Method for producing methacrylic acid ester

Patent metadata

Field	Value
Publication number	US-9682915-B2
Application number	US-201414780232-A
Country	US
Kind code	B2
Filing date	Mar 19, 2014
Priority date	Mar 26, 2013
Publication date	Jun 20, 2017
Grant date	Jun 20, 2017

Abstract

Production of methacrylic acid ester comprising a step of having acetone undergo a dehydration reaction in the presence of a dehydration reaction catalyst to obtain a reaction mixture; a step of separating a mixture containing propyne and propadiene as main components from the obtained reaction mixture; a step of separating the separated mixture containing propyne and propadiene as main components into a liquid, gas, or gas-liquid mixture containing propyne as a main component, and a liquid, gas, or gas-liquid mixture containing propadiene as a main component; and a step of bringing the obtained liquid, gas, or gas-liquid mixture containing propyne as a main component into contact with carbon monoxide and an alcohol having 1 to 3 carbon atoms in the presence of a catalyst containing at least one selected from the group consisting of Group 8 metal elements, Group 9 metal elements, and Group 10 metal elements.

First claim

The invention claimed is:

1. A method for producing a methacrylic acid ester, which comprises the following steps:
a dehydration reaction step: a step of having acetone undergo a dehydration reaction in the presence of a dehydration reaction catalyst to obtain a reaction mixture containing propyne, propadiene, and water;
a propyne/propadiene separation step: a step of separating a mixture containing propyne and propadiene as main components from the reaction mixture obtained in the dehydration reaction step;
a propyne purification step: a step of separating the mixture containing propyne and propadiene as main components separated in the propyne/propadiene separation step into a liquid, gas, or gas-liquid mixture containing propyne as a main component, and a liquid, gas, or gas-liquid mixture containing propadiene as a main component; and
a carbonylation reaction step: a step of bringing the liquid, gas, or gas-liquid mixture containing propyne as a main component obtained in the propyne purification step into contact with carbon monoxide and an alcohol having 1 to 3 carbon atoms in the presence of a catalyst containing at least one selected from the group consisting of Group 8 metal elements, Group 9 metal elements, and Group 10 metal elements to obtain a methacrylic acid ester; and
wherein the dehydration reaction catalyst is a catalyst containing silicon and at least one selected from the group consisting of Group 1 metal elements and Group 2 metal elements.

2. The method according to claim 1 , wherein the reaction mixture in the dehydration reaction step further contains unreacted acetone, and in the propyne/propadiene separation step, a mixture containing the unreacted acetone is obtained by separating the mixture containing propyne and propadiene as main components.

3. The method according to claim 2 , further comprising the following step:
an acetone circulation step: a step of supplying at least a part of acetone contained in the mixture containing the unreacted acetone obtained in the propyne/propadiene separation step to the dehydration reaction step.

4. The method according to claim 1 , further comprising the following step:
an isomerization reaction step: a step of isomerizing the liquid, gas, or gas-liquid mixture containing propadiene as a main component obtained in the propyne purification step in the presence of an isomerization catalyst to obtain a mixture containing propyne and propadiene as main components.

5. The method according to claim 1 , further comprising the following step:
a methacrylic acid ester purification step: a step of recovering propyne and an alcohol having 1 to 3 carbon atoms from the reaction mixture containing the methacrylic acid ester obtained in the carbonylation reaction step, the unreacted propyne, and the unreacted alcohol having 1 to 3 carbon atoms, and also purifying the methacrylic acid ester.

6. The method according to claim 5 , further comprising the following step:
an alcohol circulation step: a step of supplying at least a part of the alcohol having 1 to 3 carbon atoms obtained in the methacrylic acid ester purification step to the carbonylation reaction step.

Assignees

• Sumitomo Chemical Co

Inventors

• Seki Kohei
• Suzuta Tetsuya
• Miura Naoki

Classifications

• C07C2521/08

  Silica · CPC title

• C07C69/54

  Acrylic acid esters; Methacrylic acid esters · CPC title

• C07C67/38 Primary

  by addition to an unsaturated carbon-to-carbon bond · CPC title

• Y02P20/582

  Recycling of unreacted starting or intermediate materials · CPC title

• C07C11/24

  Acetylene (production of acetylene gas by wet methods C10H) · CPC title