Preparation of (meth)acrylic acid esters
The invention relates to a method for preparation of (meth)acrylic acid esters from (meth)acrylic acid anhydrides. The method involves: reacting a (meth)acrylic acid anhydride of Formula (I): wherein R 1 is a hydrogen atom or a methyl group; with a substrate in the presence of a first catalyst to form a product mixture comprising the (meth)acrylic acid ester; and wherein: the substrate is selected from the group consisting of: primary alcohols; secondary alcohols; tertiary alcohols; and phenols; and the first catalyst comprises a salt of magnesium or of a rare earth element.
1. A process for the preparation of a (meth)acrylic acid ester, comprising at least step (a) as follows:
(a) reacting a (meth)acrylic acid anhydride of Formula (I):
wherein R 1 is a hydrogen atom or a methyl group;
with a substrate in the presence of a first catalyst to form a product mixture comprising the (meth)acrylic acid ester; and wherein:
the substrate is a primary alcohol having one hydroxyl group; and
the first catalyst comprises a halide of magnesium;
wherein the temperature during step (a) is kept between 60° C. and 90° C.
2. The process of claim 1 , wherein the first catalyst is selected from the group consisting of: magnesium bromide; magnesium iodide; and magnesium chloride.
3. The process of claim 1 , wherein the total amount of the first catalyst in step (a) is between 0.001 mol.-% and 10 mol.-% based on the amount of the substrate.
4. The process of claim 1 , wherein the total amount of the first catalyst in step (a) is between 0.01 mol.-% and 1.0 mol.-%, based on the amount of the substrate.
5. The process of claim 1 , wherein the molar ratio (meth)acrylic acid anhydride: substrate in step (a) is between 5:1 and 1:5.
6. The process of claim 1 , wherein the molar ratio (meth)acrylic acid anhydride: substrate in step (a) is between 3:1 and 1:3.
7. The process of claim 2 , wherein the total amount of the first catalyst in step (a) is between 0.001 mol.-% and 10 mol.-% based on the amount of the substrate.
8. The process of claim 7 , wherein the total amount of the first catalyst in step (a) is between 0.01 mol.-% and 1.0 mol.-%, based on the amount of the substrate.
9. The process of claim 2 , wherein the molar ratio (meth)acrylic acid anhydride: substrate in step (a) is between 5:1 and 1:5.
10. The process of claim 2 , wherein the molar ratio (meth)acrylic acid anhydride: substrate in step (a) is between 3:1 and 1:3.
11. A process for the preparation of a (meth)acrylic acid ester, comprising at least step (a) as follows:
(a) reacting a (meth)acrylic acid anhydride of Formula (I):
wherein R 1 is a hydrogen atom or a methyl group;
with a substrate in the presence of a first catalyst to form a product mixture comprising the (meth)acrylic acid ester; and wherein:
the substrate is a secondary alcohol having one hydroxyl group or a tertiary alcohol having one hydroxyl group; and
the first catalyst comprises a halide of magnesium;
wherein the temperature during step (a) is kept between 60° C. and 90° C.
12. The process of claim 11 , wherein the first catalyst is selected from the group consisting of: magnesium bromide; magnesium iodide; and magnesium chloride.
13. The process of claim 12 , wherein the reaction shows a conversion of greater than 18%.
14. The process of claim 11 , wherein the total amount of the first catalyst in step (a) is between 0.001 mol.-% and 10 mol.-% based on the amount of the substrate.
15. The process of claim 11 , wherein the total amount of the first catalyst in step (a) is between 0.01 mol.-% and 1.0 mol.-%, based on the amount of the substrate.
16. The process of claim 11 , wherein the molar ratio (meth)acrylic acid anhydride: substrate in step (a) is between 5:1 and 1:5.
17. The process of claim 11 , wherein the molar ratio (meth)acrylic acid anhydride:
substrate in step (a) is between 3:1 and 1:3.
18. The process of claim 11 , wherein the substrate is a secondary alcohol having one hydroxyl group.
19. The process of claim 11 , wherein the substrate is a tertiary alcohol having one hydroxyl group.