# US 11,306,264 B2 · Biofuel composition comprising lignin

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- Number: US 11,306,264 B2
- Document ID: US11306264B2
- Status: Granted
- Kind: B2
- Application number: 16/969,480
- Filed: 2019-02-18
- Published: 2020-12-24
- Granted: 2022-04-19
- Earliest claimed: 2018-02-16
- Assignees: A.P. Møller—Mærsk A/S; Københavns Universitet
- Applicants: A.P. MøLler—MæRsk A/S; KøBenhavns Universitet
- Inventors: Claus Felby; Stefan Mayer; Yohanna Cabrera Orozco
- Web page: https://patentgrep.com/patent/US11306264B2

## CPC

- C10G 1/045: {Separation of insoluble materials}
- C10L 1/02: essentially based on components consisting of carbon, hydrogen, and oxygen only
- C08H 6/00: {Macromolecular compounds derived from lignin, e.g. tannins, humic acids}
- C08L 5/14: Hemicellulose; Derivatives thereof
- C08L 97/005: {Lignin}
- C10L 10/12: for improving the cetane number
- D21C 3/20: with organic solvents {or in solvent environment}
- D21C 3/22: Other features of pulping processes
- 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)}
- C10L 2200/0469: Renewables or materials of biological origin
- C10L 2290/06: Heat exchange, direct or indirect
- C10L 2290/544: Extraction for separating fractions, components or impurities during preparation or upgrading of a fuel
- C10L 2290/547: Filtration for separating fractions, components or impurities during preparation or upgrading of a fuel
- Y02E 50/10: Biofuels, e.g. bio-diesel
- C10G: CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION (cracking to hydrogen or synthesis gas C01B; cracking or pyrolysis of hydrocarbon gases to individual hydrocarbons or mixtures thereof of definite or specified constitution C07C; cracking to cokes C10B); RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10L: FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
- C08H: DERIVATIVES OF NATURAL MACROMOLECULAR COMPOUNDS (polysaccharides C08B; natural rubber C08C; natural resins or their derivatives C09F; bituminous materials C10)
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- 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 biofuel composition and a process for the manufacture of a biofuel composition including lignin and ethanol as the main combustible components of the biofuel composition and having total ash below 1% w/w based on total mass of dry matter in the biofuel composition.

## Claims

### Claim 1

A process for the manufacture of a biofuel composition comprising processed lignin and ethanol as its main combustible components having total ash below 1% w/w based on total mass of dry matter in said biofuel composition, said process comprising:
i. providing a slurry comprising ethanol and a biomass comprising lignin as its main combustible component;
ii. subjecting said slurry to an organosolv extraction at an extraction temperature T1 from 100° C. to 250° C., at an extraction pressure P1 from 10 bar to 60 bar, and for an extraction time t1 not exceeding 24 hours, thereby providing a resulting slurry and a precipitate;
iv. separating said resulting slurry of step ii. from said precipitate; and
vi. cooling said resulting slurry of step iv. to obtain said biofuel composition.

### Claim 2 (depends on 1)

The process according to claim 1 further comprising a process iii. wherein said resulting slurry and said precipitate are cooled prior to said separating.

### Claim 3 (depends on 1)

The process according to claim 1 further comprising a process v. wherein said resulting slurry of process iv. is concentrated by removal of ethanol.

### Claim 4 (depends on 1)

The process according to claim 1, wherein said separating is by filtration or centrifugation.

### Claim 5 (depends on 1)

The process according to claim 1, wherein a total of ash is not more than 0.5% w/w based on total mass of dry matter in said biofuel composition.

### Claim 6 (depends on 1)

The process according to claim 1, wherein said biomass comprising lignin comprises less than 20% w/w of water based on total mass of said biomass.

### Claim 7 (depends on 1)

The process according to claim 1, wherein a concentration of biomass in ethanol does not exceed 50% w/w dry matter based on total mass of slurry.

### Claim 8 (depends on 1)

The process according to claim 1, wherein said organosolv extraction of process ii. is performed while a catalyst is present.

### Claim 9 (depends on 8)

The process according to claim 8, wherein said catalyst is a Lewis acid type catalyst.

### Claim 10 (depends on 8)

The process according to claim 8, wherein said catalyst comprised in said resulting slurry of process ii. is neutralized or precipitated prior to said separating of process iv.

### Claim 11 (depends on 1)

The process according to claim 1, wherein said extraction temperature T1 is from 100° C. to 225° C.

### Claim 12 (depends on 1)

The process-according to claim 1, wherein said extraction pressure P1 is from 15 bar to 22 bar.

### Claim 13 (depends on 1)

The process according to claim 1, wherein said extraction time t1 does not exceed 5 hours.

### Claim 14 (depends on 1)

The process according to claim 1, wherein said extraction temperature T1 is from 150° C. to 200° C., said extraction pressure P1 is from 18 bar to 20 bar, and said extraction time t1 is from 15 minutes to 30 minutes.

### Claim 15 (depends on 1)

The process according to claim 1, wherein at least one surfactant is comprised in or added to a slurry of said process.

### Claim 16 (depends on 1)

The process according to claim 1, wherein at least one surfactant is added to a slurry comprised in said process not later than just after said separating in process iv.

### Claim 17 (depends on 1)

The process according to claim 1, wherein at least one cetane enhancer is added prior to said organosolv extraction of process ii.

### Claim 18

A biofuel composition comprising:
ethanol; and
processed lignin solubilized and/or dispersed in said ethanol as main combustible mass fractions and comprising not more than 1% w/w of ashes based on total dry mass of said biofuel composition.

### Claim 19 (depends on 18)

The biofuel composition according to claim 18, further comprising processed lignin in a concentration from 3% w/w to 60% w/w of lignin based on total mass of said biofuel composition.

### Claim 20 (depends on 18)

The biofuel composition according to claim 18, further comprising at least one surfactant at a concentration of said at least one surfactant in said biofuel composition from 0.001% to 10% w/w of surfactant based on total mass of said biofuel composition.

### Claim 21 (depends on 20)

The biofuel composition according to claim 20, wherein said at least one surfactant is a nonionic surfactant.

### Claim 22 (depends on 18)

The biofuel composition according to claim 18, further comprising at least one combustible biomass fraction which is not of lignocellulosic origin present in amounts from 0.5% to 5% by weight of total dry mass.

### Claim 23

A biofuel composition comprising a biofuel comprising processed lignin and ethanol as its main combustible components having total ash below 1% w/w based on total mass of dry matter in said biofuel composition, wherein said biofuel is obtained by a process comprising:
i. providing a slurry comprising ethanol and a biomass comprising lignin as its main combustible component;
ii. subjecting said slurry to an organosolv extraction at an extraction temperature T1 from 100° C. to 250° C., at an extraction pressure P1 from 10 bar to 60 bar, and for an extraction time t1 not exceeding 24 hours, thereby providing a resulting slurry and a precipitate
iv. separating said resulting slurry of step ii. from said precipitate; and
vi. cooling said resulting slurry of step iv. to obtain said biofuel composition.

### Claim 24 (depends on 3)

The process according to claim 3, wherein in process v. said resulting slurry of process iv. is concentrated by removal of ethanol until formation of a second precipitate is observed.

### Claim 25 (depends on 8)

The process according to claim 8, wherein said catalyst is selected from the group consisting of sodium hydroxide, formic acid, and para toluene sulfonic acid (pTSA).
