# US 10,370,501 B2 · Treatment of lignocellulosic biomass with aromatic chemicals as scavengers

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- Number: US 10,370,501 B2
- Document ID: US10370501B2
- Status: Granted
- Kind: B2
- Application number: 15/317,293
- Filed: 2015-06-15
- Published: 2017-05-18
- Granted: 2019-08-06
- Earliest claimed: 2014-06-17
- Assignees: ETH Zurich
- Applicants: ETH Zurich
- Inventors: Philipp Rudolf von Rohr; Thomas Pielhop; Gastón Larrazábal Labrador
- Web page: https://patentgrep.com/patent/US10370501B2

## CPC

- C08H 8/00: Macromolecular compounds derived from lignocellulosic materials {(pretreatment thereof B27N)}
- C12P 19/02: Monosaccharides (2-ketogulonic acid C12P7/60)
- C12P 19/14: produced by the action of a carbohydrase {(EC 3.2.x)}, e.g. by alpha-amylase {, e.g. by cellulase, hemicellulase}
- D21C 1/02: with water or steam
- D21C 3/222: {Use of compounds accelerating the pulping processes}
- D21C 9/005: {organic compounds}
- D21C 11/0007: {Recovery of by-products, i.e. compounds other than those necessary for pulping, for multiple uses or not otherwise provided for (volatile compounds obtained by decomposition of spent liquors in order to regenerate them D21C11/125; compounds obtained by fractionating the liquors in order to regenerate them D21C11/0042)}
- C12P 2201/00: Pretreatment of cellulosic or lignocellulosic material for subsequent enzymatic treatment or hydrolysis
- D21C 5/005: {Treatment of cellulose-containing material with microorganisms or enzymes}
- Y02E 50/10: Biofuels, e.g. bio-diesel
- C08H: DERIVATIVES OF NATURAL MACROMOLECULAR COMPOUNDS (polysaccharides C08B; natural rubber C08C; natural resins or their derivatives C09F; bituminous materials C10)
- 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

A method for using at least one compound as a scavenger, in particular as a scavenger in the hydrolytic treatment of lignocellulosic biomass is provided. The compound includes at least one aromatic ring substituted with at least two moieties each having a free electron pair, wherein the at least two moieties are arranged in meta-position to each other, and at least two alkyl or alkenyl moieties.

## Claims

### Claim 1

A process for the production of a cellulosic feedstock by hydrolytic treatment of lignocellulosic biomass wherein at least one compound is added to the lignocellulosic biomass during at least one of before, during or after the aqueous treatment autohydrolysis of the lignocellulosic biomass, wherein the compound is selected from at least one compound of
the general formula (II)
wherein
X1, X2, X3=OH,
R=unsubstituted or substituted alkyl substituent(s) or unsubstituted or substituted alkenyl substituent(s), and
n=2.

### Claim 2 (depends on 1)

The process according to claim 1, wherein the aqueous treatment of the lignocellulosic biomass is a liquid hot water treatment or an aqueous steam treatment.

### Claim 3 (depends on 1)

The process according to claim 1, wherein lignocellulosic biomass consists of lignocellulosic material containing fermentable carbohydrate.

### Claim 4 (depends on 1)

The process according to claim 1, wherein the aqueous treatment autohydrolysis of the lignocellulosic biomass is carried out under inert gas, oxygen containing, ozone containing or hydrogen containing atmosphere.

### Claim 5 (depends on 1)

The process according to claim 1, wherein the aqueous treatment autohydrolysis of the lignocellulosic biomass is carried out in a temperature range from 100 to 260° C., and at a pressure within the range from 0 to 500 bar.

### Claim 6 (depends on 1)

The process according to claim 1, wherein the pH during the aqueous treatment of the lignocellulosic biomass is adjusted by the addition of at least one acid.

