# US 9,518,305 B2 · Organo-catalytic biomass deconstruction

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- Number: US 9,518,305 B2
- Document ID: US9518305B2
- Status: Granted
- Kind: B2
- Application number: 14/968,361
- Filed: 2015-12-14
- Published: 2016-04-07
- Granted: 2016-12-13
- Earliest claimed: 2010-12-30
- Assignees: Virent, Inc.
- Applicants: Virent, Inc.
- Inventors: Ming Qiao; Randy D. Cortright; Elizabeth Woods
- Web page: https://patentgrep.com/patent/US9518305B2

## CPC

- C13K 1/02: obtained by saccharification of cellulosic materials (manufacture of fodder A23K10/32)
- B01J 23/464: {Rhodium}
- B01J 23/52: Gold
- B01J 23/687: {with tungsten}
- C07B 63/00: Purification; Separation (separation of optically-active compounds C07B57/00); Stabilisation; Use of additives
- C08B 30/12: Degraded, {destructured} or non-chemically modified starch {, e.g. mechanically, enzymatically or by irradiation; Bleaching of starch (preparation of chemical derivatives of starch C08B31/00)}
- C10G 1/002: {in combination with oil conversion- or refining processes}
- C10G 1/06: by destructive hydrogenation
- C10G 1/065: {in the presence of a solvent}
- C10G 1/086: {Characterised by the catalyst used}
- C10G 3/00: Production of liquid hydrocarbon mixtures from oxygen-containing organic materials, e.g. fatty oils, fatty acids (production from non-melting solid oxygen-containing carbonaceous materials C10G1/00)
- C10G 3/42: {Catalytic treatment}
- C10G 3/44: {characterised by the catalyst used}
- C10G 3/45: {containing iron group metals or compounds thereof}
- C10G 3/46: {in combination with chromium, molybdenum, tungsten metals or compounds thereof}
- C10G 3/47: {containing platinum group metals or compounds thereof}
- C10G 3/48: {further characterised by the catalyst support}
- C10G 3/49: {containing crystalline aluminosilicates, e.g. molecular sieves}
- C10G 3/50: {in the presence of hydrogen, hydrogen donors or hydrogen generating compounds}
- C10G 3/52: {Hydrogen in a special composition or from a special source}
- C10L 1/04: essentially based on blends of hydrocarbons
- C13K 13/00: Sugars not otherwise provided for in this class
- B01J 20/34: Regenerating or reactivating
- B01J 23/462: {Ruthenium}
- B01J 23/6527: {Tungsten}
- C07C 29/132: by reduction of an oxygen containing functional group
- C10G 2300/1011: Biomass
- C10G 2300/1014: of vegetal origin
- C10G 2300/202: Heteroatoms content, i.e. S, N, O, P
- C10G 2300/4081: Recycling aspects
- C10G 2300/44: Solvents
- C10G 2300/805: Water
- C10G 2400/04: Diesel oil
- C10G 2400/30: Aromatics
- Y02P 30/20: using bio-feedstock
- Y02P 30/40: Ethylene production
- 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)
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- C07B: GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR (preparation of carboxylic acid esters by telomerisation C07C67/47; telomerisation C08F)
- C08B: POLYSACCHARIDES; DERIVATIVES THEREOF (polysaccharides containing less than six saccharide radicals attached to each other by glycosidic linkages C07H; fermentation or enzyme-using processes C12P19/00; sugar industry C13; production of cellulose D21)
- 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
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

## Abstract

The present invention provides processes for catalytic deconstruction of biomass using a solvent produced in a bioreforming reaction.

## Claims

### Claim 1

A method of making a biomass hydrolysate, the method comprising:
A. catalytically reacting water and a water-soluble C2+O1+ oxygenated hydrocarbon in a liquid or vapor phase with H2 in the presence of a deoxygenation catalyst at a deoxygenation temperature and deoxygenation pressure to produce a biomass processing solvent comprising a C2+O1-3 hydrocarbon in a reaction stream; and
B. reacting the biomass processing solvent with a solid biomass component, hydrogen and a deconstruction catalyst at a deconstruction temperature and a deconstruction pressure to produce a biomass hydrolysate comprising at least one member selected from the group consisting of a water-soluble lignocellulose derivative, a water-soluble cellulose derivative, a water-soluble hemicellulose derivative, a carbohydrate, a starch, a monosaccharide, a disaccharide, a polysaccharide, a sugar, a sugar alcohol, an alditol and a polyol,
C. recycling the biomass hydrolysate into the reactants of step B.

### Claim 2 (depends on 1)

The method of claim 1, wherein the biomass processing solvent comprises a member selected from the group consisting of an alcohol, ketone, aldehyde, cyclic ether, ester, diol, triol, hydroxy carboxylic acid, carboxylic acid, and a mixture thereof.

### Claim 3 (depends on 1)

The method of claim 1, wherein the deconstruction catalyst comprises an acidic resin or a basic resin.

### Claim 4 (depends on 3)

The method of claim 3, wherein the deconstruction catalyst further comprises a member selected from the group consisting of Fe, Co, Ni, Cu, Ru, Rh, Pd, Pt, Re, Mo, W, an alloy thereof, and a combination thereof.

