Lignin-based solvents and methods for their preparation

• US 10,479,773 B2
• Filed: 05/02/2017
• Issued: 11/19/2019
• Est. Priority Date: 05/03/2016
• Status: Active Grant

• Current Assignee: Shell Oil Company (Shell Plc)
• Original Assignee: Shell Oil Company (Shell Plc)
• Inventors: Chheda, Juben Nemchand, Lange, Jean Paul Andre Marie Joseph Ghislain
• Primary Examiner(s): Aulakh, Charanjit
• Application Number:
  US16/173,683
• Publication Number:
  US 20190144409A1
• Time in Patent Office: 931 Days
• Field of Search: 549483
• CPC Class Codes: C07D 307/50 Preparation from natural products
• CPC Class Codes: C07G 1/00 Lignin; Lignin derivatives
• CPC Class Codes: Y02E 50/10 Biofuels, e.g. bio-diesel

Abstract

Implementations of the disclosed subject matter provide a process for converting biomass into furfural. The process may include subjecting a pentosan-containing biomass material to an acid catalyzed digestion process in a digestion vessel to produce a digested product stream comprising C5-carbohydrates and solids comprising cellulose. The digested product stream may be separated into a liquid product stream and a solid product stream comprising lignin and cellulose. The solids product stream may be contacted with water and an organic solvent, thereby converting at least part of the lignin to a phenolic solvent. The C5-carbohydrate in the liquid product stream may be subjected to a dehydration reaction in the presence of an acid catalyst and a biphasic mixture comprising an aqueous phase and a water-immiscible organic phase, wherein the water-immiscible organic phase includes at least a portion of the phenolic solvent, to produce furfural or a furan derivative.

Claims

1. A process for converting biomass into furfural, the process comprising the steps of:

(a) providing a pentosan-containing biomass material;

(b) subjecting the pentosan-containing biomass material to an acid catalyzed digestion process in a digestion vessel at a temperature greater than about 100°

C. for a period of time sufficient to produce a digested product stream comprising C5-carbohydrates and solids comprising cellulose;

(c) separating the digested product stream into a liquid product stream and a solid product stream wherein;

(i) the liquid product stream comprises carbohydrate compounds, of which at least 50 wt % of the carbohydrate compounds are C5-carbohydrate compounds, based on the weight of carbohydrate compounds in the liquid product stream,

(ii) the solid product stream comprises solids comprising lignin and cellulose;

(d) contacting the solid product stream with an organic solvent, thereby converting at least part of the lignin to a phenolic solvent, to produce solids and a solvent product stream comprising the phenolic solvent;

(e) subjecting the C5-carbohydrate in the liquid product stream to a dehydration reaction in a reaction vessel at a temperature in the range of from about 100°

C. to about 250°

C. in the presence of an acid catalyst and a biphasic mixture comprising an aqueous phase and a water-immiscible organic phase, which comprises at least a portion of the phenolic solvent produced in step (d), for a period of time sufficient to produce furfural or a furan derivative;

(f) retrieving from the reaction vessel a dehydration product stream comprising water, organic solvent and furfural, and separating the dehydration product stream into an aqueous recycle stream and an organic product stream comprising furfural;

(g) recovering the furfural from the organic product stream by at least one separation process; and

(h) recycling the organic product stream from step (g) back to the reaction vessel in step (e).

2. The process of claim 1, further comprising, prior to step (e), separating at least part of the phenolic solvent from the solvent product stream produced in step (d), and wherein the phenolic solvent in step (e) is at least a portion of the separated phenolic solvent.

3. The process of claim 1, further comprising:

subjecting at least part of separated the phenolic solvent from step (d) to a catalytic conversion step thereby converting at least part of the separated phenolic solvent to a monomeric phenolic solvent prior to feeding to step (e), and wherein the water-immiscible organic phase in step (e) comprises the monomeric phenolic solvent.

4. The process of claim 3, wherein the catalytic conversion step is selected from the group consisting of:

hydrogenolysis, pyrolysis, base hydrolysis, and a hydrodeoxygenation reaction.

5. The process of claim 1, further comprising, prior to step (e), upgrading the solvent product stream comprising the phenolic solvent in step (d), and wherein the phenolic solvent in step (e) is at least a portion of the upgraded phenolic solvent.

6. The process of claim 1, further comprising recycling the aqueous recycle stream back to the digestion vessel in step (b).

7. The process of claim 1, further comprising, prior to step (e), separating the solids from the solvent product stream of step (d).

8. The process of claim 1, wherein step (d) further comprises contacting the solid product stream with an organic solvent and water.

9. The process of claim 8, wherein water and organic solvent are separated from the solvent product stream in step (d), and further comprising recycling the water and organic solvent to step (d).

10. The process of claim 1, wherein the water-immiscible organic phase in step (e) further comprises the organic solvent used in step (d).