Design and preparation of liquid polycyclic norbornanes as potential high performance fuels for aerospace propulsion

Zarezin, Danil P.; Rudakova, Marina A.; Shorunov, Sergey V.; Sultanova, M. U.; Samoilov, Vadim O.; Maximov, A. L.; Bermeshev, Maxim V.

doi:10.1016/j.fuproc.2021.107056

Cited by 18 publications

(10 citation statements)

References 36 publications

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“…The synthesis of hydrocarbons bearing two norbornane cycles at a spiro-carbon atom was a challenge. Recently, we have shown that such polycyclic compounds could demonstrate increased density and high values of volumetric heat of combustion . However, the first attempt to synthesize hydrocarbon 9 via the [4π + 2π] reaction between 6 and 2 failed due to a poor reactivity of the CC bond of 6 in the [4π + 2π] reaction and steric hindrances (Figure ).…”

Section: Resultsmentioning

confidence: 99%

“…Recently, we have shown that such polycyclic compounds could demonstrate increased density and high values of volumetric heat of combustion. 32 However, the first attempt to synthesize hydrocarbon 9 via the [4π + 2π] reaction between 6 and 2 failed due to a poor reactivity of the C�C bond of 6 in the [4π + 2π] reaction and steric hindrances (Figure 3). We decided to activate the double bond in 6 by introducing a carbonyl group to the adjacent carbon atom (10, Figure 4 and Table S1).…”

Section: Strained Hydrocarbons Frommentioning

confidence: 99%

“…Moreover, after the introduction of a certain amount of such motifs into a molecule, the volumetric heat of combustion also ceases to increase. 32 A combination of three-or four-membered cycles with norbornane moiety in one molecule has been found to be a very fruitful strategy for the development of new HED fuels possessing high volumetric heats of combustion, high densities, and good cryogenic properties (e.g., quadricyclane, 33 dicyclopropanated dienes like dicyclopentadiene, 34 norbornadiene-2,5, 34 VNB, 31 or ENB 35 ). A promising development of this strategy is the synthesis of related hydrocarbons with spirocarbon atoms (i.e., spirocycloalkanes).…”

Section: Introductionmentioning

confidence: 99%

“…However, the increase in the number of norbornane rings in a hydrocarbon fuel molecule greatly elevates freezing temperatures and viscosity. Moreover, after the introduction of a certain amount of such motifs into a molecule, the volumetric heat of combustion also ceases to increase …”

Section: Introductionmentioning

confidence: 99%

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High-Energy-Density Liquid Spiro-Norbornanes from Methylenenorbornane

et al. 2022

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We report a synthetic scheme for obtaining new spiro-hydrocarbons from a versatile norbornane derivative, methylenenorbornane. As a result, four new spiro-hydrocarbons and the isomeric-related norbornanes for the comparison have been obtained in moderate or good yields through [4π + 2π] and cyclopropanation reactions. The effect of introducing a spiro-center is dependent on the nature of carbocycles at a spiro-carbon atom. There is no obvious advantage in properties for spirocycloalkenes consisting of norbornane and cyclopropane rings at the spiro-carbon atom compared to isomeric hydrocarbons. At the same time, spirocycloalkenes with two norbornane motifs at a spiro-center have exhibited much higher values of densities and energy densities (0.992–1.023 g/mL, 41.79–43.28 MJ/L) than the related hydrocarbons without a spiro-center and JP-10. The obtained results can provide insight and an opportunity to further expand this work to bring new high-performance jet fuels to market.

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Section: Resultsmentioning

confidence: 99%

Section: Strained Hydrocarbons Frommentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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High-Energy-Density Liquid Spiro-Norbornanes from Methylenenorbornane

et al. 2022

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“…Increasing the number of strained cycles in a molecule results in higher specific energy in the case of polycyclic compounds, especially three‐cyclic compounds. The stress‐energy of small cycles has a beneficial effect on the heat of combustion [8].…”

Section: Introductionmentioning

confidence: 99%

Combustion and Thermal Decomposition Research on 1,2‐Dicyclopropyl‐1‐Methyl Cyclopropane (DMCP) as High Energy Fuel for Liquid Rocket Propellants

Sun

Zhang²,

Wang³

et al. 2022

Propellants Explo Pyrotec

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1,2-Dicyclopropyl-1-methyl cyclopropane (DMCP) was found a high-energy liquid hydrocarbon propellant. A model combustion chamber was designed and manufactured to investigate the combustion performance of DMCP and Chinese rocket kerosene (RK) in comparison. Due to the higher density of DMCP, its orifice flow coefficient was 3.4 % larger than that of RK. The chamber pressure fluctuation amplitude of DMCP was within 10 % of the average pressure value. Under typical conditions, the flame intensity of DMCP combustion flame was more intense than that of RK. When the mixture ratios varied from 2.0-2.8, the characteristic velocity changes of DMCP were between 1626 m/s and 1636 m/s. It was not apparent that the characteristic velocity of DMCP was affected by the change of mixture ratio. The combustion efficiency of DMCP increased with the rise of its mixture ratio (varying between 0.902 and 0.921), higher than that of RK in a low mixture ratio. The apparent activation energy values (E) of DMCP were 202.0 kJ • mol À 1 and 202.9 kJ • mol À 1 , respectively, according to Kissinger and Flynn-Wall-Ozawa (FWO) equations.

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Pd/C catalytic cyclopropanation of polycyclic olefins for synthesis of high‐energy‐density strained fuels

Wang

et al. 2023

AIChE Journal

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Cyclopropane derivates are appealing to synthesis of high-energy-density fuels because of the high strained energy of the three-numbered ring. The catalytic cyclopropanation of olefin with diazomethane is very effective to construct the carbocycle. The majority of the catalysts employed are nonrecyclable homogeneous compounds. Herein, we report cyclopropanation of polycyclic olefins catalyzed by heterogeneous Pd/C. The optimal cyclopropanation conditions were explored utilizing dicyclopentadiene as model substrate and a series of polycyclic olefins were cyclopropanated with high yield. Additionally, the catalyst has good recyclability and stability, as shown by characterizations as well as the fact that no inactivation happens after cyclopropanation. The synthesized cyclopropane derivates exhibit good fuel characteristics like high density (1.006-1.087 g/cm 3 ), high volumetric net heat of combustion (42.58-46.45 kJ/cm 3 ), good low-temperature and combustion performance. This work shows industrial potential for cyclopropanation of polycyclic olefins with diazomethane.

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Design and preparation of liquid polycyclic norbornanes as potential high performance fuels for aerospace propulsion

Cited by 18 publications

References 36 publications

High-Energy-Density Liquid Spiro-Norbornanes from Methylenenorbornane

High-Energy-Density Liquid Spiro-Norbornanes from Methylenenorbornane

Combustion and Thermal Decomposition Research on 1,2‐Dicyclopropyl‐1‐Methyl Cyclopropane (DMCP) as High Energy Fuel for Liquid Rocket Propellants

Pd/C catalytic cyclopropanation of polycyclic olefins for synthesis of high‐energy‐density strained fuels

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