Method for producing amino methylated bead polymerizates from N-carboxylic acid methylphthalimide esters

Patent metadata

Field	Value
Publication number	US-10016754-B2
Application number	US-201515536685-A
Country	US
Kind code	B2
Filing date	Dec 21, 2015
Priority date	Dec 22, 2014
Publication date	Jul 10, 2018
Grant date	Jul 10, 2018

Abstract

The invention relates to a process for preparing aminomethylated bead polymers from N-carboxymethylphthalimides, which are used as anion exchangers or can be converted further to chelate resins.

First claim

What is claimed is:

1. A process for preparing aminomethylated bead polymers, the process comprising:
a) converting monomer droplets composed of a mixture comprising at least one monovinylaromatic compound, at least one polyvinylaromatic compound, and at least one initiator to a bead polymer;
b) reacting the bead polymer from step a) with N-carboxymethylphthalimide in the presence of aliphatic saturated or unsaturated carboxylic anhydrides or carboxylic acids or in the presence of mixtures of aliphatic saturated or unsaturated carboxylic anhydrides and at least one aliphatic saturated or unsaturated carboxylic add, and
in the presence of at least one Friedel-Crafts catalyst,
to give a phthalimidomethylated bead polymer, and the amount of the compounds used:
N-carboxymethylphthalimide, bead polymer, aliphatic, saturated or unsaturated carboxylic anhydrides or carboxylic acids or mixtures thereof and Friedel-Crafts catalysts collectively in the reaction mixture is greater than 80% by weight, based on the total amount of the reaction mixture, and

c) hydrolyzing the phthalimidomethylated bead polymer to give an aminomethylated bead polymer.

2. The process according to claim 1 , wherein the monovinylaromatic compounds are styrene, α-methylstyrene, vinyltoluene, ethylstyrene, t-butylstyrene, chlorostyrene, bromostyrene, chloromethylstyrene, or vinylnaphthalene, or mixtures of these compounds.

3. Process according to claim 1 , wherein the polyvinylaromatic compounds are divinylbenzene, divinyltoluene, or trivinylbenzene, or mixtures of these compounds.

4. The process according to claim 1 , wherein the monovinylaromatic compound is styrene and the polyvinylaromatic compound is divinylbenzene.

5. The process according to claim 1 , wherein the N-carboxymethylphthalimide is N-acetoxymethylphthalimide.

6. The process according to claim 1 , wherein the Friedel-Crafts catalysts are a mixture of iron(III) chloride and sulphuric acid.

7. The process according to claim 1 , further comprising using 2 to 5 mol of N-carboxymethylphthalimide per mole of Friedel-Crafts catalyst.

8. The process according to claim 1 , further comprising using 10 −3 mol to 0.03 mol of N-carboxymethylphthalimide per gram of bead polymer.

9. The process according to claim 1 , further comprising using N-carboxymethylphthalimides in an amount of 1.6 to 2.5 mol per mole of carboxylic anhydrides or carboxylic acid.

10. The Process according to claim 1 , wherein the carboxylic anhydrides and carboxylic acids are a mixture of acetic anhydride and acetic acid.

11. The process according to claim 10 , wherein a ratio of acetic anhydride to acetic acid is 3:1 to 10:1.

12. The process according to claim 1 , further comprising collectively using the N-carboxymethylphthalimide compounds, the bead polymer, the carboxylic anhydrides or carboxylic acids or mixtures thereof, and the Friedel-Crafts catalysts in an amount greater than 95% by weight in the reaction mixture, based on the total amount of the reaction mixture.

13. The process according to claim 1 , further comprising conducting process step c) with aqueous or alcoholic solutions of an alkali metal hydroxide at temperatures between 100° C. and 250° C.

14. The process according to claim 1 , further comprising using a porogen in step a).

15. The process according to claim 1 , wherein the carboxylic acid is acetic acid.

Assignees

• Lanxess Deutschland Gmbh

Inventors

• Klipper Reinhold
• Vanhoorne Pierre
• Koop Bernd
• Rezkallah Areski

Classifications

• C08F212/26

  Nitrogen · CPC title

• B01J45/00

  Ion-exchange in which a complex or a chelate is formed; Use of material as complex or chelate forming ion-exchangers; Treatment of material for improving the complex or chelate forming ion-exchange properties (ion-exchange chromatography processes B01D15/36) · CPC title

• C08F8/30 Primary

  Introducing nitrogen atoms or nitrogen-containing groups · CPC title

• C08F8/12 Primary

  Hydrolysis · CPC title

• B01J41/12

  Macromolecular compounds · CPC title