Solvolysis of biomass to produce aqueous and organic products

Patent metadata

Field	Value
Publication number	US-9587178-B2
Application number	US-201615206900-A
Country	US
Kind code	B2
Filing date	Jul 11, 2016
Priority date	Dec 30, 2010
Publication date	Mar 7, 2017
Grant date	Mar 7, 2017

Abstract

The present invention provides processes for deconstructing biomass to produce aqueous and organic products using a solvent produced in a bioreforming reaction.

First claim

We claim:

1. A method of deconstructing biomass to produce a reaction product, the method comprising:
A. catalytically reacting water and a water-soluble C 2+ O 1+ oxygenated hydrocarbon in a liquid or vapor phase with H2 in the presence of a deoxygenation catalyst at a deoxygenation temperature and a deoxygenation pressure to produce a biomass processing solvent comprising a C 2+ O 1-3 hydrocarbon in a reaction stream; and
B. reacting the biomass processing solvent with a biomass component at a deconstruction temperature and a deconstruction pressure to produce a reaction product, the reaction product comprising a biomass hydrolysate, an organic phase, and a solid phase, wherein the biomass hydrolysate comprises 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 water-soluble lignin derivative, a carbohydrate, a starch, a monosaccharide, a disaccharide, a polysaccharide, a sugar, a sugar alcohol, an alditol, a polyol, and a phenol, and wherein the biomass component is a solid, wood material biomass component comprising two or more members selected from the group consisting of lignin, cellulose, and hemicellulose.

2. The method of claim 1 wherein the organic phase comprises a member selected from the group consisting of 4-ethyl phenol, 4-ethyl-2-methoxy phenol, 2-methoxy-4-propyl phenol, vanillin, 4-propyl syringol, vitamin E, steroids, long chain hydrocarbons, long chain fatty acids, stilbenoids, flavonoids, terpenoids, phenolics, aliphatics, lignans, alkanes, proteinaceous materials, and a combination of two or more of the foregoing.

3. The method of claim 2 wherein the solid phase comprises a residual biomass component and the deoxygenation catalyst.

4. The method of claim 3 further comprising:
C. separating the solid phase from the reaction product;
D. separating the deoxygenation catalyst from the solid phase; and
E. regenerating the deoxygenation catalyst.

5. The method of claim 1 wherein the deoxygenation catalyst comprises a support and a member adhered to the support wherein, the member is selected from the group consisting of Re, Cu, Fe, Ru, Ir, Co, Rh, Pt, Pd, Ni, W, Os, Mo, Ag, Au, an alloy thereof, and a combination of two or more of the foregoing.

6. A method of deconstructing biomass, the method comprising reacting a biomass slurry with a biomass processing solvent comprising a C 2+ O 1-3 hydrocarbon at a deconstruction temperature between about 80° C. and 350° C. and a deconstruction pressure between about 100 psi and 2000 psi to produce a reaction product comprising a biomass hydrolysate, an organic phase, and a solid phase, the biomass hydrolysate comprising at least one member selected from the group consisting of a water-soluble lignocellulose derivative, water-soluble cellulose derivative, water-soluble hemicellulose derivative, water-soluble lignin derivative, carbohydrate, starch, monosaccharide, disaccharide, polysaccharide, sugar, sugar alcohol, alditol, polyol, and phenol, wherein the biomass processing solvent is produced by catalytically reacting in the liquid or vapor phase an aqueous feedstock solution comprising water and a water-soluble oxygenated hydrocarbons comprising a C 2+ O 1+ hydrocarbon with H2 in the presence of a deoxygenation catalyst at a deoxygenation temperature and deoxygenation pressure, and wherein the biomass slurry comprises a solid, wood material biomass component comprising two or more members selected from the group consisting of lignin, cellulose, and hemicellulose.

7. The method of claim 6 wherein the organic phase comprises a member selected from the group consisting of 4-ethyl phenol, 4-ethyl-2-methoxy phenol, 2-methoxy-4-propyl phenol, vanillin, 4-propyl syringol, vitamin E, steroids, long chain hydrocarbons, long chain fatty acids, stilbenoids, flavonoids, terpenoids, phenolics, aliphatics, lignans, alkanes, proteinaceous materials, and a mixture thereof.

8. The method of claim 6 further comprising separating the solid phase from the reaction product, wherein the solid phase comprises a residual biomass component and the deoxygenation catalyst.

