Method for producing aromatic nitrile compound and method for producing carbonic acid ester

Patent metadata

Field	Value
Publication number	US-10793524-B2
Application number	US-201716470817-A
Country	US
Kind code	B2
Filing date	Nov 30, 2017
Priority date	Dec 21, 2016
Publication date	Oct 6, 2020
Grant date	Oct 6, 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 the dehydration reaction and significantly improves the reaction speed even at a pressure close to normal pressure. In addition, the above-described production method is applied to a carbonate ester production method to provide a method for producing a carbonate ester efficiently. The above-described methods are realized 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, as a solvent, any of 1,2-dimethoxybenzene, 1,3-dimethoxybenzene and 1,3,5-trimethoxybenzene.

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 uses a solvent comprising one or a plurality of substances selected from 1,2-dimethoxybenzene, 1,3-dimethoxybenzene and 1,3,5-trimethoxybenzene.

2. The method for producing an aromatic nitrile compound according to claim 1 , wherein a total amount of the one or the plurality of substances selected from 1,2-dimethoxybenzene, 1,3-dimethoxybenzene and 1,3,5-trimethoxybenzene is 5% by weight or greater with respect to the solvent.

3. The method for producing an aromatic nitrile compound according to claim 1 , wherein the solvent is formed of only the one or the plurality of substances selected from 1,2-dimethoxybenzene, 1,3-dimethoxybenzene and 1,3,5-trimethoxybenzene.

4. The method for producing an aromatic nitrile compound according to claim 1 , wherein the solvent is a mixed solvent further comprising a compound having a boiling point that is higher than the boiling point of the aromatic nitrile compound and the boiling point of water and is lower than the boiling point of the aromatic amide compound.

5. The method for producing an aromatic nitrile compound according to claim 1 , wherein the solvent is used in an amount larger than, or equal to, an equimolecular amount of the aromatic amide compound.

6. The method for producing an aromatic nitrile compound according to claim 1 , wherein the dehydration reaction is performed in a state where the solvent is boiled.

7. The method for producing an aromatic nitrile compound according to claim 1 , wherein the dehydration reaction is performed under the condition of normal pressure or a reduced pressure.

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

9. The method for producing an aromatic nitrile compound according to claim 1 , wherein the aromatic amide compound comprises pyridine carboamide, and the aromatic nitrile compound comprises cyanopyridine.

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

11. A method for producing a carbonate ester, comprising:
a first reaction step including a carbonate ester generation reaction of reacting an 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 an aromatic nitrile compound by a dehydration reaction of dehydrating the aromatic amide compound in a solvent comprising one or a plurality of substances selected from 1,2-dimethoxybenzene, 1,3-dimethoxybenzene and 1,3,5-trimethoxybenzene;
wherein at least a part of the aromatic nitrile compound regenerated in the second reaction step is used in the first reaction step.

12. The method for producing a carbonate ester according to claim 11 , wherein a total amount of the one or the plurality of substances selected from 1,2-dimethoxybenzene, 1,3-dimethoxybenzene and 1,3,5-trimethoxybenzene is 5% by weight or greater with respect to the solvent.

13. The method for producing an aromatic nitrile compound according to claim 11 , wherein the solvent is formed of only the one or the plurality of substances selected from 1,2-dimethoxybenzene, 1,3-dimethoxybenzene and 1,3,5-trimethoxybenzene.

14. The method for producing a carbonate ester according to claim 11 , wherein the solvent is a mixed solvent further comprising a compound having a boiling point that is higher than the boiling point of the aromatic nitrile compound and the boiling point of water and is lower than the boiling point of the aromatic amide compound.

15. The method for producing a carbonate ester according to claim 11 , wherein the solvent is used in an amount larger than, or equal to, an equimolecular amount of the aromatic amide compound.

16. The method for producing a carbonate ester according to claim 11 , wherein the dehydration reaction is performed in a state where the solvent is boiled.

17. The method for producing a carbonate ester according to claim 11 , wherein the dehydration reaction is performed under the condition of normal pressure or a reduced pressure.

18. The method for producing a carbonate ester according to claim 11 , wherein a reaction solution of the dehydration reaction has a temperature of 170° C. or higher and lower than 230° C.

19. The method for producing a carbonate ester according to claim 11 , wherein the aromatic amide compound comprises pyridine carboamide, and the aromatic nitrile compound comprises cyanopyridine.

20. The method for producing a carbonate ester according to claim 11 , wherein the dehydration reaction uses a catalyst comprising cesium.

21. The method for producing a carbonate ester according to claim 11 , wherein the carbonate ester generation reaction uses a catalyst comprising cerium.

22. The method for producing a carbonate ester according to claim 11 , wherein the alcohol comprises an alcohol having a carbon number of 1 to 6.

Assignees

• Mitsubishi Gas Chemical Co

Inventors

• Harada Hidefumi
• Shinkai Yousuke
• Liu Hongyu
• Isobe Takehiko
• Isahaya Yoshinori

Classifications

• C07D213/84 Primary

  Nitriles · CPC title

• C07C69/96

  Esters of carbonic or haloformic acids · CPC title

• C07C68/04

  from carbon dioxide or inorganic carbonates · CPC title

• C07B61/00

  Other general methods · CPC title

• B01J37/0236

  Drying, e.g. preparing a suspension, adding a soluble salt and drying · CPC title