# US 2020/0399722 A1 · Co-solvent to produce reactive intermediates from biomass

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 2020/0399722 A1
- Document ID: US20200399722A1
- Status: Published application
- Kind: A1
- Application number: 17/008,180
- Filed: 2020-08-31
- Published: 2020-12-24
- Earliest claimed: 2013-04-27
- Assignees: The Regents of the University of California
- Applicants: The Regents of the University of California
- Inventors: Charles M. Cai; Charles E. Wyman; Taiying Zhang; Rajeev Kumar
- Web page: https://patentgrep.com/patent/US20200399722A1

## CPC

- C13K 1/02: obtained by saccharification of cellulosic materials (manufacture of fodder A23K10/32)
- C07D 307/08: Preparation of tetrahydrofuran
- C07D 307/50: Preparation from natural products
- C07G 1/00: Low-molecular-weight derivatives of lignin (high-molecular-weight derivatives of lignin {C08H6/00})
- C12P 7/10: substrate containing cellulosic material
- C12P 17/04: containing a five-membered hetero ring, e.g. griseofulvin {, vitamin C}
- C12P 19/02: Monosaccharides (2-ketogulonic acid C12P7/60)
- D21C 3/20: with organic solvents {or in solvent environment}
- D21C 3/222: {Use of compounds accelerating the pulping processes}
- C12P 2201/00: Pretreatment of cellulosic or lignocellulosic material for subsequent enzymatic treatment or hydrolysis
- Y02E 50/10: Biofuels, e.g. bio-diesel
- 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)
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C07G: COMPOUNDS OF UNKNOWN CONSTITUTION (sulfonated fats, oils or waxes of undetermined constitution C07C309/62)
- C12P: FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE {(brewing of beer C12C; producing vinegar C12J; producing specific peptides or proteins C07K; producing enzymes C12N9/00; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification C12N15/00; measuring or testing processes involving enzymes or microorganisms C12Q; measuring or testing processes involving nucleic acid amplification reactions C12Q1/6844; fermentation processes to form a food composition, A21 or A23; compounds in general, see the relevant compound class, e.g. C01, C07)}
- D21C: PRODUCTION OF CELLULOSE BY REMOVING NON-CELLULOSE SUBSTANCES FROM CELLULOSE-CONTAINING MATERIALS; REGENERATION OF PULPING LIQUORS; APPARATUS THEREFOR
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION

## Abstract

The disclosure provides a system for production of reactive intermediates from lignocellulosic biomass. The reactive intermediates can be used as platform chemicals for biological conversions or can be further catalytically upgraded to be used as “drop in” reagents for fuels. The disclosure provides methods and compositions useful for processing biomass to biofuels and intermediates.

## Claims

### Claim 1

A method for production of reactive intermediates from biomass, comprising:
treating a biomass with a composition comprising an aqueous co-solvent mixture containing 50-75% tetrahydrofuran (THF), water, and 0.05-0.1M acid catalyst at a treatment temperature between 120° C. to 200° C. conditions to produce a liquid phase comprising dissolved monosaccharides, furfurals, and lignin; and a solid material comprising glucan; and
wherein treatment of the biomass removes greater than 70% of the lignin from the biomass,
removing and/or recovering THF from the liquid phase to produce a solid lignin product.

### Claim 2 (depends on 1)

The method of claim 1, wherein the co-solvent mixture is monophasic at Standard Temperature and Pressure (STP) and monophasic at treatment temperature.

### Claim 3 (depends on 1)

The method of claim 1, wherein the acid catalyst is selected from the group consisting of mineral acids, organic acids, and metal halide acids.

### Claim 4 (depends on 3)

The method of claim 3, wherein the acid catalyst is selected from the group consisting of sulfuric acid, hydrochloric acid, formic acid, acetic acid, trifluoroacetic acid, FeCl3, and a combination.

### Claim 5 (depends on 1)

The method of claim 1, further comprising recapture of solid lignin product by THF, DMSO, or an alcohol for further processing.

### Claim 6 (depends on 1)

The method of claim 1, further comprising removing and/or recovering furfural from a liquid phase after co-solvent treatment of the biomass by azeotropic distillation or solvent extraction.

### Claim 7 (depends on 6)

The method of claim 6, wherein the furfural is further processed to be catalytically upgraded to produce THF and/or methyl-THF.

### Claim 8 (depends on 1)

The method of claim 1, further comprising removing and/or recovering furfural after co-solvent treatment by distillation or organic solvent extraction, wherein the furfural is further processed to be catalytically upgraded to produce THF and/or methyl-THF.

### Claim 9 (depends on 1)

The method of claim 1, further comprising recovering a liquid product containing dissolved sugars.

### Claim 10 (depends on 9)

The method of claim 9, wherein the liquid product is neutralized by a base.

