Method for manufacturing (meth) acrylic acid ester and method for manufacturing aromatic carboxylic acid ester
View Patent ↗Provided is a method capable of efficiently manufacturing (meth)acrylic acid esters and aromatic carboxylic acid esters. This (meth)acrylic acid ester manufacturing method reacts a (meth)acrylic anhydride with a carbonate compound. For this aromatic carboxylic acid ester manufacturing method, which reacts a carboxylic anhydride with an aromatic carbonate in the presence of a catalyst, the catalyst is at least one kind selected from a set consisting of basic nitrogen-containing organic compounds, Group 1 metal compounds, and Group 2 metal compounds.
1. A method for manufacturing a (meth)acrylic acid ester, comprising:
reacting (meth)acrylic anhydride and a carbonate compound,
wherein the carbonate compound has a carbonate group (—O—C(═O)—O—) bonded to a carbon atom in the molecule, and
wherein the reaction is carried out in the presence of at least one catalyst selected from the group consisting of a primary amine compound, a secondary amine compound, a tertiary amine compound, an aromatic amine compound, an imine compound, a nitrogen-comprising heterocyclic compound of formula (5), a nitrogen-comprising heterocyclic compound of formula (6), a nitrogen-comprising heterocyclic compound of formula (7), a Group I metal compound having ionic ligands consisting of organic molecules, and a Group II metal compound having ionic ligands consisting of organic molecules:
wherein, in formula (5):
the NR 21 R 22 group is bonded to any of the 2-, 3-, and 4-positions of the pyridine ring,
R 21 R 22 are each independently hydrogen; a linear, branched-chain or ring C1-C30 alkyl group, which may have a substituent; a linear, branched-chain or ring C2-C30 alkenyl group, which may have a substituent; or a C6-C30 aryl group, which may have a substituent, and
R 21 R 22 may be bonded to form a ring structure,
wherein, in formula (6):
the OR 23 group is bonded to any of the 2-, 3-, and 4-positions of the pyridine ring, and
R 23 is a linear, branched-chain or ring C1-C30 alkyl group, which may have a substituent; a linear, branched-chain or ring C2-C30 alkenyl group, which may have a substituent; or a C6-C30 aryl group, which may have a substituent,
wherein, in formula (7):
R 24 is a linear, branched-chain or ring C1-C30 alkyl group, which may have a substituent; a linear, branched-chain or ring C2-C30 alkenyl group, which may have a substituent; or a C6-C30 aryl group, which may have a substituent.
2. The method for manufacturing a (meth)acrylic acid ester according to claim 1 , wherein the reaction is carried out by using (meth)acrylic anhydride in a range of 0.1 mol-10 mol relative to 1 mol of the carbonate compound.
3. The method for manufacturing a (meth)acrylic acid ester according to claim 1 , wherein the reaction is carried out in the presence of a carboxylic acid in a range of 0.001 mol-1.5 mol relative to 1 mol of the carbonate compound.
4. The method for manufacturing a (meth)acrylic acid ester according to claim 1 , wherein the catalyst is at least one catalyst selected from the group consisting of the nitrogen-comprising heterocyclic compound of formula (5), the nitrogen-comprising heterocyclic compound of formula (6), and the nitrogen-comprising heterocyclic compound of formula (7).
5. The method for manufacturing a (meth)acrylic acid ester according to claim 1 , wherein the carbonate compound is diphenyl carbonate.
6. The method for manufacturing a (meth)acrylic acid ester according to claim 1 , wherein phenothiazine is present in the reaction mixture as a polymerization inhibitor.
7. The method for manufacturing a (meth)acrylic acid ester according to claim 1 , wherein part or all of the (meth)acrylic anhydride is added sequentially or continuously to the mixture containing the carbonate compound.
8. The method for manufacturing a (meth)acrylic acid ester according to claim 1 , wherein the reaction is carried out in the presence of a compound that contains a hydroxyl group in a range of 0.005 mass %-10 mass % relative to the reaction material.
9. The method for manufacturing a (meth)acrylic acid ester according to claim 1 , wherein the reaction temperature is set to be in a range of 40° C.-200° C.
10. A method for manufacturing an aromatic carboxylic acid ester, comprising:
reacting a carboxylic anhydride and an aromatic carbonate in the presence of a catalyst,
wherein the catalyst is at least one catalyst selected from the group consisting of a primary amine compound, a secondary amine compound, a tertiary amine compound, an aromatic amine compound, an imine compound, a nitrogen-comprising heterocyclic compound of formula (5), a nitrogen-comprising heterocyclic compound of formula (6), a nitrogen-comprising heterocyclic compound of formula (7), a Group I metal compound having ionic ligands consisting of organic molecules, and a Group II metal compound having ionic ligands consisting of organic molecules:
wherein, in formula (5):
the NR 21 R 22 group is bonded to any of the 2-, 3-, and 4-positions of the pyridine ring,
R 21 R 22 are each independently hydrogen; a linear, branched-chain or ring C1-C30 alkyl group, which may have a substituent; a linear, branched-chain or ring C2-C30 alkenyl group, which may have a substituent; or a C6-C30 aryl group, which may have a substituent, and
R 21 R 22 may be bonded to form a ring structure,
wherein, in formula (6):
the OR 23 group is bonded to any of the 2-, 3-, and 4-positions of the pyridine ring, and
R 23 is a linear, branched-chain or ring C1-C30 alkyl group, which may have a substituent; a linear, branched-chain or ring C2-C30 alkenyl group, which may have a substituent; or a C6-C30 aryl group, which may have a substituent,
wherein, in formula (7):
R 24 is a linear, branched-chain or ring C1-C30 alkyl group, which may have a substituent; a linear, branched-chain or ring C2-C30 alkenyl group, which may have a substituent; or a C6-C30 aryl group, which may have a substituent.
11. The method for manufacturing an aromatic carboxylic acid ester according to claim 10 , wherein the catalyst is at least one catalyst selected from the group consisting of the nitrogen-comprising heterocyclic compound of formula (5), the nitrogen-comprising heterocyclic compound of formula (6), and the nitrogen-comprising heterocyclic compound of formula (7).
12. The method for manufacturing an aromatic carboxylic acid ester according to claim 10 , wherein the aromatic carbonate is diphenyl carbonate.
13. The method for manufacturing an aromatic carboxylic acid ester according to claim 10 , wherein the carboxylic anhydride is either acrylic anhydride or methacrylic anhydride.
14. The method for manufacturing an aromatic carboxylic acid ester according to claim 10 , wherein the reaction temperature is set to be in a range of 40° C.-200° C.