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化学进展 2024, Vol. 36 Issue (3): 448-462 DOI: 10.7536/PC230713 前一篇   

• 综述 •

生物质多环碳氢高密度航空燃料合成

孔冲亚1, 谭芳芳4,*(), 王一卓5, 王洪5,6, 李占超1,2,3,*()   

  1. 1 四川轻化工大学化学与环境工程学院 自贡 643000
    2 绿色催化四川省高校重点实验室 自贡 643000
    3 精细化工助剂及表面活性剂四川省高校重点实验室 自贡 643000
    4 渭南师范学院化学与材料学院 渭南 714099
    5 西安交通大学前沿科学技术研究院 西安 710054
    6 西安交通大学动力工程多相流国家重点实验室 西安 710054
  • 收稿日期:2023-07-17 修回日期:2023-09-18 出版日期:2024-03-24 发布日期:2024-02-26
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Synthesis of Multi-Cyclic Hydrocarbon High-Density Aviation Fuels from Biomass

Chongya Kong1, Fangfang Tan4(), Yizhuo Wang5, Hong Wang5,6, Zhanchao Li1,2,3()   

  1. 1 School of Chemistry and Environmental Engineering, Sichuan University of Science & Engineering, Zigong 643000, China
    2 Key Laboratory of Green Chemistry of Sichuan Institutes of Higher Education, Zigong 643000, China
    3 Key Laboratories of Fine Chemicals and Surfactants in Sichuan Provincial Universities, Zigong 643000, China
    4 College of Chemistry and Materials Science, Weinan Normal University, Weinan 714099, China
    5 Frontier Institute of Science and Technology, Xi’an Jiaotong University, Xi’an 710054, China
    6 State Key Laboratory of Multiphase Flow in Power Engineering, Xi’an Jiaotong University, Xi’an 710054, China
  • Received:2023-07-17 Revised:2023-09-18 Online:2024-03-24 Published:2024-02-26
  • Contact: * e-mail: pp19881208@126.com (Zhanchao Li);tanfangfang@yau.edu.cn(Fangfang Tan)

高密度航空燃料是一类为提高航空航天飞行器的飞行性能而人工合成的液体碳氢化合物。与常规燃料相比，它具有高密度和高体积燃烧热值等优点，能有效提高飞行器的航程、航速、载荷等飞行性能。随着全球化石资源的日益减少和生态环境的持续恶化，以生物质为原料合成高密度航空燃料成为研究热点。本文综述了近年来由生物质平台分子及其衍生物合成多环碳氢高密度航空燃料的研究进展，主要介绍了高密度燃料合成中常见的构筑多环结构的C-C键偶联方法，包括羟醛缩合反应、烷基化反应、羟醛缩合-氢化脱氧-分子内烷基化反应、Diels-Alder反应、光照2+2环加成反应、重排反应；讨论了催化剂对C-C键偶联反应的影响因素；总结了大量的多环碳氢高密度航空燃料的性能，讨论了分子结构和组成对燃料性能的影响，取代基的适当引入、多组分燃料的形成是提高燃料综合性能的主要方法，以平台分子合成石油基型高密度燃料也是提高生物质高密度航空燃料综合性能的一种策略；最后，展望了生物质多环碳氢高密度航空燃料合成的新趋势。

关键词： 高密度航空燃料, 多环结构, 平台分子, C-C键偶联, 性能

High-density aviation fuels are a type of hydrocarbon which are synthesized to improve the flight performance of aerospace vehicles. They have the advantages of high density, high volumetric net heat of combustion value, and can effectively improve the flight performance of vehicles such as range, speed, load, etc. With the decrease of global fossil resources and the continuous deterioration of the ecological environment, the synthesis of high-density aviation fuels from biomass has become a research hotspot. In this review, the research progress in synthesis of multi-cyclic hydrocarbon high-density aviation fuels from platform molecules and derivatives in recent years is discussed. The common C-C bond coupling methods for constructing the multi-cyclic structure are introduced, including aldol condensation reaction, alkylation reaction, aldol-hydrodeoxygenation-alkylation reaction, Diels-Alder reaction, photoinduced 2+2 cycloaddition, rearrangement reaction. The new progress in synthesis of petroleum based high-density aviation fuels or multi-cyclic hydrocarbon mixed fuels from platform molecules is listed. The properties of a large number of multi-cyclic hydrocarbon high-density aviation fuels are summarized, and the influence of molecular structure and composition on fuel properties are discussed. Introduction of the appropriate substituent groups and synthesis of multi-component fuels are the main methods to improve the comprehensive properties of fuels. Synthesis of petroleum-based high-density fuels using platform molecules is another strategy to improve the properties of fuels. Finally, the development trend of synthesis of multi-cyclic hydrocarbon high-density aviation fuels using platform molecules from biomass is prospected.

