木质素衍生物制备高密度特种燃料研究进展

doi:10.11949/0438-1157.20251416

摘要/Abstract

摘要：

高密度特种燃料因具有高能量密度、低冰点等优异性能，对提升飞行器航程、载荷与机动性具有关键意义，是国防航空领域的战略性能源。目前，此类燃料主要依赖石油资源，在“碳达峰、碳中和”背景下，开发可再生替代路线尤为迫切。木质素作为木质纤维素中富含芳环结构的主要组分之一，尚未得到高效利用，其独特的环状骨架为构建高密度燃料提供了理想前体。本文系统综述了木质素平台化合物（如苯酚类、苯甲醛类、苯醌、环己酮等）转化为高密度特种燃料的研究进展，重点阐述了烷基化、羟醛缩合、Diels‑Alder反应、迈克尔加成等构建多环燃料前驱体的方法，并分析了当前合成过程中面临的挑战。未来研究需关注燃料分子结构与性能之间的构效关系，以突破高密度、高热值、低冰点难以兼具的瓶颈，还应开展全生命周期碳排放分析和技术经济性评估，为技术可持续性与产业化决策提供支撑。本综述旨在为木质素基高密度特种燃料的研究提供参考，并为其可持续开发提供思路。

关键词: 生物燃料, 生物质, 可持续性, 高密度, 木质素, 多环烷烃

Abstract:

High-density specialty fuels, possessing high energy density and low freezing point, are strategic energy sources in aviation and national defense. They can effectively enhance the flight range, payload capacity and maneuverability of aircrafts. Currently, the production of such fuels primarily relies on petroleum refining technology. To ensure aviation energy security and facilitate the achievement of dual-carbon goals, it is imperative to develop sustainable alternatives from renewable resources. Lignin, a major component of lignocellulose, is rich in aromatic structures and represents an ideal precursor for constructing high-density specialty fuels. This paper systematically reviews research progress in converting lignin-derived platform compounds (e.g., phenols, benzaldehydes, benzoquinones and cyclohexanone) into high-density specialty fuels. It highlights methods for constructing polycyclic fuel precursors, including alkylation, aldol condensation, Diels-Alder reaction and Michael addition. Furthermore, current challenges in the synthetic process are discussed. Future efforts should be directed towards understanding structure-property relationships to simultaneously achieve high density, high heating value and low freezing point. It is also essential to conduct life-cycle analysis and techno-economic assessment to support the sustainability and industrial decision-making of the technology. This review aims to provide a reference for research on lignin-based high-density fuels and offer insights for their sustainable development.

Key words: biofuel, biomass, sustainability, high density, lignin, polycyclic alkanes

中图分类号:

TQ 031.2

呼延成, 张旭, 谭艳红, 曹景沛. 木质素衍生物制备高密度特种燃料研究进展[J]. 化工学报, DOI: 10.11949/0438-1157.20251416.

Cheng HUYAN, Xu ZHANG, Yanhong TAN, Jingpei CAO. Research progress on preparing high-density specialty fuels from lignin derivatives[J]. CIESC Journal, DOI: 10.11949/0438-1157.20251416.

图/表 33

图1 高密度特种燃料性质与应用场景

Fig. 1 Properties and applications of high-density specialty fuels

图2 木质素结构及其衍生的平台化合物

Fig. 2 Structures of lignin and lignin derived platform chemicals

图3 4-乙基苯酚和苯甲醇为原料制备高密度特种燃料

Fig. 3 Preparation of high-density specialty fuel using 4-ethylphenol and benzyl alcohol as feedstocks

图4 苯酚和乙酸苄酯为原料制备高密度特种燃料

Fig. 4 Preparation of high-density specialty fuel from phenol and benzyl acetate as feedstocks

图5 苯甲醚和苯甲基醚为原料制备高密度特种燃料

Fig. 5 Preparation of high-density specialty fuel using anisole and benzyl methyl ether as feedstocks

图6 木质素油和环戊醇为原料制备高密度特种燃料

Fig. 6 Preparation of high-density specialty fuel using lignin oil and cyclopentanol as feedstocks

图7 苯酚和环己醇为原料制备高密度特种燃料

Fig. 7 Preparation of high-density specialty fuel using phenol and cyclohexanol as feedstocks

图8 木质素油为原料制备高密度特种燃料

Fig. 8 Preparation of high-density specialty fuel using lignin oil as feedstock

图9 苯酚和环戊醇为原料制备高密度特种燃料前驱体

Fig. 9 Preparation of high-density specialty fuel precursor using phenol and cyclopentanol as feedstocks

图10 愈创木酚和糠醛为原料制备高密度特种燃料

Fig. 10 Preparation of high-density specialty fuel using guaiacol and furfural as feedstocks

图11 4-甲基愈创苯酚和甲醛为原料制备高密度特种燃料

Fig. 11 Preparation of high-density specialty fuel using 4-methylguaiacol and formaldehyde as feedstocks

