# US 10,501,569 B2 · High-weight glyceride oligomers and methods of making the same

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- Number: US 10,501,569 B2
- Document ID: US10501569B2
- Status: Granted
- Kind: B2
- Application number: 16/194,627
- Filed: 2018-11-19
- Published: 2019-06-27
- Granted: 2019-12-10
- Earliest claimed: 2016-08-18
- Assignees: Elevance Renewable Sciences, Inc.
- Applicants: Elevance Renewable Sciences, Inc.
- Inventors: Steven A. Cohen; Thomas E. Snead
- Web page: https://patentgrep.com/patent/US10501569B2

## CPC

- C08F 222/00: Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- B01J 31/00: Catalysts comprising hydrides, coordination complexes or organic compounds (catalyst compositions used only in polymerisation reactions C08 {; catalytic antibodies C12N9/0002})
- C08F 222/103: {of trialcohols, e.g. trimethylolpropane tri(meth)acrylate}
- C08G 61/08: of carbocyclic compounds containing one or more carbon-to-carbon double bonds in the ring
- C08G 63/52: Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
- B01J 2231/543: alkene metathesis
- B01J 2531/64: Molybdenum
- B01J 2531/66: Tungsten
- B01J 2531/821: Ruthenium
- B01J 2531/825: Osmium
- C08G 2261/334: containing heteroatoms
- C08G 2261/418: Ring opening metathesis polymerisation [ROMP]
- C08G 2261/419: Acyclic diene metathesis [ADMET]
- C08G 2261/724: Hydrogenation
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS

## Abstract

Oligomers of certain glyceride compounds are generally disclosed herein. In some embodiments, the glyceride compounds include natural oil glycerides, such as glycerides derived from natural oils, such as palm oil, soybean oil, canola oil, and the like. Compositions containing such glyceride oligomers are also disclosed herein. Processes for making such glyceride oligomers are also disclosed herein. In some embodiments, the processes for making such compounds include reacting a plurality of unsaturated glyceride compounds in the presence of a metathesis catalyst.

## Claims

### Claim 1

A method of forming a glyceride copolymer, the method comprising:
(a) providing a reaction mixture comprising a first metathesis catalyst, unsaturated natural oil glycerides, and unsaturated alkenylized natural oil glycerides, wherein the number ratio of constitutional units formed from the unsaturated natural oil glycerides to constitutional units formed from the unsaturated alkenylized natural oil glycerides is no more than 10:1; and
(b) reacting the unsaturated natural oil glycerides and unsaturated alkenylized natural oil glycerides in the presence of the first metathesis catalyst to form the glyceride copolymer.

### Claim 2 (depends on 1)

The method of claim 1, wherein the unsaturated alkenylized natural oil glycerides are formed from the reaction of unsaturated natural oil glycerides with a short-chain alkene in the presence of a second metathesis catalyst.

### Claim 3 (depends on 2)

The method of claim 2, wherein the short-chain alkene is selected from the group consisting of ethylene, propylene, 1-butene, 2-butene, isobutene, 1-pentene, 2-pentene, 1-hexene, 2-hexene, and 3-hexene.

### Claim 4 (depends on 3)

The method of claim 3, wherein the short-chain alkene is selected from the group consisting of ethylene, propylene, 1-butene, 2-butene, and isobutene.

### Claim 5 (depends on 4)

The method of claim 4, wherein the short-chain alkene is ethylene.

### Claim 6 (depends on 4)

The method of claim 4, wherein the short-chain alkene is propylene.

### Claim 7 (depends on 4)

The method of claim 4, wherein the short-chain alkene is 1-butene.

### Claim 8 (depends on 4)

The method of claim 4, wherein the short-chain alkene is 2-butene.

### Claim 9 (depends on 1)

The method of claim 1, wherein the unsaturated natural oil glycerides are obtained from a natural oil.

### Claim 10 (depends on 9)

The method of claim 9, wherein the unsaturated natural oil glycerides are obtained from a vegetable oil.

### Claim 11 (depends on 10)

The method of claim 10, wherein the vegetable oil is selected from the group consisting of rapeseed oil, canola oil (low erucic acid rapeseed oil), coconut oil, corn oil, cottonseed oil, olive oil, palm oil, peanut oil, safflower oil, sesame oil, soybean oil, sunflower oil, linseed oil, palm kernel oil, tung oil, jatropha oil, mustard seed oil, pennycress oil, camelina oil, hempseed oil, and castor oil.

### Claim 12 (depends on 1)

The method of claim 1, wherein the glyceride copolymer has a number average molecular weight ranging from 4,000 g/mol to 150,000 g/mol.

### Claim 13 (depends on 1)

The method of claim 1, wherein the first metathesis catalyst is selected from the group consisting of an organoruthenium compound, an organoosmium compound, an organotungsten compound, and an organomolybdenum compound.

### Claim 14 (depends on 1)

The method of claim 1, wherein the second metathesis catalyst is selected from the group consisting of an organoruthenium compound, an organoosmium compound, an organotungsten compound, and an organomolybdenum compound.