Progress on using biomass derivatives to replace petroleum for synthesis of high-density fuels
-
摘要: “碳达峰、碳中和”目标的提出,为中国能源结构转型提供了动力引擎。发展生物质基高密度燃料,既可以为传统石油基高密度燃料提供可再生的替代品,又符合中国可持续发展以及能源结构转型的要求。本文综述了RJ-4、JP-10等典型石油基高密度燃料的性质和用途,总结了由萜类以及木质纤维素平台化合物合成RJ-4、JP-10以及其他多环燃料的路线方法,展示了生物质转化制备高密度燃料的良好可行性,讨论了目前生物质基高密度燃料研究面临的瓶颈以及发展方向。Abstract: The goal of “carbon peak and carbon neutrality” provides a powerful engine for the transformation of energy structure in China. As response to the sustainable development and energy structure transformation, the development of biomass high-density fuels is necessary, which can provide renewable alternatives for traditional petroleum-based high-density fuels. Herein, the properties and applications of typical petroleum-based high-density fuels including RJ-4 and JP-10 are reviewed. We also introduce the routes for synthesizing RJ-4, JP-10 and other polycyclic fuels from terpenoids and lignocellulose platform compounds, showing the feasibility of converting biomass to high-density fuels. Finally, we emphasize the current bottlenecks and development trends in the synthesis and application of biomass high-density fuels.
-
Key words:
- high-density fuels /
- biomass /
- polycyclic fuels /
- terpenoids /
- lignocellulose
-
表 1 典型石油基高密度燃料性质
Table 1 Properties of typical fossil-based high-density fuels
表 2 萜类化合物二聚燃料性质
Table 2 Properties of terpene dimer fuels
Monomer Heat value/
(MJ·kg−1)Density/
(g·mL−1)Viscosity(40 ℃)/
(mm2·s−1)α-pinene 42.047 0.935 34.68 β-pinene 42.118 0.938 35.05 Limonene 41.906 0.914 25.86 Camphene 40.063 0.941 34.96 表 3 联环燃料的结构及主要性质
Table 3 Structure and properties of multi-cyclic fuels
Feedstock Main component structure Density(20 ℃)/
(g·mL−1)Freezing point/℃ Heat value/
(MJ·kg−1)Viscosity/(mm2·s−1) Ref Isophorone 0.858 −51 − − [32] Cyclohexanone 0.887 1.2 42.97 3.72 (25°C),
6.33 (5°C)[31] Cyclopentanone 0.867 −38 42.42 1.62 (25 ℃),
4.68 (−35 ℃)[31] Cyclopentanone 0.91 − − 4.774 (25 ℃) [33] Cyclopentanone 0.943 −39.5 − − [34] 表 4 螺环燃料的结构及主要性质
Table 4 Structure and properties of spiro fuels
Feedstock Main component structure Density (20 ℃)/
(g·mL−1)Freezing point/℃ Heat value/
(MJ·kg−1)Viscosity/
(mm2·s−1)Ref Cyclopentanone 0.870 −76 42.72 2.12 (25 ℃),
3.33 (0 ℃),
19.8 (−60 ℃)[35] Cyclohexanone 0.893 −51 43.01 4.37 (25°C),
8.59 (5°C),
232.3 (−20 ℃)[35] Cyclohexanone, formaldehyde and cyclopentadiene 0.952 −53 42.21
40.185.9 (25 ℃)
11.4 (0 ℃),
61.9 (−40 ℃)[36] Isophorone and
β-pinene0.911 −51 42.45
38.673 (20 ℃)
15 (0 ℃),
176 (−20 ℃)[37] 表 5 稠环燃料的结构及性质
Table 5 Structure and properties of fused-ring fuels
Feedstock Main component structure Density (20 ℃)/
(g·mL−1)Freezing point/℃ Heat value/
(MJ·L−1)Viscosity/
