Chinese Journal of Chemical Engineering ›› 2025, Vol. 80 ›› Issue (4): 89-99.DOI: 10.1016/j.cjche.2025.01.003
Previous Articles Next Articles
Yaqi Qu, Hualiang An, Xinqiang Zhao, Yanji Wang
Received:
2024-08-14
Revised:
2025-01-15
Accepted:
2025-01-17
Online:
2025-03-03
Published:
2025-04-28
Contact:
Hualiang An,E-mail:anhl@hebut.edu.cn;Xinqiang Zhao,E-mail:zhaoxq@hebut.edu.cn
Supported by:
Yaqi Qu, Hualiang An, Xinqiang Zhao, Yanji Wang
通讯作者:
Hualiang An,E-mail:anhl@hebut.edu.cn;Xinqiang Zhao,E-mail:zhaoxq@hebut.edu.cn
基金资助:
Yaqi Qu, Hualiang An, Xinqiang Zhao, Yanji Wang. Heterogeneously catalyzed self-condensation of n-butanal[J]. Chinese Journal of Chemical Engineering, 2025, 80(4): 89-99.
Yaqi Qu, Hualiang An, Xinqiang Zhao, Yanji Wang. Heterogeneously catalyzed self-condensation of n-butanal[J]. 中国化学工程学报, 2025, 80(4): 89-99.
[1] S.B. Li, J.X. Zhang, H.L. An, G.R. Wang, X.Q. Zhao, Y.J. Wang, NiO-MnO2/Nb2O5-TiO2 catalyzed reaction integration of butanal self-condensation and successive hydrogenation and its kinetics, J. Chem. Technol. Biotechnol. 96 (6) (2021) 1553-1560. [2] N. Liang, X.L. Zhang, H.L. An, X.Q. Zhao, Y.J. Wang, Direct synthesis of 2-ethylhexanol via n-butanal aldol condensation-hydrogenation reaction integration over a Ni/Ce-Al2O3 bifunctional catalyst, Green Chem. 17 (5) (2015) 2959-2972. [3] Y. Li, X.H. Liu, H.L. An, X.Q. Zhao, Y.J. Wang, One-pot sequential aldol condensation and hydrogenation of n-butyraldehyde to 2-ethylhexanol, Ind. Eng. Chem. Res. 55 (22) (2016) 6293-6299. [4] J.H. Clark, V. Budarin, F.E.I. Deswarte, J.J.E. Hardy, F.M. Kerton, A.J. Hunt, R. Luque, D.J. MacQuarrie, K. Milkowski, A. Rodriguez, O. Samuel, S.J. Tavener, R.J. White, A.J. Wilson, Green chemistry and the biorefinery: a partnership for a sustainable future, Green Chem. 8 (10) (2006) 853-860. [5] J. He, Q. Qiang, S.M. Liu, K. Song, X.W. Zhou, J. Guo, B. Zhang, C.Z. Li, Upgrading of biomass-derived furanic compounds into high-quality fuels involving aldol condensation strategy, Fuel 306 (2021) 121765. [6] J. Cueto, D. de la Calle, M. del Mar Alonso-Doncel, E.A. Giner, R.A. Garcia-Munoz, D.P. Serrano, Enhanced production of jet fuel precursors via furfural/cyclopentanone aldol condensation by synergistic pairing TiO2 with nano-ZSM-5 zeolite, Bioresour. Technol. 418 (2025) 131877. [7] S. Miao, H.L. An, X.Q. Zhao, Y.J. Wang, Catalytic performance of Cu-Mg-Al in the one-step synthesis of 2-ethylhexanol from n-butyraldehyde, React. Kinet. Mech. Catal. 125 (2) (2018) 773-788. [8] Y. Zhang, The study of new catalytic technology of self-condensation of butanal to 2-ethylhexenal, Master Thesis, Shanghai Normal University: Shanghai, China, 2010. [9] H. Lou, H. Sun, J. Duan, Y. Ding, J. Han, W. Li, X. Zheng, A process method for preparing 2-ethyl-2-hexenal via n-butanal self-condensation catalyzed by MgO catalyst, CN 102070419A (2011). [10] X. Liu, L. Wu, H. An, X. Zhao, Y. Wang, Aldol self-condensation of n-butyraldehyde to 2-ethyl-2-hexenal catalyzed by KF-γ-Al2O3, Acta Pet. Sin., (Pet. Process. Sect.) 31 (2015) 1332-1337. [11] Y. Watanabe, K. Sawada, M. Hayashi, A green method for the self-aldol condensation of aldehydes using lysine, Green Chem. 12 (3) (2010) 384-386. [12] T. Jose, N. Sudheesh, R.S. Shukla, Amino functionalized chitosan as a catalyst for selective solvent-free self-condensation of linear aldehydes, J. Mol. Catal. A Chem. 333 (1-2) (2010) 158-166. [13] Y. Li, n-Butyraldehyde self-condensation catalyzed by chitosan; Master Thesis, Hebei University of Technology,Tianjin, China, 2017. [14] X.X. Han, Y. Li, H.L. An, X.Q. Zhao, Y.J. Wang, Chitosan-catalyzed n-butyraldehyde self-condensation reaction mechanism and kinetics, Chin. J. Chem. Eng. 27 (10) (2019) 2447-2454. [15] J. Zhang, Y. Li, B. Hu, H. An, X. Zhao, Y. Wang, Catalytic performance of chitosan for n-butyraldehyde aldol self-condensation, J. Chem. Eng. Chin. Univ. 2020, 34(5): 1189-1195. [16] A.G. Thome, N. Osakoo, J. Wittayakun, F. Roessner, Base modified organic mesoporous silicas, their characterization and application in the aldol reaction of n-butanal, Mol. Catal. 531 (2022) 112670. [17] S. Erdmann, A.G. Thome, J. Wittayakun, F. Roessner, Kinetic investigation of the aldol condensation of n-butanal on mesoporous and macro-mesoporous heterogeneous catalysts, Mol. Catal. 559 (2024) 114026. [18] I.V. Kozhevnikov, Catalysis by heteropoly acids and multicomponent polyoxometalates in liquid-phase reactions, Chem. Rev. 98 (1) (1998) 171-198. [19] J.R. Li, Z. Yang, S.W. Li, Q.P. Jin, J.S. Zhao, Review on oxidative desulfurization of fuel by supported heteropolyacid catalysts, J. Ind. Eng. Chem. 82 (2020) 1-16. [20] C.N. Chen, X.H. Liu, H.L. An, X.Q. Zhao, Y.J. Wang, N-Butyraldehyde aldol self-condensation catalyzed by H4SiW12O40/SiO2, CIESC J. 65 (6) (2014) 2106-2112. (in Chinese). [21] N.E. Musko, J.D. Grunwaldt, Heterogeneously catalysed aldol reactions in supercritical carbon dioxide as innovative and non-flammable reaction medium, Top. Catal. 54 (16) (2011) 1115. [22] B. Li, n-Butyraldehyde/n-valeraldehyde self-condensation catalyzted by MIL-100(Fe) and MIL-100(Fe)-encapsulated H4SiW12O40; Master Thesis, Hebei University of Technology: Tianjin, China, 2017. [23] Y. Shi, B. Li, H. An, X. Zhao, Y. Wang, Preparation of H4SiW12O40@MIL-100 (Fe) and its catalytic performance in the self-condensation of n-butyraldehyde, Acta Pet. Sin., (Pet. Process. Sect.) 35 (2019) 660-668. [24] H. Tsuji, F. Yagi, H. Hattori, H. Kita, Self-condensation of n-butyraldehyde over solid base catalysts, J. Catal. 148 (2) (1994) 759-770. [25] X. Zhao, N. Liang, H. An, Y. Wang, A process method for preparing 2-ethyl-2-hexenal via n-butanal self-condensation catalyzed by solid acid catalyst. ZL 201210507185.6 (2015). [26] N. Liang, Research on catalysts for n-butanal aldol condensation and for n-butanal aldol condensation-hydrogenation reaction integration; Master Thesis, Hebei University of Technology: Tianjin, China, 2014. [27] C. Xiong, Reaction kinetics of n-butanal aldol condensation over Ce-Al2O3 catalyst and its catalytic stability; Master Thesis, Hebei