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:
Claims34
1-41. (canceled)
A process of producing an estolide base oil comprising:
- providing at least one triglyceride having at least one fatty acid residue with at least one internal site of unsaturation;
- providing at least one alpha olefin having at least three carbon atoms;
- 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 and a metathesized fatty acid product;
- hydrolyzing the metathesized fatty acid product into at least one first fatty acid product, wherein the at least one first fatty acid product comprises at least one fatty acid having an internal site of unsaturation and at least one fatty acid having a terminal site of unsaturation;
- providing an oligomerization catalyst;
- and
- oligomerizing at least a portion of the at least one first fatty acid product 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 a first fatty acid and a carbon of a site of unsaturation of a second fatty acid.
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At least one compound according to Formula III:
- wherein
- n is an integer equal to or greater than 0;
- R1 is an optionally substituted, branched or unbranched alkyl that is saturated or unsaturated;
- R2 is selected from hydrogen and optionally substituted 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 independently optionally substituted and z is, independently for each occurrence, an integer selected from 0 to 40.
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Dependencies are inferred from the claim text.