# US 11,077,435 B2 · Catalyst and method for fractionating lignocellulosic material

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- Number: US 11,077,435 B2
- Document ID: US11077435B2
- Status: Granted
- Kind: B2
- Application number: 16/928,673
- Filed: 2020-07-14
- Published: 2020-10-29
- Granted: 2021-08-03
- Earliest claimed: 2017-07-24
- Assignees: WiSys Technology Foundation, Inc.
- Applicants: WiSys Technology Foundation, Inc.
- Inventors: Malek Alkasrawi; Joynal Abedin
- Web page: https://patentgrep.com/patent/US11077435B2

## CPC

- B01J 31/2295: {Cyclic compounds, e.g. cyclopentadienyls}
- B01J 21/08: Silica
- B01J 31/1625: {immobilised by covalent linkages, i.e. pendant complexes with optional linking groups}
- B01J 31/2273: {with only nitrogen as heteroatomic ring members, e.g. 1,3-diarylimidazoline-2-ylidenes}
- B01J 31/28: of the platinum group metals, iron group metals or copper
- B01J 35/19: {Catalysts containing parts with different compositions}
- B01J 35/33: Electric or magnetic properties
- B01J 37/0219: {the coating containing organic compounds}
- B01J 37/0221: {of particles}
- B01J 37/04: Mixing {(B01J37/0009, B01J37/0018 take precedence)}
- C07G 1/00: Low-molecular-weight derivatives of lignin (high-molecular-weight derivatives of lignin {C08H6/00})
- C13K 1/02: obtained by saccharification of cellulosic materials (manufacture of fodder A23K10/32)
- B01J 23/745: Iron
- B01J 35/45: Nanoparticles
- B01J 2531/847: Nickel
- Y02P 20/50: Improvements relating to the production of bulk chemicals
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- C07G: COMPOUNDS OF UNKNOWN CONSTITUTION (sulfonated fats, oils or waxes of undetermined constitution C07C309/62)
- C13K: SACCHARIDES OBTAINED FROM NATURAL SOURCES OR BY HYDROLYSIS OF NATURALLY OCCURRING DISACCHARIDES, OLIGOSACCHARIDES OR POLYSACCHARIDES (chemically synthesised sugars or sugar derivatives C07H; polysaccharides, e.g. starch, derivatives thereof C08B; malt C12C; fermentation or enzyme-using processes for preparing compounds containing saccharide radicals C12P19/00; production of sucrose C13B)
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

## Abstract

Various embodiments disclosed relate to solid catalysts that convert lignocellulosic material to monomer sugars that are suitable for fermentation. The solid catalysts include a transition metal complex attached to a magnetic bead, and can be physically separated from a fermentation mixture and reused several times.

## Claims

### Claim 1

A catalyst having the structure:
wherein X is a counterion;
L is a linker group;
MB is a magnetic metal-containing bead; and
R1 and R2 is each C1-10 alkyl, C7-10 aralkyl, C6-C12 aryl, or C2-8 heterocyclyl, each of which is optionally substituted.

### Claim 2 (depends on 1)

The catalyst of claim 1, wherein the magnetic metal-containing bead comprises iron oxide.

### Claim 3 (depends on 1)

The catalyst of claim 1, wherein the magnetic metal-containing bead has an average size of 0.001 micrometer to 100 micrometer.

### Claim 4 (depends on 1)

The catalyst of claim 1, wherein 10% to 100% of the surface of the magnetic metal-containing bead is coated by amorphous silica.

### Claim 5 (depends on 4)

The catalyst of claim 4, wherein the linker comprises a silane on one terminal end which covalently binds to the silica surface of the magnetic metal-containing bead.

### Claim 6 (depends on 5)

The catalyst of claim 5, wherein the linker is attached to the silica surface of the magnetic metal-containing bead by a siloxane linkage and attached to the remaining portion of the catalyst molecule via carbamate, urea, thiocarbamate, thiourea, amide or ester linkage.

### Claim 7 (depends on 1)

The catalyst of claim 1, wherein the linker comprises a functional group on one terminal end which binds to a functionalized surface of the magnetic metal-containing bead, so as to covalently link the magnetic metal-containing bead to the remainder of the catalyst.

### Claim 8 (depends on 1)

The catalyst of claim 1, wherein the linker is attached according to the structure:

### Claim 9 (depends on 1)

The catalyst of claim 1, wherein R1 and R2 are each independently
wherein R3, R4, R5, R6 and R7 are each independently H, C1-C10 alkyl.

### Claim 10 (depends on 9)

The catalyst of claim 9, wherein R1 and R2 are

### Claim 11 (depends on 9)

The catalyst of claim 9, wherein R1 and R2 are

### Claim 12 (depends on 1)

The catalyst of claim 1, wherein the linker comprises a silane, thiol, phosphate, amine, or biotin.

### Claim 13 (depends on 12)

The catalyst of claim 12, wherein the silane is a siloxane.

### Claim 14 (depends on 1)

The catalyst of claim 1, wherein the linker comprises a silane, thiol, phosphate, amine, or biotin which is attached to a functionalized surface of the magnetic metal-containing bead, and the linker further comprises a carbamate, urea, thiocarbamate, thiourea, amide or ester on another terminal end which covalently links to the remainder of the catalyst.

### Claim 15 (depends on 1)

The catalyst of claim 1, wherein the magnetic metal-containing bead is surface functionalized with one or more of an epoxy, vinyl sulfone, thiol, iodoacetlyl, hydrazide, tosyl, amine, carboxy, epoxy, aldehyde, avidin, or amorphous silica.

### Claim 16 (depends on 15)

The catalyst of claim 15, wherein the magnetic metal-containing bead is surface functionalized with amorphous silica and the linker comprises a silane.

### Claim 17 (depends on 15)

The catalyst of claim 15, wherein the magnetic metal-containing bead is surface functionalized with epoxy, vinyl sulfone, thiol or iodoacetlyl, and the linker comprises a thiol.

### Claim 18 (depends on 15)

The catalyst of claim 15, wherein the magnetic metal-containing, bead is surface functionalized with tosyl, amine, carboxy, epoxy, aldehyde, and the linker comprises an amine.

### Claim 19 (depends on 15)

The catalyst of claim 15, wherein the magnetic metal-containing bead is surface functionalized with hydrazide or amine, and the linker comprises a phosphate or amine.

### Claim 20 (depends on 15)

The catalyst of claim 15, wherein the magnetic metal-containing bead is surface functionalized with Avidin, and the linker comprises a biotin.