University of Technology: Tianjin, China, 2016. [28] C. Xiong, N. Liang, H.L. An, X.Q. Zhao, Y.J. Wang, N-Butyraldehyde self-condensation catalyzed by Ce-modified γ-Al2O3, RSC Adv. 5 (125) (2015) 103523-103533. [29] X. Liu, Solid catalysts for n-butanal aldol condensation and for one-pot sequential aldol condensation-hydrogenation to 2-ethylhexenanol; Master Thesis, Hebei University of Technology: Tianjin, China, 2015. [30] X.H. Liu, Y. Wang, H.L. An, X.Q. Zhao, Y.J. Wang, Synthesis of 2-ethyl-2-hexenal via n-butanal self-condensation catalyzed by La-Al2O3, CIESC J. 67 (5) (2016) 1884-1891.(in Chinese). [31] D.L. Sun, Y. Yamada, S. Sato, Amorphous SiO2 catalyst for vapor-phase aldol condensation of butanal, Appl. Catal. A Gen. 570 (2019) 113-119. [32] X. He, H. An, X. Zhao, Y. Wang, Effects of crystal forms of TiO2 on n-butanal self-condensation, J. Chem. Eng. Chin. Univ. 31 (2017) 1103-1112. [33] Y. Zhu, X. He, H. An, Y. Geng, X. Zhao, Y. Wang, Optimization of gas phase n-butyraldehyde self-condensation catalyzed by TiO2 in a fixed bed reactor, J. Chem. Eng. Chin. Univ. 32 (2018) 1338-1344. [34] X. He, Catalytic performance of TiO2 for n-butanal self-condensation; Master Thesis, Hebei University of Technology: Tianjin, China, 2017. [35] D.L. Sun, S. Moriya, Y. Yamada, S. Sato, Vapor-phase self-aldol condensation of butanal over Ag-modified TiO2, Appl. Catal. A Gen. 524 (2016) 8-16. [36] P. Moggi, G. Albanesi, Methylolation and aldol condensation in gas phase by heterogeneous catalysis, React. Kinet. Catal. Lett. 22 (1) (1983) 247-251. [37] P. Moggi, G. Albanesi, Gas phase aldol condensation of n-butyraldehyde to 2-ethylhexenal, Appl. Catal. 68 (1) (1991) 285-300. [38] T. Yasuhiko, N. Toshio, Production of 2-ethylhexenal, JP Patent S61167634, 1986. [39] H.E. Swift, J.E. Bozik, F.E. Massoth, Vapor-phase aldol condensation of n-butyraldehyde using a reduced tin-silica catalyst, J. Catal. 15 (4) (1969) 407-416. [40] R.L. Vekariya, A review of ionic liquids: applications towards catalytic organic transformations, J. Mol. Liq. 227 (2017) 44-60. [41] H.B. Xing, T. Wang, Z.H. Zhou, Y.Y. Dai, The sulfonic acid-functionalized ionic liquids with pyridinium cations: Acidities and their acidity-catalytic activity relationships, J. Mol. Catal. A Chem. 264 (1-2) (2007) 53-59. [42] X. Zhang, Environmentally friendly catalysts for n-butayraldehyde aldol condensation and for the reaction integration of the condensation-hydrogenation; Master Thesis, Hebei University of Technology: Tianjin, China, 2015. [43] X.L. Zhang, H.L. An, H.Q. Zhang, X.Q. Zhao, Y.J. Wang, n-butyraldehyde self-condensation catalyzed by sulfonic acid functionalized ionic liquids, Ind. Eng. Chem. Res. 53 (43) (2014) 16707-16714. [44] X. Zhao, C. Chen, H. An, Y. Wang, A process method for preparing 2-ethyl-2-hexenal via n-butanal self-condensation catalyzed by acidic ionic liquid. ZL 201210203372.5 (2014). [45] B.J. Arena, J.S. Holmgren, 2-Eehyl-2-hexenal by aldol condensation of butyraldehyde in a continuous process, US Patent 5144089 (1992). [46] A.A. Schutz, Process for aldol condensation, US Patent 5055620 (1991). [47] R. Teissier, M. Fournier, Catalyst for obtaining β-hydroxy and/or α,β-unsaturated carbonyl compounds, US Patent 6271171 (2001). [48] G.J. Kelly, Aldol condensation, US Patent 0044558A1 (2001). [49] W.Q. Shen, G.A. Tompsett, R. Xing, W. Curtis Conner, G.W. Huber, Vapor phase butanal self-condensation over unsupported and supported alkaline earth metal oxides, J. Catal. 