Abstract
The catalytic conversion of renewable biomass-derived aldehydes and ketones to aviation fuels is very attractive for sustainable development. We provided insight into the production of aviation fuel from typical biomass carbonyl platform compounds (furfural, acetone, butanone, and butyraldehyde) by aldol condensation followed with hydrodeoxygenation over bifunctional catalyst Ni/Mg–Al-O/AC, focusing on the mechanism of condensation reaction. It was found that high temperature is not only conducive to aggravate the depth of aldehyde ketone condensation reaction, further convert dimer to trimer, but also promote its self-condensation. The optimal condensation temperature of aldehydes and ketones under this idea was 170 °C, the carbon number range of the jet fuel intermediates was C7–C14, and the yield of condensates reached 79.23%. In order to explore the mechanism in the aldol condensation of aldehydes and ketones, the evolution law of typical products was studied by controlling the reaction time, and seven main condensation pathways were proposed. The ratios of aldehyde/ketone in the reactant and the ratios of each component within the aldehyde and ketone were adjusted, and it was found that the reaction priority of chain aldehydes is the highest in this reaction system, and the reaction priority of small-molecule ketones with low carbon number is higher than that of high carbon number ketones. The presence of long-chain groups in the hydrogenated oil increased the density of jet fuel, and it has a higher calorific value, which are very promising as aviation fuels or additives of aviation bio-fuels.
Similar content being viewed by others
References
Liu G, Yan B, Chen G (2013) Technical review on jet fuel production. Renew Sustain Energy Rev 25:59–70. https://doi.org/10.1016/j.rser.2013.03.025
Karmakar B, Samanta S, Halder G (2020) Delonix two-step biodiesel production from Pongamia pinnata oil using methanol and 2-propanol. J Clean Prod 255:120313. https://doi.org/10.1016/j.jclepro.2020.120313
Huber GW, Iborra S, Corma A (2006) Synthesis of transportation fuels from biomass: chemistry, catalysts, and engineering. Chem Rev 106:4044–4098. https://doi.org/10.1021/cr068360d
Chowdari RK, Agarwal S, Heeres HJ (2019) Hydrotreatment of kraft lignin to alkylphenolics and aromatics using Ni, Mo, and W phosphides supported on activated carbon. ACS Sustain Chem Eng 7(2):2044–2055. https://doi.org/10.1021/acssuschemeng.8b04411
Faba L, Díaz E, Ordóñez S (2012) Aqueous-phase furfural-acetone aldol condensation over basic mixed oxides. Appl Catal B: Environ 113–114. https://doi.org/10.1016/j.apcatb.2011.11.039
Sheng X, Li N, Li G, Wang W, Yang J, Cong Y, Zhang T (2015) Synthesis of high-density aviation fuel with cyclopentanol derived from lignocellulose. Sci Rep 5:9565. https://doi.org/10.1038/srep09565
Sacia ER, Deaner MH, Louie YL, Bell AT (2015) Synthesis of biomass-derived methylcyclopentane as a gasoline additive via aldol condensation/hydrodeoxygenation of 2,5-hexanedione. Green Chem 17(4):2393–2397. https://doi.org/10.1039/c4gc02292k
Dedsuksophon W, Faungnawakij K, Champreda V, Laosiripojana N (2011) Hydrolysis/dehydration/aldol-condensation/hydrogenation of lignocellulosic biomass and biomass-derived carbohydrates in the presence of Pd/WO3–ZrO2 in a single reactor. Biores Technol 102(2):2040–2046. https://doi.org/10.1016/j.biortech.2010.09.073
Kong X, Wei XJ, Li LP, Fang Z, Lei H (2021) Production of liquid fuel intermediates from furfural via aldol condensation over La2O2CO3-ZnO-Al2O3 catalyst. Catal Commun 149:106207. https://doi.org/10.1016/j.catcom.2020.106207
Xing R, Subrahmanyam AV, Olcay H, Qi W, van Walsum GP, Pendse H, Huber GW (2010) Production of jet and diesel fuel range alkanes from waste hemicellulose-derived aqueous solutions. Green Chem 12(11):1933–1946. https://doi.org/10.1039/C0GC00263A
Liu Y, Li G, Hu Y, Wang A, Lu F, Zou JJ, Zhang T (2019) Integrated conversion of cellulose to high-density aviation fuel. Joule 3(4):1028–1036. https://doi.org/10.1016/j.joule.2019.02.005
Xu X, Meng H, Lu Y, Li C (2018) Aldol condensation of refluxing acetone on CaC2 achieves efficient coproduction of diacetone alcohol, mesityl oxide and isophorone. RSC Adv 8(53):30610–30615. https://doi.org/10.1039/C8RA05965A
Liang N, Zhang X, An H, Zhao X, Wang Y (2015) Direct synthesis of 2-ethylhexanol via n-butanal aldol condensation–hydrogenation reaction integration over a Ni/Ce-Al2O3 bifunctional catalyst. Green Chem 17(5):2959–2972. https://doi.org/10.1039/C5GC00223K
Ao L, Zhao W, Guan YS, Wang DK, Liu KS, Guo TT, Wei XY (2019) Efficient synthesis of C15 fuel precursor by heterogeneously catalyzed aldol-condensation of furfural with cyclopentanone. RSC Advances 9(7):3661–3668. https://doi.org/10.1039/C8RA09517E
