Preparation of furan fatty acids from 5-(chloromethyl)furfural

Patent metadata

Field	Value
Publication number	US-10399953-B2
Application number	US-201615751809-A
Country	US
Kind code	B2
Filing date	Sep 14, 2016
Priority date	Sep 14, 2015
Publication date	Sep 3, 2019
Grant date	Sep 3, 2019

Abstract

The present invention provides methods of making furfural fatty acids from (chloromethyl)furfural. The present invention also provides furfural fatty acids and nutritional supplements that include furfural fatty acids.

First claim

What is claimed is:

1. A method for preparing a compound of Formula I having the structure:

the method comprising:
forming a reaction mixture comprising an aqueous acid and a compound of Formula IV:

under conditions sufficient to form a compound of Formula V:

forming a reaction mixture comprising a phosphonium salt of Formula VI:

and the compound of Formula V, under conditions sufficient to form a compound of Formula (Ia) having the structure:

wherein R 5a , R 5b , and R 5c are each independently selected from the group consisting of H, C 1-18 alkyl, C 2-18 alkenyl, and C 6-12 aryl, and
X 2 is halogen;

forming a reaction mixture comprising formaldehyde or paraformaldehyde, hydrogen bromide, and the compound of Formula (Ia), under conditions sufficient to form a compound of Formula VII:

forming a reaction mixture comprising hydrogen, a hydrogenation catalyst, and the compound of Formula VII under conditions sufficient to form the compound of Formula I,

wherein
R 1 is C 1-18 alkyl;
R 2 and R 3 are methyl groups;
R 4a and R 4b are each independently C 1-18 alkyl; and
m is an integer from 1 to 18.

2. The method of claim 1 , wherein the aqueous acid is hydrochloric acid.

3. The method of claim 1 , wherein m is 8, X 2 is iodine, and R 5a , R 5b , and R 5c are each phenyl.

4. The method of claim 1 , further comprising
forming a reaction mixture comprising hydrogen, a second hydrogenation catalyst, and the compound of Formula Ia having the structure:

under conditions sufficient to form the compound of Formula Ia having the structure:

5. The method of claim 1 , wherein the compound of Formula I has the structure:

6. The method of claim 1 , further comprising:
forming a reaction mixture comprising an alkylating agent with a Formula R 1 ML n , and a compound of Formula III:

under conditions sufficient to form the compound of Formula IV, wherein X 1 is halogen, M is a metal, L is a ligand, and n is an integer from 1 to 3.

7. The method of claim 6 , wherein the alkylating agent has the Formula R 1 MgX 3 , wherein X 3 is halogen.

8. The method of claim 6 , wherein the alkylating agent is ethylmagnesium chloride.

9. The method of claim 6 , wherein X 1 is chlorine.

10. The method of claim 6 , further comprising:
forming a reaction mixture comprising an alcohol and a compound of Formula II:

under conditions sufficient to form the compound of Formula III.

11. The method of claim 10 , wherein the alcohol is butanol.

12. The method of claim 10 , wherein the compound of Formula I has the structure:

Assignees

• Univ California

Inventors

• Mascal Mark
• Chang Fei

Classifications

• A23L33/12

  Fatty acids or derivatives thereof · CPC title

• C07D307/54 Primary

  Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals · CPC title