IP Library Granted Patent US 9,328,305
Granted Patent B2
US 9,328,305 · App. 14/602,752 · Granted May 3, 2016

Catalytic processes for preparing estolide base oils

Inventors: Jakob Bredsguard (Lake Forest, CA); Jeremy Forest (Honolulu, HI); Travis Thompson (Anaheim, CA)
Assignee: Biosynthetic Technologies, LLC
C10M105/34C07C57/02C07C67/465C07C67/48C07C67/54C07C69/34C07C69/604C07C69/675C10M105/36C10M107/32C10M2207/286C10M2207/2825C10M2209/1023C10N2220/022C10N2220/023C10N2220/027C10N2220/028C10N2220/10C10N2230/02C10N2230/64C11C3/00C11C3/003C11C3/08
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Quick Facts
Patent No.
US 9,328,305
App. No.
14/602,752
Granted
May 3, 2016
Kind
B2
Abstract

Provided herein are processes for preparing estolides and estolide base oils from fatty acid reactants utilizing catalysts. Further provided herein are processes for preparing carboxylic esters from at least one carboxylic acid reactant and at least one olefin.

Claims (21)

1. A continuous process comprising:

continuously providing at least one first fatty acid reactant and at least one second fatty acid reactant; and

continuously oligomerizing the at least one first fatty acid reactant with the at least one second fatty acid reactant in the presence of a polymer-supported acid catalyst, to produce an estolide base oil.

2. The process according to claim 1 , wherein the at least one first fatty acid reactant and the at least one second fatty acid reactant are continuously oligomerized in a reactor.

3. The process according to claim 2 , wherein the reactor is equipped with a heat source.

4. The process according to claim 2 , wherein the reactor is a microwave reactor.

5. The process according to claim 2 , wherein the reactor is a continuous stirred tank reactor.

6. The process according to claim 1 , wherein the oligomerizing produces one or more first estolides.

7. The process according to claim 2 , wherein the reactor is a column reactor.

8. The process according to claim 7 , wherein the reactor comprises a first reaction stage.

9. The process according to claim 8 , wherein the reactor comprises two or more reaction stages.

10. The process according to claim 9 , wherein the polymer-supported acid catalyst is present in one or more of the reaction stages.

11. The process according to claim 10 , wherein the polymer-supported acid catalyst comprises a Bronsted acid.

12. The process according to claim 3 , wherein the oligomerizing is carried out at a temperature that is greater than 50° C.

13. The process according to claim 12 , wherein the oligomerizing is carried out at a temperature range of 50° C. to 100° C.

14. The process according to claim 2 , wherein the reactor is a plug flow reactor.

15. The process according to claim 1 , wherein the polymer-supported acid catalyst comprises a sulfonic acid polymer.

16. The process according to claim 15 , wherein the polymer-supported acid catalyst comprises a fluorinated sulfonic acid polymer.

17. The process according to claim 1 , further comprising esterifying the estolide base oil to provide an esterified estolide base oil.

18. The process according to claim 17 , wherein the esterifying is conducted in the presence of an esterifying alcohol.

19. The process according to claim 17 , further comprising hydrogenating the esterified estolide base oil.

Assignments (6)
ASSIGNMENT OF SECURITY INTEREST Recorded Mar 23, 2018
From: EVONIK OIL ADDITIVES USA, INC.
To: BIOSYN HOLDINGS, LLC
Reel/Frame 045684/0293 →
ASSIGNMENT OF SECURITY INTEREST Recorded Mar 23, 2018
From: BP TECHNOLOGY VENTURES INC.
To: BIOSYN HOLDINGS, LLC
Reel/Frame 045688/0600 →
ASSIGNMENT OF SECURITY INTEREST Recorded Mar 23, 2018
From: EVONIK CORPORATION
To: BIOSYN HOLDINGS, LLC
Reel/Frame 045860/0547 →
SECURITY INTEREST Recorded Jan 30, 2018
From: BIOSYNTHETIC TECHNOLOGIES, LLC
To: BP TECHNOLOGY VENTURES INC.
Reel/Frame 045196/0587 →
SECURITY INTEREST Recorded Mar 18, 2016
From: BIOSYNTHETIC TECHNOLOGIES, LLC
To: EVONIK OIL ADDITIVES USA, INC.
Reel/Frame 038146/0859 →
SECURITY INTEREST Recorded Nov 30, 2015
From: BIOSYNTHETIC TECHNOLOGIES, LLC
To: EVONIK CORPORATION
Reel/Frame 037162/0364 →
Continuity (5)
Continuation 14095750 · Dec 3, 2013
Continuation 13199551 · Aug 31, 2011
Provisional Application 61498499 · Jun 17, 2011
Provisional Application 61378891 · Aug 31, 2010
Related Publication 20150197477A1 · Jul 16, 2015