Photoinduced transposed Paternò-Büchi reaction for effective synthesis of high-performance jet fuel

doi:10.1016/j.cjche.2023.09.014

中国化学工程学报 ›› 2024, Vol. 67 ›› Issue (3): 39-48.DOI: 10.1016/j.cjche.2023.09.014

Photoinduced transposed Paternò-Büchi reaction for effective synthesis of high-performance jet fuel

Jinxiu Hu^1,2,3, Xianlong Liu^1,2,3, Yi Liu¹, Kang Xue^1,2,3,4, Chengxiang Shi^1,2,3,4, Xiangwen Zhang^1,2,3,4, Li Wang^1,2,3,4, Ji-Jun Zou^1,2,3,4, Lun Pan^1,2,3,4,

1 Key Laboratory for Green Chemical Technology of the Ministry of Education, School of Chemical Engineering and Technology, Tianjin University, Tianjin 300072, China;
2 Haihe Laboratory of Sustainable Chemical Transformations, Tianjin 300192, China;
3 Zhejiang Institute of Tianjin University, Ningbo 315201, China;
4 Collaborative Innovative Center of Chemical Science and Engineering (Tianjin), Tianjin 300072, China

收稿日期:2023-05-21 修回日期:2023-08-16 出版日期:2024-03-28 发布日期:2024-06-01
通讯作者: Lun Pan,E-mail address:panlun76@tju.edu.cn.
基金资助:
The authors appreciate the support from National Key Research and Development Program of China (2021YFC2103704), the National Natural Science Foundation of China (22222808, 21978200), and the Haihe Laboratory of Sustainable Chemical Transformations.

Photoinduced transposed Paternò-Büchi reaction for effective synthesis of high-performance jet fuel

Jinxiu Hu^1,2,3, Xianlong Liu^1,2,3, Yi Liu¹, Kang Xue^1,2,3,4, Chengxiang Shi^1,2,3,4, Xiangwen Zhang^1,2,3,4, Li Wang^1,2,3,4, Ji-Jun Zou^1,2,3,4, Lun Pan^1,2,3,4,

1 Key Laboratory for Green Chemical Technology of the Ministry of Education, School of Chemical Engineering and Technology, Tianjin University, Tianjin 300072, China;
2 Haihe Laboratory of Sustainable Chemical Transformations, Tianjin 300192, China;
3 Zhejiang Institute of Tianjin University, Ningbo 315201, China;
4 Collaborative Innovative Center of Chemical Science and Engineering (Tianjin), Tianjin 300072, China

Received:2023-05-21 Revised:2023-08-16 Online:2024-03-28 Published:2024-06-01
Contact: Lun Pan,E-mail address:panlun76@tju.edu.cn.
Supported by:
The authors appreciate the support from National Key Research and Development Program of China (2021YFC2103704), the National Natural Science Foundation of China (22222808, 21978200), and the Haihe Laboratory of Sustainable Chemical Transformations.

摘要/Abstract

摘要： High-energy-density fuels are important for volume-limited aerospace vehicles, but the increase in fuel energy density always leads to poor cryogenic performance. Herein, we investigated the transposed Paternò-Büchi reaction of biomass cyclic ketone and cyclic alkene to synthesize a new kind of alkyl-substituted polycyclic hydrocarbon fuel with high energy density and good cryogenic performance. The triplet-energy-quenching results and phosphorescent emission spectra reveal the sensitization mechanism of the reaction, including photosensitizer excitation, triplettriplet energy transfer, cyclization, and relaxation, and the possible reaction path was revealed by the density functional theory (DFT) calculations. The reaction conditions of photosensitizer type and addition, molar ratio of substrates, reaction temperature, and incident light intensity were optimized, with the target product yield achieving 65.5%. Moreover, the reaction dynamics of the reaction rate versus the light intensity are established. After the hydrogenation-deoxygenation reaction, three fuels with a high density of≥0.864-0.938 g·ml^-1 and a low freezing point of < 55 ℃ are obtained. This work provides a benign and effective approach to synthesize high-performance fuels.