### Claim 5 (depends on 1)

The method of claim 1, wherein the deconstruction catalyst comprises a support and a member adhered to the support, wherein the member is selected from the group consisting of Cu, Fe, Ru, Ir, Co, Rh, Pt, Pd, Ni, W, Mo, an alloy thereof, and a combination thereof.

### Claim 6 (depends on 5)

The method of claim 5, wherein the deconstruction catalyst further comprises a member selected from the group consisting of Cu, Mn, Cr, Mo, B, W, V, Nb, Ta, Ti, Zr, Y, La, Sc, Zn, Cd, Ag, Au, Sn, Ge, P, Al, Ga, In, Tl, an alloy thereof, and a combination thereof.

### Claim 7 (depends on 1)

The method of claim 1, wherein the oxygenated hydrocarbon is selected from the group consisting of a starch, a carbohydrate, a polysaccharide, a disaccharide, a monosaccharide, a sugar, a sugar alcohol, a alditol, an organic acid, a phenol, a cresol, ethanediol, ethanedione, acetic acid, propanol, propanediol, propionic acid, glycerol, glyceraldehyde, dihydroxyacetone, lactic acid, pyruvic acid, malonic acid, a butanediol, butanoic acid, an aldotetrose, tartaric acid, an aldopentose, an aldohexose, a ketotetrose, a ketopentose, a ketohexose, a hemicellulose, a cellulosic derivative, a lignocellulosic derivative, and a polyol.

### Claim 8

A method of making a biomass hydrolysate, the method comprising:
A. catalytically reacting water and a water-soluble C2+O1+ oxygenated hydrocarbon in a liquid or vapor phase with H2 in the presence of a deoxygenation catalyst at a deoxygenation temperature and deoxygenation pressure to produce an oxygenate comprising a C2+O1-3 hydrocarbon in a reaction stream;
B. catalytically reacting in the liquid or vapor phase the oxygenate in the presence of a condensation catalyst at a condensation temperature and condensation pressure to produce a biomass processing solvent comprising one or more C4+ compounds; and
C. reacting the biomass processing solvent with a solid biomass component, hydrogen and a deconstruction catalyst at a deconstruction temperature and a deconstruction pressure to produce a biomass hydrolysate comprising at least one member selected from the group consisting of a water-soluble lignocellulose derivative, a water-soluble cellulose derivative, a water-soluble hemicellulose derivative, a carbohydrate, a starch, a monosaccharide, a disaccharide, a polysaccharide, a sugar, a sugar alcohol, an alditol, and a polyol,
D. recycling the biomass hydrolysate into the reactants of step C.

### Claim 9 (depends on 8)

The method of claim 8, wherein the biomass processing solvent comprises a member selected from the group consisting of an alkane, alkene and an aromatic.

### Claim 10 (depends on 9)

The method of claim 9, wherein the biomass processing solvent comprises a member selected from the group consisting of benzene, toluene and xylene.

### Claim 11 (depends on 8)

The method of claim 8, wherein the deconstruction catalyst comprises an acidic resin or a basic resin.

### Claim 12 (depends on 11)

The method of claim 11, wherein the deconstruction catalyst further comprises a member selected from the group consisting of Fe, Co, Ni, Cu, Ru, Rh, Pd, Pt, Re, Mo, W, an alloy thereof, and a combination thereof.

### Claim 13 (depends on 8)

The method of claim 8, wherein the deconstruction catalyst comprises a support and a member adhered to the support selected from the group consisting of Cu, Fe, Ru, Ir, Co, Rh, Pt, Pd, Ni, W, Mo, an alloy thereof, and a combination thereof.

### Claim 14 (depends on 13)

The method of claim 13, wherein the deconstruction catalyst further comprises a member selected from the group consisting of Cu, Mn, Cr, Mo, B, W, V, Nb, Ta, Ti, Zr, Y, La, Sc, Zn, Cd, Ag, Au, Sn, Ge, P, Al, Ga, In, Tl, an alloy thereof, and a combination thereof.

### Claim 15 (depends on 8)

The method of claim 8, wherein C2+O1+ hydrocarbon is selected from the group consisting of a starch, a carbohydrate, a polysaccharide, a disaccharide, a monosaccharide, a sugar, a sugar alcohol, a alditol, an organic acid, a phenol, a cresol, ethanediol, ethanedione, acetic acid, propanol, propanediol, propionic acid, glycerol, glyceraldehyde, dihydroxyacetone, lactic acid, pyruvic acid, malonic acid, a butanediol, butanoic acid, an aldotetrose, tartaric acid, an aldopentose, an aldohexose, a ketotetrose, a ketopentose, a ketohexose, a hemicellulose, a cellulosic derivative, a lignocellulosic derivative, and a polyol.

### Claim 16 (depends on 8)

The method of claim 8, wherein the condensation catalyst comprises a member selected from the group consisting of a carbide, a nitride, zirconia, alumina, silica, an aluminosilicate, a phosphate, a zeolite, a titanium oxide, a zinc oxide, a vanadium oxide, a lanthanum oxide, a yttrium oxide, a scandium oxide, a magnesium oxide, a cerium oxide, a barium oxide, a calcium oxide, a hydroxide, a heteropolyacid, an inorganic acid, an acid modified resin, a base modified resin, and combinations thereof.