Renewable High-Density Fuel Synthesis via Cyclooctatetraene Dimerization

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Solution Overview

Problem

Current fuels for volume-limited aircraft, such as JP-10, have limitations in energy density and sustainability, as they are not derived from renewable sources and do not provide sufficient tactical advantages or reduce carbon footprints.

Innovation Solution

A process converting renewable alcohols into high energy density fuels by sequentially converting butadiene to 1,5-cyclooctadiene, then to cyclooctatetraene, and finally to hydrogenated cyclooctatetraene dimers, which are dimerized and purified to achieve fuels with densities up to 1.14 g/mL and net heats of combustion of 175,000 Btu/gal, using catalysts like Mn, Ni, and Pd, and hydrogenation under controlled conditions.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Use of energy by moving object

If conventional fuels like JP-10 are used for volume-limited aircraft, then current propulsion requirements are met, but energy density is limited and carbon footprint is high

Engineering Contradiction:
Improveenergy densityVSAvoidcarbon footprint
Core Design Contradiction:
Use of energy by moving objectVSObject-generated harmful factors

Solution Approach 1:

The patent changes the chemical composition parameters by synthesizing fuels with specific molecular structures (cyclooctatetraene dimers, adamantane derivatives, norbornadiene dimers) that achieve density >1.0 g/mL and net heat of combustion >140,000 Btu/gal, representing a 20% improvement over conventional JP-10 fuel

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates composite fuel formulations by combining multiple synthesized hydrocarbon components (cyclooctatetraene dimers, adamantane derivatives, norbornadiene dimers) with complementary properties to achieve optimal energy density and combustion characteristics while maintaining sustainability

Inventive Principle:
Principle #40Composite materials

2Ease of manufacture

If renewable alcohol feedstocks are converted to traditional jet fuels via dehydration and oligomerization, then sustainable fuel is produced, but fuel density remains modest at 0.75-0.77 g/mL

Engineering Contradiction:
ImprovesustainabilityVSAvoidfuel density
Core Design Contradiction:
Ease of manufactureVSQuantity of substance

Solution Approach 1:

The patent transforms the physical parameter of fuel density by synthesizing compact cyclic hydrocarbon structures with high atomic packing efficiency, achieving densities >1.0 g/mL compared to the 0.75-0.77 g/mL of conventional SPKs, while maintaining renewable feedstock conversion

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent introduces localized cyclic structures (cyclooctatetraene, adamantane, norbornadiene) with specific spatial arrangements that maximize density in critical regions of the fuel molecule, creating heterogeneous molecular architectures with optimized local packing

Inventive Principle:
Principle #3Local quality

Applied Scientific Principles

This section explains which scientific principles are used to turn an abstract innovation direction into a practical engineering solution.

Function Achieved in This Case

The resulting fuels offer a 20% higher net heat of combustion than JP-10, providing a tactical advantage and reducing carbon footprint while being generated from sustainable sources, enhancing propulsion efficiency and sustainability.

Implementation Method 1

A process converting renewable alcohols into high energy density fuels by sequentially converting butadiene to 1,5-cyclooctadiene

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 2

finally to hydrogenated cyclooctatetraene dimers, which are dimerized and purified

Methodology Applied
Scientific EffectHydrogenation: Hydrogenation

Data Source

PatentUS9764997B1High density fuels from renewable alcohols
Publication Date: 2017.09.19 THE UNITED STATES OF AMERICA AS REPRESENTED BY THE SECRETARY OF THE NAVY
  • US9764997B1 patent drawing
  • US9764997B1 patent drawing

AI summary

A method for making hydrogenated cyclooctatetraene dimers including cyclo-dimerizing butadiene to form 1,5-cyclooctadiene in the presence of at least one first catalyst, dehydrogenating 1,5-cyclooctadiene to 1,3,5,7-cyclooctatetraene, dimerizing 1,3,5,7-cyclooctatetraene to a C16 multicyclic hydrocarbon cyclooctatetraene dimer, and hydrogenating multicyclic hydrocarbon cyclooctatetraene dimer to form hydrogenated cyclooctatetraene dimers.