IP Library › Granted Patent US 10,344,304
Granted Patent B2
US 10,344,304 · App. 15/127,172 · Granted Jul 9, 2019

Materials derived from fermentation-produced rhamnolipids and methods of production

Inventors: Lu-Kwang Ju (Akron, OH); Shida Miao (Washington, DC)
Assignee: THE UNIVERSITY OF AKRON
C12P7/6409C07H13/04C07H13/06C08G18/4263C08G18/73C11C1/025C12P7/64C12P19/44
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Quick Facts
Patent No.
US 10,344,304
App. No.
15/127,172
Granted
Jul 9, 2019
Kind
B2
Abstract

A method of preparing a product derived from a rhamnolipid includes the steps of: providing a rhamnolipid, combining the rhamnolipid with a reagent, allowing the rhamnolipid and reagent to react to form a product derived from the rhamnolipid, and collecting the product derived from the rhamnolipid. An exemplary product is dimeric β-hydroxy fatty acid.

Claims (39)

1. A method of preparing a product derived from a rhamnolipid comprising steps of:

providing a rhamnolipid;

combining the rhamnolipid with a reagent;

allowing the rhamnolipid and the reagent to react to form a product derived from the rhamnolipid, where the step of allowing does not utilize an enzyme;

collecting the product derived from the rhamnolipid, where the product derived from the rhamnolipid is a compound having the following formula:

where C 1 and C 2 are each a hydrocarbon chain having between four and fourteen carbon atoms, and where X 1 and X 2 are each selected from the group consisting of a hydroxyl group and an alkoxy group, and

polymerizing the product derived from the rhamnolipid.

2. The method of claim 1 , where C 1 and C 2 are each alkyl chains having seven carbon atoms.

3. The method of claim 2 , where X 1 and X 2 are each hydroxyl groups.

4. A method of modifying a rhamnolipid comprising the steps of: providing a rhamnolipid having the following formula:

where C 1 and C 2 are each a hydrocarbon chain having between four and fourteen carbon atoms, where X 1 is selected from the group consisting of a hydroxyl group and an alkoxy group, where X 2 is oxygen; and

chemically attaching a compound at position X 3 , where the chemically attached compound is selected from the group consisting of

5. The method of claim 4 , where C 1 and C 2 are each alkyl chains having seven carbon atoms.

6. The method of claim 4 where the chemically attached compound is

7. The method of claim 4 where the chemically attached compound is

8. The method of claim 7 , further comprising the step of polymerizing the modified rhamnolipid.

9. The method of claim 7 , further comprising the step of polymerizing the modified rhamnolipid.

10. A method of preparing a product derived from a rhamnolipid comprising steps of:

providing a rhamnolipid,

combining the rhamnolipid with a reagent, where the reagent is selected from the group consisting of benzoyl chloride and acetylated glucose,

allowing the rhamnolipid and the reagent to react to form a product derived from the rhamnolipid, and

collecting the product derived from the rhamnolipid.

11. The method of claim 10 , wherein the reagent is benzoyl chloride.

12. The method of claim 10 , wherein the reagent is acetylated glucose.

13. A method of preparing a product derived from a rhamnolipid comprising steps of:

providing a rhamnolipid,

combining the rhamnolipid with an acid,

allowing the rhamnolipid and the acid to react in the presence of an alcohol, to form a product derived from the rhamnolipid, wherein the step of allowing does not utilize an enzyme, wherein the rhamnolipid is provided by a rhamnolipid mixture comprising both mono-rhamnolipids and di-rhamnolipids, and wherein the product derived from the rhamnolipid is dimeric β-hydroxy fatty acid,

combining a catalyst with the dimeric β-hydroxy fatty acid to form a catalyst and product mixture, and

heating the catalyst and product mixture,

whereby the steps of combining and heating polymerize the dimeric β-hydroxy fatty acid.

14. A method of preparing a product derived from a rhamnolipid comprising steps of:

providing a rhamnolipid,

combining the rhamnolipid with a reagent, wherein the reagent is a diisocyanate,

allowing the rhamnolipid and the reagent to react to form a product derived from the rhamnolipid, and

collecting the product derived from the rhamnolipid, wherein the product derived from the rhamnolipid is a polyurethane.

15. The method of claim 14 , where the rhamnolipid is a mono-rhamnolipid ethyl ester.

16. The method of claim 14 , the rhamnolipid having the formula

wherein C 1 and C 2 are each a hydrocarbon chain having between four and fourteen carbon atoms, wherein X 1 is selected from the group consisting of a hydroxyl group and an alkoxy group, where X 2 is oxygen, wherein X 3 is selected from the group consisting of

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 19, 2016
From: JU, LU-KWANG; MIAO, SHIDA
To: THE UNIVERSITY OF AKRON
Reel/Frame 040070/0177 →
Continuity (2)
Provisional Application 61955849 · Mar 20, 2014
Related Publication 20170175151A1 · Jun 22, 2017