IP Library Granted Patent US 9,970,034
Granted Patent B2
US 9,970,034 · App. 14/599,460 · Granted May 15, 2018

Use of marine algae for co-producing alkenones, alkenone derivatives, and co-products

Inventors: Christopher M. Reddy (Woods Hole, MA); Gregory W. O'Neil (Bellingham, MA); Scott R. Lindell (Woods Hole, MA)
Assignees: Woods Hole Oceanographic Institution; Western Washington University; Marine Biological Laboratory
C12P7/649C07D303/32C12N1/12C12P7/26Y02E50/13
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Quick Facts
Patent No.
US 9,970,034
App. No.
14/599,460
Granted
May 15, 2018
Kind
B2
Abstract

A method comprising a series of selective extraction techniques for the parallel production of biodiesel and isolation of several valuable co-products including an alkenone hydrocarbon mixture of the kerosene/jet fuel range (primarily C10-, C12-, and C17-hydrocarbons) and fucoxanthin, a high-valued carotenoid, from the marine alkenone-producing microalgae Isochrysis.

Claims (16)

1. A method of isolating from algae, an algal biomass and a biofuel oil, each comprising at least one product, comprising the steps of

(a) growing an algal mariculture capable of producing alkenones and a co-product;

(b) extracting the algal culture with a non-polar liquid hydrocarbon solvent comprising one or more alkanes having from 1 to 22 carbons to produce an extraction mixture;

(c) separating the extraction mixture into an algal biomass fraction and a biofuel oil fraction which comprises alkenones; and

(d) isolating the alkenones from the biofuel oil fraction and a co-product from the algal biomass-fraction.

2. The method of claim 1 , wherein substantially pure alkenones are isolated in step (d) by combining the biofuel oil fraction with a polar or partially polar solvent selected from one or more of chloromethane, dichloromethane, dichloroethane, tetrahydrofuran, dimethylformamide, acetonitrile, nitromethane, propylene carbonate, formic acid, butanol, isopropanol, methyltetrahydrofuran, trifluoromethylbenzene, ethyl acetate, ethyl ether, acetone, dimethyl sulfoxide, alcohols, acetic acid, esters, ethers.

3. The method of claim 2 , wherein the alkenones are recrystallized in a solvent selected from one or more of dichloromethane, dichloroethane, chloromethane, toluene, tetrahydrofuran, dimethylether, diethyl ether, methyl-tert-butyl ether, n-hexanes methyltetrahydrofuran, or acetonitrile.

4. The method of claim 1 , wherein the algal culture comprises an algal family selected from one or more of the Isochrysis family, the Emiliania family, and the Gephyrocapsa family.

5. The method of claim 4 , wherein the algal culture comprises an algal species selected from one or more of Isochrysis galbana, Isochrysis species T-Iso, Isochrysis species C-Iso, Isochrysis litoralis, Isochrysis maritime, Emiliania huxleyi , or Gephyrocapsa oceanica.

6. The method of claim 1 , further comprising harvesting and drying the algal mariculture of step (a) by lyophilization, evaporation with or without the addition of solvents, vacuum drying, drum drying, hot air exposure, dielectric drying, supercritical drying, natural air drying, or a combination thereof.

7. The method of claim 1 , wherein the non-polar liquid hydrocarbon solvent contains no fatty acids or fatty acid derivatives, and wherein the extraction mixture of step (b) is subjected to evaporation prior to step (c).

8. The method of claim 1 , wherein the isolated alkenones are chemically modified by a cross metathesis reaction to produce alkenone derivatives.

9. The method of claim 8 , wherein the alkenones are chemically modified by an alkenolysis reaction to produce alkenone derivatives.

10. The method of claim 8 , wherein the alkenones are chemically modified by a butenolysis reaction to produce alkenone derivatives.

11. The method of claim 8 , wherein the isolated alkenone derivatives comprise from 5 to 20 carbon atoms.

12. The method of claim 1 , wherein the non-polar liquid hydrocarbon solvent comprising one or more alkanes having from 1 to 22 carbons is selected from benzene, toluene, cyclohexane, chloroform, ether, 1,4-dioxane, n-hexane, pentane, cyclopentane, iso-hexane, n-heptane, iso-heptane, octane, iso-octane, a neutral surfactant, a nonionic surfactant, or a combination thereof.

Assignments (4)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 16, 2017
From: LINDELL, SCOTT R.
To: MARINE BIOLOGICAL LABORATORY
Reel/Frame 044153/0186 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 23, 2016
From: REDDY, CHRISTOPHER M.
To: WOODS HOLE OCEANOGRAPHIC INSTITUTION
Reel/Frame 038688/0313 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 20, 2016
From: O'NEIL, GREGORY W.
To: WESTERN WASHINGTON UNIVERSITY
Reel/Frame 038661/0583 →
CONFIRMATORY LICENSE Recorded Nov 20, 2015
From: WOODS HOLE OCEANOGRAPHIC INSTITUTE
To: NATIONAL SCIENCE FOUNDATION
Reel/Frame 037151/0148 →
Continuity (6)
Continuation In Part 14187929 · Feb 24, 2014
Continuation In Part 13298576 · Nov 17, 2011
Continuation In Part 12967478 · Dec 14, 2010
Provisional Application 61414491 · Nov 17, 2010
Provisional Application 61287585 · Dec 17, 2009
Related Publication 20150140619A1 · May 21, 2015