Contents

1 Introduction

2 Aldol condensation reaction

3 Alkylation and Aldol-Hydrodeoxygenation- Alkylation reaction

4 Diels-Alder reaction

5 Photoinduced 2+2 cycloaddition reaction

6 Rearrangement reaction

7 Summary of fuel properties

8 Conclusion and outlook

Key words: high-density aviation fuel, multi-cyclic structure, platform molecules, C-C bond coupling, property
()
图1 生物质平台分子及其衍生物
Fig.1 The platform molecules and derivatives from biomass
图2 由环戊酮合成多环戊烷[23?~25]
Fig. 2 Synthesis of multi-cyclopentane from cyclopentanone[23?~25]
图3 由环戊酮和环己酮合成多组分的环烷烃[26]
Fig. 3 Synthesis of multi-component cycloalkane from cyclopentanone and cyclohexanone[26]
图4 由环戊酮和香兰素合成多环烷烃[27]
Fig. 4 Synthesis of multi-cycloalkane from cyclopentanone and vanillin[27]
图5 由环戊酮和香兰素合成多环烷烃混合物[28]
Fig. 5 Synthesis of multi-cyclopentane mixture from cyclopentanone and vanillin[28]
图6 由2, 5-己二酮合成甲基双环戊烷及三环戊烷[29]
Fig. 6 Synthesis of methyl substituted dicyclopentane and tricyclopentane from 2, 5-hexanedione[29]
图7 由异佛尔酮合成多甲基取代双环己烷[31]
Fig.7 Synthesis of multi-methyl substituted bicyclohexane from isophorone[31]
图8 Nafion催化β-pinene二聚制备高密度燃料[32]
Fig. 8 Synthesis of high-density fuel from β-pinene dimerization catalyzed by Nafion[32]
图9 由苯甲醇和4-乙基苯酚合成乙基取代双环己基甲烷[34]
Fig. 9 Synthesis of ethyl substituted dicyclohexylmethane from benzylalcohol and 4-ethylphenol[34]
图10 由苯酚和环戊醇合成多组分的多环烷烃[36]
Fig. 10 Synthesis of multi-cycloalkane mixture from phenol and cyclopentanol[36]
图11 由木质素油和环戊醇合成多组分的多环烷烃[37]
Fig. 11 Synthesis of multi-cycloalkane mixture from ligin oil and cyclopentanol[37]
图12 由2-苄基苯酚合成全氢芴[38]
Fig. 12 Synthesis of perfluorofluorene from 2- benzylphenol[38]
图13 由甲基苯甲醛和环己酮合成甲基全氢芴[39]
Fig. 13 Synthesis of methylperfluorofluorene from methyl- benzaldehyde and cyclohexanone[39]
图14 由甲基苯甲醛和丙酮合成二甲基八氢茚[40]
Fig. 14 Synthesis of dimethyl substituted octahydro-indones from methylbenzaldehyde and acetone[40]
图15 由烷基苯甲醛和甲基异丁基酮合成烷基取代的八氢茚[42]
Fig. 15 Synthesis of alkyl substituted octahydro-indones from alkylbenzaldehyde and methyl isobutyl ketone[42]
图16 由环己酮和香兰素合成二环己基甲烷和全氢芴混合物[43]
Fig. 16 Synthesis of the mixture of dicyclohexylmethane and dodecahydroflurene from cyclohexanone and vanillin[43]
图17 利用Mannnich-Diels-Alder反应合成螺环化合物[44]
Fig. 17 Synthesis of spiro-compounds by Mannich-Diels- Alder reaction[44]
图18 2-甲基呋喃和二环戊二烯Diels-Alder反应合成高密度燃料[45]
Fig. 18 Synthesis of high-density fuels from 2-methylfuran and dicyclopentadiene by Diels-Alder reaction[45]
图19 以芳樟醇为原料合成RJ-4[46]
Fig. 19 Synthesis of RJ-4 from linalool[46]
图20 以呋喃甲醇为原料合成JP-10[47]
Fig. 20 Synthesis of JP-10 from furfuryl alcohol[47]
图21 以5-甲基糠醛为原料合成RJ-4[48]
Fig. 21 Synthesis of RJ-4 from 5-methylfurfural[48]
图22 由2, 5-己二酮合成甲基环戊二烯[49?~51]
Fig. 22 Synthesis of methyl cyclopentadiene from 2, 5- hexanedione[49?~51]
图23 由木糖合成环戊二烯和甲基环戊二烯[52]
Fig. 23 Synthesis of cyclopentadiene and methyl cyclopenta- diene from xylose[52]
图24 由2-甲基-2, 4-戊二醇和对苯醌制备二甲基十氢化萘[53]
Fig. 24 Synthesis of dimethyl naphthane from 2-methyl-2, 4-pentanediol and p-quinone[53]
图25 由异戊二烯和对苯醌制备二甲基十四氢蒽[54]
Fig. 25 Synthesis of dimethyl tetradecahydroanthracenes from isophene and p-quinone[54]
图26 光催化异佛尔酮和环己烯的2+2环加成反应合成高密度燃料[57]
