Estolide compound containing ketone functional group and method for preparing the same

Patent metadata

Field	Value
Publication number	US-9637701-B2
Application number	US-201514792959-A
Country	US
Kind code	B2
Filing date	Jul 7, 2015
Priority date	Jul 8, 2014
Publication date	May 2, 2017
Grant date	May 2, 2017

Abstract

A method for preparing a ketone group-containing estolide compound and a ketone group-containing estolide compound prepared thereby are disclosed. The method for preparing a ketone group-containing estolide compound includes converting biomass fat into a fatty acid; separating the fatty acid into a C16 saturated fatty acid and a C18 unsaturated fatty acid; increasing an amount of oleic acid through partial hydrogenation of the C18 unsaturated fatty acid; synthesizing a C35 ketone through ketonization of the oleic acid; and performing estolide bonding by capping the C16 saturated fatty acid onto the C35 ketone.

First claim

What is claimed is:

1. A method for preparing a ketone group-containing estolide compound, comprising:
converting biomass fat into a fatty acid;
separating the fatty acid into a C16 saturated fatty acid and a C18 unsaturated fatty acid;
increasing an amount of oleic acid through partial hydrogenation of the C 18 unsaturated fatty acid;
synthesizing a C35 ketone through ketonization of the oleic acid; and
performing estolide bonding by capping the C16 saturated fatty acid onto the C35 ketone.

2. The method according to claim 1 , wherein the C16 saturated fatty acid is palmitic acid, and the C18 unsaturated fatty acid comprises oleic acid, linoleic acid and linolenic acid.

3. The method according to claim 1 , wherein partial hydrogenation 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.

4. The method according to claim 3 , wherein the water resistant carrier is ZrO 2 or TiO 2 .

5. The method according to claim 1 , wherein the C18 unsaturated fatty acid comprises about 90% or more of oleic acid through partial hydrogenation.

6. The method according to claim 1 , wherein ketonization is performed by introducing the oleic acid into a fixed bed reactor in the presence of a Mn 2 O 3 or TiO 2 catalyst or a supported catalyst in which zirconium dioxide or thorium dioxide is supported on alumina, followed by reaction at a temperature of about 200° C. to about 600° C. and at a pressure of about 1 psi to about 200 psi.

7. The method according to claim 1 , wherein performing estolide bonding comprises performing reaction by introducing the C35 ketone, the C16 saturated fatty acid and sulfuric acid or perchloric acid having a purity of about 90% or more into a batch reactor.

8. The method according to claim 1 , wherein, in performing estolide bonding, the C35 ketone and the C16 saturated fatty acid are introduced in a molar ratio of about 1:0.1 to about 1:10.

9. A ketone group-containing estolide compound represented by Formula 1.

10. A lubricating oil comprising the ketone group-containing estolide compound according to claim 9 .

11. The lubricating oil according to claim 10 , wherein the lubricating oil has a pour point of about −45° C. to about −25° C. and a viscosity index of about 140 to about 180.

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

• C10N2020/011

  Cloud point · CPC title

• C10N2020/02

  Viscosity; Viscosity index · CPC title

• C10N2030/02

  Pour-point; Viscosity index · CPC title

• C10N2070/00

  Specific manufacturing methods for lubricant compositions · CPC title

• C07C69/28

  esterified with dihydroxylic compounds · CPC title