High yield jet fuel and chemicals from ozonolysis of triglycerides

Patent metadata

Field	Value
Publication number	US-11845903-B2
Application number	US-202217930468-A
Country	US
Kind code	B2
Filing date	Sep 8, 2022
Priority date	Nov 2, 2021
Publication date	Dec 19, 2023
Grant date	Dec 19, 2023

Abstract

A method for producing jet range hydrocarbons may include reacting at least a portion a fatty acid stream comprising C18:1 free fatty acid with ozone in an ozonolysis unit to form at least a C18:1 ozonide intermediate; introducing the C18:1 ozonide intermediate into a reactor, wherein at least a portion of the C18:1 ozonide intermediate is reacted with a reductive agent to produce oxidized products comprising azelaic acid and nonanoic acid; and introducing the oxidized products into a hydrotreating unit, wherein at least a portion of the oxidized products is hydrotreated to produce a paraffin product comprising nonane.

First claim

What is claimed is:

1. A method for producing jet range hydrocarbons comprising:
hydrolyzing a triglyceride stream to produce a fatty acid stream comprising free fatty acid;
introducing the fatty acid stream into a distillation column and separating a C18 and heavier cut comprising C18 fatty acids from the fatty acid stream;
reacting at least a portion the C18 and heavier cut comprising C18:1 free fatty acid with ozone in an ozonolysis unit to form at least a C18:1 ozonide intermediate;
introducing the C18:1 ozonide intermediate into a reactor, wherein at least a portion of the C18:1 ozonide intermediate is reacted with a reductive agent to produce oxidized products comprising azelaic acid and nonanoic acid; and
introducing the oxidized products into a hydrotreating unit, wherein at least a portion of the oxidized products is hydrotreated to produce a paraffin product comprising nonane.

2. The method of claim 1 , wherein the ozonolysis unit comprises a bubble column reactor.

3. The method of claim 1 , wherein the ozone is present in an amount of from 1 to 5 times stoichiometric amount relative to a number of unsaturated bonds in the C18:1 free fatty acid.

4. The method of claim 1 , wherein the reacting at least a portion of the C18:1 free fatty acid in the fatty acid stream with ozone is carried out at a temperature in a range of from 20° C. to 50° C.

5. The method of claim 1 , further comprising introducing a solvent into the ozonolysis unit.

6. The method of claim 5 , wherein the solvent comprises at least one liquid solvent selected from the group consisting of an alcohol, methyl acetate, DMSO, dimethylformamide, an ether, chloroform, a C5-C12 hydrocarbon, and combinations thereof.

7. The method of claim 1 , wherein the reductive agent comprises hydrogen over a platinum catalyst palladium catalyst, or a combination thereof.

8. The method of claim 1 , further comprising isomerizing at least a portion of the paraffin product to produce a corresponding iso-paraffin.

9. A method for producing jet range hydrocarbons comprising:
hydrolyzing a triglyceride stream to produce a fatty acid stream comprising free fatty acid,
introducing the fatty acid stream into a distillation column and separating a C18 and heavier cut comprising C18 fatty acids from the fatty acid stream;
introducing the C18 and heavier cut into an ozonolysis reactor, wherein at least a portion of the free fatty acid is reacted with ozone to produce at least an ozonide intermediate;
reacting the ozonide intermediate with an oxidative agent or a reductive agent to produce oxidized products corresponding to the free fatty acid;
introducing the oxidized products into a hydrotreating unit, wherein at least a portion of the oxidized products are hydrotreated to produce a paraffin stream comprising paraffins corresponding to the oxidized products; and
introducing the paraffin stream into an isomerization unit wherein at least a portion of the paraffin product is isomerized to produce a corresponding iso-paraffin.

10. The method of claim 9 , wherein the fatty acid stream comprises C 18:1 fatty acid.

11. The method of claim 10 , wherein the fatty acid stream further comprises at least one fatty acid selected from the group consisting of C14 fatty acid, C15 fatty acid, C16 fatty acid, C18:0 fatty acid, C18:2 fatty acid, and combinations thereof.

12. The method of claim 9 , wherein the method further comprises introducing a solvent into the ozonolysis reactor.

13. The method of claim 12 , wherein the solvent comprises at least one liquid solvent selected from the group consisting of an alcohol, methyl acetate, DMSO, dimethylformamide, an ether, chloroform, a C5-C12 hydrocarbon, and combinations thereof.

14. The method of claim 12 , wherein the oxidative agent comprises hydrogen peroxide and the reductive agent comprises at least one selected from the group consisting of triphenylphosphine, thiourea, zinc, dimethyl sulfide, sodium borohydride, hydrogen over a platinum catalyst or palladium catalyst, and combinations thereof.

15. A system for producing jet range hydrocarbons comprising:
a hydrolysis unit configured to hydrolyze at least a portion of a triglyceride stream to produce at least a free fatty acid stream;
a distillation column disposed between the hydrolysis unit and the ozonolysis unit, wherein the distillation column is configured to separate a C18 and heavier cut comprising C18 fatty acids from the free fatty acid stream;
an ozonolysis unit fluidically coupled to the C18 and heavier cut, wherein the ozonolysis unit is configured to react at least a portion of the free fatty acid stream with ozone to produce at least an ozonide intermediate corresponding to the free fatty acid in the fatty acid stream and wherein the ozonolysis unit is configured to react at least a portion of the ozonide intermediate with an oxidative agent to produce at least an oxidized product stream comprising oxidized products corresponding to the ozonide intermediate;
a hydrotreating unit fluidically coupled to the oxidized product stream, wherein the hydrotreating unit is configured to react at least a portion of the oxidized products with hydrogen to produce at least a paraffin product stream comprising paraffins corresponding to the oxidized products; and
an isomerization unit fluidically coupled to the paraffin product stream, wherein the isomerization unit is configured to isomerize at least a portion of the paraffins to produce an isomerized product stream comprising iso-paraffins.

16. The system of claim 15 , wherein the ozonolysis unit comprises a bubble column reactor.

17. The system of claim 15 , further comprising a product distillation column fluidically coupled to the isomerized product stream, wherein the product distillation column is configured to separate a jet range hydrocarbon stream comprising hydrocarbons with carbon numbers from 9 to 16 from the isomerized product stream.

Assignees

• Exxonmobil Technology & Engineering Company

Inventors

• Hanks Patrick L

Classifications

• C10G69/02 Primary

  plural serial stages only · CPC title

• B01D3/14

  Fractional distillation {or use of a fractionation or rectification column} · CPC title

• B01J10/00

  Chemical processes in general for reacting liquid with gaseous media other than in the presence of solid particles, or apparatus specially adapted therefor (B01J19/08 takes precedence; separation, e.g. distillation, also combined with chemical reactions B01D, {e.g. B01D3/009}) · CPC title

• B01J19/245

  placed in series · CPC title

• C07C1/20

  starting from organic compounds containing only oxygen atoms as heteroatoms · CPC title