Glycolipid composition and method thereof

Patent metadata

Field	Value
Publication number	US-10995352-B2
Application number	US-202016870910-A
Country	US
Kind code	B2
Filing date	May 9, 2020
Priority date	Jun 3, 2019
Publication date	May 4, 2021
Grant date	May 4, 2021

Abstract

The present disclosure relates to glycolipid compositions, methods for making glycolipid compositions, and their uses thereof. Glycolipid compositions can be prepared via yeast-mediated catalyzed reaction, and exhibit excellent surfactant properties having high corrosion inhibition performance, good reducing surface tension efficiency. Processes of the present disclosure can provide glycolipid compositions having one or more of: a ratio of lactonic glycolipids to glycolipid acylic esters is from about 1:10 to about 10:1, a molecular weight of from about 400 g/mol to about 10,000 g/mol, a corrosion rate of carbon steel from about 0.5 MPY to about 100 MPY at room temperature and at pH 4-6. Furthermore, aqueous solutions of the glycolipid compositions of the present disclosure can have a surface tension of from about 20 mN/m to about 80 mN/m.

First claim

What is claimed is:

1. A glycolipid composition comprising:
one or more lactonic glycolipids having:
one or more linear C 3 -C 40 alpha-olefin or branched C 4 -C 40 alpha-olefin, and
one or more C 10 -C 60 disaccharide; and

one or more glycolipid acyclic esters having:
one or more linear C 3 -C 40 alpha-olefin or branched C 4 -C 40 alpha-olefin, and
one or more C 10 -C 60 disaccharide;

wherein the one or more linear C 3 -C 40 alpha-olefin is selected from the group consisting of 1-propene, 1-butene, 1-pentene, 1-hexene, 1-heptene, 1-octene, 1-nonene, 1-decene, 1-undecene, 1-dodecene, 1-tridecene, 1-tetradecene, 1-pentadecene, 1-hexadecene, 1-heptadecene, 1-octadecene, 1-nonadecene, and 1-eicosene; and
wherein the one or more branched C 4 -C 40 alpha-olefin is selected from the group consisting of 3,4,5,-trimethyl-hept-1-ene, 4-methyl-dec-1-ene, 4-ethyl-2-methyl-dec-1-ene, and 5-propyl-2-ethyl-undec-1-ene.

2. The glycolipid composition of claim 1 , wherein the one or more C 10 -C 60 disaccharide is a sophorose.

3. The glycolipid composition of claim 1 , wherein the one or more C 10 -C 60 disaccharide comprises one or more acetyl groups.

4. The glycolipid composition of claim 1 , wherein the glycolipid composition has a molecular weight of from about 400 g/mol to about 10,000 g/mol.

5. A method for forming one or more glycolipid compositions in a reactor, the method comprising:
introducing a population of yeast to air and a first medium comprising one or more nitrogen source and one or more C 10 -C 60 disaccharide to form a first culture;
introducing at least a portion of the first culture to air and a feedstock in a second medium comprising one or more nitrogen source to form a second culture comprising the one or more glycolipid compositions, wherein the feedstock comprises (1) two or more C 5 -C 30 monosaccharide and (2) one or more linear C 3 -C 40 alpha-olefin or branched C 4 -C 40 alpha-olefin;
wherein the one or more linear C 3 -C 40 alpha-olefin is selected from the group consisting of 1-propene, 1-butene, 1-pentene, 1-hexene, 1-heptene, 1-octene, 1-nonene, 1-decene, 1-undecene, 1-dodecene, 1-tridecene, 1-tetradecene, 1-pentadecene, 1-hexadecene, 1-heptadecene, 1-octadecene, 1-nonadecene, and 1-eicosene; and
wherein the one or more branched C 4 -C 40 alpha-olefin is selected from the group consisting of 3,4,5,-trimethyl-hept-1-ene, 4-methyl-dec-1-ene, 4-ethyl-2-methyl-dec-1-ene, 5-propyl-2-ethyl-undec-1-ene, dimer of 1-dodecene, dimer of 1-hexadecene, dimer of 1-octadecene; and
introducing one or more antibiotic to the first culture or the second culture; and
recovering the one or more glycolipid compositions from the second culture.

6. The method of claim 5 , wherein the one or more glycolipid compositions comprises one or more lactonic glycolipids and one or more glycolipid acyclic esters.

7. The method of claim 5 , wherein the two or more C 5 -C 30 monosaccharides comprise glucose, mannose, fructose, or a combination thereof.

8. The method of claim 5 , wherein the two or more C 5 -C 30 monosaccharides comprise one or more acetyl groups.

9. The method of claim 5 , further comprising maintaining the first culture and the second culture at a temperature of about 45° C. or less.

Assignees

• Exxonmobil Res & Eng Co

Inventors

• Nandi Partha
• Zhang Xiaozhou
• Chatterjee Mohor
• Grankina Vera
• Paek Changyub
• Cao Fang

Classifications

• C12P7/16

  Butanols · CPC title

• C12P5/026

  Unsaturated compounds, i.e. alkenes, alkynes or allenes · CPC title

• C12N1/26

  Processes using, or culture media containing, hydrocarbons (refining of hydrocarbon oils by using microorganisms C10G32/00) · CPC title

• Y02E50/10

  Biofuels, e.g. bio-diesel · CPC title

• C12P19/44 Primary

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