Method for producing aromatic nitrile compound and method for producing carbonate ester

Patent metadata

Field	Value
Publication number	US-10584092-B2
Application number	US-201716310210-A
Country	US
Kind code	B2
Filing date	Jun 20, 2017
Priority date	Jun 22, 2016
Publication date	Mar 10, 2020
Grant date	Mar 10, 2020

Abstract

Provided is a method for regenerating an aromatic amide compound into a corresponding aromatic nitrile compound, the method realizing a dehydration reaction of providing a target compound selectively at a high yield with generation of a by-product being suppressed. Also provided is a method for producing an aromatic nitrile compound that decreases the number of steps of dehydration reaction and significantly improves the reaction speed at a pressure close to normal pressure. Furthermore, the above-described production method is applied to a carbonate ester production method to provide a method for producing carbonate ester efficiently. The above-described objects are achieved by a method for producing an aromatic nitrile compound including a dehydration reaction of dehydrating an aromatic amide compound, in which the dehydration reaction uses diphenylether.

First claim

The invention claimed is:

1. A method for producing an aromatic nitrile compound, comprising:
a dehydration reaction of dehydrating an aromatic amide compound;
wherein the dehydration reaction is performed in the presence of diphenylether.

2. The method for producing an aromatic nitrile compound according to claim 1 , wherein the dehydration reaction is performed in the presence of boiling diphenylether.

3. The method for producing an aromatic nitrile compound according to claim 2 , wherein the diphenylether has a boiling point that is higher than the boiling point of the aromatic nitrile compound and the boiling point of water and lower than the boiling point of the aromatic amide compound.

4. The method for producing an aromatic nitrile compound according to claim 1 , wherein the dehydration reaction is performed at a pressure of 2.7 kPa to 13.3 kPa.

5. The method for producing an aromatic nitrile compound according to claim 1 , wherein a reaction solution of the dehydration reaction has a temperature that is 170° C. or higher and lower than 230° C.

6. The method for producing an aromatic nitrile compound according to claim 1 , wherein the aromatic amide compound is selected from pyridine carboxamide or pyrazine amide, and the aromatic nitrile compound is selected from a corresponding cyanopyridine or cyanopyrazine.

7. The method for producing an aromatic nitrile compound according to claim 1 , wherein the dehydration reaction uses a catalyst containing cesium.

8. A method for producing a carbonate ester, comprising:
a first reaction step including a carbonate ester generation reaction of reacting one or more alcohol and carbon dioxide in the presence of an aromatic nitrile compound to generate a carbonate ester and water, and a hydration reaction of hydrating the aromatic nitrile compound with the generated water to generate an aromatic amide compound; and
a second reaction step of, after the aromatic amide compound is separated from a reaction system of the first reaction step, regenerating the aromatic amide compound into the aromatic nitrile compound by a dehydration reaction of dehydrating the aromatic amide compound in the presence of diphenylether;
wherein at least a part of the aromatic nitrile compound regenerated in the second reaction step is used in the first reaction step.

9. The method for producing a carbonate ester according to claim 8 , wherein the aromatic amide compound is selected from pyridine carboxamide or pyrazine amide, and the aromatic nitrile compound is selected from a corresponding cyanopyridine or cyanopyrazine.

10. The method for producing a carbonate ester according to claim 8 , wherein the dehydration reaction uses a catalyst containing cesium.

11. The method for producing a carbonate ester according to claim 8 , wherein the carbonate ester generation reaction uses a catalyst containing CeO 2 .

12. The method for producing a carbonate ester according to claim 8 , wherein the one or more alcohol has 1 to 6 carbons.

13. The method for producing a carbonate ester according to claim 8 , wherein the first reaction step uses a solvent having a boiling point higher than the boiling point of the aromatic amide compound to be generated.

14. The method for producing a carbonate ester according to claim 8 , wherein the solvent: contains at least one of a dialkylbenzene, an alkylnaphthalene, and a diphenylbenzene.

15. The method for producing a carbonate ester according to claim 8 , wherein the dehydration reaction of dehydrating the aromatic amide compound is performed at a temperature of 170° C. or higher and lower than 230° C.

Assignees

• Mitsubishi Gas Chemical Co
• Univ Tohoku
• Nippon Steel & Sumitomo Metal Corp
• Nippon Steel Eng Co Ltd
• Nippon Steel Corp

Inventors

• Shinkai Yousuke
• Liu Hongyu
• Harada Hidefumi
• Isahaya Yoshinori
• Tomishige Keiichi
• Nakagawa Yoshinao
• Tamura Masazumi
• Suzuki Kimihito
• Namiki Yasuki

Classifications

• C07D213/84 Primary

  Nitriles · CPC title

• C07D241/24

  Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals · CPC title

• C07C69/96

  Esters of carbonic or haloformic acids · CPC title

• C07C68/04 Primary

  from carbon dioxide or inorganic carbonates · CPC title

• C07B61/00

  Other general methods · CPC title