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Progress in Chemistry 2024, Vol. 36 Issue (3): 448-462 DOI: 10.7536/PC230713 Previous Articles   

• Review •

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: Revised: Online: Published:
  • Contact: * e-mail: pp19881208@126.com (Zhanchao Li);tanfangfang@yau.edu.cn(Fangfang Tan)
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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
Fig.1 The platform molecules and derivatives from biomass
Fig. 2 Synthesis of multi-cyclopentane from cyclopentanone[23?~25]
Fig. 3 Synthesis of multi-component cycloalkane from cyclopentanone and cyclohexanone[26]
Fig. 4 Synthesis of multi-cycloalkane from cyclopentanone and vanillin[27]
Fig. 5 Synthesis of multi-cyclopentane mixture from cyclopentanone and vanillin[28]
Fig. 6 Synthesis of methyl substituted dicyclopentane and tricyclopentane from 2, 5-hexanedione[29]
Fig.7 Synthesis of multi-methyl substituted bicyclohexane from isophorone[31]
Fig. 8 Synthesis of high-density fuel from β-pinene dimerization catalyzed by Nafion[32]
Fig. 9 Synthesis of ethyl substituted dicyclohexylmethane from benzylalcohol and 4-ethylphenol[34]
Fig. 10 Synthesis of multi-cycloalkane mixture from phenol and cyclopentanol[36]
Fig. 11 Synthesis of multi-cycloalkane mixture from ligin oil and cyclopentanol[37]
Fig. 12 Synthesis of perfluorofluorene from 2- benzylphenol[38]
Fig. 13 Synthesis of methylperfluorofluorene from methyl- benzaldehyde and cyclohexanone[39]
Fig. 14 Synthesis of dimethyl substituted octahydro-indones from methylbenzaldehyde and acetone[40]
Fig. 15 Synthesis of alkyl substituted octahydro-indones from alkylbenzaldehyde and methyl isobutyl ketone[42]
Fig. 16 Synthesis of the mixture of dicyclohexylmethane and dodecahydroflurene from cyclohexanone and vanillin[43]
Fig. 17 Synthesis of spiro-compounds by Mannich-Diels- Alder reaction[44]
Fig. 18 Synthesis of high-density fuels from 2-methylfuran and dicyclopentadiene by Diels-Alder reaction[45]
Fig. 19 Synthesis of RJ-4 from linalool[46]
Fig. 20 Synthesis of JP-10 from furfuryl alcohol[47]
Fig. 21 Synthesis of RJ-4 from 5-methylfurfural[48]
Fig. 22 Synthesis of methyl cyclopentadiene from 2, 5- hexanedione[49?~51]
Fig. 23 Synthesis of cyclopentadiene and methyl cyclopenta- diene from xylose[52]
Fig. 24 Synthesis of dimethyl naphthane from 2-methyl-2, 4-pentanediol and p-quinone[53]
Fig. 25 Synthesis of dimethyl tetradecahydroanthracenes from isophene and p-quinone[54]
Fig. 26 Synthesis of high-density fuels by photo-catalytic 2+2 cycloaddition reaction from isophorone and cyclohexene[57]
Fig. 27 Synthesis of high-density fuels by photocatalytic 2+2 cycloaddition reaction from isophorone and β-pinene[58]
Fig. 28 Synthesis of spiro high-density fuels by pinacol rearrangement[59]
Fig. 29 Synthesis of naphthane by carbocation rearrangement [60]
Fig. 30 Synthesis of dimethylnaphthane by carbocation rearrangement[61]
Fig. 31 Synthesis of methyl and cyclopentyl substituted naphthane by carbocation rearrangement in one-pot[62]
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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