US11299454B2 · US · B2
| Field | Value |
|---|---|
| Publication number | US-11299454-B2 |
| Application number | US-201715999787-A |
| Country | US |
| Kind code | B2 |
| Filing date | Jan 16, 2017 |
| Priority date | Feb 22, 2016 |
| Publication date | Apr 12, 2022 |
| Grant date | Apr 12, 2022 |
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A method for producing an N-vinylcarboxylic acid amide is provided, the method focusing on unsaturated aldehydes that are contained as impurities generated during a reaction. The method for producing an N-vinylcarboxylic acid amide includes a step for controlling the contained amount of unsaturated aldehydes in the N-vinylcarboxylic acid amide to be not more than 20 mass ppm.
Opening claim text (preview).
The invention claimed is: 1. A method of producing N-vinylcarboxylic acid amide, comprising: a step of obtaining N-vinylcarboxylic acid amide by using the de-alcoholization reaction from N-(1-alkoxyethyl) carboxylic acid amide, wherein the N-(1-alkoxyethyl) carboxylic acid amide is a compound represented by the following general formula (I), wherein R 1 represents an alkyl group having 1 to 5 carbon atoms, R 2 independently represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, and R 3 represents an alkyl group having 1 to 5 carbon atoms; and a step of controlling an amount of unsaturated aldehydes in N-vinylcarboxylic acid amide to 20 mass ppm or less, wherein the step of controlling an amount of unsaturated aldehydes comprises steps of obtaining a second crude N-(1-alkoxyethyl) carboxylic acid amide by adjusting a pH of a first crude N-(1-alkoxyethyl) carboxylic acid amide to 8.0 to 8.5 by using 30 to 48% by mass of one selected from the group consisting of a sodium hydroxide aqueous solution and a potassium hydroxide aqueous solution; and purifying the N-(1-alkoxyethyl) carboxylic acid amide by distilling the second crude N-(1-alkoxyethyl) carboxylic acid amide. 2. The method of producing N-vinylcarboxylic acid amide according to claim 1 , further comprising: a step of producing the N-(1-alkoxyethyl) carboxylic acid amide from carboxylic acid amide, acetaldehyde and alcohol; or from carboxylic acid amide and acetaldehyde dialkyl acetal. 3. The method of producing N-vinylcarboxylic acid amide according to claim 1 , wherein the N-vinylcarboxylic acid amide is a N-vinylacetamide. 4. The method of producing N-vinylcarboxylic acid amide according to claim 1 , wherein the unsaturated aldehydes comprises at least one selected from the group consisting of crotonaldehyde, 2-ethyl-2-butenal, 2-methyl-2-pentenal, 2-hexenal, 2,4-hexadienal, 2,4-octadienal, 2,4,6-octatrienal, and trans-2-octenal, and an amount of the unsaturated aldehyde is a total amount of crotonaldehyde, 2-ethyl-2-butenal, 2-methyl-2-pentenal, 2-hexenal, 2,4-hexadienal, 2, 4-octadienal, 2,4,6-octatrienal and trans-2-octenal. 5. The method of producing N-vinylcarboxylic acid amide according to claim 1 , wherein the N-vinylcarboxylic acid amide is purified by crystallization.
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
Separation; Purification · CPC title
from amides by reaction at nitrogen atoms of carboxamide groups · CPC title
Platinum · CPC title
by reactions not involving the formation of carboxamide groups · CPC title
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