4-乙基苯酚和苯甲醇烷基化反应制备高密度航油前驱体

陈美梅, 陈淑钿, 简雅婷, 谢君, 余强

太阳能学报 ›› 2026, Vol. 47 ›› Issue (3) : 481-487.

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太阳能学报 ›› 2026, Vol. 47 ›› Issue (3) : 481-487. DOI: 10.19912/j.0254-0096.tynxb.2024-1970

4-乙基苯酚和苯甲醇烷基化反应制备高密度航油前驱体

  • 陈美梅1, 陈淑钿1, 简雅婷2, 谢君1, 余强1
作者信息 +

SYNTHESIS OF HIGH DENSITY JET FUEL PRECURSORS VIA ALKYLATION REACTION OF 4-ETHYLPHENOL AND BENZYL ALCOHOL

  • Chen Meimei1, Chen Shutian1, Jian Yating2, Xie Jun1, Yu Qiang1
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摘要

以木质素主要解聚产物4-乙基苯酚和苯甲醇为反应底物,乙酸-氯化胆碱低共熔溶剂与Amberlyst-15离子交换树脂耦合构建烷基化催化体系制备高密度航油前驱体,考察反应温度、反应时间、低共熔溶剂物质的量之比、催化剂添加量及底物物质的量之比对其烷基化效果的影响。结果表明:在苯甲醇与4-乙基苯酚物质的量之比为1∶1、氯化胆碱/乙酸物质的量之比1∶6及5%(以质量分数计) Amberlyst-15添加量下,在170 ℃反应4 h,可实现较高的苯甲醇转化率(94.89%)和4-乙基苯酚转化率(80.78%)。同时,产物4-α-肉桂苯酚(C15-1)和邻异丙苯基苯酚(C15-2)的总选择性及收率分别达到74.58%和60.24%。

Abstract

4-ethylphenol and benzyl alcohol, the main depolymerization products of lignin, were used as reaction substrates to prepare high-density jet fuel precursor in an alkylation catalytic system coupled by acetic acid-choline chloride (Aa-ChCl) deep eutectic solvent and Amberlyst-15 ion exchange resin. The effects of reaction temperature, reaction time, molar ratio of the deep eutectic solvent components, catalyst amount and substrate molar ratio on alkylation were investigated. The results showed that a high conversion rates of benzyl alcohol (94.89%) and 4-ethylphenol (80.78%) were achieved at 170 ℃ over 4 hours with a molar ratio of benzyl alcohol to 4-ethylphenol of 1∶1 in an optimized system (Aa-ChCl at a molar ratio of 1:6 and an addition of 5% Amberlyst-15). Meanwhile, the total selectivity and yield of 4-α-cinnamophenol (C15-1) and o-isopropylphenol (C15-2) could reach 74.58% and 60.24%, respectively.

关键词

生物质 / 木质素 / 烷基化 / 低共熔溶剂 / 苯甲醇 / 航油前驱体

Key words

biomass / lignin / alkylation / deep eutectic solvent / benzyl alcohol / jet fuel precursors

引用本文

导出引用
陈美梅, 陈淑钿, 简雅婷, 谢君, 余强. 4-乙基苯酚和苯甲醇烷基化反应制备高密度航油前驱体[J]. 太阳能学报. 2026, 47(3): 481-487 https://doi.org/10.19912/j.0254-0096.tynxb.2024-1970
Chen Meimei, Chen Shutian, Jian Yating, Xie Jun, Yu Qiang. SYNTHESIS OF HIGH DENSITY JET FUEL PRECURSORS VIA ALKYLATION REACTION OF 4-ETHYLPHENOL AND BENZYL ALCOHOL[J]. Acta Energiae Solaris Sinica. 2026, 47(3): 481-487 https://doi.org/10.19912/j.0254-0096.tynxb.2024-1970
中图分类号: TK6   

