IP Library Granted Patent US 12,454,497
Granted Patent B2
US 12,454,497 · App. 18/255,681 · Granted Oct 28, 2025

Fuels and methods of making the same

Inventors: Derek Richard Vardon (Lakewood, CO); Nabila Asem Huq (Boulder, CO); Randy D. Cortright (Boulder, CO); Zia Abdullah (Littleton, CO); Glenn Richard Hafenstine (Wheat Ridge, CO); Xiangchen Huo (Golden, CO); Huong Thi Thanh Nguyen (Arvada, CO)
Assignee: Alliance for Sustainable Energy, LLC
C07C1/22C07C9/15C07C9/16C07C45/41C07C45/68C10L1/04C10L2200/0469C10L2270/04
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 12,454,497
App. No.
18/255,681
Granted
Oct 28, 2025
Kind
B2
Abstract

The present disclosure relates to a method that includes processing, in a hydrodeoxygenation (HDO) reactor, at least one of a VFA-derived ketone and/or a co-processing stream to produce a composition that is at least partially bioderived, as determined by ASTM-D6866.

Claims (24)

1 . A method comprising:

processing, in a hydrodeoxygenation (HDO) reactor, a volatile fatty acid (VFA)-derived ketone stream and a co-processing stream comprising at least one of a lipid, a fat, an oil, a grease, a petroleum feedstock, a plastic decomposition product, or a combination thereof to produce a composition that is at least partially bioderived, wherein:

the VFA-derived ketone stream and the co-processing stream are separate streams prior to processing.

2 . The method of claim 1 , wherein the co-processing stream comprises at least one of a bioderived fat, a bioderived oil, a bioderived grease, or a combination thereof.

3 . The method of claim 1 , wherein the co-processing stream comprises at least one of a plant oil, an animal fat, an extracted microbial lipid, or a combination thereof.

4 . The method of claim 1 , wherein the HDO reactor comprises a retrofitted HDO reactor previously dedicated to process petroleum-based compounds.

5 . The method of claim 1 , wherein a VFA-derived ketone of the VFA-derived ketone stream has between 9 and 18 carbon atoms.

6 . The method of claim 1 , wherein the composition comprises a paraffin having between 9 and 18 carbon atoms.

7 . The method of claim 1 , wherein the composition comprises n-undecane.

8 . The method of claim 1 , wherein the VFA-derived ketone stream and the co-processing stream are mixed before processing in the HDO reactor.

9 . The method of claim 1 , wherein each of the VFA-derived ketone stream and the co-processing stream are directed in separate streams to the HDO reactor.

10 . The method of claim 1 , further comprising, after the processing, blending at least a portion of the composition with at least one of a fuel, a fuel blendstock, or a combination thereof.

11 . The method of claim 10 , wherein the fuel, the fuel blendstock, or the combination thereof comprises at least one of a diesel fuel, a jet fuel, a gasoline fuel, a marine fuel, or a heavy fuel oil.

12 . The method of claim 1 , wherein the HDO reactor is operated at a temperature between about 200° C. and about 450° C.

13 . The method of claim 1 , wherein the HDO reactor is operated at a pressure between about 500 psig and about 1800 psig.

14 . The method of claim 1 , wherein the HDO reactor is a packed-bed reactor.

15 . The method of claim 1 , wherein at least one of the VFA-derived ketone stream, the co-processing stream, or a combination thereof is directed to the HDO reactor resulting in a weight hourly space velocity between about 0.1 h −1 and about 2 h −1 in the reactor.

16 . A composition comprising:

n-undecane, 5-ethyl-4-propyl-nonane, trimethylcyclohexane, and n-nonane; and

a flash point between about 36° C. and about 85° C.

17 . The composition of claim 16 , further comprising a boiling point between about 180° C. and about 300° C.

18 . The composition of claim 17 , further comprising a melting point between about −100° C. and about 0° C.

19 . The composition of claim 18 , further comprising a kinematic viscosity between about 1.00 mm 2 /s @20° C. and about 2.00 mm 2 /s @20° C.

20 . The composition of claim 19 , further comprising a cetane value between about 40 and about 100.

