Method for purifying sulfonated aromatic monomer

Patent metadata

Field	Value
Publication number	US-9540319-B2
Application number	US-201113825692-A
Country	US
Kind code	B2
Filing date	Nov 14, 2011
Priority date	Nov 26, 2010
Publication date	Jan 10, 2017
Grant date	Jan 10, 2017

Abstract

The present invention relates to an improved method for purifying a sulfonated aromatic monomer. The method is an economical method capable of providing a highly pure sulfonated aromatic monomer, in which a salt precipitation step and a recrystallization step are simplified while maintaining the reaction conditions used in a conventional method for synthesizing the sulfonated aromatic monomer, and a purification process is carried out using an easily available and stable chemical substance. The sulfonated aromatic monomer obtained by the purification method will be useful for the preparation of a polymer for a polymer electrolyte membrane and will be advantageous to synthesize polymer with high molecular weight.

First claim

The invention claimed is:

1. A method for purifying a sulfonated aromatic monomer represented by formula 1 as shown in the following reaction scheme 2, the method comprising the steps of:
allowing an aromatic monomer 3 to react with fuming sulfuric acid 4 to prepare a sulfonated aromatic compound 2;
adding a salt to the compound 2 to precipitate a crude compound 1-1;
dissolving the crude compound 1-1 in water, wherein the step of dissolving the crude compound is carried out after washing the crude compound with alcohol selected from among methanol, ethanol or a mixture thereof to remove sulfuric acid remaining in the crude compound 1-1;
neutralizing the aqueous solution containing the crude compound, wherein the step of neutralizing the aqueous solution containing the crude compound is carried out using any one weak base selected from the group consisting of sodium carbonate, sodium hydrogen carbonate, ammonium hydroxide, ammonia, sodium phosphate and sodium sulfate; and
concentrating the neutralized aqueous solution and recrystallizing the concentrate from water, wherein alcohol is not added during the steps of neutralizing and recrystallizing:

wherein X is a halogen group element, and Y is any one selected from the group consisting of —S—, —C═O—, —P(O)(C 6 H 5 )— and —SO 2 —.

2. A method for a sulfonated aromatic monomer represented by formula 1 as shown in the following reaction scheme 2, the method comprising the steps of:
allowing an aromatic monomer 3 to react with fuming sulfuric acid 4 to prepare a sulfonated aromatic compound 2;
adding a salt to the compound 2 to precipitate a crude compound 1-1;
dissolving the crude compound 1-1 in water;
neutralizing the aqueous solution containing the crude compound, wherein the step of neutralizing the aqueous solution containing the crude compound is carried out by neutralizing the aqueous solution with anion exchange resin, followed by a washing step; and
concentrating the neutralized aqueous solution and recrystallizing the concentrate from water, wherein alcohol is not added during the steps of neutralizing and recrystallizing:

wherein X is a halogen group element, and Y is any one selected from the group consisting of —S—, —C═O—, —P(O)(C 6 H 5 )— and —SO 2 —.

3. The method of claim 2 , wherein the washing step is carried out by washing the anion exchange resin with the same amount of a base as that of the anion exchange resin.

Assignees

• Hong Young Taik
• Kim Seog Je
• Park Ji Young
• Lee Dong Hyun
• Korea Res Inst Chemical Tech

Inventors

• Hong Young Taik
• Kim Seog Je
• Park Ji Young
• Lee Dong Hyun

Classifications

• C07C315/06 Primary

  Separation; Purification; Stabilisation; Use of additives · CPC title

• C07C317/14

  having sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings · CPC title