# US 11,306,039 B1 · System and method for making fuels

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- Number: US 11,306,039 B1
- Document ID: US11306039B1
- Status: Granted
- Kind: B1
- Application number: 16/431,372
- Filed: 2019-06-04
- Granted: 2022-04-19
- Earliest claimed: 2018-06-05
- Assignees: Triad National Security, LLC
- Applicants: Triad National Security, LLC
- Inventors: Andrew D. Sutton; Cameron M. Moore; Orion Staples; Troy A. Semelsberger; William L. Kubic, Jr.
- Web page: https://patentgrep.com/patent/US11306039B1

## CPC

- C07C 1/24: by elimination of water
- C10G 3/49: {containing crystalline aluminosilicates, e.g. molecular sieves}
- B01D 3/143: {by two or more of a fractionation, separation or rectification step}
- B01J 19/0013: {Controlling the temperature of the process}
- B01J 19/245: {placed in series}
- B01J 21/04: Alumina
- B01J 21/12: Silica and alumina
- B01J 21/18: Carbon
- B01J 23/462: {Ruthenium}
- B01J 23/72: Copper
- B01J 23/755: Nickel
- B01J 23/892: {Nickel and noble metals}
- C07C 2/08: Catalytic processes
- C07C 5/32: by dehydrogenation with formation of free hydrogen
- C07C 29/103: {of cyclic ethers}
- C07C 29/141: with hydrogen or hydrogen-containing gases
- C07C 29/145: with hydrogen or hydrogen-containing gases
- C07C 45/59: in five-membered rings (from ozonides C07C45/40)
- C10G 3/48: {further characterised by the catalyst support}
- C10G 9/00: Thermal non-catalytic cracking, in the absence of hydrogen, of hydrocarbon oils
- C10G 50/00: Production of liquid hydrocarbon mixtures from lower carbon number hydrocarbons, e.g. by oligomerisation
- C10G 57/02: with polymerisation
- C10L 1/02: essentially based on components consisting of carbon, hydrogen, and oxygen only
- B01J 23/40: of the platinum group metals
- B01J 23/70: of the iron group metals or copper
- B01J 23/89: combined with noble metals
- B01J 29/068: Noble metals
- B01J 29/072: Iron group metals or copper
- B01J 2219/00033: Continuous processes
- B01J 2219/00157: by means of a burner
- C07C 2529/40: of the pentasil type, e.g. types ZSM-5, ZSM-8 or ZSM-11
- C07C 2601/08: the ring being saturated
- C07C 2601/10: the ring being unsaturated
- Y02P 30/20: using bio-feedstock
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C10G: CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION (cracking to hydrogen or synthesis gas C01B; cracking or pyrolysis of hydrocarbon gases to individual hydrocarbons or mixtures thereof of definite or specified constitution C07C; cracking to cokes C10B); RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- B01D: SEPARATION (separating solids from solids by wet methods B03B, B03D; by pneumatic jigs or tables B03B; by other dry methods B07; magnetic or electrostatic separation of solid materials from solid materials or fluids, separation by high-voltage electric fields B03C; centrifuges, vortex apparatus B04; presses per se for squeezing-out liquid from liquid-containing material B30B9/02; treatment of water C02F, e.g. softening by ion-exchange C02F1/42; {arrangements of air intake cleaners in gas turbine plants F02C7/05} ; arrangements or mounting of filters in air-conditioning, air-humidification or ventilation F24F13/28)
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- C10L: FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

## Abstract

Embodiments of a system and method are disclosed for obtaining high-energy fuels. In some embodiments, the system and method produces one or more fused cyclic compounds that can include one or more bridging points. The fused cyclic compounds are suitable for use as a high-energy fuels, and may be derived from biomass.

## Claims

### Claim 1

A method, comprising:
hydrogenating a carbonyl-containing precursor compound having a Formula I with a catalyst system and hydrogen gas to produce a mixture comprising an alcohol-containing compound having a Formula II; and
converting the alcohol-containing compound to a diene-containing compound by dehydrating the alcohol-containing compound with a dehydrating agent to produce an alkene-containing compound and then pyrolyzing the alkene-containing compound to a diene-containing compound; wherein
Formula I is
wherein R is an oxygen-containing heteroaryl compound and R1 is hydrogen or alkyl; and
Formula II is
wherein R2 and R3 join together to provide an aliphatic ring.

### Claim 2 (depends on 1)

The method of claim 1, wherein the carbonyl-containing precursor compound is derived from biomass.

### Claim 3 (depends on 1)

The method of claim 1, wherein the carbonyl-containing precursor compound is furfural.

### Claim 4 (depends on 1)

The method of claim 1, wherein the catalyst system comprises (i) a metal selected from Ni, Co, Cu, Fe, Ru, Pd, Pt, or any combination thereof; and (ii) a catalytic support selected from an activated carbon, a zeolite, an oxide, or any combinations thereof.

### Claim 5 (depends on 1)

The method of claim 1, wherein the mixture comprising the alcohol-containing compound further comprises a ketone, and the method further comprises hydrogenating the ketone to produce a further amount of the alcohol-containing compound.

### Claim 6 (depends on 1)

The method of claim 1, further comprising dimerizing the diene-containing compound to provide at least one fused cyclic compound comprising a bridged bicyclic skeleton.

### Claim 7

A method, comprising;
hydrogenating a carbonyl-containing precursor compound having a Formula I with a catalyst system and hydrogen gas to produce a mixture comprising an alcohol-containing compound having a Formula II; and
converting the alcohol-containing compound to at least one fused cyclic compound comprising a bridged bicyclic skeleton by (i) dehydrating the alcohol-containing compound with a dehydrating agent to produce an alkene-containing compound and then pyrolyzing the alkene-containing compound to a diene-containing compound; and (ii) dimerizing the diene-containing compound to provide the at least one fused cyclic compound; wherein
Formula I is
wherein R is an oxygen-containing heteroaryl compound and R1 is hydrogen or alkyl; and
Formula II is
wherein R2 and R3 join together to provide an aliphatic ring.

### Claim 8 (depends on 7)

The method of claim 7, wherein the carbonyl-containing precursor compound is derived from biomass.

### Claim 9 (depends on 7)

The method of claim 7, wherein the carbonyl-containing precursor compound is furfural.

### Claim 10 (depends on 7)

The method of claim 7, wherein the catalyst system comprises (i) a metal selected from Ni, Co, Cu, Fe, Ru, Pd, Pt, or any combination thereof; and (ii) a catalytic support selected from an activated carbon, a zeolite, an oxide, or any combinations thereof.

### Claim 11 (depends on 7)

The method of claim 7, wherein the mixture comprising the alcohol-containing compound further comprises a ketone, and the method further comprises hydrogenating the ketone to produce a further amount of the alcohol-containing compound.