# US 2020/0399423 A1 · High temperature metathesis chemistry

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- Number: US 2020/0399423 A1
- Document ID: US20200399423A1
- Status: Published application
- Kind: A1
- Application number: 15/930,632
- Filed: 2020-05-13
- Published: 2020-12-24
- Earliest claimed: 2017-08-15
- Assignees: University of Florida Research Foundation, Inc.
- Applicants: University of Florida Research Foundation, Incorporated
- Inventors: Kenneth B. WAGENER; Michael H. BELL
- Web page: https://patentgrep.com/patent/US20200399423A1

## CPC

- C08G 61/08: of carbocyclic compounds containing one or more carbon-to-carbon double bonds in the ring
- B01J 31/2208: {Oxygen, e.g. acetylacetonates}
- B01J 31/2273: {with only nitrogen as heteroatomic ring members, e.g. 1,3-diarylimidazoline-2-ylidenes}
- B01J 31/2278: {Complexes comprising two carbene ligands differing from each other, e.g. Grubbs second generation catalysts}
- C08G 61/12: Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08G 75/20: Polysulfones
- C08K 5/08: Quinones
- B01J 2231/14: Other (co) polymerisation, e.g. of lactides or epoxides
- B01J 2231/543: alkene metathesis
- B01J 2531/821: Ruthenium
- C08G 2261/122: statistical
- C08G 2261/344: containing heteroatoms
- C08G 2261/418: Ring opening metathesis polymerisation [ROMP]
- C08G 2261/419: Acyclic diene metathesis [ADMET]
- C08G 2261/724: Hydrogenation
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)

## Abstract

A method of carrying out a metathesis reaction includes the combination of at least one alkene or non conjugated diene with a Ruthenium-based catalyst with an cyclic(alkyl)(amino)carbene ligand to form a reaction mixture and heating the reaction mixture to a temperature of 100° C. or greater. The reaction can be an ADMET, ROMP, a metathesis ring-closure or an olefin exchange reaction.

## Claims

### Claim 1

A method of metathesis polymerization, comprising:
forming a polymerization mixture by combining
a Ruthenium-based catalyst comprising a cyclic(alkyl)(amino) carbene ligand, and
one or more selected from
at least one cyclic monomer comprising an alkene,
at least one linear monomer comprising an α,ω-dieneyl-monomer,
and combinations thereof;
heating the polymerization mixture to a temperature of 100° C. or greater.

### Claim 2 (depends on 1)

The method of metathesis polymerization according to claim 1, wherein the monomer comprises a functional group selected from alkyl, aryl, alkylaryl, ketone, aldehyde, ether, ester, carboxylic acid, alkylsilyl, arylsilyl, alkylarylsilyl, amine, epoxy, sulfone, sulfonic acid ester, and amides.

### Claim 3 (depends on 1)

The method of metathesis polymerization according to claim 1, wherein the temperature is 120° C. or greater.

### Claim 4 (depends on 1)

The method of metathesis polymerization according to claim 1, wherein the polymerization mixture further comprises a quinone.

### Claim 5 (depends on 4)

The method of metathesis polymerization according to claim 4, wherein the quinone is benzoquinone

### Claim 6 (depends on 1)

The method of metathesis polymerization according to claim 1, wherein the polymerization mixture further comprises a solvent having a boiling point in excess of the polymerization temperature at the polymerization pressure.

### Claim 7 (depends on 1)

The method of metathesis polymerization according to claim 1, wherein the catalyst is:

### Claim 8

A method of metathesis ring-closure, comprising:
combining at least one acyclic non-conjugated diene with a Ruthenium-based catalyst comprising an cyclic(alkyl)(amino)carbene ligand to form a reaction mixture; and
heating the reaction mixture to a temperature above 100° C.

### Claim 9 (depends on 8)

The method of metathesis ring-closure according to claim 8, wherein the non-conjugated diene comprises a functional group selected from alkyl, aryl, alkylaryl, ketone, aldehyde, ether, ester, carboxylic acid, alkylsilyl, arylsilyl, alkylarylsilyl, amine, epoxy, sulfone, sulfonic acid ester, and amides.

### Claim 10 (depends on 8)

The method of metathesis ring-closure according to claim 8, wherein the temperature is 120° C. or greater.

### Claim 11 (depends on 8)

The method of metathesis ring-closure according to claim 8, wherein the reaction mixture further comprises a quinone.

### Claim 12 (depends on 11)

The method of metathesis ring-closure according to claim 11, wherein the quinone is benzoquinone

### Claim 13 (depends on 8)

The method of metathesis ring-closure according to claim 8, wherein the polymerization mixture further comprises a solvent having a boiling point in excess of the polymerization temperature at the polymerization pressure.

### Claim 14 (depends on 8)

The method of metathesis ring-closure according to claim 8, wherein the catalyst is:

### Claim 15

A method of metathesis olefin exchange, comprising:
combining at least one alkene with a Ruthenium-based catalyst comprising an cyclic(alkyl(amino)carbene ligand to form a reaction mixture; and
heating the reaction mixture to a temperature above 100° C.

### Claim 16 (depends on 15)

The method of metathesis olefin exchange according to claim 15, wherein the alkene comprises a functional group selected from alkyl, aryl, alkylaryl, ketone, aldehyde, ether, ester, carboxylic acid, alkylsilyl, arylsilyl, alkylarylsilyl, amine, epoxy, sulfone, sulfonic acid ester, and amides.

### Claim 17 (depends on 15)

The method of metathesis olefin exchange according to claim 15, wherein the temperature is 120° C. or greater.

### Claim 18 (depends on 15)

The method of metathesis olefin exchange according to claim 15, wherein the reaction mixture further comprises a quinone.

### Claim 19 (depends on 18)

The method of metathesis olefin exchange according to claim 18, wherein the quinone is benzoquinone.