286 (2012) 248-259. [50] E.J. Rode, P.E. Gee, L.N. Marquez, T. Uemura, M. Bazargani, Aldol condensation of butanal over alkali metal zeolites, Catal. Lett. 9 (1) (1991) 103-113. [51] D. Sankaranarayanapillai Shylesh, D. Hanna, J. Gomes, S. Krishna, D.C.G. Canlas, P. Martin Head-Gordon, P.A.T. Bell, Tailoring the cooperative acid-base effects in silica-supported amine catalysts: applications in the continuous gas-phase self-condensation of n-butanal, ChemCatChem 6 (5) (2014) 1283-1290. [52] S. Shylesh, D. Hanna, J. Gomes, C.G. Canlas, M. Head-Gordon, A.T. Bell, The role of hydroxyl group acidity on the activity of silica-supported secondary amines for the self-condensation of n-butanal, ChemSusChem 8 (3) (2015) 466-472. [53] M.C. Hou, F. Li, A.Z. Jia, Y.Y. Wang, Y.J. Wang, One-pot synthesis of biomass-derived porous carbon-based composites as an efficient acid-base bifunctional catalyst for self-condensation of n-butyraldehyde, React. Chem. Eng. 7 (6) (2022) 1358-1367. [54] X. He, L. Wu, H. An, X. Zhao, Y. Wang, Influence of preparation condition on the catalytic performance of KF/MgO-Al2O3 for n-butanal self-condensation, Spec. Petrochem. 34 (2017) 1-6. [55] G. Zheng, X. He, H. An, X. Zhao, Y. Wang, TiO2-catalyzed n-butyraldehyde self-condensation reaction mechanism, Chem. React. Eng. Technol. 35 (2019) 306-314. [56] H. Idriss, K.S. Kim, M.A. Barteau, Carbon-Carbon bond formation via aldolization of acetaldehyde on single crystal and polycrystalline TiO2 surfaces, J. Catal. 139 (1) (1993) 119-133. |
[1] | Zhengyang Liu, Xianlong Liu, Shuang Ma, Xiaolei Guo, Minhua Ai, Chengxiang Shi, Zhenfeng Huang, Xiangwen Zhang, Jijun Zou, Lun Pan. One-step synthesis of caged hydrocarbon fuel via photoinduced intramolecular cycloaddition of 5-vinyl-2-norbornene [J]. Chinese Journal of Chemical Engineering, 2025, 80(4): 61-69. |
[2] | Aleksey K. Sagidullin, Sergey S. Skiba, Tatyana P. Adamova, Andrey Y. Manakov. Investigation of the formation processes of CO2 hydrate films on the interface of liquid carbon dioxide with humic acids solutions [J]. Chinese Journal of Chemical Engineering, 2025, 79(3): 53-61. |
[3] | Pengxing Yuan, Meng Li, Shiyi Chen, Wenguo Xiang. Thermodynamic properties and reaction mechanism of coal reductive decomposition phosphogypsum to prepare CaO and SO2 [J]. Chinese Journal of Chemical Engineering, 2025, 79(3): 135-144. |
[4] | Zhe Ding, Li Guo, Fang Bai, Chao Hua, Ping Lu, Jinyi Chen. Toward the rational design for low-temperature hydrogenation of silicon tetrachloride: Mechanism and data-driven interpretable descriptor [J]. Chinese Journal of Chemical Engineering, 2025, 79(3): 172-184. |