Assignments (3)
CHANGE OF NAME Recorded Dec 16, 2025
From: ALLIANCE FOR SUSTAINABLE ENERGY, LLC
To: ALLIANCE FOR ENERGY INNOVATION, LLC
Reel/Frame 073993/0276 →
CONFIRMATORY LICENSE Recorded Aug 14, 2023
From: NATIONAL RENEWABLE ENERGY LABORATORY
To: UNITED STATES DEPARTMENT OF ENERGY
Reel/Frame 064577/0962 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 28, 2023
From: VARDON, DEREK RICHARD; HUQ, NABILA ASEM; CORTRIGHT, RANDY D.; ABDULLAH, ZIA; HAFENSTINE, GLENN RICHARD; HUO, XIANGCHEN; NGUYEN, HUONG THI THANH
To: ALLIANCE FOR SUSTAINABLE ENERGY, LLC
Reel/Frame 064093/0811 →
Continuity (5)
Continuation 17121336 · Dec 14, 2020
Provisional Application 63163465 · Mar 19, 2021
Provisional Application 63121813 · Dec 4, 2020
Provisional Application 63033331 · Jun 2, 2020
Related Publication 20240368054A1 · Nov 7, 2024
References Cited (59)
US 6124509A · Voges et al. · 2000 [cited by applicant]
US 9828354B2 · Chen et al. · 2017 [cited by applicant]
US 11420912B2 · Vardon et al. · 2022 [cited by applicant]
US 20070135316A1 · Koivusalmi et al. · 2007 [cited by applicant]
US 20110150813A1 · Desenne et al. · 2011 [cited by applicant]
US 20120198760A1 · Blommel et al. · 2012 [cited by applicant]
US 20130017590A1 · Chung · 2013 [cited by examiner]
US 20140073826A1 · Miller et al. · 2014 [cited by applicant]
US 20140114101A1 · Greene et al. · 2014 [cited by applicant]
US 20140335586A1 · Zhang · 2014 [cited by examiner]
US 20150018588A1 · Myllyoja · 2015 [cited by examiner]
US 20150087872A1 · Miller · 2015 [cited by examiner]
US 20160152907A1 · Baer · 2016 [cited by examiner]
US 20170080672A1 · Amano · 2017 [cited by applicant]
US 20180086677A1 · Myllyoja et al. · 2018 [cited by applicant]
US 20190185759A1 · Kanervo · 2019 [cited by examiner]
US 20190218466A1 · Slade et al. · 2019 [cited by applicant]
US 20200181504A1 · Myllyoja · 2020 [cited by examiner]
US 20220041939A1 · Tiitta · 2022 [cited by examiner]
US 20230096222A1 · Leminen · 2023 [cited by examiner]
WO 2006084285A2 · 2006 [cited by applicant]
WO 2008152200A1 · 2008 [cited by applicant]
WO 2011115394A2 · 2011 [cited by applicant]
WO 2015148412A2 · 2015 [cited by applicant]
WO 2018001694A1 · 2018 [cited by applicant]
International Search Report and Written Opinion for International (PCT) Application No. PCT/US21/61938, mailed Mar. 16, 2022, pp. 1-8. [cited by applicant]
Alonso et al., “Production of liquid hydrocarbon transportation fuels by oligomerization of biomass-derived C9 alkenes,” RSC Green Chemistry, vol. 12, 2010, 8 pages. [cited by applicant]
Amer et al., “Low carbon strategies for sustainable bio-alkane gas production and renewable energy,” RSC Energy & Environmental Science, vol. 13, 2020, 14 pages. [cited by applicant]
Atasoy et al., “Bio-based volatile fatty acid production and recovery from waste streams: Current status and future challenges,” Elsevier Bioresource Technology, vol. 268, 2018, 14 pages. [cited by applicant]
Badgett et al., “Economic analysis of wet waste-to-energy resources in the United States,” Elsevier Energy, vol. 176, 2019, 11 pages. [cited by applicant]
Balakrishnan et al., “Novel pathways for fuels and lubricants from biomass optimized using life-cycle greenhouse gas assessment,” PNAS, vol. 112, No. 25, Jun. 23, 2015, 6 pages. [cited by applicant]
Bhatt et al., “Value Proposition of Untapped Wet Wastes: Carboxylic Acid Production through Anaerobic Digestion,” iScience, vol. 23, Jun. 26, 2020, 29 pages. [cited by applicant]
Ciesielski et al., “Advances in Multiscale Modeling of Lignocellulosic Biomass,” ACS Sustainable Chemistry & Engineering, vol. 8, 2020, 20 pages. [cited by applicant]
Dahiya et al., “Chapter 31—Cutting-edge biofuel conversion technologies to integrate into petroleum-based infrastructure and integrated biorefineries”, Bioenergy (Second Edition), 2020, pp. 649-670. [cited by applicant]
Davis et al., “Process Design and Economics for the Conversion of Lignocellulosic Biomass to Hydrocarbon Fuels and Coproducts: 2018 Biochemical Design Case Update,” NREL Technical Report NREL/TP-5100-71949; Nov. 2018; 1… [cited by applicant]
Fufachev et al., “Tandem catalytic aromatization of volatile fatty acids,” RSC Green Chemistry, vol. 22, 2020, 10 pages. [cited by applicant]
Gaertner, “Ketonization Reactions of Carboxylic Acids and Esters over Ceria-Zirconia as Biomass-Upgrading Processes,” ACS, Ind. Eng. Chem. Res. vol. 49, No. 13, 2010, 7 pages. [cited by applicant]
