Estolide compound and method for preparing the same

Patent metadata

Field	Value
Publication number	US-9714209-B2
Application number	US-201514793010-A
Country	US
Kind code	B2
Filing date	Jul 7, 2015
Priority date	Jul 8, 2014
Publication date	Jul 25, 2017
Grant date	Jul 25, 2017

Abstract

A method for preparing an estolide compound and an estolide compound prepared thereby are disclosed. The method for preparing an estolide compound includes: converting biomass fat into a fatty acid; separating the fatty acid into a C 16 saturated fatty acid and a C 18 unsaturated fatty acid; preparing a linear internal olefin (LIO); increasing an amount of oleic acid through partial hydrogenation of the C 18 unsaturated fatty acid; synthesizing an estolide polymer through cross metathesis of the oleic acid; capping the C 16 saturated fatty acid onto the estolide polymer; and reacting the estolide polymer with the linear internal olefin.

First claim

What is claimed is:

1. A method for preparing an estolide compound, comprising:
converting biomass fat into a fatty acid;
separating the fatty acid into a C 16 saturated fatty acid and a C 18 unsaturated fatty acid;
preparing a linear internal olefin (LIO);
increasing an amount of oleic acid through partial hydrogenation of the C 18 unsaturated fatty acid;
synthesizing an estolide polymer through cross metathesis of the oleic acid;
capping the C 16 saturated fatty acid onto the estolide polymer; and
reacting the estolide polymer with the linear internal olefin.

2. The method according to claim 1 , wherein the C 16 saturated fatty acid is palmitic acid, and the C 18 unsaturated fatty acid comprises oleic acid, linoleic acid and linolenic acid.

3. The method according to claim 1 , wherein the linear internal olefin is prepared through decarbonylation of some of the biomass-derived fatty acid.

4. The method according to claim 3 , wherein decarbonylation is performed at a reaction temperature of about 180° C. to about 250° C. for about 1 minute to about 600 minutes.

5. The method according to claim 1 , wherein the linear internal olefin is prepared using partial hydrogenation for converting the biomass-derived fatty acid into a fatty alcohol and dehydration.

6. The method according to claim 5 , wherein partial hydrogenation is performed at a reaction temperature of about 120° C. to about 500° C. and at a reaction pressure of about 1 bar to about 30 bar in terms of H 2 , and dehydration is performed at a reaction temperature of 250° C. to 500° C.

7. The method according to claim 5 , wherein dehydration is performed in the presence of at least one metal oxide catalyst selected from the group consisting of alumina, silica-alumina, zirconia, titania, iron oxide, vanadium oxide, zeolite, and alumina-supported mesoporous silica.

8. The method according to claim 1 , wherein the linear internal olefin is a C 15 linear internal olefin prepared by converting some of the C 16 saturated fatty acid.

9. The method according to claim 1 , wherein increasing the amount of oleic acid through partial hydrogenation of the C 18 unsaturated fatty acid is performed at a reaction temperature of about 160° C. to about 180° C. and at a reaction pressure of about 20 bar to about 40 bar in the presence of a supported catalyst in which NiMo, CoMo or Mo is supported on a water resistant carrier.

10. The method according to claim 9 , wherein the water resistant carrier is ZrO 2 or TiO 2 .

11. The method according to claim 1 , wherein the C 18 unsaturated fatty acid comprises 90% or more of oleic acid through partial hydrogenation.

12. The method according to claim 1 , wherein, in synthesizing an estolide polymer through cross metathesis of the oleic acid, cross metathesis is performed at a reaction temperature of about 25° C. to about 80° C. and at a reaction pressure of about 0.1 bar to about 10 bar.

13. The method according to claim 1 , wherein, in capping the C 16 saturated fatty acid onto the estolide polymer, the estolide polymer and the C 16 saturated fatty acid react in a weight ratio of about 1:0.1 to about 1:20 at a reaction temperature of about 25° C. to about 80° C. and at a reaction pressure of about 0.1 bar to about 10 bar.

14. The method according to claim 1 , wherein, in reacting the estolide polymer with the linear internal olefin (LIO), the estolide polymer and the LIO react in a weight ratio of about 1:0.1 to about 1:20 at a reaction temperature of about 25° C. to about 80° C. and at a reaction pressure of about 0.1 bar to about 10 bar.

Assignees

• Sk Innovation Co Ltd
• Sk Lubricants Co Ltd

Inventors

• Kim Yong Woo
• Jeon Hee Jung
• Kwon Wan Seop
• Kim Hak Mook
• Ok Jin Hee

Classifications

• C07C2531/24

  Phosphines · CPC title

• C10M2207/301

  used as base material · CPC title

• C07C67/31

  by introduction of functional groups containing oxygen only in singly bound form · CPC title

• C07C51/44

  by distillation · CPC title

• C10M105/42

  Complex esters, i.e. compounds containing at least three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compound: monohydroxy compounds, polyhydroxy compounds, monocarboxylic acids, polycarboxylic acids and hydroxy carboxylic acids · CPC title