High-purity carboxylic acid ester and method for producing same

Patent metadata

Field	Value
Publication number	US-11046634-B2
Application number	US-201916565767-A
Country	US
Kind code	B2
Filing date	Sep 10, 2019
Priority date	Oct 2, 2015
Publication date	Jun 29, 2021
Grant date	Jun 29, 2021

Abstract

A method for producing a high-purity carboxylic acid ester, the method including bringing a crude carboxylic acid ester that contains anionic impurities and Ag, Al, Au, Ca, Cr, Cu, Fe, K, Mg, Na, Sn, and Zn metal impurities into contact with a cation-exchange resin, followed by bringing the crude carboxylic acid ester into contact with an anion-exchange resin to obtain to provide a high-purity carboxylic acid ester in which the Ag, Al, Au, Ca, Cr, Cu, Fe, K, Mg, Na, Sn, and Zn metal impurity content are each less than 1 ppb and the anionic impurity content is less than 1 ppm.

First claim

The invention claimed is:

1. A method for producing a high-purity carboxylic acid ester, the method comprising:
contacting a first carboxylic acid ester composition that contains anionic impurities and at least silver, aluminum, gold, calcium, copper, iron, potassium, magnesium, sodium, tin, and zinc as metal impurities with a first weakly basic anion-exchange resin to obtain a second carboxylic acid ester composition;
contacting the second carboxylic acid ester composition with a strongly acidic cation-exchange resin to obtain a third carboxylic acid ester composition; and
contacting the third carboxylic acid ester composition with a second weakly basic anion-exchange resin to obtain the high-purity carboxylic acid ester,
wherein:
an amount of the silver, the aluminum, the gold, the calcium, the chromium, the copper, the iron, the potassium, the magnesium, the sodium, the tin, and the zinc metal impurities in the high-purity carboxylic acid ester is each less than 1 ppb, and
an amount of the anionic impurities in the high-purity carboxylic acid ester is less than 1 ppm.

2. The method according to claim 1 , wherein the carboxylic acid ester is at least one selected from the group consisting of propyl lactate, methyl α-hydroxyisobutyrate, ethyl α-hydroxyisobutyrate, propyl α-hydroxyisobutyrate, butyl α-hydroxyisobutyrate, methyl β-hydroxyisobutyrate, ethyl β-hydroxyisobutyrate, propyl β-hydroxyisobutyrate, and butyl β-hydroxyisobutyrate.

3. The method according to claim 1 , wherein the first carboxylic acid composition comprises at least 8 ppb of each of the silver, the aluminum, the gold, the calcium, the chromium, the copper, the iron, the potassium, the magnesium, the sodium, the tin, and the zinc metal impurities.

4. The method according to claim 1 , wherein the first carboxylic acid ester composition comprises at least 20 ppm of anionic impurities.

5. The method according to claim 1 , wherein the strongly acidic cation-exchange resin comprises a sulfonic acid group.

6. The method according to claim 1 , wherein each of the contacting the first carboxylic acid ester composition with the first weakly basic anion-exchange resin, the contacting the second carboxylic acid ester composition with the strongly acidic cation-exchange resin, and the contacting the third carboxylic acid ester composition with the second weakly basic anion-exchange resin occur at 100° C. or lower.

7. The method according to claim 1 , wherein:
the first and second weakly basic anion-exchange resins and the strongly acidic cation-exchange resin are each enclosed in separate columns, and
the first, second, and third carboxylic acid esters are flowed through each of the columns in each of the contactings.

8. The method according to claim 7 , wherein the flow through each of the columns has a space velocity of 1 to 50 Hr −1 .

9. The method according to claim 7 , wherein the flow through each of the columns has a space velocity of 10 to 20 Hr −1 .

Assignees

• Mitsubishi Gas Chemical Co

Inventors

• Muneyasu Kuniaki

Classifications

• C07C69/68 Primary

  Lactic acid esters · CPC title

• C07C67/56 Primary

  by solid-liquid treatment; by chemisorption · CPC title

• B01J47/028

  with alternately arranged cationic and anionic exchangers · CPC title

• B01J41/12

  Macromolecular compounds · CPC title

• B01J41/07

  in the weakly basic form · CPC title