Terminally selective metathesis of polyenes derived from natural oil
AssigneeElevance Renewable Sciences, Inc.
InventorsKeith M. Wampler, Jane Uy, Steven A. Cohen
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Abstract
Methods of carrying out metathesis reactions of natural oil-derived polyenes (e.g., dienes and trienes), including functionalized polyenes, are generally disclosed herein. In some embodiments, the dienes or trienes contain a terminal carbon-carbon double bond, and the metathesis reaction is selective toward reaction of the terminal carbon-carbon double bonds in the polyene. Compounds made by such methods are also generally disclosed herein.
Claims10
A method for forming a dimer by olefin metathesis, the method comprising:
- providing a reactant composition comprising a terminally unsaturated diene, which is methyl 9,12-tridecadienoate;
- and
- self-metathesizing the terminally unsaturated diene, methyl 9,12-tridecadienoate, in the presence of a metathesis catalyst at the terminal double bond of the terminally unsaturated diene to form a product composition comprising 1,24-dimethyl 9,12,15-tetracosatriendioate;
- provided that the terminally unsaturated diene, methyl 9,12-tridecadienoate, is derived from a natural oil.
A method for forming a dimer by olefin metathesis, the method comprising:
- providing a reactant composition comprising a terminally unsaturated diene, which is methyl 9,12-tridecadienoate, and methyl 9-decenoate;
- and
- cross-metathesizing the terminally unsaturated diene, methyl 9,12-tridecadienoate, and the methyl 9-decenoate in the presence of a metathesis catalyst at the terminal double bond of the terminally unsaturated diene to form a product composition comprising 1,21-dimethyl 9,12-heneicosadiendioate;
- provided that the terminally unsaturated diene, methyl 9,12-tridecadienoate, or the methyl 9-decenoate is derived from a natural oil.
Dependencies are inferred from the claim text.