(mm2·s−1)Ref Cyclopentanone ~0.87 −44 − − [39] Cyclohexanone ~0.88 (−51)− (−110) ~37 ~22 (−40 ℃) [41] Phenol, anisole or guaiacol and benzyl ether or benzyl alcohols 0.96 −15 40.1 1752 (20 ℃) [42] Cyclohexanone and 2-methyl benzaldehyde 0.99 −22 − − [44] Cyclohexanone and 4-methyl benzaldehyde 0.96 −3 − − [44] Acetone and 2-methyl benzaldehyde 0.91 −44 − − [46] Acetone and 4-methyl benzaldehyde 0.94 −41 − − [46] -
[1] 潘伦, 邓强, 鄂秀天凤, 聂根阔, 张香文, 邹吉军. 高密度航空航天燃料合成化学[J]. 化学进展,2015,27(11):1531−1541.PAN Lun, DENG Qiang, E Xiu-tian-feng, NIE Gen-kuo, ZHANG Xiang-wen, ZOU Ji-jun. Synthesis chemistry of high-density fuels for aviation and aerospace propulsion[J]. Prog Chem,2015,27(11):1531−1541. [2] 邹吉军, 张香文, 王莅, 米镇涛. 高密度液体碳氢燃料合成及应用进展[J]. 含能材料,2007,15(4):411−415. doi: 10.3969/j.issn.1006-9941.2007.04.030(ZOU Ji-jun, ZHANG Xiang-wen, WANG Li, MI Zhen-tao. Progress in synthesis and application of high-density liquid hydrocarbon fuels[J]. Chin J Energy Mater,2007,15(4):411−415. doi: 10.3969/j.issn.1006-9941.2007.04.030 [3] 邹吉军, 郭成, 张香文, 王莅, 米镇涛. 航天推进用高密度液体碳氢燃料: 合成与应用[J]. 推进技术,2014,35(10):1419−1425.ZOU Ji-jun, GUO Cheng, ZHANG Xiang-wen, WANG Li, MI Zhen-tao. High-density liquid hydrocarbon fuels for aerospace propulsion: synthesis and application[J]. J Propul Technol,2014,35(10):1419−1425. [4] ZHANG X W, PAN L, WANG L, ZOU J-J. Review on synthesis and properties of high-energy-density liquid fuels: Hydrocarbons, nanofluids and energetic ionic liquids[J]. Chem Eng Sci,2018,180:95−125. doi: 10.1016/j.ces.2017.11.044 [5] CHUNG H S, CHEN C S H, KREMER R A, BOULTON J R, BURDETTE G W. Recent developments in high-energy density liquid hydrocarbon fuels[J]. Energy Fuels,1999,13(3):641−649. doi: 10.1021/ef980195k [6] EDWARDS T. Liquid fuels and propellants for aerospace propulsion: 1903−2003[J]. J Propul Power,2003,19(6):1089−1107. doi: 10.2514/2.6946 [7] JANOSKI E J, SCHNEIDER A, WARE R E. Process for isomerization of tetrahydrodimethyldicyclopentadiene: US, 4288644A[P]. 1981-09-08. [8] JANOSKI E J, MITCHELL R E, SCHNEIDER A. Continuous process for conversion of dimethydicyclopentadiene to endo-dimethyldicyclopentadiene, a missile fuel: US, 4177217A[P]. 1979-12-04. [9] COHEN C A, MUESSIG C W. Jet and rocket fuel: US, 3381046A[P]. 1968-04-30. [10] 熊中强, 米镇涛, 张香文, 邢恩会. 合成高密度烃类燃料研究进展[J]. 化学进展,2005,17(2):359−367. doi: 10.3321/j.issn:1005-281X.2005.02.022XIONG Zhong-qiang, MI Zhen-tao, ZHANG Xiang-wen, XING En-hui. Development of synthesized high-density hydrocarbon fuels[J]. Prog Chem,2005,17(2):359−367. doi: 10.3321/j.issn:1005-281X.2005.02.022 [11] GEORGE W, BURDETTE R, HALL L. Low viscosity air breathing missile fuel: US, 4427467A[P]. 1984-01-24. [12] SCHNEIDER A, WARE R, JANOSKI E J. Isomerization of endo-tetrahydrodicyclopentadiene to a missile fuel diluent: US, 4086284A[P]. 