Granted Patent B2

US 12,281,089 · App. 17/687,009 · Granted Apr 22, 2025

Inventors: Alex B. Wood (Sacramento, CA); Makoto N. Masuno (Elk Grove, CA); Ryan L. Smith (Sacramento, CA); John Bissell (West Sacramento, CA); Dimitri A. Hirsch-Weil (Sacramento, CA); Robert Joseph Araiza (Sacramento, CA); Daniel R. Henton (Midland, MI); James H. Plonka (Midland, MI)

Assignee: Origin Materials Operating, Inc.

C07D307/46B01J27/10C07D307/50

Abstract

Claims (48)

1. A method, comprising:

converting a feedstock into 5-(halomethyl)furfural in the presence of (i) H + , (ii) X − , and (iii) a Group I or Group II cation, wherein [H + ] is greater than 0 M and less than or equal to 8 M, and wherein X − is a halo anion.

2. The method of claim 1 , wherein 5-(halomethyl)furfural is produced.

3. The method of claim 1 , wherein one or more products comprising humins, levulinic acid, formic acid, furfural, gamma valerolactone, fulvic acid, or any combinations or mixture thereof is produced.

4. The method of claim 3 , wherein humins are produced.

5. The method of claim 2 , further comprising:

a) combining the feedstock, an aqueous acid, and a salt in a reaction vessel to form a reaction mixture, wherein:

the aqueous acid is a halogen-containing acid; and

the reaction mixture has the [H + ] concentration less than 8 M; and

b) converting at least a portion of the feedstock in the reaction mixture to produce 5-(halomethyl)furfural.

6. The method of claim 2 , further comprising:

a) combining the feedstock, an acid, and a salt in a reaction vessel to form a reaction mixture, wherein:

the acid is HX, wherein X is halo;

the feedstock comprises one or more C6 monosaccharides, or the feedstock is a disaccharide or polysaccharide comprising monomeric units having six carbon atoms;

the salt is LiX or CaX2, or a combination thereof; and the reaction mixture has a [H + ] less than 8 M; and

b) converting at least a portion of the feedstock in the reaction mixture into 5-(halomethyl)furfural.

7. The method of claim 2 , further comprising:

a) combining the feedstock, an acid, and a salt in a reaction vessel to form a reaction mixture, wherein:

the acid is HX, wherein X is halo;

the salt is A r+ (X−) r , wherein:

A r+ is a Group I or Group II cation, r is 1 or 2, and

X − is a halo anion; and

the reaction mixture has the [H + ] greater than 0 M and less than 8 M; and

b) converting at least a portion of the feedstock in the reaction mixture into 5-(halomethyl)furfural.

8. The method of claim 2 , further comprising:

a) combining the feedstock, an acid, and a salt in a reaction vessel to form a reaction mixture, wherein:

the acid is HX, wherein X is halo;

the salt is A r+ (X − ) r , wherein:

A r+ is a Group I or Group II cation, r is 1 or 2, and

X − is a halo anion; and

the reaction mixture has the [H + ] greater than 0 M and less than 8 M; and

the feedstock and the [H + ] is present in the reaction mixture at a molar ratio of 1:1; and

b) converting at least a portion of the feedstock in the reaction mixture into 5-(halomethyl)furfural.

9. The method of claim 2 , further comprising:

a) combining the feedstock, an acid, and a salt in a reaction vessel to form a reaction mixture, wherein:

the acid is HX, wherein X is halo;

the salt is A r+ (X−) r , wherein:

A r+ is a Group I or Group II cation, r is 1 or 2, and

X − is a halo anion; and

the reaction mixture has the [H + ] between 0 M and 5 M; and

b) converting at least a portion of the feedstock in the reaction mixture into 5-(halomethyl)furfural at a temperature of at least 110° C.

10. The method of claim 2 , further comprising:

a) combining the feedstock, an acid, and a salt in a reaction vessel to form a reaction mixture, wherein: the acid is HX, wherein X is halo;

the acid is continuously added; and

the salt is A r+ (X−) r , wherein:

A r+ is a Group I or Group II cation, r is 1 or 2, and

X − is a halo anion; and

b) converting at least a portion of the feedstock in the reaction mixture into 5-(halomethyl)furfural at a temperature of at least 110° C.

Assignments (5)

Continuity (6)

References Cited (162)