Conversion of saponifiable lipids into fatty esters

• US 8,569,530 B2
• Filed: 04/01/2011
• Issued: 10/29/2013
• Est. Priority Date: 04/01/2011
• Status: Expired due to Fees

• Current Assignee: Aurora Algae, Incorporated (Reliance Industries Limited)
• Original Assignee: Aurora Algae, Incorporated (Reliance Industries Limited)
• Inventors: Hippler, Jeffrey G., Thompson, Andy, Dulatas, Lea, Kapicak, Louis A.
• Primary Examiner(s): Carr, Deborah D
• Application Number:
  US13/078,889
• Publication Number:
  US 20110313181A1
• Time in Patent Office: 942 Days
• Field of Search: 554/170, 435/134
• US Class Current: 554/170
• CPC Class Codes: C11C 1/025 by saponification and release of fatty acids
• CPC Class Codes: C11C 3/003 by esterification of fatty acids with alcohols C11C3/02 takes precedence
• CPC Class Codes: C11C 3/02 by esterification of fatty acids with glycerol

Abstract

Various embodiments of the present invention are directed to processes and methods for converting lipids comprising fatty acids into fatty esters. According to various embodiments of the invention, the saponifiable lipids are reacted with a base to form alkali soaps. The alkali soaps are then reacted with an acid to form fatty esters. Both the base reaction and the acid reaction may occur in the presence of one or more alcohols. Following the acid reaction, a solvent may be added to effect a separation of the fatty esters, which may then be recovered.

Claims

1. A method of converting saponifiable lipids into fatty esters, comprising:

reacting the lipids with a base in presence of a first alcohol to form alkali soaps; and

reacting the alkali soaps with an acid in the presence of a second alcohol to form fatty esters; and

wherein at least a portion of the lipids is derived from algal oils.

2. The method of claim 1, wherein the saponifiable lipids are fatty acids which are either free fatty acids or are ester-linked to a sterol or a glycerol backbone.

3. The method of claim 1, wherein at least a portion of the algal oil is produced from the algal species Amphora, Anabaena, Anikstrodesmis, Botryococcus, Chaetoceros, Chlorella, Chlorococcum, Cyclotella, Cylindrotheca, Dunaliella, Emiliana, Euglena, Glossomastix, Hematococcus, Isochrysis, Monochrysis, Monoraphidium, Nannochloris, Nannochloropsis, Navicula, Nephrochloris, Nephroselmis, Nitzschia, Nodularia, Nostoc, Oochromonas, Oocystis, Oscillartoria, Pavlova, Phaeodactylum, Picochloris, Platymonas, Pleurochrysis, Porhyra, Pseudoanabaena, Pyramimonas, Scenedesmus, Stichococcus, Synechococcus, Synechocystis, Tetraselmis, Thalassiosira, or Trichodesmium.

4. The method of claim 1, further comprising maintaining a reaction temperature between about 30°

C. and about 140°

C.

5. The method of claim 1, wherein at least one of the first alcohol and the second alcohol is comprised of more than one alcohol.

6. The method of claim 1, wherein both the first alcohol and the second alcohol are methanol.

7. The method of claim 1, further comprising mixing the base with the first alcohol prior to the lipids'"'"' reaction and mixing the acid with the second alcohol prior to the alkali soaps'"'"' reaction.

8. The method of claim 1, wherein an amount of the first alcohol is between about 0.25 times and about 10 times a weight of the lipids.

9. The method of claim 1, further comprising:

adding a non-polar solvent to produce a polar phase and a non-polar phase, whereby the fatty esters are contained predominantly in the non-polar phase;

separating the polar phase and the non-polar phase; and

separating the fatty acid alkyl esters and the non-polar solvent from the non-polar phase.

10. The method of claim 9, wherein the non-polar solvent is hexane.

11. The method of claim 1, wherein the base is a methoxide.

12. The method of claim 1, wherein the acid is a mineral acid.

13. The method of claim 1, wherein the acid is selected from the group consisting of sulfuric acid, hydrochloric acid, nitric acid, boric acid, hydrofluoric acid, hydrobromic acid, perchloric acid, hydroiodic acid and mixtures thereof.

14. A method for converting saponifiable lipids into fatty esters, comprising:

adding a predetermined amount of saponifiable lipids to a reaction vessel;

in presence of a first alcohol, adding an amount of base sufficient to convert the lipids to alkali soaps;

adding a catalytic excess of the base equal to about 0.25 percent to about 5 percent of a total weight of the lipids, the stoichiometric amount of the base, and the first alcohol;

in presence of a second alcohol, adding a stoichiometric amount of an acid to neutralize excess base and to convert the alkali soaps to fatty acids; and

adding a catalytic excess of the acid equal to about 0.5 percent to about 5 percent of a total weight of the lipids, the stoichiometric amount of the base, the catalytic excess of the base, and the first and second alcohols; and

wherein at least a portion of the lipids is derived from algal oils.

15. The method of claim 14, wherein a total amount of the first alcohol and the second alcohol is between about 0.25 times and about 10 times the weight of the lipids.

16. The method of claim 14, wherein the first alcohol and the second alcohol are the same.

17. The method of claim 14, wherein the base is sodium methoxide or potassium methoxide, and the acid is sulfuric acid or hydrochloric acid.

18. The method of claim 14, further comprising maintaining an amount of water in the reaction vessel to less than 3 percent by weight of the lipids.

19. A method for converting saponifiable lipids into fatty esters, comprising:

determining a composition of the lipids;

adding a predetermined weight of lipids to a reaction vessel;

adding a base and a predetermined amount of an alcohol to the reaction vessel to form alkali soaps, the predetermined amount of the alcohol based on the composition of the lipids; and

adding an acid to the reaction vessel to convert the alkali soaps to fatty esters; and

wherein at least a portion of the lipids is derived from algal oils.