关键词: High-energy-density fuel, Transposed Paternò-Büchi reaction, Kinetics, Bioenergy, Photochemistry

Abstract: High-energy-density fuels are important for volume-limited aerospace vehicles, but the increase in fuel energy density always leads to poor cryogenic performance. Herein, we investigated the transposed Paternò-Büchi reaction of biomass cyclic ketone and cyclic alkene to synthesize a new kind of alkyl-substituted polycyclic hydrocarbon fuel with high energy density and good cryogenic performance. The triplet-energy-quenching results and phosphorescent emission spectra reveal the sensitization mechanism of the reaction, including photosensitizer excitation, triplettriplet energy transfer, cyclization, and relaxation, and the possible reaction path was revealed by the density functional theory (DFT) calculations. The reaction conditions of photosensitizer type and addition, molar ratio of substrates, reaction temperature, and incident light intensity were optimized, with the target product yield achieving 65.5%. Moreover, the reaction dynamics of the reaction rate versus the light intensity are established. After the hydrogenation-deoxygenation reaction, three fuels with a high density of≥0.864-0.938 g·ml^-1 and a low freezing point of < 55 ℃ are obtained. This work provides a benign and effective approach to synthesize high-performance fuels.

Key words: High-energy-density fuel, Transposed Paternò-Büchi reaction, Kinetics, Bioenergy, Photochemistry

Jinxiu Hu, Xianlong Liu, Yi Liu, Kang Xue, Chengxiang Shi, Xiangwen Zhang, Li Wang, Ji-Jun Zou, Lun Pan. Photoinduced transposed Paternò-Büchi reaction for effective synthesis of high-performance jet fuel[J]. 中国化学工程学报, 2024, 67(3): 39-48.

