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EP-4741384-A1 - FURONITRILE COMPOUND PRODUCTION METHOD AND CARBONATE ESTER PRODUCTION METHOD

EP4741384A1EP 4741384 A1EP4741384 A1EP 4741384A1EP-4741384-A1

Abstract

The present invention provides a method that makes it possible to selectively obtain a desired compound with high yield while shortening reaction time in regeneration of a nitrile compound by dehydration of an amide compound, and that also suppresses the generation of by-products. This problem is solved by a furonitrile compound production method comprising a dehydration reaction for dehydration of a furamide compound, wherein the dehydration reaction has a contact step for bringing a diluent and the furamide compound in a gaseous phase into contact with a catalyst. (In formula (1), R 1 and n are as defined in the description.)

Inventors

  • UMEZU Ryotaro
  • IMADA Shin-ichiro
  • SHINKAI YOUSUKE
  • HARADA HIDEFUMI
  • ISOBE TAKEHIKO

Assignees

  • MITSUBISHI GAS CHEMICAL COMPANY, INC.

Dates

Publication Date
20260513
Application Date
20240703

Claims (17)

  1. A method for producing a furonitrile compound, the method comprising a dehydration reaction represented by the following formula (1), in which a furamide compound is dehydrated, wherein the dehydration reaction has a contact step in which the furamide compound and a diluting agent are brought into contact with a catalyst in a gas phase: in formula (1), R 1 represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms and optionally having a substituent, an alkoxyl group having 1 to 20 carbon atoms and optionally having a substituent, a cycloalkyl group having 6 to 20 carbon atoms and optionally having a substituent, an aryl group having 6 to 20 carbon atoms and optionally having a substituent, a cycloalkoxyl group having 6 to 20 carbon atoms and optionally having a substituent, an aryloxy group having 6 to 20 carbon atoms and optionally having a substituent, or a cyclic compound group of a 3- to 20-membered ring containing at least two types of different elements and optionally having a substituent; and n represents an integer of 0 to 3.
  2. The method for producing a furonitrile compound according to claim 1, wherein R 1 is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 6 to 20 carbon atoms, or an aryl group having 6 to 20 carbon atoms.
  3. The method for producing a furonitrile compound according to claim 1, wherein a temperature at which the furamide compound and the diluting agent are brought into contact with the catalyst in the contact step is 150°C or higher.
  4. The method for producing a furonitrile compound according to claim 1, wherein a pressure in a reaction system in the contact step is 101.3 kPa or lower.
  5. The method for producing a furonitrile compound according to claim 1, wherein a contact time of the furamide compound with the catalyst in the gas phase is 0.001 seconds or longer and shorter than 10 seconds.
  6. The method for producing a furonitrile compound according to claim 1, wherein the catalyst comprises an alkali metal.
  7. The method for producing a furonitrile compound according to claim 1, wherein the diluting agent comprises at least any of a solvent and an inert gas.
  8. The method for producing a furonitrile compound according to claim 7, wherein the solvent comprises at least an aromatic compound.
  9. The method for producing a furonitrile compound according to claim 8, wherein the aromatic compound is represented by the following formula (2): wherein R 2 is each independently selected from an alkyl group having 1 to 10 carbon atoms and optionally having a substituent, an alkoxy group having 1 to 10 carbon atoms and optionally having a substituent, an aryl group having 6 to 30 carbon atoms and optionally having a substituent, and an aryl group having 6 to 30 carbon atoms and optionally having a substituent; and a is an integer of 1 to 6.
  10. The method for producing a furonitrile compound according to claim 8, wherein the aromatic compound has one or two aromatic rings and one or more selected from an alkyl group, an alkoxy group, and an aryloxy group.
  11. The method for producing a furonitrile compound according to claim 8, wherein the aromatic compound comprises at least any of phenyl ether, 1,3,5-trimethylbenzene, p-cymene, and anisole.
  12. The method for producing a furonitrile compound according to claim 7, wherein the solvent is compatible with the furamide compound.
  13. The method for producing a furonitrile compound according to claim 7, wherein an inert gas in a vaporized state is used in the contact step.
  14. The method for producing a furonitrile compound according to claim 7, wherein the inert gas comprises at least nitrogen gas.
  15. A method for producing a carbonate ester, the method comprising: a first reaction step that comprises a carbonate ester production reaction in which an alcohol is allowed to react with carbon dioxide in the presence of an furonitrile compound to produce a carbonate ester and water, and a hydration reaction in which the furonitrile compound is hydrated with the produced water to produce a furamide compound; and a second reaction step in which the furamide compound is separated from a reaction system of the first reaction step and then the furamide compound is regenerated into a furonitrile compound by means of a dehydration reaction in which the furamide compound is dehydrated, the dehydration reaction having the contact step according to any one of claims 1 to 14, wherein at least a part of the furonitrile compound regenerated in the second reaction step is used in the first reaction step.
  16. The method for producing a carbonate ester according to claim 15, wherein a catalyst comprising cerium oxide is used in the carbonate ester production reaction.
  17. The method for producing a carbonate ester according to claim 15, wherein the alcohol comprises an alcohol having 1 to 6 carbon atoms.