[5] | Kai Ji, Zhencheng Ye, Feng Qian. Reaction network design and hybrid modeling of S Zorb [J]. Chinese Journal of Chemical Engineering, 2024, 73(9): 301-310. |
[6] | Maoqiao Xiang, Wenjun Ding, Qinghua Dong, Qingshan Zhu. Synthesis methods and powder quality of titanium monocarbide [J]. Chinese Journal of Chemical Engineering, 2024, 72(8): 10-18. |
[7] | Tianxiao Huang, Binhang Yan. Evaluation and application of kinetic models for Cu-catalyzed acetylene hydrochlorination [J]. Chinese Journal of Chemical Engineering, 2024, 72(8): 209-219. |
[8] | Hai Cao, Haibin Yang, Yanxiong Fang, Yuandi Zeng, Xiaolan Cai, Jingjing Ma. Study on trifluoromethanesulfonic acid-promoted synthesis of daidzein: Process optimization and reaction mechanism [J]. Chinese Journal of Chemical Engineering, 2024, 71(7): 132-139. |
[9] | Shida Gao, Cuimei Bo, Chao Jiang, Quanling Zhang, Genke Yang, Jian Chu. Hybrid modeling for carbon monoxide gas-phase catalytic coupling to synthesize dimethyl oxalate process [J]. Chinese Journal of Chemical Engineering, 2024, 70(6): 234-250. |
[10] | Shen Li, Yin-Ning Zhou, Zhong-Xin Liu, Zheng-Hong Luo. Effect of solvent on the initiation mechanism of living anionic polymerization of styrene: A computational study [J]. Chinese Journal of Chemical Engineering, 2024, 69(5): 135-142. |
[11] | Jiangtao Cai, Qingfu Huang, Huan Chen, Tao Zhang, Bo Niu, Yayun Zhang, Donghui Long. Evaluating two stages of silicone-containing arylene resin oxidation via experiment and molecular simulation [J]. Chinese Journal of Chemical Engineering, 2024, 66(2): 189-202. |
[12] | Yao Li, Yuchun Zhang, Zhiyu Li, Huiyan Zhang, Peng Fu. Reaction pathways and selectivity in the chemo-catalytic conversion of cellulose and its derivatives to ethylene glycol: A review [J]. Chinese Journal of Chemical Engineering, 2024, 66(2): 310-331. |
[13] | Shaopeng Li, Weichao Li, Yun Wu, Xianming Zheng, Xuehui Zhao, Ning Nan, Hongwei Zhang. Preparation of Mn-Ce oxide-loaded Al2O3 by citric acid-assisted impregnation for enhanced catalytic ozonation degradation of dye wastewater [J]. Chinese Journal of Chemical Engineering, 2024, 76(12): 237-250. |
[14] | Binxuan Zhou, Jingcai Chang, Jun Li, Jinglan Hong, Tao Wang, Liqiang Zhang, Ping Zhou, Chunyuan Ma. Study of the reaction mechanism for preparing powdered activated coke with SO2 adsorption capability via one-step rapid activation method under flue gas atmosphere [J]. Chinese Journal of Chemical Engineering, 2024, 65(1): 158-168. |
[15] | Xinyu Liu, Hongliang Sheng, Song He, Chunhua Du, Yuansheng Ma, Chichi Ruan, Chunxiang He, Huaming Dai, Yajun Huang, Yuelei Pan. Insight into pyrolysis of hydrophobic silica aerogels: Kinetics, reaction mechanism and effect on the aerogels [J]. Chinese Journal of Chemical Engineering, 2023, 58(6): 266-281. |
Viewed | ||||||||||||||||||||||||||||||||||||||||||||||||||
Full text 25
|
|
|||||||||||||||||||||||||||||||||||||||||||||||||
Abstract 21
|
|
|||||||||||||||||||||||||||||||||||||||||||||||||