Chemoenzymatic synthesis of sebacic acid and dibutyl sebacate
AssigneeThe Government of the United States of America, as represented by the Secretary of the Navy
InventorsGregory A. Ellis, Igor L. Medintz, Alfred G. Stern, Adam A. Meares, Aaron D. Smith
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Abstract
Described herein is a chemoenzymatic route to produce the small molecule sebacic acid from the renewable feedstock, e.g. vegetable oil. In one embodiment, this involves treating the a starting material such vegetable oil with KMnO4, sodium thiocyanate, and acid to obtain sebacic acid. Yield could be improved by pretreating the starting material with a lipase and then with a linoleic acid isomerase obtained from Propionibacterium acnes to obtain trans-10, cis-12 conjugated linoleic acid (CLA). The sebacic acid can be further processed with lipase and 1-butanol to obtain dibutyl sebacate.
Claims16
A method of making sebacic acid, the method comprising:
- providing a starting material comprising linoleic acid;
- treating the starting material with a first lipase to obtain free linoleic acid;
- treating the free linoleic acid with a linoleic acid isomerase obtained from Propionibacterium acnes to obtain trans-10, cis-12 conjugated linoleic acid;
- and
- treating the trans-10, cis-12 conjugated linoleic acid with an oxidant to obtain sebacic acid.
A method of making sebacic acid, the method comprising:
- providing a starting material comprising vegetable oil, linoleic acid, and/or trans-10, cis-12 conjugated linoleic acid;
- and
- treating the starting material with KMnO4, sodium thiocyanate, and acid to obtain sebacic acid.
A method of making sebacic acid, the method comprising:
- providing a starting material comprising linoleic acid;
- treating the starting material with a linoleic acid isomerase obtained from Propionibacterium acnes to obtain trans-10, cis-12 conjugated linoleic acid;
- and
- treating the trans-10, cis-12 conjugated linoleic acid with an oxidant to obtain sebacic acid.
A method of making sebacic acid, the method comprising:
- providing a starting material comprising a fatty acid or a fatty acid-glycerin adduct:
- wherein the fatty acid has an alkene group isomerizable to the 10 position;
- treating the starting material with a first lipase to obtain the fatty acid in free form, when the starting material is the fatty acid-glycerin adduct;
- treating the fatty acid with a fatty acid isomerase that converts the alkene to the 10 position;
- and
- treating the fatty acid having the 10 position alkene with an oxidant to obtain sebacic acid.
Dependencies are inferred from the claim text.