# US 11,028,038 B2 · Preparation method of acrylic ester compound

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- Number: US 11,028,038 B2
- Document ID: US11028038B2
- Status: Granted
- Kind: B2
- Application number: 16/626,072
- Filed: 2019-05-15
- Published: 2020-12-31
- Granted: 2021-06-08
- Earliest claimed: 2018-11-27
- Assignees: LG Chem, Ltd.
- Applicants: LG Chem, Ltd.
- Inventors: Ji Eun Kim; Won Taeck Lim; Yongjin Kim; Wonmun Choi
- Web page: https://patentgrep.com/patent/US11028038B2

## CPC

- C07C 67/08: by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
- B01J 31/02: containing organic compounds or metal hydrides
- B01J 31/0238: {with a primary amino group}
- C07C 67/02: by interreacting ester groups, i.e. transesterification
- C07C 69/602: Dicarboxylic acid esters having at least two carbon-to-carbon double bonds
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS

## Abstract

The present disclosure relates to a preparation method of an acrylic ester compound. The preparation method of an acrylic ester compound according to the present disclosure enables the use of acrylic anhydride as a reactant instead of acryloyl chloride, which is difficult to handle, by using an alkane diamine as a catalyst. Therefore, not only can the reaction be carried out at a low temperature, but also conversion to an acrylic ester compound and a yield of the acrylic ester compound can be improved.

## Claims

### Claim 1

A preparation method of an acrylic ester compound represented by the following Chemical Formula 4, comprising a step of reacting a compound represented by the following Chemical Formula 1 with a compound represented by the following Chemical Formula 2 in the presence of a catalyst represented by the following Chemical Formula 3:
wherein, in Chemical Formula 1,
R1 is a substituted or unsubstituted C1-30 alkylene, a substituted or unsubstituted C2-30 alkenylene, or a substituted or unsubstituted C2-30 alkynylene, and
R2 and R3 are each independently hydrogen or a C1-20 alkyl,
wherein, in Chemical Formula 2,
R4 and R5 are each independently hydrogen or a methyl,
wherein, in Chemical Formula 3,
R6 to R9 are each independently hydrogen or a substituted or unsubstituted C1-10 alkyl, and
R10 is a substituted or unsubstituted C1-10 alkylene,
wherein, in Chemical Formula 4,
R1 to R5 are as defined above.

### Claim 2 (depends on 1)

The preparation method of claim 1,
wherein the R1 is a substituted or unsubstituted C1-10 alkylene, a substituted or unsubstituted C2-10 alkenylene, or a substituted or unsubstituted C2-10 alkynylene.

### Claim 3 (depends on 1)

The preparation method of claim 1,
wherein the R2 and R3 are each independently a C1-5 alkyl.

### Claim 4 (depends on 3)

The preparation method of claim 3,
wherein the R2 and R3 are methyl.

### Claim 5 (depends on 1)

The preparation method of claim 1,
wherein the R4 and R5 are hydrogen.

### Claim 6 (depends on 1)

The preparation method of claim 1,
wherein the R6 to R9 are each independently a substituted or unsubstituted C1-10 alkyl.

### Claim 7 (depends on 1)

The preparation method of claim 1,
wherein the R6 and R7 are methyl, and
R8 and R9 are hydrogen or methyl.

### Claim 8 (depends on 1)

The preparation method of claim 1,
wherein the R10 is a substituted or unsubstituted C1-5 alkylene.

### Claim 9 (depends on 8)

The preparation method of claim 8,
wherein the R10 is ethylene.

### Claim 10 (depends on 1)

The preparation method of claim 1,
wherein Chemical Formula 1 is any one of the following Chemical Formulae 1-1 to 1-4:

### Claim 11 (depends on 1)

The preparation method of claim 1,
wherein the compound represented by Chemical Formula 2 is acrylic anhydride.

### Claim 12 (depends on 1)

The preparation method of claim 1,
wherein the catalyst represented by Chemical Formula 3 is N,N,N′,N′-tetramethylethylenediamine or N,N-dimethylethane-1,2-diamine.

### Claim 13 (depends on 1)

The preparation method of claim 1,
wherein the reaction is carried out at a temperature of 30° C. to 80° C.

### Claim 14 (depends on 1)

The preparation method of claim 1,
wherein conversion of the reaction is 90 to 99.9% and a yield of the reaction is 70 to 95% a.

### Claim 15 (depends on 1)

The preparation method of claim 1,
wherein the R1 is any one selected from the group consisting of 2-methyl-1-pentenylene, 3,3-dimethyl-1-propynylene, propylene, and methyl ethylene.

### Claim 16 (depends on 1)

The preparation method of claim 1, wherein 2.1 to 3.5 equivalents of the compound represented by Chemical Formula 2 and 0.05 to 0.5 equivalents of the compound represented by Chemical Formula 3 are reacted based on 1 equivalent of the compound represented by Chemical Formula 1.

### Claim 17 (depends on 1)

The preparation method of claim 1, wherein the step of reacting the compound represented by Chemical Formula 1 with the compound represented by Chemical Formula 2 is carried out from 4 hours to 24 hours.