IP Library › Granted Patent US 9,908,862

Granted Patent B2

US 9,908,862 · App. 14/912,052 · Granted Mar 6, 2018

Methods of producing alkylfurans

Inventors: Dimitri A. Hirsch-Weil (Sacramento, CA); Makoto N. Masuno (Elk Grove, CA); John Bissell (Sacramento, CA); Dennis A. Hucul (Midland, MI); Alex B. Wood (Sacramento, CA); Robert Joseph Araiza (Sacramento, CA); Daniel R. Henton (Midland, MI)

Assignee: MICROMIDAS, INC.

C07D307/36 C07D307/34

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Quick Facts

Patent No.: US 9,908,862
App. No.: 14/912,052
Granted: Mar 6, 2018
Kind: B2

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Abstract

Provided herein are methods of producing dialkylfurans, such as 2,5-dimethylfuran, and other alkyl furans, such as 2-methylfuran. For example, 2,5-dimethylfuran may be produced by reducing (5-methylfuran-2-yl)methanol or 2-(chloromethyl)-5-methylfuran.

Claims (104)

1. A method of producing a compound of formula (I′):

wherein:

R 1′ is C m alkyl, wherein m is an integer greater than or equal to 0, provided that when m is 0, R 1′ is H; and

R 2′ is C n alkyl, wherein n is an integer greater than or equal to 1,

the method comprising converting a compound of formula (A) to the compound of formula (I′) in the presence of hydrogen, a catalyst and a reagent of formula (i), (ii) or (iii), or any combination thereof,

wherein:

the compound of formula (A) is:

wherein:

R 1a is C m alkyl, or —(CH 2 ) m Y, wherein:

m is as defined for formula (I′), provided that when m is 0, R 1a is H; and

Y is halo; and

R 2a is —(CH 2 ) n-1 CH(O), —(CH 2 ) n OH, or —(CH 2 ) n X, wherein:

n is as defined for formula (I′); and

X is halo; and

the reagent of formula (i) is:

wherein:

each R a , R b and R c is independently H, aliphatic, aryl, or heteroaryl; or

R a and R b are taken together with the nitrogen atoms to which they are connected to form a cyclic moiety having at least 3 ring atoms; provided that when R c is H or methyl, then one of R a and R b is other than methyl; and

the reagent of formula (ii) is:

wherein:

(A) each R a , R b , R c and R d is independently H, aliphatic, aryl or heteroaryl; or

(B) R a and R b are taken together with the nitrogen atoms to which they are connected to form a cyclic moiety having at least 3 ring atoms; and each R c and R d is independently H, aliphatic, aryl or heteroaryl; or

(C) each R a and R b is independently H, aliphatic, aryl or heteroaryl; and R c and R d are taken together with the nitrogen atoms to which they are connected to form a cyclic moiety having at least 3 ring atoms; or

(D) R a and R b are taken together with the nitrogen atoms to which they are connected to form a cyclic moiety having at least 3 ring atoms; and R c and R d are taken together with the nitrogen atoms to which they are connected to form a cyclic moiety having at least 3 ring atoms; or

(E) each R a and R c is independently H, aliphatic, aryl or heteroaryl; and R b and R d are taken together with the nitrogen atoms to which they are connected to form a cyclic moiety having at least 5 ring atoms; or

(F) each R b and R d is independently H, aliphatic, aryl or heteroaryl; and R a and R c are taken together with the nitrogen atoms to which they are connected to form a cyclic moiety having at least 5 ring atoms; and

the reagent of formula (iii) is:

wherein:

each R a and R c is independently H, aliphatic, aryl or heteroaryl; and

t is an integer greater than or equal to 0.

2. The method of claim 1 , wherein the compound of formula (I′) is a compound of formula (I-a) or (I-b):

wherein R 1′ is C m alkyl, wherein m is an integer greater than or equal to 1.

3. The method of claim 1 , wherein the compound of formula (I′) is

4. The method of claim 1 , wherein the compound of formula (A) is a compound of formula (A-i) or (A-ii):

wherein m is an integer greater than or equal to 1.

5. The method of claim 1 , wherein R 1a is C m alkyl.

6. The method of claim 1 , wherein R 1a is —(CH 2 ) m Y.

7. The method of claim 1 , wherein R 2a is —(CH 2 ) n-1 CH(O).

8. The method of claim 1 , wherein R 2a is —(CH 2 ) n OH.

9. The method of claim 1 , wherein R 2a is —(CH 2 ) n X.

10. The method of claim 1 , wherein the compound of formula (A) is

11. The method of claim 1 , wherein the compound of formula (A) is:

wherein:

R 1a is —(CH 2 ) m Y, wherein:

m is an integer greater than or equal to 1; and

Y is halo; and

R 2a is —(CH 2 ) n-1 CH(O), wherein: