Materials derived from fermentation-produced rhamnolipids and methods of production

Patent metadata

Field	Value
Publication number	US-10344304-B2
Application number	US-201515127172-A
Country	US
Kind code	B2
Filing date	Mar 19, 2015
Priority date	Mar 20, 2014
Publication date	Jul 9, 2019
Grant date	Jul 9, 2019

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.

First claim

What is claimed is:

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

Assignees

• Ju Lu Kwang
• Miao Shida
• Univ Akron

Inventors

• Ju Lu-Kwang
• Miao Shida

Classifications

• C08G18/4263

  containing carboxylic acid groups · CPC title

• C07H13/04

  having the esterifying carboxyl radicals attached to acyclic carbon atoms · CPC title

• C07H13/06

  Fatty acids · CPC title

• C12P19/44

  Preparation of O-glycosides, e.g. glucosides {(polysaccharides and not substituted disaccharides C12P19/04, C12P19/12)} · CPC title

• C11C1/025

  by saponification and release of fatty acids · CPC title