Method of producing estolide having high structural stability

Patent metadata

Field	Value
Publication number	US-9845280-B2
Application number	US-201514884247-A
Country	US
Kind code	B2
Filing date	Oct 15, 2015
Priority date	Oct 21, 2014
Publication date	Dec 19, 2017
Grant date	Dec 19, 2017

Abstract

Disclosed is a method of producing an estolide having high structural stability, including: a) preparing a fatty acid mixture from biomass-derived oil; b) separating the fatty acid mixture into a C16 fatty acid and a C18 fatty acid; c) converting the C18 fatty acid into a C18 or C17 linear internal olefin; and d) subjecting the C18 or C17 linear internal olefin and the C16 fatty acid to an estolide reaction, thus obtaining an estolide.

First claim

The invention claimed is:

1. A method of producing an estolide having high structural stability, comprising:
a) preparing a fatty acid mixture comprising C4 to C24 from biomass-derived oil;
b) separating the fatty acid mixture into a C16 fatty acid and a C18 fatty acid, respectively;
c) converting the separated C18 fatty acid into a C18 or C17 linear internal olefin; and
d) subjecting the C18 or C17 linear internal olefin and the separated C16 fatty acid to an estolide reaction, wherein the estolide reaction is a crosslinking reaction of unsaturated double bonds of hydrocarbons with a fatty acid using an acid catalyst, thus obtaining an estolide.

2. A method of producing an estolide having high structural stability, comprising:
A) preparing a fatty acid mixture comprising C4 to C24 from biomass-derived oil; and
B) subjecting the fatty acid mixture to an estolide reaction and then hydrodeoxygenation, wherein the estolide reaction is a crosslinking reaction of unsaturated double bonds of hydrocarbons with a fatty acid using an acid catalyst, thus obtaining an estolide.

3. The method of claim 1 , wherein c) comprises converting the C18 fatty acid into a C18 linear internal olefin through partial hydrogenation and dehydration.

4. The method of claim 1 , wherein c) comprises converting the C18 fatty acid into a C17 linear internal olefin through decarbonylation.

5. The method of claim 1 , further comprising e) performing hydrotreating to increase stearic acid content, between steps a) and b).

6. The method of claim 1 , further comprising f) hydrotreating the C18 fatty acid separated in b) to increase stearic acid content, between steps b) and c).

7. The method of claim 2 , further comprising C) performing hydrotreating to increase stearic acid content, after A).

8. The method of claim 2 , further comprising D) separating or purifying the estolide obtained in B) to obtain a desired estolide.

9. The method of claim 1 , wherein a) or A) is performed through de-esterification or hydrolysis of triglyceride in the biomass-derived oil.

10. The method of claim 2 , wherein a) or A) is performed through de-esterification or hydrolysis of triglyceride in the biomass-derived oil.

11. An estolide, produced by the method of claim 1 , wherein the estolide comprises an estolide represented by Chemical Formula 1 or Chemical Formula 2 below:

12. An estolide, produced by the method of claim 2 , wherein the estolide comprises an estolide represented by Chemical Formula 1 or Chemical Formula 2 below:

13. A lubricating oil, comprising an estolide produced by the method of claim 1 , wherein the estolide comprises an estolide represented by Chemical Formula 1 or Chemical Formula 2 below:

14. A lubricating oil, comprising an estolide produced by the method of claim 2 , wherein the estolide comprises an estolide represented by Chemical Formula 1 or Chemical Formula 2 below:

Assignees

• Sk Innovation Co Ltd
• Sk Lubricants Co Ltd

Inventors

• Jeon Hee Jung
• Lee Jong Su
• Kim Yong Woo

Classifications

• C07C51/09

  from carboxylic acid esters or lactones · CPC title

• C07C2523/883

  and nickel · CPC title

• C10N2020/011

  Cloud point · CPC title

• C07C53/126

  Acids containing more than four carbon atoms · CPC title

• C10M105/34

  of monocarboxylic acids · CPC title