Method for purifying acrylic acid derivative

Patent metadata

Field	Value
Publication number	US-10065917-B2
Application number	US-201615749185-A
Country	US
Kind code	B2
Filing date	Aug 5, 2016
Priority date	Aug 7, 2015
Publication date	Sep 4, 2018
Grant date	Sep 4, 2018

Abstract

The problem solved by the present invention is to provide a method for efficiently purifying acrylic acid derivative (I), more specifically a method for efficiently eliminating alcohol (II) from a composition containing acrylic acid derivative (I) and alcohol (II). This problem is solved by a method for purifying an acrylic acid derivative represented by Formula (I):

wherein

R 1 and R 2 are identical or different, and each represents alkyl, fluoroalkyl, aryl that may have one or more substituents, halogen, or hydrogen,

R 3 represents alkyl, fluoroalkyl, aryl that may have one or more substituents, or hydrogen, and

X represents alkyl, fluoroalkyl, halogen, or hydrogen,
the method comprising

step A of bringing composition A containing the acrylic acid derivative represented by Formula (I) and alcohol represented by Formula (II):

R 4 —OH,

wherein R 4 represents C 1-6 alkyl,

into contact with an acid anhydride to convert the alcohol into an ester compound that has a boiling point higher than the boiling point of the acrylic acid derivative represented by Formula (I).

First claim

The invention claimed is:

1. A method for purifying an acrylic acid derivative represented by Formula (I):

wherein
R 1 and R 2 are identical or different, and each represents alkyl, fluoroalkyl, aryl that may have one or more substituents, halogen, or hydrogen,
R 3 represents alkyl, fluoroalkyl, aryl that may have one or more substituents, or hydrogen, and
X represents alkyl, fluoroalkyl, halogen, or hydrogen,
the method comprising

step A of bringing a composition A containing the acrylic acid derivative represented by Formula (I) and alcohol represented by Formula (II):
R 4 —OH,

wherein R 4 represents alkyl, fluoroalkyl, or aryl that may have one or more substituents, into contact with an acid anhydride to convert the alcohol into an ester compound that has a boiling point higher than the boiling point of the acrylic acid derivative represented by Formula (I).

2. The method according to claim 1 , further comprising step B of separating the acrylic acid derivative represented by Formula (I) and the ester compound by distillation.

3. The method according to claim 1 , wherein R 1 represents hydrogen, C 1-20 alkyl, or C 1-20 fluoroalkyl.

4. The method according to claim 1 , wherein R 2 represents hydrogen, C 1-20 alkyl, or C 1-20 fluoroalkyl.

5. The method according to claim 1 , wherein R 3 represents C 1-20 linear alkyl.

6. The method according to claim 1 , wherein X represents C 1-20 alkyl, fluorine, chlorine, or hydrogen.

7. The method according to claim 1 , wherein R 4 represents C 1-6 alkyl.

8. The method according to claim 1 , wherein the acid anhydride is a cyclic acid anhydride.

9. The method according to claim 8 , wherein the acid anhydride is a compound represented by Formula (III-a):

wherein R 5 represents divalent hydrocarbon.

10. The method according to claim 9 , wherein the acid anhydride is succinic anhydride or phthalic anhydride.

11. The method according to claim 1 , wherein the composition A further contains a heteroatom-containing organic solvent, and wherein a composition B containing the acrylic acid derivative represented by Formula (I) and the heteroatom-containing organic solvent is obtained after the separation in step B.

12. The method according to claim 11 , wherein the heteroatom-containing organic solvent is separated and recovered from the composition B.

13. A method for producing an acrylic acid derivative represented by Formula (I):

wherein
R 1 and R 2 are identical or different, and each represents alkyl, fluoroalkyl, aryl that may have one or more substituents, halogen, or hydrogen,
R 3 represents alkyl, fluoroalkyl, aryl that may be substituted with one or more substituents, or hydrogen, and
X represents alkyl, fluoroalkyl, halogen, or hydrogen,
the method comprising purifying the acrylic acid derivative represented by Formula (I) by the purification method of claim 1 .

Assignees

• Daikin Ind Ltd

Inventors

• Matsuura Makoto
• Kishikawa Yosuke
• Yoshiyama Asako

Classifications

• C07C69/54

  Acrylic acid esters; Methacrylic acid esters · CPC title

• C07C69/653

  Acrylic acid esters; Methacrylic acid esters; Haloacrylic acid esters; Halomethacrylic acid esters · CPC title

• C07C67/60 Primary

  by treatment giving rise to chemical modification (by chemisorption C07C67/56) · CPC title

• C07C51/367

  by introduction of functional groups containing oxygen only in singly bound form · CPC title

• C07C67/54 Primary

  by distillation · CPC title