Isolation of Omega-7 fatty acid ethyl esters from natural oils

Patent metadata

Field	Value
Publication number	US-10314871-B2
Application number	US-201815875098-A
Country	US
Kind code	B2
Filing date	Jan 19, 2018
Priority date	Nov 22, 2013
Publication date	Jun 11, 2019
Grant date	Jun 11, 2019

Abstract

Methods of producing high purity palmitoleic acid esters from natural oils are disclosed. The natural oils may comprise plant oil, nut oil, microalgae oil, and fish oil. The methods of processing the natural oil comprise transesterification with ethanol as the reacting solvent to produce ethyl esters. Methods of producing a high purity fraction of Omega-3, 6, & 9 fatty acid esters from natural oils are also disclosed. The high purity fatty acid esters may be used in nutrition, cosmetic, and nutraceutical products.

First claim

What is claimed is:

1. A method of producing high purity palmitoleic acid ethyl esters, comprising:
a. Providing a natural oil;
b. Transesterifying the natural oil with a catalyst and ethanol as a reacting solvent in a reaction comprising at least one stage to produce ethyl esters;
c. Distilling the ethyl esters to produce a first fraction comprising C18:1n9, C20:4n6, and C20:5n3 ethyl esters, and a second fraction comprising C16:0 and C16:1n7 ethyl esters; and
d. Separating the C16:0 and C16:1n7 ethyl esters of the second fraction to produce a third fraction of C16:0 ethyl esters and a fourth fraction comprising at least 50% w/w C16:1n7 ethyl esters.

2. The method of claim 1 , wherein the natural oil consists of a natural oil comprising at least 5% C16:1n7 fatty acid.

3. The method of claim 2 , wherein the natural oil comprises oil derived from at least one source selected from the group consisting of macadamia nut oil, menhaden oil, and anchovy oil.

4. The method of claim 1 , wherein the catalyst of the transesterifying step comprises at least one catalyst selected from the group consisting of: NaOH, KOH, sodium ethoxide, HCl, BF 3 , H 3 PO 4 , an organic sulfonic acid, sulphuric acid, a metal oxide, Mg—Al hydrolalcite, and an immobilized enzyme.

5. The method of claim 1 , wherein the molar ratio of ethanol in the transesterifying step is in the range of 1:3 to 1:15.

6. The method of claim 5 , wherein the molar ratio of ethanol in the transesterifying step is in the range of 1:6 to 1:8.

7. The method of claim 1 , wherein the transesterifying step comprises two stages of transesterification reactions.

8. The method of claim 7 , wherein the two stages of transesterification reactions use different catalysts.

9. The method of claim 1 , wherein the transesterifying step has a yield in the range of 70-90%.

10. The method of claim 1 , wherein the transesterifying step is performed at a temperature in the range of 75-85° C.

11. The method of claim 1 , wherein the distillation step comprises at least one selected from the group consisting of one pass vacuum distillation, two pass vacuum distillation, fractional distillation, and simple molecular distillation.

12. The method of claim 1 , wherein the separation step comprises at least one selected from the group consisting of urea complexation, crystallization, filtration, extraction, and adsorption chromatography.

13. The method of claim 1 , wherein the fourth fraction comprises at least 80% w/w C16:1n7 ethyl esters.

14. The method of claim 3 , wherein the second fraction derived from natural macadamia nut oil comprises less than 20% w/w C16:0 ethyl esters.

15. The method of claim 14 , wherein the fourth fraction derived from natural macadamia nut oil further comprises less than 10% w/w C16:0 ethyl esters.

16. The method of claim 3 , wherein the second fraction derived from natural macadamia nut oil comprises less than 1% w/w C18:1n9 ethyl esters.

17. The method of claim 16 , wherein the fourth fraction derived from natural macadamia nut oil further comprises less than 5% w/w C18:1n9 ethyl esters.

18. The method of claim 3 , wherein the second fraction derived from natural macadamia nut oil further comprises at least 70% w/w of C16:1n7 and C18:1n9 ethyl esters combined.

19. The method of claim 1 , further comprising including the C16:1n7 ethyl esters in a product selected from the group consisting of a nutrition product, cosmetic product, and nutraceutical product.

20. The method of claim 11 , wherein the distillation step is performed at a pressure in the range of 0.3-5 mm Hg and a temperature in the range of 140-280° C.

Assignees

• Heliae Dev Llc

Inventors

• Shinde Sandip
• Ventre Stephen
• Lloyd-Randolfi Jennifer
• Lamont Michael

Classifications

• A61K31/231

  having one or two double bonds · CPC title

• A61Q19/00

  Preparations for care of the skin · CPC title

• C12P7/6454

  by esterification · CPC title

• A61K36/02 Primary

  Algae · CPC title

• A61K8/37

  Esters of carboxylic acids · CPC title