IP Library Granted Patent US 12,590,113
Granted Patent B2
US 12,590,113 · App. 17/842,062 · Granted Mar 31, 2026

Continuous processing of lignin for reduced solvent usage in reductive catalytic fractionation

Inventors: Jacob S. Kruger (Arvada, CO); Gregg Tyler Beckham (Golden, CO); David Gregory Brandner (Golden, CO); Andrew Wolf Bartling (Golden, CO); Yuriy Román (Cambridge, MA); Jun Hee Jang (Lakewood, CO); Nicholas Earl Thornburg (Denver, CO); Gregory George Facas (Moorestown, NJ)
Assignees: Alliance for Energy Innovation, LLC; Massachusetts Institute of Technology
C07G1/00B01J8/0278B01J21/18B01J23/755
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 12,590,113
App. No.
17/842,062
Granted
Mar 31, 2026
Kind
B2
Abstract

Described herein are devices and methods for the efficient and economic generation of lignin monomers from biomass. The provided devices and methods utilize reductive catalytic fractionation with an organic solvent to extract high-quality lignin from biomass and cleave specific lignin bonds to generate valuable lignin monomers with a relatively narrow product slate. Advantageously, the devices and methods described herein utilize solvent recycling, multiple solvolysis chambers with multiple biomass beds and/or physical agitation (e.g., use of a screw extruder) to reduce the amount of solvent required and increase economic efficiency and monomer yield.

Claims (17)

1 . A method comprising:

treating biomass with a solvent in at least one solvolysis chamber, thereby extracting lignin and generating a solvolysis liquor;

reacting the solvolysis liquor in the presence of a catalyst, thereby generating at least one lignin monomer;

flowing the solvolysis liquor from the solvolysis chamber and recycling the solvolysis liquor back to the solvolysis chamber, thereby increasing the concentration of lignin in the solvolysis liquor.

2 . The method of claim 1 , wherein the step of treating biomass occurs in a plurality of solvolysis chambers, and

wherein each of the solvolysis chambers comprises a biomass bed.

3 . The method of claim 2 , wherein the plurality of solvolysis chambers are arranged in parallel.

4 . The method of claim 2 , wherein each of the plurality of solvolysis chambers comprises a screw extruder.

5 . The method of claim 1 , wherein the step of treating biomass is performed in the presence of a screw extruder.

6 . The method of claim 1 further comprising a step of storing the solvolysis liquor prior to reacting the solvolysis liquor in the presence of a catalyst.

7 . The method of claim 6 , wherein the step of storing the solvolysis liquor comprises storing the solvolysis liquor for a time period greater than or equal to 1 day.

8 . The method of claim 6 , wherein the step of storing the solvolysis liquor further comprises analyzing the solvolysis liquor.

9 . The method of claim 1 , wherein the solvent comprises an alcohol.

10 . The method of claim 1 , wherein the solvent is methanol.

11 . The method of claim 1 , wherein the catalyst comprises Ni/C.

12 . The method of claim 1 , wherein the step of treating the biomass comprises providing a solvent at a ratio less than or equal to 4:1 wt % solvent to biomass.

13 . The method of claim 1 , wherein the method yields greater than or equal to 15 wt % lignin monomers with respect to lignin weight.

