# US 10,246,641 B2 · Processes for producing hydrocarbon products

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- Number: US 10,246,641 B2
- Document ID: US10246641B2
- Status: Granted
- Kind: B2
- Application number: 15/332,654
- Filed: 2016-10-24
- Published: 2017-02-09
- Granted: 2019-04-02
- Earliest claimed: 2011-12-27
- Assignees: Commonwealth Scientific and Industrial Research Organisation
- Applicants: Commonwealth Scientific and Industrial Research Organisation
- Inventors: Thomas Vanhercke; James Robertson Petrie; Anna El Tahchy; Surinder Singh; Qing Liu
- Web page: https://patentgrep.com/patent/US10246641B2

## CPC

- C10B 53/02: of cellulose-containing material (production of pyroligneous acid C10C5/00)
- C01B 3/22: by decomposition of gaseous or liquid organic compounds
- C01B 32/40: Carbon monoxide
- C07C 67/48: Separation; Purification; Stabilisation; Use of additives
- C07K 14/415: from plants
- C10G 2/00: Production of liquid hydrocarbon mixtures of undefined composition from oxides of carbon
- C10G 2/30: {from carbon monoxide with hydrogen}
- C10J 3/82: Gas withdrawal means
- C10L 1/02: essentially based on components consisting of carbon, hydrogen, and oxygen only
- C10L 1/026: {for compression ignition}
- C10L 1/19: Esters {ester radical containing compounds; ester ethers; carbonic acid esters (C10L1/1802, C10L1/1805, C10L1/1808, C10L1/1811, C10L1/1814, C10L1/1817 take precedence)}
- C10L 5/44: on vegetable substances
- C11B 1/00: Production of fats or fatty oils from raw materials
- C11B 1/10: by extracting
- C11B 3/001: {by a combination of two or more of the means hereafter}
- C11B 3/006: {by extraction}
- C11B 3/10: by adsorption
- C11B 3/14: with the use of indifferent gases or vapours, e.g. steam
- C11B 7/0075: {by differences of melting or solidifying points}
- C11C 3/003: {by esterification of fatty acids with alcohols (C11C3/02 takes precedence)}
- C12N 9/1051: {Hexosyltransferases (2.4.1)}
- C12N 15/8218: {Antisense, co-suppression, viral induced gene silencing [VIGS], post-transcriptional induced gene silencing [PTGS]}
- C12N 15/8247: {involving modified lipid metabolism, e.g. seed oil composition}
- C12P 7/6463: obtained from glyceride producing microorganisms, e.g. single cell oil
- C12Y 204/01101: Alpha-1,3-mannosyl-glycoprotein 2-beta-N-acetylglucosaminyltransferase (2.4.1.101)
- C01B 2203/1211: Organic compounds or organic mixtures used in the process for making hydrogen or synthesis gas
- C10J 2300/0906: Physical processes, e.g. shredding, comminuting, chopping, sorting
- C10J 2300/0916: Biomass
- C10J 2300/1659: to liquid hydrocarbons
- C10J 2300/1846: Partial oxidation, i.e. injection of air or oxygen only
- C10L 2200/0469: Renewables or materials of biological origin
- C10L 2200/0476: Biodiesel, i.e. defined lower alkyl esters of fatty acids first generation biodiesel
- C10L 2200/0492: Fischer-Tropsch products
- C10L 2270/026: for diesel engines, e.g. automobiles, stationary, marine
- C10L 2290/02: Combustion or pyrolysis
- C10L 2290/04: Gasification
- C10L 2290/06: Heat exchange, direct or indirect
- C10L 2290/26: Composting, fermenting or anaerobic digestion fuel components or materials from which fuels are prepared
- C10L 2290/28: Cutting, disintegrating, shredding or grinding
- C10L 2290/30: Pressing, compressing or compacting
- C10L 2290/42: Fischer-Tropsch steps
- C10L 2290/544: Extraction for separating fractions, components or impurities during preparation or upgrading of a fuel
- Y02E 20/16: Combined cycle power plant [CCPP], or combined cycle gas turbine [CCGT]
- Y02E 20/18: Integrated gasification combined cycle [IGCC], e.g. combined with carbon capture and storage [CCS]
- Y02E 50/10: Biofuels, e.g. bio-diesel
- Y02E 50/30: Fuel from waste, e.g. synthetic alcohol or diesel
- C10B: DESTRUCTIVE DISTILLATION OF CARBONACEOUS MATERIALS FOR PRODUCTION OF GAS, COKE, TAR, OR SIMILAR MATERIALS (cracking oils C10G; underground gasification of minerals E21B43/295)
- C01B: NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; {METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C}
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07K: PEPTIDES (peptides in foodstuffs A23; obtaining protein compositions for foodstuffs, working-up proteins for foodstuffs A23J; preparations for medicinal purposes A61K; peptides containing beta-lactam rings C07D; cyclic dipeptides not having in their molecule any other peptide link than those which form their ring, e.g. piperazine-2,5-diones, C07D; ergot alkaloids of the cyclic peptide type C07D519/02; macromolecular compounds having statistically distributed amino acid units in their molecules, i.e. when the preparation does not provide for a specific; but for a random sequence of the amino acid units, homopolyamides and block copolyamides derived from amino acids C08G69/00; macromolecular products derived from proteins C08H1/00; preparation of glue or gelatine C09H; single cell proteins, enzymes C12N; genetic engineering processes for obtaining peptides C12N15/00; compositions for measuring or testing processes involving enzymes C12Q; investigation or analysis of biological material G01N33/00)
- C10G: CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION (cracking to hydrogen or synthesis gas C01B; cracking or pyrolysis of hydrocarbon gases to individual hydrocarbons or mixtures thereof of definite or specified constitution C07C; cracking to cokes C10B); RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10J: PRODUCTION OF PRODUCER GAS, WATER-GAS, SYNTHESIS GAS FROM SOLID CARBONACEOUS MATERIAL, OR MIXTURES CONTAINING THESE GASES (synthesis gas from liquid or gaseous hydrocarbons C01B; underground gasification of minerals E21B43/295); CARBURETTING AIR OR OTHER GASES
- C10L: FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
- C11B: PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES (drying-oils C09F)
- C11C: FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C12N: MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA (microbiological testing media C12Q1/00)
- C12P: FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE {(brewing of beer C12C; producing vinegar C12J; producing specific peptides or proteins C07K; producing enzymes C12N9/00; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification C12N15/00; measuring or testing processes involving enzymes or microorganisms C12Q; measuring or testing processes involving nucleic acid amplification reactions C12Q1/6844; fermentation processes to form a food composition, A21 or A23; compounds in general, see the relevant compound class, e.g. C01, C07)}
- C12Y: ENZYMES
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION

## Abstract

The present invention relates to processes for producing industrial products such as hydrocarbon products from non-polar lipids in a vegetative plant part. Preferred industrial products include alkyl esters which may be blended with petroleum based fuels.

## Claims

### Claim 1

A process for producing extracted plant lipid, the process comprising the steps of:
i) extracting lipid from a collection of transgenic vegetative plant parts having a total non-polar lipid content of at least 10% (w/w dry weight); and
ii) recovering the extracted lipid.

### Claim 2 (depends on 1)

The process of claim 1, wherein the step of extracting the lipid comprises one or more rolling, pressing, crushing or grinding the vegetative plant parts.

### Claim 3 (depends on 1)

The process of claim 1, further comprising a step of converting the extracted lipid to an industrial product by applying heat, chemical means, or enzymatic means, or any combination thereof to the extracted lipid.

### Claim 4 (depends on 3)

The process of claim 3, in which at least some of the lipid is converted to the industrial product by chemical means, wherein i) the chemical means comprises reacting the non-polar lipid with an alcohol, optionally in the presence of a catalyst, to produce alkyl esters, and ii) optionally, blending the alkyl esters of step i) with petroleum based fuel.

### Claim 5 (depends on 1)

The process of claim 1, wherein step (i) uses an organic solvent.

### Claim 6 (depends on 5)

The process of claim 5, wherein the organic solvent comprises hexane, diethyl ether, petroleum ether, chloroform/methanol, butanol or benzene.

### Claim 7 (depends on 1)

The process of claim 1 which comprises one or more or all of:
a) recovering the extracted lipid by collecting it in a container,
b) one or more of degumming, deodorising, decolourising, drying or fractionating the extracted lipid,
c) removing at least some waxes and/or wax esters from the extracted lipid, and
d) analysing the fatty acid composition of the extracted lipid.

### Claim 8 (depends on 1)

The process of claim 1, wherein the vegetative plant parts are plant leaves.

### Claim 9 (depends on 1)

The process of claim 1, wherein the vegetative plant parts have one or more or all of the following features:
the total fatty acid content in the non-polar lipid in the vegetative plant parts comprises 19% oleic acid,
the total fatty acid content in the non-polar lipid in the vegetative plant parts comprises 20% palmitic acid,
the total fatty acid content in the non-polar lipid in the vegetative plant parts comprises 15% linoleic acid, and
the total fatty acid content in the non-polar lipid in the vegetative plant parts comprises less than 15% α-linoleic acid.

### Claim 10 (depends on 1)

The process of claim 1, wherein the total fatty acid content in the non-polar lipid in the vegetative plant parts comprises 19% oleic acid.

### Claim 11 (depends on 10)

The process of claim 10, wherein the vegetative plant parts are plant leaves.

### Claim 12 (depends on 1)

The process of claim 1, wherein the vegetative plant parts have a total non-polar lipid content of about 11% (w/w dry weight).

### Claim 13 (depends on 1)

The process of claim 1, wherein the vegetative plant parts have a total non-polar lipid content of about 15% (w/w dry weight).

### Claim 14 (depends on 13)

The process of claim 13, wherein the vegetative plant parts are plant leaves.

### Claim 15 (depends on 11)

The process of claim 11, wherein the vegetative plant parts comprise a total TAG content of about 11% (w/w dry weight).

### Claim 16 (depends on 1)

The process of claim 1, wherein the total fatty acid content in the non-polar lipid of the vegetative plant parts comprises 2% more oleic acid than the non-polar lipid in a corresponding wild-type vegetative plant part.

### Claim 17 (depends on 1)

The process of claim 1, wherein the total fatty acid content in the non-polar lipid of the vegetative plant parts comprises 2% less palmitic acid than the non-polar lipid in a corresponding wild-type vegetative plant part.

### Claim 18 (depends on 1)

The process of claim 1, wherein the non-polar lipid of the vegetative plant parts comprises a modified level of total sterols, non-esterified sterols, steroyl esters or steroyl glycosides relative to the non-polar lipid in a corresponding wild-type vegetative plant part.

### Claim 19 (depends on 2)

The process of claim 2 which comprises a step of harvesting the vegetative plant parts from plants grown in the field with a mechanical harvester.

### Claim 20 (depends on 19)

The process of claim 19, wherein the vegetative plant parts are harvested from the plants at a time between about the time of flowering of the plants to about the time senescence of the plants has started.

### Claim 21 (depends on 1)

A process for producing a feedstuff, the process comprising admixing the extracted plant lipid produced in claim 1 with at least one other food ingredient.