Method for manufacturing (meth) acrylic acid ester and method for manufacturing aromatic carboxylic acid ester

Patent metadata

Field	Value
Publication number	US-9796652-B2
Application number	US-201515308232-A
Country	US
Kind code	B2
Filing date	May 27, 2015
Priority date	Jun 12, 2014
Publication date	Oct 24, 2017
Grant date	Oct 24, 2017

Abstract

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.

First claim

What is claimed is:

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.

Assignees

• Mitsubishi Rayon Co
• Mitsubishi Chem Corp

Inventors

• Matsuo Takeshi
• Murata Naoshi
• Mori Hiroyuki

Classifications

• C07C67/11 Primary

  being mineral ester groups · CPC title

• C07C67/10 Primary

  by reacting carboxylic acids or symmetrical anhydrides with ester groups or with a carbon-halogen bond (preparation from carboxylic acid halides C07C67/14) · CPC title

• C07C69/54

  Acrylic acid esters; Methacrylic acid esters · CPC title

• C07C69/157

  containing six-membered aromatic rings · CPC title

• C07C69/78

  Benzoic acid esters · CPC title