Synthesis of New High-Energy/High-Density Hydrocarbon Fuel Systems

Marchand, Alan P.; Ramanaiah, K. Venkata; Alihodzic, S; Namboothiri, Irishi N. N.; Dong, Enbo; Aavula, B; Lewis, Samuel A.; Bott, Sascha

doi:10.1201/9781420040685.ch3

Cited by 4 publications

(5 citation statements)

References 1 publication

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“…The high volumetric energy density arises mostly from the fact that these materials tend to be denser than normal hydrocarbons; however, the built-in strain energy raises the possibility of unusual combustion mechanisms because substantial energy may be released early in the combustion process. There is interest − in trying to tailor the physical and chemical properties of these potential fuel molecules by functionalization. Since synthesis is nontrivial, new molecules are typically available only in milligram quantities, while standard methods for screening combustion/pyrolysis behavior require substantially larger samples.…”

Section: Introductionmentioning

confidence: 99%

Pyrolysis Chemistry of Cubane and Methylcubane: The Effect of Methyl Substitution on Stability and Product Branching

Anderson

2003

J. Phys. Chem. A

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Pyrolysis reactions of cubane and methylcubane were studied in a micro-flow tube reactor from room temperature to 1000 K. The composition of the flow tube eluent was probed by chemical ionization, followed by analysis in a tandem, guided-beam mass spectrometer. It was found that cubane and methylcubane have nearly identical breakdown temperature dependence, suggesting that methyl functionalization has minimal effect on the stability of cubane cage bonds. There is, however, a substantial effect of the methyl group on product branching, resulting in more stable isomers at intermediate temperatures, and a propensity to eliminate fragments containing the methyl group at high temperatures. Ab initio calculations performed to aid interpretation are discussed, along with possible mechanisms.

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Section: Introductionmentioning

confidence: 99%

Pyrolysis Chemistry of Cubane and Methylcubane: The Effect of Methyl Substitution on Stability and Product Branching

Anderson

2003

J. Phys. Chem. A

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“…4 It does have some features that make it attractive as a fuel additive in PDE applications, however. MPCU has shown itself to be capable of increasing de agration speeds of JP-10 by a factor of ve (Ref.…”

Section: Experimental Results: Jp-10 With Additivesmentioning

confidence: 99%

Ignition Delay for Jet Propellant 10/Air and Jet Propellant 10/High-Energy Density Fuel/Air Mixtures

Mikolaitis

Segal

Chandy

2003

Journal of Propulsion and Power

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Jet propellant 10 [(JP-10) or exotetrahydrodicyclopentadiene]is one of the leading candidate fuels for use in pulse detonation engine applications.As such, its ignition delay characteristics have been studied previously in very dilute mixtures at pressures from 1 to 9 atm and temperatures from 1300 to 1670 K. The ignition delay times are studied of JP-10/air and JP-10 blended with methylated PCU alkene dimer, nitronorbornane, dinitronorbornane, and ethylhexyl nitrate in air at pressures from 10 to 25 atm and temperatures from 1200 to 2500 K using a shock tube. Ignition delays were primarily measured using CH emission and secondarily using OH emission. Ignition delays were essentially insensitive to all of the additives tested. Additionally, ignition delays for dicyclopentadiene (a suspected intermediate in the combustion of JP-10) were also tested. Above 1500 K, multiple peaks in the CH emission were found. Further tests using OH emission indicate that the main peak in CH emission at these higher temperatures is probably due to reactions involved in the approach to equilibrium and give spuriously long ignition delay times.

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“…White solid (243 mg, 86% yield). 1 H NMR (500 MHz, CDCl 3 ): δ 6.17− 6.16 (m, 1H), 6.02−6.01 (m, 1H), 5.85−5.77 (m, 1H), 5.20 (d,J = 17.3 Hz,1H),5.12 (d,J = 10.5 Hz,1H),1H), 4.06 (dd, J = 4.9 Hz, 13.1 Hz, 1H), 3.88 (dd, J = 4.9 Hz, 13.0 Hz, 1H), 3.72 (s, 1H), 3.62 (s, 1H), 2.62 (s, 1H), 2.58 (s, 1H), 2.48−2.47 (m, 1H), 2.27−2.24 (m, 3H), 2.07 (s, 2H), 1.79 (d, J = 8.3 Hz, 1H), 1.59 (d, J = 10.5 Hz, 1H), 1.37 (d,J = 8.5 Hz,1H),1.13 (d,J = 10.4 Hz, 1H) ppm. 13 C{ 1 H} NMR (125 MHz, CDCl 3 ): δ 134.6, 134.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Synthetic Approach toward Diverse Oxa-Cages via Olefin Metathesis

Kotha,

Mehta,

Jena

2024

J. Org. Chem.

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This article demonstrates a late-stage modification of the cage propellanes that are transformed into intricate oxa-cycles via ringrearrangement metathesis (RRM) and regioselective ring-closing metathesis (RCM) as crucial steps. In addition, we also report the extended pentacycloundecane (PCUD)-based oxa-cages involving the domino cycloetherification followed by olefin metathesis. These oxa-cages involve a domino sequence in which the PCUD core unit remains intact. [Ru]based Grubbs catalysts are used to execute the metathesis step to assemble these higher-order oxa-cage systems. Spectroscopic data assigned structures of various products and were further supported by singlecrystal X-ray diffraction analysis. The synthetic approach to these cage polycycles involves high complexity generating processes such as Diels− Alder reaction, [2 + 2] photocycloaddition, and RRM as well as RCM.

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Synthesis of New High-Energy/High-Density Hydrocarbon Fuel Systems

Cited by 4 publications

References 1 publication

Pyrolysis Chemistry of Cubane and Methylcubane: The Effect of Methyl Substitution on Stability and Product Branching

Pyrolysis Chemistry of Cubane and Methylcubane: The Effect of Methyl Substitution on Stability and Product Branching

Ignition Delay for Jet Propellant 10/Air and Jet Propellant 10/High-Energy Density Fuel/Air Mixtures

Synthetic Approach toward Diverse Oxa-Cages via Olefin Metathesis

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