Glinski et al., “Catalytic Ketonization of Carboxylic Acids Synthesis of Saturated and Unsaturated Ketones,” React. Kinet. Catal. Lett., vol. 69, No. 1, 2000, 6 pages. [cited by applicant]
Hafenstine et al., “Single-phase catalysis for reductive etherification of diesel bioblendstocks,” RSC Green Chemistry, vol. 22, 2020, 10 pages. [cited by applicant]
Han et al., “Co-hydrotreatment of the Bio-oil Lignin-Rich Fraction and Vegetable Oil”, Energy Fuels, 2020, vol. 34, No. 1, pp. 516-529. [cited by applicant]
Harvey et al., “1-Hexene: a renewable C6 platform for full-performance jet and diesel fuels,” RSC Green Chemistry, vol. 16, 2014, 7 pages. [cited by applicant]
Holtzapple et al., “Biomass Conversion to Mixed Alcohol Fuels Using the MixAlco Process,” Applied Biochemistry and Biotechnology, vol. 77-79, 1999, 23 pages. [cited by applicant]
Huo et al., “Tailoring diesel bioblendstock from integrated catalytic upgrading of carboxylic acids: a “fuel property first” approach,” RSC Green Chemistry, vol. 21, 2019, 5 pages. [cited by applicant]
Huq et al., “Performance-advantaged ether diesel bioblendstock production by a priori design,” PNAS, vol. 116, No. 52, Dec. 26, 2019, 10 pages. [cited by applicant]
Jahromi et al., “Hydrodeoxygenation of Aqueous-Phase Catalytic Pyrolysis Oil to Liquid Hydrocarbons Using Multifunctional Nickel Catalyst,” Ind. Eng. Chem. Res., vol. 57, 2018, 12 pages. [cited by applicant]
Jiang et al., “Ce/MgAl mixed oxides derived from hydrotalcite LDH precursors as highly efficient catalysts for ketonization of carboxylic acid,” RSC Catalysis Science & Technology, DOI: 10.1039/c9cy01323g, 2019, 10 page… [cited by applicant]
Milbrandt et al., “Wet waste-to-energy resources in the United States,” Elsevier Resources, Conservation Recycling, vol. 137, 2018, 16 pages. [cited by applicant]
Pham et al., “Ketonization of Carboxylic Acids: Mechanisms, Catalysts, and Implications for Biomass Conversion,” ACS Catalysis, vol. 3, 2013, 18 pages. [cited by applicant]
Pham et al., “Reaction kinetics and mechanism of ketonization of aliphatic carboxylic acids with different carbon chain lengths over Ru/TiO2 catalyst,” Elsevier Journal of Catalysis, vol. 314, 2014, 10 pages. [cited by applicant]
Pacchioni, “Ketonization of Carboxylic Acids in Biomass Conversion over TiO2 and ZrO2 Surfaces: A DFT Perspective,” ACS Catalysis, vol. 4, 2014, 15 pages. [cited by applicant]
Phung et al., “Catalytic pyrolysis of vegetable oils to biofuels: Catalyst functionalities and the role of ketonization on the oxygenate paths,” Elsevier Fuel Processing Technology, vol. 140, 2015, 6 pages. [cited by applicant]
Rabaev et al., “Improvement of hydrothermal stability of Pt/SAPO-11 catalyst in hydrodeoxygenation-isomerization-aromatization of vegetable oil,” Elsevier Journal of Catalysis, vol. 332, 2015, 13 pages. [cited by applicant]
Ramos et al., “Towards understanding the hydrodeoxygenation pathways of furfural-acetone aldol condensation products over supported Pt catalysts,” RSC Catalysis Science & Technology, vol. 6, 2016, 13 pages. [cited by applicant]
Sacia et al., “Highly Selective Condensation of Biomass-Derived Methyl Ketones as a Source of Aviation Fuel,” ChemSusChem, vol. 8, 2015, 11 pages. [cited by applicant]
Shylesh et al., “Integrated catalytic sequences for catalytic upgrading of bio-derived carboxylic acids to fuels, lubricants and chemical feedstocks,” RSC Sustainable Energy & Fuels, vol. 1, 2017, 5 pages. [cited by applicant]
Shylesh et al., “Experimental and Computational Studies of Carbon-Carbon Bond Formation via Ketonization and Aldol Condensation over Site-Isolated Zirconium Catalysts,” ACS Catalysis, vol. 10, 2020, 14 pages. [cited by applicant]
Takanabe et al., “Catalyst deactivation during steam reforming of acetic acid over Pt/ZrO2,” Elsevier Chemical Engineering Journal, vol. 120, 2006, 5 pages. [cited by applicant]
Van Dyk et al., “Potential synergies of drop-in biofuel production with further co-processing at oil refineries”, Biofuels, Bioproducts & Biorefining, 2019, vol. 13, No. 3, pp. 760-775. [cited by applicant]
Yang et al., “Hydrodeoxygenation (HDO) of Biomass Derived Ketones Using Supported Transition Metals in a Continuous Reactor,” ACS Sustainable Chemistry & Engineering, vol. 7, 2019, 10 pages. [cited by applicant]