9. The method of claim 8 further comprising separating the deoxygenation catalyst from the solid phase.

10. The method of claim 9 further comprising regenerating the deoxygenation catalyst.

11. The method of claim 6 wherein the deoxygenation temperature is between about 80° C. and 350° C. and the deoxygenation pressure is between about 100 and 2000 psi.

12. The method of claim 6 wherein the deoxygenation catalyst comprises a support and a member adhered to the support wherein, the member is selected from the group consisting of Re, Cu, Fe, Ru, Ir, Co, Rh, Pt, Pd, Ni, W, Os, Mo, Ag, Au, an alloy thereof, and a combination thereof.

13. The method of claim 12 wherein the support comprises a member selected from group consisting of a carbon, silica, alumina, zirconia, titania, vanadia, heteropolyacid, kieselguhr, hydroxyapatite, chromia, zeolite, and mixtures thereof.

14. The method of claim 13 , wherein the support is selected from the group consisting of tungstated zirconia, tungsten modified zirconia, tungsten modified alpha-alumina, or tungsten modified theta alumina.

15. The method of claim 6 wherein the H2 comprises at least one of an in situ-generated H2, external H2, or recycled H2.

16. The method of claim 6 , wherein the oxygenated hydrocarbon comprises a member selected from the group consisting of a lignocellulose derivative, a cellulose derivative, a hemicellulose derivative, a lignin derivative, a carbohydrate, a starch, a monosaccharide, a disaccharide, a polysaccharide, a sugar, a sugar alcohol, an alditol, a polyol, and a phenol.

17. The method of claim 6 , wherein the biomass processing solvent comprises a member selected from the group consisting of an alcohol, ketone, aldehyde, cyclic ether, ester, furan, hydroxy carboxylic acid, carboxylic acid, a phenol, and a mixture thereof.

18. The method of claim 17 , wherein the biomass processing solvent comprises a member selected from the group consisting of methanol, ethanol, n-propyl alcohol, isopropyl alcohol, butyl alcohol, pentanol, hexanol, cyclopentanol, cyclohexanol, 2-methylcyclopentanol, a hydroxyketone, a cyclic ketone, acetone, propanone, butanone, pentanone, hexanone, 2-methyl-cyclopentanone, ethylene glycol, 1,3-propanediol, propylene glycol, butanediol, pentanediol, hexanediol, methylglyoxal, butanedione, pentanedione, diketohexane, a hydroxyaldehyde, acetaldehyde, propionaldehyde, butyraldehyde, pentanal, hexanal, formic acid, acetic acid, propionic acid, butanoic acid, pentanoic acid, hexanoic acid, lactic acid, glycerol, furan, tetrahydrofuran, dihydrofuran, 2-furan methanol, 2-methyl-tetrahydrofuran, 2,5-dimethyl-tetrahydrofuran, 2-ethyl-tetrahydrofuran, 2-methyl furan, 2,5-dimethyl furan, 2-ethyl furan, hydroxylmethylfurfural, 3-hydroxytetrahydrofuran, tetrahydro-3-furanol, 5-hydroxymethyl-2(5H)-furanone, dihydro-5-(hydroxymethyl)-2(3H)-furanone, tetrahydro-2-furoic acid, dihydro-5-(hydroxymethyl)-2(3H)-furanone, tetrahydrofurfuryl alcohol, 1-(2-furyl)ethanol, and hydroxymethyltetrahydrofurfural, phenol, 4-methyl-phenol, 2-methoxy-phenol, 4-ethyl-phenol, 4-ethyl-2-methoxy-phenol, 4-propyl-phenol, 4-ethyl-2-methoxy-phenol, 2,6-dimethoxy-phenol, 2-methoxy-4-propyl-phenol, 2-methoxy-3-(2-propenyl)-phenol, 2,6-dimethoxy-4-(2-propenyl)-phenol, isomers thereof, and combinations thereof.

19. The method of claim 1 , wherein the wood materi

Assignees

• Virent Inc

Inventors

• Qiao Ming
• Woods Elizabeth
• Myren Paul
• Cortright Randy
• Connolly Sean

Classifications

• C08H8/00

  Macromolecular compounds derived from lignocellulosic materials {(pretreatment thereof B27N)} · CPC title

• C08H6/00

  Macromolecular compounds derived from lignin, e.g. tannins, humic acids · CPC title

• C10G3/47

  containing platinum group metals or compounds thereof · CPC title

• D21B1/021

  by chemical means · CPC title

• C11B3/006

  by extraction · CPC title