铜(I)催化生物质基平台化合物糠醛与直链醇的氧化-缩合反应
收稿日期: 2021-07-18
修回日期: 2021-09-15
网络出版日期: 2021-11-03
基金资助
国家自然科学基金(21878235); 天津市研究生科研创新(2019YJSS058)
Copper(I)-Catalyzed Aerobic Oxidative Condensation of Biomass-Based Platform Compound Furfurals with Straight-Chain Alcohols
Received date: 2021-07-18
Revised date: 2021-09-15
Online published: 2021-11-03
Supported by
National Natural Science Foundation of China(21878235); Research Innovation Program of Graduate Students in Tianjin(2019YJSS058)
师静 , 郭鹏飞 , 李蔚 , 孙海静 , 孟令武 , 仝新利 . 铜(I)催化生物质基平台化合物糠醛与直链醇的氧化-缩合反应[J]. 有机化学, 2022 , 42(3) : 905 -909 . DOI: 10.6023/cjoc202107039
In the face of the continuous consumption of fossil energy and the increasingly serious ecological damage, the synthesis of liquid fuels and high value-added fine chemicals from biomass-derived furfural has become one of the research hotspots in the field of energy and chemical industry. In this work, a highly efficient and selective aerobic oxidative condensation of furfural with straight-chain alcohol is achieved with simple copper(I) chloride as the catalyst. Therein, 3-(2- furanyl)-2-methyl-2-acrolein was synthesized by the oxidative condensation reaction of furfural with n-propanol under the mild conditions. As a result, it is found that the conversion of furfural and the selectivity of main product reached 94% and more than 99.9% in the presence of molecular oxygen, respectively. Moreover, the effects of basic additive, reaction time and temperature were further investigated in detail. In addition, oxidative condensation of different substrates was also successfully performed. This catalytic method provides a promising, green and sustainable technology for the valorization of biomass and biomass-based platform compounds.
Key words: furfural; oxidative condensation; halogenated copper salt; oxygen
[1] | Szuromi, P.; Jasny, B.; Clery, D.; Austin, J.; Hanson, B. Science 2007, 315, 781. |
[2] | Centi, G.; Van Santen, R. A. Catalysis for Renewables: From Feedstock to Energy Production, Wiley-VCH, Chichester, UK, 2007. |
[3] | Herbert, O. H. Modern Synthetic Reactions, Peking University Press, 1985. (in Chinese) |
[3] | ( Herbert, O. H. 现代合成反应, 北京大学出版社, 1985.) |
[4] | Peleteiro, S.; Rivas, S.; Alonso, J. L.; Santos, V.; Parajó, J. C. Bioresour. Technol. 2016, 202, 181. |
[5] | Dutta, S.; De, S.; Saha, B. Catal. Sci. Technol. 2012, 2, 2025. |
[6] | Mariscal, R.; Maireles-Torres, P.; Ojeda, M.; Sádaba, I.; Granados, M. Energy Environ. Sci. 2016, 9, 1144. |
[7] | Guo, H.; Yin, G. J. Phys. Chem. C 2011, 115, 17516. |
[8] | Li, J. Chem. Eng. J. 2001, 81, 338. |
[9] | Sádaba, I.; Ojeda, M.; Mariscal, R. J; Fierro, L.; Granados, M. Appl. Catal., B 2011, 101, 638. |
[10] | Kikhtyanin, O.; Bulanek, R.; Frolich, K. J. Mol. Catal. A: Chem. 2016, 424, 358. |
[11] | Desai, D. S.; Yadav, G. D. Ind. Eng. Chem. Res. 2019, 58, 16096. |
[12] | Ning, L.; Liao, S.; Cui, H.; Tong, X. Petrochem. Technol. 2017, 46, 130. (in Chinese) |
[12] | (宁良民, 廖圣云, 崔红格, 仝新利, 石油化工, 2017, 46, 130.) |
[13] | Tong, X.; Liu, Z.; Yu, L.; Li, Y. Chem. Commun. 2015, 51, 3674. |
[14] | Huo, N.; Ma, H.; Wang, X.; Wang, T.; Wang, G.; Wang, T.; Hou, L.; Gao, J.; Xu, J. Chin. J. Catal. 2017, 38, 1148. (in Chinese) |
[14] | (霍娜, 马红, 王新红, 王天龙, 王刚, 王婷, 候磊磊, 高进, 徐杰, 催化学报, 2017, 38, 1148.) |
[15] | Ning, L.; Liao, S.; Liu, X.; Yu, L.; Zhuang, X.; Tong, X. J. Catal. 2017, 352, 480. |
[16] | Thanh, D. N.; Kikhtyanin, O.; Ramos, R.; Kothari, M.; Ulbrich, P.; Munshi, T.; Kubička, D. Catal. Today 2016, 277, 97. |
[17] | Liu, Z.; Tong, X.; Liu, J.; Xue, S. Catal. Sci. Technol. 2016, 6, 1214. |
[18] | Ning, L.; Liao, S.; Cui, H.; Yu, L.; Tong, X. ACS Sustainable Chem. Eng. 2018, 6, 135. |
[19] | Tong, X.; Liu, Z.; Liao, S. Appl. Catal., A 2016, 510, 196. |
[20] | Yu, L.; Liao, S.; Ning, L.; Xue, S.; Liu, Z.; Tong, X. ACS Sustainable Chem. Eng. 2016, 4, 1894. |
[21] | Tong, X.; Zhang, Z.; Gao, Y.; Zhang, Y.; Yu, L.; Li, Y. Mol. Catal. 2019, 477, 110545. |
[22] | Ning, L.; Liao, S.; Liu, X.; Guo, P.; Zhang, Z.; Zhang, H.; Tong, X. J. Catal. 2018, 364, 1. |
[23] | Gao, Y.; Tong, X.; Zhang, H. Catal. Today 2020, 355, 238. |
[24] | Huang, H.; Yu, C.; Li, X.; Zhang, Y.; Zhang, Y.; Chen, X.; Mariano, P. S.; Xie, H.; Wang, W. Angew. Chem., Int. Ed. 2017, 56, 8201. |
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