参考文献

[1] X.W. Zhang, L. Pan, L. Wang, J.J. Zou, Review on synthesis and properties of high-energy-density liquid fuels:Hydrocarbons, nanofluids and energetic ionic liquids, Chem. Eng. Sci. 180(2018)95-125.
[2] G.K. Nie, X.W. Zhang, P.J. Han, J.J. Xie, L. Pan, L. Wang, J.J. Zou, Lignin-derived multi-cyclic high density biofuel by alkylation and hydrogenated intramolecular cyclization, Chem. Eng. Sci. 158(2017)64-69.
[3] J.J. Xie, X.W. Zhang, Y.K. Liu, Z. Li, E. Xiu-tian-feng, J.W. Xie, Y.C. Zhang, L. Pan, J. J. Zou, Synthesis of high-density liquid fuel via Diels-Alder reaction of dicyclopentadiene and lignocellulose-derived 2-methylfuran, Catal. Today 319(2019)139-144.
[4] L. Wang, X.W. Zhang, J.J. Zou, H. Han, Y.H. Li, L. Wang, Acid-catalyzed isomerization of tetrahydrotricyclopentadiene:Synthesis of high-energy-density liquid fuel, Energy Fuels 23(5)(2009)2383-2388.
[5] Q. Deng, G.K. Nie, L. Pan, J.J. Zou, X.W. Zhang, L. Wang, Highly selective selfcondensation of cyclic ketones using MOF-encapsulating phosphotungstic acid for renewable high-density fuel, Green Chem. 17(8)(2015)4473-4481.
[6] B.G. Harvey, R.L. Quintana, Synthesis of renewable jet and diesel fuels from 2-ethyl-1-hexene, Energy Environ. Sci. 3(3)(2010)352-357.
[7] Q. Deng, P.J. Han, J.S. Xu, J.J. Zou, L. Wang, X.W. Zhang, Highly controllable and selective hydroxyalkylation/alkylation of 2-methylfuran with cyclohexanone for synthesis of high-density biofuel, Chem. Eng. Sci. 138(2015)239-243.
[8] S.S. Li, F. Chen, N. Li, W.T. Wang, X.R. Sheng, A.Q. Wang, Y. Cong, X.D. Wang, T. Zhang, Synthesis of renewable triketones, diketones, and jet-fuel range cycloalkanes with 5-hydroxymethylfurfural and ketones, ChemSusChem 10(4)(2017)711-719.
[9] S.S. Li, N. Li, W.T. Wang, L. Li, A.Q. Wang, X.D. Wang, T. Zhang, Synthesis of jet fuel range branched cycloalkanes with mesityl oxide and 2-methylfuran from lignocellulose, Sci. Rep. 6(2016)32379.
[10] Z.P. Huang, Z.T. Zhao, C.F. Zhang, J.M. Lu, H.F. Liu, N.C. Luo, J. Zhang, F. Wang, Enhanced photocatalytic alkane production from fatty acid decarboxylation via inhibition of radical oligomerization, Nat. Catal. 3(2)(2020)170-178.
[11] N.C. Yang, M. Nussim, M.J. Jorgenson, S. Murov, Photochemical reactions of carbonyl compounds in solution the Paternò-Büchi reaction, Tetrahedron Lett. 5(48)(1964)3657-3664.
[12] M. Freneau, N. Hoffmann, The Patern o-Büchi reaction dMechanisms and application to organic synthesis, J. Photochem. Photobiol., C 33(2017)83-108.
[13] G. Büchi, C.G. Inman, E.S. Lipinsky, Light-catalyzed organic reactions. I. the reaction of carbonyl compounds with 2-methyl-2-butene in the presence of ultraviolet light, J. Am. Chem. Soc. 76(17)(1954)4327-4331.
[14] F.H. Isikgor, C.R. Becer, Lignocellulosic biomass:a sustainable platform for the production of bio-based chemicals and polymers, Polym. Chem. 6(25)(2015)4497-4559.
[15] D.M. Alonso, J.Q. Bond, J.A. Dumesic, Catalytic conversion of biomass to biofuels, Green Chem. 12(9)(2010)1493.
[16] H.B. Schlegel, Optimization of equilibrium geometries and transition structures, J. Comput. Chem. 3(2)(1982)214-218.
[17] S. Wilsey, L. Gonz alez, M.A. Robb, K.N. Houk, Ground-and excited-state surfaces for the[2+2] -photocycloaddition of a, b-enones to alkenes, J. Am. Chem. Soc. 122(24)(2000)5866-5876.
[18] Y. Liu, Y. Chen, S. Ma, X.L. Liu, X.W. Zhang, J.J. Zou, L. Pan, Synthesis of advanced fuel with density higher than 1 g/mL by photoinduced[2+2] cycloaddition of norbornene, Fuel 318(2022)123629.
