IP Library Granted Patent US 10,800,891
Granted Patent B1
US 10,800,891 · App. 15/452,487 · Granted Oct 13, 2020

Conversion of lignin into a water-soluble polyacid using a MOF catalyst

Inventors: Michael S. Kent (Albuquerque, NM); Mark D. Allendorf (Pleasanton, CA); Vitalie Stavila (Pleasanton, CA)
Assignee: National Technology & Engineering Solutions of Sandia, LLC
C08H6/00B01J31/1691C08L97/005C09D11/08C09D11/107B01J2231/70
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Quick Facts
Patent No.
US 10,800,891
App. No.
15/452,487
Granted
Oct 13, 2020
Kind
B1
Abstract

A process for valorization of lignin includes the steps of mixing lignin; a MOF catalyst metalated with a metal atom selected from the group consisting of Fe, Mn, Co, Cu, or Ni, and combinations thereof; an oxidizing agent; and an aqueous solvent. The product of this process, a charged polyacid-containing species derived from lignin, may be included in a dispersion with a dispersible particulate material, and an aqueous dispersing medium.

Claims (40)

1. A process for valorization of lignin comprising:

mixing

lignin,

a MOF catalyst metalated with a metal atom selected from the group consisting of Fe, Mn, Co, Cu, or Ni, and combinations thereof;

an oxidizing agent; and

an aqueous solvent;

wherein the pH of the mixture is 2 to 10; and

recovering a product comprising a charged polyacid, wherein the charged polyacid when mixed with an alpha-aluminum oxide powder and water results in a zeta potential of the resulting dispersion of −30 to −80 mV at pH values above 6.

2. The process of claim 1 , wherein the MOF catalyst is a recovered MOF catalyst.

3. The process of claim 1 , wherein the metal atom is Fe.

4. The process of claim 1 , wherein the MOF catalyst comprises a node, the node including a zirconium atom; and the MOF catalyst comprises a linker including a heteroaromatic group, the linker being coupled to the node.

5. The process of claim 1 , wherein the MOF catalyst comprises a bipyridine-containing linker group.

6. The process of claim 1 , wherein the metal atom in the MOF catalyst reacts with the oxidizing agent to make a hydroxyl radical.

7. The process of claim 6 , wherein the hydroxyl radical reacts with an aromatic ring on the lignin causing the aromatic ring to open.

8. The process of claim 1 , wherein the oxidizing agent is a peroxide containing species.

9. The process of claim 1 , wherein a weight-average molecular weight of the lignin ranges from 1,000 to 4,000 g/mol.

10. The process of claim 1 , wherein an aromatic ring on the lignin is opened by one or more reactants.

11. The process of claim 1 , wherein the pH of the mixture is 2 to 6.

12. A process for valorization of lignin comprising:

mixing

lignin,

a MOF catalyst metalated with a metal atom selected from the group consisting of Fe, Mn, Co, Cu, or Ni, and combinations thereof;

an oxidizing agent; and

an aqueous solvent;

wherein the pH of the mixture is 2 to 10;

further comprising recovering the MOF catalyst.

13. The process of claim 12 , wherein the MOF catalyst comprises a node, the node including a zirconium atom; and the MOF catalyst comprises a linker including a heteroaromatic group, the linker being coupled to the node.

14. The process of claim 12 , wherein the metal atom is Fe.

15. A reaction mixture comprising:

lignin;

a MOF catalyst metalated with a metal atom selected from the group consisting of Fe, Mn, Co, Cu, or Ni, and combinations thereof;

an oxidizing agent; and

an aqueous solvent;

wherein the oxidizing agent is a peroxide-containing species;

wherein the pH of the mixture is 2 to 10;

wherein the MOF catalyst comprises a node, the node including a zirconium atom; and the MOF catalyst comprises a linker including a heteroaromatic group, the linker being coupled to the node.

16. The reaction mixture of claim 15 , wherein the lignin has an Mw/Mn ranging from 2 to 5.

17. The reaction mixture of claim 15 , wherein the MOF catalyst is a recovered MOF catalyst.

18. The reaction mixture of claim 15 , wherein the metal atom is Fe.

19. The reaction mixture of claim 15 , wherein the MOF catalyst comprises a second linker including an aromatic group, the linkers being coupled to the nodes.

Assignments (3)
CHANGE OF NAME Recorded Jun 9, 2020
From: SANDIA CORPORATION
To: NATIONAL TECHNOLOGY & ENGINEERING SOLUTIONS OF SANDIA, LLC
Reel/Frame 052874/0221 →
CONFIRMATORY LICENSE Recorded May 5, 2017
From: SANDIA CORPORATION
To: U.S. DEPARTMENT OF ENERGY
Reel/Frame 042250/0733 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 19, 2017
From: KENT, MICHAEL S.; ALLENDORF, MARK D.; STAVILA, VITALIE
To: SANDIA CORPORATION
Reel/Frame 042055/0884 →
Continuity (1)
Provisional Application 62305402 · Mar 8, 2016