Method for producing N-(alpha-alkoxyethyl)formamide

Patent metadata

Field	Value
Publication number	US-10899701-B2
Application number	US-201916242032-A
Country	US
Kind code	B2
Filing date	Jan 8, 2019
Priority date	Aug 12, 2016
Publication date	Jan 26, 2021
Grant date	Jan 26, 2021

Abstract

Provided are a method for producing N-(α-alkoxyethyl)formamide, comprising adding an acid catalyst to the mixed liquid within 3 hours from start of mixing after mixing of N-(α-hydroxyethyl)formamide with an alcohol has been started, by which the N-(α-alkoxyethyl)formamide can be produced at a high yield without additional investment in plant and equipment while suppressing an increase in the temperature of the mixed liquid and preventing corrosion of a pipe; and a method for producing N-(α-alkoxyethyl)formamide, comprising degassing carbon dioxide in the reaction of N-(α-hydroxyethyl)formamide with an alcohol, by which the N-(α-alkoxyethyl)formamide having a decreased carbonate concentration can be produced.

First claim

The invention claimed is:

1. A method for producing N-(α-alkoxyethyl)formamide, comprising:
production of N-(α-hydroxyethyl)formamide by mixing formamide with acetaldehyde in presence of a carbonate and precipitating N-(α-hydroxyethyl)formamide; and
production of the N-(α-alkoxyethyl)formamide by first mixing the N-(α-hydroxyethyl)formamide with an alcohol to form a mixed liquid,
then adding an acid catalyst to the mixed liquid containing the N-(α-hydroxyethyl)formamide and the alcohol within 3 hours from when the mixing of the N-(α-hydroxyethyl)formamide with the alcohol is started in the production of the N-(α-alkoxyethyl)formamide,
wherein carbon dioxide in a reaction liquid is degassed in the production of the N-(α-alkoxyethyl)formamide when the reaction liquid is under an acidic condition.

2. The method for producing N-(α-alkoxyethyl)formamide according to claim 1 , wherein the acid catalyst is added to the mixed liquid containing the N-(α-hydroxyethyl)formamide and the alcohol after 1 minute or more and within 3 hours from when the mixing of the N-(α-hydroxyethyl)formamide with the alcohol is started in the production of the N-(α-alkoxyethyl)formamide.

3. The method for producing N-(α-alkoxyethyl)formamide according to claim 1 , wherein a temperature of the mixed liquid containing the N-(α-hydroxyethyl)formamide and the alcohol immediately before addition of the acid catalyst is 30° C. or less.

4. The method for producing N-(α-alkoxyethyl)formamide according to claim 3 , wherein a temperature of the mixed liquid containing the N-(α-hydroxyethyl)formamide and the alcohol immediately before addition of the acid catalyst is 10° C. or less.

5. The method for producing N-(α-alkoxyethyl)formamide according to claim 1 , wherein a carbonate ion concentration in a solution that is obtained by neutralizing a reaction mixture obtained in the production of the N-(α-alkoxyethyl)formamide with a base and subjecting the reaction mixture neutralized to solid-liquid separation and contains the N-(α-alkoxyethyl)formamide is 500 ppm or less.

6. The method for producing N-(α-alkoxyethyl)formamide according to claim 1 , wherein the degassing of carbon dioxide is conducted by blowing of an inert gas into the reaction liquid.

7. The method for producing N-(α-alkoxyethyl)formamide according to claim 6 , wherein a linear velocity of the inert gas in the blowing of an inert gas is from 0.1 to 20 m/hr.

Assignees

• Mitsubishi Chem Corp

Inventors

• Teramoto Kouji
• Mori Yasuharu
• Nishimura Hitoshi

Classifications

• C07C231/08

  from amides by reaction at nitrogen atoms of carboxamide groups · CPC title

• C07C231/12 Primary

  by reactions not involving the formation of carboxamide groups · CPC title

• C07C231/24

  Separation; Purification · CPC title

• C07C233/18

  having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton · CPC title