Processes of preparing estolide compounds that include removing sulfonate residues

Patent metadata

Field	Value
Publication number	US-9783484-B2
Application number	US-201615162347-A
Country	US
Kind code	B2
Filing date	May 23, 2016
Priority date	Jun 18, 2012
Publication date	Oct 10, 2017
Grant date	Oct 10, 2017

Abstract

Provided herein are processes of preparing sulfonated estolide compounds, and the removal of sulfonate residues from those compounds to provide desulfonated estolide base oils. Exemplary sulfonated estolide compounds include those selected from the formula:

wherein z is an integer selected from 0 to 15; q is an integer selected from 0 to 15; x is, independently for each occurrence, an integer selected from 0 to 20; y is, independently for each occurrence, an integer selected 0 to 20; n is equal to or greater than 0; R 6 is selected from —OH, optionally substituted alkyl, and optionally substituted aryl; and R 2 is selected from hydrogen and optionally substituted alkyl that is saturated or unsaturated, and branched or unbranched, wherein each fatty acid chain residue of said compounds is independently optionally substituted.

First claim

The invention claimed is:

1. A process comprising:
oligomerizing at least one first fatty acid reactant with at least one second fatty acid reactant in the presence of a sulfonic acid catalyst to provide at least one first estolide compound having at least one sulfonate residue;
removing the at least one sulfonate residue to provide an estolide base oil; and
esterifying the estolide base oil to provide an esterified estolide base oil.

2. The process according to claim 1 , wherein the oligomerizing occurs at a temperature of about 100° C. or less.

3. The process according to claim 1 , wherein the removing occurs at a temperature of at least 100° C.

4. The process according to claim 1 , wherein the removing occurs at a temperature of about 100° C. to about 175° C.

5. The process according to claim 1 , wherein the sulfonic acid catalyst is selected from at least one of sulfuric acid or an optionally substituted alkyl sulfonic acid.

6. The process according to claim 1 , wherein the sulfonic acid catalyst comprises an unsubstituted alkyl sulfonic acid.

7. The process according to claim 1 , further comprising hydrogenating the esterified estolide base oil.

8. The process according to claim 1 , wherein the sulfonic acid catalyst comprises sulfuric acid.

9. The process according to claim 6 , wherein the sulfonic acid catalyst comprises methanesulfonic acid.

10. A process comprising:
oligomerizing at least one first fatty acid reactant with at least one second fatty acid reactant in the presence of a sulfonic acid catalyst to provide at least one first estolide compound having at least one sulfonate residue, wherein the oligomerizing occurs at a temperature of 100° C. or less; and
removing the at least one sulfonate residue at a temperature of at least 100° C. to provide an estolide base oil.

11. The process according to claim 10 , further comprising esterifying the estolide base oil to provide an esterified estolide base oil.

12. The process according to claim 11 , further comprising hydrogenating the esterified estolide base oil.

13. The process according to claim 10 , wherein the removing occurs at a temperature of 100° C. to 175° C.

14. The process according to claim 10 , wherein the sulfonic acid catalyst is selected from at least one of sulfuric acid or an unsubstituted alkyl sulfonic acid.

15. A process comprising:
oligomerizing at least one first fatty acid reactant with at least one second fatty acid reactant in the presence of a sulfonic acid catalyst to provide at least one first estolide compound having at least one sulfonate residue, wherein the oligomerizing occurs at a temperature of 100° C. or less;
removing the at least one sulfonate residue at a temperature of at least 100° C. to provide an estolide base oil; and
esterifying the estolide base oil to provide an esterified estolide base oil.

16. The process according to claim 15 , further comprising hydrogenating the esterified estolide base oil.

17. The process according to claim 15 , wherein the removing occurs at a temperature of 100° C. to 175° C.

18. The process according to claim 15 , wherein the sulfonic acid catalyst is selected from at least one of sulfuric acid or an optionally substituted alkyl sulfonic acid.

19. The process according to claim 15 , wherein the sulfonic acid catalyst comprises sulfuric acid.

20. The process according to claim 15 , wherein the sulfonic acid catalyst comprises methanesulfonic acid.

21. The process according to claim 10 , wherein the oligomerizing occurs at a temperature of less than 100° C., and removing the at least one sulfonate residue occurs at a temperature of at least 110° C.

22. The process according to claim 15 , wherein the oligomerizing occurs at a temperature of less than 100° C., and removing the at least one sulfonate residue occurs at a temperature of at least 110° C.

Assignees

• Biosynthetic Technologies Llc

Inventors

• Arnold Chris
• Likhotvorik Igor
• Thompson Travis
• Hoglen Dean Kent
• Williams Eric Lee
• Lutz Marlon

Classifications

• C11C3/14

  by isomerisation {(isomerisation induced by hydrogenation C11C3/12)} · CPC title

• C11C3/08

  with fatty acids · CPC title

• C11C3/006 Primary

  by oxidation · CPC title

• C08F20/64

  Acids; Metal salts or ammonium salts thereof · CPC title

• C07C305/04

  being acyclic and saturated · CPC title