Omega 7 rich compositions and methods of isolating omega 7 fatty acids

• US 9,200,236 B2
• Filed: 11/19/2012
• Issued: 12/01/2015
• Est. Priority Date: 11/17/2011
• Status: Active Grant

• Current Assignee: Heliae Development, LLC (PT Perusahaan Perkebunan London Sumatra Indonesia Tbk)
• Original Assignee: Heliae Development, LLC (PT Perusahaan Perkebunan London Sumatra Indonesia Tbk)
• Inventors: Shinde, Sandip, Kale, Aniket, Licamele, Jason D., Tonkovich, Anna Lee, Kulaga, Tom
• Primary Examiner(s): McKelvey, Terry A
• Assistant Examiner(s): Chen, Catheryne
• Application Number:
  US13/680,961
• Publication Number:
  US 20130129775A1
• Time in Patent Office: 1,107 Days
• US Class Current: 1/1
• CPC Class Codes: A23D 9/00 Other edible oils or fats, e.g. shortenings, cooking oils
• CPC Class Codes: A23D 9/02 characterised by the production or working-up
• CPC Class Codes: A23K 20/158 Fatty acids; Fats; Products containing oils or fats
• CPC Class Codes: A23L 33/12 Fatty acids or derivatives thereof
• CPC Class Codes: A61K 8/361 Carboxylic acids having more than seven carbon atoms in an unbroken chain; Salts or anhydrides thereof
• CPC Class Codes: A61K 8/9722 Chlorophycota or Chlorophyta [green algae], e.g. Chlorella
• CPC Class Codes: A61Q 19/00 Preparations for care of the skin
• CPC Class Codes: C07C 1/22 by reduction
• CPC Class Codes: C10G 2300/1014 of vegetal origin
• CPC Class Codes: C10L 1/026 for compression ignition
• CPC Class Codes: C11B 1/10 by extracting
• CPC Class Codes: C11B 3/001 by a combination of two or more of the means hereafter
• CPC Class Codes: C11B 3/006 by extraction
• CPC Class Codes: C11B 3/12 by distillation
• CPC Class Codes: C11B 7/00 Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils
• CPC Class Codes: C11C 3/00 Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom sulfonated fats or oils C07C309/62; factice C08H; drying oils C09F
• 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
• CPC Class Codes: C12N 1/12 Unicellular algae; Culture media therefor as new plants A01H13/00
• CPC Class Codes: C12P 7/6409 Fatty acids
• CPC Class Codes: Y02E 50/10 : Biofuels, e.g. bio-diesel
• CPC Class Codes: Y02P 30/20 : using bio-feedstock

Abstract

Disclosed here are compositions rich in omega-7 fatty acids, including palmitoleic acid, and products rich in omega-7 fatty acids derived from algal biomass. The algae and/or compositions rich in omega-7 fatty acids may be used in products or as ingredients of products. Methods and systems for increasing the production or concentration of omega-7 fatty acids, and isolating omega-7 fatty acids from algal biomass are also disclosed herein.

Claims

1. A method of isolating an omega-7 fatty acid ester from algal biomass, comprising the steps of:

(a) Extracting oil from algal biomass comprising C16;

1 fatty acids;

(b) Transesterifying the extracted oil to generate a first algal extract mixture;

(c) Decanting the first algal extract mixture to separate a second algal extract fraction and a fraction comprising glycerine and water;

(d) A first distilling of the second algal extract fraction to separate a third algal extract fraction and a fraction comprising carotenoids, chlorophylls, and unesterified material;

(e) A second distilling of the third algal extract fraction to separate a fraction rich in omega-7 esters and a fraction rich in eicosapentaenoic acid (EPA) esters; and

(f) Isolating the fraction rich in omega-7 esters from the fraction rich in EPA esters.

2. The method of claim 1, further comprising:

degumming the extracted oil.

3. The method of claim 1, further comprising:

hydrodeoxygenating the fraction rich in omega-7 esters to generate an algae green diesel fraction.

4. The method of claim 3, further comprising:

isomerizing the algae green diesel fraction to generate an algae jet fuel fraction.

5. The method of claim 1, wherein the first distilling step is a molecular distillation.

6. A method of isolating an omega-7 fatty acid ester from algal biomass, comprising the steps of:

(a) Extracting oil from algal biomass comprising C16;

1 fatty acids;

(b) Adding a solvent to the extracted oil to generate a first algal extract mixture;

(c) Transesterifying the first algal extract mixture to generate a second algal extract mixture;

(d) Decanting the second algal extract mixture to separate a third algal extract fraction and a fraction comprising glycerine and water;

(e) A first distilling of the third algal extract fraction to separate a fourth algal extract fraction and a fraction comprising carotenoids, chlorophylls, and unesterified material;

(f) A second distilling of the fourth algal extract fraction to separate a first fraction rich in omega-7 esters and a fraction rich in eicosapentaenoic acid (EPA) esters; and

(g) Isolating the first fraction rich in omega-7 esters from the fraction rich in EPA esters.

7. The method of claim 6, further comprising:

(a) Crystallizing the first fraction rich in omega-7 esters to separate a second fraction rich in omega-7 and a fraction rich in saturated biodiesel esters.

8. The method of claim 6, further comprising:

(a) Separating the first fraction rich in omega-7 esters using supercritical fluid chromatography into a second fraction rich in omega-7 and a fraction rich in saturated biodiesel esters.

9. The method of claim 6, further comprising:

(a) Transesterifying the fraction rich in EPA esters to generate EPA monoglyceride.

10. The method of claim 6, wherein the first distilling step is a molecular distillation.

11. A method of producing alkanes from an algal oil, comprising the steps of:

(a) Extracting oil from algal biomass;

(b) Mixing the extracted oil with a solvent and heating in a solvent extraction process to generate a first algal extract fraction and a water soluble fraction;

(c) Separating the first algal extract fraction and the water soluble fraction;

(d) Degumming the first algal extract fraction with acid and heat to generate a second algal extract fraction and a fraction comprising lecithin, metals and glycolipids;

(e) Separating the second algal extract fraction and the fraction comprising lecithin, metals and glycolipids;

(f) Adsorption of the second algal extract fraction with a solvent wash to generate a third algal extract fraction and a fraction comprising carotenoids and chlorophylls;

(g) Separating the third algal extract fraction and the fraction comprising carotenoids and chlorophylls;

(h) Crystallizing the third algal extract fraction with chilling to separate a fraction rich in EPA and a fraction rich in saturated oils; and

(i) Hydrotreating the fraction rich in saturated oils to generate alkanes.