# US 8,772,557 B2 · Aromatic hydrocarbons from depolymerization and deoxygenation of lignin

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

- Number: US 8,772,557 B2
- Document ID: US8772557B2
- Status: Granted
- Kind: B2
- Application number: 13/190,751
- Filed: 2011-07-26
- Published: 2013-01-31
- Granted: 2014-07-08
- Earliest claimed: 2011-07-26
- Assignees: Uop LLC
- Applicants: John Qianjun Chen; Mark Blaise Koch
- Inventors: John Qianjun Chen; Mark Blaise Koch
- Web page: https://patentgrep.com/patent/US8772557B2

## CPC

- C10L 1/02: essentially based on components consisting of carbon, hydrogen, and oxygen only
- C10G 1/065: {in the presence of a solvent}
- C10L 1/023: {for spark ignition}
- C10L 1/14: Organic compounds
- C10L 1/1616: {fractions, e.g. lubricants, solvents, naphta, bitumen, tars, terpentine}
- C10L 1/1824: {mono-hydroxy}
- B01J 21/12: Silica and alumina
- B01J 23/883: and nickel
- C10G 2300/305: Octane number, e.g. motor octane number [MON], research octane number [RON]
- C10L 2200/0423: Gasoline
- C10L 2200/0469: Renewables or materials of biological origin
- 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
- 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
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS

## Abstract

Processes are disclosed that achieve a high conversion of lignin to aromatic hydrocarbons, and that may be carried out without the addition of a base. Depolymerization and deoxygenation, the desired lignin convention steps to yield aromatic hydrocarbons, are carried by contacting a mixture of lignin and a solvent (e.g., a lignin slurry) with hydrogen in the presence of a catalyst. A preferred solvent is a hydrogen transfer solvent such as a single-ring or fused-ring aromatic compound that beneficially facilitates depolymerization and hinders coke formation. These advantages result in favorable overall process economics for obtaining fuel components and/or chemicals from renewable sources.

## Claims

### Claim 1

A method of making aromatic hydrocarbons comprising:
(a) contacting hydrogen, in the presence of a catalyst, with a mixture of lignin and an aromatic-containing solvent under reaction conditions effective to convert at least a portion of the lignin and provide a lignin conversion effluent having an increased quantity of aromatic hydrocarbons relative to the mixture, wherein the aromatic-containing solvent contains at least about 50% by volume aromatic hydrocarbons and the reaction conditions comprise a hydrogen partial pressure from 700 kPa (100 psig) to about 21 MPa (3000 psig); and
(b) separating a lignin conversion product from the lignin conversion effluent.

### Claim 2 (depends on 1)

The method of claim 1, wherein the aromatic-containing solvent comprises a single ring or fused ring aromatic compound.

### Claim 3 (depends on 1)

The method of claim 1, wherein the aromatic-containing solvent comprises a byproduct of a hydrocarbon conversion process.

### Claim 4 (depends on 3)

The method of claim 3, wherein the byproduct is a C9+ hydrocarbon fraction.

### Claim 5 (depends on 1)

The method of claim 1, wherein the catalyst has both a hydrogenation function and an acid function.

### Claim 6 (depends on 5)

The method of claim 5, wherein the hydrogenation function is a catalytic metal selected from the group consisting of ruthenium, platinum, palladium, iron, cobalt, nickel, molybdenum, tungsten, and mixtures thereof.

### Claim 7 (depends on 5)

The method of claim 5, wherein the acid function is an acidic support material selected from the group consisting of a clay, a zeolite, a non-zeolitic molecular sieve, a mixed metal oxide, sulfated zirconia, and mixtures thereof.

### Claim 8 (depends on 1)

The method of claim 1, wherein the reaction conditions include a temperature from about 200° C. (392° F.) to about 600° C. (1112° F.), and a weight hourly space velocity (WHSV) from about 0.1 hr−1 to about 20 hr−1.

### Claim 9 (depends on 1)

The method of claim 1, wherein the lignin is obtained from the pyrolysis of biomass.

### Claim 10 (depends on 1)

The method of claim 1, wherein the biomass is selected from the group consisting of hardwood, softwood, hardwood bark, softwood bark, corn fiber, corn stover, sugar cane bagasse, switchgrass, miscanthus, algae, waste paper, construction waste, demolition waste, municipal waste, and mixtures thereof.

### Claim 11 (depends on 1)

The method of claim 1, wherein at least a portion of the lignin is obtained as a byproduct of wood pulping.

### Claim 12 (depends on 1)

The method of claim 1, wherein at least a portion of the lignin is obtained as a co-product of ethanol production from biomass.

### Claim 13 (depends on 1)

The method of claim 1, wherein the lignin conversion product comprises less than about 0.1% organic oxygen by weight.

### Claim 14 (depends on 1)

The method of claim 1, wherein the lignin conversion product comprises at least about 97% hydrocarbons by weight.

### Claim 15 (depends on 1)

The method of claim 1, wherein the lignin conversion product comprises from about 55% to about 85% aromatic hydrocarbons by weight.

### Claim 16 (depends on 1)

The method of claim 1, wherein the lignin conversion product has a research octane number (RON) from about 95 to about 105.

### Claim 17

A method for making a fuel composition, the method comprising:
(a) forming a lignin mixture comprising lignin and a solvent comprising a single ring or fused ring aromatic compound, wherein the solvent contains at least about 50% by volume of aromatic hydrocarbons;
(b) contacting the lignin mixture with hydrogen under catalytic depolymerization/deoxygenation conditions to provide a lignin conversion effluent, wherein the catalytic depolymerization/deoxygenation conditions comprise a hydrogen partial pressure from 700 kPa (100 psig) to about 21 MPa (3000 psig);
(c) separating a lignin conversion product from the lignin conversion effluent; and
(d) blending the lignin conversion product with from 1% to 99% by weight of a petroleum derived gasoline.