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US 8,580,985 B2Granted
Processes for preparing estolide base oils and oligomeric compounds that include cross metathesis
AssigneeBiosynthetic Technologies, LLC
InventorsTravis Thompson, Kelly Parson, Jakob Bredsguard, Jeremy Forest
Life of this patent
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Abstract
Provided herein are estolide base oils and oligomeric compounds prepared from processes that include cross metathesis. Exemplary processes include the preparation of terminally-unsaturated fatty acids by cross metathesis, and the subsequent oligomerization of terminally-unsaturated fatty acids to provide estolide compounds, such as the process set forth below:
Claims19
A process of producing an estolide base oil comprising:
- providing at least one triglyceride having at least one oleic acid residue;
- providing at least one alpha olefin selected from one or more of ethene, propene, 1-butene, 1-pentene, 1-hexene, 1-heptene, or 1-octene;
- contacting the at least one triglyceride with the at least one alpha olefin in the presence of a metathesis catalyst to provide an olefin product comprising 1-decene, and a metathesized fatty acid product comprising at least one 9-decenoic acid residue;
- hydrolyzing the metathesized fatty acid product to provide a free fatty acid product comprising 9-decenoic acid;
- providing an oligomerization catalyst;
- and
- oligomerizing the 9-decenoic acid with a second fatty acid in the presence of the oligomerization catalyst to produce an estolide base oil, wherein said oligomerizing comprises forming a covalent bond between an oxygen of a carboxylic group of the second fatty acid and a carbon of the double bond of the 9-decenoic acid.
4 more elements
At least one compound according to Formula III:
- wherein
- n is an integer selected from 0 to 20;
- R1 is an unsubstituted, branched or unbranched C7 to C17 alkyl that is saturated or unsaturated;
- R2 is an unsubstituted C1 to C22 alkyl that is saturated or unsaturated, and branched or unbranched;
- and
- R3 and R4, independently for each occurrence, are selected from
- wherein R3 and R4 are unsubstituted and z is 7.
4 more elements
Dependencies are inferred from the claim text.