[19] R. Remy, C.G. Bochet, Areneealkene cycloaddition, Chem. Rev. 116(17)(2016)9816-9849.
[20] R.S.H. Liu, N.J. Turro Jr., G.S. Hammond, Mechanisms of photochemical reactions in solution. XXXI. activation and deactivation of conjugated dienes by energy transfer, J. Am. Chem. Soc. 87(15)(1965)3406-3412.
[21] K. Nakatani, H. Sato, R. Fukuda, A catalyzed E/Z isomerization mechanism of stilbene using para-benzoquinone as a triplet sensitizer, Phys. Chem. Chem. Phys. 24(3)(2022)1712-1721.
[22] P.J. Wagner, Conformational changes involved in the singlet-triplet transitions of biphenyl, J. Am. Chem. Soc. 89(12)(1967)2820-2825.
[23] J. Bull, O. Davis, Recent advances in the synthesis of 2-substituted oxetanes, Synlett 26(10)(2015)1283-1288.
[24] M. Zhu, X.A. Zhang, C. Zheng, S.L. You, Visible-light-induced dearomatization via[2+2] cycloaddition or 1, 5-hydrogen atom transfer:Divergent reaction pathways of transient diradicals, ACS Catal. 10(21)(2020)12618-12626.
[25] N. El Achi, F. Gelat, N.P. Cheval, A. Mazzah, Y. Bakkour, M. Penhoat, L. ChaussetBoissarie, C. Rolando, Sensitized[2+2] intramolecular photocycloaddition of unsaturated enones using UV LEDs in a continuous flow reactor:Kinetic and preparative aspects, React. Chem. Eng. 4(5)(2019)828-837.
[26] A. Cuppoletti, J.P. Dinnocenzo, J.L. Goodman, I.R. Gould, Bond-coupled electron transfer reactions:Photoisomerization of norbornadiene to quadricyclane, J. Phys. Chem. A 103(51)(1999)11253-11256.
[27] C. Shen, M.J. Shang, H. Zhang, Y.H. Su, A UV-LEDs based photomicroreactor for mechanistic insights and kinetic studies in the norbornadiene photoisomerization, AlChE. J. 66(2)(2020) e16841.
[28] W. Nau, Modern molecular photochemistry of organic molecules, in:N.J. turro, V. ramamurthy, J.C. scaiano (Eds.), ChemPhysChem (12)(13)(2011)2496-2497.
[29] C. Prentice, A.E. Martin, J. Morrison, A.D. Smith, E. Zysman-Colman, Benzophenone as a cheap and effective photosensitizer for the photocatalytic synthesis of dimethyl cubane-1, 4-dicarboxylate, Org. Biomol. Chem. 21(16)(2023)3307-3310.
[30] F. Bayrakçeken, Triplet-triplet optical energy transfer from benzophenone to naphthalene in the vapor phase, Spectrochim. Acta 71(2)(2008)603-608.
[31] M. Arslan, O. Ceylan, R. Arslan, M.A. Tasdelen, Facile UV-induced covalent modification and crosslinking of styrene-isoprene-styrene copolymer via paterno-Büchi[2+2] photocycloaddition, RSC Adv. 11(15)(2021)8585-8593.
[32] N.K. Singha, B. de Ruiter, U.S. Schubert, Atom transfer radical polymerization of 3-ethyl-3-(acryloyloxy) methyloxetane, Macromolecules 38(9)(2005)3596-3600.
[33] E. Blomsma, J.A. Martens, P.A. Jacobs, Mechanisms of heptane isomerization on bifunctional Pd/H-beta zeolites, J. Catal. 159(2)(1996)323-331.
[34] J.F. Yang, N. Li, G.Y. Li, W.T. Wang, A.Q. Wang, X.D. Wang, Y. Cong, T. Zhang, Synthesis of renewable high-density fuels using cyclopentanone derived from lignocellulose, Chem. Commun. 50(20)(2014)2572-2574.
[35] Z.Y. Wu, Y.B. Mao, M. Raza, J.Z. Zhu, Y. Feng, S.X. Wang, Y. Qian, L. Yu, X.C. Lu, Surrogate fuels for RP-3 kerosene formulated by emulating molecular structures, functional groups, physical and chemical properties, Combust, Flame 208(2019)388-401.
[36] G.Y. Li, B.L. Hou, A.Q. Wang, X.L. Xin, Y. Cong, X.D. Wang, N. Li, T. Zhang, Making JP-10 superfuel affordable with a lignocellulosic platform compound, Angew. Chem. Int. Ed. 58(35)(2019)12154-12158.

