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High-Performance Jet Fuels Derived from Bio-Based Alkenes by Iron-Catalyzed [2+2] Cycloaddition
David M Morris1, Roxanne L Quintana1, Benjamin G Harvey1
1Chemistry Division, US NAVY, NAWCWD, Research Department, China Lake, California, 93555, USA.
Chemsuschem
|March 26, 2019
Summary
Bio-derived alkenes were converted into high-performance cycloparaffinic fuels using a novel iron-catalyzed [2+2] cycloaddition. This sustainable method yields advanced fuels with superior combustion properties and low viscosity.
Area of Science:
- Catalysis
- Sustainable Chemistry
- Fuel Science
Background:
- Development of sustainable, high-performance fuels is critical for reducing reliance on fossil fuels.
- Cycloparaffinic structures offer enhanced fuel properties like higher energy density and combustion efficiency.
- Efficient catalytic methods are needed to synthesize these advanced fuel molecules from renewable feedstocks.
Purpose of the Study:
- To synthesize high-performance cycloparaffinic fuels via [2+2] cycloaddition of bio-derived alkenes.
- To investigate the catalytic activity and selectivity of a low-valent iron pyridine(diimine) complex.
- To evaluate the fuel properties of the synthesized cycloparaffinic mixtures.
Main Methods:
- Utilized a low-valent iron pyridine(diimine) complex [(Me PDI)Fe(N2)2(μ-N2)] as a catalyst.
- Performed [2+2] cycloaddition reactions with bio-derived alkenes: 1-hexene, isoprene, and 1-pentene.
- Separated and purified fuel mixtures through hydrogenation and fractional distillation.
Main Results:
- Achieved high selectivity (85%) towards 1,2-cyclobutanes with 1-pentene and 1-hexene.
- Synthesized fuel mixtures with high yields (83-93%) and superior properties: high density (0.767-0.783 g/mL) and net heat of combustion (up to 120.6 kBTU/gal).
- Observed extremely low fuel viscosities (2.38-4.78 mm²/s at -20°C) due to cyclobutane and acyclic dimer presence.
Conclusions:
- The iron-catalyzed [2+2] cycloaddition is a viable and efficient route to sustainable, high-performance cycloparaffinic fuels.
- The synthesized fuels exhibit improved combustion characteristics and low-temperature flow properties compared to conventional fuels.
- This catalytic approach offers a promising pathway for producing advanced biofuels from readily available bio-derived alkenes.
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