参考文献

[1] SHEN Z S, ZHANG G W, SHI C X, et al.Bifunctional Pt/Hβ catalyzed alkylation and hydrodeoxygenation of phenol and cyclohexanol in one-pot to synthesize high-density fuels[J]. Fuel, 2023, 334: 126634.
[2] YANG S C, SHI C X, SHEN Z S, et al.Conversion of lignin oil and hemicellulose derivative into high-density jet fuel[J]. Journal of energy chemistry, 2023, 77: 452-460.
[3] WANG C G, ZHANG X H, LIU Q, et al.A review of conversion of lignocellulose biomass to liquid transport fuels by integrated refining strategies[J]. Fuel processing technology, 2020, 208: 106485.
[4] 简雅婷, 王帆, 陈小燕, 等. 药渣木质素定向解聚制备高密度航油合成原料[J]. 太阳能学报, 2024, 45(3): 163-168.
JIAN Y T, WANG F, CHEN X Y, et al.Preparation of high-density jet fuel synthetic raw materials by directional depolymerization of lignin from residue[J]. Acta energiae solaris sinica, 2024, 45(3): 163-168.
[5] WANG H L, YANG B, ZHANG Q, et al.Catalytic routes for the conversion of lignocellulosic biomass to aviation fuel range hydrocarbons[J]. Renewable and sustainable energy reviews, 2020, 120: 109612.
[6] LIU Y N, SHI C X, SHEN Z S, et al.Continuous liquid-phase alkylation of lignocellulose-derived phenolics and cyclopentanol under large space velocity for efficient synthesis of high-performance biofuel[J]. Chemical engineering science, 2024, 285: 119635.
[7] ARIAS K S, CLIMENT M J, CORMA A, et al.Synthesis of high quality alkyl naphthenic kerosene by reacting an oil refinery with a biomass refinery stream[J]. Energy & environmental science, 2015, 8(1): 317-331.
[8] NIE G K, ZHANG X W, HAN P J, et al.Lignin-derived multi-cyclic high density biofuel by alkylation and hydrogenated intramolecular cyclization[J]. Chemical engineering science, 2017, 158: 64-69.
[9] LIU Y S, CHENG G H, BARÁTH E, et al. Alkylation of lignin-derived aromatic oxygenates with cyclic alcohols on acidic zeolites[J]. Applied catalysis B: environmental, 2021, 281: 119424.
[10] BAI J, ZHANG Y, ZHANG X H, et al.Synthesis of high-density components of jet fuel from lignin-derived aromatics via alkylation and subsequent hydrodeoxygenation[J]. ACS sustainable chemistry & engineering, 2021, 9(20): 7112-7119.
[11] SHU R Y, LI R X, LIN B Q, et al.A review on the catalytic hydrodeoxygenation of lignin-derived phenolic compounds and the conversion of raw lignin to hydrocarbon liquid fuels[J]. Biomass and bioenergy, 2020, 132: 105432.
[12] 陈小燕, 王帆, 王艳玲, 等. 低共熔溶剂对甘草渣的预处理研究[J]. 太阳能学报, 2022, 43(12): 446-452.
CHEN X Y, WANG F, WANG Y L, et al.Study on pretreatment of licorice residue in deep eutectic solvents[J]. Acta energiae solaris sinica, 2022, 43(12): 446-452.
[13] JIAN Y T, LI X L, LIU Y W, et al.Deep eutectic solvent assists H-β in aldol condensation of acetovanillone and p-hydroxybenzaldehyde to prepare a high density aviation oil precursor[J]. Fuel, 2023, 347: 128491.
[14] 王严严, 刘云云, 董继先, 等. 低共熔溶剂体系中糠醛与环戊酮合成生物燃料中间体的研究[J]. 太阳能学报, 2021, 42(8): 478-482.
WANG Y Y, LIU Y Y, DONG J X, et al.Study on compositing biofuel intermediates from furfural and cyclopentanone in low eutectic solvent[J]. Acta energiae solaris sinica, 2021, 42(8): 478-482.
[15] 宋振龙, 王帆, 陈小燕, 等. 氯化胆碱/对香豆酸低共熔溶剂预处理中药渣提高木质素脱出率的研究[J]. 太阳能学报, 2022, 43(1): 191-195.
SONG Z L, WANG F, CHEN X Y, et al.Study on improving lignin removal rate by pretreatment of Chinese medicine residue with choline chloride/p-coumaric acid deep eutectic solvents[J]. Acta energiae solaris sinica, 2022, 43(1): 191-195.
[16] MA Z H, SHA J L, ZHENG W Z, et al.Effects of deep eutectic solvents on H2SO4-catalyzed alkylation: combining experiment and molecular dynamics simulation[J]. AIChE journal, 2022, 68(4): e17556.
[17] YU F L, GU Y L, GAO X, et al.Alkylation of isobutane and isobutene catalyzed by trifluoromethanesulfonic acid-taurine deep eutectic solvents in polyethylene glycol[J]. Chemical communications, 2019, 55(33): 4833-4836.
[18] TANG X D, ZHANG Y F, LI J J.Alkylation of thiophenic compounds catalyzed by deep eutectic solvents[J]. Catalysis communications, 2015, 70: 40-43.
[19] XIONG J P, ZHANG D J, YANG G Q, et al.Alkylation of phenol and tert-butyl alcohol catalyzed by deep eutectic solvents under mild conditions[J]. Industrial & engineering chemistry research, 2021, 60(36): 13204-13213.
[20] LI H, DENG Q, CHEN H, et al.Benzenesulfonic acid functionalized hydrophobic mesoporous biochar as an efficient catalyst for the production of biofuel[J]. Applied catalysis A: general, 2019, 580: 178-185.
[21] LI Z, PAN L, NIE G K, et al.Synthesis of high-performance jet fuel blends from biomass-derived 4-ethylphenol and phenylmethanol[J]. Chemical engineering science, 2018, 191: 343-349.
[22] CHEN S T, JIAN Y T, LIU Y W, et al.Deep eutectic solvents promote in situ hydrogenolysis of Evodia lepta residue in preparing small aromatic phenol ketones[J]. Fuel, 2024, 366: 131348.
[23] ZHANG J, WANG X Y, YANG B, et al.Superhydrophobic and superacid magnetic catalyst induced highly selective aldol condensation and alkylation for high-density biofuels[J]. Fuel, 2024, 378: 132930.
[24] LIU D N, NIU X P, GUO Z, et al.One-pot solvent-free sequential synthesis of high-density polycycloalkanes fuels from lignin-derivatives over laminated NbOPO4 catalyst[J]. Fuel, 2024, 360: 130570.

基金

国家自然科学基金(52276192); 广东省基础与应用基础研究基金(2023B1515020094)

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