Method for producing 2-aminoethylmethacrylate hydrochloride

Patent metadata

Field	Value
Publication number	US-9988342-B2
Application number	US-201615546479-A
Country	US
Kind code	B2
Filing date	Jan 26, 2016
Priority date	Feb 4, 2015
Publication date	Jun 5, 2018
Grant date	Jun 5, 2018

Abstract

Provided is a method for producing 2-aminoethyl methacrylate hydrochloride that, according to one embodiment, includes a step (A) for reacting a ketimine compound of 2-aminoethyl methacrylate with water and hydrogen chloride and obtaining a mixture containing 2-aminoethyl methacrylate hydrochloride, wherein in the step (A), the ratio of the total amount of hydrogen chloride to the total amount of ketimine compound of 2-aminoethyl methacrylate is 1.0-1.5 expressed in terms of equivalents, and the ratio of the total amount of water to the total amount of ketimine compound of 2-aminoethyl methacrylate is 1.0-2.0 expressed in terms of equivalents.

First claim

The invention claimed is:

1. A method for producing 2-aminoethyl methacrylate hydrochloride, comprising (A) reacting a ketimine compound of 2-aminoethyl methacrylate represented by Formula (1) or (2) below,

wherein, in Formula (1), R 1 and R 2 each independently represent an alkyl group or an aryl group with a carbon number of 1-12,

wherein, in Formula (2), R 3 represents a bivalent hydrocarbon group with a carbon number of 3-10 that forms a ring with a carbon atom to which it binds, and may partly have a double bond,
with water and hydrogen chloride to obtain a mixture containing 2-aminoethyl methacrylate hydrochloride represented by Formula (3) below,

wherein, in (A), the ratio of the whole amount of hydrogen chloride to the whole amount of the ketimine compound of 2-aminoethyl methacrylate is in a range of 1.0-1.5 in equivalent ratio, and the ratio of the whole amount of water to the whole amount of the ketimine compound of 2-aminoethyl methacrylate is in a range of 1.0-2.0 in equivalent ratio.

2. The method for producing 2-aminoethyl methacrylate hydrochloride according to claim 1 , wherein R 1 and R 2 in Formula (1) above each independently represent an alkyl group with a carbon number of 1-4.

3. The method for producing 2-aminoethyl methacrylate hydrochloride according to claim 2 , wherein, in Formula (1) above, R 1 represents a methyl group and R 2 represents an ethyl group or an isobutyl group.

4. The method for producing 2-aminoethyl methacrylate hydrochloride according to claim 3 , wherein R 2 in Formula (1) above represents an isobutyl group.

5. The method for producing 2-aminoethyl methacrylate hydrochloride according to claim 3 , wherein R 2 in Formula (1) above represents an ethyl group.

6. The method for producing 2-aminoethyl methacrylate hydrochloride according to claim 1 , wherein hydrogen chloride is hydrogen chloride gas.

7. The method for producing 2-aminoethyl methacrylate hydrochloride according to claim 1 , wherein the reaction of the ketimine compound of 2-aminoethyl methacrylate represented by Formula (1) with water and hydrogen chloride is carried out such that hydrogen chloride and the ketimine compound are added to the water such that the ratio of the accumulated supply amount of hydrogen chloride to the accumulated supply amount of the ketimine compound of 2-aminoethyl methacrylate is maintained at 1.0 or higher in equivalent ratio throughout the whole period from the starting point of mixing hydrogen chloride with the ketimine compound of 2-aminoethyl methacrylate to the end point of mixing the whole amount of hydrogen chloride.

8. The method for producing 2-aminoethyl methacrylate hydrochloride according to claim 1 , wherein the reaction of the ketimine compound of 2-aminoethyl methacrylate with water and hydrogen chloride is carried out in the presence of at least one organic solvent selected from the group consisting of tetrahydrofuran, methyl isobutyl ketone, methyl ethyl ketone, acetone and dioxane.

9. The method for producing 2-aminoethyl methacrylate hydrochloride according to claim 8 , wherein the organic solvent is at least one selected from the group consisting of methyl isobutyl ketone and methyl ethyl ketone.

10. The method for producing 2-aminoethyl methacrylate hydrochloride according to claim 8 , wherein the organic solvent is used in an amount four times as much as or less than the amount of the ketimine compound of 2-aminoethyl methacrylate represented by Formula (1) or (2) above in weight ratio.

11. The method for producing 2-aminoethyl methacrylate hydrochloride according to claim 1 , wherein the temperature in (A) is controlled to lie in a range of −10-60° C. from the starting point of supplying any of hydrogen chloride, ketimine, and water to the reaction vessel to the end point wherein all reactants have been supplied.

12. The method for producing 2-aminoethyl methacrylate hydrochloride according to claim 1 , wherein the temperature in (A) is controlled to lie in a range of −10-40° C., once all reactants have been added.

13. The method for producing 2-aminoethyl methacrylate hydrochloride according to claim 1 , further comprising (B) which comprises (b1) of separating solid precipitate from the mixture containing 2-aminoethyl methacrylate hydrochloride obtained in (A);
(b2) of washing the solid precipitate with a solvent; and (b3) of drying the washed solid precipitate.

14. The method for producing 2-aminoethyl methacrylate hydrochloride according to claim 13 , wherein the solvent in (b2) is at least one selected from the group consisting of acetone, methyl ethyl ketone, methyl isobutyl ketone, tetrahydrofuran and 1,4-dioxane.

15. The method for producing 2-aminoethyl methacrylate hydrochloride according to claim 13 wherein the solvent in (b2) contains a polymerization inhibitor.

16. The method for producing 2-aminoethyl methacrylate hydrochloride according to claim 1 , wherein 2-aminoethyl methacrylate hydrochloride is solid.

Assignees

• Mitsubishi Gas Chemical Co

Inventors

• Iida Yuri
• Takemoto Masaki
• Sato Hideyuki

Classifications

• C07C213/02 Primary

  by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups · CPC title

• C07C219/08

  having at least one of the hydroxy groups esterified by a carboxylic acid having the esterifying carboxyl group bound to an acyclic carbon atom of an acyclic unsaturated carbon skeleton · CPC title

• C07C249/02

  of compounds containing imino groups · CPC title

• C07C251/24

  having carbon atoms of imino groups bound to carbon atoms of six-membered aromatic rings · CPC title

• C07C251/04

  having carbon atoms of imino groups bound to hydrogen atoms or to acyclic carbon atoms · CPC title