High-Performance, Biobased, Jet Fuel Blends Containing Hydrogenated Monoterpenes and Synthetic Paraffinic Kerosenes

Woodroffe, Josanne–Dee; Harvey, Benjamin G.

doi:10.1021/acs.energyfuels.0c00274

Cited by 51 publications

(52 citation statements)

References 50 publications

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“…DMCO exhibited a density of 0.827 g mL −1 at 15 °C. This value is 6.7 % higher than the lower limit for conventional jet fuel (0.775 g mL −1 ) and 12.8 % higher than the acyclic hydrogenated isoprene dimer 2,6‐dimethyloctane (0.73 g mL −1 ) [27] . The gravimetric and volumetric NHOCs of DMCO were 43.822 MJ kg −1 and 36.222 MJ L −1 , respectively.…”

Section: Bio‐based Alkenesmentioning

confidence: 75%

“…This value is 6.7 % higher than the lower limit for conventional jet fuel (0.775 g mL À 1 ) and 12.8 % higher than the acyclic hydrogenated isoprene dimer 2,6-dimethyloctane (0.73 g mL À 1 ). [27] The gravimetric and volumetric NHOCs of DMCO were 43.822 MJ kg À 1 and 36.222 MJ L À 1 , respectively. These values are up to 2.4 % and 9 % higher, respectively, than conventional jet fuel (Table 10).…”

Section: Bio-based Alkenesmentioning

confidence: 95%

“…[24][25][26] This result has opened up the development of aromatic-free bio-based fuels with increased gravimetric heats of combustion and improved emission profiles. [27] Bio-based cycloalkanes represent the missing link to the production of full-performance and ultra-performance drop-in synthetic fuels for commercial and military jet aircraft. These fuels can enhance the range of commercial and military aircraft while greatly reducing the impact of jet fuel combustion on the environment.…”

Section: Introductionmentioning

confidence: 99%

“…Recent work has shown that cycloalkanes at concentrations above about 30 vol % in SPKs have swelling characteristics similar to conventional jet fuel [24–26] . This result has opened up the development of aromatic‐free bio‐based fuels with increased gravimetric heats of combustion and improved emission profiles [27] . Bio‐based cycloalkanes represent the missing link to the production of full‐performance and ultra‐performance drop‐in synthetic fuels for commercial and military jet aircraft.…”

Section: Introductionmentioning

confidence: 99%

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

Muldoon

Harvey

2020

ChemSusChem

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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.

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Section: Bio‐based Alkenesmentioning

confidence: 75%

Section: Bio-based Alkenesmentioning

confidence: 95%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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

Muldoon

Harvey

2020

ChemSusChem

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“…In contrast, recent studies have shown that 30 % cycloalkane blends have the same swelling capability as low (8 %) aromatic fuel blends [20–23] . Cycloalkanes also have higher densities due to their constrained geometries, and significantly higher volumetric NHOCs than SPKs and traditional jet fuels [17] …”

Section: Introductionmentioning

confidence: 92%

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

Woodroffe

Harvey

2020

ChemSusChem

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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.

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p‐Menthadienes as Biorenewable Feedstocks for a Monoterpene‐Based Biorefinery

Tibbetts

Bull

2021

Advanced Sustainable Systems

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the upgrading of biomass into biofuels and platform chemicals will need to be developed and integrated into new/existing chemical processes. [2] The large volumes and wide geographical distribution of lignocellulosic biomass means that it will undoubtedly play a key role as a biorenewable feedstock for bulk chemical production. [3] In this approach, fermentative processes are used to depolymerize lignocellulose biomass into sugars (e.g., glucose and fructose), with these monomers then transformed into low-value feedstocks such as bioethanol, succinic acid, glutamic acid, and 5-hydroxymethylfurfural. [4] Although highly promising, technological difficulties associated with large-scale catalytic upgrading of these highly oxygenated biopolymers cause significant problems that still need to be overcome before lignocellulose-based biorefineries become more widely established. [5] Monoterpenes (and monoterpenoids) represent an alternative biomass source for the production of biofuels, polymers, and chemicals that are available in significant volumes at low cost. Significant amounts of commercially available monoterpenes are currently produced as products and waste from the forestry and agricultural industries, all of which can be considered as potentially useful biorenewable feedstocks for fuel and chemical production. These include turpentine (≈360 000 tonnes pa), limonene-containing citrus oil (≈30 000 tonnes pa), mentholcontaining mint oil (≈20 000 tonnes pa), and 1,8-cineole from eucalyptus oil (≈7000 tonnes pa with an estimated multimillion tonne production potential per annum). [6] The structures of these energy-dense, lightly oxygenated, alkene-containing C 10 building blocks more closely resemble those of petroleum-based hydrocarbons, which means they can potentially be catalytically upgraded using existing refining technologies to produce a wide range of chemical products (including aromatics).Crude sulfate turpentine (CST) is the cheapest and most widely available source of monoterpene biomass, with around 260 000 tonnes of CST produced as a waste by-product of the paper industry annually. High pressure cooking of wood chips to produce paper pulp in the Kraft process generates around 15 kg of CST per tonne of pulp, [7] which is comprised of a mixture of monoterpenes and around 5% volatile sulfur compounds (e.g., Me 2 S). [6a] A further annual 100 000 tonnes of pinene-rich gum turpentine (GT) is also produced through sustainable tapping of the trunks of living trees. The major monoterpene components of turpentine are α-pinene, β-pinene, 3-carene, and limonene, along with small amounts of camphene and C 15 A terpene-based biorefinery is described that uses crude sulfate turpentine (CST) and gum turpentine (GT) to produce mixtures of p-menthadienes (p-MeDs) as biorenewable terpene feedstocks. An acid catalyzed ring opening reaction (6 m aq. H 2 SO 4 , 90 °C) is first used to convert the major bicyclic monoterpenes (α-pinene, β-pinene, and 3-carene) in untreated CST (or GT with 5 mol% Me 2 S) into mixtures of ...

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High-Performance, Biobased, Jet Fuel Blends Containing Hydrogenated Monoterpenes and Synthetic Paraffinic Kerosenes

Cited by 51 publications

References 50 publications

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

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

p‐Menthadienes as Biorenewable Feedstocks for a Monoterpene‐Based Biorefinery

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