Hydroxy fatty acid synthesis

Patent metadata

Field	Value
Publication number	US-11680224-B2
Application number	US-202117519162-A
Country	US
Kind code	B2
Filing date	Nov 4, 2021
Priority date	Nov 4, 2020
Publication date	Jun 20, 2023
Grant date	Jun 20, 2023

Abstract

The invention relates to methods for the synthesis of hydroxy fatty acids from unsaturated fatty acids via epoxidation and catalytic hydrogenation.

First claim

We claim:

1. A method for the synthesis of at least one mono hydroxy fatty acid, the method comprising reacting in a pressurized container at least one epoxidized fatty acid or epoxidized fatty acid ester in a solvent, with an organic acid and a palladium or platinum catalyst in a hydrogen atmosphere to obtain at least one mono hydroxy fatty acid.

2. The method of claim 1 , wherein the at least one epoxidized fatty acid is obtained from sunflower, safflower, tallow, pennycress, crambe , rapeseed, Brassica carinata , meadowfoam, coriander, soybean, camelina, or jojoba.

3. The method of claim 1 , wherein the organic acid is acetic acid, oxalic acid, trifluoroacetic acid, trichloroacetic acid, or tribromoacetic acid.

4. The method of claim 3 , wherein the organic acid is oxalic acid.

5. The method of claim 1 , wherein the catalyst is palladium on carbon or platinum on carbon.

6. The method of claim 5 , wherein the catalyst is palladium on carbon.

7. The method of claim 6 , wherein 1 equivalent of the epoxidized fatty acid is reacted with from about 0.0020 equivalents of palladium to about 0.021 equivalents of palladium.

8. The method of claim 1 , wherein the pressure is at least about 14 psi to at least about 1100 psi.

9. The method of claim 1 , wherein the pressure is at least about 160 psi Hydrogen to at least about 1000 psi hydrogen.

10. The method of claim 1 , wherein the method produces at least one hydroxy fatty acid and at least one ketone fatty acid.

11. The method of claim 10 , wherein less than about 18% of the reaction product is ketone fatty acid.

12. The method of claim 1 , wherein the solvent is not n-butyl propionate containing 1% sulfuric acid; ethanol; petroleum ether containing 1% acetic acid; anhydrous propionic acid; or glacial acetic acid.

13. The method of claim 1 , wherein the solvent is ethyl acetate.

14. The method of claim 1 , wherein the at least one epoxidized fatty acid has more than 7 carbons.

15. The method of claim 1 , wherein the temperature is from about 20° C. to about 180° C.

16. The method of claim 1 , wherein no acetate esters are synthesized.

17. The method of claim 1 , wherein the at least one epoxidized fatty acid is epoxidized methyl oleate, and the hydroxy fatty acid obtained is a 50:50 mixture of methyl 9-hydroxystearate and methyl 10-hydroxystearate.

18. The method of claim 1 , wherein the method further comprises obtaining the epoxidized fatty acid by reacting an unsaturated fat with formic acid and hydrogen peroxide at room temperature and pressure.

Assignees

• Us Agriculture
• The Us Secratery Of Agriculture

Inventors

• Cermak Steven C
• Isbell Terry
• Lowery Benjamin A

Classifications

• C07D303/42

  Acyclic compounds having a chain of seven or more carbon atoms, e.g. epoxidised fats · CPC title

• C11C3/126 Primary

  using catalysts based principally on other metals or derivates · CPC title

• C11C3/006

  by oxidation · CPC title

• C11C3/14

  by isomerisation {(isomerisation induced by hydrogenation C11C3/12)} · CPC title