# US 9,434,909 B2 · Renewable diesel and jet fuel from microbial sources

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- Number: US 9,434,909 B2
- Document ID: US9434909B2
- Status: Granted
- Kind: B2
- Application number: 14/184,288
- Filed: 2014-02-19
- Published: 2014-06-19
- Granted: 2016-09-06
- Earliest claimed: 2007-06-01
- Assignees: Solazyme, Inc.
- Applicants: Solazyme, Inc.
- Inventors: Donald E. Trimbur; Chung-Soon Im; Harrison F. Dillon; Anthony G. Day; Scott Franklin; Anna Coragliotti
- Web page: https://patentgrep.com/patent/US9434909B2

## CPC

- C10L 1/026: {for compression ignition}
- 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)
- C12N 1/12: Unicellular algae; Culture media therefor (as new plants A01H13/00)
- C12N 1/32: Processes using, or culture media containing, lower alkanols, i.e. C1 to C6
- C12N 9/0006: {acting on CH-OH groups as donors (1.1)}
- C12N 9/0008: {acting on the aldehyde or oxo group of donors (1.2)}
- C12N 9/1205: {Phosphotransferases with an alcohol group as acceptor (2.7.1), e.g. protein kinases}
- C12N 9/16: acting on ester bonds (3.1)
- C12N 9/20: Triglyceride splitting, e.g. by means of lipase
- C12N 9/2408: {acting on alpha -1,4-glucosidic bonds}
- C12N 9/2431: {Beta-fructofuranosidase (3.2.1.26), i.e. invertase}
- C12N 9/88: Lyases (4.)
- C12N 15/79: Vectors or expression systems specially adapted for eukaryotic hosts
- C12P 5/02: acyclic {(C12P5/007 takes precedence)}
- C12P 7/6409: Fatty acids
- C12P 7/6458: by transesterification, e.g. interesterification, ester interchange, alcoholysis or acidolysis
- C12P 7/6463: obtained from glyceride producing microorganisms, e.g. single cell oil
- C12P 7/649: Biodiesel, i.e. fatty acid alkyl esters
- C12Y 302/01026: Beta-fructofuranosidase (3.2.1.26), i.e. invertase
- C07H 21/04: with deoxyribosyl as saccharide radical
- C10L 1/06: for spark ignition
- C10L 2200/0484: Vegetable or animal oils
- C10L 2270/026: for diesel engines, e.g. automobiles, stationary, marine
- C10L 2270/04: for turbines, planes, power generation
- C12N 9/14: Hydrolases (3)
- C12P 21/06: produced by the hydrolysis of a peptide bond, e.g. hydrolysate products (preparing foodstuffs by protein hydrolysis A23J3/00)
- Y02E 50/10: Biofuels, e.g. bio-diesel
- Y02E 50/30: Fuel from waste, e.g. synthetic alcohol or diesel
- Y02P 20/52: using catalysts, e.g. selective catalysts
- Y02T 50/678: Aviation using fuels of non-fossil origin
- 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
- 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
- C07H: SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS (derivatives of aldonic or saccharic acids C07C, C07D; aldonic acids, saccharic acids C07C59/105, C07C59/285; cyanohydrins C07C255/16; glycals C07D; compounds of unknown constitution C07G; polysaccharides, derivatives thereof C08B; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification C12N15/00; sugar industry C13)
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02T: CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO TRANSPORTATION

## Abstract

The invention provides methods of manufacturing alkanes from triglyceride oils produced through fermentation of oil-bearing microbes. The processes provided herein can utilize a variety of carbohydrate feedstocks including cane bagasse, sugar beet pulp, corn stover, glycerol, corn starch, sorghum, molasses, waste glycerol, and other renewable materials. These processes further comprise hydrotreating, hydrocracking, isomerization, distillation, and other petrochemical processes for use with oil-bearing microbes and products derived therefrom to manufacture fuels. Particular embodiments include the manufacture of ASTM D975 and ASTM D1655 compliant fuels. Genetically engineered microbes provided herein can be used in the manufacture of renewable diesel and renewable jet fuel.

## Claims

### Claim 1

A method for producing renewable diesel, comprising:
(a) providing glycerolipid isolated from a population of microalgae of the genus Prototheca, the population of microalgae heterotrophically cultivated in the presence of sucrose, wherein the microalgae are genetically engineered to express sucrose invertase; and
(b) subjecting the isolated glycerolipid to chemical reactions to generate alkanes, wherein the chemical reactions are selected from the group consisting of hydrodeoxygenation, isomerization, and distillation to remove naptha,
whereby renewable diesel is produced.

### Claim 2 (depends on 1)

The method of claim 1, wherein the microalgae are of the species Prototheca moriformis.

### Claim 3 (depends on 1)

The method of claim 1, wherein the chemical reactions are performed in the presence of a catalyst.

### Claim 4 (depends on 3)

The method of claim 3, wherein the catalyst in the hydrodeoxygenation step contains metals selected from the group consisting of Pd, Pt, Ni, NiMo and CoMo.