Assignments (5)
CHANGE OF NAME Recorded Dec 16, 2025
From: ALLIANCE FOR SUSTAINABLE ENERGY, LLC
To: ALLIANCE FOR ENERGY INNOVATION, LLC
Reel/Frame 073993/0276 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 9, 2024
From: ROMÁN, YURIY
To: MASSACHUSETTS INSTITUTE OF TECHNOLOGY
Reel/Frame 069545/0805 →
CONFIRMATORY LICENSE Recorded Sep 2, 2022
From: NATIONAL RENEWABLE ENERGY LABORATORY
To: UNITED STATES DEPARTMENT OF ENERGY
Reel/Frame 060983/0817 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 25, 2022
From: THORNBURG, NICHOLAS EARL; FACAS, GREGORY GEORGE
To: ALLIANCE FOR SUSTAINABLE ENERGY, LLC
Reel/Frame 060608/0637 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 7, 2022
From: KRUGER, JACOB S.; BECKHAM, GREGG TYLER; BRANDNER, DAVID GREGORY; BARTLING, ANDREW WOLF; JANG, JUN HEE
To: ALLIANCE FOR SUSTAINABLE ENERGY, LLC
Reel/Frame 060432/0397 →
Continuity (2)
Provisional Application 63211238 · Jun 16, 2021
Related Publication 20220411454A1 · Dec 29, 2022
References Cited (29)
JP 2004083482A · 2004 [cited by examiner]
WO WO2019108959A1 · 2019 [cited by examiner]
WO WO2020002361A1 · 2020 [cited by examiner]
Yamada et al., JP 2004-083482 A machine translation in English, Mar. 18, 2004. (Year: 2004). [cited by examiner]
Abu-Omar et al., “Guidelines for performing lignin-first biorefining”, Energy & Environmental Science, 2021, vol. 14, pp. 262-292. [cited by applicant]
Anderson et al., “Flowthrough Reductive Catalytic Fractionation of Biomass”, Joule, Nov. 2017, vol. 1, No. 3, pp. 613-622. [cited by applicant]
Anderson et al., “Kinetic Studies of Lignin Solvolysis and Reduction by Reductive Catalytic Fractionation Decoupled in Flow-Through Reactors”, ACS Sustainable Chemistry & Engineering, 2018, vol. 6, pp. 7951-7959. [cited by applicant]
Bartling et al., “Techno-economic analysis and life cycle assessment of a biorefinery utilizing reductive catalytic fractionation”, Energy & Environmental Science, 2008, vol. 14, No. 8, pp. 4147-4168. [cited by applicant]
Brandner et al., “Flow-through solvolysis enables production of native-like lignin from biomass”, Green Chemistry, 2021, vol. 23, No. 15, pp. 5437-5441. [cited by applicant]
Cooreman et al., “Perspective on Overcoming Scale-Up Hurdles for the Reductive Catalytic Fractionation of Lignocellulose Biomass”, Industrial Research & Engineering Chemistry Research, 2020, vol. 59, No. 39, pp. 17035-1… [cited by applicant]
Corona et al., “Life cycle assessment of adipic acid production from lignin”, Green Chemistry, 2018, vol. 20, pp. 3857-3866. [cited by applicant]
Davis et al., “Process Design and Economics for the Conversion of Lignocellulosic Biomass to Hydrocarbons: Dilute-Acid Prehydrolysis and Enzymatic Hydrolysis Deconstruction of Biomass to Sugars and Biological Conversion… [cited by applicant]
Huang et al., “Reductive fractionation of woody biomass into lignin monomers and cellulose by tandem metal triflate and Pd/C catalysis”, Green Chemistry, 2017, vol. 19, No. 1, pp. 175-187. [cited by applicant]
Kumaniaev et al., “Lignin depolymerization to monophenolic compounds in a flow-through system”, Green Chemistry, 2017, vol. 19, No. 24, pp. 5767-5771. [cited by applicant]
Lan et al., “Continuous hydrogenolysis of acetal-stabilized lignin in flow”, Green Chemistry, 2021, vol. 23, No. 1, pp. 320-327. [cited by applicant]
Liao et al., “A sustainable wood biorefinery for low-carbon footprint chemicals production”, Science, Feb. 2020, vol. 367, No. 6484, pp. 1385-1390. [cited by applicant]
Mansfield et al., “Whole plant cell wall characterization using solution-state 2D NMR”, Nature Protocols, 2012, vol. 7, No. 9, pp. 1579-1589. [cited by applicant]
Muurinen, “Organosolv Pulping: A review and distillation study related to peroxyacid pulping”, Academic Dissertation to be presented with the assent of the Faculty of Technology, University of Oulu, May 2000, pp. 1-314. [cited by applicant]
Ouyang et al., “Coupling organosolv fractionation and reductive depolymerization of woody biomass in a two-step catalytic process”, Green Chemistry, 2018, vol. 20, No. 10, pp. 2308-2319. [cited by applicant]
Van Den Bosch et al., “Reductive lignocellulose fractionation into soluble lignin-derived phenolic monomers and dimers and processable carbohydrate pulps”, Energy & Environmental Science, 2015, vol. 8, pp. 1748-1763. [cited by applicant]
Van Den Bosch et al., “Integrating lignin valorization and bio-ethanol production: on the role of Ni—Al2O3 catalyst pellets during lignin-first fractionation”, Green Chemistry, 2017, vol. 19, pages pp. 3313-3326. [cited by applicant]
Questell-Santiago et al., “Stabilization strategies in biomass depolymerization using chemical functionalization”, Nature Reviews Chemistry, Jun. 2020, vol. 4, pp. 311-330. [cited by applicant]
Rinaldi et al., “Paving the Way for Lignin Valorisation: Recent Advances in Bioengineering, Biorefining and Catalysis”, Angewandte Chemie—International Edition, Jul. 2016, vol. 55, No. 29, pp. 8164-8215. [cited by applicant]
Schutyser et al., “Chemicals from lignin: an interplay of lignocellulose fractionation, depolymerisation, and upgrading”, Chemical Society Reviews, 2018, vol. 47, No. 3, pp. 852-908. [cited by applicant]
Shuai et al., “Formaldehyde stabilization facilitates lignin monomer production during biomass depolymerization”, Science, Oct. 2016, vol. 354, No. 6310, pp. 329-333. [cited by applicant]
Tschulkow et al., “Integrated techno-economic assessment of a biorefinery process: The high-end valorization of the lignocellulosic fraction in wood streams”, Journal of Cleaner Production, Sep. 2020, vol. 266, pp. 1-11. [cited by applicant]
Yan et al., “Selective degradation of wood lignin over noble-metal catalysts in a two-step process”, ChemSusChem, 2008, vol. 1, No. 7, pp. 626-629. [cited by applicant]
Zijlstra et al., “Efficient Mild Organosolv Lignin Extraction in a Flow-Through Setup Yielding Lignin with High β-O-4 Content”, Polymers, 2019, vol. 11, No. 1913, pp. 1-17. [cited by applicant]
Zhou et al., “Rapid flow-through fractionation of biomass to preserve labile aryl ether bonds in native lignin”, Green Chemistry, 2019, vol. 21, pp. 4625-4632. [cited by applicant]