Thermochemical Property Predictions in Biomass Transformation to Fuel Components and Value-added Chemicals
DOI:
https://doi.org/10.54963/neea.v1i3.70Keywords:
Thermochemical calculation, Value added chemicals, FuelsAbstract
Biomass transformation to fuel and platform chemicals is of an immense interest in the world. The thermochemical data for various reactions involved during biomass transformations to fuel components, fuels and platform chemicals have been investigated using highly accurate Gaussian-4 (G-4) method. Glucose to 5-hydroxymethyl furfural (5-HMF) conversion is a two-step pathway, where first step, glucose isomerization to fructose is highly endothermic with high activation energies. 5-HMF upgradation can be carried through hydrogenation, oxidation, condensation and rehydration. Upgradation of HMF to fuel and value-added chemicals (VAC) is an industrially important process that can reduce the demand of petrochemical based products. Thermochemical calculations predict the hydrogenation of 5-HMF to 2,5 dimethyl furan (2,5 DMF) is feasible and follow either pathways with dihydroxy methyl furan (DHMF) and methyl furan (MF) as intermediates. The total Gibb’s free energy difference for the 5-HMF transformation to 2,5 DMF is highly exothermic. The condensation, rehydration and oxidation reactions of 5-HMF also predicted to be feasible and highly exothermic in nature. That can have potential application in industrial processes. Ethanol is mixed with petrol to run the vehicle on reduced fuel. Ethanol can be obtained from glucose following glycolysis pathway, breaking C-6 sugar to two C-3 sugars. Glyceraldehyde and pyruvic acid are the intermediates in the glycolysis cycle with positive Gibbs free energy change, hence requiring high temperature.
References
Gallezot, P., 2012. Conversion of Biomass to Selected Chemical Products. Chemical Society Reviews. 41(4), 1538. DOI: https://doi.org/10.1039/c1cs15147a
Liu, Z., Saydaliev, H.B., Lan, J., et al., 2022. Assessing the Effectiveness of Biomass Energy in Mitigating CO2 Emissions: Evidence from Top-10 Biomass Energy Consumer Countries. Renewable Energy. 191, 842-851. DOI: https://doi.org/10.1016/j.renene.2022.03.053
Parveen, F., Patra, T., Upadhyayula, S., 2016. Hydrolysis of Microcrystalline Cellulose Using Functionalized Bronsted Acidic Ionic Liquids – A Comparative Study. Carbohydrate Polymers. 135, 280-284. DOI: https://doi.org/10.1016/j.carbpol.2015.08.039
Parveen, F., Gupta, K., Upadhyayula, S., 2017. Synergistic Effect of Chloro and Sulphonic Acid Groups on the Hydrolysis of Microcrystalline Cellulose under Benign Conditions. Carbohydrate Polymers. 159, 146-151. DOI: https://doi.org/10.1016/j.carbpol.2016.12.021
Sultana, A., Fujitani, T., 2017. Conversion of Levulinic Acid to BTX over Different Zeolite Catalysts. Catalysis Communications. 88, 26-29. DOI: https://doi.org/10.1016/j.catcom.2016.09.023
Jaatinen, S.K., Karinen, R.S., Lehtonen, J.S., 2016. Liquid Phase Furfural Hydrotreatment to 2-Methylfuran on Carbon Supported Nickel Catalyst - Effect of Process Conditions. ChemistrySelect. 1(16), 5363- 5373. DOI: https://doi.org/10.1002/slct.201601333
Parveen, F., Upadhyayula, S., 2017. Efficient Conversion of Glucose to HMF Using Organocatalysts with Dual Acidic and Basic Functionalities - A Mechanistic and Experimental Study. Fuel Processing Technology. 162, 30-36. DOI: https://doi.org/10.1016/j.fuproc.2017.03.021