### Claim 5 (depends on 3)

The method of claim 3, wherein the catalyst in the hydrodeoxygenation step contains metals selected from the group consisting of NiMo/Al2O3 and CoMo/Al2O3.

### Claim 6 (depends on 3)

The method of claim 3, wherein the catalyst in the isomerization step contains metals selected from the group consisting of SAPO-11, SAPO41, ZSM-22, ZSM-23, ferrierite, Pt, Pd, Ni, Al2O3 and SiO2.

### Claim 7 (depends on 3)

The method of claim 3, wherein the catalyst in the isomerization step contains metals selected from the group consisting of Pt/SAPO-11/ Al2O3, Pt/ZSM-22/ Al2O3, Pt/ZSM-23/ Al2O3, and Pt/SAPO-11/SiO2.

### Claim 8 (depends on 1)

The method of claim 1, wherein the hydrodeoxygenation step is performed at temperatures between 200° C. and 500° C.

### Claim 9 (depends on 1)

The method of claim 1 , wherein the hydrodeoxygenation step is performed at pressures between 20 and 150 bar.

### Claim 10 (depends on 1)

The method of claim 1, wherein the isomerization step is performed at pressures between 20 and 150 bar.

### Claim 11

A method for producing jet fuel, comprising:
(a) providing glycerolipid isolated from a population of cells of the genus Prototheca, the cells heterotrophically cultivated in the presence of sucrose, wherein the cells are genetically engineered to express sucrose invertase; and
(b) subjecting the isolated glycerolipid to one or more chemical reactions selected from the group consisting of cracking, hydrodeoxygenation, isomerization, and distillation to remove naptha, to generate alkanes having a carbon number distribution between about 8 and 16 carbon numbers,
whereby jet fuel is produced.

### Claim 12 (depends on 11)

The method of claim 11, wherein the cells are of the species Prototheca moriformis.

### Claim 13 (depends on 11)

The method of claim 11, wherein the chemical reactions are performed in the presence of a catalyst.

### Claim 14 (depends on 13)

The method of claim 13, wherein the catalyst in the hydrodeoxygenation step contains metals selected from the group consisting of Pd, Pt, Ni, NiMo and CoMo.

### Claim 15 (depends on 13)

The method of claim 13, wherein the catalyst in the hydrodeoxygenation step contains metals selected from the group consisting of NiMo/Al2O3 and CoMo/Al2O3.

### Claim 16 (depends on 13)

The method of claim 13, wherein the catalyst in the isomerization step contains metals selected from the group consisting of SAPO-11, SAPO41, ZSM-22, ZSM-23, ferrierite, Pt, Pd, Ni, Al2O3 and SiO2.

### Claim 17 (depends on 13)

The method of claim 13, wherein the catalyst in the isomerization step contains metals selected from the group consisting of Pt/SAPO-11/ Al2O3, Pt/ZSM-22/ Al2O3, Pt/ZSM-23/ Al2O3, and Pt/SAPO-11/SiO2.

### Claim 18 (depends on 11)

The method of claim 11, wherein the hydrodeoxygenation step is performed at temperatures between 200° C. and 500° C.

### Claim 19 (depends on 11)

The method of claim 11, wherein the hydrodeoxygenation step is performed at pressures between 50 and 100 bar.

### Claim 20 (depends on 11)

The method of claim 11, wherein the isomerization step is performed at pressures between 20 and 100 bar.

### Claim 21

A method for producing jet fuel, comprising:
(a) providing glycerolipid isolated from a population of cells of the genus Prototheca, the cells heterotrophically cultivated in the presence of sucrose, wherein the cells are genetically engineered to express sucrose invertase; and
(b) subjecting the isolated glycerolipid to one or more chemical reactions selected from the group consisting of fluid catalytic cracking, hydrodeoxygenation, isomerization, and distillation to remove naptha, to generate alkanes having a carbon number distribution between about 5 and 15 carbon numbers,
whereby jet fuel is produced.

### Claim 22 (depends on 21)

The method of claim 21, wherein the fluid catalytic cracking occurs in steps selected from the group consisting of:
(a) flowing the glycerolipid through a fluid catalytic cracking reactor zone;
(b) vaporization of the glycerolipid;
(c) contacting the glycerolipid with a cracking catalyst;
(d) discharging the catalyst and glycerolipid vapors;
(e) collecting a product vapor stream comprised of hydrocarbons and catalyst particles; and
(f) separating the catalyst from the product vapor stream.

### Claim 23 (depends on 21)

The method of claim 21, wherein the cells are of the species Prototheca moriformis.

### Claim 24 (depends on 21)

The method of claim 21, wherein the glycerolipid is contacted with a catalyst in a catalyst to lipid ratio of about 5 to about 20.

### Claim 25 (depends on 24)

The method of claim 24, wherein the glycerolipid is contacted with a catalyst in a catalyst to lipid ratio of about 10 to about 15.