Method for preparing (meth)acrylic acid ester based compound

1. A method for preparing a (meth)acrylic acid ester-based compound of the following Chemical Formula 1, comprising reacting an alcohol-based compound of the following Chemical Formula 2 and a (meth)acrylic acid-based compound of the following Chemical Formula 3, in the presence of a diamine-based compound of the following Chemical Formula 4 and an acid anhydride of the following Chemical Formula 5:

wherein in the Chemical Formulae 1 to 5,

R 11 to R 13 are each independently, hydrogen, substituted or unsubstituted C 1-20 alkyl, or substituted or unsubstituted C 3-20 cycloalkyl, or two neighboring functional groups are linked to form an alicyclic structure,

R 14 is hydrogen or methyl,

R 21 to R 24 are each independently, hydrogen, or substituted or unsubstituted C 1-10 alkyl,

R 25 is substituted or unsubstituted C 1-10 alkylene,

R 31 and R 32 are each independently, hydrogen or methyl,

R 41 and R 42 are each independently, substituted or unsubstituted C 1-10 alkylene,

m and n are each independently, an integer of 0 or 1, provided that when both m and n are 0, each of R 31 and R 32 is methyl.

2. The method according to claim 1 , wherein R 11 to R 13 are each independently, hydrogen, substituted or unsubstituted C 1-20 alkyl, or substituted or unsubstituted C 3-20 cycloalkyl, or two neighboring functional groups are linked to form an alicyclic structure, provided that two or more of R 11 to R 13 are not simultaneously hydrogen.

3. The method according to claim 1 , wherein the alcohol-based compound is a compound of the Chemical Formula 2 in which R 11 to R 13 are each independently C 1-6 linear or branched alkyl, or C 3-6 cycloalkyl; or a compound of the Chemical Formula 2 in which R 11 is hydrogen, and R 12 and R 13 are linked with each other to form a C 6-10 alicyclic structure unsubstituted or substituted with C 1-6 alkyl.

4. The method according to claim 1 , wherein the alcohol-based compound is butanol or menthol.

5. The method according to claim 1 , wherein the (meth)acrylic acid-based compound is acrylic acid.

6. The method according to claim 1 , wherein the (meth)acrylic acid-based compound is used at a mole ratio of 1 to 3, based on 1 mole of the alcohol-based compound.

7. The method according to claim 1 , wherein the diamine-based compound is a compound of the Chemical Formula 4, in which R 21 to R 24 are each independently, hydrogen; or C 1-10 alkyl unsubstituted or substituted with C 1-6 alkyl or C 3-6 cycloalkyl; and, R 25 is C 1-10 alkylene unsubstituted or substituted with C 1-6 alkyl or C 3-6 cycloalkyl.

8. The method according to claim 1 , wherein the diamine-based compound is N,N,N′,N′-tetramethylethylenediamine, N,N-dimethylethylene-1,2-diamine, N,N,N′,N′-tetramethylpropylenediamine, or N,N,N′,N′-tetramethylbutylenediamine.

9. The method according to claim 1 , wherein the diamine-based compound is used at a mole ratio of 0.5 to 1.5, based on 1 mole of the alcohol-based compound.

10. The method according to claim 1 , wherein the acid anhydride is a compound of the Chemical Formula 5, in which R 31 and R 32 are each independently, hydrogen or methyl, R 41 and R 42 are each independently, substituted or unsubstituted C 1-6 alkylene, and m and n are each independently, an integer of 0 or 1, provided that when both m and n are 0, each of R 31 and R 32 is methyl.

11. The method according to claim 1 , wherein the acid anhydride is acetic anhydride.

12. The method according to claim 1 , wherein the acid anhydride is used at a mole ratio of 1 to 1.5, based on 1 mole of the alcohol-based compound.

13. The method according to claim 1 , wherein:

(i) the alcohol-based compound and the (meth)acrylic acid-based compound are first combined to form a mixture;

(ii) the mixture is then mixed with the diamine-based compound, and reacted to form a reactant; and

(iii) the reactant is mixed with the acid anhydride, and reacted,

(i) and (ii) are conducted at a temperature of 0° C. or less, and

the (iii) is conducted at 50 to 80° C.

14. The method according to claim 13 , wherein the reactant obtained as the result of the (ii) comprises acryl-diaminoalkane cation.

15. The method according to claim 1 , further comprising an extraction purification process with hexane, after the reaction.