Description

TECHNICAL FIELD The present invention relates to a method for producing a furonitrile compound and a method for producing a carbonate ester. BACKGROUND ART The term carbonate ester collectively refers to compounds in which one or both of the two hydrogen atoms in carbonic acid, CO(OH)2, are substituted with an alkyl group or an aryl group, and which have a structure represented by RO-C(=O)OR' (where R and R' each represent a hydrogen atom, a saturated hydrocarbon group, an unsaturated hydrocarbon group, or the like). Carbonate esters are highly useful compounds that are used not only as additives, such as gasoline additives for improving the octane value and diesel fuel additives for decreasing particulate matter in exhaust gas, but also as alkylating agents, carbonylating agents, and solvents in the synthesis of resins and organic compounds such as polycarbonates, urethanes, pharmaceuticals, and agrochemicals. In addition, they are used as electrolytic solutions for lithium ion batteries, as raw materials for lubricating oils, and as raw materials for deoxidizing agents for preventing corrosion in boiler pipes. As conventional methods for producing a carbonate ester, for example, methods are known that include a step of allowing water, which is generated as a by-product in a reaction between an alcohol and carbon dioxide, to react with a nitrile compound (Patent Literatures 1 to 3 and the like). In such methods for producing a carbonate ester, a step is included in which the nitrile compound is regenerated by dehydrating an amide compound generated from the water and the nitrile compound. According to such conventional methods for producing a carbonate ester, the nitrile compound cannot necessarily be regenerated selectively in a short period of time and with high yield, and it has not been easy to efficiently produce a desired compound, the carbonate ester. PRIOR ART DOCUMENTS PATENT DOCUMENTS Patent Literature 1: WO 2015/099053Patent Literature 2: WO 2020/022416Patent Literature 3: WO 2022/181670 SUMMARY OF THE INVENTION PROBLEMS TO BE SOLVED BY THE INVENTION A main object of the present invention is to provide a method capable of selectively obtaining a desired compound with high yield while shortening the reaction time in the regeneration of a nitrile compound through dehydration of an amide compound, and also of suppressing the generation of by-products. Another main object of the present invention is to realize an efficient method for producing a carbonate ester by applying such a method for producing a nitrile compound. MEANS FOR SOLVING THE PROBLEMS The present inventors have studied a method for producing a furonitrile compound by dehydrating a furamide compound, and have found that, when the furamide compound and a diluting agent are brought into contact with a catalyst in a gas phase, the reaction rate can be significantly improved to shorten the reaction time, while suppressing the generation of by-products and selectively obtaining a desired compound with high yield. According to the present invention, the regeneration rate of a furonitrile compound from a furamide compound through a dehydration reaction can be improved. Also, in a method for producing a carbonate ester of the present invention using carbon dioxide and an alcohol, which incorporates such a dehydration reaction step, excellent effects can be achieved, such as enabling efficient production of the carbonate ester. For example, the present invention includes the following. [1] A method for producing a furonitrile compound, the method comprising a dehydration reaction represented by the following formula (1), in which a furamide compound is dehydrated, wherein the dehydration reaction has a contact step in which the furamide compound and a diluting agent are brought into contact with a catalyst in a gas phase: in formula (1), R1 represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms and optionally having a substituent, an alkoxyl group having 1 to 20 carbon atoms and optionally having a substituent, a cycloalkyl group having 6 to 20 carbon atoms and optionally having a substituent, an aryl group having 6 to 20 carbon atoms and optionally having a substituent, a cycloalkoxyl group having 6 to 20 carbon atoms and optionally having a substituent, an aryloxy group having 6 to 20 carbon atoms and optionally having a substituent, or a cyclic compound group of a 3- to 20-membered ring containing at least two types of different elements and optionally having a substituent; andn represents an integer of 0 to 3.[2] The method for producing a furonitrile compound according to the above [1], wherein R1 is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 6 to 20 carbon atoms, or an aryl group having 6 to 20 carbon atoms.[3] The method for producing a furonitrile compound according to the above [1] or [2], wherein a temperature at which the furamide compound and the diluting