# US 10,479,755 B2 · Terminally selective metathesis of polyenes derived from natural oil

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- Number: US 10,479,755 B2
- Document ID: US10479755B2
- Status: Granted
- Kind: B2
- Application number: 15/376,239
- Filed: 2016-12-12
- Published: 2017-06-29
- Granted: 2019-11-19
- Earliest claimed: 2014-10-31
- Assignees: Elevance Renewable Sciences, Inc.
- Applicants: Elevance Renewable Sciences, Inc.
- Inventors: Keith M. Wampler; Jane Uy; Steven A. Cohen
- Web page: https://patentgrep.com/patent/US10479755B2

## CPC

- C07C 67/475: by splitting of carbon-to-carbon bonds and redistribution, e.g. disproportionation or migration of [IMAGE cpc-sch-C07C-0963.gif] groups between different molecules
- C11C 1/04: by hydrolysis
- C11C 3/14: by isomerisation {(isomerisation induced by hydrogenation C11C3/12)}
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C11C: FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM

## 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.

## Claims

### Claim 1

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.

### Claim 2 (depends on 1)

The method of claim 1, comprising hydrogenating the 1,24-dimethyl 9,12,15-tetracosatriendioate to form 1,24-dimethyl tetracosanedioate.

### Claim 3 (depends on 2)

The method of claim 2, comprising converting the 1,24-dimethyl tetracosanedioate to form 1,24-tetracosanedioic acid.

### Claim 4 (depends on 3)

The method of claim 3, wherein the converting comprises hydrolysis.

### Claim 5 (depends on 3)

The method of claim 3, wherein the converting comprises saponification followed by acidification.

### Claim 6

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.

### Claim 7 (depends on 6)

The method of claim 6, comprising hydrogenating the 1,21-dimethyl 9,12-heneicosadiendioate to form 1,21-dimethyl heneicosanedioate.

### Claim 8 (depends on 7)

The method of claim 7, comprising converting the 1,21-dimethyl heneicosanedioate to form 1,21-heneicosanedioic acid.

### Claim 9 (depends on 8)

The method of claim 8, wherein the converting comprises hydrolysis.

### Claim 10 (depends on 8)

The method of claim 8, wherein the converting comprises saponification followed by acidification.