IP Library Granted Patent US 10,093,638
Granted Patent B2
US 10,093,638 · App. 15/468,728 · Granted Oct 9, 2018

Utilizing a multiphase reactor for the conversion of biomass to produce substituted furans

Inventors: Makoto Nathanael Masuno (Elk Grove, CA); John Bissell, II (Sacramento, CA); Ryan L. Smith (Sacramento, CA); Brian Higgins (Davis, CA); Alex B. Wood (Sacramento, CA)
Assignee: MICROMIDAS, INC.
C07D307/50C07D307/46
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Quick Facts
Patent No.
US 10,093,638
App. No.
15/468,728
Granted
Oct 9, 2018
Kind
B2
Abstract

The present disclosure provides methods to produce substituted furans (e.g., halomethylfurfural, hydroxymethylfurfural, and furfural), by acid-catalyzed conversion of biomass using a gaseous acid in a multiphase reactor, such as a fluidized bed reactor.

Claims (30)

1. A system for producing halomethylfurfural, comprising:

a. a solid feedstock, wherein the solid feedstock comprises biomass, sugar, or a combination thereof;

b. a gaseous acid that has less than about 10% water by weight;

c. a multiphase reactor configured to receive the solid feedstock and the gaseous acid and provide a reaction mixture comprising halomethylfurfural; and

d. a solid-gas separator selected from the group consisting of a cyclone, a filter, and a gravimetric system, wherein the solid-gas separator is configured to receive the reaction mixture of the multiphase reactor and to provide a solid mixture and a separated gaseous acid, and wherein the solid mixture comprises halomethylfurfural.

2. The system of claim 1 , wherein the gaseous acid is hydrochloric acid, hydrofluoric acid, hydrobromic acid, or hydroiodic acid.

3. The system of claim 1 , wherein the halomethylfurfural is 5-(chloromethyl)furfural.

4. The system of claim 1 , wherein the multiphase reactor is a fluidized bed reactor, a plug-flow reactor, an auger system or an agitation system.

5. The system of claim 1 , wherein the multiphase reactor allows for continuous operation.

6. The system of claim 1 , wherein the multiphase reactor allows for batch operation.

7. The system of claim 1 , wherein the solid feedstock is dried and ground before introduction into the multiphase reactor.

8. The system of claim 1 , wherein temperature in the multiphase reactor is between 50° C. and 300° C.

9. The system of claim 1 , wherein the pressure in the multiphase reactor is between 0.1 atm and 50 atm.

10. The system of claim 1 , wherein the reaction mixture comprises between 3% and 8% wt water.

11. The system of claim 1 , wherein the system is configured to combine the reaction mixture with a solvent to provide a mixture comprising a solution comprising halomethylfurfural, and remaining solids.

12. The system of claim 11 , wherein the system is configured to combine the solvent and reaction mixture in line.

13. The system of claim 11 , wherein the solvent is dichloromethane, ethylacetate, hexane, cyclohexane, benzene, toluene, diethyl ether, tetrahydrofuran, acetone, dimethyl formamide, dimethyl sulfoxide, acetonitrile, methanol, ethanol, isopropanol, n-propanol, n-butanol, chloroform, dichloroethane, trichloroethane, furfural, furfuryl alcohol, or supercritical carbon dioxide, or any combination thereof.

14. The system of claim 11 , further comprising a solid-liquid separator, wherein the solid-liquid separator is configured to separate the solution comprising halomethylfurfural from the remaining solids.

15. The system of claim 14 , wherein the solid-liquid separator is a filter system or a membrane system.

16. The system of claim 1 , wherein the multiphase reactor further comprises lithium chloride, sodium chloride, potassium chloride, magnesium chloride, calcium chloride, zinc chloride, aluminum chloride, boron chloride, or any combination thereof.

17. The system of claim 1 , wherein the biomass includes glycans or heteroglycans.

18. The system of claim 17 , wherein the biomass comprises fructose, glucose, or a combination thereof.

19. The system of claim 1 , wherein the feedstock is municipal wastewater, pulp waste, food processing plant waste, restaurant waste, yard waste, forest waste, biodiesel transesterification waste, ethanol process waste, corn stover, rice hulls, rice straw, wheat straw, paper mill effluent, newsprint, municipal solid wastes, wood chips, forest thinnings, slash, miscanthus, switchgrass, sorghum, bagasse, manure, wastewater biosolids, green waste, or food/feed processing residues, or any combination thereof.

20. The system of claim 1 , wherein the multiphase reactor comprises:

a. an inlet configured to receive the solid feedstock;

b. an inlet configured to receive the gaseous acid; and

c. an outlet to provide the reaction mixture.

21. The system of claim 1 , wherein the gaseous acid has between 1% and 10% water by weight.

22. The system of claim 21 , wherein the solid feedstock has between 1% and 10% water by weight.

23. The system of claim 1 , wherein the solid feedstock has between 1% and 10% water by weight.

Assignments (3)
CHANGE OF NAME Recorded Feb 14, 2022
From: MICROMIDAS, INC.
To: ORIGIN MATERIALS OPERATING, INC.
Reel/Frame 059109/0403 →
SECURITY INTEREST Recorded Nov 12, 2019
From: MICROMIDAS, INC,
To: PM OPERATING, LTD.
Reel/Frame 050980/0661 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 26, 2018
From: MASUNO, MAKOTO NATHANAEL; BISSELL, JOHN, II; SMITH, RYAN L.; HIGGINS, BRIAN; WOOD, ALEX B.
To: MICROMIDAS, INC.
Reel/Frame 045727/0293 →
Continuity (4)
Continuation 14805321 · Jul 21, 2015
Continuation 14124240
Provisional Application 61495324 · Jun 9, 2011
Related Publication 20180044311A1 · Feb 15, 2018
Cited By (1)
US 12,281,089