1978-04-25. [13] LI Y H, ZOU J-J, ZHANG X W, WANG L, MI Z T. Product distribution of tricyclopentadiene from cycloaddition of dicyclopentadiene and cyclopentadiene: A theoretical and experimental study[J]. Fuel,2010,89(9):2522−2527. doi: 10.1016/j.fuel.2009.11.020 [14] BOULTON J R, KREMER R A. Oligomers of cyclopentadiene and process for making them: US, 5446222A[P]. 1995-8-29. [15] 谢嘉维, 张香文, 谢君健, 聂根阔, 潘伦, 邹吉军. 由生物质合成高密度喷气燃料[J]. 化学进展,2018,30(9):1424−1433.XIE Jia-wei, ZHANG Xiang-wen, XIE Jun-jian, NIE Gen-kuo, PAN Lun, ZOU Ji-jun. Synthesis of high-density jet fuels from biomass[J]. Prog Chem,2018,30(9):1424−1433. [16] ZOU J-J, ZHANG X W, PAN L. High-Energy-Density Fuels for Advanced Propulsion: Design and Synthesis[M]. New Jersey: Wiley, 2020: 241-289. [17] YANG X K, LI T, TANG K, ZHOU X P, LU M, OUNKHAM W L, SPAIN S M, FROST B J, LIN H F. Highly efficient conversion of terpenoid biomass to jet-fuel range cycloalkanes in a biphasic tandem catalytic process[J]. Green Chem,2017,19(15):3566−3573. doi: 10.1039/C7GC00710H [18] HARVEY B G, WRIGHT M E, QUINTANA R L. High-density renewable fuels based on the selective dimerization of pinenes[J]. Energy Fuels,2010,24(1):267−273. doi: 10.1021/ef900799c [19] XU J, ZHU P, LIU X Y, YANG X Q, SHAN S Y, MA Y, PAN D, DONG B B, GUO Z H. Preparation of high-density fuel through dimerization of β-pinene[J]. Chem Eng Technol,2020,43(11):2259−2265. doi: 10.1002/ceat.202000250 [20] BELLER H R, LEE T S, KATZ L. Natural products as biofuels and bio-based chemicals: Fatty acids and isoprenoids[J]. Nat Prod Rep,2015,32(10):1508−1526. doi: 10.1039/C5NP00068H [21] YANG X K, UDDIN M H, ZHOU X P, NEUPANE B, MILLER G C, CORONELLA C J, POULSON S R, LIN H F. Production of high-density renewable aviation fuel from arid land crop[J]. ACS Sustainable Chem Eng,2018,6(8):10108−10119. doi: 10.1021/acssuschemeng.8b01433 [22] 邹吉军, 张香文, 王莅, 王庆法. 一种含生物燃料的混合喷气燃料及其制备方法: 中国, 103013589A[P]. 2013-04-03.ZOU Ji-jun, ZHANG Xiang-wen, WANG Li, WANG Qing-fa. A mixed jet fuel containing biofuels and its preparation method: CN, 103013589A[P]. 2013-04-03. [23] ZOU J-J, CHANG N, ZHANG X W, WANG L. Isomerization and dimerization of pinene using Al-incorporated MCM-41 mesoporous materials[J]. ChemCatChem,2012,4(9):1289−1297. doi: 10.1002/cctc.201200106 [24] MEYLEMANS H A, QUINTANA R L, HARVEY B G. Efficient conversion of pure and mixed terpene feedstocks to high density fuels[J]. Fuel,2012,97:560−568. doi: 10.1016/j.fuel.2012.01.062 [25] HARVEY B G, MEYLEMANS H A, GOUGH R V, QUINTANA R L, GARRISON M D, BRUNO T J. High-density biosynthetic fuels: the intersection of heterogeneous catalysis and metabolic engineering[J]. Phys Chem Chem Phys,2014,16(20):9448−9457. doi: 10.1039/C3CP55349C [26] ISIKGOR F H, BECER C R. Lignocellulosic biomass: a sustainable platform for the production of bio-based chemicals and polymers[J]. Polym Chem,2015,6(25):4497−4559. doi: 10.1039/C5PY00263J [27] ULONSKA K, VOLL A, MARQUARDT W. Screening pathways for the production of next generation biofuels[J]. Energy Fuels,2016,30(1):445−456. doi: 10.1021/acs.energyfuels.5b02460 [28] MOTAGAMWALA A H, WON W, MARAVELIAS C T, DUMESIC J A. An engineered solvent system for sugar production from lignocellulosic biomass using biomass derived gamma-valerolactone[J]. Green Chem,2016,18(21):5756−5763. doi: 10.1039/C6GC02297A [29] 袁正求, 龙金星, 张兴华, 夏莹, 王铁军, 马隆龙. 