### Claim 7 (depends on 1)

The process according to claim 1, wherein the pH during the aqueous treatment of the lignocellulosic biomass is adjusted by the addition of at least one base.

### Claim 8 (depends on 1)

The process according to claim 1, wherein the water to dry biomass ratio is in the range between 1:5 and 100:1.

### Claim 9 (depends on 1)

The process according to claim 1, wherein the at least one compound used as scavenger is added an amount between 0.01 to 20% w/w based on dry biomass loading.

### Claim 10 (depends on 1)

The process according to claim 1, wherein any unreacted scavenger compound is recovered after autohydrolysis treatment and recycled to the autohydrolysis treatment stage.

### Claim 11 (depends on 1)

The process according to claim 1, wherein the reacted scavenger compound is recovered after autohydrolysis with a laccase treatment and recycled to the autohydrolysis treatment stage.

### Claim 12 (depends on 1)

The process according to claim 1, wherein the hydrolytically treated lignocellulosic biomass is washed before entering the enzymatic hydrolysis stage.

### Claim 13 (depends on 1)

The process according to claim 1, wherein the lignocellulosic biomass comprises lignocellulosic material containing fermentable carbohydrate comprising at least one of softwood spruce, hardwood beech, herbs or agricultural residues.

### Claim 14 (depends on 1)

The process according to claim 1, wherein the aqueous treatment autohydrolysis of the lignocellulosic biomass is carried out under inert gas or air.

### Claim 15 (depends on 1)

The process according to claim 1, wherein the aqueous treatment autohydrolysis of the lignocellulosic biomass is carried out in a temperature range from 190 to 240° C.

### Claim 16 (depends on 1)

The process according to claim 1, herein the aqueous treatment autohydrolysis of the lignocellulosic biomass is carried out at a pressure within the range from 1 to 40 bar.

### Claim 17 (depends on 1)

The process according to claim 1, wherein the pH during the aqueous treatment of the lignocellulosic biomass is adjusted by the addition of at least one inorganic acid which comprises nitric acid, hydrochloric acid, phosphoric acid or mixtures thereof.

### Claim 18 (depends on 1)

The process according to claim 1, wherein the pH during the aqueous treatment of the lignocellulosic biomass is adjusted by the addition of at least one organic acid which comprises acetic acid, formic acid or mixtures thereof.

### Claim 19 (depends on 1)

The process according to claim 1, wherein the pH during the aqueous treatment of the lignocellulosic biomass is adjusted by the addition of at least one inorganic base which comprises at least one alkali salt.

### Claim 20 (depends on 19)

The process according to claim 19, wherein the alkali salt comprises sodium hydroxide.

### Claim 21 (depends on 1)

The process according to claim 1, wherein the pH during the aqueous treatment of the lignocellulosic biomass is adjusted by the addition of at least one organic base which comprises pyridine.

### Claim 22 (depends on 1)

The process according to claim 1, wherein the water to dry biomass ratio is in the range between 1:1 and 5:1.

### Claim 23 (depends on 1)

The process according to claim 1, wherein the compound is:
wherein R1 and R2 have the meaning of R and are the same or different.

### Claim 24 (depends on 1)

The process according to claim 1, wherein each R is independently selected from a C1-C10 alkyl substituent or a C1-C10 alkenyl substituent.

### Claim 25 (depends on 1)

The process according to claim 1, wherein each R is independently selected from a C1-C5 alkyl substituent or a C1-C5 alkenyl substituent.

### Claim 26 (depends on 1)

The process according to claim 1, wherein each R is independently selected from a methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, propenyl, butenyl or pentenyl substituent.

### Claim 27 (depends on 1)

The process according to claim 1, wherein the compound comprises dimethylphloroglucinol.

### Claim 28 (depends on 1)

The process according to claim 1, wherein the compound is dimethylphloroglucinol.

### Claim 29 (depends on 1)

A cellulosic feedstock or lignin fraction obtainable by a process according to claim 1.