Wang Y, Makkee M (2018) The influence of CO2 on NO reduction into N2 over reduced ceria-based catalyst. Appl Catal B 221:196–205. https://doi.org/10.1016/j.apcatb.2017.09.013
Xu J, Jiang J, Hse C, Shupe TF (2012) Renewable chemical feedstocks from integrated liquefaction processing of lignocellulosic materials using microwave energy. Green Chem 14(10):2821–2830. https://doi.org/10.1039/c2gc35805k
Vila A, Graña AM, Mosquera RA (2002) Electron density characterisation of intermolecular interactions in the formaldehyde dimer and trimer. Chem Phys 281(1):11–22. https://doi.org/10.1016/S0301-0104(02)00590-6
Huang XM, Zhang Q, Wang TJ, Liu QY, Ma Ll, Zhang Q (2002) Production of jet fuel intermediates from furfural and acetone by aldol condensation over MgO/NaY. J Fuel Chem Technol 40(8):973–978. https://doi.org/10.1016/S1872-5813(12)60035-8
Vashishtha M, Mishra M, Shah DO (2003) A novel approach for selective cross aldol condensation using reusable NaOH-cationic micellar systems. Appl Catal A 466:38–44. https://doi.org/10.1016/j.apcata.2013.06.015
Bredihhin A, Salmar S, Vares L (2018) Route for conversion of furfural to ethylcyclopentane. ACS Omega 3(8):10211–10215. https://doi.org/10.1021/acsomega.8b00588
Kim M, Park J, Kannapu H, Suh YW (2017) Cross-aldol condensation of acetone and n-butanol into aliphatic ketones over supported Cu catalysts on ceria-zirconia. Catalysts 7:249. https://doi.org/10.3390/catal7090249
Barrett CJ, Chheda JN, Huber GW, Dumesic JA (2016) Single-reactor process for sequential aldol-condensation and hydrogenation of biomass-derived compounds in water. Appl Catal B 66(1–2):111–118. https://doi.org/10.1016/j.apcatb.2006.03.001
West RM, Liu ZY, Peter M, Dumesic JA (2008) Liquid alkanes with targeted molecular weights from biomass-derived carbohydrates. Chemsuschem 1(5):417–424. https://doi.org/10.1002/cssc.200800001
Tsuji H, Yagi F, Hattori H, Kita H (1994) Self-condensation of n-butyraldehyde over solid base catalysts. J Catal 148(2):759–770. https://doi.org/10.1006/jcat.1994.1262
Salvapati GS, Ramanamurty KV (1989) Selective catalytic self-condensation of acetone. Janardanarao M J Mol Catal 54(1):9–30. https://doi.org/10.1016/0304-5102(89)80134-8
Nikolopoulos AA, Jang BWL, Spivey JJ (2005) Acetone condensation and selective hydrogenation to MIBK on Pd and Pt hydrotalcite-derived MgAl mixed oxide catalysts. Appl Catal A 296(1):128–136. https://doi.org/10.1016/j.apcata.2005.08.022
Zhao Y, Xu H, Lu K, Qu Y, Zhu L, Wang S (2019) Dehydration of xylose to furfural in butanone catalyzed by Brønsted-Lewis acidic ionic liquids. Energy Sci Eng 7(5):2237–2246. https://doi.org/10.1002/ese3.444
Wu L, Moteki T, Gokhale AA, Flaherty DW, Toste FD (2016) Production of fuels and chemicals from biomass: condensation reactions and beyond. Chemistry 1(1):32–58. https://doi.org/10.1016/j.chempr.2016.05.002
Belokon YN, Bulychev AG, Vitt SV, Struchkov YT, Batsanov AS, Timofeeva TV, Lysova LA (1985) General method of diastereo- and enantioselective synthesis of β-hydroxy-α-amino acids by condensation of aldehydes and ketones with glycine. J Am Chem Soc 107(14):4252–4259. https://doi.org/10.1021/ja00300a030
Shao S, Dong W, Li X, Zhang H, Xiao R, Cai Y (2019) Solvent-free synthesis of jet fuel by aldol condensation and hydroprocessing of cyclopentanone as biomass-derivates. J Clean Prod 250:119459. https://doi.org/10.1016/j.jclepro.2019.119459
Li Y, Liu X, An H, Zhao X, Wang Y (2016) One-pot sequential aldol condensation and hydrogenation of n-butyraldehyde to 2-ethylhexanol. Ind Eng Chem Res 55(22):6293–6299. https://doi.org/10.1021/acs.iecr.6b00828
Zhao C, Kou Y, Lemonidou AA, Li X, Lercher JA (2009) Highly selective catalytic conversion of phenolic bio-oil to alkanes. Angew Chem Int Ed 48(22):3987–3990. https://doi.org/10.1002/ese3.444
Norskov J, Niemantsverdriet H (2015) Special issue: the impact of heliotrope on catalysis. J Catal 328:1–1. https://doi.org/10.1016/j.jcat.2015.04.027
Xie J, Zhang L, Zhang X, Han P, Xie J, Pan L, Zou JJ\ (2018) Synthesis of high-density and low-freezing-point jet fuel using lignocellulose-derived isophorone and furanic aldehydes. Sustain Energy Fuels 2 https://doi.org/10.1039/C8SE00197A
Funding
This study was currently supported by Natural Science Foundation of Jiangsu Province (BK20201420) and China Postdoctoral Science Foundation (2018M630495, 2019T120375).
Author information
Authors and Affiliations
Corresponding author
Additional information
Publisher's note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Rights and permissions
About this article
Cite this article
Li, Z., Shao, S., Hu, X. et al. Insight into the production of aviation fuel by aldol condensation of biomass-derived aldehydes and ketones followed by hydrogenation. Biomass Conv. Bioref. 14, 7915–7926 (2024). https://doi.org/10.1007/s13399-022-03083-y
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s13399-022-03083-y