木质纤维素催化转化制备能源平台化合物[J]. 化学进展,2016,28(1):103−110. doi: 10.7536/PC150744YUAN Zheng-qiu, LONG Jin-xing, ZHANG Xing-hua, XIA Ying, WANG Tie-jun, MA Long-long. Catalytic conversion of lignocellulose into energy platform chemicals[J]. Prog Chem,2016,28(1):103−110. doi: 10.7536/PC150744 [30] YANG J F, LI N, LI G Y, WANG W T, WANG A Q, WANG X D, CONG Y, ZHANG T. Synthesis of renewable high-density fuels using cyclopentanone derived from lignocellulose[J]. Chem Commun,2014,50(20):2572−2574. doi: 10.1039/c3cc46588h [31] DENG Q, NIE G K, PAN L, ZOU J-J, ZHANG X W, WANG L. Highly selective self-condensation of cyclic ketones using MOF-encapsulating phosphotungstic acid for renewable high-density fuel[J]. Green Chem,2015,17(8):4473−4481. doi: 10.1039/C5GC01287B [32] WANG W, LIU Y T, LI N, LI G Y, WANG W T, WANG A Q, WANG X D, ZHANG T. Synthesis of renewable high-density fuel with isophorone[J]. Sci Rep,2017,7:6111. doi: 10.1038/s41598-017-06556-7 [33] SHENG X R, LI G Y, WANG W T, CONG Y, WANG X D, HUBER G W, LI N, WANG A Q, ZHANG T. Dual-bed catalyst system for the direct synthesis of high density aviation fuel with cyclopentanone from lignocellulose[J]. AIChE J,2016,62(8):2754−2761. doi: 10.1002/aic.15248 [34] WANG W, LI N, LI G Y, LI S S, WANG W T, WANG A Q, CONG Y, WANG X D, ZHANG T. Synthesis of renewable high-density fuel with cyclopentanone derived from hemicellulose[J]. ACS Sustainable Chem Eng,2017,5(2):1812−1817. doi: 10.1021/acssuschemeng.6b02554 [35] XIE J J, ZHANG X W, PAN L, NIE G K, E X T F, LIU Q, WANG P, LI Y F, ZOU J-J. Renewable high-density spiro-fuels from lignocellulose-derived cyclic ketones[J]. Chem Commun,2017,53(74):10303−10305. doi: 10.1039/C7CC05101H [36] PAN L, XIE J J, NIE G K, LI Z, ZHANG X W, ZOU J-J. Zeolite catalytic synthesis of high-performance jet-fuel-range spiro-fuel by one-pot Mannich-Diels-Alder reaction[J]. AIChE J,2019,66(1):e16789. [37] XIE J J, PAN L, NIE G K, XIE J W, LIU Y K, MA C, ZHANG X W, ZOU J-J. Photoinduced cycloaddition of biomass derivatives to obtain high-performance spiro-fuel[J]. Green Chem,2019,21(21):5886−5895. doi: 10.1039/C9GC02790D [38] ROAN M A, BOEHMAN A L. The effect of fuel composition and dissolved oxygen on deposit formation from potential JP-900 basestocks[J]. Energy Fuels,2004,18(3):835−843. doi: 10.1021/ef034050b [39] TANG H, CHEN F, LI G Y, YANG X F, HU Y C, WANG A Q, CONG Y, WANG X D, ZHANG T, LI N. Synthesis of jet fuel additive