Hydrogenated intramolecular cyclization of diphenylmethane derivatives for synthesizing high-density biofuel

Nie, Genkuo; Zhang, Xiangwen; Pan, Lun; Han, Peijuan; Xie, Junjian; Li, Zheng; Xie, Jiawei; Zou, Ji‐Jun

doi:10.1016/j.ces.2017.07.034

Cited by 45 publications

(32 citation statements)

References 42 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Given the positively linear correlation between the volumetric NHOC and fuel density, many studies attempted to synthesize high-density fuels to increase the volumetric NHOC and expand the flight distance [32,35,36,69,74,75]. A crucial step toward high-density fuels is the synthesis of RJ-4 (39.0 MJ/L) with a density of 0.940 g/ cm 3 [34].…”

Section: Volumetric Nhoc Correlation Between Volumetric Nhoc and Densitymentioning

confidence: 99%

Review on the Relationship Between Liquid Aerospace Fuel Composition and Their Physicochemical Properties

Wang

Jia

Pan

et al. 2020

Trans. Tianjin Univ.

Self Cite

View full text Add to dashboard Cite

The development of advanced air transportation has raised new demands for high-performance liquid hydrocarbon fuels. However, the measurement of fuel properties is time-consuming, cost-intensive, and limited to the operating conditions. The physicochemical properties of aerospace fuels are directly influenced by chemical composition. Thus, a thorough investigation should be conducted on the inherent relationship between fuel properties and composition for the design and synthesis of high-grade fuels and the prediction of fuel properties in the future. This work summarized the effects of fuel composition and hydrocarbon molecular structure on the fuel physicochemical properties, including density, net heat of combustion (NHOC), low-temperature fluidity (viscosity and freezing point), flash point, and thermal-oxidative stability. Several correlations and predictions of fuel properties from chemical composition were reviewed. Additionally, we correlated the fuel properties with hydrogen/carbon molar ratios (nH/C) and molecular weight (M). The results from the least-square method implicate that the coupling of H/C molar ratio and M is suitable for the estimation of density, NHOC, viscosity and effectiveness for the design, manufacture, and evaluation of aviation hydrocarbon fuels.

show abstract

Section: Volumetric Nhoc Correlation Between Volumetric Nhoc and Densitymentioning

confidence: 99%

Review on the Relationship Between Liquid Aerospace Fuel Composition and Their Physicochemical Properties

Wang

Jia

Pan

et al. 2020

Trans. Tianjin Univ.

Self Cite

View full text Add to dashboard Cite

show abstract

“…To gain a better understanding of the intramolecular cyclization to perhydrofluorene, Zou and co‐workers [312] studied 2‐benzylphenol as a model compound. The authors determined that 27 was the hydrodeoxygenation product derived from 2‐benzylphenol, while perhydrofluorene ( 28 ) was the result of intramolecular cyclization (Scheme 36).…”

Section: Lignin‐derived Phenolsmentioning

confidence: 99%

Bio‐Based Cycloalkanes: The Missing Link to High‐Performance Sustainable Jet Fuels

Muldoon

Harvey

2020

ChemSusChem

View full text Add to dashboard Cite

David Glueck, with an emphasis on the synthesis of P-stereogenic phosphine ligands for asymmetric catalysis. He is currently a National Research Council (NRC) postdoctoral fellow with Dr. Benjamin Harvey at the Naval Air Warfare Center Weapons Division (NAWCWD) in China Lake, CA, USA. His research interests include the synthesis of small molecules with applications in fuels, materials, and catalysis. Benjamin G. Harvey received his Ph.D. in inorganic chemistry from the University of Utah, USA, in 2005, studying with Professor Richard D. Ernst. He is now a Senior Research Chemist at the Naval Air Warfare Center, Weapons Division located in China Lake, CA. His current research focuses on the utilization of bio-based substrates for the preparation of advanced materials and the development of hybrid synthetic routes that combine chemical catalysis with synthetic biology. Specific interests include advanced alternative fuels for jet, missile, and rocket propulsion, bio-based high-temperature thermosetting resins, biocomposites, lubricants, and green solvents.

show abstract

“…Due to growing interest in the development of high‐performance bio‐based jet fuels that can out‐perform conventional jet fuels, while reducing net CO 2 emissions, a number of new technologies for the conversion of biomass feedstocks to sustainable cycloalkane fuels have been explored [24–36] . These studies have even extended to high‐density, bicyclic compounds with applications as missile fuels.…”

Section: Introductionmentioning

confidence: 99%

“…[17] Due to growing interest in the development of highperformance bio-based jet fuels that can out-perform conventional jet fuels, while reducing net CO 2 emissions, a number of new technologies for the conversion of biomass feedstocks to sustainable cycloalkane fuels have been explored. [24][25][26][27][28][29][30][31][32][33][34][35][36] These studies have even extended to high-density, bicyclic compounds with applications as missile fuels. For example, our group demonstrated the conversion of the acyclic terpenoid linalool to dimethyltetrahydrodicyclopentadiene (RJ-4) in 2011.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Bio‐Based Methylcyclopentadiene from 2,5‐Hexanedione: A Sustainable Route to High Energy Density Jet Fuels

Woodroffe

Harvey

2020

ChemSusChem

View full text Add to dashboard Cite

The sustainable, bio-based, platform chemical, 2,5-hexanedione [HD (1)], was efficiently converted to methylcyclopentadiene [MCPD (4)] through a three-step process consisting of intramolecular aldol condensation, catalytic chemoselective hydrogenation, and dehydration. Base-catalyzed aldol condensation of 1 resulted in the formation of 3-methyl-2-cyclopenten-1-one [MCO (2)], which was then converted to 3-methyl-2-cyclopenten-1-ol [MCP (3)] by chemoselective reduction with a ternary Ru catalyst system [RuCl 2 (PPh 3) 3 /NH 2 (CH 2) 2 NH 2 /KOH]. The hydrogenation proceeded with 96 % chemoselectivity. 3 was then dehydrated over AlPO 4 /MgSO 4 at 70°C under reduced pressure to yield 4, which can undergo an ambient temperature [4 + 2]-Diels-Alder cyclization to generate dimethyldicyclopentadiene (DMDCPD), a commodity chemical useful for the preparation of high-performance fuels and polymers. Through this approach, advanced jet fuels and materials can be conveniently produced from sustainable cellulosic feedstocks.

show abstract

Hydrogenated intramolecular cyclization of diphenylmethane derivatives for synthesizing high-density biofuel

Cited by 45 publications

References 42 publications

Review on the Relationship Between Liquid Aerospace Fuel Composition and Their Physicochemical Properties

Review on the Relationship Between Liquid Aerospace Fuel Composition and Their Physicochemical Properties

Bio‐Based Cycloalkanes: The Missing Link to High‐Performance Sustainable Jet Fuels

Synthesis of Bio‐Based Methylcyclopentadiene from 2,5‐Hexanedione: A Sustainable Route to High Energy Density Jet Fuels

Contact Info

Product

Resources

About