Fig. 26 Synthesis of high-density fuels by photo-catalytic 2+2 cycloaddition reaction from isophorone and cyclohexene[57]
图27 光催化异佛尔酮和β-蒎烯的2+2环加成反应合成高密度燃料[58]
Fig. 27 Synthesis of high-density fuels by photocatalytic 2+2 cycloaddition reaction from isophorone and β-pinene[58]
图28 通过频那醇重排合成螺环高密度燃料[59]
Fig. 28 Synthesis of spiro high-density fuels by pinacol rearrangement[59]
图29 通过碳正离子重排反应合成十氢化萘[60]
Fig. 29 Synthesis of naphthane by carbocation rearrangement [60]
图30 通过碳正离子重排反应合成二甲基十氢化萘[61]
Fig. 30 Synthesis of dimethylnaphthane by carbocation rearrangement[61]
图31 通过碳正离子重排反应一锅合成甲基和环戊基取代十氢化萘[62]
Fig. 31 Synthesis of methyl and cyclopentyl substituted naphthane by carbocation rearrangement in one-pot[62]
表1 由生物质原料合成的多环碳氢高密度航空燃料性能总结
Table 1 Properties of multi-cyclic hydrocarbon high-density aviation fuels from biomass
Feedstock Main component structure Density (20 ℃, g/mL) Freezing point (℃) Heat value (MJ/L) Viscosity (25 ℃, mm2/s) Ref
Cyclopentanone 0.866 -38 36.7 1.62 23
Cyclopentanone and
n-propanol		 0.854 < -80 38.12 2.294
(20 ℃)		 21
Cyclopentanone and benzyl alcohol 0.906 -58 39.42 9.923
(20 ℃)		 21
Cyclopentanone 0.91 — — 4.774 24
Cyclopentanone 0.943 -39.5 — — 25
2, 5-hexanedione 0.88 -48 — — 29
Linalool or
5-methylfurfural		 0.94 < -40 39.0 60
(-40 ℃)		 46,48
Furfuryl alcohol
or xylose		 0.94 -79 39.6 19
(-40 ℃)		 47
Cyclopentanone 0.87 -76 37.16 2.12 59
Cyclopentanone and cyclopentadiene 0.952 -53 40.18 5.9 44
Cyclohexanone 0.887 1.2 38.11 3.72 63
Cyclohexanone and dimedone 0.87 -26 37.81 6.589
(20 ℃)		 18
Isophorone 0.858 -51 — — 31
Cyclohexanone 0.893 -51 38.41 4.37 59
Dimedone
and cyclohexenone		 0.921 -20 39.63 8.624
(20 ℃)		 18
2-benzylphenol 0.959 -15 40.1 1752
(20 ℃)		 38
4-methylbenzaldehyde and cyclohexanone 0.99 -22 — — 39
2-methylbenzaldehyde and cyclohexanone 0.96 -3 — — 39
Cyclopentanol 0.896 -37 — — 60
Cyclohexanol and methylcyclopentane 0.88 < -51 37 22
(-40 ℃)		 61
Isophorone and cyclohexene 0.903 -55 38.77 7.2 57
Isophorone 0.892 -40 38.58 22.4 57
Isophorone and
β-pinenes		 0.911 -51 38.67 — 58
2-benzylphenol 0.876 -20 36.96 5.1
(20 ℃)		 38
Benzylalcohol and
4-ethylphenol		 0.873 -42 37.27 10.7
(20 ℃)		 34
Dimedone, benzaldehyde and acetone 0.883 -70 38.51 49.47
(20 ℃)		 18
Dimedone and 5-methylfurfural — -55 43.4 MJ/kg — 17
2-methylbenzaldehyde and t-butyl methyl ketone 0.895 -43 36.96 5.1
(20 ℃)		 42
4-ethylbenzaldehyde and t-butyl methyl ketone 0.902 -50 37.27 10.7
(20 ℃)		 42
2-methylbenzaldehyde and acetone 0.91 -44 — — 40
4-ethylbenzaldehyde and acetone 0.94 -41 — — 40
Cyclopentanone and vanillin 0.943 -35 — — 27
Cyclopentanone and vanillin 0.89 < -60 — — 28
2-methylfuran and dicyclopentadiene 0.984 -58 41.96 15.5
(20 ℃)		 45
β-Pinenes 0.94 < -30 39.5 4199
(-10 ℃)		 32
Cyclohexanone and vanillin 0.95 -17 39.3 — 43
2-methyl-2,4-pentanediol and p-quinone 0.91 -48∽-27 — — 53
Isophene and p-quinone — — 45.7 MJ/kg — 54
Cyclohexanol and methylcyclopentane 0.90 < -72 38.0 4.3
(20 ℃)		 62
Phenol and cyclopentanol 0.88 < -75 37.4 3.5 (20 ℃)
10.4 (-20 ℃)		 36
Cyclopentanone and cyclohexanone 0.905 < -50 38.67 7.6
(20 ℃)		 26
Lignin oil and cyclopentanol 0.91 < -60 39.0 5.59
(20 ℃)		 37
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