Preparation method of acrylic ester compound

Patent metadata

Field	Value
Publication number	US-11028038-B2
Application number	US-201916626072-A
Country	US
Kind code	B2
Filing date	May 15, 2019
Priority date	Nov 27, 2018
Publication date	Jun 8, 2021
Grant date	Jun 8, 2021

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.

First claim

What is claimed is:

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,
R 1 is a substituted or unsubstituted C 1-30 alkylene, a substituted or unsubstituted C 2-30 alkenylene, or a substituted or unsubstituted C 2-30 alkynylene, and
R 2 and R 3 are each independently hydrogen or a C 1-20 alkyl,

wherein, in Chemical Formula 2,
R 4 and R 5 are each independently hydrogen or a methyl,

wherein, in Chemical Formula 3,
R 6 to R 9 are each independently hydrogen or a substituted or unsubstituted C 1-10 alkyl, and
R 10 is a substituted or unsubstituted C 1-10 alkylene,

wherein, in Chemical Formula 4,
R 1 to R 5 are as defined above.

2. The preparation method of claim 1 ,
wherein the R 1 is a substituted or unsubstituted C 1-10 alkylene, a substituted or unsubstituted C 2-10 alkenylene, or a substituted or unsubstituted C 2-10 alkynylene.

3. The preparation method of claim 1 ,
wherein the R 2 and R 3 are each independently a C 1-5 alkyl.

4. The preparation method of claim 3 ,
wherein the R 2 and R 3 are methyl.

5. The preparation method of claim 1 ,
wherein the R 4 and R 5 are hydrogen.

6. The preparation method of claim 1 ,
wherein the R 6 to R 9 are each independently a substituted or unsubstituted C 1-10 alkyl.

7. The preparation method of claim 1 ,
wherein the R 6 and R 7 are methyl, and
R 8 and R 9 are hydrogen or methyl.

8. The preparation method of claim 1 ,
wherein the R 10 is a substituted or unsubstituted C 1-5 alkylene.

9. The preparation method of claim 8 ,
wherein the R 10 is ethylene.

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

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

12. 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.

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

14. 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.

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

16. 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.

17. 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.

Assignees

• Lg Chemical Ltd

Inventors

• Kim Ji Eun
• Lim Won Taeck
• Kim Yongjin
• Choi Wonmun

Classifications

• C07C69/602

  Dicarboxylic acid esters having at least two carbon-to-carbon double bonds · CPC title

• C07C67/08 Primary

  by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds · CPC title

• B01J31/0237

  Amines · CPC title

• C07C67/02

  by interreacting ester groups, i.e. transesterification · CPC title

• B01J31/0238

  with a primary amino group · CPC title