Method of producing acrylonitrile dimer

Patent metadata

Field	Value
Publication number	US-12404234-B2
Application number	US-202017292951-A
Country	US
Kind code	B2
Filing date	Oct 14, 2020
Priority date	Nov 11, 2019
Publication date	Sep 2, 2025
Grant date	Sep 2, 2025

Abstract

The present invention relates to a method of producing an acrylonitrile dimer, the method including: feeding an acrylonitrile monomer, a nonpolar solvent, an alcohol solvent, and a phosphorus-based catalyst to a dimerization reactor to perform a dimerization reaction and reaction product to a distillation column; feeding the acrylonitrile monomer, the nonpolar solvent, and the alcohol solvent from the distillation column to the dimerization reactor; feeding an acrylonitrile dimer and the phosphorus-based catalyst from the distillation column to an extraction device; oxidizing the phosphorus-based catalyst by feeding water including an acid component to the extraction device to inactivate the phosphorus-based catalyst; and separating the inactivated phosphorus-based catalyst and the acrylonitrile dimer.

First claim

The invention claimed is:

1. A method of producing an acrylonitrile dimer, the method comprising:
feeding an acrylonitrile monomer, a nonpolar solvent, an alcohol solvent, and a phosphorus-based catalyst to a dimerization reactor to perform a dimerization reaction and feeding a reaction product to a distillation column;
feeding the acrylonitrile monomer, the nonpolar solvent, and the alcohol solvent partially or entirely separated from the distillation column to the dimerization reactor;
and feeding an acrylonitrile dimer and the phosphorus-based catalyst separated from the distillation column to an extraction device;
oxidizing the phosphorus-based catalyst by feeding water including an acid component to the extraction device to inactivate the phosphorus-based catalyst; and
separating the inactivated phosphorus-based catalyst and the acrylonitrile dimer.

2. The method of claim 1 , wherein the phosphorus-based catalyst is represented by Formula 1:

in Formula 1,
R represents an alkyl group having 1 to 5 carbon atoms or a cycloalkyl group having 1 to 8 carbon atoms,
each of R 1 to R 3 represents hydrogen, or an alkyl group, amine group, or alkoxy group having 1 to 5 carbon atoms, and
n and m are each independently an integer of 1 or 2.

3. The method of claim 1 , wherein a content of the alcohol solvent in the extraction device is 1 wt % or less.

4. The method of claim 1 , wherein a content of the nonpolar solvent in the extraction device is 5 wt % or less.

5. The method of claim 1 , wherein the water including the acid component is fed in an amount of 2 equivalents or more with respect to the phosphorus-based catalyst.

6. The method of claim 1 , wherein in the oxidizing of the phosphorus-based catalyst by feeding water including an acid component to the extraction device to inactivate the phosphorus-based catalyst, the water including the acid component includes one or more selected from the group consisting of a hydrochloric acid aqueous solution, a sulfuric acid aqueous solution, and a nitric acid aqueous solution.

7. The method of claim 1 , wherein the inactivated phosphorus-based catalyst is represented by Formula 2:

in Formula 2,
each of R 1 to R 3 represents hydrogen, or an alkyl group, amine group, or alkoxy group having 1 to 5 carbon atoms, and
n and m are each independently an integer of 1 or 2.

8. The method of claim 1 , wherein the inactivated phosphorus-based catalyst is a solid.

9. The method of claim 1 , wherein the separating of the inactivated phosphorus-based catalyst and the acrylonitrile dimer is performed using a filter.

10. The method of claim 1 , wherein the separated phosphorus-based catalyst is reused in the dimerization reactor.

11. The method of claim 1 , wherein in the distillation column, an operation temperature is 40° C. to 150° C., and an operation pressure is 0.001 bar to 3 bar.

12. The method of claim 2 , wherein in Formula 1, R represents an ethyl group, each of R 1 to R 3 represents hydrogen, and n is 2 and m is 1.

13. The method of claim 7 , wherein in Formula 2, each of R 1 to R 3 represents hydrogen, and n is 2 and m is 1.

Assignees

• Lg Chemical Ltd

Inventors

• Park Sae Hume
• Kim Ji Ha
• An Yu Jin
• Oh Wan Kyu
• Jung Hyun Chul
• Ahn Jeong Heon

Classifications

• C07C253/34

  Separation; Purification · CPC title

• B01J31/0255

  Phosphorus containing compounds · CPC title

• C07C255/09

  containing at least two cyano groups bound to the carbon skeleton · CPC title

• C07C253/32

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

• Y02P20/52

  using catalysts, e.g. selective catalysts · CPC title