Parveen, F., Jaiswal, M., Upadhyayula, S., 2018. Effect of Linkers (Aliphatic/ Aromatic) and Anions on the Activity of Sulfonic Acid Functionalized Ionic Liquids towards Catalyzing the Hydrolysis of Microcrystalline Cellulose-an Experimental and Theoretical Study. Renewable Energy. 121, 590-596. DOI: https://doi.org/10.1016/j.renene.2018.01.079
Parveen, F., Ahmad, K., Upadhyayula, S., 2019. Catalytic Conversion of Biomass Derived Cellulose to 5-Hydromethyl Furfural. Integrating Green Chemistry and Sustainable Engineering; John Wiley & Sons, Inc. pp. 113-163. DOI: https://doi.org/10.1002/9781119509868.ch5
Chamoli, S., Upadhyayula, S., Parveen, F., et al., 2022. Biofuels and Fine Chemicals From Lignocellulosic Biomass: A Sustainable and Circular Economy. Handbook of Biomass Valorization for Industrial Applications. pp. 41-53. DOI: https://doi.org/https://doi.org/10.1002/ 9781119818816.ch3
Verevkin, S.P., 2022. Weaving a Web of Reliable Thermochemistry around Lignin Building Blocks: Phenol, Benzaldehyde, and Anisole. Journal of Thermal Analysis and Calorimetry. 147(11), 6073-6085. DOI: https://doi.org/10.1007/s10973-021-10924-x
Yao, Z., Cai, D., Chen, X., et al., 2022. Thermal Behavior and Kinetic Study on the Co-Pyrolysis of Biomass with Polymer Waste. Biomass Conversion and Biorefinery. DOI: https://doi.org/10.1007/s13399-022-02480-7
Momany, F.A., Appell, M., Strati, G., et al., 2004. B3LYP/6-311++G** Study of Monohydrates of ??- And ??-D-Glucopyranose: Hydrogen Bonding, Stress Energies, and Effect of Hydration on Internal Coordinates. Carbohydrate Research. 339(3), 553-567. DOI: https://doi.org/10.1016/j.carres.2003.10.013
Appell, M., Strati, G., Willett, J.L., et al., 2004. B3LYP/6-311++G** Study of a- and b-D-Glucopyranose and 1,5-Anhydro-D-Glucitol: 4C1 and 1C 4 Chairs, 3,OB and B3,O Boats, and Skew-Boat Conformations. Carbohydrate Research. 339(3), 537-551. DOI: https://doi.org/10.1016/j.carres.2003.10.014
Raju, R.K., Ramraj, A., Hillier, I.H., et al., 2009. Carbohydrate-Aromatic Pi Interactions: A Test of Density Functionals and the DFT-D Method. Physical Chemistry Chemical Physics. 11, 3411-3416. DOI: https://doi.org/10.1039/b822877a
Csonka, G.I., French, A.D., Johnson, G.P., et al., 2009. Evaluation of Density Functionals and Basis Sets for Carbohydrates. Journal of Chemical Theory & Computation. 5(4), 679-692. DOI: https://doi.org/10.1021/ct8004479
Ma, B., Schaefer, H.F., Allinger, N.L., 1998. Theoretical Studies of the Potential Energy Surfaces and Compositions of the d -Aldo- and d -Ketohexoses. Journal of the American Chemical Society. 120(14), 3411-3422. DOI: https://doi.org/10.1021/ja9713439
Cramer, C.J., Truhlar, D.G., 1993. Quantum Chemical Conformational Analysis of Glucose in Aqueous Solution. Journal of the American Chemical Society. 115(13), 5745-5753. DOI: https://doi.org/10.1021/ja00066a046
Xiang, Q., Lee, Y.Y., Torget, R.W., 2004. Kinetics of Glucose Decomposition during Dilute-Acid Hydrolysis of Lignocellulosic Biomass. Applied Biochemistry and Biotechnology. 113-116(1), 1127-1138. DOI: https://doi.org/10.1385/ABAB:115:1-3:1127
Chang, C., MA, X., CEN, P., 2006. Kinetics of Levulinic Acid Formation from Glucose Decomposition at High Temperature. Chinese Journal of Chemical Engineering. 14(5), 708-712. DOI: https://doi.org/10.1016/S1004-9541(06)60139-0
Zhao, H., Holladay, J.E., Brown, H., et al., 2007. Metal Chlorides in Ionic Liquid Solvents Convert Sugars to 5-Hydroxymethylfurfural. Science. 316(15), 1597-1600.