图12 苯酚和苯甲醇为原料制备高密度特种燃料

Fig. 12 Preparation of high-density specialty fuel using phenol and benzyl alcohol as feedstocks

图13 甲基苯甲醛和酮类化合物为原料制备高密度特种燃料

Fig. 13 Preparation of high-density specialty fuel using methylbenzaldehydes and ketones as feedstocks

图14 甲基异丁基酮和芳香醛为原料制备高密度特种燃料

Fig. 14 Preparation of high-density specialty fuel using methyl isobutyl ketone and methylbenzaldehyde as feedstocks

图15 甲基苯甲醛和环己酮为原料制备高密度特种燃料

Fig. 15 Preparation of high-density specialty fuel using methylbenzaldehyde and cyclohexanone as feedstocks

图16 甲基苯甲醛和丙酮为原料制备高密度特种燃料

Fig. 16 Preparation of high-density specialty fuel using methylbenzaldehyde and acetone as feedstocks

图17 苯甲醛和当归内酯合成可再生烷基萘

Fig. 17 Synthesis of renewable alkylnaphthalene from benzaldehyde and angelica lactone

图18 香兰素和环己酮为原料制备高密度特种燃料

Fig. 18 Synthesis of high-density specialty fuel using vanillin and cyclohexanone as feedstocks

图19 香兰素与环酮为原料制备高密度特种燃料

Fig. 19 Preparation of high-density specialty fuel using vanillin and cycloketones as feedstocks

图20 香草醛和环戊酮为原料制备高密度特种燃料

Fig. 20 Preparation of high-density specialty fuel using vanillin and cyclopentanone as feedstocks

图21 醛类化合物和1,3-环己二酮为原料制备高密度特种燃料

Fig. 21 Preparation of high-density specialty fuel using aldehydes and 1,3-cyclohexanedione as feedstocks

图22 苯甲醛、环酮和异戊二烯为原料制备高密度特种燃料

Fig. 22 Preparation of high-density specialty fuel using benzaldehyde, cycloketone and isoprene as feedstocks

图23 苯醌和MPD为原料制备高密度特种燃料

Fig. 23 Preparation of high-density specialty fuel using benzoquinone and MPD as feedstocks

图24 异戊二烯和苯醌为原料制备高密度特种燃料

Fig. 24 Preparation of high-density specialty fuel using isoprene and benzoquinone as feedstocks

图25 环戊酮与对苯醌为原料制备高密度特种燃料

Fig. 25 Preparation of high-density specialty fuel using cyclopentanone and benzoquinone as feedstocks

图26 环己酮为原料制备高密度特种燃料

Fig. 26 Preparation of high-density specialty fuel using cyclohexanone as feedstock

图27 环酮为原料制备高密度特种燃料

Fig. 27 Preparation of high-density specialty fuel using cycloketone as feedstock

图28 环己醇和甲基环戊醇为原料制备高密度特种燃料

Fig. 28 Preparation of high-density specialty fuel using cyclohexanol and methylcyclopentanol as feedstocks

图29 环己酮为原料合成甲基十氢萘路线

Fig. 29 Synthesis of methyldecalin using cyclohexanone as feedstock

图30 环戊酮和环己酮为原料制备高密度特种燃料

Fig. 30 Preparation of high-density specialty fuel using cyclopentanone and cyclohexanone as feedstocks

图31 环己酮和降冰片烯为原料制备高密度特种燃料

Fig. 31 Preparation of high-density specialty fuel using cyclohexanone and norbornene as feedstocks

图32 异佛尔酮和环己烯为原料制备高密度特种燃料

Fig. 32 Preparation of high-density specialty fuel using isophorone and cyclohexene as feedstocks

表1 石油基和木质素基高密度特种燃料性能

Table 1 Performance of petroleum-based and lignin-based high-density specialty fuels

Density (g/mL)	Combustion Heat (MJ/L)	Freezing point (℃)	Ref.
0.936	39.6	-79	[2]
0.927	39.0	-40	[2]
0.873	37.28	-42	[19]
0.956	38.9	-21.5	[20]
0.93	39.23	-40	[24]
0.91	42.89	< -60	[26]
0.918	41.2	< -55	[28]
0.865	-	< -60	[30]
0.90	41.6	-26.6	[33]
0.964	40.1	-	[35]
0.99	-	-22	[48]
0.95	39.2	-17	[53]
0.946	-	-35	[55]
0.88	39.0	-	[57]
0.943	42.3	-46	[61]
0.91	-	-48.1--37.1	[63]
0.966	43.1	-67	[69]
0.887	38.11	1.2	[70]
0.893	38.41	-51	[73]
0.876	37.1	< -110	[75]
-	-	-23.5	[80]
0.91	-	< -71	[82]
0.938	39.87	< -55	[83]
0.903	38.58	-55	[87]

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