with cyclopentanone[J]. J Energy Chem,2019,29:23−30. doi: 10.1016/j.jechem.2018.01.017 [40] WANG R, LI G Y, TANG H, WANG A Q, XU G L, CONG Y, WANG X D, ZHANG T, LI N. Synthesis of decaline-type thermal-stable jet fuel additives with cycloketones[J]. ACS Sustainable Chem Eng,2019,7(20):17354−17361. doi: 10.1021/acssuschemeng.9b04288 [41] NIE G K, ZHANG X W, PAN L, WANG M, ZOU J-J. One-pot production of branched decalins as high-density jet fuel from monocyclic alkanes and alcohols[J]. Chem Eng Sci,2018,180:64−69. doi: 10.1016/j.ces.2018.01.024 [42] NIE G K, ZHANG X W, HAN P J, XIE J J, PAN L, WANG L, ZOU J-J. Lignin-derived multi-cyclic high density biofuel by alkylation and hydrogenated intramolecular cyclization[J]. Chem Eng Sci,2017,158:64−69. doi: 10.1016/j.ces.2016.10.003 [43] NIE G K, ZHANG X W, PAN L, HAN P J, XIE J J, LI Z, XIE J W, ZOU J-J. Hydrogenated intramolecular cyclization of diphenylmethane derivatives for synthesizing high-density biofuel[J]. Chem Eng Sci,2017,173:91−97. doi: 10.1016/j.ces.2017.07.034 [44] XU J L, LI N, LI G Y, HAN F A, WANG A Q, CONG Y, WANG X D, ZHANG T. Synthesis of high-density aviation fuels with methyl benzaldehyde and cyclohexanone[J]. Green Chem,2018,20(16):3753−3760. doi: 10.1039/C8GC01628C [45] ZHANG X J, HAN F G, LIN S Z, CHEN F, SUN M J, LIU J J, LI G Y, TANG H, WANG A Q, CONG Y, LI N. Synthesis of branched octahydro-indene with methyl benzaldehyde and methyl isobutyl ketone[J]. ACS Sustainable Chem Eng,2019,7(14):12023−12031. [46] TIMOTHY A A, HAN F G, LI G Y, XU J L, WANG A Q, CONG Y, LI N. Synthesis of jet fuel range high-density dicycloalkanes with methyl benzaldehyde and acetone[J]. Sustainable Energy Fuels,2020,4(11):5560−5567. doi: 10.1039/D0SE01110J [47] JIA T H, ZHANG X W, LIU Y, GONG S, DENG C, PAN L, ZOU J-J. A comprehensive review of the thermal oxidation stability of jet fuels[J]. Chem Eng Sci,2021,229:116157. doi: 10.1016/j.ces.2020.116157 [48] CHAMBON F, RATABOUL F, PINEL C, CABIAC A, GUILLON E, ESSAYEM N. Conversion of cellulose to 2,5-hexanedione using tungstated zirconia in hydrogen atmosphere[J]. Appl Catal A: Gen,2015,504:664−671. doi: 10.1016/j.apcata.2015.02.042 [49] LIU Y T, LI G Y, HU Y C, WANG A Q, LU F, ZOU J-J, CONG Y, LI N, ZHANG T. Integrated conversion of cellulose to high-density aviation fuel[J]. Joule,2019,3(4):1028−1036. doi: 10.1016/j.joule.2019.02.005 [50] LI S S, CHEN F, LI N, WANG W T, SHENG X R, WANG A Q, CONG Y, WANG X D, ZHANG T. Synthesis of renewable triketones, diketones, and jet-fuel range cycloalkanes with 5-hydroxymethylfurfural and ketones[J]. ChemSusChem,2016,10(4):711−719. [51] REN D Z, SONG Z Y, LI L, LIU Y J, JIN F M, HUO Z B. Production of 2,5-hexanedione and 3-methyl-2-cyclopenten-1-one from 5-hydroxymethylfurfural[J]. Green Chem,2016,18(10):3075−3081. doi: 10.1039/C5GC02493E [52] SACIA E R, DEANER M H, YING L L, BELL A T. Synthesis of biomass-derived methycyclopentane as a gasoline additive via aldol condensation/hydrodeoxygenation of 2, 5-hexanedione[J]. Green Chem,2015,17(4):2393−2397. doi: 10.1039/C4GC02292K [53] NISHIMURA S, OHMATSU S, EBITANI K. Selective synthesis of 3-methyl-2-cyclopentenone via intramolecular aldol condensation of 2, 5-hexanedione with gamma-Al2O3/AlOOH nanocomposite catalyst[J]. Fuel Process Technol,2019,196:106185. doi: 10.1016/j.fuproc.2019.106185 [54] MONICA N, GIOVANNI S, PAOLA C, MANUELA O, ANTONIO P. Eco-friendly stereoselective reduction of α, β-unsaturated carbonyl compounds by Er(OTf)3/NaBH4 in 2-MeTHF[J]. Tetrahedron,2015,71(7):1132−1135. doi: 10.1016/j.tet.2014.12.005 [55] FORKEL N V, HENDERSON D A, FUCHTER M J. Lanthanide replacement in organic synthesis: Luche-type reduction of alpha, beta-unsaturated ketones in the presence of calcium triflate[J]. Green Chem,2012,14(8):2129−2132. doi: 10.1039/c2gc35619h [56] HOYE T R, ZHAO H. Some allylic substituent effects in ring-closing metathesis reactions: allylic alcohol activation[J]. Org Lett,1999,1(7):1123−1125. doi: 10.1021/ol990947+ [57] MEYLEMANS H A, QUINTANA R L, GOLDSMITH B R, HARVEY B G. Solvent-free conversion of linalool to methylcyclopentadiene dimers: a route to renewable high-density fuels[J]. ChemSusChem,2011,4(4):465−469. doi: 10.1002/cssc.201100017 [58] NIE G K, SHI C X, DAI Y Y, LIU Y N, LIU Y K, MA C, LIU Q, PAN L, ZHANG X W, ZOU J-J. Producing methylcyclopentadiene dimer and trimer based high-performance jet fuels using 5-methyl furfural[J]. Green Chem,2020,22(22):7765−7768. doi: 10.1039/D0GC02361B [59] WOODROFFE J D, HARVEY B G. Synthesis of bio-based methylcyclopentadiene from 2, 5-hexanedione: a sustainable route to high energy density jet fuels[J]. ChemSusChem,2020,14(1):339−343. [60] LIU Y T, WANG R, QI H F, LIU X Y, LI G Y, WANG A Q, WANG X D, CONG Y, ZHANG T, LI N. Synthesis of bio-based methylcyclopentadiene via direct hydrodeoxygenation of 3-methylcyclopent-2-enone derived from cellulose[J]. Nat Commun,2021,12(1):46. doi: 10.1038/s41467-020-20264-3 [61] WANG R, LIU Y T, LI G Y, WANG A Q, WANG X D, CONG Y, ZHANG T, LI N. Direct synthesis of methylcyclopentadiene with 2,5-hexanedione over zinc molybdates[J]. ACS Catal,2021,11(8):4810−4820. doi: 10.1021/acscatal.1c00223 [62] LI G Y, HOU B L, WANG A Q, XIN X L, CONG Y, WANG X D, LI N, ZHANG T. Making JP-10 superfuel affordable with a lignocellulosic platform compound[J]. Angew Chem Int Ed,2019,58(35):12154−12158. doi: 10.1002/anie.201906744 [63] LI G Y, LI N, ZHENG M Y, LI S S, WANG A Q, CONG Y, WANG X D, ZHANG T. Industrially scalable and cost-effective synthesis of 1,3-cyclopentanediol with furfuryl alcohol from lignocellulose[J]. Green Chem,2016,18(12):3607−3613. doi: 10.1039/C6GC00341A