Preparation of (meth)acrylic acid esters
The invention relates to a method for preparation of (meth)acrylic acid esters from (meth)acrylic acid anhydrides. Wherein the method for preparation of the (meth)acrylic acid ester, comprises 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 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 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 selected from the group consisting of: a primary alcohol with one hydroxyl group, a secondary alcohol with one hydroxyl group, and a tertiary alcohol with one hydroxyl group; and
the first catalyst is magnesium bromide;
wherein the temperature during step (a) is kept between 40° C. and 110° C. and wherein the reaction has a conversion of greater than 18%;
and further comprising steps (b) and (c) which are carried out after step (a):
(b) adding an auxiliary alcohol to the product mixture obtained in step (a), wherein a product mixture comprising the (meth)acrylic acid ester and a (meth)acrylic acid ester of the auxiliary alcohol is formed; and
(c) removing the (meth)acrylic acid ester of the auxiliary alcohol from the product mixture obtained in step (b).
2. The process of claim 1 , wherein the molar ratio of (meth)acrylic acid anhydride to substrate is between 1.5:1 and 1:1.5.
3. The process of claim 1 , wherein the molar ratio of (meth)acrylic acid anhydride: substrate in step (a) is between 5:1 and 1:5.
4. The process of claim 1 , wherein the molar ratio of (meth)acrylic acid anhydride: substrate in step (a) is between 3:1 and 1:3.
5. The process of claim 1 , wherein the auxiliary alcohol is a primary or secondary alcohol having a boiling point of not more than 150° C. measured at 10 5 Pa.
6. The process of claim 5 , wherein the auxiliary alcohol is selected from methanol, ethanol, n-propanol, iso-propanol or a mixture thereof.
7. The process of claim 5 , wherein the auxiliary alcohol is methanol.
8. The process of claim 5 , wherein the auxiliary alcohol is a primary or secondary alcohol having a boiling point of not more than 120° C. measured at 10 5 Pa.
9. The process of claim 5 , wherein the auxiliary alcohol is a primary or secondary alcohol having a boiling point of not more than 80° C. measured at 10 5 Pa.
10. The process of claim 5 , wherein, in step (c), the (meth)acrylic acid ester of the auxiliary alcohol is removed from the product mixture by distillation.
11. The process of claim 3 , wherein the auxiliary alcohol is a primary or secondary alcohol having a boiling point of not more than 120° C. measured at 10 5 Pa.
12. The process of claim 1 , wherein step (a) is carried out in the absence of any solvent.
13. The process of claim 1 , wherein the reaction has a conversion of greater than 35%.
14. The process of claim 13 , wherein step (a) is carried out in the absence of any solvent.
15. The process of claim 13 , wherein the molar ratio of (meth)acrylic acid anhydride: substrate in step (a) is between 5:1 and 1:5.
16. The process of claim 13 , wherein the molar ratio of (meth)acrylic acid anhydride: substrate in step (a) is between 3:1 and 1:3.
17. The process of claim 13 , wherein the auxiliary alcohol is a primary or secondary alcohol having a boiling point of not more than 150° C. measured at 10 5 Pa.
18. The process of claim 17 , wherein the auxiliary alcohol is selected from methanol, ethanol, n-propanol, iso-propanol or a mixture thereof.