Photoinduced transposed Paternò-Büchi reaction for effective synthesis of high-performance jet fuel

Photoinduced transposed Paternò-Büchi reaction for effective synthesis of high-performance jet fuel

PDF (PC)

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 15

编辑推荐

Metrics

本文评价

[1]	Shanghong Ma, Jianbo Qu, Haitao Zhang, Xiubin Cui, Peng Ye, Qingfei Hu, Mingzhen Chao. Synthesis of waterborne polyurethane-humic acid cross-linked biomass porous materials for the adsorption of methylene blue[J]. 中国化学工程学报, 2024, 67(3): 27-38.
[2]	Deqing He, Zihao Xie, Qian Yang, Wei Wang, Chao Su. Tungsten oxide/nitrogen-doped carbon nanotubes composite catalysts for enhanced redox kinetics in lithium-sulfur batteries[J]. 中国化学工程学报, 2024, 67(3): 58-67.
[3]	Siang Chen, Wenling Wu, Zhaoyang Niu, Deqi Kong, Wenbin Li, Zhongli Tang, Donghui Zhang. High adsorption selectivity of activated carbon and carbon molecular sieve boosting CO₂/N₂ and CH₄/N₂ separation[J]. 中国化学工程学报, 2024, 67(3): 282-297.
[4]	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]. 中国化学工程学报, 2024, 66(2): 189-202.
[5]	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]. 中国化学工程学报, 2024, 66(2): 310-331.
[6]	Chao Li, Shizhao Wang, Yunshan Wang, Xuebin An, Gang Yang, Yong Sun. Study on synergistic leaching of potassium and phosphorus from potassium feldspar and solid waste phosphogypsum via coupling reactions[J]. 中国化学工程学报, 2024, 65(1): 117-129.
[7]	Haoyu Yao, Jiangcheng Li, Jiangyan Li, Xiangfeng Liang, Gang Wang, Haiyan Luo. Studies on polyoxymethylene dimethyl ethers production from dimethoxymethane and 1,3,5-trioxane over SO₄^2-/ZrO₂-TiO₂[J]. 中国化学工程学报, 2023, 61(9): 24-36.
[8]	Dongdong Hu, Yinglei Wang, Chuan Xiao, Yifei Hu, Zhiyong Zhou, Zhongqi Ren. Studies on ammonium dinitramide and 3,4-diaminofurazan cocrystal for tuning the hygroscopicity[J]. 中国化学工程学报, 2023, 61(9): 157-164.
[9]	Xiaolin Guo, Zhaoyang Zhang, Pengfei Xing, Shuai Wang, Yibing Guo, Yanxin Zhuang. Kinetic mechanism of copper extraction from methylchlorosilane slurry residue using hydrogen peroxide as oxidant[J]. 中国化学工程学报, 2023, 60(8): 228-234.
[10]	Xun Tao, Fan Zhou, Xinlei Yu, Songling Guo, Yunfei Gao, Lu Ding, Guangsuo Yu, Zhenghua Dai, Fuchen Wang. Effect of carbon dioxide on oxy-fuel combustion of hydrogen sulfide: An experimental and kinetic modeling[J]. 中国化学工程学报, 2023, 59(7): 105-117.
[11]	Junyang Liu, Luming Wang, Yuhang Bian, Chunshan Li, Zengxi Li, Jie Li. Liquid-phase esterification of methacrylic acid with methanol catalyzed by cation-exchange resin in a fixed bed reactor: Experimental and kinetic studies[J]. 中国化学工程学报, 2023, 58(6): 1-10.
[12]	Wei Wang, Romain Lemaire, Ammar Bensakhria, Denis Luart. Thermogravimetric analysis and kinetic modeling of the co-pyrolysis of a bituminous coal and poplar wood[J]. 中国化学工程学报, 2023, 58(6): 53-68.
[13]	Masoumeh Sheikh Hosseini Lori, Mohammad Delnavaz, Hoda Khoshvaght. Synthesizing and characterizing the magnetic EDTA/chitosan/CeZnO nanocomposite for simultaneous treating of chromium and phenol in an aqueous solution[J]. 中国化学工程学报, 2023, 58(6): 76-88.
[14]	Bing Liu, Yingjiao Li, Moses Arowo, Guangwen Chu, Yong Luo, Liangliang Zhang, Haikui Zou, Baochang Sun. Sulfonation of 1, 4-diaminoanthraquinone leuco by chlorosulfonic acid: Kinetics and process intensification[J]. 中国化学工程学报, 2023, 58(6): 163-169.
[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]. 中国化学工程学报, 2023, 58(6): 266-281.