### Claim 11 (depends on 1)

The method of claim 1, further comprising recovering a solid product after co-solvent treatment of biomass, wherein the solid comprises a glucan-rich material having greater than 70% glucan.

### Claim 12 (depends on 11)

The method of claim 11, wherein the glucan-rich material is further treated with one or more enzymes that remove xylooligomers and higher chain length polymers of xylose to produce xylose monomers.

### Claim 13 (depends on 11)

The method of claim 11, wherein the glucan-rich material is further treated with one or more enzymes that remove glucooligomers and higher chain length polymers of glucose to produce glucose monomers.

### Claim 14 (depends on 11)

The method of claim 11, wherein the glucan-rich material is incubated with microorganisms and/or with added enzymes to produce an alcohol or other products by fermentation.

### Claim 15 (depends on 14)

The method of claim 14, wherein the alcohol is ethanol.

### Claim 16 (depends on 14)

The method of claim 14, wherein the alcohol contains 1 or more carbon molecules.

### Claim 17 (depends on 14)

The method of claim 14, wherein the microorganism is selected from the group consisting of a yeast, a bacteria, a mold, and a fungi.

### Claim 18 (depends on 11)

The method of claim 11, wherein the glucan-rich material is used for producing paper pulp or dissolving pulp.

### Claim 19 (depends on 11)

The method of claim 11, wherein the glucan-rich material is hydrolyzed to glucose and glucose-oligomers using an acid selected from the group consisting of formic acid, acetic acid, trifluoroacetic acid and any combination thereof.

### Claim 20 (depends on 1)

The method of claim 1, wherein the solid lignin product is at least 93% lignin.

### Claim 21 (depends on 1)

The method of claim 1, wherein the solid lignin product is at least 90% lignin.

### Claim 22 (depends on 1)

The method of claim 1, wherein the solid lignin product is at least 85% lignin.

### Claim 23

A method for the combined solubilization and catalytic conversion of biomass to produce reactive intermediates from biomass, comprising:
treating a biomass with a composition comprising an aqueous co-solvent mixture containing 66%-83% tetrahydrofuran (THF), water, and 0.1-0.2M acid catalyst at a treatment temperature between 170° C. to 220° C. conditions to produce a liquid phase comprising furfural, 5-hydroxymethylfurfural, levulinic acid, and lignin; and
removing and/or recovering THF from the liquid phase to produce a solid lignin product by removing greater than 70% of the lignin from the biomass, wherein
(i) the co-solvent mixture is monophasic at Standard Temperature and Pressure and during treatment;
(ii) the acid catalyst is selected from the group consisting of mineral acids, organic acids, metal halide acids, and solid acid catalysts;
(iii) the acid catalyst is selected from the group consisting of sulfuric acid, hydrochloric acid, trifluoroacetic acid, FeCI3, AICI3, CUCI2 and any combination thereof;
(iv) further comprising removing and/or recovering THF from the liquid phase after co-solvent treatment of the biomass;
(v) further comprising removing and/or recovery of lignin from the co-solvent treatment of the biomass by precipitation as a solid after the distillation of THF from the liquid phase;
(vi) further comprising removing and/or recovering furfural and/or 5-HMF from a liquid phase of the co-solvent treatment of the biomass by distillation;
(vii) further comprising removing and/or recovery furfural during and/or after co-solvent treatment by boiling and/or steam stripping, or
(viii) further comprising extracting and/or recovering furfural and/or 5-HMF from a liquid phase of the co-solvent treatment of the biomass by a water-immiscible organic solvent.

### Claim 24 (depends on 23)

The method of claim 23, wherein the lignin is further processed and captured by THF or DMSO as a liquid.

### Claim 25 (depends on 23)

The method of claim 23, wherein the furfural is further processed to be catalytically decarbonated or hydrogenated to produce a saturated or unsaturated furan.

### Claim 26 (depends on 23)

The method of claim 23, wherein the immiscible organic solvent is an ether, ketone, alcohol, alkane or any combination thereof.

### Claim 27 (depends on 23)

The method of claim 23, wherein the solid lignin product is at least 93% lignin.

### Claim 28 (depends on 23)

The method of claim 23, wherein the solid lignin product is at least 90% lignin.

### Claim 29 (depends on 23)

The method of claim 23, wherein the solid lignin product is at least 85% lignin.

### Claim 30

A method for production of reactive intermediates from biomass, comprising:
treating a biomass with a composition comprising a single phase co-solvent mixture of aqueous tetrahydrofuran (THF) and an acid catalyst under conditions to produce a liquid phase comprising biomass-derived, monomeric sugars, oligosaccharides, and lignin products and a solid material comprising biomass-derived polysaccharides; and
removing and/or recovery of lignin from the co-solvent treated biomass by precipitation as a solid after the removal of THF from the liquid phase.

### Claim 31 (depends on 30)

The method of claim 30, wherein lignin is further processed and captured by THF, DMSO, or an alcohol as a liquid.