Parveen, F., Patra, T., Upadhyayula, S., 2018. A Structure-Activity Relationship Study Using DFT Analysis of Bronsted-Lewis Acidic Ionic Liquids and Synergistic Effect of Dual Acidity in One-Pot Conversion of Glucose to Value-Added Chemicals. New Journal of Chemistry. 42(2), 1423-1430. DOI: https://doi.org/10.1039/c7nj02364b
Román-Leshkov, Y., Barrett, C.J., Liu, Z.Y., et al., 2007. Production of Dimethylfuran for Liquid Fuels from Biomass-Derived Carbohydrates. Nature. 447(7147), 982-985. DOI: https://doi.org/10.1038/nature05923
West, R.M., Liu, Z.Y., Peter, M., et al., 2008. Liquid Alkanes with Targeted Molecular Weights from Biomass-Derived Carbohydrates. ChemSusChem. 1(5), 417-424. DOI: https://doi.org/10.1002/cssc.200800001
Chheda, J.N., Dumesic, J.A., 2007. An Overview of Dehydration, Aldol-Condensation and Hydrogenation Processes for Production of Liquid Alkanes from Biomass-Derived Carbohydrates. Catalysis Today. 123(1-4), 59-70. DOI: https://doi.org/10.1016/j.cattod.2006.12.006
Verevkin, S.P., Emel’yanenko, V.N., Stepurko, E.N., et al., 2009. Biomass-Derived Platform Chemicals: Thermodynamic Studies on the Conversion of 5-Hydroxymethylfurfural into Bulk Intermediates. Industrial & Engineering Chemistry Research. 48(22), 10087-10093. DOI: https://doi.org/10.1021/ie901012g
Kumar, K., Khatri, V., Parveen, F., et al., 2020. Synthesis of an Oxygenated Fuel Additive from a Waste Biomass Derived Aldehyde Using a Green Catalyst: An Experimental and DFT Study. Sustainable Energy & Fuels. 4(6), 2924-2936. DOI: https://doi.org/10.1039/d0se00100g
Kumar, K., Parveen, F., Patra, T., et al., 2018. Hydrothermal Conversion of Glucose to Levulinic Acid Using Multifunctional Ionic Liquids: Effects of Metal Ion Co-Catalysts on the Product Yield. New Journal of Chemistry. 42(1), 228-236. DOI: https://doi.org/10.1039/c7nj03146g
Van Mourik, T., Bühl, M., Gaigeot, M.P., 2014. Density Functional Theory across Chemistry, Physics and Biology. Philosophical Transactions of the Royal Society A: Mathematical, Physical and Engineering Sciences. 372(2011). DOI: https://doi.org/10.1098/rsta.2012.0488
Curtiss, L.A., Redfern, P.C., Raghavachari, K., 2007. Gaussian-4 Theory. Journal of Chemical Physics. 126(8). DOI: https://doi.org/10.1063/1.2436888
Curtiss, L.A., Redfern, P.C., Raghavachari, K., 2005. Assessment of Gaussian-3 and Density-Functional Theories on the G3/05 Test Set of Experimental Energies. The Journal of Chemical Physics. 123(12). DOI: https://doi.org/10.1063/1.2039080
Shandilya, A., Ganesan, M., Parveen, F., et al., 2016. Molecular Basis for the Affinity and Specificity in the Binding of Five-Membered Iminocyclitols with Glycosidases: An Experimental and Theoretical Synergy. Carbohydrate Research. 429, 87-97. DOI: https://doi.org/10.1016/j.carres.2016.03.010
Lange, J.P., Van Der Heide, E., Van Buijtenen, J., et al., 2012. Furfural-A Promising Platform for Lignocellulosic Biofuels. ChemSusChem. 5(1), 150-166. DOI: https://doi.org/10.1002/cssc.201100648
Hu, E., Hu, X., Wang, X., et al., 2012. On the Fundamental Lubricity of 2,5-Dimethylfuran as a Synthetic Engine Fuel. Tribology International. 55, 119-125. DOI: https://doi.org/10.1016/j.triboint.2012.06.005
Shanks, B.H., Keeling, P.L., 2017. Bioprivileged Molecules: Creating Value from Biomass. Green Chemistry. 19(14), 3177-3185. DOI: https://doi.org/10.1039/C7GC00296C
Wu-gao, Z., Li, D., Zhen, H., et al., 2005. Physico-Chemical Properties of Ethanol – Diesel Blend Fuel and Its Effect on Performance and Emissions of Diesel Engines. 30, 967-976. DOI: https://doi.org/10.1016/j.renene.2004.07.010
Downloads
Published
How to Cite
Issue
Section
License
Copyright (c) 2022 Firdaus Parveen
This work is licensed under a Creative Commons Attribution 4.0 International License.
Copyright
The authors shall retain the copyright of their work but allow the Publisher to publish, copy, distribute, and convey the work.
License
New Energy Exploitation and Application (NEEA) publishes accepted manuscripts under Creative Commons Attribution 4.0 International (CC BY 4.0). Authors who submit their papers for publication by New Energy Exploitation and Application (NEEA) agree to have the CC BY 4.0 license applied to their work, and that anyone is allowed to reuse the article or part of it free of charge for any purpose, including commercial use. As long as the author and original source is properly cited, anyone may copy, redistribute, reuse and transform the content.
