Synthesis and properties of high-energy-density hydrocarbons based on 5-vinyl-2-norbornene

Shorunov, Sergey V.; Zarezin, Danil P.; Samoilov, Vadim O.; Rudakova, Marina A.; Борисов, Р. С.; Maximov, A. L.; Бермешев, М. В.

doi:10.1016/j.fuel.2020.118935

Cited by 22 publications

(6 citation statements)

References 28 publications

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“…Recently, we have described the synthesis and studied the properties of a number of related norbornanecontaining hydrocarbons based on 5-vinyl-2-norbornene [14]. Some of these hydrocarbons proved to have significantly better properties than JP-10.…”

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confidence: 99%

Novel Strained Alicyclic Hydrocarbons Based on 5-Methylene-2-norbornene

et al. 2021

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The paper describes the synthesis of novel strained hydrocarbons based on a diene of the norbornene series, namely 5-methylene-2-norbornene, using catalytic cyclopropanation with diazomethane. The study demonstrated the possibility of selective cyclopropanation solely along the endocyclic double bond. The physicochemical properties of the hydrocarbons were investigated systematically. These hydrocarbons were shown to have an advantageous combination of high density, low freezing point, and high energy density value. The study’s findings indicate that the compounds synthesized are promising as a component of high-energy-density fuels for modern jet engines.

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confidence: 99%

Novel Strained Alicyclic Hydrocarbons Based on 5-Methylene-2-norbornene

et al. 2021

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“…7 The cyclopropanation products of derivates such as norbornene and dicyclopentadiene (DCPD) have density of 0.891-1.080 g/cm 3 and VHOC of 37.94-45.38 kJ/cm 3 . [8][9][10][11][12] Additionally, the strained biofuels produced from cyclopropanation of biobased monoterpenes and sesquiterpenes exhibit good properties with the density of 0.855-0.965 g/cm 3 and VHOC of 37.10-41.51 kJ/cm 3 . [13][14][15][16] To construct the smallest carbocycle, several methodologies have been established, such as Simmons-Smith cyclopropanation, diazoderived carbenoids, free carbenes, cycloisomerization, nucleophilic displacement reactions, and so on.…”

Section: Introductionmentioning

confidence: 99%

“…For intense, quadricyclane (QC) with two cyclopropane rings has the density and volumetric net heat of combustion (VHOC) of 0.982 g/cm 3 and 43.55 kJ/cm 3 , respectively 7 . The cyclopropanation products of derivates such as norbornene and dicyclopentadiene (DCPD) have density of 0.891–1.080 g/cm 3 and VHOC of 37.94–45.38 kJ/cm 3 8–12 . Additionally, the strained biofuels produced from cyclopropanation of bio‐based monoterpenes and sesquiterpenes exhibit good properties with the density of 0.855–0.965 g/cm 3 and VHOC of 37.10–41.51 kJ/cm 3 13–16 …”

Section: Introductionmentioning

confidence: 99%

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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“…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%

“…The presence of three or four-membered cycle rings in a hydrocarbon usually improves the gravimetric heat of combustion and low-temperature properties. − At the same time, such fuels exhibit low or moderate values of density and volumetric heat of combustion. High values of density and volumetric heat of combustion can be reached when using norbornane compounds ( exo -tetrahydrodicyclopentadiene, isomerized tetrahydrotricyclopentadiene, bis-norbornanyl). However, the increase in the number of norbornane rings in a hydrocarbon fuel molecule greatly elevates freezing temperatures and viscosity.…”

Section: Introductionmentioning

confidence: 99%

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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Synthesis and properties of high-energy-density hydrocarbons based on 5-vinyl-2-norbornene

Cited by 22 publications

References 28 publications

Novel Strained Alicyclic Hydrocarbons Based on 5-Methylene-2-norbornene

Novel Strained Alicyclic Hydrocarbons Based on 5-Methylene-2-norbornene

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

High-Energy-Density Liquid Spiro-Norbornanes from Methylenenorbornane

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