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[2+2] and [2+1] cycloaddition of myrcene for synthesis of highly strained bio-fuels with high density and high impulse

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Názov: [2+2] and [2+1] cycloaddition of myrcene for synthesis of highly strained bio-fuels with high density and high impulse
Autori: Jin-xiu Hu, Min-hua Ai, Xian-long Liu, Xiao-lei Guo, Cheng-xiang Shi, Kang Xue, Xiang-wen Zhang, Li Wang, Ji-Jun Zou, Lun Pan
Zdroj: Energetic Materials Frontiers, Vol 6, Iss 1, Pp 84-94 (2025)
Informácie o vydavateľovi: Elsevier BV, 2025.
Rok vydania: 2025
Predmety: [2+1] cycloaddition, Triplet energy transfer mechanism, Chemical technology, Myrcene, TP1-1185, High-energy-density fuel, [2+2] photocycloaddition
Popis: Developing bio-fuels provides a sustainable strategy to reduce the dependence on finite fossil fuels. But biomass-based fuel molecules usually lack strained structure, resulting in undesirable density and impulse for aerospace applications. Herein, the highly strained bio-fuels are synthesized from myrcene by photoinduced [2 + 2] cycloaddition and hydrogenation/cyclopropanation reactions. The triplet energy transfer mechanism is revealed through theoretical calculations, triplet quenching experiments and phosphorescent measurement. The reaction conditions of photocycloaddition reaction are optimized, including the photosensitizer type and amount, solvent effect, substrate concentration, reaction temperature and light intensity. Under the optimal conditions, the yield of target photocycloaddition product reaches ca. 82.61 %, which is then hydrogenated and cyclopropanized to two kinds of bio-fuels, namely PC@HG and PC@CP, respectively, which have high density of 0.836 and 0.886 g mL−1, high impulse of 326.71 and 329.42 s, superior cryogenic properties, and good combustion properties. This work provides a feasible pathway for the preparation of highly strained bio-fuels with high density and high impulse.
Druh dokumentu: Article
Jazyk: English
ISSN: 2666-6472
DOI: 10.1016/j.enmf.2024.11.006
Prístupová URL adresa: https://doaj.org/article/caec0d792ded43f0980254e41060f909
Rights: CC BY NC ND
Prístupové číslo: edsair.doi.dedup.....51611699b1a3a64d2d41ef5870305984
Databáza: OpenAIRE
Popis
Abstrakt:Developing bio-fuels provides a sustainable strategy to reduce the dependence on finite fossil fuels. But biomass-based fuel molecules usually lack strained structure, resulting in undesirable density and impulse for aerospace applications. Herein, the highly strained bio-fuels are synthesized from myrcene by photoinduced [2 + 2] cycloaddition and hydrogenation/cyclopropanation reactions. The triplet energy transfer mechanism is revealed through theoretical calculations, triplet quenching experiments and phosphorescent measurement. The reaction conditions of photocycloaddition reaction are optimized, including the photosensitizer type and amount, solvent effect, substrate concentration, reaction temperature and light intensity. Under the optimal conditions, the yield of target photocycloaddition product reaches ca. 82.61 %, which is then hydrogenated and cyclopropanized to two kinds of bio-fuels, namely PC@HG and PC@CP, respectively, which have high density of 0.836 and 0.886 g mL−1, high impulse of 326.71 and 329.42 s, superior cryogenic properties, and good combustion properties. This work provides a feasible pathway for the preparation of highly strained bio-fuels with high density and high impulse.
ISSN:26666472
DOI:10.1016/j.enmf.2024.11.006