries—Industrial Processes and Products: Status Quo and Future Directions, pp. 139–164. Wiley-VCH, Weinheim (2006)
Ishizaki, H., Hasumi, K.: Ethanol production from biomass. In: Tojo, S., Hirasawa, T. (eds.) Research Approaches to Sustainable Biomass Systems, pp. 243–258. Academic Press, Cambridge (2014)
Yi, S., Su, Y., Qi, B., Su, Z., Wan, Y.: Application of response surface methodology and central composite rotatable design in optimization; the preparation condition of vinyltriethoxysilane modified silicalite/polydimethylsiloxane hybrid pervaporation membranes. Sep. Purif. Technol. 71, 252–262 (2010)
Behera, S.K., Meena, H., Chakraborty, S., Meikap, B.C.: Application of response surface methodology (RSM) for optimization of leaching parameters for ash reduction from low-grade coal. Int. J. Min. Sci. Technol. 28, 621–629 (2018)
Bozell, J.J., Petersen, G.R.: 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 (2010)
Chem.libretexts.org. Accessed 06 March 2019
Tong, X., Li, Y.: Efficient and selective dehydration of fructose to 5-hydroxymethylfurfural catalyzed by Bronsted-acidic ionic liquids. Chem. Sustain Chem. 3, 350–355 (2010)
Mukherjee, A., Dumont, M.J., Raghavan, V.: Review: sustainable production of hydroxymethylfurfural and levulinic acid: challenges and opportunities. Biomass Bioenergy 72, 143–183 (2015)
Qi, X., Smith, R.L., Fang, Z.: Production of versatile platform chemical 5- hydroxymethylfurfural from biomass in ionic liquids. In: Fang, Z., Smith Jr., R., Qi, X. (eds.) Production of Biofuels and Chemicals with Ionic liquids: Biofuels Biorefin, pp. 223–254. Springer, Dordrecht (2014)
Nhien, L.C., Long, N.V.D., Kim, S., Lee, M.: Design and assessment of hybrid purification processes through a systematic solvent screening for the production of levulinic acid from lignocellulosic biomass. Ind. Eng. Chem. Res. 55, 5180–5189 (2016)
Rackemann, D.W., Bartley, J.P., Doherty, W.O.S.: Methanesulfonic acid-catalysed conversion of glucose and xylose mixtures to levulinic acid and furfural. Ind. Crop. Prod. 52, 46–57 (2014)
Manzer, L.E.: Catalytic synthesis of α-methylene-γ-valerolactone: a biomass-derived acrylic monomer. Appl. Catal. A 272, 249–256 (2004)
Rodiansono, R., Astuti, M.D., Ghofur, A., Sembiring, K.C.: Catalytic hydrogenation of levulinic acid in water into γ-Valerolactone over bulk structure of inexpensive intermetallic Ni-Sn alloy catalysts. Bull. Chem. React. Eng. Catal. 10, 192–200 (2015)
Li, W., Xie, J., Lin, H., Zhou, Q.: Highly efficient hydrogenation of biomass-derived levulinic acid to γ-valerolactone catalysed by iridium pincer complexes. Green Chem. 14, 2388–2390 (2012)
Feng, H.J., Li, X.C., Qian, H., Zhang, Y.F., Zhang, D.H., Zhao, D., Hong, S.G., Zhang, N.: Efficient and sustainable hydrogenation of levulinic-acid to gamma-valerolactone in aqueous solution over acid-resistant CePO4/Co2 P catalysts. Green Chem. 21, 1743–1756 (2019)
de Haan, J.E.: Hydrogenation of levulinic acid to valerolactone in a continuous packed bed reactor. Master’s Thesis, University of Groningen (2013)
Acknowledgements
The authors would like to show gratitude to National Research Foundation (NRF), L’Oréal-UNESCO for Women in Science Sub-Saharan Africa Regional fellowships and Durban University of Technology for financial support. South Milling Research Institute (SMRI) for the provision of Sugarcane Bagasse.
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Mthembu, L.D., Lokhat, D. & Deenadayalu, N. Valorization of Sugarcane Bagasse to a Platform Chemical (Levulinic Acid) Catalysed by 1-Butyl-2,3-dimethylimidazolium Tetrafluoroborate ([BMMim][BF4]). Waste Biomass Valor 12, 199–209 (2021). https://doi.org/10.1007/s12649-020-00997-4
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DOI: https://doi.org/10.1007/s12649-020-00997-4